Organic light-emitting element encapsulation composition and organic light-emitting element display device including an organic layer produced therefrom

Abstract

An organic light-emitting device encapsulation composition and an organic light-emitting device display including an organic layer formed therefrom are provided, which contain one or more indole groups, a silicone-containing photocurable monomer, a photocurable monomer, and a photopolymerization initiator.

Description

Technical Field

[0001] The present invention relates to a composition for encapsulating an organic light-emitting device and an organic light-emitting device display device including an organic layer manufactured therefrom.

Background Art

[0002] When external moisture, oxygen, etc. penetrate into an organic light-emitting device, it can be easily damaged and lose its function, resulting in a decrease in reliability. Therefore, an organic light-emitting device must be encapsulated by a sealing layer including an organic layer and an inorganic layer formed of a composition for encapsulating an organic light-emitting device.

[0003] The sealing layer can include a structure in which an organic layer and an inorganic layer are repeatedly formed. For example, a sealing layer is formed by alternately and repeatedly forming an organic layer and an inorganic layer such as an organic layer - inorganic layer - organic layer - inorganic layer on an organic light-emitting device. Unlike the organic layer, the inorganic layer can be formed of an inorganic substance. Generally, the inorganic layer may be formed by a plasma process and a vacuum process, for example, sputtering, chemical vapor deposition, plasma chemical vapor deposition, evaporation, sublimation, electron cyclotron resonance - plasma vapor deposition, and combinations thereof.

[0004] The background art of the present invention is described in Korean Patent Publication No. 10 - 2016 - 0150255, etc.

Summary of the Invention

Problems to be Solved by the Invention

[0005] An object of the present invention is to provide a composition for encapsulating an organic light-emitting device that has high solution stability even when containing a UV absorption type photocurable monomer and high storage stability when stored for a long period of time.

[0006] Another object of the present invention is to provide a composition for encapsulating an organic light-emitting device that forms an organic layer having a low dielectric constant after curing and a low light transmittance at a wavelength of 420 nm or less even when containing a UV absorption type photocurable monomer.

Means for Solving the Problems

[0007] One aspect of the present invention is a composition for encapsulating an organic light-emitting element.

[0008] The composition for encapsulating an organic light-emitting element contains one or more indole groups, a silicone-containing photocurable monomer, a photocurable monomer, and a photopolymerization initiator.

[0009] The organic light-emitting element display device of the present invention includes an organic layer formed of the composition for encapsulating an organic light-emitting element of the present invention.

Advantages of the Invention

[0010] The present invention can provide a composition for encapsulating an organic light-emitting element that has high solution stability even when containing a UV-absorbing photocurable monomer and high storage stability even when stored for a long period.

[0011] The present invention can provide a composition for encapsulating an organic light-emitting element that forms an organic layer having a low dielectric constant after curing and a low light transmittance at a wavelength of 420 nm or less even when containing a UV-absorbing photocurable monomer.

Brief Description of the Drawings

[0012]

Figure 1

Figure 2

Modes for Carrying Out the Invention

[0013] With reference to the accompanying drawings, the present invention will be described in detail by way of examples so that those having ordinary knowledge in the technical field to which the present invention pertains can easily implement it. The present invention can be embodied in various different forms and is not limited to the examples described herein. In the drawings, parts not related to the description are omitted in order to clearly explain the present invention, and the same reference numerals are given to the same or similar components throughout the specification. In the drawings, the lengths and sizes of the respective components are for the purpose of explaining the present invention, and the present invention is not limited to the lengths and sizes of the respective components described in the drawings.

[0014] The terms used herein are merely for the purpose of explaining exemplary embodiments and are not intended to limit the present invention. Singular expressions include plural expressions unless the context clearly indicates otherwise.

[0015] As used herein, “(meth)acryl” means acrylic and / or methacrylic.

[0016] As used herein, “substituted” can mean that, unless otherwise defined, one or more hydrogen atoms of the functional groups cited in the present invention are substituted with a halogen (F, Cl, Br or I), a hydroxy group, a nitro group, a cyano group, an imino group (=NH, =NR, R is an alkyl group having 1 to 10 carbon atoms), an amino group (-NH2, -NH(R’), -N(R’’)(R’’’), R’, R’’, R’’’ are each independently an alkyl group having 1 to 10 carbon atoms), an amidino group, a hydrazine or a hydrazone group, a carboxy group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms, or a heterocycloalkyl group having 2 to 30 carbon atoms.

[0017] As used herein, when describing a numerical range, “X to Y” means X or more and Y or less (X ≦ and ≦ Y).

[0018] The composition for encapsulating an organic light-emitting device according to an embodiment of the present invention (hereinafter also referred to as "composition") has high liquid-making stability even when it contains a UV-absorbing type photocurable monomer, and high storage stability even when stored for a long period of time, and can form an organic layer with a low dielectric constant after curing.

[0019] In the present specification, "high liquid-making stability of the UV-absorbing type photocurable monomer" means that the solubility of the UV-absorbing type photocurable monomer in the composition is high, so even when the UV-absorbing type photocurable monomer is included in the composition, it means that there is no precipitation and / or aggregation of the UV-absorbing type photocurable monomer. A composition with high liquid-making stability has excellent coatability of the composition because there is no precipitation, precipitation and / or aggregation of the monomer even when it contains a UV-absorbing type photocurable monomer, the thickness after curing is uniform, and an organic layer excellent in light transmittance in the visible light region can be formed, so the screen quality of the display device can be improved. The determination of whether the liquid-making stability is high may be performed by the method described in the following experimental example.

[0020] In the present specification, "high storage stability" means that when a composition containing a UV-absorbing type photocurable monomer is placed at room temperature (e.g., 25°C) for one week or more, there is no precipitation, precipitation and / or aggregation of the UV-absorbing type photocurable monomer at all. A composition with high storage stability can be sufficiently used as a composition for forming an organic layer even after a long period of time has passed since the composition was manufactured, so the economy and processability of the composition can be excellent. The determination of whether the storage stability is high may be performed by the method described in the following experimental example.

[0021] The organic layer formed of the composition of the present invention may have a dielectric constant of 3.2 or less, for example, 1.5 to 3.2. Within the above range, the performance of the organic light-emitting device can be successfully realized without being affected by external static electricity or electricity.

[0022] The composition of the present invention contains (A) one or more indole group and silicone-containing photocurable monomers, (B) a photocurable monomer, and (C) a photopolymerization initiator.

[0023] Hereinafter, each component in the composition of an embodiment of the present invention will be described in detail.

[0024] One or more indole groups and a silicone-containing photocurable monomer One or more indole group-containing and silicone-containing photocurable monomers are UV absorption-type photocurable monomers, and by reducing the light transmittance at a wavelength of 420 nm or less, for example, 405 nm to 420 nm, of the organic layer formed after curing of the composition, damage to the organic light-emitting device by UV can be prevented. When the organic light-emitting device is irradiated with UV, the organic light-emitting device is damaged and thus its original function cannot be surely realized. In one specific example, the organic layer may have a light transmittance of 10% or less, specifically, 0%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5%, 7%, 7.5%, 8%, 8.5%, 9%, 9.5%, 10%, for example, 0% to 10% at a wavelength of 420 nm or less, specifically, 405 nm, 406 nm, 407 nm, 408 nm, 409 nm, 410 nm, 411 nm, 412 nm, 413 nm, 414 nm, 415 nm, 416 nm, 417 nm, 418 nm, 419 nm, 420 nm, for example, 405 nm to 420 nm.

[0025] One or more indole group-containing and silicone-containing photocurable monomers can provide a composition having high liquid preparation stability and high storage stability even when stored for a long time when combined with the photocurable monomers described below.

[0026] One or more indole group-containing and silicone-containing photocurable monomers have an indole group among several functional groups that absorb light at a wavelength of 420 nm or less, and when combined with the photocurable monomers described below, can reduce the light transmittance at a wavelength of 420 nm or less of the organic layer. The photocurable monomer is a photocurable functional group and can increase the photocuring rate when combined with the (B) photocurable monomer described below by having a (meth)acrylate group or a vinyl group.

[0027] When one or more indole groups and silicone-containing photocurable monomers are combined with the (B) photocurable monomer described below, they can provide high solution stability and high storage stability without adversely affecting the solution stability and storage stability. Preferably, the photocurable monomer can have one or more siloxane bonds (-Si-O-Si-). One or more indole groups and silicone-containing photocurable monomers may be included singly or in combination of two or more in the composition.

[0028] In one specific example, one or more indole groups and silicone-containing photocurable monomers can be represented by the following Chemical Formula 1:

[0029]

Chemical Formula

[0030] (In the above Chemical Formula 1, R1 is hydrogen or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, R2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted arylalkyl group having 7 to 20 carbon atoms, R3, R4, R5, and R6 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, L1 and L2 are each independently hydrogen, a cyano group (-CN), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 20 carbon atoms, *-R 7 -epoxy group (* is the bonding site of the element, and R 7 is an alkylene group having 1 to 5 carbon atoms.), or a siloxane group-containing (meth)acrylate group, One or more of L1 and L2 are a siloxane group-containing (meth)acrylate group or -R 7 -epoxy group.).

[0031] In the above Chemical Formula 1, the "siloxane group-containing (meth)acrylate group" can be represented by the following Chemical Formula 2:

[0032]

Chemical Formula

[0033] (In the above Chemical Formula 2, * represents the bonding site of the element, R7 and R8 are each independently a single bond or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, R9 is hydrogen or a methyl group, X1, X2, X3, and X4 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or *-(-O-Si(R 11 )(R 12 ))-) p -O-Si(R 13 )(R 14 )(R 15 )(* represents the bonding site to Si, and R 11 , R 12 , R 13 , R 14 , R 15 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and p is an integer from 0 to 10.) m is 0 or 1, n is from 1 to 10.).

[0034] n may be an integer or an average value.

[0035] TIFF2025520643000004.tif14168

[0036] Preferably, in Chemical Formula 1, R1 may be hydrogen.

[0037] Preferably, in Chemical Formula 1, L1 and L2 are each independently hydrogen, a cyano group (-CN), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a siloxane group-containing (meth)acrylate group, and one or more of L1 and L2 may be a siloxane group-containing (meth)acrylate group.

[0038] Preferably, in Chemical Formula 2, R7 and R8 are each independently a single bond or a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, and X1, X2, X3, and X4 are each independently a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or *-(-O-Si(R 11 )(R 12 )-) p -O-Si(R 13 )(R 14 )(R 15 )(* is a bonding site to Si, and R 11 , R 12 , R 13 , R 14 , R 15 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and p is an integer from 0 to 10.). Preferably, R 11 , R 12 , R 13 , R 14 , R 15 may each independently be a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0039] In one specific example, the photocurable monomer may be represented by any one of the following Chemical Formulas 1-1 to 1-12:

[0040]

Chemical Formula

[0041]

Chemical Formula

[0042]

Chem.

[0043]

Chem.

[0044]

Chem.

[0045]

Chem.

[0046]

Chem.

[0047]

Chem.

[0048]

Chem.

[0049]

Chem.

[0050]

Chem.

[0051]

Chem.

[0052] (In the above Chemical formula 1-1 to 1-12, R9 is hydrogen or a methyl group, Me is a methyl group, and Et is an ethyl group.)

[0053] One or more indole groups and silicone-containing photocurable monomers may be produced by ordinary methods known to those skilled in the art or used as commercially available products.

[0054] (A) One or more indole groups and silicone-containing photocurable monomers may be contained in an amount of 0.01 to 10 parts by weight, specifically 0.01 part by weight, 0.05 part by weight, 0.1 part by weight, 0.5 part by weight, 1 part by weight, 1.5 parts by weight, 2 parts by weight, 2.5 parts by weight, 3 parts by weight, 3.5 parts by weight, 4 parts by weight, 4.5 parts by weight, 5 parts by weight, 5.5 parts by weight, 6 parts by weight, 6.5 parts by weight, 7 parts by weight, 7.5 parts by weight, 8 parts by weight, 8.5 parts by weight, 9 parts by weight, 9.5 parts by weight, 10 parts by weight, preferably 1 to 10 parts by weight, and more preferably 1 to 5 parts by weight, based on 100 parts by weight of the total of the photocurable monomers. Within the above content range, by reducing the light transmittance at a wavelength of 420 nm or less, preferably at a wavelength of 405 nm, damage to the organic light-emitting device from external UV can be prevented, and the plasma resistance can be enhanced, and it may not adversely affect the solution stability and storage stability.

[0055] Photocurable monomer (B) The photocurable monomer may form the matrix of the organic layer after curing or may reduce the dielectric constant of the organic layer after curing. The photocurable monomer is different from the one or more indole groups and silicone-containing photocurable monomers.

[0056] The photocurable monomer can contain one or more of (B1) a non-silicone-based photocurable monomer having no silicone and (B2) a silicone-based photocurable monomer having silicone. Preferably, the photocurable monomer can increase the photocuring rate and realize an organic layer with a low dielectric constant by containing a mixture of a non-silicone-based photocurable monomer and a silicone-based photocurable monomer.

[0057] (B1) The non-silicone-based photocurable monomer can contain a monomer having one or more photocurable functional groups, for example, a (meth)acrylate group. The non-silicone-based photocurable monomer can contain one or more of a non-silicone-based photocurable monofunctional monomer and a non-silicone-based photocurable polyfunctional monomer. The non-silicone-based photocurable monomer may be non-aromatic or aromatic, preferably non-aromatic.

[0058] The non-silicone-based photocurable monofunctional monomer is non-aromatic and can contain a mono(meth)acrylate having a linear or branched alkyl group with 1 to 20 carbon atoms in the ester moiety. For example, the non-silicone-based photocurable monofunctional monomer can contain one or more of tetradecyl (meth)acrylate including octyl (meth)acrylate, nonyl (meth)acrylate, lauryl (meth)acrylate, undecyl (meth)acrylate, dodecyl (meth)acrylate, tridecyl (meth)acrylate, tetradecyl (meth)acrylate, 2-decyltetradecyl (meth)acrylate, etc., and isostearyl (meth)acrylate.

[0059] The non-silicone-based photocurable monofunctional monomer is aromatic and can include, but is not limited to, a compound represented by the following Chemical Formula 3.

[0060]

Chemical formula

[0061] (In the above Chemical Formula 3, R1 is hydrogen or a methyl group, R2 is a substituted or unsubstituted C6 to C50 aryl group, or a substituted or unsubstituted C6 to C50 aryloxy group, s is an integer from 0 to 10.)

[0062] Specifically, the compound represented by Chemical Formula 3 may include, but is not limited to, 2-phenylphenoxyethyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenyl (meth)acrylate, phenoxy (meth)acrylate, 2-ethylphenoxy (meth)acrylate, benzyl (meth)acrylate, 2-phenylethyl (meth)acrylate, 3-phenylpropyl (meth)acrylate, 4-phenylbutyl (meth)acrylate, 2-(2-methylphenyl)ethyl (meth)acrylate, 2-(3-methylphenyl)ethyl (meth)acrylate, 2-(4-methylphenyl)ethyl (meth)acrylate, 2-(4-propylphenyl)ethyl (meth)acrylate, 2-(4-(1-methylethyl)phenyl)ethyl (meth)acrylate, 2-(4-methoxyphenyl)ethyl (meth)acrylate, 2-(4-cyclohexylphenyl)ethyl (meth)acrylate, 2-(2-chlorophenyl)ethyl (meth)acrylate, 2-(3-chlorophenyl)ethyl (meth)acrylate, 2-(4-chlorophenyl)ethyl (meth)acrylate, 2-(4-bromophenyl)ethyl (meth)acrylate, 2-(3-phenylphenyl)ethyl (meth)acrylate, 4-(biphenyl-2-yloxy)butyl (meth)acrylate, 3-(biphenyl-2-yloxy)butyl (meth)acrylate, 2-(biphenyl-2-yloxy)butyl (meth)acrylate, 1-(biphenyl-2-yloxy)butyl (meth)acrylate, 4-(biphenyl-2-yloxy)propyl (meth)acrylate, 3-(biphenyl-2-yloxy)propyl (meth)acrylate, 2-(biphenyl-2-yloxy)propyl (meth)acrylate, 1-(biphenyl-2-yloxy)propyl (meth)acrylate, 4-(biphenyl-2-yloxy)ethyl (meth)acrylate, 3-(biphenyl-2-yloxy)ethyl (meth)acrylate, 2-(biphenyl-2-yloxy)ethyl (meth)acrylate, 1-(biphenyl-2-yloxy)ethyl (meth)acrylate, 2-(4-benzylphenyl)ethyl (meth)acrylate, 1-(4-benzylphenyl)ethyl (meth)acrylate, or one or more of these structural isomers.

[0063] The non-silicone-based photocurable polyfunctional monomer is a difunctional to decafunctional (meth)acrylate. Specifically, it can include di(meth)acrylate having a substituted or unsubstituted linear or branched alkylene group with 1 to 20 carbon atoms, and tri(meth)acrylate, tetra(meth)acrylate, penta(meth)acrylate, or hexa(meth)acrylate of a triol, tetrol, pentol, or hexol with 3 to 20 carbon atoms, which can be substituted or unsubstituted. For example, the di(meth)acrylate can include one or more of hexanediol di(meth)acrylate, heptanediol di(meth)acrylate, octanediol di(meth)acrylate, nonanediol di(meth)acrylate, decanediol di(meth)acrylate, undecanediol di(meth)acrylate, and dodecanediol di(meth)acrylate. The tri(meth)acrylate can include tri(meth)acrylate of a triol, tetrol, pentol, or hexol with 3 - 20 carbon atoms, such as trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol tri(meth)acrylate, tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, etc. The tetra(meth)acrylate can include tetra(meth)acrylate of a tetrol, pentol, or hexol with 4 - 20 carbon atoms, such as pentaerythritol tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, etc. The penta(meth)acrylate can further include penta(meth)acrylate of a pentol or hexol with 4 - 20 carbon atoms, such as dipentaerythritol penta(meth)acrylate. The hexa(meth)acrylate can include hexa(meth)acrylate of a hexol with 4 - 20 carbon atoms, such as dipentaerythritol hexa(meth)acrylate.

[0064] The total amount of non-silicone-based photocurable monomers, preferably non-silicone-based monofunctional photocurable monomers, is 10 to 70 parts by weight, specifically 10 parts by weight, 11 parts by weight, 12 parts by weight, 13 parts by weight, 14 parts by weight, 15 parts by weight, 16 parts by weight, 17 parts by weight, 18 parts by weight, 19 parts by weight, 20 parts by weight, 21 parts by weight, 22 parts by weight, 23 parts by weight, 24 parts by weight, 25 parts by weight, 26 parts by weight, 27 parts by weight, 28 parts by weight, 29 parts by weight, 30 parts by weight, 31 parts by weight, 32 parts by weight, 33 parts by weight, 34 parts by weight, 35 parts by weight, 36 parts by weight, 37 parts by weight, 38 parts by weight, 39 parts by weight, 40 parts by weight, 41 parts by weight, 42 parts by weight, 43 parts by weight, 44 parts by weight, 45 parts by weight, 46 parts by weight, 47 parts by weight, 48 parts by weight, 49 parts by weight, 50 parts by weight, 51 parts by weight, 52 parts by weight, 53 parts by weight, 54 parts by weight, 55 parts by weight, 56 parts by weight, 57 parts by weight, 58 parts by weight, 59 parts by weight, 60 parts by weight, 61 parts by weight, 62 parts by weight, 63 parts by weight, 64 parts by weight, 65 parts by weight, 66 parts by weight, 67 parts by weight, 68 parts by weight, 69 parts by weight, 70 parts by weight, specifically 20 to 60 parts by weight, and more specifically 30 to 60 parts by weight out of 100 parts by weight of the total amount of photocurable monomers. Within the above range, there may be an effect of reducing the viscosity of the composition and increasing the adhesive strength.

[0065] (B2) The silicone-based photocurable monomer may be non-aromatic or aromatic.

[0066] (B2) The silicone-based photocurable monomer may have one or more photocurable functional groups, for example, (meth)acrylate groups, and may be a monomer having silicone. The silicone-based photocurable monomer may contain one or more of a silicone-based photocurable monofunctional monomer and a silicone-based photocurable polyfunctional monomer, preferably a silicone-based photocurable monofunctional monomer, and more preferably a non-aromatic silicone-based photocurable monofunctional monomer.

[0067] The silicone-based photocurable monofunctional monomer may be one or more of silsesquioxane derivatives and siloxane-based derivatives. The siloxane-based derivative, unlike the silsesquioxane derivative, means not having a partial cage or ladder structure.

[0068] The silsesquioxane derivative may have a partial cage structure, a ladder structure, a random structure, etc., but preferably, the POSS (polyhedral oligomeric silsesquioxane) structure of the following Chemical Formula 4 may be preferred.

[0069] [Chemical Formula] Chemical Formula 4

[0070] (In the above Chemical Formula 4, any one of the Rs is the following Chemical Formula 5.)

[0071] [Chemical Formula] Chemical Formula 5

[0072] (In the above Chemical Formula 5, * is the bonding site to the silicone, R1 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, R2 is hydrogen or a methyl group, and the remaining Rs are substituted or unsubstituted, linear or branched alkyl groups having 1 to 20 carbon atoms.)

[0073] For example, in Chemical Formula 4, the remaining Rs may be one or more of substituted or unsubstituted, linear or branched alkyl groups having 4 to 20 carbon atoms, such as isobutyl group, isooctyl group, and 2,4,4-trimethylpentyl group.

[0074] For example, the silicone-based photocurable monofunctional monomer can contain one or more of the following chemical formulas 4-1 and 4-2.

[0075] [Chemical formula] Chemical formula 4-1

[0076] TIFF2025520643000021.tif74168

[0077] [Chemical formula] Chemical formula 4-2

[0078] TIFF2025520643000023.tif73168

[0079] The silsesquioxane derivative may be contained in an amount of 1 to 40 parts by weight, specifically, 1 part by weight, 2 parts by weight, 3 parts by weight, 4 parts by weight, 5 parts by weight, 6 parts by weight, 7 parts by weight, 8 parts by weight, 9 parts by weight, 10 parts by weight, 11 parts by weight, 12 parts by weight, 13 parts by weight, 14 parts by weight, 15 parts by weight, 16 parts by weight, 17 parts by weight, 18 parts by weight, 19 parts by weight, 20 parts by weight, 21 parts by weight, 22 parts by weight, 23 parts by weight, 24 parts by weight, 25 parts by weight, 26 parts by weight, 27 parts by weight, 28 parts by weight, 29 parts by weight, 30 parts by weight, 31 parts by weight, 32 parts by weight, 33 parts by weight, 34 parts by weight, 35 parts by weight, 36 parts by weight, 37 parts by weight, 38 parts by weight, 39 parts by weight, 40 parts by weight, specifically, 1 to 30 parts by weight, 5 to 20 parts by weight, and more specifically, 5 to 15 parts by weight out of 100 parts by weight in total of the (B) photocurable monomer. Within the above range, there may be an effect of reducing the viscosity of the composition and increasing the adhesive strength.

[0080] The siloxane-based derivative can be represented by the following chemical formula 6.

[0081] [Chemical formula 6] (R3)(R4)(R5)Si-R1-O-C(=O)-CR2=CH2 (In the chemical formula 6, R1 is a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms, R2 is hydrogen or a methyl group, R3, R4, and R5 are each independently a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 10 carbon atoms, or *-(-O-Si(R6)(R7)-) n -R8 (* is the bonding site of the element, R6, R7, and R8 are each independently a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, and n is an integer from 1 to 10).)

[0082] Preferably, at least one of R3, R4, and R5 may be *-(-O-Si(R6)(R7)-) n -R8. More preferably, R3, R4, and R5 may all be *-(-O-Si(R6)(R7)-) n -R8.

[0083] The siloxane-based derivative may be contained in an amount of 10 to 50 parts by weight, for example, 10 parts by weight, 11 parts by weight, 12 parts by weight, 13 parts by weight, 14 parts by weight, 15 parts by weight, 16 parts by weight, 17 parts by weight, 18 parts by weight, 19 parts by weight, 20 parts by weight, 21 parts by weight, 22 parts by weight, 23 parts by weight, 24 parts by weight, 25 parts by weight, 26 parts by weight, 27 parts by weight, 28 parts by weight, 29 parts by weight, 30 parts by weight, 31 parts by weight, 32 parts by weight, 33 parts by weight, 34 parts by weight, 35 parts by weight, 36 parts by weight, 37 parts by weight, 38 parts by weight, 39 parts by weight, 40 parts by weight, 41 parts by weight, 42 parts by weight, 43 parts by weight, 44 parts by weight, 45 parts by weight, 46 parts by weight, 47 parts by weight, 48 parts by weight, 49 parts by weight, 50 parts by weight, specifically 10 to 40 parts by weight, and more specifically 20 to 40 parts by weight, out of 100 parts by weight in total of the (B) photocurable monomer. Within the above range, there may be an effect of reducing the viscosity of the composition and increasing the adhesive strength.

[0084] The silicone-based photocurable polyfunctional monomer is a monomer having silicone, particularly a monomer having a siloxane group (*-Si-O-Si-*), and the photocurable functional group may be bonded to both ends or side chains of the monomer.

[0085] In one specific example, the silicone-based photocurable polyfunctional monomer can be represented by the following Chemical Formula 7.

[0086]

Chemical Formula

[0087] (In the above Chemical Formula 7, R1, R2, R3, R4, and R5 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl ether group having 1 to 30 carbon atoms, *-N(R’)(R’’) (where * is the connecting site of the element, and R’ and R’’ are the same or different and are hydrogen or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms), a substituted or unsubstituted alkyl sulfide group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms. Y1, Y2, and Y3 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monoalkylsilyloxy group having 1 to 10 carbon atoms, a substituted or unsubstituted dialkylsilyloxy group having 1 to 10 carbon atoms, a substituted or unsubstituted trialkylsilyloxy group having 1 to 10 carbon atoms, or the following Chemical Formula 8.

[0088]

Chemical Formula

[0089] (In the above Chemical Formula 8, * is the connecting site of the element, R6 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, R7 is a hydrogen or methyl group.) n is from 0 to 20, m is from 0 to 20, and n + m is greater than 0, Two or more of Y1, Y2, and Y3 are the above Chemical Formula 8, or n is from 2 to 20.)

[0090] Among the above Chemical Formula 7, in a substituted or unsubstituted monoalkylsilyloxy group having 1 to 10 carbon atoms, the 1 to 10 carbon atoms mean the number of carbon atoms contained in one alkyl group. Among the above Chemical Formula 7, in a substituted or unsubstituted dialkylsilyloxy group having 1 to 10 carbon atoms, the 1 to 10 carbon atoms mean the number of carbon atoms contained in each of one alkyl group. Among the above Chemical Formula 7, in a substituted or unsubstituted trialkylsilyloxy group having 1 to 10 carbon atoms, the 1 to 10 carbon atoms mean the number of carbon atoms contained in each of one alkyl group.

[0091] Preferably, R1, R2, R3, R4, and R5 may each independently be a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

[0092] Preferably, R6 may be a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms and a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms.

[0093] In the above Chemical Formula 7, n and m are each an average value or an integer, and may be from 0 to 10 and from 0 to 5.

[0094] The silicone-based photocurable monomer may be a commercially available product or may be produced by a conventional method known to those skilled in the art.

[0095] The total amount of silicone-based photocurable monomers, preferably the total amount of silicone-based monofunctional photocurable monomers, is 30 to 90 parts by weight, for example, 30 parts by weight, 31 parts by weight, 32 parts by weight, 33 parts by weight, 34 parts by weight, 35 parts by weight, 36 parts by weight, 37 parts by weight, 38 parts by weight, 39 parts by weight, 40 parts by weight, 41 parts by weight, 42 parts by weight, 43 parts by weight, 44 parts by weight, 45 parts by weight, 46 parts by weight, 47 parts by weight, 48 parts by weight, 49 parts by weight, 50 parts by weight, 51 parts by weight, 52 parts by weight, 53 parts by weight, 54 parts by weight, 55 parts by weight, 56 parts by weight, 57 parts by weight, 58 parts by weight, 59 parts by weight, 60 parts by weight, 61 parts by weight, 62 parts by weight, 63 parts by weight, 64 parts by weight, 65 parts by weight, 66 parts by weight, 67 parts by weight, 68 parts by weight, 69 parts by weight, 70 parts by weight, 71 parts by weight, 72 parts by weight, 73 parts by weight, 74 parts by weight, 75 parts by weight, 76 parts by weight, 77 parts by weight, 78 parts by weight, 79 parts by weight, 80 parts by weight, 81 parts by weight, 82 parts by weight, 83 parts by weight, 84 parts by weight, 85 parts by weight, 86 parts by weight, 87 parts by weight, 88 parts by weight, 89 parts by weight, 90 parts by weight, specifically 40 to 80 parts by weight, and more specifically 40 to 70 parts by weight, out of 100 parts by weight of the total amount of photocurable monomers. Within the above range, there may be an effect of reducing the viscosity of the composition and increasing the adhesive strength.

[0096] In one specific example, the total amount of the non-silicone-based monofunctional photocurable monomer and the silicone-based monofunctional photocurable monomer may preferably be 95 parts by weight or more, preferably 100 parts by weight, out of 100 parts by weight of the total amount of the silicone-based photocurable monomers.

[0097] In one specific example, the total of (A) and (B) may be 95 parts by weight or more, preferably 100 parts by weight, out of 100 parts by weight of the total amount of all photocurable monomers contained in the composition.

[0098] Photoinitiator The photoinitiator can include, without limitation, ordinary photoinitiators capable of performing a photocuring reaction. For example, the photoinitiator can include triazine-based, acetophenone-based, benzophenone-based, thioxanthone-based, benzoin-based, phosphorus-based, oxime-based, or mixtures thereof.

[0099] Preferably, the photoinitiator can include a phosphorus-based initiator having a maximum absorption wavelength of 360 nm to 400 nm. When the phosphorus-based initiator is used, in the composition of the present invention, better initiation performance can be exhibited at a long-wavelength UV (e.g., 300 nm to 400 nm). Examples of the phosphorus-based initiator may include diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphinate, or mixtures thereof. For example, the initiator may be included alone or in a mixture of two or more. The "maximum absorption wavelength" may be a value measured by a conventional method known to those skilled in the art or obtained with reference to a product catalog.

[0100] The photoinitiator may be included in an amount of 1 part by weight to 10 parts by weight, preferably 1 part by weight to 5 parts by weight, based on 100 parts by weight of the total of (B) the photocurable monomers. Within the above range, the photocuring rate of the composition can be increased, and it is possible to prevent the light transmittance from decreasing due to the remaining amount of the initiator.

[0101] The composition of the present invention may be formed by mixing (A) one or more indole group-containing and silicone-containing photocurable monomers, (B) photocurable monomers, and (C) a photopolymerization initiator. For example, the composition of the present invention can be formed in a solvent-free type without containing a solvent.

[0102] The composition of the present invention is a photocurable composition, and can be photocured by irradiation at 10 mW / cm 2 to 500 mW / cm 2 for 1 second to 50 seconds at a UV wavelength to form a sealing layer.

[0103] The composition of the present invention may further contain ordinary additives known to those skilled in the art. The additives may include, but are not limited to, heat stabilizers, antioxidants, UV absorbers, and the like.

[0104] The composition of the present invention may have a viscosity of 7 cps to 100 cps, preferably 7 cps to 60 cps, and more preferably 7 cps to 50 cps at 25 ± 2 °C (23 °C to 27 °C). Within the above range, the inkjetting property of the encapsulating composition can be excellent.

[0105] The composition of the present invention may have a photocuring rate of 89% to 100%, preferably 91% to 99%. Within the above range, the composition of the present invention can function as an organic layer. The photocuring rate may be calculated from the following formula 1.

[0106] The composition of the present invention may be used to encapsulate an organic light-emitting device. Specifically, the composition can form an organic layer in an encapsulation structure in which an inorganic layer and an organic layer are sequentially formed.

[0107] The composition of the present invention can also be used as a member for an apparatus, particularly a member for a display apparatus, for encapsulating a member for an apparatus that may be decomposed or deteriorated by permeation of a gas or liquid in the surrounding environment, such as oxygen and / or moisture and / or water vapor in the air and / or a chemical substance used in the processing of an electronic product. For example, the member for an apparatus may be, but is not limited to, a lighting device, a metal sensor pad, a microdisk laser, an electrochromic device, a photochromic device, a microelectromechanical system, a solar cell, an integrated circuit, a charge-coupled device, a light-emitting polymer, and the like.

[0108] The organic light-emitting device display of the present invention may include an organic layer formed of the composition for encapsulating an organic light-emitting device according to an embodiment of the present invention. Specifically, the organic light-emitting device display includes an organic light-emitting device and a barrier stack formed on the organic light-emitting device and including an inorganic layer and an organic layer, and the organic layer may be formed of the composition for encapsulating an organic light-emitting device according to an embodiment of the present invention. As a result, the reliability of the organic light-emitting device display can be improved.

[0109] Hereinafter, with reference to FIG. 1, an organic light-emitting element display device according to an embodiment of the present invention will be described. FIG. 1 is a cross-sectional view of an organic light-emitting element display device according to an embodiment of the present invention.

[0110] Referring to FIG. 1, the organic light-emitting element display device 100 includes a substrate 10, an organic light-emitting element 20 formed on the substrate 10, and a barrier stack 30 formed on the organic light-emitting element 20 and including an inorganic layer 31 and an organic layer 32. The inorganic layer 31 is in contact with the organic light-emitting element 20, and the organic layer 32 may be formed of the composition for encapsulating an organic light-emitting element according to an embodiment of the present invention.

[0111] The substrate 10 is not particularly limited as long as it is a substrate on which an organic light-emitting element can be formed. For example, it may be made of a material such as transparent glass, a plastic sheet, silicone, or a metal substrate.

[0112] The organic light-emitting element 20 is one commonly used in an organic light-emitting element display device. Although not shown in FIG. 1, it includes a first electrode, a second electrode, and an organic light-emitting film formed between the first electrode and the second electrode. The organic light-emitting film may be one in which a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer are sequentially laminated, but is not limited thereto.

[0113] The barrier stack 30 includes an organic layer and an inorganic layer. Since the components constituting each layer are different from each other, each can embody an organic light-emitting element encapsulation function.

[0114] By having components different from those of the organic layer, the inorganic layer can complement the effects of the organic layer. For example, the inorganic layer may be made of a metal, a non-metal, an intermetallic compound or alloy, a non-intermetallic compound or alloy, an oxide of a metal or non-metal, a fluoride of a metal or non-metal, a nitride of a metal or non-metal, a carbide of a metal or non-metal, an oxynitride of a metal or non-metal, a boride of a metal or non-metal, an oxyboride of a metal or non-metal, a silicide of a metal or non-metal, or a mixture thereof. The metal or non-metal may be, but is not limited to, silicone (Si), aluminum (Al), selenium (Se), zinc (Zn), antimony (Sb), indium (In), germanium (Ge), tin (Sn), bismuth (Bi), transition metals, lanthanide metals, etc. Specifically, the inorganic layer may be AlOx including silicon oxide (SiOx), silicon nitride (SiNx), silicon oxynitride (SiOxNy), ZnSe, ZnO, Sb2O3, Al2O3, etc., In2O3, SnO2.

[0115] The inorganic layer may be deposited by a plasma process, a vacuum process, for example, sputtering, chemical vapor deposition, plasma chemical vapor deposition, evaporation, sublimation, electron cyclotron resonance - plasma vapor deposition, and combinations thereof.

[0116] When the organic layer is deposited alternately with the inorganic layer, it can ensure the smoothing characteristics of the inorganic layer and prevent defects of the inorganic layer from being further propagated to other inorganic layers.

[0117] The organic layer may be formed by a combination such as coating, deposition, and curing of the composition for encapsulating an organic light-emitting device according to an embodiment of the present invention. For example, the composition for encapsulating an organic light-emitting device is coated with a thickness of 1 μm to 50 μm and irradiated with 10 mW / cm 2 to 500 mW / cm 2 for 1 second to 50 seconds to be cured.

[0118] The barrier stack includes an organic layer and an inorganic layer, and the total number of the organic layer and the inorganic layer is not limited. The total number of the organic layer and the inorganic layer can be changed according to the level of the permeation resistance to oxygen and / or moisture and / or water vapor and / or chemicals. For example, the total number of the organic layer and the inorganic layer may be 10 layers or less, for example, 2 to 7 layers, and specifically, it may be formed of 7 layers in the order of inorganic layer / organic layer / inorganic layer / organic layer / inorganic layer / organic layer / inorganic layer.

[0119] In the barrier stack, the organic layer and the inorganic layer may be alternately vapor-deposited. This is because of the effect on the organic layer generated by the physical properties of the above-described composition. Thereby, the organic layer and the inorganic layer can complement or enhance the sealing effect on the device.

[0120] Hereinafter, with reference to FIG. 2, an organic light-emitting element display device according to another embodiment of the present invention will be described. FIG. 2 is a cross-sectional view of an organic light-emitting element display device according to another embodiment of the present invention.

[0121] Referring to FIG. 2, the organic light-emitting element display device 200 includes a substrate 10, an organic light-emitting element 20 formed on the substrate 10, and a barrier stack 30 formed on the organic light-emitting element 20 and including an inorganic layer 31 and an organic layer 32. The inorganic layer 31 seals an internal space 40 in which the organic light-emitting element 20 is accommodated, and the organic layer 32 may be formed of the composition for sealing an organic light-emitting element according to an embodiment of the present invention. The organic light-emitting element display device according to another embodiment of the present invention is substantially the same as the organic light-emitting element display device according to an embodiment of the present invention except that the inorganic layer does not contact the organic light-emitting element.

Example

[0122] Hereinafter, the configuration and operation of the present invention will be described in more detail through preferred embodiments of the present invention. However, this is presented as a preferred exemplification of the present invention, and in no way should it be construed that the present invention is limited thereby.

[0123] Example 1 (1) Production of one or more indole groups and silicone-containing photocurable monomers

[0124] <Reaction formula 1>

Chemical formula

[0125] (In the above Reaction formula 1, Me represents a methyl group.)

[0126] Sodium iodide (NaI) (8.0 equivalents) was added to a solution (0.2 M) of the above Compound 1 (1.0 equivalent) dissolved in acetone, and the mixture was refluxed for 18 hours. After the obtained reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure. After adding distilled water and redissolving, the aqueous layer was extracted with dichloromethane. The obtained dichloromethane layer was washed again with distilled water and then passed through MgSO4. It was concentrated under reduced pressure to obtain Compound 2. This compound was used in the next reaction without additional purification.

[0127] Cyanoacetic acid (1 equivalent) was slowly added to a mixture of sodium hydride (NaH) (1.2 equivalents) and N,N-dimethylformamide at 0 °C. After stirring at the same temperature for 1 hour, a solution of Compound 2 (3.0 equivalents) dissolved in N,N-dimethylformamide was added. After the temperature was raised to 50 °C, the mixture was reacted overnight. After adding distilled water for dilution, it was extracted with ethyl acetate. The organic layer was washed with distilled water, passed through MgSO4, and concentrated. Compound 3 could be obtained using column chromatography (developing solution: hexane / ethyl acetate) (yield 60%). The 1 1H NMR analysis results of the above Compound 3 are as follows. 1 1H NMR (300 MHz, CDCl3, ppm): 3.90 (2H, s), 3.45 (2H, s), 1.99 (2H, s), 0.26 (6H, s), 0.22 (6H, s).

[0128] <Reaction formula 2>

Chemical formula

[0129] (In the reaction formula 2, Me is a methyl group.)

[0130] Sodium methacrylate (1.2 equivalents) and BHT (butylated hydroxytoluene) (0.4 mol%) were added to a solution (0.25 M) of the compound 3 (1 equivalent) dissolved in N,N-dimethylformamide, and the mixture was stirred at 50 °C overnight. After dilution with distilled water, extraction was performed with ethyl acetate. The organic layer was washed with distilled water and then passed through MgSO4. After concentration under reduced pressure, compound 4 was obtained through column chromatography (developing solution: hexane / ethyl acetate) (yield: 23%). The 1 1H NMR analysis results of the compound 4 are as follows. 1 1H NMR (300 MHz, CDCl3, ppm): 6.07 (1H, m), 5.54 (1H, m), 3.85 (2H, s), 3.79 (2H, s), 3.46 (2H, s), 1.94 (3H, m), 0.17 (12H, s).

[0131] <Reaction formula 3>

Chemical formula

[0132] (In the reaction formula 3, Me is a methyl group.)

[0133] A solution (0.2 M) of the compound 5 (1.0 equivalent) and sodium hydride (NaH) (1.5 equivalents) dissolved in N,N-dimethylformamide was stirred at 0 °C for 30 minutes, and then methyl iodide (MeI) (2 equivalents) was added. The solution was stirred overnight at room temperature. After dilution with distilled water, extraction was performed with ethyl acetate. The organic layer was washed again with distilled water and passed through MgSO4. After concentration under reduced pressure, compound 6 was obtained (yield: 89%). The 1 1H NMR analysis results of the compound 6 are as follows. 11H NMR (300 MHz, (CD3)2SO, ppm): 9.61 (1H, s), 8.23 (1H, m), 7.64 (6H, m), 7.37 (2H, m), 3.70 (3H, s).

[0134] <Reaction Scheme 4> [Chemical formula]

[0135] (In the above Reaction Scheme 4, Me represents a methyl group.)

[0136] Piperidine (2.0 equivalents) and BHT (0.4 mol%) were added to a solution (1.0 M) of the compound 4 (1.5 equivalents) and the compound 6 (1.0 equivalent) dissolved in pyridine, and the mixture was stirred at room temperature for 100 minutes. After removing the solvent by distillation under reduced pressure, the residue was redissolved in ethyl acetate. The organic layer was washed with 0.1 N HCl(aq) and passed through MgSO4. After concentration under reduced pressure, the substance corresponding to the chemical formula 1-1 was obtained by column chromatography (developing solvent: hexane / ethyl acetate) (yield: 56%). The 1H NMR analysis results of the chemical formula 1-1 are as follows. 1 The 1H NMR analysis results are as follows. 1 1H NMR (300 MHz, CDCl3, ppm): 8.26 (1H, m), 7.93 (1H, s), 7.38 (3H, m), 7.21 (5H, m), 5.89 (1H, m), 5.34 (1H, m), 3.68 (2H, s), 3.61 (2H, s), 3.53 (3H, s), 0.19 (12H, m).

[0137] (2) Preparation of the composition 4 parts by weight of the produced compound of Chemical Formula 1-1, 58 parts by weight of tridecyl methacrylate (Aldrich) as a photocurable monomer, 30 parts by weight of a silicone-based photocurable monomer (monofunctional monomer, SM-2, Chemical Formula 9 below), 10 parts by weight of methacryloyloctyl POSS (MA0719, Hybrid Plastics, Chemical Formula 10 below) which is a monofunctional monomer as a silicone-based photocurable monomer, 2 parts by weight of MAC-SQSI-20 (Toagosei, Chemical Formula 11 below) which is a monofunctional monomer as a silicone-based photocurable monomer, and 3 parts by weight of Irgacure TPO as a photoinitiator were placed in a 125 ml brown polypropylene bottle and mixed at room temperature for 3 hours using a shaker to produce a sealing composition.

[0138]

Chem.

[0139]

Chem.

[0140] TIFF2025520643000032.tif37168

[0141]

Chem.

[0142] TIFF2025520643000034.tif35168

[0143] Comparative Example 1 58 parts by weight of tridecyl methacrylate (Aldrich) as a photocurable monomer, 30 parts by weight of a silicone-based photocurable monomer (SM-2), 10 parts by weight of methacryloyloctyl POSS (MA0719, Hybrid Plastics), 2 parts by weight of MAC-SQ SI-20 (Toagosei), and 3 parts by weight of Irgacure TPO as a photopolymerization initiator were placed in a 125 ml brown polypropylene bottle and mixed at room temperature for 3 hours using a shaker to produce a sealing composition.

[0144] The following physical properties were measured for the compositions produced in the examples and comparative examples, and the results are shown in Table 1.

[0145] (1) Light transmittance (unit: %): The sealing compositions of the examples and comparative examples were applied by spraying on a glass substrate and UV-cured by UV irradiation at 100 mW / cm 2 for 20 seconds to form an organic layer with a thickness of 10 μm. The light transmittance of the obtained organic layer at a wavelength of 405 nm was measured using Lambda 950 (Perkin Elmer).

[0146] (2) Solution stability: In the examples, while continuously adding the compound of Chemical Formula 1-1 to the mixture of the photocurable monomer and the photopolymerization initiator while increasing the amount of the compound of Chemical Formula 1-1, the content of the compound of Chemical Formula 1-1 added until the compound of Chemical Formula 1-1 was not precipitated when observed with the naked eye was measured.

[0147] (3) Storage stability: While storing the sealing compositions of the examples and comparative examples at room temperature (25 °C) for a predetermined time, the precipitation of the compound of Chemical Formula 1-1 was confirmed with the naked eye. More precisely, the change over time in the light transmittance at a wavelength of 405 nm was measured using the above light transmittance measurement method. The storage stability was determined by the maximum period during which no change in light transmittance was observed.

[0148] (4) Dielectric constant (unit: none): The sealing compositions of the examples and comparative examples were applied to a chromium (Cr) plate with a predetermined thickness and irradiated with 100 mW / cm 2A coating film with a thickness of 8 μm was formed by subjecting it to UV irradiation for 10 seconds for photocuring. After depositing an aluminum electrode (electrode for measuring the dielectric constant) on the said coating film, the dielectric constant was measured at a frequency of 200 kHz and a temperature of 25 °C using an impedance measuring machine (E4990A, Impedance Analyzer).

[0149] (5) Viscosity (unit: cps): For the encapsulation compositions of the examples and comparative examples, the viscosity was measured at 24.8 °C using a viscosity measuring machine LVDV-II Pro (manufactured by Brookfield) with a spindle number (No. spindle) of 40.

[0150] (6) Photocuring rate (unit: %): For the encapsulation composition, the absorption peak intensities around 1635 cm -1 (C=C) and around 1720 cm -1 (C=O) were measured. The encapsulation composition was spray-coated on a glass substrate and irradiated at 100 mW / cm 2 for 20 seconds for UV curing to obtain a test piece of 20 cm × 20 cm × 3 μm (width × length × thickness). The cured film was separated, and the absorption peak intensities around 1635 cm -1 (C=C) and around 1720 cm -1 (C=O) were measured. The photocuring rate was calculated by the following formula 1.

[0151] [Formula 1] Photocuring rate = |1 - (A / B)| × 100 (In the above formula 1, A is the ratio of the absorption peak intensity around 1635 cm -1 to the absorption peak intensity around 1720 cm -1 in the cured film, and B is the ratio of the absorption peak intensity around 1635 cm -1 to the absorption peak intensity around 1720 cm -1 in the encapsulation composition.)

[0152]

Table 1

[0153] As shown in Table 1 above, the composition for encapsulating an organic light-emitting element of the present invention can form an organic layer having a low dielectric constant after curing and a low light transmittance at a wavelength of 420 nm or less.

[0154] Even when containing a UV absorption type photocurable monomer, the solution preparation stability was high, and the storage stability was also high even when stored for a long period of time.

[0155] On the other hand, the composition of Comparative Example 1 without one or more indole group and silicone-containing photocurable monomers of the present invention could not form an organic layer having a low light transmittance at a wavelength of 420 nm or less.

[0156] Simple modifications or changes of the present invention can be easily implemented by those having ordinary knowledge in this field, and any such modifications and changes can be regarded as being included in the scope of the present invention.

Claims

1. (A) One or more indole groups and a silicone-containing photocurable monomer, (B) A photocurable monomer, and (C) A photopolymerization initiator, and is an organic light-emitting element encapsulating composition.

2. The (A) is represented by the following Chemical Formula 1, and the organic light-emitting element encapsulating composition according to Claim 1: 【Chemical 1】 Chemical Formula 1 (In the above Chemical Formula 1, R １ is hydrogen or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, R ２ is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted arylalkyl group having 7 to 20 carbon atoms, R ３ , R ４ , R ５ , R ６ are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, L １ and L ２ are each independently hydrogen, a cyano group (—CN), a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 20 carbon atoms, *—R ７ - epoxy group (* is the bonding site of the element, and R ７ is an alkylene group having 1 to 5 carbon atoms.), or a siloxane group-containing (meth) acrylate group, L １ and L ２ One or more of them are siloxane group-containing (meth) acrylate groups or -R ７ - epoxy groups.).

3. The (A) is represented by any one of the following Chemical Formulas 1-1 to 1-12, and the organic light-emitting element encapsulating composition according to Claim 2: 【Chemical Formula 2】 Chemical Formula 1-1 【Chemical Formula 3】 Chemical Formula 1-2 【Chemical Formula 4】 Chemical Formula 1-3 【Chemical Formula 5】 Chemical Formula 1-4 【Chemical Formula 6】 Chemical Formula 1-5 【Chemical Formula 7】 Chemical Formula 1-6 [Chemical 8] Chemical Formula 1-7 【Chemical Formula 9】 Chemical Formula 1-8 【Chemical Formula 10】 Chemical Formula 1-9 【Chemical 11】 Chemical Formula 1-10 【Chemical 12】 Chemical Formula 1-11 【Chemical 13】 Chemical Formula 1-12 (In the above chemical formulas 1-1 to 1-12, R ９ is hydrogen or a methyl group, Me is a methyl group, and Et is an ethyl group.).

4. The (B) contains one or more of a non-silicone-based photocurable monomer and a silicone-based photocurable monomer, and the organic light-emitting element encapsulating composition according to Claim 1.

5. The non-silicone-based photocurable monomer contains a non-silicone-based photocurable monofunctional monomer, and the organic light-emitting element encapsulating composition according to Claim 4.

6. The non-silicone-based photocurable monofunctional monomer contains a mono(meth)acrylate having a linear or branched alkyl group having 1 to 20 carbon atoms, and the organic light-emitting element encapsulating composition according to Claim 5.

7. The silicone-based photocurable monomer contains one or more of the silicone-based photocurable monofunctional monomer represented by the following Chemical Formula 4 and the silicone-based photocurable monofunctional monomer represented by the following Chemical Formula 6, and the organic light-emitting element encapsulating composition according to Claim 4: 【Chemical 14】 Chemical Formula 4 (In the above Chemical Formula 4, Any one of Rs is represented by the following Chemical Formula 5, 【Chemical Formula 15】 Chemical Formula 5 (In the above Chemical Formula 5, * is a bonding site to silicone, R １ is an alkylene group having 1 to 10 carbon atoms which may be substituted or unsubstituted, R ２ is a hydrogen or methyl group.) The remaining Rs are substituted or unsubstituted, linear or branched alkyl groups having 1 to 20 carbon atoms.) [Chemical Formula 6] (R ３ )(R ４ )(R ５ )Si-R １ -O-C(=O)-CR ２ =CH ２ (In the above Chemical Formula 6, R １ is an alkylene group having 1 to 5 carbon atoms which may be substituted or unsubstituted, R ２ is a hydrogen or methyl group, R ３ 、 R ４ 、 R ５ are each independently a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 10 carbon atoms, or *-( -O-Si(R ６ )(R ７ )) ｎ -R ８ (* is the bonding site of the element, and R ６ , R ７ , R ８ are each independently a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, and n is an integer from 1 to 10.).).

8. The composition is 100 parts by weight of the total of the (B), 0.01 part by weight to 10 parts by weight of the (A) with respect to 100 parts by weight of the total of the (B), and 1 part by weight to 10 parts by weight of the (C) with respect to 100 parts by weight of the total of the (B), and is the organic light-emitting element encapsulating composition according to Claim 1.

9. An organic light-emitting element display device including an organic layer formed of the organic light-emitting element encapsulating composition according to any one of Claims 1 to 8.

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