Encapsulating composition for organic light-emitting element and organic light-emitting element display device including organic layer formed therefrom
By using photocurable monomers containing indolyl and silicon, combined with photocurable monomers and photopolymerizable initiators, an organic layer with low dielectric constant and low light transmittance is formed, which solves the problem of easy damage to the organic light emitting device in the external environment, and improves its stability and screen quality.
Patent Information
- Application Number
- CN202380061524.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2022-06-24
- Filing Date
- 2023-06-21
- Publication Date
- 2025-04-04
AI Technical Summary
The existing organic light emitting devices are prone to damage when in contact with external moisture or oxygen, and the stability and light transmittance of the encapsulation layer are insufficient, which affects its reliability and screen quality.
An organic layer with a low dielectric constant and low light transmittance is formed using a photocurable monomer containing at least one indolyl and silicon, combined with a photocurable monomer and a photopolymerizable initiator.
It ensures high solution preparation stability and storage stability, and the formed organic layer has low light transmittance at a wavelength of 420 nm or less, which improves the reliability and screen quality of the organic light emitting display device.
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Figure CN119768444A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to a composition for encapsulating an organic light-emitting device and an organic light-emitting display device including an organic layer formed therefrom. Background Art
[0002] The organic light-emitting device is easily damaged and suffers from reliability degradation due to loss of its function when in contact with external moisture or oxygen. Therefore, the organic light-emitting device must be encapsulated by an encapsulation layer including an inorganic layer and an organic layer formed of a composition for encapsulating the organic light-emitting device.
[0003] The encapsulation layer may have a structure in which an organic layer and an inorganic layer are repeatedly formed. For example, the encapsulation layer is formed by repeatedly forming an organic layer and an inorganic layer on an organic light-emitting device, for example, in the order of an organic layer-inorganic layer-organic layer-inorganic layer, etc. Unlike the organic layer, the inorganic layer may be formed of an inorganic material. In general, the inorganic layer may be formed by a plasma method, a vacuum method (such as sputtering), chemical vapor deposition, plasma chemical vapor deposition, evaporation, sublimation, electron cyclotron resonance vapor deposition, and a combination thereof.
[0004] The background art of the present invention is disclosed in Korean Patent Publication No. 10-2016-0150255 and the like. Summary of the invention
[0005] Technical issues
[0006] One aspect of the present invention is to provide a composition for encapsulating an organic light-emitting device, which can ensure high solution preparation stability even when a UV absorbing photocurable monomer is used, and which can ensure high storage stability even when stored for a long period of time.
[0007] Another aspect of the present invention provides a composition for encapsulating an organic light-emitting device, which can form an organic layer having a low dielectric constant and low light transmittance at a wavelength of 420 nm or less after curing even using a UV absorbing photocurable monomer.
[0008] Technical Solution
[0009] One aspect of the present invention relates to a composition for encapsulating an organic light-emitting device.
[0010] The composition for encapsulating an organic light-emitting device includes a photocurable monomer containing at least one indole group and silicon, a photocurable monomer, and a photopolymerizable initiator.
[0011] Another aspect of the present invention relates to an organic light-emitting display device including an organic layer formed of the composition for encapsulating an organic light-emitting device according to the present invention.
[0012] Beneficial Effects
[0013] The present invention provides a composition for encapsulating an organic light-emitting device, which can ensure high solution preparation stability even when a UV absorbing photocurable monomer is used, and which can ensure high storage stability even when stored for a long period of time.
[0014] The present invention provides a composition for encapsulating an organic light-emitting device, which can form an organic layer having a low dielectric constant and low light transmittance at a wavelength of 420 nm or less after curing even if a UV absorbing photocurable monomer is used. BRIEF DESCRIPTION OF THE DRAWINGS
[0015] Figure 1 is a cross-sectional view of an organic light emitting display device according to one embodiment of the present invention.
[0016] Figure 2 is a cross-sectional view of an organic light emitting display device according to another embodiment of the present invention. DETAILED DESCRIPTION
[0017] Embodiments of the present invention will be described in detail with reference to the accompanying drawings to provide a thorough understanding of the present invention to those skilled in the art. It should be understood that the present invention can be embodied in different ways and is not limited to the following embodiments. In the accompanying drawings, for the sake of clarity, parts not related to the description will be omitted, and the same components will be represented by the same reference numerals throughout the specification. Although the length, thickness or width of each component can be magnified in the drawings for understanding, the present invention is not limited thereto.
[0018] The terms used herein are for the purpose of describing exemplary embodiments and are not intended to be limiting of the present invention.As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0019] As used herein, "(meth)acryl" may refer to "acryl" and / or "methacryl".
[0020] As used herein, unless otherwise indicated, "substituted" means that at least one hydrogen atom of a functional group is replaced by a halogen (e.g., F, Cl, Br, or I), a hydroxyl, a nitro, a cyano, an imino (=NH, =NR, R is C1 to C 10 alkyl), amino (-NH2, -NH(R'), -N(R") (R''), R', R" and R'' are each independently C1 to C 10 alkyl), carboxamidino, hydrazine or hydrazone, carboxyl, C1 to C20 Alkyl, C6 to C 30 Aryl, C3 to C 30 Cycloalkyl, C3 to C 30 Heteroaryl or C2 to C 30 Heterocycloalkyl.
[0021] As used herein to indicate a specific numerical range, “X to Y” means “greater than or equal to X and less than or equal to Y (X≤ and ≤Y)”.
[0022] A composition for encapsulating an organic light-emitting device (hereinafter referred to as a "composition") according to one embodiment of the present invention can ensure high solution preparation stability even when a UV-absorbing photocurable monomer is used, and can ensure 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.
[0023] Herein, “high solution preparation stability of UV absorbing photocurable monomers” means that the UV absorbing photocurable monomers have high solubility, and therefore, even if the UV absorbing photocurable monomers are used, there is no precipitation and / or aggregation of the UV absorbing photocurable monomers in the composition. A composition having high solution preparation stability means that, even when the composition contains UV absorbing photocurable monomers, there is no sedimentation, precipitation and / or aggregation of the monomers, thereby ensuring excellent coatability of the composition, and the composition can form an organic layer having a uniform thickness and good light transmittance in the visible spectrum after curing, thereby improving the screen quality of the display device. The high solution preparation stability of the composition can be determined by the method described below in the experimental examples.
[0024] Herein, "high storage stability" means that when the composition containing the UV absorbing photocurable monomer is placed at room temperature (e.g., 25° C.) for one week or longer, there is no sedimentation, precipitation and / or aggregation of the UV absorbing photocurable monomer. A composition with high storage stability can be advantageously used as a composition for forming an organic layer over a long period of time after preparing the composition, thereby ensuring good economic feasibility and processability of the composition. The high storage stability of the composition can be determined by the method described below in the experimental examples.
[0025] The organic layer formed from the composition according to the present invention may have a dielectric constant of 3.2 or less (eg, 1.5 to 3.2). Within this range, the organic layer is not affected by external static electricity or electricity, thereby allowing the performance of the organic light-emitting device to be fully realized.
[0026] The composition according to the present invention comprises: (A) a photocurable monomer containing at least one indole group and silicon, (B) a photocurable monomer, and (C) a photopolymerizable initiator.
[0027] Hereinafter, each component of the composition according to one embodiment of the present invention will be described in detail.
[0028] Photocurable monomer containing at least one indole group and silicon
[0029] The photocurable monomer containing at least one indole group and silicon is a UV absorbing photocurable monomer and can prevent UV damage to the organic light-emitting device by reducing the light transmittance of the organic layer formed after curing the composition at a wavelength of 420 nm or less (e.g., 405 nm to 420 nm). When the organic light-emitting device is irradiated with UV, the organic light-emitting device is damaged and cannot normally perform its inherent functions. In one embodiment, the organic layer may have a light transmittance of 10% or less (e.g., 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% or 10%, specifically, 0% to 10%) at a wavelength of 420nm or less (e.g., 405nm, 406nm, 407nm, 408nm, 409nm, 410nm, 411nm, 412nm, 413nm, 414nm, 415nm, 416nm, 417nm, 418nm, 419nm or 420nm, specifically, 405nm to 420nm).
[0030] Even in combination with a photocurable monomer described below, a photocurable monomer containing at least one indole group and silicon can provide a composition having high solution preparation stability and high storage stability during long-term storage.
[0031] The photocurable monomer containing at least one indole group and silicon may contain an indole group among various functional groups that can absorb light at a wavelength of 420 nm or less, thereby reducing the light transmittance of the organic layer at a wavelength of 420 nm or less when combined with the photocurable monomer described below. The photocurable monomer may contain a (meth)acrylate group or a vinyl group as a photocurable functional group, thereby increasing the photocuring rate when combined with the photocurable monomer (B) described below.
[0032] In combination with the photocurable monomer (B) described below, the photocurable monomer containing at least one indole group and silicon can provide high solution preparation stability and high storage stability without adversely affecting solution preparation stability and storage stability. Preferably, the photocurable monomer has at least one siloxane bond (-Si-O-Si-). The photocurable monomer containing at least one indole group and siloxane can be included in the composition individually or in plural form.
[0033] In one embodiment, the photocurable monomer including at least one indole group and siloxane may be represented by Formula 1.
[0034] [Formula 1]
[0035]
[0036] (In Formula 1,
[0037] R1 is hydrogen or a substituted or unsubstituted C1 to C 10 alkyl,
[0038] R2 is substituted or unsubstituted C6 to C 20 Aryl or substituted or unsubstituted C7 to C 20 Aralkyl,
[0039] R3, R4, R5 and R6 are each independently hydrogen, substituted or unsubstituted C1 to C 10 Alkyl or substituted or unsubstituted C6 to C 20 Aryl, and
[0040] L1 and L2 are each independently hydrogen, cyano (-CN), substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 20 Aryl, substituted or unsubstituted C7 to C 20 Aralkyl, *-R 7 -Epoxy (* is the attachment site of the element, R 7 is a C1 to C5 alkylene group) or a siloxane-containing (meth)acrylate group,
[0041] At least one of L1 and L2 is a siloxane-containing (meth)acrylate group or -R 7 -epoxy).
[0042] In Formula 1, the "siloxane-containing (meth)acrylate group" may be represented by Formula 2:
[0043] [Formula 2]
[0044]
[0045] (In Formula 2,
[0046] * is the attachment site of the element,
[0047] R7 and R8 are each independently a single bond or a substituted or unsubstituted C1 to C 10 Alkylene,
[0048] R9 is hydrogen or methyl,
[0049] X1, X2, X3 and X4 are each independently hydrogen, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 20 Aryl or *-(-O-Si(R 11 )(R 12 )-) p -O-Si(R 13 )(R 14 )(R 15 )(* is the binding site of Si, R 11 , R 12 , R 13 , R 14 and R 15 are independently substituted or unsubstituted C1 to C 10 alkyl, and p is an integer from 0 to 10),
[0050] m is 0 or 1, and
[0051] n is in the range of 1 to 10).
[0052] n can be an integer or an average value.
[0053] In Formula 1, "epoxy" may include
[0054] Preferably, in Formula 1, R1 is hydrogen.
[0055] Preferably, in Formula 1, L1 and L2 are each independently hydrogen, cyano (-CN), substituted or unsubstituted C1 to C 10 An alkyl group or a siloxane-containing (meth)acrylate group, wherein at least one of L1 and L2 is a siloxane-containing (meth)acrylate group.
[0056] Preferably, in Formula 2, R7 and R8 are each independently a single bond or a substituted or unsubstituted C1 to C3 alkylene group, and X1, X2, X3 and X4 are each independently a substituted or unsubstituted C1 to C5 alkyl group or *-(-O-Si(R 11 )(R 12 )-) p -O-Si(R 13 )(R 14 )(R 15 )(* is the binding site of Si, R 11 , R 12 , R 13 , R 14 and R 15 are each independently substituted or unsubstituted C1 to C 10 alkyl, and p is an integer from 0 to 10). Preferably, R 11 , R12 , R 13 , R 14 and R 15 Each is independently a substituted or unsubstituted C1 to C5 alkyl group.
[0057] In one embodiment, the photocurable monomer may be represented by any one of the following Formulae 1-1 to 1-12.
[0058] [Formula 1-1]
[0059]
[0060] [Formula 1-2]
[0061]
[0062] [Formula 1-3]
[0063]
[0064] [Formula 1-4]
[0065]
[0066] [Formula 1-5]
[0067]
[0068] [Formula 1-6]
[0069]
[0070] [Formula 1-7]
[0071]
[0072] [Formula 1-8]
[0073]
[0074] [Formula 1-9]
[0075]
[0076] [Formula 1-10]
[0077]
[0078] [Formula 1-11]
[0079]
[0080] [Formula 1-12]
[0081]
[0082] (In Formulae 1-1 to 1-12, R9 is hydrogen or methyl, Me is methyl, and Et is ethyl.)
[0083] The photocurable monomer containing at least one indole group and silicon may be prepared by a typical method known to those skilled in the art, or may be obtained from a commercially available product.
[0084] The photocurable monomer (A) containing at least one indole group and silicon may be present in an amount of 0.01 to 10 parts by weight (specifically, 0.01, 0.05, 0.1, 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 or 10 parts by weight, preferably 1 to 10 parts by weight, more preferably 1 to 5 parts by weight) relative to 100 parts by weight of the (B) photocurable monomer. Within this range, the composition can reduce light transmittance at a wavelength of 420 nm or less, preferably at a wavelength of 405 nm, thereby preventing damage to the organic light-emitting device by external UV, while improving plasma resistance without deteriorating solution preparation stability and storage stability of the composition.
[0085] Photocurable monomer
[0086] The photocurable monomer (B) is used to form a matrix of the organic layer after curing or to reduce the dielectric constant of the organic layer after curing. The photocurable monomer is different from the photocurable monomer containing at least one indole group and silicon.
[0087] The photocurable monomer may include at least one of (B1) a silicon-free photocurable monomer or (B2) a silicon-based photocurable monomer. Preferably, the photocurable monomer includes a mixture of a silicon-free photocurable monomer and a silicon-based photocurable monomer to increase the photocuring rate and realize an organic layer with a lower dielectric constant.
[0088] The non-silicon-containing photocurable monomer (B1) may contain at least one photocurable functional group, such as a (meth)acrylate group. The non-silicon-containing photocurable monomer may include at least one of a non-silicon-containing photocurable monofunctional monomer or a non-silicon-containing photocurable multifunctional monomer. The non-silicon-containing photocurable monomer may be a non-aromatic monomer or an aromatic monomer, preferably a non-aromatic monomer.
[0089] The silicon-free photocurable monomer may be a non-aromatic monomer and may include a linear or branched C1 to C2 monomer at its ester site. 20For example, the silicon-free photocurable monofunctional monomer may include at least one selected from the group consisting of octyl (meth)acrylate, nonyl (meth)acrylate, lauryl (meth)acrylate, undecyl (meth)acrylate, dodecyl (meth)acrylate, tridecyl (meth)acrylate, tetradecyl (meth)acrylate, tetradecyl (meth)acrylate (including 2-decyltetradecyl (meth)acrylate, etc.), and isostearyl (meth)acrylate.
[0090] The silicon-free photocurable monofunctional monomer may be an aromatic monomer, and may include a compound represented by Formula 3, but is not limited thereto.
[0091] [Formula 3]
[0092]
[0093] (In Formula 3,
[0094] R1 is hydrogen or methyl,
[0095] R2 is substituted or unsubstituted C6 to C 50 Aryl or substituted or unsubstituted C6 to C 50 Aryloxy, and
[0096] s is an integer from 0 to 10).
[0097] Specifically, the compound represented by Formula 3 may include at least one selected from the group consisting of 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-(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-( 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 structural isomers thereof, but are not limited thereto.
[0098] The silicon-free photocurable multifunctional monomer may include a di- to decafunctional (meth)acrylate, specifically, a substituted or unsubstituted linear or branched C1 to C2 20 Alkylene di(meth)acrylate; substituted or unsubstituted C3 to C6 alcohols of triols, tetraols, pentaols or hexaols 20tri(meth)acrylate; tetra(meth)acrylate; penta(meth)acrylate or hexa(meth)acrylate. For example, the di(meth)acrylate may include at least one selected from the group consisting 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 may include a C3 to C4 ester of a triol, a tetraol, a pentaol or a hexaol. 20 Tri(meth)acrylates include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol tri(meth)acrylate, tri(2-hydroxyethyl)isocyanurate tri(meth)acrylate, etc. Tetra(meth)acrylates may include C4 to C6 of tetrahydric alcohol, pentahydric alcohol or hexahydric alcohol. 20 Tetra(meth)acrylates include pentaerythritol tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, etc. Penta(meth)acrylates may include C4 to C6 of pentahydric alcohol or hexahydric alcohol. 20 Penta (meth) acrylates include dipentaerythritol penta (meth) acrylate, etc. Hexa (meth) acrylates may include C4 to C 20 Hexa(meth)acrylates include dipentaerythritol hexa(meth)acrylate and the like.
[0099] The silicon-free photocurable monomer, preferably the silicon-free monofunctional photocurable monomer, may be used in an amount of 10 to 70 parts by weight (specifically, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81 , 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69 or 70 parts by weight, more specifically, 20 parts by weight to 60 parts by weight, more specifically, 30 parts by weight to 60 parts by weight. Within this range, the non-silicon-containing photocurable monomer can reduce the viscosity of the composition while improving its adhesion.
[0100] The silicon-based photocurable monomer (B2) may be a non-aromatic photocurable monomer or an aromatic photocurable monomer.
[0101] The silicon-based photocurable monomer (B2) may contain at least one photocurable functional group (e.g., (meth)acrylate group) and silicon. The silicon-based photocurable monomer may include at least one of a silicon-based photocurable monofunctional monomer or a silicon-based photocurable multifunctional monomer. Preferably, the silicon-based photocurable monomer is a silicon-based photocurable monofunctional monomer, more preferably a non-aromatic silicon-based photocurable monofunctional monomer.
[0102] The silicon-based photocurable monofunctional monomer may include at least one of a silsesquioxane derivative or a siloxane derivative. The siloxane derivative is different from the silsesquioxane derivative and does not include a partial cage or ladder structure.
[0103] The silsesquioxane derivative may have a partial cage structure, a ladder structure, or a random structure, preferably a polyhedral oligomeric silsesquioxane (POSS) structure represented by Formula 4.
[0104] [Formula 4]
[0105]
[0106] (In Formula 4,
[0107] Any one of R is represented by Equation 5:
[0108] [Formula 5]
[0109]
[0110] (In Formula 5,
[0111] * is the connection site to silicon,
[0112] R1 is substituted or unsubstituted C1 to C 10 an alkylene group, and
[0113] R3 is hydrogen or methyl), and
[0114] The remaining R is a substituted or unsubstituted straight or branched C1 to C 20 alkyl).
[0115] For example, the remaining R in Formula 4 may include at least one of the following: a substituted or unsubstituted linear or branched C4 to C 20 Alkyl groups, for example, isobutyl, isooctyl and 2,4,4-trimethylpentyl.
[0116] For example, the silicon-based photocurable monofunctional monomer may include at least one of a compound represented by Formula 4-1 or a compound represented by Formula 4-2:
[0117] [Formula 4-1]
[0118]
[0119] (In formula 4-1,
[0120] R 11 Any one of (R 4 is hydrogen or methyl), and
[0121] The rest R 11 It is *-CH2-CH(CH3)-CH2-C(CH3)3).
[0122] [Formula 4-2]
[0123]
[0124] (In formula 4-2,
[0125] R 13 Any one of (R 4 is hydrogen or methyl), and
[0126] The rest R 13 It is *-CH2-CH(CH3)2).
[0127] The silsesquioxane derivative may be present in an amount of 1 to 40 parts by weight (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40 parts by weight, specifically, 1 to 30 parts by weight, more specifically, 5 to 20 parts by weight, more specifically, 5 to 15 parts by weight) relative to 100 parts by weight of the photocurable monomer (B). Within this range, the silsesquioxane derivative can reduce the viscosity of the composition while improving its adhesiveness.
[0128] The siloxane derivative can be represented by Formula 6:
[0129] [Formula 6]
[0130] (R3)(R4)(R5)Si-R1-OC(=O)-CR2=CH2
[0131] (In Formula 6,
[0132] R1 is a substituted or unsubstituted C1 to C5 alkylene group,
[0133] R2 is hydrogen or methyl,
[0134] R3, R4 and R5 are each independently substituted or unsubstituted C1 to C5 alkyl, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C7 to C 10 Aralkyl or *-(-O-Si(R6)(R7)-) n -R8 (* is a bonding site of an element, R6, R7 and R8 are each independently a substituted or unsubstituted C1 to C5 alkyl group, and n is an integer of 1 to 10)).
[0135] Preferably, at least one selected from R3, R4 and R5 is *-(-O-Si(R6)(R7)-) n More preferably, R3, R4 and R5 are all *-(-O-Si(R6)(R7)-) n -R8.
[0136] The siloxane derivative may be present in an amount of 10 to 50 parts by weight (e.g., 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49 or 50 parts by weight, specifically, 10 to 40 parts by weight, more specifically, 20 to 40 parts by weight) relative to 100 parts by weight of the photocurable monomer (B). Within this range, the siloxane derivative can reduce the viscosity of the composition while improving its adhesiveness.
[0137] The silicon-based photocurable multifunctional monomer is a monomer having silicon, particularly a siloxane group (*-Si-O-Si-*), wherein the photocurable functional group may be bonded to both ends or a side chain of the monomer.
[0138] In one embodiment, the silicon-based photocurable multifunctional monomer may be represented by Formula 7:
[0139] [Formula 7]
[0140]
[0141] (In Formula 7,
[0142] R1, R2, R3, R4 and R5 are each independently hydrogen, substituted or unsubstituted C1 to C 30 Alkyl, substituted or unsubstituted C1 to C 30 Alkyl ether, *-N(R')(R") (* is the attachment site of the element, and R' and R" are the same or different from each other and are hydrogen or a substituted or unsubstituted C1 to C 30 alkyl), substituted or unsubstituted C1 to C30 Alkyl sulfide group, substituted or unsubstituted C6 to C 30 Aryl or substituted or unsubstituted C7 to C 30 Aralkyl;
[0143] Y1, Y2 and Y3 are each independently substituted or unsubstituted C1 to C 30 Alkyl, substituted or unsubstituted C1 to C 10 Monoalkylsilyloxy, substituted or unsubstituted C1 to C 10 Dialkylsilyloxy, substituted or unsubstituted C1 to C 10 Trialkylsilyloxy or formula 8:
[0144] [Formula 8]
[0145]
[0146] (In Formula 8,
[0147] * is the attachment site of the element,
[0148] R6 is substituted or unsubstituted C1 to C 10 an alkylene group, and
[0149] R7 is hydrogen or methyl); and
[0150] n is in the range of 0 to 20, m is in the range of 0 to 20, and n+m is greater than 0, at least two of Y1, Y2 and Y3 are Formula 8, or n is in the range of 2 to 20).
[0151] In Formula 7, substituted or unsubstituted C1 to C 10 The C1 to C 10 refers to the number of carbon atoms contained in one alkyl group. 10 The C1 to C 10 refers to the number of carbon atoms contained in each alkyl group. 10 The C1 to C 10 It refers to the number of carbon atoms contained in each alkyl group.
[0152] Preferably, R1, R2, R3, R4 and R5 are each independently substituted or unsubstituted C1 to C 10 alkyl, substituted or unsubstituted C1 to C5 alkyl, or substituted or unsubstituted C1 to C3 alkyl.
[0153] Preferably, R6 is a substituted or unsubstituted C1 to C5 alkylene group or a substituted or unsubstituted C1 to C3 alkylene group.
[0154] In Formula 7, n and m may each be an average value or an integer in the range of 0 to 10 or 0 to 5.
[0155] The silicon-based photocurable monomer may be obtained from a commercially available product or may be prepared by a typical method known to those skilled in the art.
[0156] The silicon-based photocurable monomer, preferably the silicon-based photocurable monofunctional monomer, may be present in an amount of 30 to 90 parts by weight (e.g., 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85 The amount of the photocurable monomer can be 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89 or 90 parts by weight, specifically, 40 to 80 parts by weight, more specifically, 40 to 70 parts by weight. Within this range, the silicon-based photocurable monomer can reduce the viscosity of the composition while improving its adhesion.
[0157] In one embodiment, the silicon-free photocurable monofunctional monomer and the silicon-based photocurable monofunctional monomer may be present in a total amount of 95 parts by weight or more, preferably 100 parts by weight, relative to 100 parts by weight of the silicon-based photocurable monomer (B).
[0158] In one embodiment, (A) and (B) may be present in a total amount of 95 parts by weight or more, preferably 100 parts by weight, relative to 100 parts by weight of the total photocurable monomers in the composition.
[0159] Photopolymerizable initiator
[0160] The photopolymerizable initiator may include any typical photopolymerizable initiator that can perform a photocuring reaction. For example, the photopolymerizable initiator may include a triazine initiator, an acetophenone initiator, a benzophenone initiator, a thioxanthone initiator, a benzoin initiator, a phosphorus initiator, an oxime initiator, or a mixture thereof.
[0161] Preferably, the photopolymerizable initiator includes a phosphorus initiator with a maximum absorption wavelength of 360nm to 400nm. In the composition according to the present invention, the phosphorus initiator can ensure better initiation performance under long wavelength UV light (e.g., 300nm to 400nm). The phosphorus initiator can include diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide, phenyl bis (2,4,6-trimethylbenzoyl) phosphine oxide, 2,4,6-trimethylbenzoyl diphenyl phosphonate (2,4,6-trimethylbenzoyldiphenylphosphinate) or a mixture thereof. For example, these initiators can be used alone or as a mixture thereof. "Maximum absorption wavelength" can be measured by typical methods known to those skilled in the art or can be a value obtained by reference to a product catalog.
[0162] The photopolymerizable initiator may be present in an amount of 1 to 10 parts by weight, preferably 1 to 5 parts by weight, relative to 100 parts by weight of the photocurable monomer (B). Within this range, the initiator may improve the photocurability of the composition without deteriorating the light transmittance due to the remaining initiator.
[0163] The composition according to the present invention can be prepared by mixing a photocurable monomer (A) containing at least one indole group and silicon, a photocurable monomer (B) and a photopolymerizable initiator (C). For example, the composition according to the present invention can be prepared in the form of a solvent-free composition containing no solvent.
[0164] The composition according to the present invention is a photocurable composition and can be photocured at 10 mW / cm 2 Up to 500mW / cm 2 The film can be cured by irradiating with UV light for 1 second to 50 seconds to form an encapsulation layer.
[0165] The composition according to the present invention may further comprise typical additives known to those skilled in the art. The additives may include, but are not limited to, heat stabilizers, antioxidants and UV absorbers.
[0166] At 25±2° C. (23° C. to 27° C.), the composition according to the present invention may have a viscosity of 7 cps to 100 cps, preferably 7 cps to 60 cps, more preferably 7 cps to 50 cps. Within this range, the composition may exhibit good inkjet performance.
[0167] The composition according to the present invention may have a photocuring rate of 89% to 100%, preferably 91% to 99%. Within this range, the cured product of the composition may be used as an organic layer. The photocuring rate may be calculated by the following formula 1.
[0168] The composition according to the present invention can 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.
[0169] The composition according to the present invention can be used to encapsulate components for devices, especially components for display devices, which can be decomposed or damaged by the penetration of gases or liquids in the surrounding environment (e.g., oxygen, moisture and / or water vapor in the atmosphere) and chemicals used to process electronic products. For example, components for devices may include lighting devices, metal sensor pads, microdisk lasers, electrochromic devices, photochromic devices, microelectromechanical systems, solar cells, integrated circuits, charge coupled devices, and light emitting polymers, but are not limited thereto.
[0170] The organic light-emitting display device according to the present invention may include an organic layer formed by the composition for encapsulating an organic light-emitting device according to an embodiment. Specifically, the organic light-emitting display device may include an organic light-emitting device and a barrier stack formed on the light-emitting device and including an inorganic layer and an organic layer, and the organic layer may be formed by the composition for encapsulating an organic light-emitting device according to an embodiment of the present invention. Therefore, the organic light-emitting display device may exhibit good reliability.
[0171] Next, we will refer to Figure 1 An organic light emitting display device according to one embodiment of the present invention is described. Figure 1 is a cross-sectional view of an organic light emitting display device according to one embodiment of the present invention.
[0172] Reference Figure 1 The organic light-emitting display device 100 includes a substrate 10, an organic light-emitting device 20 formed on the substrate 10, and a blocking stack 30 formed on the organic light-emitting device 20 and including an inorganic layer 31 and an organic layer 32, wherein the inorganic layer 31 is adjacent to the organic light-emitting device 20 and the organic layer 32 can be formed by a composition for encapsulating an organic light-emitting device according to an embodiment of the present invention.
[0173] The substrate 10 is not limited to a specific substrate as long as an organic light-emitting device can be formed on the substrate. For example, the substrate 10 may be formed of a material such as transparent glass, a plastic sheet, and a silicon or metal substrate.
[0174] The organic light emitting device 20 is generally used in an organic light emitting display device, and although not Figure 1 , but may include a first electrode, a second electrode, and an organic light-emitting layer formed between the first electrode and the second electrode. The organic light-emitting layer may have a structure 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 stacked, but is not limited thereto.
[0175] The barrier stack 30 includes an inorganic layer and an organic layer, which may be composed of different components, thereby achieving the function of encapsulating the organic light-emitting device.
[0176] The inorganic layer contains different components from the organic layer, thereby supplementing the effect of the organic layer. For example, the inorganic layer may contain at least one selected from the following: metal, non-metal, metal compound or alloy, non-metal compound or alloy, metal or non-metal oxide, metal or non-metal fluoride, metal or non-metal nitride, metal or non-metal carbide, metal or non-metal nitrogen oxide, metal or non-metal boride, metal or non-metal oxyboride, metal or non-metal silicide and their mixture. The metal or non-metal may include silicon (Si), aluminum (Al), selenium (Se), zinc (Zn), antimony (Sb), indium (In), germanium (Ge), tin (Sn), bismuth (Bi), transition metal and lanthanide metal, but is not limited thereto. Specifically, the inorganic layer may contain silicon oxide (SiO x ), silicon nitride (SiN x ), silicon oxynitride (SiO x N y )、ZnSe、ZnO、Sb2O3、AlO x ) (including aluminum oxide (Al2O3)), indium oxide (In2O3), tin oxide (SnO2), etc.
[0177] The inorganic layer may be deposited by a plasma method or a vacuum method (eg, sputtering), chemical vapor deposition, plasma chemical vapor deposition, evaporation, sublimation, electron cyclotron resonance-plasma enhanced chemical vapor deposition, or a combination thereof.
[0178] The organic layers and the inorganic layers may be alternately deposited to ensure smoothing characteristics of the inorganic layers while preventing defects of one inorganic layer from spreading to other inorganic layers.
[0179] The organic layer may be formed by coating, depositing or curing a composition for encapsulating an organic light-emitting device, or a combination thereof. For example, the composition may be coated to a thickness of 1 μm to 50 μm, and then heated to 10 mW / cm 2 Up to 500mW / cm 2 The composition is cured by irradiating with UV light for 1 second to 50 seconds to form an organic layer.
[0180] The barrier stack may include any number of organic and inorganic layers. The combination of organic and inorganic layers may vary depending on the level of resistance to oxygen and / or moisture and / or water vapor and / or chemicals. For example, organic and inorganic layers are formed with a total of 10 layers or less (e.g., 2 to 7 layers). Specifically, the organic and inorganic layers are formed with a total of 7 layers in the order of inorganic layer / organic layer / inorganic layer / organic layer / inorganic layer / organic layer / inorganic layer.
[0181] In the barrier stack, organic layers and inorganic layers may be deposited alternately. This is because the above-mentioned composition has an influence on the organic layer due to its properties. Therefore, the organic layer and the inorganic layer may complement or enhance the encapsulation of the components for the device.
[0182] Next, we will refer to Figure 2 An organic light emitting display device according to another embodiment of the present invention will be described. Figure 2 is a cross-sectional view of an organic light emitting display device according to another embodiment of the present invention.
[0183] Reference Figure 2 , an organic light-emitting display device 200 includes a substrate 10, an organic light-emitting device 20 formed on the substrate 10, and a barrier stack 30 formed on the organic light-emitting device 20 and including an inorganic layer 31 and an organic layer 32, wherein the inorganic layer 31 encapsulates an inner space 40 in which the organic light-emitting device 20 is accommodated, and the organic layer 32 may be formed of a composition for encapsulating an organic light-emitting device according to an embodiment of the present invention. The organic light-emitting display device 200 according to this embodiment is substantially the same as the organic light-emitting display device according to the above embodiment, except that the inorganic layer is not adjacent to the organic light-emitting device.
[0184] Invention Mode
[0185] Next, the present invention will be described in more detail with reference to some examples. It should be understood that these examples are provided for illustration only and should not be interpreted as limiting the present invention in any way.
[0186] Example 1
[0187] (1) Preparation of a photocurable monomer containing at least one indole group and silicon
[0188] <Reaction 1>
[0189]
[0190] (In reaction 1, Me is methyl).
[0191] Sodium iodide (NaI) (8.0 equivalents) was added to a solution (0.2M) of compound 1 (1.0 equivalents) dissolved in acetone, followed by reflux for 18 hours. The prepared reaction mixture was cooled to room temperature and then desolventized under reduced pressure. After the reaction mixture was redissolved in distilled water, the corresponding solution layer was extracted with dichloromethane and the prepared dichloromethane layer was washed again with distilled water and dried over MgSO. Compound 2 was obtained by concentrating the product under reduced pressure. The compound was used in subsequent reactions without additional purification.
[0192] At 0°C, cyanoacetic acid (1 equivalent) was slowly added to a mixture of sodium hydride (NaH) (1.2 equivalents) and N,N-dimethylformamide. After the mixture was stirred at the same temperature for 1 hour, a solution of compound 2 (3.0 equivalents) dissolved in N,N-dimethylformamide was added thereto. After the resulting solution was heated to 50°C, the reaction was allowed to proceed overnight. The resulting solution was diluted with distilled water and extracted with ethyl acetate. The organic layer was washed with distilled water, dried over MgSO4, and concentrated. Compound 3 (yield 60%) was obtained by column chromatography (eluent: hexane / ethyl acetate). Compound 3 has the following 1 H NMR analysis results: 1 H NMR (300MHz, CDCl3, ppm): 3.90(2H,s), 3.45(2H,s), 1.99(2H,s), 0.26(6H,s), 0.22(6H,s).
[0193] <Reaction 2>
[0194]
[0195] (In reaction 2, Me is methyl).
[0196] Sodium methacrylate (1.2 equivalents) and butylated hydroxytoluene (BHT) (0.4 mol%) were added to a solution (0.25 M) of compound 3 (1 equivalent) dissolved in N,N-dimethylformamide, followed by stirring at 50° C. overnight. After diluting the resulting solution with distilled water and extracting with ethyl acetate, the corresponding organic layer was washed with distilled water and dried over MgSO4. After concentration under reduced pressure, compound 4 was obtained by column chromatography (eluent: hexane / ethyl acetate) (yield: 23%). Compound 4 has the following 1 H NMR analysis results. 1 H NMR (300MHz, 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).
[0197] <Reaction 3>
[0198]
[0199] (In reaction 3, Me is methyl).
[0200] A solution (0.2 M) of compound 5 (1.0 eq.) and sodium hydride (NaH) (1.5 eq.) dissolved in N,N-dimethylformamide was stirred for 30 minutes at 0°C, and then methyl iodide (MeI) (2 eq.) was added to the solution. The solution was stirred overnight at room temperature. The solution was diluted with distilled water and extracted with ethyl acetate. The organic layer was washed again with distilled water and dried over MgSO4. After concentration under reduced pressure, compound 6 was obtained (yield: 89%). Compound 6 has the following 1 H NMR analysis results. 1 H NMR (300MHz, (CD3)2SO, ppm): 9.61 (1H, s), 8.23 (1H, m), 7.64 (6H, m), 7.37 (2H, m), 3.70 (3H, s).
[0201] <Reaction 4>
[0202]
[0203] (In reaction 4, Me is methyl).
[0204] To a solution (1.0 M) of compound 4 (1.5 equivalents) and compound 6 (1.0 equivalents) dissolved in pyridine, piperidine (2.0 equivalents) and BHT (0.4 mol%) were added, and the solution was subsequently stirred at room temperature for 100 minutes. After the solvent was removed by distillation under reduced pressure, the resulting solution was dissolved in ethyl acetate again. The corresponding organic layer was washed with 0.1N HCl (aq) and dried over MgSO4. After concentration under reduced pressure, a compound corresponding to formula 1-1 was prepared by column chromatography (eluent: hexane / ethyl acetate) (yield: 56%). The compound of formula 1-1 has the following 1 H NMR analysis results. 1 H NMR(300MHz, 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).
[0205] (2) Preparation of composition
[0206] 4 parts by weight of the compound of Formula 1-1, 58 parts by weight of tridecyl methacrylate (Aldrich) as a photocurable monomer, 30 parts by weight of a silicon-based photocurable monofunctional monomer (Formula 9, SM-2), 10 parts by weight of a silicon-based photocurable monomer (methacryloctyl POSS, Formula 10, MA0719, Hybrid Plastics Co., Ltd.), 2 parts by weight of a silicon-based photocurable monofunctional monomer (Formula 11, MAC-SQ SI-20, Toagosei Co., Ltd.) and 3 parts by weight of a photopolymerizable initiator (Irgacure TPO) are placed in a 125 ml brown polypropylene bottle and mixed using an oscillator at room temperature for 3 hours to prepare an encapsulation composition.
[0207] [Formula 9]
[0208]
[0209] [Formula 10]
[0210]
[0211] (R 11 yes And R 12 It is *-CH2-CH(CH3)-CH2-C(CH3)3).
[0212] [Formula 11]
[0213]
[0214] (R 11 yes And R 13 It is *-CH2-CH(CH3)2).
[0215] Comparative Example 1
[0216] 58 parts by weight of tridecyl methacrylate (Aldrich) as a photocurable monomer, 30 parts by weight of a silicon-based photocurable monomer (SM-2), 10 parts by weight of methacryloyloctyl POSS (MA0719, HybridPlastics Co., Ltd.), 2 parts by weight of MAC-SQ SI-20 (Toagosei Co., Ltd.) as a photocurable monomer and 3 parts by weight of a photopolymerizable initiator (Irgacure TPO) were placed in a 125 ml brown polypropylene bottle and mixed using an oscillator at room temperature for 3 hours to prepare a composition for encapsulation.
[0217] For the compositions prepared in Examples and Comparative Examples, the following properties were measured and the results are shown in Table 1.
[0218] (1) Light transmittance (unit: %): Each composition of the examples and comparative examples was sprayed on a glass substrate and 2 UV curing was performed by UV irradiation for 20 seconds under 400° C. to form an organic layer having a thickness of 10 μm. The light transmittance of the organic layer was measured at a wavelength of 405 nm using Lambda 950 (Perkin Elmer).
[0219] (2) Solution preparation stability: The compound of Formula 1-1 is continuously added in increasing amounts to the mixture of the photocurable monomer and the photopolymerizable initiator in the example, while measuring the amount of the compound of Formula 1-1 until no precipitation of the compound of Formula 1-1 is observed visually with the naked eye.
[0220] (3) Storage stability: The compositions prepared in the Examples and Comparative Examples were stored at room temperature (25° C.) for a predetermined period of time, while checking the precipitation of the compound of Formula 1-1 under visual observation with the naked eye. More specifically, the change in light transmittance over time at a wavelength of 405 nm was checked using the above-mentioned light transmittance measurement method. The storage stability was determined based on the maximum period of time during which no change in light transmittance was observed.
[0221] (4) Dielectric constant (unit: none): Each composition prepared in the examples and comparative examples was coated on a chromium (Cr) plate to a predetermined thickness and then subjected to a 100 mW / cm 2 The film was cured by UV irradiation at an irradiance of 1000 nm for 10 seconds to form a coating film of 8 μm thick. An aluminum electrode (electrode for measuring dielectric constant) was deposited on the coating film, and then the dielectric constant of the coating film was measured at 200 kHz and 25° C. using an impedance analyzer (E4990A, Impedance Analyzer).
[0222] (5) Viscosity (unit: cps): The viscosity of each composition prepared in Examples and Comparative Examples was measured at 24.8° C. using a viscometer rotor No. 40 (LV DV-II Pro, Brookfield Co., Ltd).
[0223] (6) Photocuring rate (unit: %): The photocuring rate of each composition prepared in the examples and comparative examples was measured using an FT-IR spectrometer (NICOLET 4700, Thermo Co., Ltd.) at 1635 cm -1 (C=C) and 1720cm -1Each encapsulation composition was applied to a glass substrate by a sprayer and then heated at 100 mW / cm 2 The cured film was irradiated with UV light for 20 seconds to prepare a sample having a size of 20 cm×20 cm×3 μm (width×length×thickness). Then, the cured film was measured at 1635 cm using an FT-IR spectrometer (NICOLET 4700, Thermo Co., Ltd.). -1 (C=C) and 1720cm -1 The absorption peak intensity near (C=O) was calculated by Equation 1.
[0224] [Equation 1]
[0225] Photocuring rate (%) = |1-(A / B)| x 100
[0226] (In Equation 1, A is the measured value at 1635 cm for the cured film. -1 The absorption peak intensity near 1720cm -1 The ratio of the absorption peak intensities near
[0227] B is the measured value at 1635 cm for this composition. -1 The absorption peak intensity near 1720cm -1 The ratio of the absorption peak intensities near
[0228] [Table 1]
[0229]
[0230] As shown in Table 1, the composition for encapsulating an organic light-emitting device according to the present invention can form an organic layer having a low dielectric constant and low light transmittance at a wavelength of 420 nm or less after curing, and can ensure high solution preparation stability even when using a UV absorbing photocurable monomer and can also ensure storage stability over a long period of time.
[0231] In contrast, the composition of Comparative Example 1, which did not contain an indole group and a silicon photocurable monomer, failed to form an organic layer having a low light transmittance at a wavelength of 420 nm or less.
[0232] It should be understood that various modifications, changes, variations and equivalent embodiments may be made by those skilled in the art without departing from the spirit and scope of the present invention.
Claims
1. A composition for encapsulating an organic light-emitting device, comprising: (A) a photocurable monomer containing at least one indole group and silicon, (B) a photocurable monomer, and (C) a photopolymerizable initiator.
2. The composition for encapsulating an organic light-emitting device according to claim 1, wherein: The photocurable monomer (A) is represented by Formula 1: [Formula 1] (In Formula 1, R1 is hydrogen or a substituted or unsubstituted C1 to C 10 alkyl, R2 is substituted or unsubstituted C6 to C 20 Aryl or substituted or unsubstituted C7 to C 20 Aralkyl, R3, R4, R5 and R6 are each independently hydrogen, substituted or unsubstituted C1 to C 10 Alkyl or substituted or unsubstituted C6 to C 20 Aryl, and L1 and L2 are each independently hydrogen, cyano (-CN), substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 20 Aryl, substituted or unsubstituted C7 to C 20 Aralkyl, *-R 7 -Epoxy (* is the attachment site of the element, R 7 is a C1 to C5 alkylene group) or a siloxane-containing (meth)acrylate group, At least one of L1 and L2 is a siloxane-containing (meth)acrylate group or -R 7 -epoxy).
3. The composition for encapsulating an organic light-emitting device according to claim 2, wherein: The photocurable monomer (A) is represented by any one of the following formulae 1-1 to 1-12: [Formula 1-1] [Formula 1-2] [Formula 1-3] [Formula 1-4] [Formula 1-5] [Formula 1-6] [Formula 1-7] [Formula 1-8] [Formula 1-9] [Formula 1-10] [Formula 1-11] [Formula 1-12] (In formulae 1-1 to 1-12, R9 is hydrogen or methyl, Me is methyl, and Et is ethyl).
4. The composition for encapsulating an organic light-emitting device according to claim 1, wherein: The photocurable monomer (B) includes at least one of a silicon-free photocurable monomer or a silicon-based photocurable monomer.
5. The composition for encapsulating an organic light-emitting device according to claim 4, wherein: The silicon-free photocurable monomer includes a silicon-free photocurable monofunctional monomer.
6. The composition for encapsulating an organic light-emitting device according to claim 5, wherein: The silicon-free photocurable monofunctional monomer includes a linear or branched C1 to C 20 Alkyl mono(meth)acrylate.
7. The composition for encapsulating an organic light-emitting device according to claim 4, wherein: The silicon-based photocurable monomer includes at least one of a silicon-based photocurable monomer represented by Formula 4 or a silicon-based photocurable monomer represented by Formula 6: [Formula 4] (In Formula 4, Any one of R is represented by Equation 5: [Formula 5] (In Formula 5, * is the connection site to silicon, R1 is substituted or unsubstituted C1 to C 10 an alkylene group, and R3 is hydrogen or methyl), and The remaining R is a substituted or unsubstituted straight or branched C1 to C 20 alkyl), [Formula 6] (R3)(R4)(R5)Si-R1-OC(=O)-CR2=CH2 (In Formula 6, R1 is a substituted or unsubstituted C1 to C5 alkylene group, R2 is hydrogen or methyl, R3, R4 and R5 are each independently substituted or unsubstituted C1 to C5 alkyl, substituted or unsubstituted C6 to C 10 Aryl and substituted or unsubstituted C7 to C 10 Aralkyl or *-(-O-Si(R6)(R7)-) n -R8 (* is a bonding site of an element, R6, R7 and R8 are each independently a substituted or unsubstituted C1 to C5 alkyl group, and n is an integer of 1 to 10)).
8. The composition for encapsulating an organic light-emitting device according to claim 1, comprising: 100 parts by weight of the photocurable monomer (B); 0.01 parts by weight to 10 parts by weight of the photocurable monomer (A) relative to 100 parts by weight of the photocurable monomer (B); and 1 part by weight to 10 parts by weight of the photopolymerizable initiator (C) relative to 100 parts by weight of the photocurable monomer (B). 9 . An organic light-emitting display device, comprising an organic layer formed from the composition for encapsulating an organic light-emitting device according to claim 1 .
Citation Information
Patent Citations
Organic light emmiting diode display apparatus
KR1020160150255A