KR20200063387A - Composition and compound for encapsulating organic light emitting diode and oencapsulated apparatus comprising the same - Google Patents

Abstract

The present invention provides an encapsulation composition for an organic light emitting device and an encapsulation device comprising the same, which improve the reliability of a member for the device by preventing moisture and oxygen from penetrating from the outside. The encapsulation composition for the organic light emitting device includes a compound represented by chemical formula 1.

Description

Encapsulation compound, composition for organic light-emitting device, and encapsulated device including the same {COMPOSITION AND COMPOUND FOR ENCAPSULATING ORGANIC LIGHT EMITTING DIODE AND OENCAPSULATED APPARATUS COMPRISING THE SAME}

The present invention relates to a sealing composition for an organic light emitting device and a sealed device comprising the same.

In an organic light emitting diode (OLED), electrons injected from a cathode and holes injected from an anode combine in an emission layer of an organic light emitting unit to form an electron-hole pair, In the process of recombination, they are flat panel display elements that emit light. The organic light emitting device exhibits high luminous efficiency in red, green, blue, and white, which are the three primary colors of light, has a low driving voltage and power consumption, a wide viewing angle, and a fast response speed of pixels, so it can display high-quality video. Have.

In addition, the organic light emitting device is capable of realizing an ultra-thin and ultra-light display that can be manufactured to a thickness of 1 mm or less on a substrate such as glass or plastic, and is actively researched in the field of flexible displays. However, in the organic light emitting device, the light emitting material and the electrode material are oxidized by oxygen or moisture, and as a result, problems such as dark spots and pixel shrinkage occur, resulting in a decrease in lifespan and efficiency. In addition, it has been reported that the life and efficiency of the OLED device is reduced due to external light including sunlight. The sunlight has a ratio of 2.5% of ultraviolet light, 51.5% of visible light, and 40.6% of ultraviolet light. Among them, ultraviolet light has a small amount of light, but it is energy-efficient, causing decomposition and deterioration of organic light-emitting materials, thereby bonding molecules of low and high molecular materials. Is destroyed. At this time, there is no general route for decomposition of organic materials and organic-metal materials by UV. Normally, the organic material and the organic-metallic material of the organic light emitting device absorb light from the ground state to the singlet excited state under light excitation, and emit light when returning to the ground state. At this time, dissociation may occur at the binding site where the binding energy in the organic or organic-metal molecule is similar to or lower than the energy in the singlet excited state. In addition, it is possible to act as an impurity by forming a neutral saturated decomposition product by reacting with the radicals generated at this time.

Due to this, when the organic light-emitting device receives external light (solar light) for a long time, the organic material or organic-metal material of the organic light-emitting device is continuously subjected to stress due to ultraviolet rays entering the device, thereby destroying the molecular bond of the material. , Due to the combination of the destroyed molecules, the color coordinate of the organic light emitting device is changed, the driving voltage is increased, and the life is reduced.

As described above, it is one of the key technologies to develop an encapsulation technology that blocks oxygen, moisture, and ultraviolet rays flowing into the organic light emitting device.

This encapsulation technology can be roughly divided into three methods: Can (Glass encap), TFE (thin film encap), and Hybrid. Each method includes a metal or glass cover plate with gas barrier properties and a can with a getter. Method and TEF method, which can be referred to as a face sealing method that implements a barrier property with an inorganic or inorganic multilayer thin film on the upper layer of the device and a plastic barrier film as a cover plate, and between the passivation thin film It can be explained by the hybrid method of positioning the adhesive layer. The sealing method is disclosed in Korean Patent Publication No. 2011-0071039.

The Can (Glass encap) method, which has been widely used to date, is the best sealing property by placing an organic light-emitting element between two glass composed of a substrate and a cover, sealing the glass powder with a laser, or using UV adhesive to seal. However, the thermal conductivity characteristics are poor due to the inert gas in the device, and there is a disadvantage in that the cost of glass processing is increased due to the large area, and it is difficult to apply to the production of flexible OLED panels requiring flexibility.

In order to compensate for the shortcomings of such a glass encapsulation technology, an organic light emitting device is formed by alternately laminating an organic light emitting device with an inorganic layer such as Al ₂ O ₃ having high barrier properties against oxygen or moisture, and an organic layer of a polymer as a thin film. Thin film encapsulation (TFE), a multi-layer thin film encapsulation technology, is actively being studied.

The organic barrier layer used in the TFE method is located between the inorganic barrier layers, and the inorganic barrier layer may be metal oxide/nitride such as AlxOy, SiOx, SiNy, SiOxNy, and the inorganic barrier layer is sputtering deposition on the organic barrier layer (sputtering) deposition) or plasma enhanced chemical vapor deposition (PECVD).

US Patent 7767498 discloses that the more pairs of thin film organic barrier layers and inorganic barrier layers, the more favorable the barrier properties of moisture and oxygen, but after several deposition processes under vacuum conditions, the barrier properties caused by foreign material mixing A decrease in yield along with a decrease has been reported as a disadvantage.

In recent studies, research has been conducted in the direction of increasing the thickness of the organic/inorganic barrier layer and reducing the number of layers in the thin film multi-layer structure to overcome the decrease in yield while maintaining the barrier properties. This is because the number of processes is reduced when the number is reduced, and the manufacturing cost can be reduced while overcoming the characteristic drop and yield drop due to foreign material mixing.

Accordingly, the present invention provides a sealing material composition capable of protecting an organic light emitting device from ultraviolet rays while having flexibility during deposition to conform to a display development direction that is converted from a rigid display to a flexible light emitting device.

An object of the present invention is to provide a composition for encapsulation, which has UV protection and is suitable for an inkjet process.

Another object of the present invention is to provide a composition for encapsulation capable of forming a thick film and having flexibility.

Another object of the present invention is to provide a composition for encapsulation capable of forming a barrier layer for encapsulation of an environmentally sensitive device member.

The composition for encapsulating an organic light emitting device according to embodiments of the present invention may include a compound (A) represented by Formula 1 below.

In another aspect, the present invention includes a device member and a multi-layer barrier layer disposed on the device member and composed of an inorganic barrier layer and an organic barrier layer, wherein the organic barrier layer comprises the compound (A) of Formula 1 An encapsulated device is provided.

The composition for encapsulation according to the present invention can improve the reliability of an OLED device by preventing moisture and oxygen from penetrating from outside after curing. In addition, the encapsulated device according to the present invention can prevent performance degradation due to moisture and oxygen penetrating from the outside.

1 is an exemplary view of an organic light emitting device according to an embodiment of the present invention.
2 is a view schematically showing the structure of an electronic device including an organic light emitting device.
3 and 4 are transmittance data measured in Examples and Comparative Examples.

Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

In adding reference numerals to the components of each drawing, it should be noted that the same components are given the same reference numerals as possible, even if they are displayed on different drawings. In addition, in describing the present invention, when it is determined that detailed descriptions of related well-known structures or functions may obscure the subject matter of the present invention, detailed descriptions thereof will be omitted.

In addition, in describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only for distinguishing the component from other components, and the nature, order, or order of the component is not limited by the term. When a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to the other component, but another component between each component It should be understood that elements may be "connected", "coupled" or "connected".

Also, if a component such as a layer, film, region, plate, etc. is said to be "above" or "on" another component, this is not only when the other component is "directly above" but also with another component in the middle It should be understood that the case may be included. Conversely, it should be understood that when a component is said to be “just above” another part, it means that there is no other part in between.

Terms used in this specification and in the appended claims are as follows, unless stated otherwise.

As used herein, the terms "halo" or "halogen" include fluorine (F), chlorine (Cl), bromine (Br), and iodine (I), unless otherwise noted.

The term "alkyl" or "alkyl group" as used herein has 1 to 60 carbons connected by a single bond, unless otherwise specified, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted By radicals of saturated aliphatic functional groups, including cycloalkyl groups, cycloalkyl-substituted alkyl groups.

As used herein, the term "haloalkyl group" or "halogenalkyl group" means an alkyl group substituted with halogen unless otherwise specified.

As used herein, the terms "alkenyl" or "alkynyl" have a double or triple bond, respectively, unless otherwise specified, including straight or branched chain groups, and having from 2 to 60 carbon atoms, It is not limited.

As used herein, the term "cycloalkyl" means an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, and is not limited thereto.

As used herein, the term "alkoxy group" or "alkyloxy group" refers to an alkyl group to which an oxygen radical is bonded, and has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.

As used herein, the terms "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means an alkenyl group to which an oxygen radical is attached, and 2 to 60 unless otherwise specified. Has carbon number, but is not limited thereto.

As used herein, the terms "aryl group" and "arylene group" have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto. In this specification, an aryl group or an arylene group includes monocyclic, ring aggregates, conjugated several ring systems, compounds, and the like. For example, the aryl group may refer to a phenyl group, a monovalent functional group of biphenyl, a monovalent functional group of naphthalene, a fluorenyl group, or a substituted fluorenyl group.

As used herein, the terms "fluorenyl group" or "fluorenylene group" means a monovalent or divalent functional group of fluorene, respectively, unless otherwise specified, and "substituted fluorenyl group" or "substituted flu. Orenylene group" means a monovalent or divalent functional group of substituted fluorene, and "substituted fluorene" means at least one of the following substituents R, R', R", R'" is a functional group other than hydrogen It means that R and R'are bonded to each other to form a compound as a spy together with the carbon to which they are bonded.

In addition, R, R', R" and R"' are each independently an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, 3 It may be a heterocyclic group having a carbon number of 30 to 30, for example, the aryl group may be phenyl, biphenyl, naphthalene, anthracene or phenanthrene, the heterocyclic group pyrrole, furan, thiophene, pyrazole, imidazole , Triazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, indole, benzofuran, quinazoline or quinoxaline, for example, the substituted fluorenyl group and fluorylene group are 9,9, respectively. It may be a monovalent or divalent functional group of -dimethylfluorene, 9,9-diphenylfluorene and 9,9'-spyrobi[9H-fluorene].

The term "ring assemblies" as used herein refers to two or more ring systems (single or fused ring systems) directly connected to each other through a single bond or a double bond, and directly between such rings. This means that the number of linkages is one less than the total number of ring systems in this compound. In the ring aggregate, the same or different ring systems may be directly connected to each other through a single bond or a double bond.

Since the aryl group includes a ring aggregate in the present specification, the aryl group includes biphenyl and terphenyl in which a benzene ring, which is a single aromatic ring, is connected by a single bond. In addition, since the aryl group also includes a compound in which the aromatic ring system bonded to the aromatic single ring is connected by a single bond, for example, fluorene, an aromatic ring system bonded to a benzene ring, which is an aromatic single ring, is conjugated to a pi-electron system by a single bond ( Compounds linked to form conjugated pi electron systems) are also included.

As used herein, the term "conjugated multiple ring system" means a fused ring form sharing at least two atoms, and a ring system of two or more hydrocarbons is a conjugated form and at least one heteroatom is included. And a heterocyclic system in which at least one is conjugated. These conjugated several ring systems may be aromatic rings, heteroaromatic rings, aliphatic rings or combinations of these rings.

The term "spiro compound" as used herein has a'spiro union', and a spiro linkage refers to a link made by two rings sharing only one atom. At this time, the atoms shared between the two rings are called'spyro atoms', and these are'monospyro-','dispiro-', and'trispyro' depending on the number of spy atoms in a compound. It is called a compound.

As used herein, the term “heterocyclic group” includes aromatic rings such as “heteroaryl group” or “heteroarylene group” as well as non-aromatic rings, and carbon atoms each containing one or more heteroatoms unless otherwise specified. It means a ring of 2 to 60, but is not limited thereto. The term "heteroatom" as used herein refers to N, O, S, P or Si unless otherwise indicated, and the heterocyclic group is a monocyclic, ring aggregate, heterozygous multiple ring system, spy containing heteroatoms. Means a compound and the like.

In addition, "heterocyclic group" may include a ring containing SO ₂ instead of carbon forming a ring. For example, "heterocyclic group" includes the following compounds.

The term "ring" as used herein includes monocyclic and polycyclic, includes heterocycles containing at least one heteroatom as well as hydrocarbon rings, and includes aromatic and non-aromatic rings.

As used herein, the term "polycyclic" includes ring assemblies, fused multiple ring systems and spiro compounds such as biphenyl, terphenyl, and the like, including aromatic as well as non-aromatic, hydrocarbons The ring includes of course a heterocycle comprising at least one heteroatom.

In addition, when the prefix is named consecutively, it means that the substituents are listed in the order described first. For example, in the case of an arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of an alkoxycarbonyl group, it means a carbonyl group substituted with an alkoxy group, and in the case of an arylcarbonyl alkenyl group, it means an alkenyl group substituted with an arylcarbonyl group, wherein An arylcarbonyl group is a carbonyl group substituted with an aryl group.

Also, unless expressly stated, the term "substituted" in the term "substituted or unsubstituted" as used herein is deuterium, halogen, amino group, nitrile group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkylamine group, C ₁ -C ₂₀ alkylthiophene group, C ₆ -C ₂₀ arylthiophene group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, C ₈ -C ₂₀ aryl alkenyl group, a silane group, a boron Means a group, a germanium group, and one or more substituents selected from the group consisting of C ₂ -C ₂₀ heterocyclic groups including at least one hetero atom selected from the group consisting of O, N, S, Si and P And is not limited to these substituents.

In the present specification, the'functional group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituent may describe'the name of a functional group reflecting a singer', but is described as a'parent compound name' You may. For example, in the case of'phenanthrene', which is a kind of aryl group, the monovalent'group' is'phenanthryl (group)', and the divalent group is'phenanthrylene (group)', so as to distinguish the singer and write the name of the group It can be done, but it can be described as the parent compound name'phenanthrene' regardless of the singer. Similarly, in the case of pyrimidine, regardless of the valence, it is described as'pyrimidine', or in the case of monovalent, pyrimidinyl (group), in the case of divalent, pyrimidineylene (group), etc. It can also be written as'name'. Accordingly, in the present specification, when the type of a substituent is described as a parent compound name, it may mean an n-valent'group' formed by detaching a hydrogen atom bonded to a carbon atom and/or a heteroatom of the parent compound.

In addition, unless expressly stated, the formula used in the present specification is applied in the same manner as the substituent definition by the exponent definition of the following formula.

Here, when a is 0, the substituent R ¹ is absent, when a is 1, one substituent R ¹ is bound to any one of carbons forming a benzene ring, and when a is 2 or 3, respectively At the same time, R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it binds to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bound to the carbon forming the benzene ring is omitted .

In this specification, the substituents are bonded to each other to form a ring, a plurality of substituents bonded to each other is a carbon atom; It means to form a saturated or unsaturated ring by sharing at least one atom of the heteroatoms O, N, S, Si and P. For example, in the case of naphthalene, an adjacent methyl group and a butadienyl group substituted in any one benzene ring share one carbon to form an unsaturated ring, or a vinyl group and a propylene group share one carbon to be unsaturated. It can be regarded as forming a ring. In addition, in the case of fluorene, it can be seen as an aryl group having 13 carbon atoms in itself, but it can also be seen that two methyl groups substituted with a biphenyl group are bonded to each other to form a ring.

1 is an exemplary view of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180 and a first electrode 110 and a second electrode 180 formed on the substrate 110. ) Between the organic material layer comprising the compound according to the present invention. At this time, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may sequentially include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160 and an electron injection layer 170 on the first electrode 120. At this time, at least one of these layers may be omitted, or a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like may be further included, and the electron transport layer 160, etc., serves as a hole blocking layer. You could do it.

In addition, although not shown, the organic electric device according to the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on a surface opposite to the organic material layer among at least one surface of the first electrode and the second electrode.

The compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, an electron injection layer 170, a light emitting layer 150, a light efficiency improving layer, a light emitting auxiliary layer, etc. It can be used as a material. In one example, the compound of the present invention may be used as a light emitting auxiliary layer 151 and/or a light emitting layer 150 material.

On the other hand, even in the same core, since a band gap, an electrical characteristic, an interface characteristic, etc. may be changed depending on which substituent is attached to which position, the selection of the core and the combination of sub-substituents attached thereto are very important. When an optimum combination of energy level and T ₁ value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) is achieved, long life and high efficiency can be simultaneously achieved.

As described above, in order to solve the light emission problem in the hole transport layer in the recent organic electroluminescent device, it is preferable to form an auxiliary light emitting layer between the hole transport layer and the light emitting layer, and correspond to each light emitting layer (R, G, B) Therefore, it is necessary to form different light-emitting auxiliary layers. In other words, the light emitting auxiliary layer includes a red light emitting layer, a green light emitting layer, a red light emitting auxiliary layer corresponding to a blue light emitting layer, a green light emitting auxiliary layer and a blue light emitting auxiliary layer. On the other hand, in the case of the light-emitting auxiliary layer, since it is necessary to grasp the relationship between the hole transport layer and the light-emitting layer (host), even if similar cores are used, it will be very difficult to infer the characteristics of the organic layer used.

Therefore, by forming a light-emitting layer, a hole transport layer and/or a light-emitting auxiliary layer using the compound according to Formula 1 of the present invention, the energy level (level) and T ₁ value between each organic material layer, the material's intrinsic properties (mobility, interfacial properties, etc.) By optimizing, etc., it is possible to simultaneously improve the life and efficiency of the organic electric device.

The organic light emitting device according to an embodiment of the present invention may be manufactured using various deposition methods. It may be manufactured using a deposition method such as Physical Vapor Deposition (PVD) or Chemical Vapor Deposition (CVD), for example, by depositing a metal or conductive metal oxide or an alloy thereof on a substrate to form the anode 120 Then, an organic material layer including a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160 and an electron injection layer 170 is formed thereon, and then, as a cathode 180 thereon, It can be produced by depositing a material that can be used. In addition, a light-emitting auxiliary layer 151 may be additionally formed between the hole transport layer 140 and the light-emitting layer 150.

In addition, the organic material layer is a solution process or a solvent process using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blading process, It can be produced with fewer layers by a method such as a screen printing process or a thermal transfer method. Since the organic material layer according to the present invention can be formed in various ways, the scope of the present invention is not limited by the formation method.

The organic electric device according to the present invention may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.

WOLED (White Organic Light Emitting Device) has the advantage of being easy to realize high resolution and excellent processability, and can be manufactured by using the color filter technology of the existing LCD. Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Typically, R (Red), G (Green), B (Blue) light-emitting parts are arranged in a mutually planar side-by-side manner, and a stacking method in which R, G, and B light-emitting layers are stacked up and down. There is a color conversion material (CCM) method using electroluminescence by the blue (B) organic light-emitting layer and photo-luminescence of the inorganic phosphor using light therefrom. Can be applied to these WOLEDs.

In addition, the organic electric device according to the present invention may be one of an organic light emitting device (OLED), an organic solar cell, an organic photoreceptor (OPC), an organic transistor (organic TFT), a monochromatic or white lighting device.

In addition, in the present invention, an encapsulation layer 300 for protecting the organic light emitting device 200 may be further included. 1 discloses a configuration in which the encapsulation layer 300 is a single layer, but the present invention is not limited thereto, and the encapsulation layer 300 may be formed of multiple layers. Looking at this configuration with reference to Figure 2 as follows.

2 is a view schematically showing an example of a structure of an electronic device including an organic light emitting device. The electronic device disclosed in FIG. 2 includes a substrate 110, an organic light emitting device 200 disposed on the substrate 110, and an encapsulation layer 300 arranged on the organic light emitting device 200. In the electronic device according to an example, the organic light emitting device 200 may be protected using the encapsulation layer 300.

Meanwhile, FIG. 2 discloses an embodiment in which the encapsulation layer 300 according to the present invention is composed of multiple layers consisting of the first encapsulation layer 310 and the second encapsulation layer 320. Although FIG. 2 discloses a configuration in which the encapsulation layer 300 is two layers, the present invention may include all configurations in which the encapsulation layer 300 is two or more layers. When the encapsulation layer 300 is composed of multiple layers of two or more layers, it may include an inorganic barrier layer and an organic barrier layer. For example, when the first encapsulation layer 310 is an inorganic barrier layer, the second encapsulation layer 320 may be an organic barrier layer, and when the first encapsulation layer 310 is an organic barrier layer, the second encapsulation layer 320 ) May be an inorganic barrier layer.

In addition, as shown in FIG. 2, the encapsulation layer 300 of the present invention may be disposed on a device member. Specifically, the encapsulation layer 300 may be disposed on the organic light emitting device 200, and more specifically, the encapsulation layer 300 may be disposed to surround the organic light emitting device 200. That is, the encapsulation layer 300 may be disposed in a structure capable of effectively protecting the organic light emitting device 200. At this time, the encapsulation layer 300 has an effect of improving the reliability of the electronic device by blocking moisture and oxygen in the organic light emitting device 200. The composition for sealing constituting the encapsulation layer 300 may include the compound (A) represented by the following Chemical Formula 1, thereby exhibiting the above-described effect.

Hereinafter, the compound (A) according to an aspect of the present invention will be described. Compound (A) according to an aspect of the present invention is represented by the following formula (1).

Hereinafter, Formula 1 will be described.

A ring and B ring are each the same or different from each other, and C ₆ ~ C ₃₀ aryl group; A fused ring group of an aromatic ring of C ₆ to C ₃₀ and an aliphatic ring of C ₃ to C ₃₀ ; It can be selected from any one of C ₂ ~ C ₃₅ heterologo group.

R ₁ and R ₂ are each independently the same or different and deuterium; Tritium; Hydroxyl group; Halogen group; Cyano group; C ₆ ~ C ₆₀ Aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₁ ~ C ₆₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; C ₂ ~ C ₆₀ alkenyl group; C ₁ ~ C ₆₀ alkoxyl group; C ₆ ~ C ₆₀ Aryloxy group; C ₇ ~ C ₆₀ Arylalkyl group; C ₂ ~ C ₃₀ Alkenyloxyl group; Ether group; C ₈ ~ C ₆₀ Alkenyl aryl group; C ₃ ~ C ₆₀ cycloalkyl group; Silane group; 2siloxane groups; C ₇ ~ C ₆₀ Aryl alkoxyl group; C ₈ ~ C ₆₀ Aryl alkenyl group; And it may be a substituent selected from any one of C ₂ ~ C ₆₀ alkoxyl carbonyl group.

R ₁ and R ₂ are the same as or different from each other as a plurality when o and p are 2 or more, and a plurality of R ₁ and R ₂ Between Each can be combined to form a ring.

o is an integer from 0 to 8, p may be an integer from 0 to 7. Since o and p are the coefficients of the substituents R ₁ and R ₂ , hydrogen or the like will be located at a position where R ₁ or R ₂ is not substituted in the compound that can be selected as A and B rings in this specification.

R ₃ to R ₆ are each independently the same or different and deuterium; Tritium; Hydroxyl group; Halogen group; Cyano group; C ₆ ~ C ₆₀ Aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₁ ~ C ₆₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; C ₂ ~ C ₆₀ alkenyl group; C ₁ ~ C ₆₀ alkoxyl group; C ₆ ~ C ₆₀ Aryloxy group; C ₇ ~ C ₆₀ Arylalkyl group; C ₂ ~ C ₃₀ Alkenyloxyl group; Ether group; C ₈ ~ C ₆₀ Alkenyl aryl group; C ₃ ~ C ₆₀ cycloalkyl group; Silane group; 2siloxane groups; C ₇ ~ C ₆₀ Aryl alkoxyl group; C ₈ ~ C ₆₀ Aryl alkenyl group; And C ₂ ~ C ₆₀ may be a substituent selected from any one of the alkoxyl carbonyl group, R ₃ to R ₆ may be bonded to each other to form a ring.

X is O (oxygen), S (sulfur), NAr ₁ or CR'R", R'and R" are C ₁ ~ C ₃₀ alkyl group; C ₆ ~ C ₃₀ aryl group, R'and R" may be combined with each other to form a spy compound, Ar ₁ is C ₁ ~ C ₃₀ alkyl group; C ₆ ~ C ₆₀ aryl group; C ₂ It may be selected from any one of ~ C ₆₀ heterocyclic group.

L ₁ is a single bond; C ₆ ~ C ₆₀ Arylene group; And C ₂ ~ C ₆₀ It may be selected from any one of a heterocyclic group.

Y ₁ is O (oxygen); S (sulfur); C ₁ -C ₂₀ Alkylene group; C ₆ ~ C ₂₄ heteroarylene group; C ₇ ~ C ₂₄ arylalkylene group; C ₂ ~ C ₂₀ Alkenylene group; C ₆ ~ C ₂₄ may be selected from any one of the arylene groups.

L ₁ ′ is a single bond; C ₆ ~ C ₂₄ Arylene group; C ₁ ~ C ₃₀ Alkylene group; And C ₆ ~ C _24, It may be selected from any of the aryloxy group.

X ₁ is O; S; NR'; C ₁ ~ C ₂₀ alkyl group; C ₆ ~ C ₂₄ aryl group; C ₂ ~ C ₂₀ may be selected from any of the alkenyl groups.

R ₁ ′ is hydrogen; heavy hydrogen; Tritium; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₁ ~ C ₂₀ Alkoxy group; It may be selected from any of hydroxy groups.

n1 and n2 may be integers of 0 to 2, respectively.

The A ring, B ring, R ₁ to R ₆ , R'and R'', Ar ₁ , L ₁ , Y ₁ , L ₁ ', X ₁ , R ₁ 'are the aryl group, heterocyclic group, fused, respectively A cyclic group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an allyloxy group, an allylalkyl group, an alkenyl group, an alkenylaryl group, a cycloalkyl group, an arylalkoxyl group, an arylalkenyl group, an alkoxylcarbonyl group, an arylene group, In the case of an alkylene group, heteroarylene group, arylalkylene group or alkenylene group, each of these is halogen; heavy hydrogen; C ₆ ~ C ₂₀ aryl group substituted or unsubstituted silane group; Siloxane groups; Cyano group; Nitro group; C ₁ ~ C ₃₀ alkylthio group; C ₁ ~C ₃₀ Alkoxy group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkynyl group; C ₆ ~ C ₃₀ Aryl group; C ₆ ~ C ₃₀ aryl group substituted with deuterium; C ₂ ~ C ₃₀ heterocyclic group; C ₃ ~ C ₃₀ cycloalkyl group; C ₇ ~ C ₃₀ arylalkyl group and C ₈ ~ C ₃₀ aryl alkenyl group may be further substituted with one or more substituents selected from the group consisting of, these substituents may combine with each other to form a ring.

The'ring' refers to a fused ring consisting of an aliphatic ring having 3 to 20 carbon atoms, an aromatic ring having 6 to 20 carbon atoms, a heterocycle having 2 to 20 carbon atoms, or a combination thereof, and a saturated or unsaturated ring.

Here, in the case of the aryl group, the number of carbon atoms may be 6 to 60, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, and in the case of the heterocyclic group, 2 to 60 carbon atoms, preferably 2 to 2 carbon atoms. 30, More preferably, it may be a heterocyclic group having 2 to 20 carbon atoms, and in the case of the alkyl group, 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 20 carbon atoms. It may be an alkyl group of 10.

In the case of the aforementioned allyl group or allylene group, specifically, the allyl group or allylene group is independently of each other a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, or a phenylene group, a biphenylene group, a terphenylene group, a naphth It may be a styrene group, phenanthryl group, pyrene or triphenylene.

The compound of Formula 1 may function as a sunscreen (A) in an encapsulant of an organic electrical device. The composition for encapsulation comprising the compound of Formula 1 may form an encapsulation layer having excellent UV blocking performance.

The composition for sealing an organic light emitting device according to the present invention may include two or more types of compounds represented by the formula (1). For example, the composition for sealing an organic light-emitting device according to the present invention includes a compound (A) represented by Formula 1, and further includes at least one compound represented by Formula 1 and different from the compound (A). Can be.

The compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 5.

In Chemical Formulas 2 to 5, R ₁ to R ₆ , R', R'', Ar ₁ , L ₁ , Y ₁ , L ₁ ', X ₁ , R ₁ ', A ₁ , A ring, B ring, o, p and n are the same as defined in the description of Formula 1 above.

The compound represented by Chemical Formula 1 may be represented by one of the following Chemical Formulas a-1 to a-15.

In Formulas a-1 to a-15, R ₁ , R ₂ , X, A ₁ , o, p, and n are the same as defined in the description of Formula 1.

When using a compound represented by any one of the formulas a-1 to a-15, it is possible to provide an encapsulation layer having excellent UV protection.

The compound represented by Formula 1 may be one or more of the following compounds, but the compound represented by Formula 1 is not limited to the compounds of the following Formula.

The composition for encapsulating an organic light emitting device according to the present invention may include one or more compounds represented by Formula 1, and based on the total solids contained in the composition, the total weight of the compounds represented by Formula 1 is 1 weight % To 10% by weight, 1% to 8% by weight, or 1% to 6% by weight. By including the compound represented by the formula (1) in the above content range, the composition for sealing of the present invention can provide an encapsulation layer having excellent UV blocking performance.

The composition for sealing an organic light emitting device according to the present invention may further include a compound (B) represented by the following Chemical Formula 6.

Hereinafter, Formula 6 will be described.

R ₇ and R ₈ are each hydrogen; heavy hydrogen; Tritium; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₁ ~ C ₆₀ Alkoxy group; It may be selected from any of hydroxy groups.

R ₉ is a C ₁ ~C ₆₀ alkylene group; C ₆ ~C ₆₀ arylene group; C ₂ ~ C ₆₀ may be selected from any one of the heterocyclic groups.

When R ₇ to R ₉ are alkyl groups, alkenyl groups, alkoxy groups, hydroxy groups, alkylene groups, arylene groups, fluorenylene groups, heterocyclic groups, each of these is halogen; Hydrogen; heavy hydrogen; C ₆ ~ C ₂₀ aryl group substituted or unsubstituted silane group; Siloxane groups; Cyano group; Nitro group; C ₁ ~ C ₃₀ alkylthio group; C ₁ ~C ₃₀ Alkoxy group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkynyl group; C ₆ ~ C ₃₀ Aryl group; C ₆ ~ C ₃₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₃₀ heterocyclic group; C ₃ ~ C ₃₀ cycloalkyl group; C ₇ ~ C ₃₀ arylalkyl group and C ₈ ~ C ₃₀ may be further substituted with one or more substituents selected from the group consisting of aryl alkenyl groups, and these substituents may also combine with each other to form a ring.

Here, in the case of the aryl group, the number of carbon atoms may be 6 to 60, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, and in the case of the heterocyclic group, 2 to 60 carbon atoms, preferably 2 to 2 carbon atoms. 30, More preferably, it may be a heterocyclic group having 2 to 20 carbon atoms, and in the case of the alkyl group, 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 20 carbon atoms. It may be an alkyl group of 10.

In the case of the aforementioned allyl group or allylene group, specifically, the allyl group or allylene group is independently of each other a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, or a phenylene group, a biphenylene group, a terphenylene group, a naphth It may be a styrene group, phenanthryl group, pyrene or triphenylene.

The composition for encapsulating the organic light-emitting device of the present invention may include a di(meth)acrylate (B) represented by Chemical Formula 6, to further increase the photo-curing rate, and to lower the viscosity, thereby facilitating deposition. For example, in Formula 6, R ₉ is a substituted or unsubstituted C ₁ to C ₆₀ alkylene group, a substituted or unsubstituted C ₆ to C ₆₀ arylene group, a substituted or unsubstituted fluorenylene group, a substitution, Or it may be an unsubstituted C ₂ ~ C ₆₀ heterocyclic group, preferably substituted or unsubstituted

C ₁ ~ C ₆₀ alkylene group, a substituted or unsubstituted C ₆ ~ C ₆₀ arylene group, more preferably a substituted or unsubstituted C ₁ ~ C ₃₀ alkylene group.

The compound represented by the formula (6), preferably di(meth)acrylate is octanediol di(meth)acrylate; Nonanediol di(meth)acrylate; Decandiol di(meth)acrylate; Undecanediol di(meth)acrylate; Dodecanediol di(meth)acrylate; Decyldi(meth)acrylate; Undecyldi(meth)acrylate; Lauryl di(meth)acrylate; Tridecyldi(meth)acrylate; Tetradecyldi(meth)acrylate; Pentadecyldi(meth)acrylate; Hexadecyldi (meth)acrylate; Heptadecyldi(meth)acrylate; Octadecyldi(meth)acrylate; Nonadecyldi(meth)acrylate; Arachidyl di (meth) acrylate may include one or more, but is not limited thereto.

The composition for encapsulating an organic light emitting device according to the present invention may include one or more compounds represented by the formula (6), and the total weight of the compounds represented by the formula (6) is 20% based on the total solids contained in the composition. % To 70% by weight, 30% to 70% by weight, or 40% to 60% by weight. By including the compound represented by the formula (6) in the above content range, the composition for sealing of the present invention can provide an encapsulation layer having excellent UV blocking performance.

The composition for sealing an organic light emitting device according to the present invention may further include a mono(meth)acrylate compound (C) represented by the following Chemical Formula 7.

Hereinafter, Formula 7 will be described.

L ₂ is a single bond; C ₁ ~ C ₆₀ alkyl group; C ₁ ~ C ₆₀ Alkylene group; C ₂ ~ C ₆₀ alkenyl group; C ₁ ~ C ₆₀ Alkoxy group; C ₆ ~ C ₆₀ Arylene group; C ₆ ~ C ₆₀ may be selected from any of the aryloxy group.

R ₁₀ is hydrogen; heavy hydrogen; Tritium; C ₁ ~ C ₆₀ alkyl group; C ₃ ~C ₃₀ cycloalkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₁ ~ C ₆₀ Alkoxy group; It may be selected from any of hydroxy groups.

R ₁₁ is a C ₆ ~C ₆₀ aryl group; C ₆ ~ C ₆₀ Allyloxy group; Fluorenyl group; C ₂ ~ C ₆₀ may be selected from any one of the heterogoro.

When L ₂ , R ₁₀ and R ₁₁ are the alkylene group, an alkyl group, an alkenyl group, an alkoxy group, an arylene group, an aryloxy group, a cycloalkyl group, a hydroxy group, an aryl group, a fluorenyl group, each of these in the case of a heterocycle halogen; heavy hydrogen; C ₆ ~ C ₂₀ aryl group substituted or unsubstituted silane group; Siloxane groups; Cyano group; Nitro group; C ₁ ~ C ₃₀ alkylthio group; C ₁ ~ C ₃₀ Alkoxy group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkynyl group; C ₆ ~ C ₃₀ Aryl group; C ₆ ~ C ₃₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₃₀ heterocyclic group; C ₃ ~ C ₃₀ cycloalkyl group; C ₇ ~ C ₃₀ arylalkyl group and C ₈ ~ C ₃₀ may be further substituted with one or more substituents selected from the group consisting of aryl alkenyl group, and these substituents may be bonded to each other to form a ring.

Here,'ring' refers to a fused ring consisting of an aliphatic ring having 3 to 20 carbon atoms, an aromatic ring having 6 to 20 carbon atoms, a hetero ring having 2 to 20 carbon atoms, or a combination thereof, and a saturated or unsaturated ring.

Here, in the case of the aryl group, the number of carbon atoms may be 6 to 60, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, and in the case of the heterocyclic group, the number of carbon atoms is 2 to 60, preferably 2 carbon atoms. ~30, more preferably may be a heterocycle having 2 to 20 carbon atoms, in the case of the alkyl group, the carbon number is 1 to 50, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably carbon number It may be an alkyl group of 1 to 10. In the case of the aforementioned aryl group or arylene group, specifically, the aryl group or arylene group is independently of each other a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group or a phenylene group, a biphenylene group, a terphenylene group, naphthyl It may be a rengi, phenanthryl group, pyrene or triphenylene.

For example, R ₁₁ is a phenylphenoxyethyl group, phenoxyethyl group, benzyl group, phenyl group, phenylphenoxy group, phenoxy group, phenylethyl group, phenylpropyl group, phenylbutyl group, methylphenylethyl group, propylphenylethyl group, methoxyphenylethyl group , Cyclohexylphenylethyl group, chlorophenylethyl group, bromophenylethyl group, methylphenyl group, methylethylphenyl group, methoxyphenyl group, propylphenyl group, cyclohexylphenyl group, chlorophenyl group, bromophenyl group, phenylphenyl group, biphenyl group, terphenyl ) Group, quaterphenyl group, anthracenyl group, naphthalenyl group, triphenylenyl group, methylphenoxy group, ethylphenoxy group, methylethylphenoxy group, methoxyphenyloxy group, propylphenoxy group, cyclohexyl group Phenoxy group, chlorophenoxy group, bromophenoxy group, biphenyloxy group, terphenyloxy group, quaterphenyloxy group, anthracenyloxy group, naphthalenyloxy group, tree It may be a phenylenyloxy (triphenylenyloxy) group.

For example, Chemical Formula 7 is preferably an aromatic mono(meth)acrylate, and is specifically as follows.

3-phenoxybenzyl (meth)acrylate; 2-phenylphenoxyethyl (meth)acrylate; Phenoxyethyl (meth) arc

Relations; 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 its structural isomers, but is not limited thereto. In addition, the (meth) acrylate mentioned in the present invention corresponds to an example but is not limited thereto, and further, the present invention includes all acrylates in a structural isomer relationship. For example, although only 2-phenylethyl (meth)acrylate is mentioned as an example of the present invention, the present invention includes at least one of 3-phenylethyl (meth)acrylate and 4-phenyl (meth)acrylate. It can, but is not limited to.

The composition for encapsulating an organic light emitting device according to the present invention may include one or more compounds represented by the formula (7), and based on the total solids contained in the composition, the total weight of the compounds represented by the formula (7) is 5 weight % To 40% by weight, 10% to 40% by weight, or 20% to 40% by weight. By including the compound represented by the formula (7) in the content range as described above, the composition for sealing of the present invention can provide an encapsulation layer having excellent UV blocking performance.

The composition for encapsulation including Formula 1 according to the present invention can form an organic barrier layer positioned between inorganic barrier layers for encapsulation or encapsulation of a flexible display device, and the organic barrier layer is photocured by encapsulating the composition for encapsulation. Can form.

The composition for sealing (organic barrier layer material) may be applied using a method such as vapor deposition, spin coating, slit coating, etc., and an initiator (D) may be used during photocuring.

The initiator may include, without limitation, a conventional photopolymerization initiator capable of performing a photocurable reaction. For example, the photopolymerization initiator may include triazine-based, acetophenone-based, benzophenone-based, thioxanthone-based, benzoin-based, phosphorus-based, oxime-based, or mixtures thereof.

As a triazine system, 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloro methyl)-s-triazine, 2-(3',4'-dimethoxy sty Reel)-4,6-bis(trichloro methyl)-s-triazine, 2-(4'-methoxy naphthyl)-4,6-bis(trichloro methyl)-s-triazine, 2-( p-methoxy phenyl)-4,6-bis(trichloro methyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloro methyl)-s-triazine, 2-bi Phenyl-4,6-bis(trichloro methyl)-s-triazine, bis(trichloro methyl)-6-styryl-s-triazine, 2-(naphtho-1-yl)-4,6- Bis(trichloro methyl)-s-triazine, 2-(4-methoxy naphtho-1-yl)-4,6-bis(trichloro methyl)-s-triazine, 2,4-trichloro methyl (Piperonyl)-6-triazine, 2,4-(trichloro methyl(4'-methoxy styryl)-6-triazine or mixtures thereof.

As the acetophenone type, 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methyl propiophenone, pt-butyl trichloro acetophenone, pt-butyl dichloro Acetophenone, 4-chloro

Acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholino propan-1-one, 2-benzyl-2- Dimethyl amino-1-(4-morpholino phenyl)-butan-1-one, or mixtures thereof.

Examples of benzophenones include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylate benzophenone, 4,4'-bis(dimethyl amino)benzophenone, 4,4'-dichloro benzo Phenone, 3,3'-dimethyl-2-methoxy benzophenone or mixtures thereof.

Examples of the thioxanthone series include thioxanthone, 2-methyl thioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2-chloro thioxanthone or Can be a mixture of these.

The benzoin system may be benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, or mixtures thereof.

The phosphorus system may be bisbenzoylphenyl phosphine oxide, benzoyldiphenyl phosphine oxide, or a mixture thereof.

Examples of the oxime system include 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione and 1-(o-acetyloxime)-1-[9-ethyl-6-( 2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, or mixtures thereof.

The initiator may be included in an amount of 0.1 to 20% by weight, 0.5 to 20% by weight, 0.5 to 10% by weight, 1 to 10% by weight, or 0.5 to 7% by weight in the composition based on solid content. In the above range, photopolymerization may occur sufficiently during exposure, and it is possible to prevent a decrease in transmittance due to an unreacted initiator remaining after photopolymerization.

In addition, the composition for sealing an organic light emitting device according to the present invention may further include a light stabilizer.

In the present invention, the light stabilizer does not have the ability to absorb ultraviolet rays by itself, but means a light stabilizer that coexists with a material that absorbs ultraviolet rays and has a light stabilizing effect, and may include a conventional light stabilizer.

For example, the light stabilizer may include cyanoacrylate-based, hindered amine-based, metal complex-based salts, or mixtures thereof.

For example, the cyanoacrylate system is ethyl 2-cyano-3.3-diphenylacrylate, 2-ethylhexyl 2-cyano-3,3-diphenylacrylate, hexyl 2-cyano-3,3- Diphenylacrylate, octyl 2-cyano-3-(4-methoxyphenyl)-3-phenylacrylate or mixtures thereof.

For example, the hindered amine system is tetrakis[methylene 3-(3,5-di-tert-butyl-4-hindioxyphenyl)propionate]methane, thiodiethylene bis[3(3,5-di- Tert-butyl-4-hindioxyphenyl)propionate], octadecyl-3-(3,5-di-tert-butyl-4-hindioxyphenyl)propionate, isotridecyl-3-(3, 5-di-tth butyl-4-hindioxyphenyl)propionate, hexamethyl (3,5-di-tert-butyl-4-hydroxydrocinamide), iso-octyl-3-(3,5 -Di-tert-butyl-4-hydroxyphenyl)propionate or mixtures thereof.

The metal complex salt system is 2,2'-thiobis(4-tert-octylphenolate)]-n-butylamine nickel(II), nickel bis[monoethyl(3,5-di-tert-butyl-4-hydride) Hydroxybenzyl)phosphonate] or mixtures thereof.

The photostabilizer may be included in the composition of 0.1 to 10% by weight, preferably 0.1 to 5% by weight, more preferably 0.1 to 3% by weight. When the composition for encapsulating the organic light emitting device in the above range is exposed to ultraviolet light for a long time, the function of the ultraviolet absorber can be maintained for a long time.

Formation of the organic barrier layer using photocuring is performed by coating the composition for sealing with 0.1 to 20 μm, preferably 1 to 15 μm, most preferably 1 to 10 μm, and irradiating at 10 to 500 ㎽/㎠ for 1 to 60 seconds. Can be cured. At this time, the curing rate may be 90% or more, and preferably 93% or more. At this time, the composition and the initiator that do not participate in the photocuring reaction in the organic barrier layer are minimized, and the pass-way of moisture and/or oxygen is suppressed, so that it can have good barrier properties.

In addition, when curing the composition for sealing (when forming the organic barrier layer), the coated sealing composition may shrink, the shrinkage is about 1-20%, more preferably 1-15% Can be

When the shrinkage rate of the organic barrier layer is 20% or more, due to oxygen and/or moisture penetration into the inorganic barrier layer

Dark spots and pixel shrinkage occur, and also two or more layers

When the organic/inorganic multilayer barrier layer is formed, warpage may occur, which may lead to the combination of light emitting elements.

The inorganic barrier layer and the organic barrier layer may be deposited by sputtering, chemical vapor deposition (CVD), plasma chemical vapor deposition (PECVD), evaporation, sublimation, inkjet, and combinations thereof.

The multi-layer barrier layer includes the organic barrier layer and the inorganic barrier layer, but may be alternately deposited, the number of barrier layers is not limited, and the number of barrier layers is permeable to oxygen and/or moisture and/or chemicals It can be changed depending on the level.

The organic barrier layer and the inorganic barrier layer may be alternately deposited in one layer or more and ten layers or less, respectively, and preferably one layer or more and three layers or less.

Hereinafter, examples of the synthesis of the compound represented by Chemical Formula 1 according to the present invention and the manufacturing example of the organic electric device will be specifically described with reference to Examples, but the present invention is not limited to the following Examples.

The compound (Final products) according to the present invention is synthesized by the following reaction scheme, and the synthesis method is not limited thereto.

<Scheme 1>

Synthesis examples of specific compounds are as follows.

I. Synthesis of Sub 1

Sub 1 of Reaction Scheme 1 may be synthesized by the reaction route of Reaction Scheme 2 below, but is not limited thereto.

<Reaction Scheme 2>

Synthesis examples of specific compounds belonging to Sub 1 are as follows.

1. Sub 1-2 synthesis example

<Scheme 3>

Starting material 2-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (30 g, 75.16 mmol) 2-hydroxyethyl acrylate (8.72 g, 75.16 mmol) was dissolved in Acetonitrile (375 ml) in a round-bottom flask, triethylamine (37.36 g, 255.48 mmol) was added and stirred at 80°C. After the reaction is completed, the mixture is extracted with ethyl acetate and water, and the organic layer is dried over MgSO ₄ and concentrated. The concentrated compound was subjected to Silicagel column to obtain 23.50 g of product (yield 72%).

2. Sub 1-6 Synthesis Example

<Reaction Scheme 4>

Starting material 2-(9-bromo-7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (30.00 g, After dissolving 66.78 mmol) and 2-hydroxyethyl acrylate (7.75 g, 66.78 mmol) in Acetonitrile (330 ml) in a round-bottom flask, Triethylamine (29.29 g, 200.34 mmol) was used to synthesize the product 21.02 g ( Yield 65%).

3. Sub 1-10 Synthesis Example

<Reaction Scheme 5>

Start 2-(7-bromo-9,9-diphenyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (30 g, 57.33 mmol) and 2 After dissolving -hydroxyethyl acrylate (6.65 g, 57.33 mmol) in Acetonitrile (300 ml) in a round bottom flask, Triethylamine (25.12 g, 171.99 mmol) was added to the product 24 g (75% yield) using the above Sub1-2 synthesis method. Got.

4. Sub 1-20 Synthesis Example

<Scheme 6>

Start 5-(7-bromodibenzo[b,d]furan-3-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (30 g, 66.49 mmol) and 2-hydroxyethyl acrylate (7.72 g, 66.49 mmol) were dissolved in acetonitrile (330 ml) in a round-bottom flask, and then triethylamine (29.17 g, 199.47 mmol) was added to the product 18.72 g ( Yield 69%).

5. Sub 1-26 Synthesis Example

<Scheme 7>

Start 2-(9-bromodinaphtho[2,1-b:1',2'-d]furan-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (30 g, 63.40 mmol) and 2-hydroxyethyl acrylate (7.36 g, 63.40 mmol) were dissolved in acetonitrile (320 ml) in a round-bottom flask, and then triethylamine (27.81 g, 190.2 mmol) was used to synthesize 23.52 g of the product using the above Sub1-2 synthesis method. (Yield 73%).

6. Sub 1-28 Synthesis Example

<Scheme 8>

Starting 2-(7-bromodibenzo[b,d]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (30 g, 77.09 mmol) and 2-hydroxyethyl acrylate ( 8.95 g, 77.09 mmol) was dissolved in Acetonitrile (385 ml) in a round bottom flask, and triethylamine (33.82 g, 231.27 mmol) was obtained using the above Sub1-2 synthesis method to obtain 26.49 g of product (yield 81%).

7. Sub 1-31 Synthesis Example

<Scheme 9>

Starting with 2-(5-bromobenzo[b]naphtho[1,2-d]thiophen-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (30 g, 68.31 mmol) After dissolving 2-hydroxyethyl acrylate (7.93 g, 68.31 mmol) in Acetonitrile (340 ml) in a round-bottomed flask, Triethylamine (29.96 g, 204.93 mmol) was used as the Sub1-2 synthesis method to yield 18.79 g of product (58% yield). ).

8. Sub 1-36 Synthesis Example

<Reaction Scheme 10>

Starting 2-bromo-9-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (30 g, 66.93 mmol) and 2-hydroxyethyl After acrylate (7.71 g, 66.93 mmol) was dissolved in acetonitrile (330 ml) in a round-bottom flask, Triethylamine (29.36 g, 200.79 mmol) was obtained using the Sub1-2 synthesis method to obtain 21.35 g of product (yield 66%).

9. Sub 1-45 Synthesis Example

<Scheme 11>

Start 9-bromo-7-butyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo[c]carbazole (30 g, 62.73 mmol) And 2-hydroxyethyl acrylate (7.28 g, 62.73 mmol) were dissolved in acetonitrile (300 ml) in a round bottom flask, and then triethylamine (27.52 g, 188.19 mmol) was added to the product 28.66 g (yield 89%) using the above Sub1-2 synthesis method. ).

Meanwhile, the compound belonging to Sub 1 may be the following compound, but is not limited thereto, and Table 1 shows the FD-MS value of the compound belonging to Sub 1.

compound FD-MS compound FD-MS Sub 1-1 m/z= 320.19 (C ₂₁ H ₂₅ BO ₂ =320.24) Sub 1-2 m/z=434.23 (C ₂₆ H ₃₁ BO ₅ =434.34) Sub 1-3 m/z= 432.25 (C ₂₇ H ₃₃ BO ₄ =432.37) Sub 1-4 m/z=370.21 (C ₂₅ H ₂₇ BO ₂ =370.30) Sub 1-5 m/z=484.24 (C ₃₀ H ₃₃ BO ₅ =484.40) Sub 1-6 m/z= 484.24 (C ₃₀ H ₃₃ BO ₅ =484.40) Sub 1-7 m/z=482.26 (C ₃₁ H ₃₅ BO ₄ =482.43) Sub 1-8 m/z=534.26 (C ₃₄ H ₃₅ BO ₅ = 534.46) Sub 1-9 m/z=444.23 (C ₃₁ H ₂₉ BO ₂ =444.38) Sub 1-10 m/z=558.26 (C ₃₆ H ₃₅ BO ₅ =558.48) Sub 1-11 m/z= 556.28 (C ₃₇ H ₃₇ BO ₄ =556.51) Sub 1-12 m/z=494.24 (C ₃₅ H ₃₁ BO ₂ =494.44) Sub 1-13 m/z=606.26 (C ₄₀ H ₃₅ BO ₅ =606.53) Sub 1-14 m/z=606.26 (C ₄₀ H ₃₅ BO ₅ =606.53) Sub 1-15 m/z=593.25 (C ₃₉ H ₃₄ BO ₅ =593.51) Sub 1-16 m/z=606.29 (C ₄₁ H ₃₉ BO ₄ =606.57) Sub 1-17 m/z=658.29 (C ₄₄ H ₃₉ BO ₅ =658.60) Sub 1-18 m/z=608.27 (C ₄₀ H ₃₇ BO ₅ =608.54) Sub 1-19 m/z=:294.14 (C ₁₈ H ₁₉ BO ₃ =294.16) Sub 1-20 m/z=408.17 (C ₂₃ H ₂₅ BO ₆ =408.26) Sub 1-21 m/z= 406.20 (C ₂₄ H ₂₇ BO ₅ )=406.29) Sub 1-22 m/z=458.19 (C ₂₇ H ₂₇ BO ₆ =458.32) Sub 1-23 m/z=344.16 (C ₂₂ H ₂₁ BO ₃ =344.22) Sub 1-24 m/z=458.19 (C ₂₇ H ₂₇ BO ₆ =458.32) Sub 1-25 m/z=456.21 (C ₂₈ H ₂₉ BO ₅ = 456.35) Sub 1-26 m/z=508.21 (C ₃₁ H ₂₉ BO ₆ =508.38) Sub 1-27 m/z=310.12 (C ₁₈ H ₁₉ BO ₂ S=310.22) Sub 1-28 m/z=424.15 (C ₂₃ H ₂₅ BO ₅ S=424.32) Sub 1-29 m/z=422.17 (C ₂₄ H ₂₇ BO ₄ S=422.35) Sub 1-30 m/z=360.14 (C ₂₂ H ₂₁ BO ₂ S=360.28) Sub 1-31 m/z=474.17 (C ₂₇ H ₂₇ BO ₅ S=474.38) Sub 1-32 m/z=474.17 (C ₂₇ H ₂₇ BO ₅ S=474.38) Sub 1-33 m/z=472.19 (C ₂₈ H ₂₉ BO ₄ S)= 472.41) Sub 1-34 m/z=524.18 (C ₃₁ H ₂₉ BO ₅ S=524.44) Sub 1-35 m/z=369.19 (C ₂₄ H ₂₄ BNO ₂ =369.27) Sub 1-36 m/z=483.22 (C ₂₉ H ₃₀ BNO ₅ =483.37) Sub 1-37 m/z=481.24 (C ₃₀ H ₃₂ BNO ₄ =481.40) Sub 1-38 m/z=533.24 (C ₃₃ H ₃₂ BNO ₅ =533.43) Sub 1-39 m/z=419.21 (C ₂₈ H ₂₆ BNO ₂ =419.33) Sub 1-40 m/z=533.24 (C ₃₃ H ₃₂ BNO ₅ = 533.43) Sub 1-41 m/z=583.25 (C ₃₇ H ₃₄ BNO ₅ =583.49) Sub 1-42 m/z=533.24 (C ₃₃ H ₃₂ BNO ₅ = 533.43) Sub 1-43 m/z=531.26 (C ₃₄ H ₃₄ BNO ₄ = 531.46) Sub 1-44 m/z=583.25 (C ₃₇ H ₃₄ BNO ₅ =583.49) Sub 1-45 m/z=513.27 (C ₃₁ H ₃₆ BNO ₅ )= 513.44)

II. Product synthesis

1. Synthesis Example of P1-2

<Reaction Scheme 12>

Starting materials 1-(5-bromo-2-hydroxyphenyl)-3H-imidazo[5,1-a]isoindole-3,5(9bH)-dione (10.00 g, 27.99 mmol) and 2-((9,9 Round -dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl)oxy)ethyl acrylate (12.15 g, 27.99 mmol) After dissolving in bottom flask with Toluene (140 ml) and H ₂ O (70 ml), K ₂ CO ₃ (11.58 g, 83.97 mmol), Pd(PPh ₃ ) ₄ (1.61 g, 1.39 mmol) was added and stirred at 110 ^° C. After the reaction was completed, extracted with CH ₂ Cl ₂ and water, the organic layer was dried over MgSO ₄ , concentrated, and the resulting compound was silicagel column to obtain 12.27 g of product (yield: 75%).

2. Synthesis Example of P1-15

<Scheme 13>

Starting material 1-(3'-bromo-4-hydroxy-[1,1'-biphenyl]-3-yl)-3H-imidazo[5,1-a]isoindole-3,5(9bH)-dione ( 10 g, 23.08 mmol) and 2-((7,7-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo[c]fluoren -9-yl)oxy)ethyl acrylate (11.17 g, 23.08 mmol), Pd(PPh ₃ ) ₄ (1.33 g, 1.15 mmol), K ₂ CO ₃ (9.55 g, 69.24 mmol), Toluene (110 ml), and H ₂ O (50 ml) were obtained using the above P-2 synthesis method to obtain 10.17 g (yield: 62%) of the product.

3. Synthesis of P1-22

<Reaction Scheme 14>

Starting materials 1-(4-bromo-2-hydroxyphenyl)-3H-imidazo[5,1-a]isoindole-3,5(9bH)-dione (10 g, 27.99 mmol) and 2-((9,9 -diphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl)oxy)ethyl acrylate (15.63 g, 27.99 mmol), Pd (PPh ₃ ) ₄ (1.61 g, 1.39 mmol), K ₂ CO ₃ (11.58 g, 83.97 mmol), Toluene (140 ml), H ₂ O (70 ml) was obtained using the above P-2 synthesis method to obtain 17.45 g (yield: 88%) of the product.

4. Synthesis of P1-28

<Reaction Scheme 15>

Starting materials 1-(2-bromo-5-hydroxypyridin-4-yl)-3H-imidazo[5,1-a]isoindole-3,5(9bH)-dione (10 g, 27.92 mmol) and 2-( (9,9-diphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl)oxy)ethyl acrylate (15.59 g, 27.92 mmol), Pd(PPh ₃ ) ₄ (1.61 g, 1.39 mmol), K ₂ CO ₃ (11.55 g, 83.76 mmol), Toluene (140 ml), H ₂ O (70 ml) was obtained 11.48 g (yield: 58%) of the product using the above P-2 synthesis method.

5. P1-45 Synthesis Example

<Reaction Scheme 16>

Starting material 1-(4-(5-bromopyrimidin-2-yl)-2-hydroxyphenyl)-3H-imidazo[5,1-a]isoindole-3,5(9bH)-dione (10 g, 22.97 mmol) And 2-((7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-3-yl)oxy)ethyl acrylate (9.37 g, 22.97 mmol), Pd(PPh ₃ ) ₄ (1.32 g, 1.14 mmol), K ₂ CO ₃ (9.50 g, 68.91 mmol), Toluene (110 ml), H ₂ O (50 ml), was obtained by using the above P-2 synthesis method to obtain 13.45 g (yield: 92%) of the product.

6. Synthesis Example of P1-57

<Reaction Scheme 17>

Starting material 1-(4'-((4-bromophenyl)(phenyl)amino)-4-hydroxy-[1,1'-biphenyl]-3-yl)-3H-imidazo[5,1-a]isoindole -3,5(9bH)-dione (10 g, 16.65 mmol) and 2-((9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dinaphtho[2, 1-b:1',2'-d]furan-5-yl)oxy)ethyl acrylate (8.46 g, 16.65 mmol), Pd(PPh ₃ ) ₄ (0.96 g, 0.83 mmol), K ₂ CO ₃ (6.89 g, 49.95 mmol), Toluene (100 ml), H ₂ O (50 ml), was obtained by using the above P-2 synthesis method to obtain 11.26 g (yield: 75%) of the product.

7. Synthesis Example of P1-69

<Reaction Scheme 18>

Starting material 1-(5-(4-bromo-6-phenyl-1,3,5-triazin-2-yl)-2-hydroxyphenyl)-3H-imidazo[5,1-a]isoindole-3,5 (9bH)-dione (10 g, 19.51 mmol) and 2-((7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]thiophen- 3-yl)oxy)ethyl acrylate (8.27 g, 19.51 mmol), Pd(PPh ₃ ) ₄ (1.12 g, 0.97 mmol), K ₂ CO ₃ (8.07 g, 58.53 mmol), Toluene (100 ml), H ₂ O (50 ml), was obtained by using the above P-2 synthesis method to obtain 11.10 g (yield: 78%) of the product.

8. P1-72 Synthesis Example

<Scheme 19>

Starting materials 1-(4-bromo-2-hydroxyphenyl)-3H-imidazo[5,1-a]isoindole-3,5(9bH)-dione (10 g, 27.99 mmol) and 2-((9-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]naphtho[1,2-d]thiophen-5-yl)oxy)ethyl acrylate (13.27 g, 27.99 mmol ), Pd(PPh ₃ ) ₄ (1.61 g, 1.39 mmol), K ₂ CO ₃ (11.58 g, 83.97 mmol), Toluene (140 ml), H ₂ O (70 ml), was obtained by using the above P-2 synthesis method to obtain 11.71 g (yield: 67%) of the product.

9. P1-82 Synthesis Example

<Reaction Scheme 20>

Starting materials 1-(4-bromo-2-hydroxyphenyl)-3H-imidazo[5,1-a]isoindole-3,5(9bH)-dione (10 g, 27.99 mmol) and 2-((9-phenyl -7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazol-2-yl)oxy)ethyl acrylate (13.52 g, 27.99 mmol), Pd(PPh ₃ ) ₄ (1.61 g, 1.39 mmol), K ₂ CO ₃ (11.58 g, 83.97 mmol), Toluene (140 ml), H ₂ O (70 ml), and 13.82 g (Yield: 78%) of the product were obtained by using the above P-2 synthesis method.

10. Synthesis of P1-99

<Reaction Scheme 21>

Starting material 1-(5-(4-bromo-6-phenyl-1,3,5-triazin-2-yl)-2-hydroxyphenyl)-3H-imidazo[5,1-a]isoindole-3,5 (9bH)-dione (10 g, 19.51 mmol) and 2-((7-butyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo [c]carbazol-9-yl)oxy)ethyl acrylate (10.01 g, 19.51 mmol), Pd(PPh ₃ ) ₄ (1.12 g, 0.97 mmol), K ₂ CO ₃ (8.07 g, 58.53 mmol), Toluene (100 ml), H ₂ O (50 ml), was obtained by using the above P-2 synthesis method to obtain 12.46 g (yield: 78%) of the product.

On the other hand, FD-MS values of the compounds P-1 to P-100 of the present invention prepared according to the above synthesis example are shown in Table 2 below.

compound FD-MS compound FD-MS P-1 m/z=470.16 (C ₃₁ H ₂₂ N ₂ O ₃ =470.53) P-2 m/z=584.19 (C ₃₆ H ₂₈ N ₂ O ₆ =584.63) P-3 m/z=660.23 (C ₄₂ H ₃₂ N ₂ O ₆ =660.73) P-4 m/z=710.24 (C ₄₆ H ₃₄ N ₂ O ₆ =710.79) P-5 m/z=662.22 (C ₄₀ H ₃₀ N ₄ O ₆ =662.70) P-6 m/z=582.22 (C ₃₇ H ₃₀ N ₂ O ₅ =582.66) P-7 m/z=827.30 (C ₅₄ H ₄₁ N ₃ O ₆ =827.94) P-8 m/z=585.19 (C ₃₅ H ₂₇ N ₃ O ₆ =585.62) P-9 m/z=739.24 (C ₄₅ H ₃₃ N ₅ O ₆ =739.79) P-10 m/z=600.19 (C ₃₆ H ₂₈ N ₂ O ₇ =600.63) P-11 m/z=520.18 (C ₃₅ H ₂₄ N ₂ O ₃ =520.59) P-12 m/z= 634.21 (C ₄₀ H ₃₀ N ₂ O ₆ =634.69) P-13 m/z=710.24 (C ₄₆ H ₃₄ N ₂ O ₆ =710.79) P-14 m/z=760.26 (C ₅₀ H ₃₆ N ₂ O ₆ =760.85) P-15 m/z=710.24 (C ₄₆ H ₃₄ N ₂ O ₆ =710.79) P-16 m/z=632.23 (C ₄₁ H ₃₂ N ₂ O ₅ =632.72) P-17 m/z=927.33 (C ₆₂ H ₄₅ N ₃ O ₆ =928.06) P-18 m/z=635.21 (C ₃₉ H ₂₉ N ₃ O ₆ =635.68) P-19 m/z=789.26 (C ₄₉ H ₃₅ N ₅ O ₆ =789.85) P-20 m/z=650.21 (C ₄₀ H ₃₀ N ₂ O ₇ =650.69) P-21 m/z=594.19 (C ₄₁ H ₂₆ N ₂ O ₃ =594.67) P-22 m/z=708.23 (C ₄₆ H ₃₂ N ₂ O ₆ =708.77) P-23 m/z=784.26 (C ₅₂ H ₃₆ N ₂ O ₆ =784.87) P-24 m/z=834.27 (C ₅₆ H ₃₈ N ₂ O ₆ =834.93) P-25 m/z=786.25 (C ₅₀ H ₃₄ N ₄ O ₆ =786.84) P-26 m/z=706.25 (C ₄₇ H ₃₄ N ₂ O ₅ =706.80) P-27 m/z=951.33 (C64H45N3O6=952.08) P-28 m/z=709.22 (C45H31N3O6=709.76) P-29 m/z=863.27 (C ₅₅ H ₃₇ N ₅ O ₆ =863.93) P-30 m/z=724.22 (C ₄₆ H ₃₂ N ₂ O ₇ =724.77) P-31 m/z=644.21 (C ₄₅ H ₂₈ N ₂ O ₃ =644.73) P-32 m/z=756.23 (C ₅₀ H ₃₂ N ₂ O ₆ =756.81) P-33 m/z=832.26 (C ₅₆ H ₃₆ N ₂ O ₆ =832.91) P-34 m/z=884.29 (C ₆₀ H ₄₀ N ₂ O ₆ =884.99) P-35 m/z=832.26 (C ₅₆ H ₃₆ N ₂ O ₆ =832.91) P-36 m/z=756.26 (C ₅₁ H ₃₆ N ₂ O ₅ S=756.86) P-37 m/z=1051.36 (C ₇₂ H ₄₉ N ₃ O ₆ =1052.20) P-38 m/z=759.24 (C ₄₉ H ₃₃ N ₃ O ₆ =759.82) P-39 m/z=913.29 (C ₅₉ H ₃₉ N ₅ O ₆ =913.99) P-40 m/z=772.22 (C ₅₀ H ₃₂ N ₂ O ₇ =772.81) P-41 m/z=444.11 (C ₂₈ H ₁₆ N ₂ O ₄ =444.45) P-42 m/z=558.14 (C ₃₃ H ₂₂ N ₂ O ₇ =558.55) P-43 m/z=634.17 (C ₃₉ H ₂₆ N ₂ O ₇ =634.64) P-44 m/z=684.19 (C ₄₃ H ₂₈ N ₂ O ₇ =684.70) P-45 m/z=636.16 (C ₃₇ H ₂₄ N ₄ O ₇ =636.62) P-46 m/z=556.16 (C ₅₇ H ₄₃ NO ₆ =556.57) P-47 m/z=801.25 (C ₅₁ H ₃₅ N ₃ O ₇ =801.86) P-48 m/z=559.14 (C ₃₂ H ₂₁ N ₃ O ₇ =559.53) P-49 m/z=713.19 (C ₄₂ H ₂₇ N ₅ O ₇ =713.71) P-50 m/z=574.14 (C ₃₃ H ₂₂ N ₂ O ₈ =574.55) P-51 m/z=494.13 (C ₃₂ H ₁₈ N ₂ O ₄ =494.51) P-52 m/z= 608.16 (C ₃₇ H ₂₄ N ₂ O ₇ =608.61) P-53 m/z=684.19 (C ₄₃ H ₂₈ N ₂ O ₇ =684.70) P-54 m/z=734.21 (C ₄₇ H ₃₀ N ₂ O ₇ =734.76) P-55 m/z=684.19 (C ₄₃ H ₂₈ N ₂ O ₇ =684.70) P-56 m/z=606.18 (C ₃₈ H ₂₆ N ₂ O ₆ =606.63) P-57 m/z=901.28 (C ₆₀ H ₄₃ NO ₃ =901.98) P-58 m/z=609.15 (C ₃₆ H ₂₃ N ₃ O ₇ =609.59) P-59 m/z=763.21 (C ₄₆ H ₂₉ N ₅ O ₇ =763.77) P-60 m/z=624.15 (C ₃₇ H ₂₄ N ₂ O ₈ =624.61) P-61 m/z=460.09 (C ₂₈ H ₁₆ N ₂ O ₃ S=460.51) P-62 m/z=574.12 (C ₃₃ H ₂₂ N ₂ O ₆ S=574.61) P-63 m/z=650.15 (C ₃₉ H ₂₆ N ₂ O ₆ S=650.71) P-64 m/z=700.17 (C ₄₃ H ₂₈ N ₂ O ₆ S=700.77) P-65 m/z=652.14 (C ₃₇ H ₂₄ N ₄ O ₆ S=652.68) P-66 m/z=572.14 (C ₃₄ H ₂₄ N ₂ O ₅ S=572.64) P-67 m/z=817.22 (C ₅₁ H ₃₅ N ₃ O ₆ S=817.92) P-68 m/z=575.12 (C ₃₂ H ₂₁ N ₃ O ₆ S=575.60) P-69 m/z=729.17 (C ₄₂ H ₂₇ N ₅ O ₆ S=729.77) P-70 m/z=590.11 (C ₃₃ H ₂₂ N ₂ O ₇ S)=590.61) P-71 m/z=510.10 (C ₃₂ H ₁₈ N ₂ O ₃ S=510.57) P-72 m/z=624.14 (C ₃₇ H ₂₄ N ₂ O ₆ S=624.67) P-73 m/z=700.17 (C ₄₃ H ₂₈ N ₂ O ₆ S=700.77) P-74 m/z=750.18 (C ₄₇ H ₃₀ N ₂ O ₆ S=750.83) P-75 m/z=777.19 (C ₄₃ H ₂₈ N ₂ O ₆ S=777.85) P-76 m/z=622.16 (C ₃₈ H ₂₆ N ₂ O ₅ S=622.70) P-77 m/z=917.26 (C ₅₉ H ₃₉ N ₃ O ₆ S=918.04) P-78 m/z=625.13 (C ₃₆ H ₂₃ N ₃ O ₆ S=625.66) P-79 m/z=779.18 (C ₄₆ H ₂₉ N ₅ O ₆ S=779.83) P-80 m/z=640.13 (C ₃₇ H ₂₄ N ₂ O ₇ S=640.67) P-81 m/z=519.16 ( _C34 H ₂₁ N ₃ O ₃ =519.56) P-82 m/z=633.19 (C ₃₉ H ₂₇ N3O ₆ =633.66) P-83 m/z=709.22 (C ₄₅ H ₃₁ N ₃ O ₆ =709.76) P-84 m/z=759.24 (C ₄₉ H ₃₃ N ₃ O ₆ =759.82) P-85 m/z=711.21 (C ₄₃ H ₂₉ N ₅ O ₆ =711.73) P-86 m/z=631.21 (C ₄₀ H ₂₉ N ₃ O ₅ =631.69) P-87 m/z=926.31 (C ₆₁ H ₄₂ N ₄ O ₆ =927.03) P-88 m/z=634.19 (C ₃₈ H ₂₆ N ₄ O ₆ =634.65) P-89 m/z=788.24 (C ₄₈ H ₃₂ N ₆ O ₆ =788.82) P-90 m/z=649.18 (C ₃₉ H ₂₇ N ₃ O ₇ =649.66) P-91 m/z=569.17 (C ₃₈ H ₂₃ N ₃ O ₃ =569.62) P-92 m/z=683.21 (C ₄₃ H ₂₉ N ₃ O ₆ =683.72) P-93 m/z=809.25 (C ₅₃ H ₃₅ N ₃ O ₆ =809.88) P-94 m/z=809.25 (C ₅₃ H ₃₅ N ₃ O ₆ =809.88) P-95 m/z=759.24 (C ₄₉ H ₃₃ N ₃ O ₆ =759.82) P-96 m/z=681.23 (C ₄₄ H ₃₁ N ₃ O ₅ =681.75) P-97 m/z=976.33 (C ₆₅ H ₄₄ N ₄ O ₆ =977.09) P-98 m/z=684.20 (C ₄₂ H ₂₈ N ₄ O ₆ =684.71) P-99 m/z=818.29 (C ₅₀ H ₃₈ N ₆ O ₆ =818.89) P-100 m/z=699.20 (C ₄₃ H ₂₉ N ₃ O ₇ =699.72)

Manufacturing evaluation of the composition for sealing organic light emitting devices

[Example 1]

In Example 1 (A) as an ultraviolet blocker (A1) 3.5 parts by weight of the compound P1-2 of the present invention, (B) di(meth)acrylate (B1)1,10-decanediol diacrylate (TCI) 57.4 parts by weight, (C) 36.2 parts by weight of (C1)3-phenoxybenzyl acrylate (KPX) as mono(meth)acrylate, (D) 2.0 parts by weight of Darocur TPO (BASF) as initiator and (E) As a light stabilizer, 0.9 parts by weight of CHISORB 336 (DBC) was placed in a 20 ml brown vial, and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity 16.3 cps at 25°C).

[Example 2]

In Example 1 (A) as an ultraviolet blocker (A2) 5.3 parts by weight of the compound P1-15 of the present invention, (B) di(meth)acrylate (B1)1,10-decanediol diacrylate (TCI) 54.8 parts by weight, (C) 37.0 parts by weight of (C1)3-phenoxybenzyl acrylate (KPX) as mono(meth)acrylate, (D) 2.0 parts by weight of Darocur TPO (BASF) as initiator and (E) As a light stabilizer, 0.9 parts by weight of CHISORB 336 (DBC) was placed in a 20 ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare a composition for sealing (viscosity 18.2 cps at 25°C).

[Example 3]

In Example 1 (A) as an ultraviolet blocker (A3) 5.8 parts by weight of the compound P1-22 of the present invention, (B) di(meth)acrylate (B1)1,10-decanediol diacrylate (TCI) 56.0 parts by weight, (C) mono(meth)acrylate (C1)3-phenoxybenzyl acrylate (KPX) 35.3 parts by weight, (D) initiator Darocur TPO (BASF) 2.0 parts by weight and (E) As a light stabilizer, 0.9 parts by weight of CHISORB 336 (DBC) was placed in a 20 ml brown vial, and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity 19.5 cps at 25°C).

[Example 4]

In Example 1 (A) as an ultraviolet blocker (A4) 4.2 parts by weight of the compound P1-28 of the present invention, (B) di(meth)acrylate (B1)1,10-decanediol diacrylate (TCI) 56.6 parts by weight, (C) 3(3) parts by weight of (C1)3-phenoxybenzyl acrylate (KPX) as mono(meth)acrylate, (D) 2.0 parts by weight of Darocur TPO (BASF) as initiator and (E) As a light stabilizer, 0.9 parts by weight of CHISORB 336 (DBC) was placed in a 20 ml brown vial, and mixed at room temperature for 2 hours using a shaker to prepare a composition for sealing (viscosity 17.8 cps at 25°C).

[Example 5]

In Example 1 (A) as an ultraviolet blocker (A5) 3.8 parts by weight of the compound P1-45 of the present invention, (B) di(meth)acrylate (B1)1,10-decanediol diacrylate (TCI) 55.8 parts by weight, (C) 37.5 parts by weight of (C1)3-phenoxybenzyl acrylate (KPX) as mono(meth)acrylate, (D) 2.0 parts by weight of Darocur TPO (BASF) as initiator and (E) As a light stabilizer, 0.9 parts by weight of CHISORB 336 (DBC) was placed in a 20 ml brown vial, and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity 17.2 cps at 25°C).

[Example 6]

In Example 1 (A) as an ultraviolet blocker (A6) 3.1 parts by weight of the compound P1-57 of the present invention, (B) di(meth)acrylate (B1)1,10-decanediol diacrylate (TCI) 57.3 parts by weight, (C) 36.7 parts by weight of (C1)3-phenoxybenzyl acrylate (KPX) as mono(meth)acrylate, (D) 2.0 parts by weight of Darocur TPO (BASF) as initiator and (E) As a light stabilizer, 0.9 parts by weight of CHISORB 336 (DBC) was placed in a 20 ml brown vial, and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity 16.5 cps at 25°C).

[Comparative Example 1]

In Comparative Example 1, (F) UV blocking agent (F1) TINUVIN 328 (Basf) 8.8 parts by weight, (B1) di (meth) acrylate (B1) 1,10-decanediol diacrylate (TCI) 52.9 Parts by weight, (C) 35.4 parts by weight of (C1)3-phenoxybenzyl acrylate (KPX) as mono(meth)acrylate, (D) 2.0 parts by weight of Darocur TPO (BASF) as initiator and (E) As a light stabilizer, 0.9 parts by weight of CHISORB 336 (DBC) was placed in a 20 ml brown vial, and mixed at room temperature for 2 hours using a shaker to prepare a composition for sealing (viscosity 21.6 cps at 25°C).

[Comparative Example 2]

In Comparative Example 1 (F) as an ultraviolet blocker (F2) ZIKO-460 (ZIKO) 8.8 parts by weight, (B1) di (meth) acrylate (B1) 1,10-decanediol diacrylate (TCI) 52.9 parts by weight, (C) 3 (5) parts by weight of (C1)3-phenoxybenzyl acrylate (KPX) as mono(meth)acrylate, (D) 2.0 parts by weight of Darocur TPO (BASF) as an initiator, and (E) ) As a light stabilizer, 0.9 parts by weight of CHISORB 336 (DBC) was placed in a 20 ml brown vial, and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity 26.9 cps at 25°C).

[Comparative Example 3]

In Comparative Example 1 (F) as an ultraviolet blocker (F3) Tinosorb M (Basf) 8.8 parts by weight, (B1) di (meth) acrylate (B1) 1,10-decanediol diacrylate (TCI) 52.9 Parts by weight, (C) 35.4 parts by weight of (C1)3-phenoxybenzyl acrylate (KPX) as mono(meth)acrylate, (D) 2.0 parts by weight of Darocur TPO (BASF) as initiator and (E) As a light stabilizer, 0.9 parts by weight of CHISORB 336 (DBC) was placed in a 20 ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare a composition for sealing (viscosity 28.2 cps at 25°C).

[Comparative Example 4]

In Comparative Example 1, (F) ultraviolet blocking agent (F3)CYASORB UV-24 (CYTEC) 8.8 parts by weight, (B1)di(meth)acrylate (B1)1,10-decanediol diacrylate (TCI) ) 52.9 parts by weight, (C) 35.4 parts by weight of (C1)3-phenoxybenzyl acrylate (KPX) as mono(meth)acrylate, (D) 12.0 parts by weight of Darocur TPO (BASF) as initiator and and ( E) 0.9 parts by weight of CHISORB 336 (DBC) as a light stabilizer was placed in a 20 ml brown vial, and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity 19.8 cps at 25°C).

Film formation method

Under N ₂ conditions, ₂ ml of the compositions for sealing of Examples 1 to 6 and Comparative Examples 1 to 4 were added dropwise to 50 mm X 50 mm bare glass, spin-coated, and then UV cured (1800 mJ/Cm ² ) to film 8 μm thick. Formed.

Property evaluation method

1. Transmittance

The transmittance of the visible light region was measured with Lambda950 (Perkin Elmer) for the coated and cured film.

2. Light curing rate

Photocurable composition the strength of the absorption peak in the vicinity of 1635cm-1 (C = C), 1720cm ^-1 vicinity (C = O) was measured using a FT-IR (FT / IR- 6600, Jasco , Inc.) with respect to the. Near 1635cm-1 (C = C), 1720cm ^-1 measured intensity of the absorption peak in the vicinity of the (C = O). The photocuring rate was calculated according to the following equation 1.

<Equation 1>

Light curing rate(%)= ｜1-(A/B)｜ x 100

(In the above, A is the ratio of the intensity of the absorption peak at around 1635 cm ^-1 to the intensity of the absorption peak at around 1720 cm ^-1 for the cured film, and B is at around 1720 cm ^-1 for the photocurable composition. Ratio of the intensity of the absorption peak at around 1635 cm ^-1 to the intensity of the absorption peak)

Measurement results of the composition for sealing prepared by Examples and Comparative Examples are shown in Table 3 below, and transmittance graphs are shown in FIGS. 3 and 4.

Example Comparative example One 2 3 4 5 6 One 2 3 4 A A1 3.5 - - - - - - - - - A2 - 5.3 - - - - - - - - A3 - - 5.8 - - - - - - - A4 - - - 4.2 - - - - - - A5 - - - - 3.8 - - - - - A6 - - - - - 3.1 - - - - B 57.4 54.8 56.0 56.6 55.8 57.3 52.9 52.9 52.9 52.9 C 36.2 37.0 35.3 36.3 37.5 36.7 35.4 35.4 35.4 35.4 D 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 E 0.9 0.9 0.9 0.9 0.9 0.9 0.9 0.9 0.9 0.9 F F1 - - - - - - 8.8 - - - F2 - - - - - - - 8.8 - - F3 - - - - - - - - 8.8 - F4 - - - - - - - - - 8.8 Transmittance
(%) 400nm 1.1 4.2 0.5 0.3 0.4 0.4 91.4 93.5 91.5 69.4 405nm 4.0 5.3 4.1 4.0 1.4 4.7 95.4 95.3 95.2 81.5 430nm 94.2 90.3 93.9 95.1 95.7 95.2 97.9 97.4 97.6 97.3 440nm 96.0 94.0 96.7 96.2 96.8 97.2 98.3 97.6 97.8 97.9 Light curing rate (%) 93.5 93.0 93.3 92.7 93.8 92.9 91.7 91.6 91.6 91.5 Viscosity (cps) 16.7 18.5 19.3 17.3 17.1 16.5 21.6 26.9 28.2 19.8

As can be seen by looking at the results of Table 3, in Example 1 to Example 6 using the composition containing the material of Formula 1 of the present invention A1 ~ A6 as a sunscreen as a sealing material, 0.3% ~ 400nm ~ 405nm 5.3% transmittance, it was confirmed that the transmittance of 90.3% to 97.2% at 430 nm to 440 nm, and also for the photocuring rate, 92.7% to 93.8%, and the viscosity of 16.5 cps to 19.3 cps. Could.

When comparing the results of Table 3 in more detail, only the types of sunscreens differed, and in the case of Example 1 and Comparative Example 1 to Comparative Example 4 in which all compositions and amounts were the same, Example 1 using the present invention material P1-2 It was confirmed that the exhibited a transmittance of 1.1% at 400 nm, and Comparative Examples 1 to 4 exhibited 69.4% to 91.4%. In addition, when the transmittance was confirmed at 405 nm, it was confirmed that Example 1 was 4.0% and Comparative Example 1 to Comparative Example 4 exhibited 81.5% to 95.4%. This confirmed that when the material of the present invention P1-2 was used as a sunscreen, the sunscreen performance was very superior to that of the comparative examples F1 to F4. In addition, as a result of measuring the light curing rate for use as a sealing material,

It was confirmed that both of Example 1 and Comparative Examples 1 to 4 showed a light curing rate of 90% or more.

In addition, as a result of comparing Examples 1 to 6 using the inventive material, the material having the lowest transmittance at 400 nm is the P1-28 material used at Example 4, and the material having the lowest transmittance at 405 nm is Example 5 It is a P-45 material used in.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains will be capable of various modifications without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in the present specification are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments.

The scope of protection of the present invention should be interpreted by the following claims, and all technologies within the scope equivalent thereto should be interpreted as being included in the scope of the present invention.

110: substrate
200: organic light emitting device
300: sealing layer
310: first sealing layer
320: second sealing layer

Claims (9)

Composition for encapsulating an organic light emitting device comprising a compound (A) represented by the following formula (1):

In Chemical Formula 1,
1) A ring and B ring are the same or different from each other independently, and C ₆ ~ C ₃₀ aryl group; A fused ring group of an aromatic ring of C ₆ to C ₃₀ and an aliphatic ring of C ₃ to C ₃₀ ; C ₂ ~ C ₃₅ is selected from any of the Heterogorogi,
2) R ₁ and R ₂ are each independently the same or different and deuterium; Tritium; Hydroxyl group; Halogen group; Cyano group; C ₆ ~ C ₆₀ Aryl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₁ ~ C ₆₀ alkyl group; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; C ₂ ~ C ₆₀ alkenyl group; C ₁ ~ C ₆₀ alkoxyl group; C ₆ ~ C ₆₀ Aryloxy group; C ₇ ~ C ₆₀ Arylalkyl group; C ₂ ~ C ₃₀ Alkenyloxyl group; Ether group; C ₈ ~ C ₆₀ Alkenyl aryl group; C ₃ ~ C ₆₀ cycloalkyl group; Silane group; 2siloxane groups; C ₇ ~ C ₆₀ Aryl alkoxyl group; C ₈ ~ C ₆₀ Aryl alkenyl group; And C ₂ ~ C ₆₀ It is a substituent selected from any one of the alkoxyl carbonyl group,
3) R ₁ and R ₂ are the same as or different from each other as a plurality when o and p are 2 or more, and a plurality of R ₁ and R ₂ Between Each can be combined to form a ring,
4) o is an integer from 0 to 8, p is an integer from 0 to 7,
5) R ₃ to R ₆ are each independently selected from the substituents described in 2) above, and R ₃ to R ₆ may combine with each other to form a ring,
6) X is O (oxygen), S (sulfur), NAr ₁ or CR'R",
R'and R" are C ₁ to C ₃₀ alkyl groups; C ₆ to C ₃₀ aryl groups, and R'and R" may combine with each other to form a spy compound, and Ar ₁ is C ₁ to C ₃₀ Alkyl group of; C ₆ ~ C ₆₀ Aryl group; C ₂ ~ C ₆₀ is selected from any one of the heterocyclic group,
7) L ₁ is a single bond; C ₆ ~ C ₆₀ Arylene group; And C ₂ ~ C ₆₀ is selected from any one of the heterocyclic group,
8) Y ₁ is O (oxygen); S (sulfur); C ₁ -C ₂₀ Alkylene group; C ₆ ~ C ₂₄ heteroarylene group; C ₇ ~ C ₂₄ arylalkylene group; C ₂ ~ C ₂₀ Alkenylene group; C ₆ ~ C ₂₄ is selected from any one of the arylene groups,
9) L ₁ ′ is a single bond; C ₆ ~ C ₂₄ Arylene group; C ₁ ~ C ₃₀ Alkylene group; And C ₆ ~ C _{24, It} is selected from any one of the aryloxy group,
10) X ₁ is O; S; NR'; C ₁ ~ C ₂₀ alkyl group; C ₆ ~ C ₂₄ aryl group; C ₂ ~ C ₂₀ is selected from any one of the alkenyl group,
11) R ₁ ′ is hydrogen; heavy hydrogen; Tritium; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₁ ~ C ₂₀ Alkoxy group; Selected from any one of hydroxy groups,
12) n1 and n2 are each an integer from 0 to 2,
13) The A ring, B ring, R ₁ to R ₆ , R'and R'', Ar ₁ , L ₁ , Y ₁ , L ₁ ', X ₁ , R ₁ 'are the aryl group and heterocyclic group, respectively. , Fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, allyloxy group, allylalkyl group, alkenyl group, alkenylaryl group, cycloalkyl group, arylalkoxyl group, arylalkenyl group, alkoxylcarbonyl group, aryl In the case of an alkylene group, an alkylene group, a heteroarylene group, an arylalkylene group or an alkenylene group, each of these is halogen; heavy hydrogen; C ₆ ~ C ₂₀ aryl group substituted or unsubstituted silane group; Siloxane groups; Cyano group; Nitro group; C ₁ ~ C ₃₀ alkylthio group; C ₁ ~C ₃₀ Alkoxy group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkynyl group; C ₆ ~ C ₃₀ Aryl group; C ₆ ~ C ₃₀ aryl group substituted with deuterium; C ₂ ~ C ₃₀ heterocyclic group; C ₃ ~ C ₃₀ cycloalkyl group; C ₇ ~ C ₃₀ arylalkyl group and C ₈ ~ C ₃₀ aryl alkenyl group may be further substituted with one or more substituents selected from the group consisting of, these substituents may combine with each other to form a ring.
According to claim 1,
The compound represented by Formula 1 is a composition for sealing an organic light emitting device represented by any one of the following Formulas 2 to 5:

. According to claim 1,
The compound represented by Formula 1 is a composition for sealing an organic light emitting device, characterized in that represented by one of the following formulas a-1 to a-15:

.
According to claim 1,
A composition for encapsulation of an organic light emitting device represented by Chemical Formula 1 and further comprising at least one compound different from Compound (A).
According to claim 1,
Composition for sealing an organic light emitting device further comprising a compound (B) represented by the following formula (6):

In Chemical Formula 6,
1) R ₇ and R ₈ are each hydrogen; heavy hydrogen; Tritium; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₁ ~ C ₆₀ Alkoxy group; Selected from any one of hydroxy groups,
2) R ₉ is a C ₁ ~C ₆₀ alkylene group; C ₆ ~C ₆₀ arylene group; C ₂ ~ C ₆₀ is selected from any one of the heterocyclic group,
3) When R ₇ to R ₉ are an alkyl group, an alkenyl group, an alkoxy group, a hydroxy group, an alkylene group, an arylene group, a fluorenylene group, or a heterocyclic group, each of these is halogen; Hydrogen; heavy hydrogen; C ₆ ~ C ₂₀ aryl group substituted or unsubstituted silane group; Siloxane groups; Cyano group; Nitro group; C ₁ ~ C ₃₀ alkylthio group; C ₁ ~C ₃₀ Alkoxy group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkynyl group; C ₆ ~ C ₃₀ Aryl group; C ₆ ~ C ₃₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₃₀ heterocyclic group; C ₃ ~ C ₃₀ cycloalkyl group; C ₇ ~ C ₃₀ arylalkyl group and C ₈ ~ C ₃₀ may be further substituted with one or more substituents selected from the group consisting of aryl alkenyl groups, and these substituents may also combine with each other to form a ring.
According to claim 1,
Composition for sealing an organic light emitting device further comprising a compound (C) represented by the following formula (7):

In Chemical Formula 7,
1) L ₂ is a single bond; C ₁ ~ C ₆₀ alkyl group; C ₁ ~ C ₆₀ Alkylene group; C ₂ ~ C ₆₀ alkenyl group; C ₁ ~ C ₆₀ Alkoxy group; C ₆ ~ C ₆₀ Arylene group; C ₆ ~ C ₆₀ is selected from any one of the aryloxy group,
2) R ₁₀ is hydrogen; heavy hydrogen; Tritium; C ₁ ~ C ₆₀ alkyl group; C ₃ ~C ₃₀ cycloalkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₁ ~ C ₆₀ Alkoxy group; It is selected from any one of hydroxy groups,
3) R ₁₁ is an aryl group of C ₆ ~C ₆₀ ; C ₆ ~ C ₆₀ Allyloxy group; Fluorenyl group; C ₂ ~ C ₆₀ is selected from any one of the hetegorogi,
4) L ₂ , R ₁₀ and R ₁₁ are alkylene groups, alkyl groups, alkenyl groups, alkoxy groups, arylene groups, aryloxy groups, cycloalkyl groups, hydroxy groups, aryl groups, fluorenyl groups, and heterocyclic groups. Each halogen; heavy hydrogen; C ₆ ~ C ₂₀ aryl group substituted or unsubstituted silane group; Siloxane groups; Cyano group; Nitro group; C ₁ ~ C ₃₀ alkylthio group; C ₁ ~ C ₃₀ Alkoxy group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkynyl group; C ₆ ~ C ₃₀ Aryl group; C ₆ ~ C ₃₀ aryl group substituted with deuterium; Fluorenyl group; C ₂ ~ C ₃₀ heterocyclic group; C ₃ ~ C ₃₀ cycloalkyl group; C ₇ ~ C ₃₀ arylalkyl group and C ₈ ~ C ₃₀ may be further substituted with one or more substituents selected from the group consisting of aryl alkenyl group, and these substituents may be bonded to each other to form a ring.
According to claim 1,
The compound represented by Formula 1 is a composition for encapsulating an organic light emitting device having at least one of the following compounds:

.
Based on solids,
1 to 10% by weight of one or more compounds represented by Formula 1 of claim 1;
20% to 70% by weight of at least one compound represented by Formula 6 of claim 5; And
A composition for sealing an organic light emitting device comprising 5% to 40% by weight of at least one compound represented by Chemical Formula 7 of claim 6.
A device member; And
It is disposed on the member for the device and comprises a multi-layer barrier layer consisting of an inorganic barrier layer and an organic barrier layer;
The organic barrier layer is encapsulated device comprising the compound (A) of claim 1.

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