WO2020159130A1 - Agent d'encapsulation absorbant les ultraviolets pour dispositif électroluminescent, et dispositif électroluminescent le comprenant - Google Patents

Agent d'encapsulation absorbant les ultraviolets pour dispositif électroluminescent, et dispositif électroluminescent le comprenant Download PDF

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Publication number
WO2020159130A1
WO2020159130A1 PCT/KR2020/000923 KR2020000923W WO2020159130A1 WO 2020159130 A1 WO2020159130 A1 WO 2020159130A1 KR 2020000923 W KR2020000923 W KR 2020000923W WO 2020159130 A1 WO2020159130 A1 WO 2020159130A1
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Prior art keywords
group
formula
encapsulant
light
emitting device
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PCT/KR2020/000923
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English (en)
Korean (ko)
Inventor
남시욱
서영성
김경종
Original Assignee
코오롱인더스트리 주식회사
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Priority to JP2021541686A priority Critical patent/JP7232340B2/ja
Priority to CN202080011262.1A priority patent/CN113366660A/zh
Publication of WO2020159130A1 publication Critical patent/WO2020159130A1/fr

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
    • H01L33/52—Encapsulations
    • H01L33/56—Materials, e.g. epoxy or silicone resin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/48—Stabilisers against degradation by oxygen, light or heat
    • 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

Definitions

  • the present invention relates to a sealing material used to prevent deterioration of the light emitting device, and more particularly, by applying an indole-based compound having a UV blocking function as a sealing material, it is possible to improve the physical properties and life characteristics of the light emitting device It relates to a UV absorbing encapsulant for a light emitting device and a light emitting device comprising the same.
  • the light emitting device especially an organic light emitting device (OLED) is a self-emission type device having a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics. It has the advantage that it can be multicolored, and is widely used in a wide variety of fields.
  • OLED organic light emitting device
  • UV-absorbing agents such as oxanilide, hindered amine, and metal complexing agents (light stabilizers) have been studied to prevent device damage from UV. Not many documents have been published.
  • UV absorbers mainly absorb only the UV in the region of 260 to 380 nm, there is a problem in that UV in the region of more than that (for example, 380 to 430 nm) cannot be blocked. Therefore, there is a need to develop an encapsulant for a light emitting device capable of completely absorbing and blocking UV rays in the region of 260 to 380 nm or more and preventing damage from UV.
  • an object of the present invention is to apply an indole-based compound having excellent UV-blocking function and excellent heat-resistance and light-resistance as a sealing material, and an ultraviolet absorbing sealing material for a light-emitting element capable of improving physical properties and lifespan characteristics of a light-emitting element, and It is to provide a light emitting device comprising.
  • the present invention includes an indole-based derivative compound represented by the following Chemical Formula 1, and has an initial transmittance of Equation 1 below and a light/heat resistance transmittance of Equation 2 below.
  • an absorbent encapsulant Provide an absorbent encapsulant.
  • R 1 and R 4 to R 7 are each independently selected from the group consisting of hydrogen, a hydroxy group, a halogen group, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms
  • R 2 And R 3 are each independently a linear, branched, or cyclic hydrocarbon group having 4 to 10 carbon atoms, which may or may not contain any one or more of nitrogen and oxygen atoms
  • T 0 is It is the initial transmittance at the wavelength
  • T 1 is the transmittance after light exposure at the wavelength.
  • the present invention provides a light emitting device comprising the ultraviolet absorbing encapsulant for the light emitting device.
  • the ultraviolet absorbent encapsulant for a light emitting device according to the present invention and the light emitting device including the same has an ultraviolet ray blocking function and applies an indole-based compound having excellent heat resistance and light resistance as a sealing material, thereby improving physical properties and lifespan characteristics of the light emitting device. It has the advantage of being able to.
  • the ultraviolet absorbent encapsulant for a light emitting device includes an indole-based derivative compound represented by Formula 1 below, and is characterized by having an initial transmittance of Formula 1 and a light/heat resistance transmittance of Formula 2 below.
  • R 1 and R 4 to R 7 are each independently selected from the group consisting of hydrogen, a hydroxy group, a halogen group, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms
  • R 2 And R 3 are each independently a linear, branched, or cyclic hydrocarbon group having 4 to 10 carbon atoms, which may or may not contain any one or more of nitrogen and oxygen atoms
  • T 0 is It is the initial transmittance at the wavelength
  • T 1 is the transmittance after light exposure at the wavelength.
  • UV absorbers such as cyanoacrylate, oxanilide, hindered amine, and metal complex (light stabilizers) were used.
  • UV absorbers mainly absorb only the UV in the 260 to 380 nm region, there is a problem that the UV in the region (eg, 400 to 430 nm) beyond that cannot be blocked. Accordingly, the present applicant has invented an encapsulation material for a light emitting device capable of completely absorbing and preventing UV damage in the region of 260 to 380 nm or more.
  • 405 nm was selected as the measurement wavelength in Equations 1 and 2 is that it has a characteristic of decreasing reliability (yellowing element damage, etc.) in the vicinity of 400 nm, and it is necessary to block the corresponding part.
  • Blue for maintaining RGB white balance and increasing transmittance (Blue) The transmittance in the wavelength range of 430 nm or higher should be high. That is, since it is important to absorb light around 400 nm that affects reliability and ensure transmittance at 430 nm or more, 405 nm is selected as the measurement wavelength as described above.
  • R 1 and R 4 to R 7 are each independently selected from the group consisting of hydrogen, a hydroxy group, a halogen group, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms, R 1 is preferably an alkyl group having 1 to 5 carbon atoms, more preferably a methyl group, and R 4 to R 7 are preferably hydrogen.
  • R 2 and R 3 are each independently a linear, branched, or cyclic hydrocarbon group having 4 to 10 carbon atoms, which may or may not contain any one or more of nitrogen and oxygen atoms
  • R 2 and R 3 are each independently a phenyl group, or a cyano group (-CN group), an alkyl group, an alkoxy group, a carbonyl group, a carboxyl group, a hydroxyl group, an amide group, an ester group, an ether group, an acrylate group or a halogen group It is a saturated or unsaturated (or polymerizable group) hydrocarbon group containing any one or more.
  • R 2 and R 3 are, ,
  • Etc. (in the above examples, the curve ) Denotes a connecting part), and any substituents satisfying the above conditions may be applied without particular limitation.
  • R 2 and R 3 may be the same or different, but preferably applied differently, for example, if any one of R 2 and R 3 is a phenyl group, the other may be any of the other illustrated substituents. have.
  • the ultraviolet absorbent encapsulant for a light emitting device in order to absorb UV of a wider range of wavelengths and to express a complementary effect with an indole-based compound, in addition to the indole-based compound, a benzophenone-based compound, tria Triazole-based compound, benzotriazole-based compound, triazine-based compound, salicylate-based compound, cyanoacrylate-based compound, oxanilide-based compound Compounds, hindered amine (hindered amine) compound and a metal complex salt-based compound (light stabilizer) may further include one or more UV absorbers.
  • the content of the additional UV absorber may be 0.05 to 5 parts by weight based on 100 parts by weight of the indole-based compound.
  • the blocking rate effect may be insignificant, and when it exceeds 5 parts by weight, viscosity of the crude liquid increases and precipitation occurs, and long-term crude liquid stability decreases. Can be.
  • the ultraviolet absorbent encapsulant for a light emitting device may include a monofunctional acrylate monomer, a polyfunctional acrylate monomer, and a reaction initiator in addition to the UV absorbers (including indole-based compounds).
  • the monofunctional acrylate monomer includes one acrylate functional group, benzyl methacrylate, 2-hydroxyethyl methacrylate, 4-hydroxybutyl methacrylate, and 2-hydroxypropyl methacrylate , 2-hydroxybutyl methacrylate, 6-hydroxyhexyl methacrylate, 1,4-cyclohexanedimethanol monomethacrylate, 1-chloro-2-hydroxypropyl methacrylate, diethylene glycol monomethacrylate Acrylate, 1,6-hexanediol monomethacrylate, 2-hydroxy-3-phenoxypropyl methacrylate, 4-hydroxycyclohexyl methacrylate, 2-hydroxy-3-phenoxybutyl methacrylate Rate, 4-hydroxycyclohexyl methacrylate, and mixtures including two or more of them.
  • the polyfunctional acrylate monomer includes two or more acrylate functional groups, and may include a polycyclic alicyclic skeleton or a polycyclic aromatic skeleton, diphencarritriol hexaacrylate, triethylene glycol di(meth). Acrylate, tricyclodecane dimethanol di(meth)acrylate, isobornyl dimethanol di(meth)acrylate, dicyclopentenyl dimethanol di(meth)acrylate, and mixtures including two or more of these may be exemplified, It is not limited to this.
  • reaction initiator is diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide (diphenyl (2,4,6,-trimethylbenzoyl) phosphine oxide), having the same or similar properties (i.e., 365 to Reaction initiators having a wavelength region of light absorption at 400 nm) and mixtures including two or more of them, but are not limited thereto.
  • the content of the UV absorber (including the indole-based compound) is 0.5 to 9% by weight, preferably 1 to 7% by weight %
  • the content of the monofunctional acrylate monomer is 3 to 95% by weight, preferably 40 to 80% by weight
  • the content of the polyfunctional acrylate monomer is 3 to 95% by weight, preferably 15 to 60% by weight
  • the content of the initiator may be 0.1 to 5% by weight, preferably 1 to 3% by weight.
  • each of these contents is only optimized for the present invention and is not limited to the above numerical range, and there is no particular limitation on the content of each component constituting the encapsulant as long as the object of the present invention can be achieved.
  • the ultraviolet absorbent encapsulant for a light emitting device may further include one or more additives selected from the group consisting of antioxidants, thermal stabilizers, surfactants, leveling agents and antifoaming agents.
  • the additive can be used without limitation within a limit that does not inhibit the expression of the effect by the indole-based compound.
  • the ultraviolet absorbent encapsulant for a light emitting device according to the present invention is excellent in heat/light resistance under light or heat conditions, as well as ultraviolet light (especially UV in the wavelength range of 405 to 430 nm), thereby preventing deterioration in physical properties of the light emitting device This can ultimately improve the life characteristics of the light emitting device.
  • the ultraviolet absorbent encapsulant for a light emitting device of the present invention has an initial transmittance of Equation 1 below and a light/heat resistance transmittance of Equation 2 below.
  • T 0 is an initial transmittance at a corresponding wavelength
  • T 1 is a transmittance after light exposure at a corresponding wavelength
  • the ultraviolet absorbent encapsulant for a light-emitting device of the present invention should basically satisfy Equation 1 (if the transmittance is 20% or less at 405 nm, it is all included in the Equation 1), and after light/heat resistance (light resistance, heat resistance), Equation 2 must be satisfied at the same time (if there are many changes at 405 nm after reliability, the light/heat resistance transmittance exceeds 10%).
  • the initial UV transmittance of the UV absorbing encapsulant for a light emitting device according to the present invention may be, for example, 60 to 100%, preferably 80 to 95%, as shown in Equation 1 above at a wavelength of 405 to 430 nm. .
  • the light transmittance for example, through the UV treatment experiment according to the KS C IEC 61646 standard (280 nm ⁇ 400 nm) to test the degree of deterioration depending on the case of exposure to sunlight, before and after exposure It can be confirmed by measuring the change in permeability.
  • light resistance should satisfy 10% or less as shown in Equation 2 above , Preferably 7% or less.
  • the failure to satisfy 10% or less means that the blocking performance of 405 nm is reduced by light exposure, and in this case, the life of the device may be shortened.
  • the heat resistance transmittance (heat resistance), for example, can be measured under conditions of heating for 500 to 1,000 hours at a temperature of 120 °C, the heat resistance under the conditions thereof is 10% or less, as shown in the formula (2), preferably It can be less than 7%.
  • the formula 2 for convenience of explanation, the term light-resistant/heat-resistant transmittance was used, and it is stated that the light-resistant transmittance and the heat-resistant transmittance are applied to the same formula.
  • the present invention provides a light emitting device comprising the above-described ultraviolet absorbing encapsulant for the light emitting device. That is, the UV absorbing encapsulant according to the present invention is applicable to conventional light emitting devices such as a light emitting device (LED) and an organic light emitting device (OLED), and is damaged by light from outside in addition to being damaged by oxygen and moisture. It is preferable to apply to the organic light emitting device in consideration of the point that the life of the device decreases. In addition, the basic configuration of the light emitting element and the organic light emitting element except for the encapsulant is generally applied to the contents thereof.
  • LED light emitting device
  • OLED organic light emitting device
  • a light emitting device including the UV absorbing encapsulant first, flash evaporation or inkjet printing (Ink-Jet Printing), spin coating the UV absorbing encapsulant for the light emitting device After coating the LED or OLED through a coating method such as UV curing, and then molding it in the form of a sheet, etc., bonding with a substrate and heat curing, a light emitting device including a sealing material can be manufactured.
  • a coating method such as UV curing
  • the compound obtained through agitation was operated on a glass substrate using a spin coater (ACE-200, Donga Trading) for 23 seconds at a speed of 880 rpm, and then at a temperature of 25° C. with a 395 nm wavelength LED curing machine under a nitrogen atmosphere of 1,500 Cured to a light amount of mJ / cm 2 , to prepare an ultraviolet absorbent encapsulant for a light emitting device having a thickness of 8 ⁇ m.
  • ACE-200, Donga Trading a spin coater
  • Example 1 Except that the indole-based derivative compound of Formula 1a was changed to the indole-based derivative compound represented by Formula 1c below, it was performed in the same manner as in Example 1 to prepare an ultraviolet absorbent encapsulant for a light emitting device.
  • Example 1 Except for changing the indole derivative compound of Formula 1a to the indole derivative compound represented by Formula 1d below, it was performed in the same manner as in Example 1 to prepare a UV absorbing encapsulant for a light emitting device.
  • Example 1 Except for changing the indole derivative compound of Formula 1a to the indole derivative compound represented by Formula 1e below, it was performed in the same manner as in Example 1 to prepare a UV absorbing encapsulant for a light emitting device.
  • Example 1 Except that the indole-based derivative compound of Formula 1a was changed to the indole-based derivative compound represented by the following Formula 1f, the same procedure as in Example 1 was performed to prepare a UV absorbing encapsulant for a light emitting device.
  • Example 1 Except for changing the indole derivative compound represented by Formula 1a to the indole derivative compound represented by Formula 1g, the same procedure as in Example 1 was performed to prepare a UV absorbing encapsulant for a light emitting device.
  • Example 1 Except for changing the indole derivative compound represented by Formula 1a to the indole derivative compound represented by Formula 1h, the same procedure as in Example 1 was performed to prepare a UV absorbing encapsulant for a light emitting device.
  • Example 1 Except that the indole-based derivative compound of Formula 1a was changed to a triazine-based UV absorber (BASF Tinuvin-460), the same procedure as in Example 1 was performed to prepare a sealing material for a light emitting device.
  • BASF Tinuvin-460 a triazine-based UV absorber
  • Example 1 Except that the indole-based derivative compound of Formula 1a was changed to a benzotriazole-based UV absorber (BASF Tinuvin-P), the same procedure as in Example 1 was performed to prepare a sealing material for a light emitting device.
  • BASF Tinuvin-P benzotriazole-based UV absorber
  • Example 1 Except that the indole-based derivative compound of Formula 1a was changed to a benzophenone-based UV absorber (BASF Chimassorb-81), the same procedure as in Example 1 was performed to prepare a sealing material for a light emitting device.
  • BASF Chimassorb-81 a benzophenone-based UV absorber
  • UV-Visible Spectrometer UV-Visible Spectrometer, Evolution 600
  • the transmittance of the encapsulant specimens prepared in Examples 1 to 10 and Comparative Examples 1 to 3 was measured in a transmission mode of 300 to 800 nm. The results are shown in Table 1 below.
  • the encapsulant prepared from Examples 1 to 10 and Comparative Examples 1 to 3 is the sun
  • the change in transmittance before and after was measured by testing the degree of deterioration depending on the case of exposure to light.
  • the light transmittance of each encapsulant was evaluated by light exposure at a temperature of 60° C. and a light amount of 15 kwh/m 2 according to the specification using a 2,500 W xenon arc lamp, and the results are shown in Table 2 below.
  • the encapsulants prepared from Examples 1 to 10 and Comparative Examples 1 to 3 were heated in an air state at a temperature of 120° C. for 500 hours using a high-temperature oven (Jeotech) to evaluate the heat-resistant transmittance of each encapsulant.
  • Table 2 The results are shown in Table 2 below.
  • Examples 1 to 10 of applying the indole derivative compound of the present invention The encapsulant was confirmed to have excellent short-wavelength, that is, a light blocking effect of 405 to 430 nm even after heat-resistant light.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Organic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Power Engineering (AREA)
  • Computer Hardware Design (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Physics & Mathematics (AREA)
  • Led Device Packages (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Sealing Material Composition (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)

Abstract

La présente invention concerne un agent d'encapsulation absorbant les ultraviolets pour un dispositif électroluminescent, et un dispositif électroluminescent le comprenant, l'agent d'encapsulation absorbant les ultraviolets ayant un composé à base d'indole utilisé en tant qu'agent d'encapsulation et présentant une fonction de blocage des ultraviolets de façon à avoir une excellente résistance à la chaleur et une excellente fiabilité de résistance à la lumière, ce qui permet d'améliorer les propriétés physiques et la durée de vie d'un dispositif électroluminescent.
PCT/KR2020/000923 2019-01-28 2020-01-20 Agent d'encapsulation absorbant les ultraviolets pour dispositif électroluminescent, et dispositif électroluminescent le comprenant WO2020159130A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2021541686A JP7232340B2 (ja) 2019-01-28 2020-01-20 発光素子用紫外線吸収封止材及びこれを含む発光素子
CN202080011262.1A CN113366660A (zh) 2019-01-28 2020-01-20 用于发光装置的紫外线吸收密封剂和包括该紫外线吸收密封剂的发光装置

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KR1020190010387A KR102113537B1 (ko) 2019-01-28 2019-01-28 발광 소자용 자외선 흡수 봉지재 및 이를 포함하는 발광 소자
KR10-2019-0010387 2019-01-28

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JP (1) JP7232340B2 (fr)
KR (1) KR102113537B1 (fr)
CN (1) CN113366660A (fr)
TW (1) TWI734358B (fr)
WO (1) WO2020159130A1 (fr)

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