WO2019004764A1 - Composition d'encapsulation d'une diode électroluminescente organique, et dispositif d'affichage électroluminescent organique comprenant celle-ci - Google Patents

Composition d'encapsulation d'une diode électroluminescente organique, et dispositif d'affichage électroluminescent organique comprenant celle-ci Download PDF

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WO2019004764A1
WO2019004764A1 PCT/KR2018/007385 KR2018007385W WO2019004764A1 WO 2019004764 A1 WO2019004764 A1 WO 2019004764A1 KR 2018007385 W KR2018007385 W KR 2018007385W WO 2019004764 A1 WO2019004764 A1 WO 2019004764A1
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group
carbon atoms
ring
mmol
aryl
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PCT/KR2018/007385
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English (en)
Korean (ko)
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박용욱
이제우
강문성
박윤석
문성윤
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덕산네오룩스 주식회사
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Priority claimed from KR1020180034007A external-priority patent/KR102392802B1/ko
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Publication of WO2019004764A1 publication Critical patent/WO2019004764A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/844—Encapsulations
    • H10K50/8445—Encapsulations multilayered coatings having a repetitive structure, e.g. having multiple organic-inorganic bilayers

Definitions

  • the present invention relates to a UV-blocking resin composition, and a flexible sealing technique for protecting an organic light-emitting device from external stimuli including moisture, oxygen and light.
  • OLED organic light emitting diode
  • electrons injected from a cathode and holes injected from an anode are combined in an emission layer of an organic light emitting portion to form an electron-hole pair
  • a self-emitting flat panel display device in a process of recombination thereof.
  • the organic light emitting device exhibits high luminous efficiency in the three primary colors of red, green, blue and white, low driving voltage and power consumption, wide viewing angle, and high response speed of pixels, Have.
  • the organic light emitting device is being actively studied in the field of flexible display, since it can realize an ultra-thin and lightweight display capable of being manufactured with a thickness of 1 mm or less on a glass or plastic substrate.
  • the light emitting material and the electrode material are oxidized by oxygen or moisture, thereby causing problems such as a dark spot and a pixel shrinkage, resulting in a decrease in lifetime and efficiency.
  • the lifetime and efficiency of the OLED device are reduced due to external light including sunlight.
  • the sunlight has a light amount ratio of 2.5% of ultraviolet rays, 51.5% of visible rays, and 40.6% of ultraviolet rays.
  • ultraviolet ray has a small amount of light but it is energetically high and causes decomposition and deterioration of organic light emitting material, Is destroyed.
  • the organic material and the organic-metal material by UV are decomposed.
  • the organic and organic-metal materials of the organic light emitting device emit light when the light absorption occurs from the ground state to the singly excited state under the optical excitation and returns to the ground state.
  • the binding energy in the organic or organic-metal molecule may be similar to or lower than the energy of singlet excited state, and dissociation may occur at the binding site.
  • an addition reaction is carried out to form a neutral saturated decomposition product, which can act as an impurity.
  • the organic light emitting device receives external light (sunlight) for a long time
  • the organic material or the organic-metal material of the organic light emitting device receives a continuous stress due to the ultraviolet rays flowing into the device,
  • the coupling of the destroyed molecules causes a change in the color coordinates of the organic light emitting device, a driving voltage rise, and a reduction in the lifetime, so that the ultraviolet rays should be prevented from flowing into the organic light emitting device.
  • encapsulation techniques can be largely classified into three ways: Can (glass encapsulation), TFE (thin film encapsulation), and Hybrid.
  • Can glass encapsulation
  • TFE thin film encapsulation
  • Hybrid Each method can be performed by using a metal or glass cover plate having a gas barrier property and a Can Method and a TEF method called a face sealing method which implements a barrier property by organic or inorganic multilayer thin film on the upper layer and a plastic barrier film as a cover plate, It can be explained by the hybrid method of positioning the adhesive layer.
  • a sealing method is disclosed in Korean Patent Publication No. 2011-0071039.
  • Can (Glass encap) method widely used until now is a technology to seal the glass powder by melting with laser or to seal it with UV glue by placing organic light emitting element between two glass composed of substrate and lid,
  • the heat conduction characteristic is poor due to the inert gas in the device
  • the cost due to the glass processing is increased due to the large surface area, and it is difficult to apply it to the production of the flexible OLED panel requiring flexibility.
  • TFE Thin film encapsulation
  • the inorganic barrier layer may be a metal oxide / nitride such as AlxOy, SiOx, SiNy, SiOxNy, etc., and the inorganic barrier layer may be formed by sputtering (sputtering) on the organic barrier layer, deposition or plasma enhanced chemical vapor deposition (PECVD).
  • sputtering sputtering
  • PECVD plasma enhanced chemical vapor deposition
  • U.S. Patent No. 7767498 discloses that the barrier properties of moisture and oxygen are more advantageous as the number of pairs of the organic barrier layer and the inorganic barrier layer is larger.
  • the barrier properties of the barrier layer due to the foreign material incorporation And a decrease in the yield along with the decrease is reported as disadvantage.
  • the present invention provides an encapsulating material composition capable of protecting the organic light emitting element from ultraviolet light while having flexibility in film formation so as to be compatible with the development direction of a display which is converted from a rigid display to a flexible OLED.
  • Another object of the present invention is to provide a sealing composition capable of forming a thick film and having flexibility.
  • the encapsulant used in the present invention is intended to block ultraviolet rays of 400 nm or less and transmit light in a visible light region of 440 nm or more to protect the organic light emitting device from ultraviolet rays and not to lower the efficiency of the organic light emitting device.
  • the ultraviolet blocking agent included in the encapsulant used in the present invention absorbs ultraviolet rays of 400 nm or less and prevents ultraviolet rays from penetrating into the organic light emitting device, and must transmit visible light. This is calculated as the energy bandgap, which is a characteristic characteristic of organic materials.
  • the ultraviolet ray corresponds to an electron energy level of 3.1 [eV] or more, which corresponds to the energy bandgap of the material.
  • the ultraviolet screening agent included in the encapsulating composition of the present invention has an electron energy level of 2.95 to 3.1 [ev] since ultraviolet rays blocking 400 nm or less of ultraviolet rays should be blocked to 5% or less and visible light of 440 nm must be transmitted by 90% or more.
  • sealing composition of the present invention may contain an ultraviolet screening agent of the following formula (1).
  • an ultraviolet absorber having an aromatic derivative bonded to nitrogen of the present invention By using an ultraviolet absorber having an aromatic derivative bonded to nitrogen of the present invention, water, oxygen and ultraviolet rays penetrating from the outside after curing of the sealing composition can be blocked, thereby improving the reliability of the organic light emitting device.
  • FIG. 1 is an exemplary view illustrating an organic electroluminescent device according to an embodiment of the present invention.
  • FIG. 2 is a view schematically showing an example of the structure of an electronic device including an organic electroluminescent device.
  • 3 is a graph of transmittance according to embodiments of the present invention.
  • first, second, A, B, (a), and (b) may be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements.
  • halo or halogen
  • fluorine F
  • bromine Br
  • chlorine Cl
  • iodine I
  • alkyl or " alkyl group” refers to a straight or branched Alkyl " means a radical of a saturated aliphatic group, including alkyl, cycloalkyl-substituted alkyl groups.
  • haloalkyl group or halogenalkyl group as used in the present invention means an alkyl group substituted with halogen unless otherwise stated.
  • heteroalkyl group as used herein means that at least one of the carbon atoms constituting the alkyl group is replaced by a heteroatom.
  • alkenyl group or " alkynyl group”, as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms and include straight chain or branched chain groups, It is not.
  • cycloalkyl as used herein, unless otherwise specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.
  • alkoxy group means an alkyl group to which an oxygen radical is attached and, unless otherwise stated, has 1 to 60 carbon atoms, It is not.
  • alkenoyl group means an alkenyl group to which an oxygen radical is attached, , But is not limited thereto.
  • aryloxyl group or " aryloxy group” refers to an aryl group attached to an oxygen radical and, unless otherwise stated, has a carbon number of 6 to 60, but is not limited thereto.
  • aryl group and arylene group each have 6 to 60 carbon atoms, but are not limited thereto.
  • an aryl group or an arylene group means a single ring or a multicyclic aromatic group, and neighboring substituents include aromatic rings formed by bonding or participating in the reaction.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a fluorene group, a spirobifluorene group, or a spirobifluorene group.
  • aryl or ar means a radical substituted with an aryl group.
  • the arylalkyl group is an alkyl group substituted with an aryl group
  • the arylalkenyl group is an alkenyl group substituted with an aryl group
  • the radical substituted with an aryl group has the carbon number described in the present specification.
  • heteroalkyl as used herein, unless otherwise indicated, means an alkyl comprising one or more heteroatoms.
  • heteroaryl group or “ heteroarylene group” as used in the present invention means an aryl or arylene group having 2 to 60 carbon atoms each containing at least one heteroatom unless otherwise specified, And includes at least one of a single ring and a multi-ring, and neighboring functional devices may be formed in combination.
  • heterocyclic group includes one or more heteroatoms, has from 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings and includes a heteroaliphatic ring and hetero Aromatic rings. Adjacent functional groups may be combined and formed.
  • heteroatom refers to N, O, S, P or Si unless otherwise stated.
  • heterocyclic group may also include a ring containing SO 2 in place of the carbon forming the ring.
  • heterocyclic group includes the following compounds.
  • aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms and an "aliphatic ring” means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • ring refers to a fused ring consisting of an aliphatic ring of 3 to 60 carbon atoms or an aromatic ring of 6 to 60 carbon atoms or a heterocycle of 2 to 60 carbon atoms, or combinations thereof, Saturated or unsaturated ring.
  • hetero-compounds or hetero-radicals other than the above-mentioned hetero-compounds include, but are not limited to, one or more heteroatoms.
  • carbonyl refers to -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group of 2 to 20 carbon atoms, an alkenyl group of 2 to 20 carbon atoms, an alkynyl group of 2 to 20 carbon atoms, or a combination thereof.
  • ether used in the present invention refers to -RO-R 'wherein R or R' are each independently of the other hydrogen, an alkyl group of 1-20 carbon atoms, An aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
  • substituent R 1 When a is an integer of 0, substituent R 1 is absent. When a is an integer of 1, one substituent R 1 is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3 each coupled as follows: and wherein R 1 may be the same or different from each other, a is the case of 4 to 6 integer, and bonded to the carbon of the benzene ring in a similar way, while the display of the hydrogen bonded to the carbon to form a benzene ring Is omitted.
  • FIG. 1 is an illustration of an encapsulated device in accordance with an embodiment of the present invention.
  • a first electrode 120, a second electrode 180, and a second electrode 180 formed on a substrate 110 are formed between the first electrode 110 and the second electrode 180, And an organic material layer.
  • the first electrode 120 may be an anode and the second electrode 180 may be a cathode (cathode).
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic material layer may include a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, and an electron injecting layer 170 sequentially on the first electrode 120. At this time, the remaining layers except the light emitting layer 150 may not be formed.
  • An electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like, and the electron transport layer 160 may serve as a hole blocking layer.
  • the organic EL device 200 may include a protective layer or a light-efficiency-improvement layer (not shown) formed on one surface of the first electrode 120 and the second electrode 180, Capping layer).
  • the organic electroluminescent device 200 can be manufactured using a physical vapor deposition (PVD) method.
  • PVD physical vapor deposition
  • a first electrode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, A transport layer 160 and an electron injection layer 170, and then depositing a material usable as the second electrode 180 on the organic layer.
  • the organic material layer may be formed using a variety of polymer materials, not a vapor deposition method, or a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, It is possible to produce a smaller number of layers by a method such as a dipping process, a screen printing process, or a thermal transfer process. 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 forming method.
  • the organic electroluminescent device 200 may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
  • WOLED White Organic Light Emitting Device
  • WOLED has advantages of high resolution realization and fairness, and can be manufactured using existing color filter technology of LCD.
  • Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented.
  • a stacking method in which R (Red), G (Green) and B (Blue) light emitting parts are arranged side by side, and R, G and B light emitting layers are stacked up and down
  • a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light from the electroluminescence material.
  • CCM color conversion material
  • the organic electroluminescent device 200 may be one of an organic light emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.
  • OLED organic light emitting diode
  • OPC organic photoconductor
  • organic TFT organic transistor
  • Another embodiment of the present invention may include an electronic device including a display device including the above-described organic electroluminescent device 200 of the present invention and a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • the present invention may further include a sealing layer 300 for protecting the organic EL device 200.
  • the sealing layer 300 is a single layer.
  • the present invention is not limited thereto, and the sealing layer 300 may be formed of multiple layers. This configuration will be described with reference to FIG.
  • 2 is a view schematically showing an example of the structure of an electronic device including an organic electroluminescent device. 2 includes a substrate 110, an organic electroluminescent device 200 disposed on the substrate 110, and an encapsulant layer 300 disposed on the organic electroluminescent device 200.
  • the sealing layer 300 has three layers.
  • the sealing layer 300 may include two or more layers.
  • it may include an inorganic barrier layer and an organic barrier layer.
  • the first sealing layer 310 is an inorganic barrier layer
  • the second sealing layer 320 may be an organic barrier layer
  • the third sealing layer 330 may be an inorganic barrier layer.
  • the stacking order of the layers 310, 320, and 330 is not limited to this.
  • the organic barrier layer and the inorganic barrier layer may be alternately deposited to one layer or more and ten layers or less, preferably one layer or more and three layers or less.
  • the encapsulant layer 300 may form an organic barrier layer between the inorganic barrier layers for encapsulation or encapsulation of a flexible display device which is capable of curing the encapsulant composition .
  • the sealing composition organic barrier layer material
  • the initiator may include, without limitation, conventional photopolymerization initiators capable of carrying out photo-curable reactions.
  • photopolymerization initiator include triazine; Cetophenone system; Benzophenone type; Thioxanthone system; Benzoin; taking over; Oxime based or mixtures thereof.
  • triazines examples include 2,4,6-trichloro-s-triazine; 2-phenyl-4,6-bis (trichloromethyl) -s-triazine; 2- (3 ', 4'-dimethoxystyryl) -4,6-bis (trichloromethyl) -s-triazine; 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) -s-triazine; 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine; 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine; 2-biphenyl-4,6-bis (trichloromethyl) -s-triazine; Bis (trichloromethyl) -6-styryl-s-triazine; 2- (naphtho-1-yl) -4,6-
  • acetophenone-based compound examples include 2,2'-diethoxyacetophenone; 2,2'-dibutoxyacetophenone; 2-hydroxy-2-methylpropiophenone; p-tert-butyltrichloroacetophenone; p-t-butyldichloroacetophenone; 4-chloroacetophenone; 2,2'-dichloro-4-phenoxyacetophenone; 2-methyl-1- (4- (methylthio) phenyl) -2 -morpholinopropan-1-one; Benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one or mixtures thereof.
  • benzophenone examples include benzophenone; Benzoyl benzoic acid; Benzoyl benzoate; 4-phenylbenzophenone; Hydroxybenzophenone; Acrylated benzophenone; 4,4'-bis (dimethylamino) benzophenone; 4,4'-dichlorobenzophenone; 3,3'-dimethyl-2-methoxybenzophenone, or a mixture thereof.
  • Thioxanthone is thioxanthone; 2-methyl thioxanthone; Isopropyl thioxanthone; 2,4-diethyl thioxanthone; 2,4-diisopropylthioxanthone; 2-chlorothioxanthone, or a mixture thereof.
  • benzoin group examples include benzoin; Benzoin methyl ether; Benzoin ethyl ether; Benzoin isopropyl ether; Benzoin isobutyl ether; Benzyl dimethyl ketal, or mixtures thereof.
  • Examples of phosphorus compounds include bisbenzoylphenylphosphine oxide; Benzoyldiphenylphosphine oxide, or a mixture thereof.
  • the oxime system was prepared by reacting 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione and 1- (o-acetyloxime) 2-methylbenzoyl) -9H-carbazol-3-yl] ethanone, or mixtures thereof.
  • the initiator may be contained in an amount of 0.1 to 20% by weight, preferably 0.5 to 20% by weight, more preferably 0.5 to 10% by weight, and most preferably 0.5 to 7% by weight, based on the solid content.
  • photopolymerization can sufficiently take place at the time of exposure, and the transmittance can be prevented from being lowered due to the unreacted initiator remaining after the photopolymerization.
  • the light stabilizer itself does not have an ability to absorb ultraviolet light, but it is a light stabilizer having a photostabilizing effect in coexistence with a substance that absorbs ultraviolet light, and may include a conventional light stabilizer.
  • the light stabilizer may be a cyanoacrylate-based; Hindered amine series (HALS); A metal complex salt system or a mixture thereof.
  • 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-phenyl acrylate; Pentaerythritol tetrakis (2-cyano-3,3-diphenylacrylate); Ethane-1,2-diylbis (2-cyano-3,3-diphenylacrylate); 2- (acryloyloxy) ethyl 2-cyano-3, 3-diphenylacrylate; 2- (methacryloyloxy) ethyl 2-cyano-3, 3-diphenylacrylate; Propane-1,2,3-triyltris (2-cyano-3,3-diphenylacrylate) or mixtures thereof.
  • Hindered amine systems include tetrakis [methylene 3- (3,5-di-tert-butyl-4-hvdroxyphenyl) propionate] methane; Thiodiethylene bis [3 (3,5-di-tert-butyl-4-hvdroxyphenyl) propionate]; Octadecyl-3- (3,5-di-tert-butyl-4-hindoxyphenyl) propionate; Isotridecyl-3- (3,5-di-t-butyl-4-hindoxyphenyl) propionate; Hexamethyl (3,5-di-tert-butyl-4-hydroxydrosinamide); 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-hydroxybenzyl) phosphonate] or a mixture thereof.
  • the light stabilizer may be contained in the composition in an amount of 0.1 to 10% by weight, preferably 0.1 to 5% by weight, more preferably 0.1 to 3% by weight.
  • the function of the ultraviolet absorber can be maintained for a long time.
  • the formation of the organic barrier layer using photo-curing is performed by coating the sealing composition at 0.1 to 20 ⁇ , preferably 1 to 15 ⁇ , most preferably 1 to 10 ⁇ , at 10 to 500 mW / cm 2 for 1 to 60 seconds Irradiation and curing.
  • the curing rate may be 90% or more, preferably 93% or more.
  • the composition and the initiator not participating in the photo-curing reaction in the organic barrier layer are minimized and the pass-way of moisture and / or oxygen is suppressed, so that good barrier properties can be obtained.
  • the coated sealing composition when the sealing composition is cured (when an organic barrier layer is formed), the coated sealing composition may shrink, and the shrinkage may be about 1 to 20%, more preferably 1 to 15 %. ≪ / RTI > When the shrinkage ratio of the organic barrier layer is 20% or more, dark spots and pixel shrinkage occur due to oxygen and / or moisture penetration in the inorganic barrier layer. In addition, The occurrence of warpage in the formation of the multi-layered barrier layer may lead to bonding of the light emitting device.
  • the organic barrier layer of the sealing layer 300 comprises (A) 1 to 10% by weight of an ultraviolet screening agent represented by the following formula (1), (B) 20 to 70% (C) 5 to 40% by weight of mono (meth) acrylate and (D) 1 to 10% by weight of an initiator.
  • an ultraviolet screening agent represented by the following formula (1)
  • B 20 to 70%
  • C 5 to 40% by weight of mono (meth) acrylate
  • D 1 to 10% by weight of an initiator.
  • Ar 1 , Ar 2 and Ar 3 are each independently the same or different and are C 6 -C 60 aryl; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of a C 3 to C 30 aliphatic ring and a C 6 to C 30 aromatic ring; An alkyl group having 1 to 60 carbon atoms; An alkenyl group having 2 to 60 carbon atoms; An alkynyl group of C 2 to C 60 ; A C 1 to C 30 alkoxy group; An aryloxy group of C 6 to C 30 ; L'-N (Ar 4 ) (Ar 5 )
  • L ' is a single bond;
  • Ar 4 and Ar 5 are each independently the same or different and are C 6 -C 60 aryl; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of a C 3 to C 30 aliphatic ring and a C 6 to C 30 aromatic ring; An alkyl group having 1 to 60 carbon atoms; An alkenyl group having 2 to 60 carbon atoms; An alkynyl group of C 2 to C 60 ; A C 1 to C 60 alkoxy group; And an aryloxy group having 6 to 60 carbon atoms.
  • L ' is an aryl group, a fluorenyl group, an arylene group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group or a fluorenylene group; heavy hydrogen; A silane group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; Siloxyl group; Cyano; A nitro group; An alkyl thio group of C 1 to C 30 ; A C 1 to C 30 alkoxy group; An alkyl group having 1 to 30 carbon atoms; An alkenyl group having 2 to 30 carbon atoms; An alkynyl group of C 2 to C 30 ; A C 6 to C 30 aryl group; A C 6 -C 30 aryl group substituted with deuterium; A fluorenyl group; A heterocyclic group of C 2 ⁇ C
  • the aryl group may be an aryl group having 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, and the heterocyclic group may have 2 to 60 carbon atoms, preferably 2 carbon atoms More preferably 1 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and in the case of the alkyl group, the number of carbon atoms is 1 to 50, preferably 1 to 30, more preferably 1 to 20, May be an alkyl group of 1 to 10 carbon atoms.
  • the aryl group or the arylene group when the aryl group or the arylene group is the aryl group or the arylene group, the aryl group or the arylene group may be independently selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group or a phenylene group, a biphenylene group, Phenylene, phenylene, phenylene, phenylene, phenylene, phenylene, phenylene, phenylene, phenylene or phenylene.
  • Ar 1 , Ar 2 and Ar 3 in the above formula (1) May be a substituted or unsubstituted fluorenyl derivative.
  • L 'in the above formula (1) may be any one of the following formulas (a-1) to (a-4).
  • R 1 and R 2 are each independently the same or different and independently of one another are halogen; Hydrogen; heavy hydrogen; A silane group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; Siloxyl group; Cyano; A nitro group; An alkyl thio group of C 1 to C 30 ; A C 1 to C 30 alkoxy group; An alkyl group having 1 to 30 carbon atoms; An alkenyl group having 2 to 30 carbon atoms; An alkynyl group of C 2 to C 30 ; A C 6 to C 30 aryl group; A C 6 -C 30 aryl group substituted with deuterium; A fluorenyl group; A heterocyclic group of C 2 ⁇ C 30; A C 3 to C 30 cycloalkyl group; An arylalkyl group having 7 to 30 carbon atoms and an arylalkenyl group having 8 to 30 carbon atoms,
  • a, c and d are each an integer of 0 to 4
  • b is an integer of 0 to 6
  • e and f are integers of 0 to 3
  • a, b, c, d, e, and f are two or more, they are the same or different, and a plurality of R 1 s or a plurality of R 2 s or adjacent R 1 s and R 2 s are bonded to each other to form a ring
  • a, b, c, d, e, and f are two or more, they are the same or different, and a plurality of R 1 s or a plurality of R 2 s or adjacent R 1 s and R 2 s are bonded to each other to form a ring
  • X is any one of NR ', O, S and CR'R "
  • R 'and R " are each independently selected from the group consisting of hydrogen, C 6 -C 20 aryl, C 2 -C 20 heterocycle, and C 1 -C 20 alkyl, R 'and R " may combine with each other to form a ring with a spy.
  • R 1 , R 2 , R 'and R are the same as or different from each other selected from the group consisting of aryl, silane, siloxane, alkylthio, alkoxy, alkyl, alkenyl, If an alkyl group, an aryl alkenyl group is, each of halogen; deuterium; siloxane group;; C 6 ⁇ aryl group a substituted or unsubstituted silane group of the C 20 a cyano group; a nitro group; C 1 ⁇ Import alkylthio of C 30; an alkoxy group of C 1 ⁇ C 30; C 1 ⁇ alkyl group of C 30; C 2 ⁇ of the C 30 alkenyl; C 2 ⁇ alkynyl of C 30; a C 6 substituted with heavy hydrogen; C 6 ⁇ aryl group of C 30 aryl group ⁇ C 30; fluorene group; C 2 ⁇ heterocyclic group of C 30; C 3 ⁇
  • Ar 4 of Formula 1 And Ar 5 may be any one of the following formulas (b-1) to (b-4).
  • R 3 and R 4 are each independently the same or different and are halogen; Hydrogen; heavy hydrogen; A silane group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; Siloxyl group; Cyano; A nitro group; An alkyl thio group of C 1 to C 30 ; A C 1 to C 30 alkoxy group; An alkyl group having 1 to 30 carbon atoms; An alkenyl group having 2 to 30 carbon atoms; An alkynyl group of C 2 to C 30 ; A C 6 to C 30 aryl group; A C 6 -C 30 aryl group substituted with deuterium; A fluorenyl group; A heterocyclic group of C 2 ⁇ C 30; A C 3 to C 30 cycloalkyl group; An arylalkyl group having 7 to 30 carbon atoms and an arylalkenyl group having 8 to 30 carbon atoms,
  • a plurality of R 3 s or a plurality of R 4 s or adjacent R 3 s and R 4 s May be bonded to each other to form an aromatic ring or a heteroaromatic ring
  • X is any one of NR ', O, S and CR'R "
  • Each of A ring and B ring is independently selected from the group consisting of an aryl group having 6 to 30 carbon atoms and a heterocyclic group having 2 to 30 carbon atoms.
  • R 3 , R 4 , R 'and R are the same as or different from the above-mentioned aryl group, silane group, siloxane group, cyano group, nitro group, alkylthio group, alkoxy group, alkyl group, alkenyl group, alkynyl group, fluorenyl group, A substituted or unsubstituted C 6 -C 20 aryl group, a siloxane group, a cyano group, a nitro group, a C 1 -C 6 alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, A C 1 to C 30 alkyl group, a C 1 to C 30 alkoxy group, a C 1 to C 30 alkyl group, a C 2 to C 30 alkenyl group, a C 2 to C 30 alkynyl group, a C 6 to C 30 aryl group, an
  • composition for encapsulating an organic light emitting diode according to the present invention may contain at least two compounds different from each other among the compounds represented by the formula (1).
  • the (B) di (meth) acrylate contained in the composition for encapsulating an organic light emitting diode according to the present invention may be represented by the following formula (2).
  • R 5 and R 6 are hydrogen; heavy hydrogen; Tritium; An alkyl group having 1 to 60 carbon atoms; An alkenyl group having 2 to 60 carbon atoms; A C 1 -C 60 alkoxy group; A hydroxy group,
  • R 7 is a C 1 to C 60 alkylene group; A C 6 -C 60 arylene group; A fluorenylene group; It is selected by any one of the heterocyclic group of C 2 ⁇ C 60.
  • R 5 to R 7 is an alkyl group, an alkenyl group, an alkoxy group, a hydroxyl group, an alkylene group, an arylene group, a fluorenylene group, or a heterocyclic group, heavy hydrogen;
  • the aryl group may be an aryl group having 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, and the heterocyclic group may have 2 to 60 carbon atoms, preferably 2 carbon atoms More preferably 1 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and in the case of the alkyl group, the number of carbon atoms is 1 to 50, preferably 1 to 30, more preferably 1 to 20, May be an alkyl group of 1 to 10 carbon atoms.
  • the aryl group or the arylene group when the aryl group or the arylene group is the aryl group or the arylene group, the aryl group or the arylene group may be independently selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group or a phenylene group, a biphenylene group, Phenylene, phenylene, phenylene, phenylene, phenylene, phenylene, phenylene, phenylene, phenylene or phenylene.
  • the composition for encapsulating an organic luminescent element of the present invention can further increase the photo-curability and the viscosity of the composition because the di (meth) acrylate represented by the above-mentioned formula (2) is contained.
  • R 7 is a substituted or unsubstituted C 1 -C 60 alkylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted fluorenylene group, a substituted Or an unsubstituted C 2 to C 60 heterocyclic group, preferably a substituted or unsubstituted C 1 to C 60 alkylene group, a substituted or unsubstituted C 6 to C 60 arylene group, Preferably a substituted or unsubstituted C 1 to C 30 alkylene group.
  • the di (meth) acrylate is selected from the group consisting of octanediol di (meth) acrylate; Nonanediol (meth) acrylate; Decanediol di (meth) acrylate; Undecanediol (meth) acrylate; Dodecanediol (meth) acrylate; Decyl (meth) acrylate; Undecyl (meth) acrylate; Lauryl di (meth) acrylate; Tridecyl (meth) acrylate; Tetradecyl (meth) acrylate; Pentadecyldi (meth) acrylate; Hexadecyl (meth) acrylate; Heptadecyl (meth) acrylate; Octadecyl (meth) acrylate; Nonadecyldi (meth) acrylate; (Meth) acrylate, and the like, but are not
  • the mono (meth) acrylate (C) contained in the composition for encapsulating an organic luminescent element according to the present invention may be represented by the following formula (3).
  • L 1 is a single bond; An alkylene group of C 1 to C 26 ; A C 2 -C 26 alkenyl group; A C 1 to C 26 alkoxy group; An arylene group having 6 to 60 carbon atoms; A C 6 to C 60 aryloxy group,
  • R 5 is hydrogen; heavy hydrogen; Tritium; An alkyl group having 1 to 60 carbon atoms; A C 3 to C 30 cycloalkyl group; An alkenyl group having 2 to 60 carbon atoms; A C 1 to C 60 alkoxy group; A hydroxyl group,
  • R 7 is a C 6 to C 60 aryl group; An aryloxy group of C 6 to C 60 ; A fluorenyl group; C 2 to C 60 heteroatoms.
  • L 1 , R 5 and R 7 is an alkyl group, an alkenyl group, an alkoxy group, an arylene group, an aryloxy group, a cycloalkyl group, a hydroxyl group, an aryl group, a fluorenyl group or a heterocyclic ring, heavy hydrogen;
  • the aryl group may be an aryl group having 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, and the heterocyclic group may have 2 to 60 carbon atoms, preferably 2 carbon atoms More preferably 1 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and in the case of the alkyl group, the number of carbon atoms is 1 to 50, preferably 1 to 30, more preferably 1 to 20, May be an alkyl group of 1 to 10 carbon atoms.
  • the aryl group or the arylene group when the aryl group or the arylene group is the aryl group or the arylene group, the aryl group or the arylene group may be independently selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group or a phenylene group, a biphenylene group, Phenylene, phenylene, phenylene, phenylene, phenylene, phenylene, phenylene, phenylene, phenylene or phenylene.
  • R 7 is a phenylphenoxyethyl group; A phenoxyethyl group; Benzyl group; A phenyl group; Phenylphenoxy group; Phenoxy group; A phenylethyl group; Phenylpropyl group; A phenylbutyl group; Methylphenylethyl; Propylphenylethyl; A methoxyphenylethyl group; Cyclohexylphenylethyl group; Chlorophenylethyl; Bromophenylethyl group; A methylphenyl group; Methylethylphenyl group; A methoxyphenyl group; A propyl group; A cyclohexylphenyl group; Chlorophenyl group; Bromophenyl group; A phenyl phenyl group; A biphenyl group; A terphenyl group; A quaterphenyl group; Anthrac
  • the above-mentioned formula (3) is preferably an aromatic mono (meth) acrylate, and is specifically as follows.
  • the (meth) acrylate referred to in the present invention is not limited to only one example, and the present invention includes all acrylates having a structural isomer relationship.
  • the present invention includes at least one of 3-phenylethyl (meth) acrylate and 4-phenyl But is not limited thereto.
  • composition for encapsulating an organic light emitting diode according to the present invention may further comprise a light stabilizer.
  • the light stabilizer may be selected from the group consisting of (A) an ultraviolet light blocking agent, (B) di (meth) acrylate, (C) mono And 0.1 to 10% by weight based on the total amount of (D) initiator.
  • the compound represented by Formula 1 may be any one of the following compounds, and the compound represented by Formula 1 is not limited to the following compounds.
  • composition for encapsulating an organic light emitting diode according to the present invention may have a viscosity of 5 cps to 40 cps at 25 ° C.
  • composition for encapsulating an organic luminescent element according to the present invention may further comprise a photo-curable initiator.
  • the barrier layer formed on the organic light emitting device may include an inorganic barrier layer and an organic barrier layer, and the organic barrier layer may be a composition for encapsulating an organic luminescent element according to any one of claims 1 to 11 .
  • the organic barrier layer may be formed by inkjet, vacuum deposition, spin coating, or slit coating.
  • the light transmittance of the composition for encapsulating an organic light emitting diode according to the present invention may be less than 10% at 400 nm and at least 90% at 440 nm.
  • the composition for encapsulating an organic light emitting diode according to the present invention has a light transmittance of less than 5% at 400 nm and at least 90% at 430 nm, more preferably a light transmittance of the composition for encapsulating an organic light emitting element according to the present invention
  • the light transmittance at 405 nm is less than 10% and the light transmittance at 430 nm is at least 90%.
  • the light transmittance of the composition for encapsulating an organic light emitting device according to the present invention is less than 5% at 405 nm and 90% More preferably, the light transmittance of the composition for encapsulating an organic light emitting diode according to the present invention may be less than 5% at 410 nm and greater than 90% at 430 nm.
  • the compound represented by Formula 1 according to the present invention (Final Product 1) is prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below.
  • the compound of formula (1) according to the present invention is prepared by reacting Sub 1 and Sub 3 as shown in Reaction Scheme 2 below.
  • the compound of formula (1) according to the present invention is prepared by reacting Core 1 'and Sub 3' as shown in Reaction Scheme 3 below.
  • Sub 1 of Scheme 1 may be synthesized by the reaction path of Scheme 4 below, but is not limited thereto.
  • the compound belonging to Sub 1 may be, but not limited to, the following compounds, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 1.
  • Sub 3 of Scheme 2 can be synthesized by the reaction path of Scheme 5 below, but is not limited thereto.
  • the starting material Sub 1 (1) (15.00 g, 44.72 mmol) and 2,7-dibromo-9,9-dimethyl-9H-fluorene (16.53 g, 46.95 mmol) were dissolved in toluene (250 ml) in a round bottom flask after addition of Pd 2 (dba) 3 (2.05 g, 2.24 mmol), 50% P (t-Bu) 3 (1.80 ml, 4.47 mmol), NaOt-Bu (12.97 g, 134.15 mmol) and stirred at 80 °C Respectively. When the reaction was completed, water was added to complete the reaction. The organic layer was extracted, dried over MgSO 4 and concentrated. The resulting compound was subjected to silicagel column to obtain 17.71 g (yield: 65%) of the product.
  • the compound belonging to Sub 2 may be, but not limited to, the following compounds, and Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 2.
  • Core 1 'of Scheme 3 can be synthesized by the reaction path of Scheme 6 below, but is not limited thereto.
  • Sub 1 'of Scheme 6 can be synthesized by the reaction path of Scheme 7 below, but is not limited thereto.
  • the starting material 4- (naphthalen-1-yl) aniline (21.92 g, 100 mmol) and 9-chlorospiro [benzo [c] fluorene-7,9'- fluorene] (40.09 g, 100 mmol) was dissolved in toluene (330 ml), Pd 2 (dba) 3 (2.74 g, 3 mmol), 50% P (t-Bu) 3 (3.2 ml, 8 mmol), NaOt-Bu (28.83 g, 300 mmol) And the mixture was stirred under reflux. When the reaction was completed, water was added to complete the reaction. The organic layer was extracted, dried over MgSO 4 and concentrated. The resulting compound was subjected to silica gel column chromatography to obtain 29.76 g (yield: 51%) of the product.
  • the starting material 4- (naphthalen-1-yl) aniline (21.92 g, 100 mmol) and 2-chlorospiro [benzo [b] fluorene-11,9'- fluorene] (40.09 g, 100 mmol) was dissolved in toluene (330 ml), Pd 2 (dba) 3 (2.74 g, 3 mmol), 50% P (t-Bu) 3 (3.2 ml, 8 mmol), NaOt-Bu (28.83 g, 300 mmol) And the mixture was stirred under reflux. When the reaction was completed, water was added to complete the reaction. The organic layer was extracted, dried over MgSO 4 and concentrated. The resulting compound was subjected to silica gel column chromatography to obtain 28.01 g (yield: 48%) of the product.
  • Sub 2 'of Scheme 6 can be synthesized by the reaction path of Scheme 8 below, but is not limited thereto.
  • the compound represented by Formula 1 according to the present invention (Final Product 1) is prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below.
  • the compound of formula (1) according to the present invention is prepared by reacting Sub 1 and Sub 3 as shown in Reaction Scheme 2 below.
  • the starting material 9-chlorospiro [benzo [c] fluorene-7,9'-fluorene] (11.50 g, 28.68 mmol), Sub 1 (5) (11.81 g, 28.68 mmol), toluene (150 ml), Pd 2 a dba) 3 (1.31 g, 1.43 mmol), 50% P (t-Bu) 3 (1.16 ml, 2.87 mmol), NaOt-Bu (8.32 g, 86.05 mmol) proceeds in the same manner as in experiment way of the P-3 To obtain 18.72 g (yield: 84%) of the product.
  • Table 6 shows FD-MS (Field Desorption-Mass Spectrometry) values of the compounds for P-1 to P-114.
  • Table 7 shows FD-MS (Field Desorption-Mass Spectrometry).
  • Example 1 In Example 1, (A) 5.6 parts by weight of P-30 of the present invention as an ultraviolet screening agent, (B) 55.0 parts by weight of 1,10-decanediol diacrylate (TCI) as di (meth) 36.7 parts by weight of 3-phenoxybenzyl acrylate (KPX) as mono (meth) acrylate, 1.8 parts by weight of Darocur TPO (BASF) as an initiator (D), CHISORB 336 DBC) were placed in a 20 ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity of 18.5 cps at 25 ⁇ ).
  • TCI 1,10-decanediol diacrylate
  • KPX 3-phenoxybenzyl acrylate
  • BASF Darocur TPO
  • CHISORB 336 DBC CHISORB 336 DBC
  • Example 2 5.6 parts by weight of P-34 of the present invention as an ultraviolet screening agent (A2), 55.0 parts by weight of 1,10-decanediol diacrylate (TCI) as di (meth) acrylate (B) 36.7 parts by weight of 3-phenoxybenzyl acrylate (KPX) as mono (meth) acrylate, 1.8 parts by weight of Darocur TPO (BASF) as an initiator (D), CHISORB 336 DBC) were placed in a 20 ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity of 18.8 cps at 25 ⁇ ).
  • A2 ultraviolet screening agent
  • TCI 1,10-decanediol diacrylate
  • KPX 3-phenoxybenzyl acrylate
  • D 1.8 parts by weight of Darocur TPO
  • CHISORB 336 DBC CHISORB 336 DBC
  • Example 3 5.6 parts by weight of P-73 of the present invention as an ultraviolet screening agent, (B) 55.0 parts by weight of 1,10-decanediol diacrylate (TCI) as di (meth) acrylate, 36.7 parts by weight of 3-phenoxybenzyl acrylate (KPX) as mono (meth) acrylate, 1.8 parts by weight of Darocur TPO (BASF) as an initiator (D), CHISORB 336 DBC) were placed in a 20 ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity of 18.1 cps at 25 ⁇ ).
  • TCI 1,10-decanediol diacrylate
  • KPX 3-phenoxybenzyl acrylate
  • BASF Darocur TPO
  • CHISORB 336 DBC CHISORB 336 DBC
  • Example 4 5.6 parts by weight of P-76 of the present invention as an ultraviolet screening agent, (B) 55.0 parts by weight of 1,10-decanediol diacrylate (TCI) as di (meth) acrylate, 36.7 parts by weight of 3-phenoxybenzyl acrylate (KPX) as mono (meth) acrylate, 1.8 parts by weight of Darocur TPO (BASF) as an initiator (D), CHISORB 336 DBC Co., Ltd.) were put into a 20 ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity of 18.0 cps at 25 ⁇ ).
  • TCI 1,10-decanediol diacrylate
  • KPX 3-phenoxybenzyl acrylate
  • D Darocur TPO
  • CHISORB 336 DBC Co., Ltd. CHISORB 336 DBC Co., Ltd.
  • Example 5 In Example 5, (A5) 5.6 parts by weight of P-80 of the present invention as an ultraviolet screening agent, (B) 55.0 parts by weight of 1,10-decanediol diacrylate (TCI) as di (meth) acrylate, 36.7 parts by weight of 3-phenoxybenzyl acrylate (KPX) as mono (meth) acrylate, 1.8 parts by weight of Darocur TPO (BASF) as an initiator (D), CHISORB 336 DBC) were placed in a 20 ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity of 17.8 cps at 25 ⁇ ).
  • TCI 1,10-decanediol diacrylate
  • KPX 3-phenoxybenzyl acrylate
  • D Darocur TPO
  • CHISORB 336 DBC CHISORB 336 DBC
  • Example 6 In Example 6, (A6) 5.6 parts by weight of P-115 of the present invention as an ultraviolet screening agent, (B) 55.0 parts by weight of 1,10-decanediol diacrylate (TCI) as di (meth) acrylate, 36.7 parts by weight of 3-phenoxybenzyl acrylate (KPX) as mono (meth) acrylate, 1.8 parts by weight of Darocur TPO (BASF) as an initiator (D), CHISORB 336 DBC) were placed in a 20 ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity of 18.5 cps at 25 ⁇ ).
  • TCI 1,10-decanediol diacrylate
  • KPX 3-phenoxybenzyl acrylate
  • BASF Darocur TPO
  • CHISORB 336 DBC CHISORB 336 DBC
  • Example 7 5.6 parts by weight of P-116 of the present invention as a (A7) ultraviolet screening agent, (B) 55.0 parts by weight of 1,10-decanediol diacrylate (TCI) as di (meth) acrylate, 36.7 parts by weight of 3-phenoxybenzyl acrylate (KPX) as mono (meth) acrylate, 1.8 parts by weight of Darocur TPO (BASF) as an initiator (D), CHISORB 336 DBC) were put into 20 ml brown vials and mixed at room temperature for 2 hours using a shaker to prepare a bag composition (viscosity at 25 ⁇ , viscosity 19.4 cps).
  • TCI 1,10-decanediol diacrylate
  • KPX 3-phenoxybenzyl acrylate
  • D Darocur TPO
  • CHISORB 336 DBC CHISORB 336 DBC
  • Example 8 5.6 parts by weight of P-117 of the present invention as an ultraviolet screening agent, (B) 55.0 parts by weight of 1,10-decanediol diacrylate (TCI) as di (meth) acrylate, 36.7 parts by weight of 3-phenoxybenzyl acrylate (KPX) as mono (meth) acrylate, 1.8 parts by weight of Darocur TPO (BASF) as an initiator (D), CHISORB 336 DBC) were placed in a 20 ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity of 19.2 cps at 25 ⁇ ).
  • TCI 1,10-decanediol diacrylate
  • KPX 3-phenoxybenzyl acrylate
  • D Darocur TPO
  • CHISORB 336 DBC CHISORB 336 DBC
  • Example 9 5.6 parts by weight of P-118 of the present invention as the ultraviolet screening agent, (B) 55.0 parts by weight of 1,10-decanediol diacrylate (TCI) as di (meth) acrylate, 36.7 parts by weight of 3-phenoxybenzyl acrylate (KPX) as mono (meth) acrylate, 1.8 parts by weight of Darocur TPO (BASF) as an initiator (D), CHISORB 336 DBC) were put into a 20 ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity of 16.8 cps at 25 ⁇ ).
  • TCI 1,10-decanediol diacrylate
  • KPX 3-phenoxybenzyl acrylate
  • D Darocur TPO
  • CHISORB 336 DBC CHISORB 336 DBC
  • Example 1 5.6 parts by weight of P-119 of the present invention as a (A10) ultraviolet screening agent, (B) 55.0 parts by weight of 1,10-decanediol diacrylate (TCI) as di (meth) acrylate, 36.7 parts by weight of 3-phenoxybenzyl acrylate (KPX) as mono (meth) acrylate, 1.8 parts by weight of Darocur TPO (BASF) as an initiator (D), CHISORB 336 DBC) were placed in a 20 ml brown vial and mixed at room temperature for 2 hours using a shaker to prepare a sealing composition (viscosity of 16.6 cps at 25 ⁇ ).
  • TCI 1,10-decanediol diacrylate
  • KPX 3-phenoxybenzyl acrylate
  • D Darocur TPO
  • CHISORB 336 DBC CHISORB 336 DBC
  • the coated and cured films were measured for transmittance in the visible light region with Lambda 950 (Perkin Elmer).
  • GC / MS used a column of RTX-1 (length: 60 m, diameter: 0.25 mm, fixed bed thickness: 1 ⁇ m) as a column, helium gas (flow rate: 1.0 mL / min) 3: 1, the temperature condition is kept at 40 DEG C for 3 minutes, then the temperature is raised at a rate of 7 DEG C / min, and then the temperature is maintained at 300 DEG C for 5 minutes.
  • Outgassing was performed by placing 5 pieces of glass size 50 mm ⁇ 10 mm in a collecting container and heating at 100 ° C. for 30 minutes to analyze outgassing.
  • a calibration curve is prepared with 25 ng, 50 ng, 100 ng and 200 ng of a toluene solution in methanol, and R2 value is obtained as 0.99.
  • Table 8 summarized in Table 8 below.
  • A is the ratio of the intensity of the absorption peak of 1635cm -1 in the vicinity of the intensity of the absorption peak in the vicinity of 1720cm -1 for the cured film
  • B is in the vicinity of 1720cm -1 for the photocurable composition
  • Examples 1 to 10 and Comparative Examples 1 to 4 exhibited a light curing rate of 90% or more. It was also confirmed that the outgassing amounts of Examples 1 to 10 and Comparative Examples 1 to 4 which are photocurable compositions of the present invention were significantly lower than those of Comparative Examples.
  • the composition for encapsulating organic light emitting diodes of the present invention has a high photo-curability using a small amount of ultraviolet absorber, and is superior in light to 347 nm to 405 nm
  • the organic light emitting device can be protected from ultraviolet rays.
  • the sealing compositions of the comparative examples were inferior in blocking ability against light having a wavelength of 347 nm to 405 nm.

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Abstract

La présente invention concerne : une composition d'encapsulation d'un dispositif électroluminescent organique, capable d'améliorer la fiabilité d'un élément destiné à un dispositif par blocage de l'humidité et l'oxygène pénétrant depuis l'extérieur ; et un dispositif encapsulé comprenant ledit élément.
PCT/KR2018/007385 2017-06-30 2018-06-29 Composition d'encapsulation d'une diode électroluminescente organique, et dispositif d'affichage électroluminescent organique comprenant celle-ci WO2019004764A1 (fr)

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KR1020180034007A KR102392802B1 (ko) 2017-06-30 2018-03-23 유기발광소자 봉지용 조성물 및 이를 포함하는 유기발광 표시장치

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JP2020138925A (ja) * 2019-02-27 2020-09-03 株式会社リコー 化合物
US11053437B2 (en) 2019-06-28 2021-07-06 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent devices, organic electroluminescent device and electronic device

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