KR102669647B1 - Composition and compound for encapsulating organic light emitting diode and oencapsulated apparatus comprising the same - Google Patents

Abstract

The present invention provides a composition for encapsulating organic light-emitting devices that can improve the reliability of device members by preventing moisture and oxygen from penetrating from the outside, and an encapsulated device containing the same.

Description

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

The present invention relates to an encapsulation composition for organic light emitting devices and an encapsulated device containing the same.

In an organic light emitting diode (OLED), electrons injected from the cathode and holes injected from the anode combine in the light emitting layer of the organic light emitting unit to form an electron-hole pair. , is a flat panel display device that emits light during the process of recombination. Organic light emitting devices exhibit high luminous efficiency in the three primary colors of light, red, green, blue, and white, and have the advantages of low driving voltage and power consumption, wide viewing angle, and fast pixel response speed to display high-definition video. Have.

In addition, organic light-emitting devices are being actively researched in the field of flexible displays, as they enable the creation of ultra-thin and ultra-light displays that can be manufactured with a thickness of 1 mm or less on substrates such as glass or plastic. However, in organic light-emitting devices, the light-emitting and electrode materials are oxidized by oxygen or moisture, which causes problems such as dark spots and pixel shrinkage, ultimately reducing lifespan and efficiency. In addition, it has been reported that the lifespan and efficiency of OLED devices are reduced due to external light, including sunlight. Sunlight has a light intensity ratio of 2.5% ultraviolet rays, 51.5% visible rays, and 40.6% ultraviolet rays. Among these, ultraviolet rays have a small amount of light, but are energetically high, causing decomposition and deterioration of organic light-emitting materials, breaking down the molecular bonds of low-molecular and high-molecular materials. This is destroyed. At this time, there is no general route through which organic and organic-metal materials are decomposed by UV. Usually, organic and organic-metal materials of organic light-emitting devices 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 a binding site in an organic or organic-metal molecule where the binding energy is similar to or lower than the energy of the singlet excited state. Additionally, addition reactions may occur due to the radicals generated at this time to form neutral saturated decomposition products, which may act as impurities.

As a result, when the organic light-emitting device is exposed to external light (sunlight) for a long time, the organic material or organic-metal material of the organic light-emitting device is subjected to continuous stress due to the ultraviolet rays flowing into the device, causing the molecular bonds of the material to be destroyed. , the combination of broken molecules causes a change in the color coordinate of the organic light-emitting device, an increase in driving voltage, and a decrease in lifespan, so it is necessary to prevent ultraviolet rays from entering the organic light-emitting device.

As mentioned above, the development of encapsulation technology that blocks oxygen, moisture, and ultraviolet rays from entering the organic light emitting device is one of the essential key technologies.

This encapsulation technology can be broadly divided into three methods: Can (Glass encap), TFE (thin film encap), and Hybrid. Each method uses a Can with a cover plate made of metal or glass with gas barrier properties and a moisture absorbent (getter). The TEF method, which can be called a face sealing method that implements barrier properties with an organic or inorganic multilayer thin film on the upper layer of the device and a plastic barrier film as a cover plate, is used between the passivation thin film and the passivation thin film. It can be explained as a 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 is widely used to date, is a technology that places an organic light-emitting element between two glasses consisting of a substrate and a cover, and seals it by melting the glass powder with a laser or using UV adhesive, and has the best encapsulation characteristics. However, it has poor heat conduction characteristics due to the inert gas in the device, has the disadvantage of increasing costs due to glass processing due to larger areas, and is difficult to apply to the production of flexible OLED panels that require flexibility.

In order to make up for the shortcomings of this glass encapsulation technology, the front of the organic light emitting device is alternately laminated with thin films of inorganic layers such as Al ₂ O ₃ that have high barrier properties to oxygen or moisture and organic layers of polymer. TFE (Thin film encapsulation), a protective multi-layer thin film encapsulation technology, is being actively researched.

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

In U.S. Patent No. 7767498, it is stated that the more pairs of organic and inorganic barrier layers in a thin film, the more advantageous it is for the barrier properties of moisture and oxygen. However, through several film formation processes under vacuum conditions, the barrier properties may change due to the incorporation of foreign substances. A decrease in yield along with degradation is reported as a disadvantage.

In recent research, research is being conducted to increase the thickness of the organic/inorganic barrier layer and reduce the number of layers in a thin-film multilayer structure in order to overcome yield reduction while maintaining barrier properties. This is because reducing the number reduces the number of processes, thereby overcoming the decline in characteristics and yield due to contamination of foreign substances, thereby reducing manufacturing costs.

Therefore, the present invention provides an encapsulant composition capable of protecting organic light-emitting devices from ultraviolet rays while being flexible during film formation in accordance with the development direction of displays that are changing from rigid displays to flexible OLEDs.

The purpose of the present invention is to provide an encapsulating composition that has UV blocking ability and is suitable for an inkjet process.

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

Another object of the present invention is to provide a composition for encapsulation that can form a barrier layer for encapsulation of environmentally sensitive device members.

The composition for encapsulating organic light-emitting devices according to embodiments of the present invention may include compound (A) represented by the following Chemical Formula 1.

In another aspect, the present invention includes a device member and a multilayer barrier layer disposed on the device member and consisting of an inorganic barrier layer and an organic barrier layer, wherein the organic barrier layer contains the compound (A) of Formula 1 above. Provided is an encapsulated device comprising:

The encapsulating composition according to the present invention can improve the reliability of OLED devices by blocking moisture and oxygen from penetrating from the outside after curing. Additionally, 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 diagram of an organic light emitting device according to an embodiment of the present invention.
Figure 2 is a diagram schematically showing the structure of an electronic device including an organic light emitting device.
Figures 3 and 4 show transmittance data measured in examples and comparative examples.

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

In adding reference numerals to components in each drawing, it should be noted that the same reference numerals are assigned to the same components as much as possible even if they are shown in different drawings. Additionally, in describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

Additionally, when describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, sequence, 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 or connected to that other component, but there is another component between each component. It will be understood that elements may be “connected,” “combined,” or “connected.”

Additionally, when a component, such as a layer, membrane, region, plate, etc., is said to be "on" or "on" another component, it means not only that it is "directly above" the other component, but also that there is another component in between. It should be understood that it can also include cases. Conversely, when an element is said to be "right on top" of another part, it should be understood to mean that there is no other part in between.

The terms used in this specification and in the appended claims are as follows, unless otherwise noted.

As used herein, the term “halo” or “halogen” includes fluorine (F), chlorine (Cl), bromine (Br), and iodine (I), unless otherwise specified.

As used herein, unless otherwise specified, the term "alkyl" or "alkyl group" has 1 to 60 carbons connected by a single bond, and includes a straight-chain alkyl group, branched-chain alkyl group, cycloalkyl (cycloaliphatic) group, and alkyl-substituted group. It refers to radicals of saturated aliphatic functional groups, including cycloalkyl groups and cycloalkyl-substituted alkyl groups.

As used herein, the term “haloalkyl group” or “halogenalkyl group” refers to an alkyl group in which halogen is substituted, unless otherwise specified.

As used herein, the term "alkenyl" or "alkynyl", unless otherwise specified, has a double bond or triple bond, includes a straight or branched chain group, and has a carbon number of 2 to 60, but includes It is not limited.

The term “cycloalkyl” used herein, unless otherwise specified, refers to alkyl forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

The term “alkoxy group” or “alkyloxy group” used in this specification refers to an alkyl group to which an oxygen radical is bonded and, unless otherwise specified, has 1 to 60 carbon atoms, but is not limited thereto.

As used herein, the term “alkenoxyl group”, “alkenoxy group”, “alkenyloxyl group”, or “alkenyloxy group” refers to an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, refers to an alkenyl group having an oxygen radical attached thereto. It has a carbon number of, but is not limited to.

As used herein, the terms “aryl group” and “arylene group” each have 6 to 60 carbon atoms unless otherwise specified, but are not limited thereto. In the present specification, an aryl group or arylene group includes a single ring, a ring aggregate, a fused ring system, a compound, etc. 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 term "fluorenyl group" or "fluorenylene group" refers to a monovalent or divalent functional group of fluorene, respectively, unless otherwise specified, and "substituted fluorenyl group" or "substituted fluorenyl group" "Orenylene group" refers to a monovalent or divalent functional group of substituted fluorene, and "substituted fluorene" refers to a group in which at least one of the following substituents R, R', R", and R''' is a functional group other than hydrogen. This means that R and R' are combined with each other to form a spiro compound with the carbon to which they are connected.

In addition, R, R', R" and R''' are each independently selected from 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, and the heterocyclic group may be pyrrole, furan, thiophene, pyrazole, or imidazole. , triazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, indole, benzofuran, quinazoline, or quinoxaline. For example, the substituted fluorenyl group and fluorenylene group are 9,9, respectively. -It may be a monovalent or divalent functional group of dimethylfluorene, 9,9-diphenylfluorene, and 9,9'-spirobi[9H-fluorene].

As used herein, the term “ring assemblies” refers to two or more ring systems (single rings or fused ring systems) directly connected to each other through single or double bonds, and the direct connection between such rings. This means that the number of connections is one less than the total number of ring systems in this compound. In ring aggregates, the same or different ring systems may be directly connected to each other through single or double bonds.

In the present specification, since the aryl group includes a ring assembly, the aryl group includes biphenyl and terphenyl in which a benzene ring, which is a single aromatic ring, is linked by a single bond. In addition, the aryl group also includes compounds in which an aromatic ring system bonded to an aromatic single ring is connected by a single bond, so for example, fluorene, an aromatic ring system bonded to a benzene ring, which is an aromatic single ring, forms a conjugated pi electronic system ( It also includes compounds linked to form a conjugated pi electron system.

As used herein, the term "fused multiple ring system" refers to a fused ring form sharing at least two atoms, and includes a fused ring system of two or more hydrocarbons and at least one heteroatom. This includes forms in which at least one heterocyclic ring is fused. This fused multiple ring system may be an aromatic ring, a heteroaromatic ring, an aliphatic ring, or a combination of these rings.

The term "spiro compound" used herein has a 'spiro union', and the spiro union refers to a connection made by two rings sharing only one atom. At this time, the atom shared between the two rings is called a 'spiro atom', and depending on the number of spiro atoms in one compound, they are 'monospiro-', 'dispiro-', and 'trispiro-' respectively. 'It is called a compound.

The term "heterocyclic group" used herein includes aromatic rings such as "heteroaryl group" or "heteroarylene group" as well as non-aromatic rings, and unless otherwise specified, each carbon number containing one or more heteroatoms. It refers to a ring numbered from 2 to 60, but is not limited thereto. As used herein, the term "heteroatom" refers to N, O, S, P, or Si, unless otherwise specified, and the heterocyclic group refers to a single ring containing heteroatoms, a ring aggregate, a fused multiple ring system, or a ring group. refers to compounds, etc.

Additionally, the “heterocyclic group” may also include a ring containing SO ₂ instead of carbon forming the ring. For example, “heterocyclic group” includes the following compounds:

As used herein, the term “ring” includes single and polycyclic rings, includes hydrocarbon rings as well as heterocycles containing at least one heteroatom, and includes aromatic and non-aromatic rings.

The term "polycyclic" used herein includes ring assemblies such as biphenyl, terphenyl, etc., fused multiple ring systems, and spiro compounds, and includes aromatics as well as non-aromatics, and hydrocarbons. Rings of course include heterocycles containing at least one heteroatom.

Additionally, when prefixes are named consecutively, it means that the substituents are listed in the order they are listed first. For example, an arylalkoxy group refers to an alkoxy group substituted with an aryl group, an alkoxycarbonyl group refers to a carbonyl group substituted with an alkoxy group, and an arylcarbonylalkenyl group refers to an alkenyl group substituted with an arylcarbonyl group. Arylcarbonyl group is a carbonyl group substituted with an aryl group.

Also, unless explicitly stated otherwise, in the term "substituted or unsubstituted" used herein, "substituted" means 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 group, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, C ₆ -C ₂₀ aryl group substituted with deuterium, C ₈ -C ₂₀ arylalkenyl group, silane group, boron means substituted with one or more substituents selected from the group consisting of a group, a germanium group, and a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P. and is not limited to these substituents.

In this specification, the 'functional group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., as examples of each symbol and its substituent, may be written as the 'name of the functional group reflecting the valence', but is written as the 'parent compound name'. You may. For example, in the case of 'phenanthrene', a type of aryl group, the monovalent 'group' is 'phenanthryl (group)', the divalent group is 'phenanthrylene (group)', etc., and the name of the group is written by dividing the valence. However, it can also be written as 'phenanthrene', which is the name of the parent compound, regardless of the valence. Similarly, in the case of pyrimidine, it is written as 'pyrimidine' regardless of the valence, or the 'group' of the corresponding valence, such as pyrimidinyl (group) in the case of monovalent, pyrimidinylene (group) in the case of divalent, etc. It can also be written as ‘name’. Therefore, in this specification, when the type of substituent is described as the name of the parent compound, it may mean an n-valent 'group' formed by detachment of a hydrogen atom bonded to a carbon atom and/or a heteroatom of the parent compound.

Additionally, unless explicitly stated otherwise, the chemical formulas used in this specification are applied identically to the substituent definitions according to the exponent definitions in the following chemical formulas.

Here, when a is 0, the substituent R ¹ is absent, when a is 1, one substituent R ¹ is bonded to any one of the carbons forming the benzene ring, and when a is 2 or 3, each is as follows They are bonded together, and in this case, R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, and the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted. .

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

1 is an exemplary diagram 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 a substrate 110. ) and an organic material layer containing the compound according to the present invention is provided between them. At this time, the first electrode 120 may be an anode and the second electrode 180 may be a cathode. In the case of the inverted type, the first electrode may be the cathode and the second electrode may be the 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, an emission auxiliary layer 151, a buffer layer 141, etc. may be further included, and an electron transport layer 160, etc. may serve as a hole blocking layer. You might be able to 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 improvement layer (capping layer) formed on at least one side of the first electrode and the second electrode opposite to the organic material layer.

The compound according to the present invention applied to the organic 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 improvement layer, a light emitting auxiliary layer, etc. It can be used as a material for For example, the compound of the present invention can be used as a material for the auxiliary light emitting layer 151 and/or the light emitting layer 150.

Meanwhile, even if it is the same core, the band gap, electrical properties, and interface properties may vary depending on which substituent is attached to which position, so the selection of the core and the combination of subsubstituents attached to it are very important, especially When the energy level and T ₁ value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined, long lifespan and high efficiency can be achieved at the same time.

As already explained, in order to solve the problem of light emission from the hole transport layer in recent organic electroluminescent devices, it is desirable to form a light emitting auxiliary layer between the hole transport layer and the light emitting layer, corresponding to each light emitting layer (R, G, and 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 auxiliary layer among the red light emitting layer, green light emitting layer, and blue light emitting layer corresponding to the red light emitting layer, green light emitting layer, and blue light emitting auxiliary layer. Meanwhile, in the case of the auxiliary light emitting layer, the interrelationship between the hole transport layer and the light emitting layer (host) must be identified, so even if a similar core is used, it will be very difficult to infer its characteristics if the organic material layer used is different.

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 and T ₁ value between each organic material layer and the intrinsic properties of the material (mobility, interface properties, etc.) By optimizing the etc., the lifespan and efficiency of organic electric devices can be improved at the same time.

An organic light emitting device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD (Physical Vapor Deposition) or CVD (Chemical Vapor Deposition). For example, the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate. After forming 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, a cathode 180 is formed thereon. It can be manufactured by depositing any available material. Additionally, 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 uses various polymer materials to process a solution process or a solvent process, such as spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading process, It can be manufactured with fewer layers by methods such as a screen printing process or thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, 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-emitting type, a rear-emitting type, or a double-sided emitting type depending on the material used.

WOLED (White Organic Light Emitting Device) has the advantage of being easy to achieve high resolution and having excellent fairness, while being manufactured using the color filter technology of existing LCDs. Various structures for white organic light emitting devices, mainly used as backlight devices, are being proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are arranged in parallel in a mutual plane, and a stacking method in which R, G, and B light emitting layers are stacked top and bottom. There is a color conversion material (CCM) method that uses electroluminescence by a blue (B) organic light-emitting layer and photo-luminescence of an inorganic phosphor using light therefrom, and the present invention. can be applied to these WOLEDs as well.

Additionally, 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), and a device for monochromatic or white lighting.

Additionally, the present invention may further include an encapsulation layer 300 to protect the organic light emitting device 200. Although FIG. 1 shows a configuration in which the encapsulation layer 300 is a single layer, the present invention is not limited to this, and the encapsulation layer 300 may be composed of multiple layers. This configuration is reviewed with reference to FIG. 2 as follows.

Figure 2 is a diagram schematically showing an example of the 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 disposed on the organic light emitting device 200. In an electronic device according to one example, the organic light emitting device 200 can be protected using the encapsulation layer 300.

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

Additionally, 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 can be arranged in a structure that can effectively protect the organic light emitting device 200. At this time, the encapsulation layer 300 has the effect of improving the reliability of the electronic device by blocking moisture and oxygen in the organic light emitting device 200. The encapsulation composition constituting the encapsulation layer 300 can exhibit the above-described effects by including compound (A) represented by the following formula (1).

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

Hereinafter, Formula 1 will be described.

Ring A and Ring B are each independently the same or different and include an aryl group of C ₆ to C ₃₀ ; A fused ring group of an aromatic ring from C ₆ to C ₃₀ and an aliphatic ring from C ₃ to C ₃₀ ; Any one of C ₂ to C ₃₅ heterogeneous groups may be selected.

R ₁ and R ₂ are each independently the same or different and are deuterium; tritium; hydroxyl group; halogen group; Cyano group; Aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₁ ~ C ₆₀ alkyl group; A fused ring group of an aromatic ring from C ₆ to C ₆₀ and an aliphatic ring from 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; 2 siloxane group; C ₇ ~ C ₆₀ arylalkoxyl group; C ₈ ~ C ₆₀ arylalkenyl group; and a C ₂ to C ₆₀ alkoxylcarbonyl group.

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

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

R ₃ to R ₆ are each independently the same or different and are deuterium; tritium; hydroxyl group; halogen group; Cyano group; Aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₁ ~ C ₆₀ alkyl group; A fused ring group of an aromatic ring from C ₆ to C ₆₀ and an aliphatic ring from 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; 2 siloxane group; C ₇ ~ C ₆₀ arylalkoxyl group; C ₈ ~ C ₆₀ arylalkenyl group; and a substituent selected from any one of C ₂ to C ₆₀ alkoxylcarbonyl groups, and R ₃ to R ₆ may be combined with each other to form a ring.

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

L ₁ is a single bond; C ₆ ~ C ₆₀ arylene group; and C ₂ to C ₆₀ heterocyclic group.

Y ₁ is O (oxygen); S(Hwang); C ₁ -C ₂₀ alkylene group; C ₆ ~ C ₂₄ heteroarylene group; C ₇ ~ C ₂₄ arylalkylene group; C ₂ ~ C ₂₀ alkenylene group; Any one of C ₆ to C ₂₄ arylene groups may be selected.

L ₁ ' is a single bond; Arylene group of C ₆ to C ₂₄ ; C ₁ ~ C ₃₀ alkylene group; and an aryloxy group of C ₆ to C ₂₄ .

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

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; Any one of the hydroxy groups may be selected.

n1 and n2 may each be integers from 0 to 2.

The A ring, B ring, R ₁ to R ₆ , _R ' and R'', Ar ₁ , L ₁ , Y ₁ , _{L 1 '} , Ring group, akyl group, akenyl group, alkynyl group, alkoxy group, allyloxy group, allylalkyl group, alkenolyl group, alkenyl aryl group, cycloalkyl group, arylalkoxyl group, arylalkenyl group, alkoxylcarbonyl group, arylene group, In the case of an alkylene group, heteroarylene group, arylalkylene group or alkenylene group, each of them is halogen; heavy hydrogen; C ₆ ~ C ₂₀ Silane group substituted or unsubstituted with an aryl group; siloxane group; Cyano group; nitro group; C ₁ ~ C ₃₀ alkylthio group; C ₁ ~ C ₃₀ alkoxyl group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkyne 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; It may be further substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₃₀ arylalkyl group and C ₈ ~ C ₃₀ arylalkenyl group, and these substituents can be combined with each other to form a ring.

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

Here, in the case of the aryl group, the aryl group may have 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, and in the case of the heterocyclic group, the aryl group may have 2 to 60 carbon atoms, preferably 2 to 2 carbon atoms. 30, more preferably a heterocyclic group with 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, especially preferably 1 to 2 carbon atoms. It may be an alkyl group of 10.

In the case of the above-mentioned allyl group or allylene group, specifically, the allyl group or allylene group is independently a phenyl group, a biphenylene group, a terphenyl group, a naphthyl group, a phenanthryl group, or a phenylene group, a biphenylene group, a terphenylene group, or a naphthyl group. It may be a thylene group, phenanthrylene group, pyrene, or triphenylene.

The compound of Formula 1 can function as a UV blocker (A) in an encapsulation material for organic electric devices. The encapsulation composition containing the compound of Formula 1 can form an encapsulation layer with excellent UV blocking performance.

The composition for encapsulating organic light-emitting devices according to the present invention may include two or more types of compounds represented by Chemical Formula 1. For example, the composition for encapsulating an organic light emitting device according to the present invention includes a compound (A) represented by Formula 1, and may further include one or more compounds represented by Formula 1 and different from the compound (A). You can.

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

In 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 those defined in the description of Formula 1 above.

The compound represented by Formula 1 may be represented by one of the following 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 those defined in the description of Formula 1.

When using a compound represented by any one of the above formulas (a-1 to a-15), an encapsulation layer with excellent UV blocking performance can be provided.

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

The composition for encapsulating organic light-emitting devices according to the present invention may include one or more compounds represented by Formula 1, and based on the total solid content 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 Formula 1 in the above content range, the encapsulating composition of the present invention can provide an encapsulating layer with excellent UV blocking performance.

The composition for encapsulating organic light-emitting devices according to the present invention may further include compound (B) represented by the following formula (6).

Hereinafter, Chemical 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; Any one of the hydroxy groups may be selected.

R ₉ is an alkylene group of C ₁ to C ₆₀ ; C ₆ ~ C ₆₀ arylene group; Any one of the heterocyclic groups C ₂ to C ₆₀ may be selected.

When R ₇ to R ₉ are an alkyl group, an akenyl group, an alkoxy group, a hydroxy group, an alkylene group, an arylene group, a fluorenylene group, or a heterocyclic group, each of them is halogen; hydrogen; heavy hydrogen; C ₆ ~ C ₂₀ Silane group substituted or unsubstituted with an aryl group; siloxane group; Cyano group; nitro group; C ₁ ~ C ₃₀ alkylthio group; C ₁ ~ C ₃₀ alkoxyl group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkyne 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; It may be further substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₃₀ arylalkyl group and C ₈ ~ C ₃₀ arylalkenyl group, and these substituents may be combined with each other to form a ring.

Here, in the case of the aryl group, the aryl group may have 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, and in the case of the heterocyclic group, the aryl group may have 2 to 60 carbon atoms, preferably 2 to 2 carbon atoms. 30, more preferably a heterocyclic group with 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, especially preferably 1 to 2 carbon atoms. It may be an alkyl group of 10.

In the case of the above-mentioned allyl group or allylene group, specifically, the allyl group or allylene group is independently a phenyl group, a biphenylene group, a terphenyl group, a naphthyl group, a phenanthryl group, or a phenylene group, a biphenylene group, a terphenylene group, or a naphthyl group. It may be a thylene group, phenanthrylene group, pyrene, or triphenylene.

The composition for encapsulating organic light-emitting devices of the present invention includes di(meth)acrylate (B) represented by Chemical Formula 6, so that the photocuring rate can be further increased and deposition can be easier due to low viscosity. 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, or a substituted Or it may be an unsubstituted C ₂ to C ₆₀ heterocyclic group, preferably a substituted or unsubstituted group.

It is a C ₁ to C ₆₀ alkylene group, a substituted or unsubstituted C ₆ to C ₆₀ arylene group, and more preferably a substituted or unsubstituted C ₁ to C ₃₀ alkylene group.

The compound represented by Formula 6, preferably di(meth)acrylate, is octanediol di(meth)acrylate; nonanedioldi(meth)acrylate; Decanediol 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; It may include, but is not limited to, one or more of arachidyldi(meth)acrylate.

The composition for encapsulating organic light-emitting devices according to the present invention may include one or more compounds represented by Formula 6, and the total weight of the compounds represented by Formula 6 is 20 weight based on the total solid content 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 Formula 6 in the above content range, the encapsulating composition of the present invention can provide an encapsulating layer with excellent ultraviolet ray blocking performance.

The composition for encapsulating organic light-emitting devices according to the present invention may further include a mono(meth)acrylate compound (C) represented by the following formula (7).

Hereinafter, Chemical 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; Any one of C ₆ to C ₆₀ aryloxy groups may be selected.

R ₁₀ is hydrogen; heavy hydrogen; tritium; C ₁ ~ C ₆₀ alkyl group; C ₃ to C ₃₀ cycloalkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₁ ~ C ₆₀ alkoxy group; Any one of the hydroxy groups may be selected.

R ₁₁ is an aryl group of C ₆ to C ₆₀ ; C ₆ ~ C ₆₀ allyloxy group; fluorenyl group; Any one of C ₂ to C ₆₀ heterogeneous groups may be selected.

Wherein L ₂ , R ₁₀ and R ₁₁ are an 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, or a heterocycle, each of them is halogen; heavy hydrogen; C ₆ ~ C ₂₀ Silane group substituted or unsubstituted with an aryl group; siloxane group; 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 alkyne 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; It may be further substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₃₀ arylalkyl group and C ₈ ~ C ₃₀ arylalkenyl group, and these substituents may be combined with each other to form a ring.

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

Here, in the case of the aryl group, the aryl group may have 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, and more preferably 6 to 30 carbon atoms, and in the case of the heterocyclic group, the aryl group may have 2 to 60 carbon atoms, preferably 2 carbon atoms. It may be a heterocycle having ~30 carbon atoms, more preferably 2-20 carbon atoms, and in the case of the alkyl group, the carbon number is 1-50, preferably 1-30 carbon atoms, more preferably 1-20 carbon atoms, especially preferably. It may be an alkyl group of 1 to 10. In the case of the above-mentioned aryl group or arylene group, specifically, the aryl group or arylene group is independently 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, or a naphthyl group. It may be a rene group, phenanthrylene group, pyrene, or triphenylene.

For example, R ₁₁ is phenylphenoxyethyl group, phenoxyethyl group, benzyl group, phenyl group, phenylphenoxy group, phenoxy group, phenylethyl group, phenylpropyl group, phenylbutyl group, methylphenylethyl group, propylphenylethyl group, and 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 (terphenyl) ) group, quaterphenyl group, anthracenyl group, naphthalenyl group, triphenylenyl group, methylphenoxy group, ethylphenoxy group, methylethylphenoxy group, methoxyphenyloxy group, propylphenoxy group, cyclohexyl Phenoxy group, chlorophenoxy group, bromophenoxy group, biphenyloxy group, terphenyloxy group, quaterphenyloxy group, anthracenyloxy group, naphthalenyloxy group, triphenyloxy group It can be a phenylenyloxy (triphenylenyloxy) group.

For example, 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

related; 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; It may include, but is not limited to, 1-(4-benzylphenyl)ethyl(meth)acrylate or one or more of its structural isomers. In addition, the (meth)acrylate mentioned in the present invention is only an example and is not limited thereto, and furthermore, the present invention includes all acrylates that are structural isomers. For example, even if only 2-phenylethyl (meth)acrylate is mentioned as an example of the present invention, the present invention includes one or more of 3-phenylethyl (meth)acrylate and 4-phenyl (meth)acrylate. It can be done, but is not limited to this.

The composition for encapsulating organic light-emitting devices according to the present invention may include one or more compounds represented by Formula 7, and based on the total solid content contained in the composition, the total weight of the compounds represented by 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 Formula 7 in the above content range, the encapsulating composition of the present invention can provide an encapsulating layer with excellent UV blocking performance.

The encapsulating composition containing Formula 1 of the present invention can form an organic barrier layer located between inorganic barrier layers for use in encapsulating or encapsulating flexible display devices, and the organic barrier layer is formed by photocuring the encapsulating composition. can be formed.

The encapsulating composition (organic barrier layer material) can be applied using methods such as vapor deposition, spin coating, or slit coating, and an initiator (D) can be used during photocuring.

The initiator may include, without limitation, a conventional photopolymerization initiator capable of performing a photocuring 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.

Triazine series include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloro methyl)-s-triazine, and 2-(3',4'-dimethoxy thiazine. Lil)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxy naphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-( p-methoxy phenyl)-4,6-bis(trichloro methyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloro methyl)-s-triazine, 2-b Phenyl-4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphtho-1-yl)-4,6- Bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl (piperonyl)-6-triazine, 2,4-(trichloromethyl(4'-methoxy styryl)-6-triazine, or mixtures thereof.

Acetophenone series include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methyl propiophenone, p-t-butyl trichloroacetophenone, and p-t-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.

Benzophenone series include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis(dimethyl amino)benzophenone, and 4,4'-dichlorobenzo. It may be phenone, 3,3'-dimethyl-2-methoxy benzophenone, or mixtures thereof.

Thioxanthone series include thioxanthone, 2-methyl thioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2-chloro thioxanthone, or It can be a mixture of these.

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

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

Oxime systems 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 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 of the composition based on solid content. Within the above range, photopolymerization can sufficiently occur upon exposure, and transmittance can be prevented from being reduced due to unreacted initiator remaining after photopolymerization.

In addition, the composition for encapsulating organic light-emitting devices according to the present invention may further include a light stabilizer.

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

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

For example, cyanoacrylates include ethyl 2-cyano-3.3-diphenyl acrylate, 2-ethylhexyl 2-cyano-3,3-diphenyl acrylate, and hexyl 2-cyano-3,3- It may be diphenylacrylate, octyl 2-cyano-3-(4-methoxyphenyl)-3-phenylacrylate, or mixtures thereof.

For example, hindered amine systems include tetrakis[methylene 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]methane, thiodiethylene bis[3(3,5-di- tert-butyl-4-hydroxyphenyl)propionate], octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, isotridecyl-3-(3, 5-di-tert-butyl-4-hydroxyphenyl)propionate, hexamethyl (3,5-di-tert-butyl-4-hydroxydrosinamide), iso-octyl-3-(3,5 -di-tert-butyl-4-hydroxyphenyl)propionate or a mixture 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-hyde) Roxybenzyl) phosphonate] or a mixture thereof.

The light stabilizer may be included in the composition in an amount of 0.1 to 10% by weight, preferably 0.1 to 5% by weight, and more preferably 0.1 to 3% by weight. When the composition for encapsulating organic light-emitting devices is exposed to ultraviolet rays in the above range for a long period of time, the function of the ultraviolet absorber can be maintained for a long time.

To form an organic barrier layer using photocuring, the encapsulating composition is coated to a thickness of 0.1 to 20 ㎛, preferably 1 to 15 ㎛, most preferably 1 to 10 ㎛, and irradiated at 10 to 500 mW/㎠ for 1 to 60 seconds. It can be hardened. At this time, the curing rate may be 90% or more, and preferably 93% or more. At this time, compositions and initiators that do not participate in the photocuring reaction within the organic barrier layer are minimized, and the pass-way of moisture and/or oxygen is suppressed, resulting in good barrier properties.

In addition, when curing the encapsulating composition (when forming an organic barrier layer), the coated encapsulating composition may shrink, and the shrinkage rate is about 1 to 20%, more preferably 1 to 15%. It can be.

When the shrinkage rate of the organic barrier layer is more than 20%, oxygen and/or moisture penetrate into the inorganic barrier layer.

Dark spots and pixel shrinkage occur, and two or more layers are formed.

When forming an organic-inorganic multilayer barrier layer, bending may occur, which may lead to the combination of light-emitting devices.

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

The multilayer barrier layer includes the organic barrier layer and the inorganic barrier layer, but can be deposited alternately, and the number of barrier layers is not limited, and the number of barrier layers depends on the permeability 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 or more layers and ten or fewer layers, respectively, and are preferably in one or more layers and three or fewer layers.

Hereinafter, the synthesis example of the compound represented by Formula 1 and the manufacturing example of the organic electric device according to the present invention will be described in detail through examples, but the present invention is not limited to the following examples.

Compounds (final products) according to the present invention are synthesized according to the following reaction scheme, but 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 Scheme 1 may be synthesized through the reaction route of Scheme 2 below, but is not limited thereto.

<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, then Triethylamine (37.36 g, 255.48 mmol) was added and stirred at 80°C. When the reaction is complete, extraction is performed 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

<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, 66.78 mmol) and 2-hydroxyethyl acrylate (7.75 g, 66.78 mmol) were dissolved in Acetonitrile (330 ml) in a round bottom flask, and then Triethylamine (29.29 g, 200.34 mmol) was added to 21.02 g of product (29.29 g, 200.34 mmol) using the Sub1-2 synthesis method above. Yield 65%) was obtained.

3. Sub 1-10 synthesis example

<Scheme 5>

Starting with 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 -hydroxyethyl acrylate (6.65 g, 57.33 mmol) was dissolved in Acetonitrile (300 ml) in a round bottom flask, and then triethylamine (25.12 g, 171.99 mmol) was added to produce 24 g of product (75% yield) using the Sub1-2 synthesis method above. got it

4. Sub 1-20 Synthesis Example

<Scheme 6>

Starting 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 produce 18.72 g (18.72 g) of the product using the Sub1-2 synthesis method above. Yield 69%) was obtained.

5. Sub 1-26 Synthesis Example

<Scheme 7>

Starting 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 added to produce 23.52 g of product using the Sub1-2 synthesis method above. (73% yield) was obtained.

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 ( After dissolving 8.95 g, 77.09 mmol) in Acetonitrile (385 ml) in a round bottom flask, 26.49 g of product (yield 81%) was obtained using Triethylamine (33.82 g, 231.27 mmol) using the Sub1-2 synthesis method above.

7. Sub 1-31 Synthesis Example

<Scheme 9>

Starting 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 bottom flask, Triethylamine (29.96 g, 204.93 mmol) was added using the Sub1-2 synthesis method to produce 18.79 g of product (yield 58%). ) was obtained.

8. Sub 1-36 Synthesis Example

<Scheme 10>

Starting with 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 dissolving acrylate (7.71 g, 66.93 mmol) in Acetonitrile (330 ml) in a round bottom flask, Triethylamine (29.36 g, 200.79 mmol) was obtained using the Sub1-2 synthesis method above to obtain 21.35 g (yield 66%) of the product.

9. Sub 1-45 synthesis example

<Scheme 11>

Starting with 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) After dissolving 2-hydroxyethyl acrylate (7.28 g, 62.73 mmol) in Acetonitrile (300 ml) in a round bottom flask, Triethylamine (27.52 g, 188.19 mmol) was added using the Sub1-2 synthesis method to produce 28.66 g of product (89% yield). ) was obtained.

Meanwhile, the compounds belonging to Sub 1 may be the following compounds, but are not limited thereto, and Table 1 shows the FD-MS values of the compounds 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. P1-2 Synthesis Example

<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 -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 Toluene (140 ml) and H ₂ O (70 ml) in a bottom flask, K ₂ CO ₃ (11.58 g, 83.97 mmol) and Pd(PPh ₃ ) ₄ (1.61 g, 1.39 mmol) were added and stirred at 110 ^o C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was subjected to a silicagel column to obtain 12.27 g of product (yield: 75%).

2. P1-15 Synthesis Example

<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 used to obtain 10.17 g of product (yield: 62%) using the P-2 synthesis method.

3. P1-22 Synthesis Example

<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), and H ₂ O (70 ml) were used to obtain 17.45 g of product (yield: 88%) using the P-2 synthesis method.

4. P1-28 Synthesis Example

<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), and H ₂ O (70 ml) were used to obtain 11.48 g of product (yield: 58%) using the P-2 synthesis method.

5. P1-45 synthesis example

<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), and 13.45 g of product (yield: 92%) were obtained using the P-2 synthesis method.

6. P1-57 synthesis example

<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), and 11.26 g of product (yield: 75%) were obtained using the P-2 synthesis method.

7. P1-69 Synthesis Example

<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 (50ml), and 11.10 g of product (yield: 78%) were obtained using the P-2 synthesis method.

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), and 11.71 g of product (yield: 67%) were obtained using the P-2 synthesis method.

9. P1-82 Synthesis Example

<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 (70ml), and 13.82 g of product (yield: 78%) were obtained using the P-2 synthesis method.

10. P1-99 Synthesis Example

<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 (50ml), and 12.46 g of product (yield: 78%) were obtained using the P-2 synthesis method.

Meanwhile, the FD-MS values of compounds P-1 to P-100 of the present invention prepared according to the above synthesis examples 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 composition for encapsulating organic light emitting devices

[Example 1]

In Example 1, (A) 3.5 parts by weight of the compound P1-2 of the present invention (A1) as a sunscreen, (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) 0.9 parts by weight of CHISORB 336 (DBC) as a light stabilizer was placed in a 20ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare an encapsulating composition (viscosity 16.3cps at 25°C).

[Example 2]

In Example 1, (A) 5.3 parts by weight of compound P1-15 of the present invention (A2) as a sunscreen, (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) 0.9 parts by weight of CHISORB 336 (DBC) as a light stabilizer was placed in a 20ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare an encapsulating composition (viscosity 18.2cps at 25°C).

[Example 3]

In Example 1, (A) 5.8 parts by weight of the compound P1-22 of the present invention (A3) as a sunscreen, (B) di(meth)acrylate (B1) 1,10-decanediol diacrylate (TCI) 56.0 parts by weight, (C) 35.3 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) 0.9 parts by weight of CHISORB 336 (DBC) as a light stabilizer was placed in a 20ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare an encapsulation composition (viscosity 19.5cps at 25°C).

[Example 4]

In Example 1, (A) 4.2 parts by weight of the compound P1-28 of the present invention (A4) as a sunscreen, (B) di(meth)acrylate (B1) 1,10-decanediol diacrylate (TCI) 56.6 parts by weight, (C) 36.3 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) 0.9 parts by weight of CHISORB 336 (DBC) as a light stabilizer was placed in a 20ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare an encapsulation composition (viscosity 17.8cps at 25°C).

[Example 5]

In Example 1, (A) 3.8 parts by weight of the compound P1-45 of the present invention (A5) as a sunscreen, (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) 0.9 parts by weight of CHISORB 336 (DBC) as a light stabilizer was placed in a 20ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare an encapsulation composition (viscosity 17.2cps at 25°C).

[Example 6]

In Example 1, (A) 3.1 parts by weight of compound P1-57 of the present invention (A6) as a sunscreen, (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) 0.9 parts by weight of CHISORB 336 (DBC) as a light stabilizer was placed in a 20ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare an encapsulating composition (viscosity 16.5cps at 25°C).

[Comparative Example 1]

In Comparative Example 1, the (F) sunscreen was 8.8 parts by weight of (F1) TINUVIN 328 (Basf), and (B1) di(meth)acrylate was 52.9 parts by weight of (B1) 1,10-decanediol diacrylate (TCI). 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) 0.9 parts by weight of CHISORB 336 (DBC) as a light stabilizer was placed in a 20ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare an encapsulating composition (viscosity 21.6cps at 25°C).

[Comparative Example 2]

In Comparative Example 1, 8.8 parts by weight of (F2) ZIKO-460 (ZIKO) was used as a (F) sunscreen, and (B1) di(meth)acrylate was (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 ) 0.9 parts by weight of CHISORB 336 (DBC) as a light stabilizer was placed in a 20ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare an encapsulation composition (viscosity 26.9cps at 25°C).

[Comparative Example 3]

In Comparative Example 1, the (F) sunscreen was 8.8 parts by weight of (F3) Tinosorb M (Basf), and (B1) di(meth)acrylate was 52.9 parts by weight of (B1) 1,10-decanediol diacrylate (TCI). 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) 0.9 parts by weight of CHISORB 336 (DBC) as a light stabilizer was placed in a 20ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare an encapsulating composition (viscosity 28.2cps at 25°C).

[Comparative Example 4]

In Comparative Example 1, the (F) sunscreen was 8.8 parts by weight of (F3) CYASORB UV-24 (CYTEC), and (B1) di(meth)acrylate was (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 ( E) 0.9 parts by weight of CHISORB 336 (DBC) as a light stabilizer was placed in a 20ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare an encapsulating composition (viscosity 19.8cps at 25°C).

Film formation method

Under N ₂ conditions, 2 ml of the encapsulating compositions of Examples 1 to 6 and Comparative Examples 1 to 4 were added dropwise ^to a 50 mm was formed.

Physical property evaluation method

1. Transmittance

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

2. Light curing rate

For the photocurable composition, the intensity of absorption peaks around 1635 cm -1 (C=C) and 1720 cm ^-1 (C=O) were measured using FT-IR (FT/IR-6600, Jasco). Measure the intensity of absorption peaks around 1635cm-1 (C=C) and 1720cm ^-1 (C=O). The photocuring rate was calculated according to Equation 1 below.

<Equation 1>

Photocuring rate (%) = ｜1-(A/B)｜ x 100

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

The measurement results of the encapsulating compositions prepared in Examples and Comparative Examples are shown in Table 3 below, and the transmittance graphs are shown in Figures 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 69.4 405 nm 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 from the results in Table 3 above, in Examples 1 to 6, where a composition containing A1 to A6, which are materials of Chemical Formula 1 of the present invention, as a sunscreen, was used as an encapsulation material, the concentration was 0.3% to 0.3% at 400 nm to 405 nm. It was confirmed that it showed a transmittance of 5.3% and a transmittance of 90.3% to 97.2% at 430nm to 440nm. Additionally, the photocuring rate was 92.7% to 93.8%, and the viscosity was 16.5 cps to 19.3 cps. I was able to.

Comparing the results in Table 3 in more detail, only the type of sunscreen is different, and in the case of Example 1 and Comparative Examples 1 to 4 in which all compositions and usage amounts are the same, Example 1 using the present invention material P1-2 It was confirmed that the transmittance was 1.1% at 400 nm, and Comparative Examples 1 to 4 showed 69.4% to 91.4%. Additionally, when the transmittance was checked at 405 nm, it was confirmed that Example 1 was 4.0%, and Comparative Examples 1 to 4 were 81.5% to 95.4%. It was confirmed that when P1-2, the material of the present invention, was used as a sunscreen, the UV-blocking 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 an encapsulation material,

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

Additionally, as a result of comparing Examples 1 to 6 using the present invention material, the material with the lowest transmittance at 400 nm was the P1-28 material used in Example 4, and the material with the lowest transmittance at 405 nm was Example 5. This is the P-45 substance used in.

The above description is merely an illustrative description of the present invention, and those skilled in the art will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in this specification are for illustrative purposes rather than limiting 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 in accordance with the claims below, and all technologies within the equivalent scope should be interpreted as being included in the scope of rights of the present invention.

110: substrate
200: Organic light emitting device
300: Encapsulation layer
310: first bag layer
320: Second bag layer

Claims (9)

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

In Formula 1 above,
1) Ring A and Ring B are each independently the same or different and contain an aryl group of C ₆ to C ₃₀ ; A fused ring group of an aromatic ring from C ₆ to C ₃₀ and an aliphatic ring from C ₃ to C ₃₀ ; Any one of the heterogeneous groups from C ₂ to C ₃₅ is selected,
2) R ₁ and R ₂ are each independently the same or different and are deuterium; tritium; hydroxyl group; halogen group; Cyano group; Aryl group of C ₆ to C ₆₀ ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₁ ~ C ₆₀ alkyl group; A fused ring group of an aromatic ring from C ₆ to C ₆₀ and an aliphatic ring from 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; 2 siloxane group; C ₇ ~ C ₆₀ arylalkoxyl group; C ₈ ~ C ₆₀ arylalkenyl group; and a substituent selected from any one of C ₂ to C ₆₀ alkoxylcarbonyl groups,
3) R ₁ and R ₂ are plural when o and p are 2 or more, and are the same or different from each other, and a plurality of R ₁ and R ₂ Together 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 be combined with each other to form a ring,
6) X is O (oxygen), S (sulfur), NAr ₁ or CR'R",
R' and R" are an alkyl group of C ₁ ~ C ₃₀ ; an aryl group of C ₆ ~ C ₃₀ , R' and R" can combine with each other to form a spiro compound, and Ar ₁ is an alkyl group of C ₁ ~ C ₃₀ alkyl group; Aryl group of C ₆ to C ₆₀ ; Any one of the heterocyclic groups C ₂ to C ₆₀ is selected,
7) L ₁ is a single bond; C ₆ ~ C ₆₀ arylene group; and C ₂ to C ₆₀ heterocyclic group,
8) Y ₁ is O (oxygen); S(Hwang); C ₁ -C ₂₀ alkylene group; C ₆ ~ C ₂₄ heteroarylene group; C ₇ ~ C ₂₄ arylalkylene group; C ₂ ~ C ₂₀ alkenylene group; Any one of the arylene groups from C ₆ to C ₂₄ is selected,
9) L ₁ ' is a single bond; C ₆ ~ C ₂₄ arylene group; C ₁ ~ C ₃₀ alkylene group; And C ₆ ~ C _24, is selected from any one of the aryloxy groups,
10) X ₁ is O; S; NR'; C ₁ ~ C ₂₀ alkyl group; C ₆ ~ C ₂₄ aryl group; Any one of the alkenyl groups from C ₂ to C ₂₀ is selected,
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; One of the hydroxy groups is selected,
12) n1 is an integer of 0 or 1, n2 is an integer of 1,
13) The A ring, B ring, R ₁ to R ₆ , R' and R'', Ar ₁ , L ₁ , Y ₁ , _{L 1 ' ,} , fused ring group, akyl group, akenyl group, alkynyl group, alkoxy group, allyloxy group, allylalkyl group, alkenolyl group, alkenyl aryl group, cycloalkyl group, arylalkoxyl group, arylalkenyl group, alkoxylcarbonyl group, aryl In the case of a lene 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 Silane group substituted or unsubstituted with an aryl group; siloxane group; Cyano group; nitro group; C ₁ ~ C ₃₀ alkylthio group; C ₁ ~ C ₃₀ alkoxyl group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkyne 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; It may be further substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₃₀ arylalkyl group and C ₈ ~ C ₃₀ arylalkenyl group, and these substituents can be combined with each other to form a ring.
According to clause 1,
The compound represented by Formula 1 is a composition for encapsulating organic light-emitting devices represented by any one of the following Formulas 2 to 5:

. According to clause 1,
The compound represented by Formula 1 is a composition for encapsulating an organic light emitting device, characterized in that it is represented by one of the following Formulas (a-1) to (a-15):







.
According to clause 1,
A composition for encapsulating an organic light-emitting device, represented by Formula 1 and further comprising at least one compound different from compound (A).
According to clause 1,
A composition for encapsulating an organic light-emitting device further comprising compound (B) represented by the following formula (6):

In Formula 6 above,
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; One of the hydroxy groups is selected,
2) R ₉ is an alkylene group of C ₁ to C ₆₀ ; C ₆ ~ C ₆₀ arylene group; Any one of the heterocyclic groups from C ₂ to C ₆₀ is selected,
3) When R ₇ to R ₉ are an alkyl group, an akenyl group, an alkoxy group, a hydroxy group, an alkylene group, an arylene group, a fluorenylene group, or a heterocyclic group, each of them is halogen; hydrogen; heavy hydrogen; C ₆ ~ C ₂₀ Silane group substituted or unsubstituted with an aryl group; siloxane group; Cyano group; nitro group; C ₁ ~ C ₃₀ alkylthio group; C ₁ ~ C ₃₀ alkoxyl group; C ₁ ~ C ₃₀ alkyl group; C ₂ ~ C ₃₀ alkenyl group; C ₂ ~ C ₃₀ alkyne 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; It may be further substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₃₀ arylalkyl group and C ₈ ~ C ₃₀ arylalkenyl group, and these substituents may be combined with each other to form a ring.
According to clause 1,
A composition for encapsulating an organic light-emitting device further comprising a compound (C) represented by the following formula (7):

In Formula 7 above,
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; Any one of the aryloxy groups of C ₆ to C ₆₀ is selected,
2) R ₁₀ is hydrogen; heavy hydrogen; tritium; C ₁ ~ C ₆₀ alkyl group; C ₃ to C ₃₀ cycloalkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₁ ~ C ₆₀ alkoxy group; One of the hydroxy groups is selected,
3) R ₁₁ is an aryl group of C ₆ to C ₆₀ ; C ₆ ~ C ₆₀ allyloxy group; fluorenyl group; Any one of the heterogeneous groups from C ₂ to C ₆₀ is selected,
4) The L ₂ , R ₁₀ and R ₁₁ are the alkylene group, alkyl group, alkenyl group, alkoxy group, arylene group, aryloxy group, cycloalkyl group, hydroxy group, aryl group, fluorenyl group, and hetero ring. Each is a halogen; heavy hydrogen; C ₆ ~ C ₂₀ Silane group substituted or unsubstituted with an aryl group; siloxane group; 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 alkyne 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; It may be further substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₃₀ arylalkyl group and C ₈ ~ C ₃₀ arylalkenyl group, and these substituents may be combined with each other to form a ring.
According to clause 1,
The compound represented by Formula 1 is a composition for encapsulating an organic light-emitting device, which is one or more of the following compounds:























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

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