Curable resin composition, cured product, and organic EL display element

Abstract

The present invention aims to provide a curable resin composition that has excellent curability with respect to long-wavelength light, low outgassing properties, and can suppress display defects in organic electroluminescence (EL) display devices. The present invention also aims to provide a cured product of the curable resin composition and an organic electroluminescence (EL) display device having the cured product. The present invention provides a curable resin composition used as a sealant for an organic electroluminescent display element, the curable resin composition comprising a curable resin, a photopolymerization initiator, and a sensitizer, wherein the sensitizer comprises an anthracene compound having an ester bond, and when a cured product of the curable resin composition is subjected to thermal desorption GC-MS measurement under thermal desorption conditions of 110°C and 30 minutes, the amount of anthraquinone quantified in toluene terms is 300 ppm or less.

Description

[Technical Field]

[0001] The present invention relates to a curable resin composition that has excellent curability with respect to long-wavelength light, low outgassing properties, and can suppress display defects in organic electroluminescence (EL) display devices. The present invention also relates to a cured product of the curable resin composition and an organic electroluminescence (EL) display device having the cured product. [Background technology]

[0002] An organic electroluminescence (hereinafter also referred to as "organic EL") display element has a laminate structure in which an organic light-emitting material layer is sandwiched between a pair of opposing electrodes, and when electrons are injected into this organic light-emitting material layer from one electrode and holes are injected from the other electrode, the electrons and holes combine in the organic light-emitting material layer to emit light. As such, organic EL display elements are self-luminous, and therefore have the advantages of better visibility than liquid crystal display elements and the like that require backlighting, of being able to be made thinner, and of being able to be driven by a low DC voltage.

[0003] The organic light-emitting material layer and electrodes constituting an organic EL display element have a problem in that their 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 isolate the organic light-emitting material layer and electrodes from the atmosphere to extend their lifespan. As a method for isolating the organic light-emitting material layer and electrodes from the atmosphere, the organic EL display element is sealed with a sealant (for example, Patent Document 1). When sealing an organic EL display element with a sealant, a method is usually used in which an inorganic film called a passivation film is provided on a laminate having an organic light-emitting material layer, and the inorganic film is sealed with a sealant in order to sufficiently suppress the permeation of moisture, oxygen, and the like.

[0004] In recent years, instead of bottom-emission organic EL display elements in which light emitted from an organic light-emitting material layer is extracted from the substrate surface on which the light-emitting elements are formed, top-emission organic EL display elements in which light is extracted from the top surface of the organic light-emitting layer have been attracting attention. This method has the advantage of a high aperture ratio and low-voltage drive, which is advantageous for extending the lifespan. In such top-emission organic EL display elements, the top surface of the light-emitting layer must be transparent, so they are sealed by laminating a transparent moisture-proof substrate such as glass on the top surface of the light-emitting element via a transparent sealing layer (for example, Patent Document 2).

[0005] One method for forming a sealing layer is to apply a sealant to a substrate using an inkjet method and then cure the sealant. Using such an inkjet application method allows for high-speed and uniform formation of a sealing layer. However, when a sealant suitable for application by an inkjet method is used in a top-emission organic EL display element, there is a problem that display defects such as dark spots may occur in the resulting organic EL display element. In particular, even sealants that do not cause display defects in bottom-emission organic EL display elements may cause display defects when used in a top-emission organic EL display element. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Laid-Open No. 2007-115692 [Patent Document 2] Japanese Patent Application Laid-Open No. 2009-051980 Summary of the Invention [Problem to be solved by the invention]

[0007] The present invention aims to provide a curable resin composition that has excellent curability with respect to long-wavelength light, low outgassing properties, and can suppress display defects in organic EL display devices. The present invention also aims to provide a cured product of the curable resin composition and an organic EL display device having the cured product. [Means for solving the problem]

[0008] The present invention provides a curable resin composition used as a sealant for an organic electroluminescent display element, the curable resin composition comprising a curable resin, a photopolymerization initiator, and a sensitizer, wherein the sensitizer comprises an anthracene compound having an ester bond, and when a cured product of the curable resin composition is subjected to thermal desorption GC-MS measurement under thermal desorption conditions of 110°C and 30 minutes, the amount of anthraquinone quantified in toluene terms is 300 ppm or less. The present invention will be described in detail below.

[0009] The present inventors investigated the use of a sensitizer in a curable resin composition used as an encapsulant for organic EL display devices, with the aim of reducing damage to the device, and curing the composition with long-wavelength light, such as 395 nm. Furthermore, in order to improve the transparency and curability of the curable resin composition, they investigated the use of an anthracene compound having an ester bond as the sensitizer. However, the resulting organic EL display device sometimes exhibited display defects such as dark spots. The present inventors believed that the cause of display defects such as dark spots when an anthracene compound having an ester bond is generated upon decomposition of the anthracene compound is acid derived from the ester bond. Therefore, the present inventors investigated the quantification of anthraquinone, which is generated together with the acid upon decomposition of the anthracene compound, by thermal desorption GC-MS measurement of the cured product under specific conditions, to a specific value or less. As a result, they discovered that a curable resin composition can be obtained that exhibits excellent curability with long-wavelength light and low outgassing, and that can suppress display defects in organic EL display devices, thereby completing the present invention.

[0010] The curable resin composition of the present invention has a cured product with an anthraquinone content of 300 ppm or less, as determined by toluene conversion, when subjected to thermal desorption GC-MS measurement at 110°C for 30 minutes. Because the anthraquinone content is 300 ppm or less, the curable resin composition of the present invention can provide an organic EL display device with excellent display performance. The upper limit of the anthraquinone content is preferably 250 ppm, and more preferably 200 ppm. It is most preferred that the anthraquinone content be 0 ppm. The amount of anthraquinone and the total amount of outgassing described below can be measured by measuring the amount of gas components generated when 1 mg of the cured product is heated under thermal desorption conditions of 110°C for 30 minutes using a thermal desorption device and a GC-MS device. The cured product used in the thermal desorption GC-MS measurement was prepared by irradiating the curable resin composition with ultraviolet light of 395 nm wavelength using an LED lamp at 2000 mJ / cm. 2 It can be obtained by irradiation.

[0011] The curable resin composition of the present invention preferably has a total outgassing amount of 6000 ppm or less as quantified in toluene terms when the cured product is subjected to thermal desorption GC-MS measurement under thermal desorption conditions of 110°C and 30 minutes. When the total outgassing amount is 6000 ppm or less, the curable resin composition of the present invention exhibits an excellent effect of suppressing the occurrence of dark spots and the like in the resulting organic EL display device. The upper limit of the total outgassing amount is more preferably 4000 ppm, and even more preferably 3500 ppm. It is most preferred that the total outgassing amount is 0 ppm.

[0012] The amount of anthraquinone and the total amount of outgassing can be set within the above-mentioned ranges by selecting and combining the types of each component, such as a sensitizer containing an anthracene compound having an ester bond, which will be described later, a curable resin, a photopolymerization initiator, and a stabilizer, and adjusting the content ratio thereof.

[0013] The curable resin composition of the present invention contains a curable resin. The curable resin may be a cationically polymerizable compound or a radically polymerizable compound, and preferably contains a cationically polymerizable compound.

[0014] Examples of the cationically polymerizable compound include an oxetane compound, an epoxy compound, a vinyl ether compound, etc. Among these, it is preferable that the curable resin contains at least one compound selected from the group consisting of an oxetane compound and an epoxy compound.

[0015] Examples of the oxetane compound include 3-ethyl-3-(((3-ethyloxetan-3-yl)methoxy)methyl)oxetane, 3-ethyl-3-((2-ethylhexyloxy)methyl)oxetane, 3-ethyl-3-((3-(triethoxysilyl)propoxy)methyl)oxetane, phenol novolac oxetane, and 1,4-bis(((3-ethyl-3-oxetanyl)methoxy)methyl)benzene. Of these, 3-ethyl-3-(((3-ethyloxetan-3-yl)methoxy)methyl)oxetane is preferred. These oxetane compounds may be used alone or in combination of two or more.

[0016] Examples of the epoxy compound include 1,7-octadiene diepoxide, neopentyl glycol diglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin diglycidyl ether, trimethylolpropane triglycidyl ether, phenyl glycidyl ether, phenylene diglycidyl ether, etc. Of these, 1,6-hexanediol diglycidyl ether is preferred. These epoxy compounds may be used alone or in combination of two or more.

[0017] Examples of the vinyl ether compound include benzyl vinyl ether, cyclohexanedimethanol monovinyl ether, dicyclopentadiene vinyl ether, 1,4-butanediol divinyl ether, cyclohexanedimethanol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, dipropylene glycol divinyl ether, and tripropylene glycol divinyl ether. These vinyl ether compounds may be used alone or in combination of two or more.

[0018] The radically polymerizable compound is preferably a (meth)acrylic compound. In this specification, the term "(meth)acrylic" refers to acrylic or methacrylic, the term "(meth)acrylic compound" refers to a compound having a (meth)acryloyl group, and the term "(meth)acryloyl" refers to acryloyl or methacryloyl.

[0019] Examples of the (meth)acrylic compound include isobornyl (meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, dicyclopentanyl (meth)acrylate, benzyl (meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrapropylene glycol di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, 1,12-dodecanediol di(meth)acrylate, and lauryl (meth)acrylate. Among these, isobornyl (meth)acrylate and 1,6-hexanediol di(meth)acrylate are preferred. These (meth)acrylic compounds may be used alone or in combination of two or more. In this specification, the term "(meth)acrylate" means acrylate or methacrylate.

[0020] The curable resin composition of the present invention contains a photopolymerization initiator. As the photopolymerization initiator, a photocationic polymerization initiator or a photoradical polymerization initiator is suitably used depending on the type of the curable resin used and the like.

[0021] The photocationic polymerization initiator is not particularly limited as long as it generates a protonic acid or a Lewis acid upon irradiation with light, and may be either an ionic photoacid generating type or a nonionic photoacid generating type.

[0022] The anion moiety of the ionic photoacid generating cationic photopolymerization initiator is, for example, BF4 - , PF6 - , SbF6 - , (BX4) -(wherein X represents a phenyl group substituted with at least two fluorine or trifluoromethyl groups). The anion moiety may be 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). Examples of the ionic photoacid-generating photocationic polymerization initiator include aromatic sulfonium salts, aromatic iodonium salts, aromatic diazonium salts, aromatic ammonium salts, and (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene)-Fe salts, each of which has the anion moiety.

[0023] Examples of the aromatic sulfonium salt include bis(4-(diphenylsulfonio)phenyl)sulfide bishexafluorophosphate, bis(4-(diphenylsulfonio)phenyl)sulfide bishexafluoroantimonate, 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, Examples of the sulfonium tetrakis(pentafluorophenyl)borate include 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(4-(2-hydroxyethoxy))phenylsulfonio)phenyl)sulfide tetrakis(pentafluorophenyl)borate, and tris(4-(4-acetylphenyl)thiophenyl)sulfonium tetrakis(pentafluorophenyl)borate. Of these, triarylsulfonium tetrakis(pentafluorophenyl)borate such as triphenylsulfonium tetrakis(pentafluorophenyl)borate is preferred.

[0024] 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 hexafluorophosphate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluoroantimonate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium tetrafluoroborate, and 4-methylphenyl-4-(1-methylethyl)phenyliodonium tetrakis(pentafluorophenyl)borate.

[0025] Examples of the aromatic diazonium salt include phenyldiazonium hexafluorophosphate, phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborate, and phenyldiazonium tetrakis(pentafluorophenyl)borate.

[0026] 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)-2-cyanopyridinium tetrafluoroborate, and 1-(naphthylmethyl)-2-cyanopyridinium tetrakis(pentafluorophenyl)borate.

[0027] 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-cyclopentadien-1-yl)((1-methylethyl)benzene)-Fe(II) hexafluoroantimonate, (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene)-Fe(II) tetrafluoroborate, and (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene)-Fe(II) tetrakis(pentafluorophenyl)borate.

[0028] Examples of the nonionic photoacid-generating cationic photopolymerization initiator include nitrobenzyl esters, sulfonic acid derivatives, phosphate esters, phenolsulfonic acid esters, diazonaphthoquinone, and N-hydroxyimide sulfonates.

[0029] Among the above-mentioned cationic photopolymerization initiators, commercially available ones include, for example, cationic photopolymerization initiators manufactured by Midori Chemical Industry Co., Ltd., cationic photopolymerization initiators manufactured by Union Carbide Corporation, cationic photopolymerization initiators manufactured by ADEKA Corporation, cationic photopolymerization initiators manufactured by 3M Corporation, cationic photopolymerization initiators manufactured by BASF Corporation, cationic photopolymerization initiators manufactured by Rhodia Corporation, and cationic photopolymerization initiators manufactured by San-Apro Corporation. Examples of the cationic photopolymerization initiators manufactured by Midori Chemical Co., Ltd. include DTS-200. Examples of the cationic photopolymerization initiators manufactured by Union Carbide include UVI6990 and UVI6974. Examples of the cationic photopolymerization initiators manufactured by ADEKA Corporation include SP-150 and SP-170. Examples of the cationic photopolymerization initiator manufactured by 3M include FC-508 and FC-512. Examples of the cationic photopolymerization initiators manufactured by BASF include IRGACURE261 and IRGACURE290. Examples of the cationic photopolymerization initiators manufactured by Rhodia include PI2074. Examples of the cationic photopolymerization initiators manufactured by San-Apro include CPI-100P, CPI-200K, and CPI-210S.

[0030] Examples of the photoradical polymerization initiator include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, and thioxanthone compounds.

[0031] Specific examples of the photoradical polymerization initiator include 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone, 1,2-(dimethylamino)-2-((4-methylphenyl)methyl)-1-(4-(4-morpholinyl)phenyl)-1-butanone, 2,2-dimethoxy-1,2-diphenylethan-1-one, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2-methyl Examples thereof include 1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 1-(4-(2-hydroxyethoxy)-phenyl)-2-hydroxy-2-methyl-1-propan-1-one, 1-(4-(phenylthio)phenyl)-1,2-octanedione 2-(O-benzoyloxime), 2,4,6-trimethylbenzoyldiphenylphosphine oxide, benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether.

[0032] The content of the photopolymerization initiator is preferably 0.01 parts by weight at the lower limit and 10 parts by weight at the upper limit relative to 100 parts by weight of the curable resin. When the content of the photopolymerization initiator is 0.01 parts by weight or more, the resulting curable resin composition has better photocurability. When the content of the photopolymerization initiator is 10 parts by weight or less, the curing reaction of the resulting curable resin composition does not become too fast, resulting in better workability and a more uniform cured product. A more preferred lower limit of the content of the polymerization initiator is 0.05 parts by weight, and a more preferred upper limit is 5 parts by weight.

[0033] The curable resin composition of the present invention may contain a thermal polymerization initiator within a range that does not impair the object of the present invention. As the thermal polymerization initiator, a thermal cationic polymerization initiator or a thermal radical polymerization initiator is suitably used depending on the type of the curable resin used, etc.

[0034] The thermal cationic polymerization initiator has an anion moiety of BF4 - , PF6 - , SbF6 - , or (BX4) - (wherein X represents a phenyl group substituted with at least two fluorine atoms or trifluoromethyl groups), sulfonium salts, phosphonium salts, ammonium salts, etc. are preferred. Of these, sulfonium salts and ammonium salts are preferred.

[0035] Examples of the sulfonium salt include triphenylsulfonium tetrafluoroborate and triphenylsulfonium hexafluoroantimonate.

[0036] Examples of the phosphonium salt include ethyltriphenylphosphonium hexafluoroantimonate and tetrabutylphosphonium hexafluoroantimonate.

[0037] Examples of the ammonium salts 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, and methylphenyldibenzylammonium hexafluorophosphate. , methylphenyldibenzylammonium hexafluoroantimonate, 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 trifluoromethanesulfonate, and the like.

[0038] Among the above-mentioned thermal cationic polymerization initiators, commercially available ones include, for example, thermal cationic polymerization initiators manufactured by Sanshin Chemical Industry Co., Ltd. and thermal cationic polymerization initiators manufactured by King Industries. Examples of the thermal cationic polymerization initiators manufactured by Sanshin Chemical Industry Co., Ltd. include San-Aid SI-60, San-Aid SI-80, San-Aid SI-B3, San-Aid SI-B3A, and San-Aid SI-B4. Examples of the thermal cationic polymerization initiators manufactured by King Industries include CXC-1612 and CXC-1821.

[0039] Examples of the thermal radical polymerization initiator include azo compounds, organic peroxides, and the like. Examples of the azo compound include 2,2'-azobis(2,4-dimethylvaleronitrile) and azobisisobutyronitrile. Examples of the organic peroxide include benzoyl peroxide, ketone peroxide, peroxyketal, hydroperoxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.

[0040] Among the above thermal radical polymerization initiators, commercially available ones include, for example, VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS-1001, and V-501 (all manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.).

[0041] The content of the thermal polymerization initiator is preferably 0.01 parts by weight at the lower limit and 10 parts by weight at the upper limit relative to 100 parts by weight of the curable resin. By setting the content of the thermal polymerization initiator within this range, the resulting curable resin composition has better storage stability and thermosetting properties. The more preferred lower limit of the content of the thermal polymerization initiator is 0.05 parts by weight, and the more preferred upper limit is 5 parts by weight.

[0042] The curable resin composition of the present invention contains a sensitizer. The sensitizer includes an anthracene compound having an ester bond. By including the anthracene compound having an ester bond as the sensitizer, the curable resin composition of the present invention has excellent curability and transparency with respect to light of long wavelengths.

[0043] Examples of the anthracene compound having an ester bond include 9,10-anthracene derivatives. Examples of the 9,10-anthracene derivatives include 9,10-bis(octanoyloxy)anthracene, 9,10-bis(2-ethylhexanoyloxy)anthracene, 9,10-bis(n-nonanoyloxy)anthracene, and 9,10-bis(acryloyloxy)anthracene. Among these, 9,10-bis(octanoyloxy)anthracene is preferred. Monosubstituted anthracene derivatives such as 9-octanoyloxyanthracene may also be used.

[0044] The content of the anthracene compound having an ester bond is preferably 0.1 parts by weight at the lower limit and 5 parts by weight at the upper limit relative to 100 parts by weight of the curable resin. When the content of the anthracene compound having an ester bond is 0.1 parts by weight or more, the sensitizing effect is more pronounced. When the content of the anthracene compound having an ester bond is 5 parts by weight or less, the resulting liquid crystal display device has better display performance. The more preferred lower limit of the content of the anthracene compound having an ester bond is 0.3 parts by weight, and the more preferred upper limit is 3 parts by weight.

[0045] The curable resin composition of the present invention may contain a heat curing agent within a range that does not impair the object of the present invention. Examples of the heat curing agent include hydrazide compounds, imidazole derivatives, acid anhydrides, dicyandiamide, guanidine derivatives, modified aliphatic polyamines, and addition products of various amines and epoxy resins. Examples of the hydrazide compound include 1,3-bis(hydrazinocarbonoethyl)-5-isopropylhydantoin, sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, and malonic acid dihydrazide. Examples of the imidazole derivatives include 1-cyanoethyl-2-phenylimidazole, N-(2-(2-methyl-1-imidazolyl)ethyl)urea, 2,4-diamino-6-(2'-methylimidazolyl-(1'))-ethyl-s-triazine, N,N'-bis(2-methyl-1-imidazolylethyl)urea, N,N'-(2-methyl-1-imidazolylethyl)-adipamide, 2-phenyl-4-methyl-5-hydroxymethylimidazole, and 2-phenyl-4,5-dihydroxymethylimidazole. Examples of the acid anhydride include tetrahydrophthalic anhydride and ethylene glycol bis(anhydrotrimellitate). These heat curing agents may be used alone or in combination of two or more.

[0046] Among the above-mentioned heat curing agents, commercially available ones include, for example, heat curing agents manufactured by Otsuka Chemical Co., Ltd. and heat curing agents manufactured by Ajinomoto Fine-Techno Co., Ltd. Examples of the heat curing agents manufactured by Otsuka Chemical Co., Ltd. include SDH and ADH. Examples of the heat curing agents manufactured by Ajinomoto Fine-Techno Co., Inc. include Amicure VDH, Amicure VDH-J, and Amicure UDH.

[0047] The content of the thermosetting agent is preferably 0.5 parts by weight at the lower limit and 30 parts by weight at the upper limit relative to 100 parts by weight of the curable resin. By using the thermosetting agent in this range, the resulting curable resin composition can have excellent thermosetting properties while maintaining excellent storage stability. The more preferred lower limit of the content of the thermosetting agent is 1 part by weight, and the more preferred upper limit is 15 parts by weight.

[0048] The curable resin composition of the present invention preferably contains a stabilizer. By containing the stabilizer, the curable resin composition of the present invention has better storage stability.

[0049] As the stabilizer, an aromatic amine compound is preferably used. Examples of the aromatic amine compound include benzylamine and aminophenol-type epoxy resin. Examples of the aminophenol type epoxy resin include triglycidyl-p-aminophenol. Of these, benzylamine is preferred. These stabilizers may be used alone or in combination of two or more.

[0050] The content of the stabilizer is preferably 0.001 parts by weight at the lower limit and 2 parts by weight at the upper limit relative to 100 parts by weight of the curable resin. By using the stabilizer in this range, the resulting curable resin composition has excellent storage stability while maintaining excellent curability. The more preferred lower limit of the stabilizer content is 0.005 parts by weight, and the more preferred upper limit is 1 part by weight.

[0051] The curable resin composition of the present invention may contain a silane coupling agent, which serves to improve the adhesion between the curable resin composition of the present invention and a substrate or the like.

[0052] Examples of the silane coupling agent include 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, etc. These silane coupling agents may be used alone or in combination of two or more.

[0053] The content of the silane coupling agent is preferably 0.1 parts by weight at the lower limit and 10 parts by weight at the upper limit relative to 100 parts by weight of the curable resin. By setting the content of the silane coupling agent within this range, the effect of improving adhesion is superior while suppressing bleeding out of excess silane coupling agent. The more preferred lower limit of the content of the silane coupling agent is 0.5 parts by weight, and the more preferred upper limit is 5 parts by weight.

[0054] The curable resin composition of the present invention may further contain a surface modifier within a range that does not impair the object of the present invention. By containing the surface modifier, the flatness of the coating film of the curable resin composition of the present invention can be improved. Examples of the surface modifier include surfactants and leveling agents.

[0055] Examples of the surface modifier include silicone-based and fluorine-based agents. Among the above surface modifiers, commercially available ones include, for example, surface modifiers manufactured by BYK Japan and surface modifiers manufactured by AGC Seimi Chemical Co., Ltd. Examples of the surface modifiers manufactured by BYK Japan include BYK-330, BYK-340, and BYK-345. An example of the surface modifier manufactured by AGC Seimi Chemical Co., Ltd. is Surflon S-611.

[0056] The curable resin composition of the present invention may contain a solvent for the purpose of adjusting viscosity or the like. However, since the remaining solvent may cause problems such as deterioration of the organic light-emitting material layer or generation of outgassing, it is preferable that the curable resin composition does not contain a solvent or that the solvent content is 0.05 wt % or less.

[0057] Furthermore, the curable resin composition of the present invention may contain various known additives such as a reinforcing agent, a softener, a plasticizer, a viscosity modifier, an ultraviolet absorber, and an antioxidant, as needed.

[0058] Examples of a method for producing the curable resin composition of the present invention include a method in which a curable resin, a photopolymerization initiator, a sensitizer, and additives such as a stabilizer and a surface modifier are mixed using a mixer. Examples of the mixer include a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a three-roll mixer.

[0059] The curable resin composition of the present invention can be suitably applied by an inkjet method. The curable resin composition of the present invention can be used for application by either a non-heating ink jet method or a heating ink jet method. In this specification, the "non-heated inkjet method" refers to a method of inkjet coating at a coating head temperature of less than 28°C, and the "heated inkjet method" refers to a method of inkjet coating at a coating head temperature of 28°C or higher.

[0060] The thermal inkjet method uses an inkjet coating head equipped with a heating mechanism. By incorporating a heating mechanism into the inkjet coating head, the viscosity and surface tension of the curable resin composition can be reduced when the composition is ejected.

[0061] Examples of inkjet coating heads equipped with the above-mentioned heating mechanism include the KM1024 series manufactured by Konica Minolta, Inc. and the SG1024 series manufactured by FUJIFILM Dimatix.

[0062] When the curable resin composition of the present invention is used for coating by the thermal inkjet method, the heating temperature of the coating head is preferably in the range of 28° C. to 80° C. When the heating temperature of the coating head is in this range, the increase in viscosity of the curable resin composition over time is further suppressed, and the discharge stability is further improved.

[0063] The curable resin composition of the present invention has a viscosity at 25° C. of preferably 5 mPa·s as a lower limit and 50 mPa·s as an upper limit. When the viscosity at 25° C. is within this range, the composition can be suitably applied by an inkjet method. In this specification, the "viscosity" refers to a value measured using an E-type viscometer at 25°C and 100 rpm. Examples of the E-type viscometer include the VISCOMETER TV-22 (manufactured by Toki Sangyo Co., Ltd.), and a CP1 type cone plate can be used.

[0064] When applied by the non-heated inkjet method, the viscosity of the curable resin composition of the present invention at 25°C is preferably 5 mPa·s at the lower limit and 20 mPa·s at the upper limit. Having the viscosity at 25°C within this range allows for suitable application by the non-heated inkjet method. When applied by the non-heated inkjet method, the viscosity of the curable resin composition of the present invention at 25°C is more preferably 8 mPa·s at the lower limit and 16 mPa·s at the upper limit, and even more preferably 10 mPa·s at the lower limit and 13 mPa·s at the upper limit.

[0065] On the other hand, when used for application by the thermal inkjet method, the viscosity of the curable resin composition of the present invention at 25°C is preferably 10 mPa·s at the lower limit and 50 mPa·s at the upper limit. Having the viscosity within this range allows for suitable application by the thermal inkjet method. When used for application by the thermal inkjet method, the viscosity of the curable resin composition of the present invention at 25°C is more preferably 20 mPa·s at the lower limit and 40 mPa·s at the upper limit.

[0066] The curable resin composition of the present invention has a surface tension at 25° C. of preferably 15 mN / m at its lower limit and 35 mN / m at its upper limit. Having a surface tension at 25° C. within this range allows the composition to be suitably applied by an inkjet method. The surface tension at 25° C. is more preferably 20 mN / m at its lower limit and 30 mN / m at its upper limit, still more preferably 22 mN / m at its lower limit and 28 mN / m at its upper limit. The surface tension is a value measured by the Wilhelmy method using a dynamic wettability tester, such as the WET-6100 model (manufactured by Rhesca).

[0067] The total light transmittance of the cured product of the curable resin composition of the present invention for light having a wavelength of 380 nm or more and 800 nm or less is preferably 80%. A total light transmittance of 80% or more provides the resulting organic EL display device with superior optical properties. The total light transmittance is more preferably 85%. The total light transmittance can be measured using, for example, a spectrometer. The spectrometer may be, for example, an AUTOMATIC HAZE METER MODEL TC-III DPK (manufactured by Tokyo Denshoku Co., Ltd.). The cured product used to measure the total light transmittance is, for example, a curable resin composition exposed to ultraviolet light of 395 nm wavelength using an LED lamp at 2000 mJ / cm. 2 It can be obtained by irradiation.

[0068] The curable resin composition of the present invention preferably has a transmittance of 85% or more at 400 nm at an optical path length of 20 μm after irradiating a cured product with ultraviolet light for 100 hours. Having a transmittance of 85% or more after irradiating with ultraviolet light for 100 hours results in high transparency, reduced light emission loss, and superior color reproducibility. The lower limit of the transmittance after irradiating with ultraviolet light for 100 hours is more preferably 90%, and even more preferably 95%. As the light source for irradiating the ultraviolet rays, for example, a conventionally known light source such as a xenon lamp or a carbon arc lamp can be used. The cured product used to measure the transmittance after 100 hours of ultraviolet irradiation was, for example, a curable resin composition exposed to ultraviolet light at a wavelength of 395 nm using an LED lamp at 2000 mJ / cm. 2 It can be obtained by irradiation.

[0069] The curable resin composition of the present invention has a moisture permeability of 100 g / m at a thickness of 100 μm, measured in accordance with JIS Z 0208, after exposing the cured product to an environment of 85°C and 85% RH for 24 hours. 2 It is preferable that the moisture permeability is 100 g / m or less. 2By satisfying the above condition, the effect of preventing moisture from reaching the organic light-emitting material layer and causing dark spots to occur can be improved, and the resulting organic EL display device can have improved reliability. The cured product used to measure the moisture permeability is, for example, a curable resin composition exposed to ultraviolet light of 395 nm wavelength using an LED lamp at 2000 mJ / cm. 2 It can be obtained by irradiation.

[0070] The curable resin composition of the present invention preferably has a moisture content of less than 0.5% when exposed to an environment of 85°C and 85% RH for 24 hours. A moisture content of less than 0.5% in the cured product is more effective in preventing deterioration of the organic light-emitting material layer due to moisture in the cured product, resulting in an organic EL display device with greater reliability. A more preferred upper limit of the moisture content of the cured product is 0.3%. Examples of methods for measuring the moisture content include a method of determining the moisture content by the Karl Fischer method in accordance with JIS K 7251, and a method of determining the weight increase after absorbing moisture in accordance with JIS K 7209-2. The cured product used to measure the moisture content is, for example, a curable resin composition irradiated with ultraviolet light of 395 nm wavelength by an LED lamp at 2000 mJ / cm. 2 It can be obtained by irradiation.

[0071] The present invention also includes a cured product of the curable resin composition of the present invention, i.e., a cured product of a sealant for organic EL display elements, wherein the sealant for organic EL display elements contains a curable resin, a photopolymerization initiator, and a sensitizer, and the sensitizer contains an anthracene compound having an ester bond, and when the cured product is subjected to thermal desorption GC-MS measurement under thermal desorption conditions of 110°C and 30 minutes, the amount of anthraquinone quantified in toluene terms is 300 ppm or less.

[0072] The cured product of the present invention can be obtained by irradiating the curable resin composition of the present invention with light. Specifically, the curable resin composition of the present invention has a curing rate of 300 mJ / cm2 More than 3000mJ / cm 2 The composition can be suitably cured by irradiating it with the following integrated amount of light: The curable resin composition of the present invention can also be cured by irradiating it with light having a long wavelength, such as 395 nm.

[0073] Examples of light sources used for the light irradiation include low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, excimer lasers, chemical lamps, black light lamps, microwave-excited mercury lamps, metal halide lamps, sodium lamps, halogen lamps, xenon lamps, LED lamps, fluorescent lamps, sunlight, electron beam irradiation devices, etc. These light sources may be used alone or in combination of two or more. These light sources are appropriately selected depending on the types of the photopolymerization initiator and the sensitizer.

[0074] Examples of means for irradiating the curable resin composition of the present invention with light include simultaneous irradiation from various light sources, sequential irradiation with a time lag, and a combination of simultaneous irradiation and sequential irradiation, and any of these irradiation means may be used.

[0075] Examples of a method for producing an organic EL display element using the curable resin composition of the present invention include a method including a step of applying the curable resin composition of the present invention to a substrate and a step of curing the applied curable resin composition.

[0076] In the step of applying the curable resin composition of the present invention to a substrate, the curable resin composition of the present invention may be applied to the entire surface of the substrate or to a part of the substrate. The shape of the sealing portion of the curable resin composition of the present invention formed by application 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, and may be a shape that completely covers the laminate, a closed pattern may be formed around the periphery of the laminate, or a pattern with a shape that has a partial opening around the periphery of the laminate.

[0077] The cured product of the present invention obtained by the step of curing the curable resin composition may be coated with an inorganic material film. As the inorganic material constituting the inorganic material film, a conventionally known material can be used, for example, silicon nitride (SiN x ) and silicon oxide (SiO x The inorganic material film may be composed of a single layer, or may be a laminate of multiple types of layers. The laminate may also be coated by alternately laminating the inorganic material film and the cured product of the present invention.

[0078] The method for producing the organic EL display element may include a step of bonding a substrate coated with the curable resin composition of the present invention (hereinafter also referred to as "one substrate") to another substrate. The substrate to which the curable resin composition 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, or may be a substrate on which such a laminate is not formed. When the one substrate is a substrate on which the laminate is not formed, the curable resin composition of the present invention may be applied to the one substrate so as to protect the laminate from the outside air when the other substrate is bonded to it. That is, the curable resin composition may be applied to the entire surface of the area where the laminate will be located when the other substrate is bonded to it, or a sealant portion having a closed pattern may be formed in a shape that completely fits the area where the laminate will be located when the other substrate is bonded to it.

[0079] The step of curing the curable resin composition may be performed before the step of bonding the one substrate to the other substrate, or may be performed after the step of bonding the one substrate to the other substrate. When the step of curing the curable resin composition is carried out before the step of bonding the one substrate and the other substrate, the curable resin composition of the present invention preferably has a pot life of 1 minute or more from the time of light irradiation until the curing reaction progresses and adhesion becomes impossible. By having the pot life of 1 minute or more, curing does not progress too much before the one substrate and the other substrate are bonded together, and higher adhesive strength can be obtained.

[0080] In the step of bonding the one substrate and the other substrate, the one substrate and the other substrate are preferably bonded together in a reduced pressure atmosphere. The preferred lower limit of the degree of vacuum under the reduced pressure atmosphere is 0.01 kPa, and the preferred upper limit is 10 kPa. When the degree of vacuum under the reduced pressure atmosphere is within this range, bubbles in the curable resin composition of the present invention can be more efficiently removed when bonding the one substrate and the other substrate together, without requiring a long time to achieve a vacuum state due to the airtightness of the vacuum device or the capacity of the vacuum pump.

[0081] The curable resin composition of the present invention is used as a sealant for an organic EL display device. An organic EL display device having the cured product of the present invention also constitutes the present invention.The curable resin composition of the present invention is particularly suitable for use in sealing top-emission organic EL display devices. The curable resin composition of the present invention is also suitable for use as an adhesive for lithium ion batteries. [Effects of the Invention]

[0082] According to the present invention, it is possible to provide a curable resin composition that has excellent curability with respect to long-wavelength light and low outgassing properties, and that can suppress display defects in organic EL display elements. Furthermore, according to the present invention, it is possible to provide a cured product of the curable resin composition and an organic EL display element having the cured product. DETAILED DESCRIPTION OF THE INVENTION

[0083] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0084] Example 1 ,3,4,Reference Example 2, 5. Comparative Examples 1 and 2) According to the blending ratios shown in Table 1, each material was uniformly mixed and stirred at a stirring speed of 300 rpm using a homodisper type mixing mixer. ,3,4,Reference Example 2, Curable resin compositions were prepared according to Comparative Examples 1 and 2. The Homodisper L model (manufactured by Primix Corporation) was used as the Homodisper type agitation mixer. The obtained curable resin composition was irradiated with 2000 mJ / cm of ultraviolet light at a wavelength of 395 nm using an LED lamp in a dry chamber with a dew point of -50°C or less. 2 Cured products were obtained by irradiating the cured products. 1 mg of each cured product was heated at 110°C for 30 minutes using a thermal desorption device and a GC-MS device, and the amount of anthraquinone and total outgassing, calculated as toluene, were measured. The specific measurement conditions are shown below. Thermal desorption device: Turbo Matrix 650 (PerkinElmer) Thermal desorption conditions: 110°C, 30 minutes Split: Inlet 15mL / min, outlet 15mL / min, injection volume 5.2% GC-MS device: JMS Q1000 (manufactured by JEOL Ltd.) Separation column: EQUITY-1 (non-polar) 0.32mm x 60m x 0.25μm GC heating rate: 40°C for 4 minutes → 10°C / minute → 300°C for 10 minutes Carrier gas (flow rate): He (1.5 mL / min) MS measurement range: 29-600 amu (scan 500 ms) Ionization voltage: 70 eV MS temperature: ion source 230°C, interface 250°C The results are shown in Table 1.

[0085] <Evaluation> Example , Reference Examples, and 、The curable resin compositions obtained in the comparative examples were evaluated as follows, and the results are shown in Table 1.

[0086] (1) Viscosity Example , Reference Examples, and 、 The viscosity of each of the curable resin compositions obtained in the comparative examples was measured using an E-type viscometer (manufactured by Toki Sangyo Co., Ltd., "VISCOMETER TV-22") with a CP1 type cone plate at 25°C and 100 rpm.

[0087] (2)Surface tension Example , Reference Examples, and 、 The surface tension of each of the curable resin compositions obtained in the comparative examples was measured at 25°C using a dynamic wettability tester (manufactured by Rhesca Corporation, "WET-6100 model").

[0088] (3) Display performance of organic EL display elements Organic EL display elements were obtained by the methods shown in (3-1) to (3-4) below, and the display performance of the obtained organic EL display elements was evaluated by the methods shown in (3-5) and (3-6) below.

[0089] (3-1) Preparation of a substrate on which a laminate having an organic light-emitting material layer is arranged The substrate was a 25 mm long, 25 mm wide, 0.7 mm thick glass substrate with an ITO electrode deposited to a thickness of 1000 Å. The substrate was ultrasonically cleaned for 15 minutes each in acetone, alkaline aqueous solution, ion-exchanged water, and isopropyl alcohol, then cleaned for 10 minutes in boiled isopropyl alcohol, and then immediately treated with a UV-ozone cleaner. The UV-ozone cleaner used was an NL-UV253 (manufactured by Japan Laser Electronics Co., Ltd.). Next, the substrate immediately after the previous treatment was fixed to the substrate holder of the vacuum deposition device, 200 mg of N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (α-NPD) was placed in a biscuit crucible, and 200 mg of tris(8-quinolinolato)aluminum (Alq3) was placed in another biscuit crucible. The inside of the vacuum chamber was then heated to 1 × 10 -4The pressure was reduced to 100 Pa. The crucible containing α-NPD was then heated, and α-NPD was deposited on the substrate at a deposition rate of 15 Å / s, forming a hole transport layer with a thickness of 600 Å. Next, the crucible containing Alq3 was heated, and an organic light-emitting material layer with a thickness of 600 Å was formed at a deposition rate of 15 Å / s. The substrate with the hole transport layer and organic light-emitting material layer formed thereon was then transferred to another vacuum evaporation apparatus equipped with tungsten resistance heating boats. 200 mg of lithium fluoride was placed in one of the tungsten resistance heating boats in the vacuum evaporation apparatus, and 1.0 g of aluminum wire was placed in the other tungsten resistance heating boat. The evaporator in the vacuum evaporation apparatus was then heated to 2×10 -4 The pressure was reduced to 100 Pa, and lithium fluoride was deposited at a deposition rate of 0.2 Å / s to form a 5 Å film, followed by aluminum deposition at a rate of 20 Å / s to form a 1000 Å film. The pressure inside the deposition chamber was returned to normal pressure with nitrogen, and the substrate on which the 10 mm × 10 mm stack having the organic light-emitting material layer was placed was removed.

[0090] (3-2) Coating with inorganic material film A mask having an opening of 13 mm×13 mm was placed on the substrate on which the obtained laminate was placed, and an inorganic material film was formed by plasma CVD so as to cover the entire laminate. The plasma CVD method was performed using SiH4 gas and nitrogen gas as raw material gases, with flow rates of SiH4 gas 10 sccm and nitrogen gas 200 sccm, under the following conditions: RF power 10 W (frequency 2.45 GHz), chamber temperature 100°C, and chamber pressure 0.9 Torr. The thickness of the formed inorganic material film was about 1 μm.

[0091] (3-3) Formation of hardened product The glass cap having a 15 mm x 15 mm recess was prepared separately. , Reference Examples, and 、Each of the curable resin compositions obtained in the comparative examples was applied to the entire surface to a thickness of 10 μm using an inkjet discharger, NanoPrinter 300 (manufactured by Microjet Co., Ltd.), and an IJH-30 (manufactured by IJT Co., Ltd.) as the inkjet discharger and the inkjet application head, respectively, and the inkjet application was performed without heating (head temperature 25° C.). Then, an LED lamp was used to irradiate ultraviolet light with a wavelength of 395 nm at 2000 mJ / cm 2 The curable resin composition was cured by irradiation to form a cured product.

[0092] (3-4) Glass cap sealing A low-moisture permeable epoxy adhesive was applied to the periphery of the glass cap obtained in the above "(3-3) Formation of a cured product," and the glass cap was placed over the substrate obtained in the above "(3-2) Coating with an inorganic material film," and sealed to obtain an organic EL display element for evaluation.

[0093] (3-5) Measurement of initial dark spot diameter The resulting organic EL display device was observed under an optical microscope to see if it emitted light when a voltage of 3 V was applied, and the diameter of the initial dark spots was measured. When multiple dark spots were present, those with a diameter of around 20 μm were given priority for observation.

[0094] (3-6) Dark spot diameter expansion rate The obtained organic EL display element was heated for 30 minutes in an environment at a temperature of 110°C and a humidity of less than 1%, and then a voltage of 3 V was applied. The light-emitting state of the organic EL display element was observed using an optical microscope, and the dark spot diameter after 30 minutes at 110°C was measured in the same manner as in "(3-5) Measurement of initial dark spot diameter" above. The display performance of the organic EL display element was evaluated as follows: when the dark spot diameter enlargement rate was 2.5 times or less, it was marked as "◎", when it was more than 2.5 times and 3.0 times or less, it was marked as "◯", when it was more than 3.0 times and 3.5 times or less, it was marked as "△", and when it was more than 3.5 times, it was marked as "×". The dark spot diameter expansion rate was calculated using the following formula. Dark spot diameter expansion rate = (dark spot diameter after 30 minutes at 110°C) / (initial dark spot diameter)

[0095] [Table 1] [Industrial Applicability]

[0096] According to the present invention, it is possible to provide a curable resin composition that has excellent curability with respect to long-wavelength light and low outgassing properties, and that can suppress display defects in organic EL display elements. Furthermore, according to the present invention, it is possible to provide a cured product of the curable resin composition and an organic EL display element having the cured product.

Claims

1. A curable resin composition used as a sealant for an organic EL display element, comprising: Contains a curable resin, a photopolymerization initiator, a sensitizer, and a stabilizer, the curable resin contains at least one selected from the group consisting of an oxetane compound, an epoxy compound, a vinyl ether compound, and a (meth)acrylic compound; the sensitizer includes an anthracene compound having an ester bond, The stabilizer comprises an aromatic amine compound, the curable resin composition has a viscosity at 25°C of 5 mPa·s or more and 50 mPa·s or less; a cured product of the curable resin composition is subjected to thermal desorption GC-MS measurement under thermal desorption conditions of 110°C and 30 minutes, and the amount of anthraquinone quantified in toluene terms is 300 ppm or less; When a cured product of the curable resin composition is subjected to thermal desorption GC-MS measurement under thermal desorption conditions of 110°C and 30 minutes, the total amount of outgassing quantified in toluene terms is 6000 ppm or less. A curable resin composition characterized by:

2. 2. The curable resin composition according to claim 1, which has a surface tension at 25°C of 15 mN / m or more and 35 mN / m or less.

3. A cured product of the curable resin composition according to claim 1 or 2.

4. An organic EL display device comprising the cured product according to claim 3.

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