WO2014208849A1 - 광경화 조성물 및 이를 포함하는 봉지화된 장치 - Google Patents
광경화 조성물 및 이를 포함하는 봉지화된 장치 Download PDFInfo
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- WO2014208849A1 WO2014208849A1 PCT/KR2013/011783 KR2013011783W WO2014208849A1 WO 2014208849 A1 WO2014208849 A1 WO 2014208849A1 KR 2013011783 W KR2013011783 W KR 2013011783W WO 2014208849 A1 WO2014208849 A1 WO 2014208849A1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
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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
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/296—Organo-silicon compounds
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
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- 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
Definitions
- the present invention relates to a photocurable composition and an encapsulated device comprising the same.
- a small organic light emitting device for mobile uses a method of filling a space between a substrate on which a device is deposited and a substrate covering the substrate with a non-reactive inert gas as a filler.
- a non-reactive inert gas as a filler.
- filling with inert gas between substrates as in the past may cause bending due to the weight of the glass substrate.
- the entire panel and the organic light emitting diode may be damaged by an external impact.
- An object of the present invention is to provide a photocurable composition capable of realizing a barrier layer for encapsulation of a device member having high photocurability, high adhesion to an inorganic barrier layer after curing, and high reliability.
- Another object of the present invention is to provide a photocurable composition capable of forming a barrier layer for encapsulation of an environment sensitive device member.
- Yet another object of the present invention is to provide an encapsulated device comprising a barrier layer formed of the photocurable composition.
- the photocurable composition of the present invention may include (A) a cyano group-containing silicone-based photocurable monomer represented by Formula 1 and (B) an initiator:
- the (A) cyano group-containing silicon-based photocuring monomer may be included alone or in two or more kinds.
- the photocurable composition may comprise a mixture of the (A) cyano group-containing silicone-based photocuring monomer of mono (meth) acrylate type and the (A) cyano group-containing silicone-based photocuring monomer of di (meth) acrylate type. have.
- the photocurable composition may further include one or more of (C) non-cyano-based silicon-containing photocurable monomer, (D) non-silicone photocurable monomer.
- composition for encapsulating an organic light emitting device of the present invention may include the photocurable composition.
- An encapsulated device of the invention comprises a device member; And a barrier stack formed on the device member, the barrier stack comprising an inorganic barrier layer and an organic barrier layer, wherein the organic barrier layer may be formed of the photocurable composition.
- the present invention provides a photocurable composition having high photocurability, a high adhesion to the inorganic barrier layer after curing, and a highly reliable barrier layer, which can be used for sealing the device member.
- FIG. 1 is a cross-sectional view of an encapsulated organic light emitting display device according to an embodiment of the present invention.
- FIG. 2 is a cross-sectional view of an encapsulated organic light emitting display device according to another embodiment of the present invention.
- '*' is an inter-element linkage site.
- hetero- means one to three heteroatoms selected from the group consisting of N, O, S, and P in one functional group, and the remainder is carbon unless otherwise defined.
- alkyl group means a linear saturated aliphatic hydrocarbon group unless otherwise defined.
- the alkyl group may be an alkyl group having 1 to 20 carbon atoms. More specifically, the alkyl group may be an alkyl group having 1 to 10 carbon atoms or an alkyl group having 1 to 6 carbon atoms.
- an alkyl group having 1 to 4 carbon atoms means that the alkyl chain contains 1 to 4 carbon atoms, and methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t- Selected from the group consisting of butyl.
- the alkyl group means, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group and the like.
- an "aryl group” refers to a substituent in which all elements of a cyclic substituent have p-orbitals, and these p-orbitals form a conjugate, and are monocyclic or fused ring polishes. It includes a click (ie, a ring that divides adjacent pairs of carbon atoms) functional groups.
- heteroaryl group means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, and P in the aryl group, and the rest are carbon.
- heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.
- a substituted or unsubstituted aryl group and / or a substituted or unsubstituted heteroaryl group includes a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted group Substituted phenanthryl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted m-terphenyl group , Substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted peryleney
- (meth) acrylate may mean acrylate and / or methacrylate.
- the photocurable composition of an embodiment of the present invention may include (A) a cyano group (-CN) -containing silicon-based photocuring monomer (hereinafter referred to as (A) photocuring monomer) and (B) initiator.
- A) photocuring monomer By containing a photocuring monomer, it is possible to increase the photocuring rate of the photocurable composition, and when used as a sealing composition to increase the adhesion to the inorganic barrier layer when forming the organic barrier layer after curing, when sealing the member for the device The reliability of the device member can be improved.
- the photocurable monomer has a cyano group, a silicone, and a photocurable functional group (for example, a (meth) acrylate group and a vinyl group), for example, di (meth) acrylate and tri (meth) acryl Polyfunctional (meth) acrylates such as late, tetra (meth) acrylate, penta (meth) acrylate or hexa (meth) acrylate, or mono (meth) acrylate.
- the (A) photocuring monomer may be represented by the formula (1):
- R 1 and R 2 are each independently hydrogen, a substituted or unsubstituted C 1-10 alkyl group, a substituted or unsubstituted C 2-10 heteroalkyl group, a substituted or unsubstituted C 6-20 aryl group, Substituted or unsubstituted heteroaryl group having 4-20 carbon atoms, substituted or unsubstituted An arylalkyl group having 7 to 21 carbon atoms, a substituted or unsubstituted silyl group having 1 to 10 carbon atoms, or the following Chemical Formula 2,
- R 4 is hydrogen or an alkyl group having 1-5 carbon atoms
- At least one of R 1 and R 2 is the formula (2)
- R 3 is hydrogen, a hydroxyl group, a halogen, -NR'R "(R ', R” is each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 10 carbon atoms , A substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms, or a substituted or unsubstituted arylalkyl group having 7 to 21 carbon atoms), a substituted or unsubstituted carbon atom 1-10 alkyl group, substituted or unsubstituted C2-C10 heteroalkyl group, substituted or unsubstituted C6-C20 aryl group, substituted or unsubstituted C4-20 heteroaryl group, substituted or unsubstituted An arylalkyl group
- X 1 , X 2 are each independently a single bond or oxygen
- X 3 , Y 1 and Y 2 are each independently a substituted or unsubstituted C 1-10 alkylene group, a substituted or unsubstituted C 2-10 heteroalkylene group, a substituted or unsubstituted C 6-20 An arylene group, a substituted or unsubstituted arylalkylene group having 7 to 21 carbon atoms, a substituted or unsubstituted heteroarylene group having 4 to 20 carbon atoms, or a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms).
- R 1 and R 2 may be each independently hydrogen, an alkyl group having 1 to 9 carbon atoms, or Chemical Formula 2, and at least one of R 1 and R 2 may be Chemical Formula 2.
- R 3 may be an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms.
- X ⁇ 3> , Y ⁇ 1> and Y ⁇ 2> are a C1-C10 alkylene group, a C1-C9 alkylene group, a C1-C8 alkylene group, a C1-C7 alkylene group, a C1-C6 It may be an alkylene group or an alkylene group having 1 to 5 carbon atoms.
- the photocurable monomer (A) may be prepared by reacting a cyano group-containing silicone compound with a photocurable functional group-containing compound, but is not limited thereto.
- the photocuring monomer may be included in the photocuring composition alone or in mixture of two or more thereof.
- the photocurable composition is a di (meth) acrylate type (A) photocuring monomer alone, or a mono (meth) acrylate type (A) photocuring monomer and a di (meth) acrylate type (A) view.
- Mono (meth) acrylate type (A) photocuring monomer in the mixture: di (meth) acrylate type (A) photocuring monomer is about 1: 0.5 to 1: 2, specifically about 1: 0.5, about 1: 1, about 1: 1.5, or about 1: 2 by weight. In the above range, it is possible to improve the photocurability of the photocurable composition and the adhesion to the inorganic barrier layer, and when used in the device for the device does not cause discoloration and decrease in transparency, thereby improving reliability.
- the photocurable monomer is about 1 to 99% by weight, for example about 90 to 99% by weight, specifically about 90,91,92,93,94,95,96,97,98 in the solid content photocurable composition Or 99 weight percent, or about 40 to 55 weight percent, specifically about 40,41,42,43,44,45,46,47,48,49,50,51,52,53,54 or 55 weight percent May be included.
- the photocuring degree of the photocurable composition is high, there may be an excellent effect of adhesion to the inorganic barrier layer after curing and good reliability.
- the initiator (B) is to initiate a photocuring reaction of the (A) photocuring monomer, and may include, without limitation, a conventional photopolymerization initiator capable of carrying out the photocuring reaction.
- the (B) initiator may include triazine, acetophenone, benzophenone, thioxanthone, benzoin, phosphorus, oxime or mixtures thereof, for example diphenyl (2, 4,6-trimethylbenzoyl) phosphine oxide, but is not limited thereto.
- the initiator is about 1 to 99% by weight in the photocurable composition, for example about 1 to 10% by weight, specifically about 1,2,3,4,5,6,7,8,9 or 10 weight percent, or for example about 1 to 5 weight percent, specifically about 1,2,3,4 or 5 weight percent.
- photopolymerization can occur sufficiently during exposure, and the transmittance can be prevented from being lowered due to the unreacted initiator remaining after the photopolymerization.
- the photocurable composition of one embodiment of the invention will comprise from about 1 to 99% by weight of the photocurable monomer (A) and from about 1 to 99% by weight of the initiator (B) in solids (A) + (B) Can be.
- the photocuring degree of the photocurable composition is high, there may be an excellent effect of adhesion to the inorganic barrier layer after curing and good reliability.
- the photocurable composition may comprise about 90 to 99 weight percent of (A) photocuring monomer and about 1 to 10 weight percent of initiator (B) in solids (A) + (B).
- the photocurable composition may comprise about 40 to 55% by weight of mono (meth) acrylate type (A) photocuring monomer, about 40 to 55% by weight of di (meth) acrylate type (A) photocuring monomer and (B And about 1 to 5 weight percent of initiator.
- the photocuring degree of the photocurable composition is high, there may be an excellent effect of adhesion to the inorganic barrier layer after curing and good reliability.
- the photocurable composition is a solvent-free type containing no solvent, and may be prepared by mixing the above-mentioned (A) photocuring monomer and (B) initiator.
- the photocurable composition may have a photocurability of at least about 90%, for example about 90-95%. In the above range, it is possible to use for encapsulation by realizing a layer that does not generate a shift after curing hardening shrinkage stress.
- the photocurable composition may have an adhesion of about 20 kgf or more to the inorganic barrier layer after curing.
- the inorganic barrier layer may include, but is not limited to, inorganic barrier layers (eg, SiOx, SiNx, Al 2 O 3 ) as detailed below.
- the adhesion to the inorganic barrier layer is about 20 to 100 kgf For example, about 25 to 100 kgf.
- the adhesion to the inorganic barrier layer of silicon oxide or aluminum oxide can be about 25-55 kgf. In another embodiment, the adhesion to the inorganic barrier layer of silicon nitride can be about 25 to 46 kgf.
- Device components in particular display members, can be degraded or deteriorated by permeation of gases or liquids in the surrounding environment, for example oxygen and / or moisture and / or water vapor and / or chemicals used in electronics in the atmosphere.
- the member for the device needs to be encapsulated or encapsulated.
- Members for such devices include organic light emitting diodes (OLEDs), lighting devices, flexible organic light emitting diode displays, metal sensor pads, microdisk lasers, electrochromic devices, photochromic devices, microelectromechanical systems, solar cells, integrated circuits. , Charge coupling devices, light emitting polymers, light emitting diodes, and the like, but is not limited thereto.
- the photocurable composition may form an organic barrier layer used for encapsulation or encapsulation of devices, in particular flexible display devices.
- the photocurable composition may be used alone as a composition for encapsulating an organic light emitting device, or may be included in the composition for encapsulating an organic light emitting device, or may be included in the composition for encapsulating an organic light emitting device together with a conventional additive.
- the photocurable composition of another embodiment of the present invention may include (A) photocurable monomer, (B) initiator, and (C) non-cyano-based silicon-containing photocurable monomer (hereinafter referred to as (C) photocurable monomer). have. (C) It is substantially the same as the photocurable composition of one Example of this invention except that it further contains a photocuring monomer.
- the photocurable monomer is a monomer that does not contain a cyano group and has a silicone and a photocurable functional group (for example, a (meth) acrylate group and a vinyl group), and is included in the photocurable composition to be reliable after curing of the photocurable composition. Can increase.
- the (C) photocuring monomer is a non-cyano-based siloxane photocuring monomer, it may be represented by the formula (3):
- R 10 , R 11 , R 12 , R 13 , R 14 , and R 15 are each independently hydrogen, a substituted or unsubstituted C1-10 alkyl group, a substituted or unsubstituted C1-10 heteroalkyl group, substituted Or an unsubstituted C 2-20 alkenyl group, a substituted or unsubstituted C 2-20 heteroalkenyl group, a substituted or unsubstituted C 6-20 aryl group, a substituted or unsubstituted C 4-20 hetero Aryl group, substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, substituted or unsubstituted silyl group having 1 to 10 carbon atoms, substituted or unsubstituted silyloxy group having 1 to 10 carbon atoms, or 4,
- R 4 is hydrogen or an alkyl group having 1-5 carbon atoms
- Z is a single bond, substituted or unsubstituted C 1-10 alkylene group, substituted or unsubstituted C 1-10 heteroalkylene group, substituted or unsubstituted C 2-20 alkenylene group, substituted or unsubstituted Heteroalkenylene group having 2 to 20 carbon atoms, substituted or unsubstituted Carbon number 6-20 Arylene group or substituted or unsubstituted carbon number A heteroaryl group, a substituted or unsubstituted alkoxy group of the ring carbon atoms 1-10) 4-20
- At least one of R 10 , R 11 , R 12 is the formula (4),
- At least one of R 13 , R 14 , and R 15 is represented by Formula 4).
- R 10 , R 11 , and R 12 may be represented by Formula 4 wherein an alkyl group having 1 to 5 carbon atoms or Z is an alkylene group having 1 to 5 carbon atoms, and at least one of R 10 , R 11 , and R 12 may have Z being carbon atoms
- Formula 1 is an alkylene group of 1-5
- R 15 is Formula 4 wherein an alkyl group of 1-5 carbon atoms or Z is an alkylene group of 1-5 carbon atoms
- R 13 , R 14 , R At least one of 15 is the formula (4) wherein Z is an alkylene group having 1-5 carbon atoms.
- the (C) photocuring monomer is 1,3-bis ((meth) acryloxyalkyl) tetraalkyldisiloxane including 1,3-bis (3- (meth) acryloxypropyl) tetramethyldisiloxane and the like.
- alkyl may be an alkyl group having 1 to 5 carbon atoms.
- the photocurable monomer is about 5 to 80% by weight, for example about 5 to 55% or about 40 to 55% or about 35 to 45% by weight, specifically about 35,36, in the solids based photocurable composition , 37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54 or 55% by weight.
- the photocurability and the adhesion of the photocurable composition are further improved, and the reliability of the device member can be improved.
- the photocurable composition comprises about 40 to 55 weight percent of (A) photocuring monomer in (A) + (B) + (C) on a solids basis, about 1 to 5 weight percent of (B) initiator, and ( C) about 40 to 55% by weight of a photocuring monomer.
- A photocuring monomer in (A) + (B) + (C) on a solids basis
- B initiator
- C about 40 to 55% by weight of a photocuring monomer.
- the photocurable composition of another embodiment of the present invention may include (A) photocurable monomer, (B) initiator and (D) non-silicone photocurable monomer (hereinafter referred to as (D) photocurable monomer). It is substantially the same as the photocurable composition of one Example of this invention except that it further contains (D) photocuring monomer.
- the photocurable monomer is a monomer having no photocurable functional groups (eg, (meth) acrylate groups and vinyl groups) without containing silicon, and is included in the photocurable composition to be reliable after curing of the photocurable composition. Can increase.
- photocurable functional groups eg, (meth) acrylate groups and vinyl groups
- the (D) photocuring monomer is a polyfunctional (meth) acrylate-based monomer, a di (meth) acrylate of a polyol having 2 to 20 carbon atoms and a tri (meth) acrylate of a polyol having 2 to 20 carbon atoms It may include one or more of tetra (meth) acrylate of polyols having 2 to 20 carbon atoms, penta (meth) acrylate of polyols having 2 to 20 carbon atoms or hexa (meth) acrylate of polyols having 2 to 20 carbon atoms. .
- the photocurable monomer is about 5 to 80% by weight, for example about 5 to 55% or about 40 to 55% or about 5 to 15% by weight, specifically about 5, in the photocurable composition on a solids basis 6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30, 31,32,33,34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54 or 55 May be included as a%. In the above range, it is possible to increase the photocurability and adhesion of the photocurable composition, and to improve reliability after curing.
- the photocurable composition comprises about 40 to 55 weight percent of (A) photocuring monomer in (A) + (B) + (D) on a solids basis, about 1 to 5 weight percent of (B) initiator, and ( D) about 40 to 55% by weight of a photocuring monomer.
- A photocuring monomer in (A) + (B) + (D) on a solids basis
- B initiator
- D about 40 to 55% by weight of a photocuring monomer.
- the photocurable composition of another embodiment of the present invention may include (A) photocurable monomer, (B) initiator, (C) photocurable monomer and (D) photocurable monomer. It is substantially the same as the photocurable composition of one embodiment of the present invention, except that it further comprises (C) a photocurable monomer and (D) a photocurable monomer.
- the photocurable composition comprises about 40 to 55 weight percent of (A) photocuring monomer in (A) + (B) + (C) + (D) and about 1 to 5 weight of initiator (B) on a solids basis %, (C) 35 to 45% by weight photocuring monomer, and (D) about 5 to 15% by weight photocuring monomer.
- A photocuring monomer in (A) + (B) + (C) + (D)
- initiator (B) on a solids basis %
- C 35 to 45% by weight photocuring monomer
- D about 5 to 15% by weight photocuring monomer.
- the organic barrier layer of the present invention may be formed with the photocurable composition of the embodiments of the present invention.
- the organic barrier layer may be formed by photocuring the photocurable composition of the embodiments of the present invention.
- the photocurable composition may be coated to a thickness of about 0.1 ⁇ m-20 ⁇ m and cured by irradiation at about 10-500 J / cm 2 for about 1-50 seconds.
- the organic barrier layer has an adhesion to the inorganic barrier layer of about 20 kgf or more, for example about 20-100 kgf, for example about 25-100 kgf. Therefore, the organic barrier layer can be used for encapsulation of the device member by forming a barrier stack together with the following inorganic barrier layer.
- the inorganic barrier layer is not particularly limited as long as the inorganic barrier layer is excellent in light transmittance and excellent in moisture and / or oxygen barrier property.
- the metal and nonmetal are silicon (Si), aluminum (Al), selenium (Se), zinc (Zn), antimony (Sb), indium (In), germanium (Ge), tin (Sn), bismuth (Bi), Transition metals, lanthanide metals, and the like, but are not limited thereto.
- the inorganic barrier layer is SiOx, SizNx, SiOxNy, ZnSe, ZnO, Sb 2 O 3 , Al 2 O 3 , In 2 O 3 , SnO 2 (wherein x is 1-5, y is 1-5 And z is 1-5).
- the 'metal' in the inorganic barrier layer may be replaced with a 'non-metal'.
- the barrier stack of the present invention may include an organic barrier layer and an inorganic barrier layer formed of the photocurable composition of the embodiments of the present invention.
- the inorganic barrier layer may be formed of an inorganic layer different from the organic barrier layer, thereby supplementing the effect of the organic barrier layer.
- the inorganic barrier layer and the organic barrier layer may be deposited by a vacuum process such as sputtering, chemical vapor deposition, metal organic chemical vapor deposition, plasma chemical vapor deposition, evaporation, sublimation, electron cyclotron resonance-plasma enhanced chemical vapor deposition, and combinations thereof.
- a vacuum process such as sputtering, chemical vapor deposition, metal organic chemical vapor deposition, plasma chemical vapor deposition, evaporation, sublimation, electron cyclotron resonance-plasma enhanced chemical vapor deposition, and combinations thereof.
- a vacuum process such as sputtering, chemical vapor deposition, metal organic chemical vapor deposition, plasma chemical vapor deposition, evaporation, sublimation, electron cyclotron resonance-plasma enhanced chemical vapor deposition, and combinations thereof.
- the barrier stack includes the organic barrier layer and the inorganic barrier layer, but the number of barrier stacks is not limited.
- the combination of barrier stacks may vary depending on the level of permeation resistance to oxygen and / or moisture and / or water vapor and / or chemicals.
- the organic barrier layer and the inorganic barrier layer may be deposited alternately. This is due to the effect on the barrier layer of the organic barrier layer produced due to the physical properties of the photocurable composition described above. As a result, the effects on the display device generated from the organic barrier layer and the inorganic barrier layer can be supplemented or enhanced.
- the organic barrier layer and the inorganic barrier layer may each be deposited in a total of about 10 layers or less, for example, about 7 layers or less (for example, 2-7 layers) in an alternating manner of about 2 or more layers.
- the barrier layer, the organic barrier layer, the inorganic barrier layer, the organic barrier layer, the inorganic barrier layer, the organic barrier layer, and the inorganic barrier layer may be formed in a seven-layer structure.
- the thickness of one organic barrier layer may be about 0.1 ⁇ m-20 ⁇ m, for example about 1 ⁇ m-20 ⁇ m, and the thickness of one inorganic barrier layer may be about 5 nm-500 nm, for example about 5 nm-200 nm. have.
- the barrier stack is a thin film encapsulant and may have a thickness of about 5 ⁇ m or less, for example about 1.5 ⁇ m-5 ⁇ m.
- An encapsulated device of the present invention includes a device member and a barrier stack formed over the device member, the barrier stack comprising an organic barrier layer and an inorganic barrier layer, wherein the organic barrier layer is comprised of the photocurable composition of embodiments of the present invention. Can be formed.
- Device members include organic light emitting diodes (OLEDs), lighting devices, flexible organic light emitting diode displays, metal sensor pads, microdisk lasers, electrochromic devices, photochromic devices, microelectromechanical systems, solar cells, integrated circuits, Charge coupling devices, light emitting polymers, light emitting diodes, and the like, but is not limited thereto.
- OLEDs organic light emitting diodes
- lighting devices flexible organic light emitting diode displays
- metal sensor pads microdisk lasers
- electrochromic devices electrochromic devices
- photochromic devices microelectromechanical systems
- solar cells integrated circuits
- Charge coupling devices Charge coupling devices, light emitting polymers, light emitting diodes, and the like, but is not limited thereto.
- the encapsulated device may be, for example, a display device, an organic light emitting display device, or the like, but is not limited thereto.
- FIG. 1 is a cross-sectional view of an encapsulated organic light emitting display device according to an embodiment of the present invention.
- an encapsulated organic light emitting diode display 100 may include a substrate 10; An organic light emitting device 20 formed on the substrate 10; And a barrier stack 30 formed on the organic light emitting element 20 and composed of an inorganic barrier layer 31 and an organic barrier layer 32, wherein the organic light emitting element 20 and the inorganic barrier layer 31 are mutually In contact, the organic barrier layer 32 may be formed from the photocurable composition of embodiments of the present invention.
- the substrate 10 is not particularly limited as long as it is a substrate on which device members can be laminated.
- it may be made of a material such as transparent glass, plastic sheet, silicon or metal substrate.
- the organic light emitting diode 20 is commonly used in an organic light emitting diode display and may include an organic light emitting film formed between the first electrode, the second electrode, and the first electrode and the second electrode. .
- the method of forming the inorganic barrier layer 31 and the organic barrier layer 32 is not limited, but vacuum processes such as sputtering, chemical vapor deposition, plasma chemical vapor deposition, evaporation, sublimation, electron cyclotron resonance-plasma vapor deposition and It can be formed by a combination thereof.
- FIG. 2 is a cross-sectional view of an encapsulated organic light emitting display device according to another embodiment of the present invention.
- an encapsulated organic light emitting diode display 200 may include a substrate 10; An organic light emitting device 20 formed on the substrate 10; And a barrier stack 30 formed on the organic light emitting element 20 and composed of an inorganic barrier layer 31 and an organic barrier layer 32, wherein the barrier stack 30 is disposed between the organic light emitting element 20 and the inorganic barrier layer 31.
- the space 40 is formed, and the organic barrier layer 32 may be formed of the photocurable composition of the embodiments of the present invention.
- the organic light emitting diode 20 and the inorganic barrier layer 31 are substantially the same as the encapsulated organic light emitting diode display of the exemplary embodiment of the present invention except that the empty space 40 is formed without contacting each other.
- Non-cyano-based silicone-containing photocuring monomer 1,3-bis (3-methacryloxypropyl) tetramethyldisiloxane
- the components (A), (B), (C) and (D) were mixed in the contents (unit: parts by weight, based on solids) described in Table 2 below, and mixed for 3 hours using a shaker to prepare a photocurable composition. It was.
- A is the ratio of the intensity of the absorption peak in the vicinity of 1635 cm -1 to the intensity of the absorption peak in the vicinity of 1720 cm -1 for the cured film
- B is the ratio of the intensity of the absorption peak near 1635 cm ⁇ 1 to the intensity of the absorption peak near 1720 cm ⁇ 1 for the composition).
- Adhesive force 1 (kgf) As a method for measuring the adhesive force between the glass and the glass, the adhesive force was measured by the same method as the method of measuring the die shear strength. The force of peeling was measured by pushing the upper glass from the side with a force of 200kgf at 25 ° C. with the dage series 4000PXY, which is an adhesive force measuring instrument. The size of the lower glass was 2 cm x 2 cm x 1 mm (width x length x thickness), and the size of the upper glass was 1.5 cm x 1.5 cm x 1 mm (width x length x thickness), and the thickness of the adhesive layer was 500 ⁇ m. It was set as.
- Adhesive force 2 (kgf): As a method for measuring the adhesion between silicon nitride and silicon nitride, the adhesive force was measured in the same manner as the method of measuring the die shear strength. The force of peeling the upper glass was pushed away from the side with a force of 200kgf at 25 ° C. with the dage series 4000PXY, an adhesive force measuring instrument. The size of the lower glass was 2 cm x 2 cm x 1 mm (width x length x thickness), and the size of the upper glass was 1.5 cm x 1.5 cm x 1 mm (width x length x thickness), and the thickness of the adhesive layer was 500 ⁇ m. It was set as. Silicon nitride is coated on the lower glass and the upper glass where the adhesive layer is located.
- the device for reliability evaluation can be manufactured by a conventional method.
- the device is deposited on the substrate and an inorganic barrier layer is formed.
- the photocurable composition is applied to a thickness of 1 ⁇ m-5 ⁇ m using methods such as spin coating and slit coating and irradiated with light to form an organic barrier layer.
- the organic barrier layer and the inorganic barrier layer are alternately formed and deposited three times in total.
- Reliability is determined by observing the time when discoloration occurs inside the package under a microscope while standing at 85 ° C. and 85% relative humidity. The reliability score is evaluated based on the discoloration occurrence time as shown in Table 1 below. Higher scores mean higher reliability.
- the photocurable composition of the present invention not only has high photocurability, but also has high adhesion to inorganic barrier layers such as silicon oxide and silicon nitride after curing, and is reliable even in harsh conditions when made into a device package. This was good.
- the compositions of Comparative Examples 1 and 2 that do not contain the cyano group-containing silicon-based photocuring monomer of the present invention has a high degree of photocurability, but the adhesion to the inorganic barrier layer is low and the reliability is not good to implement the effects of the present invention.
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Abstract
Description
변색 발생 시점 | 신뢰성 점수 |
1주 미만 | 0점 |
1주 이상 ~ 2주 미만 | 1점 |
2주 이상 ~ 3주 미만 | 2점 |
3주 이상 ~ 4주 미만 | 3점 |
4주 이상 ~ 5주 미만 | 4점 |
5주 이상 ~ 6주 미만 | 5점 |
6주 이상 ~ 7주 미만 | 6점 |
7주 이상 ~ 8주 미만 | 7점 |
8주 이상 ~ 9주 미만 | 8점 |
9주 이상 ~ 10주 미만 | 9점 |
10주 이상 | 10점 |
실시예 | 비교예 | ||||||||||||
1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 1 | 2 | ||
(A) | (A1) | 98 | 49 | 0 | 0 | 0 | 0 | 49 | 0 | 49 | 49 | 0 | 0 |
(A2) | 0 | 0 | 98 | 49 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | |
(A3) | 0 | 0 | 0 | 0 | 98 | 49 | 0 | 0 | 0 | 0 | 0 | 0 | |
(A4) | 0 | 0 | 0 | 0 | 0 | 0 | 49 | 49 | 0 | 0 | 0 | 0 | |
(C) | 0 | 49 | 0 | 49 | 0 | 49 | 0 | 49 | 0 | 39 | 49 | 0 | |
(D) | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 49 | 10 | 49 | 98 | |
(B) | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | |
광경화 조건 | 100 J/cm2, 10 sec | ||||||||||||
광경화도 (%) | 94.0 | 94.0 | 94.2 | 94.1 | 94.3 | 94.2 | 94.3 | 94.1 | 93.9 | 94.0 | 94.0 | 94.0 | |
부착력 1(kgf) | 47.8 | 34.2 | 42.1 | 31.8 | 52.7 | 44.9 | 30.6 | 27.5 | 29.7 | 30.2 | 17.3 | 15.2 | |
부착력 2 (kgf) | 45.4 | 31.6 | 40.9 | 31.0 | 44.8 | 40.1 | 28.0 | 25.4 | 26.3 | 27.9 | 15.1 | 12.4 | |
신뢰성 | 10점 | 9점 | 10점 | 9점 | 10점 | 10점 | 8점 | 7점 | 8점 | 8점 | 4점 | 3점 |
Claims (15)
- 하기 화학식 1로 표시되는 (A)시아노기 함유 실리콘계 광경화 모노머, 및 (B)개시제를 포함하는 광경화 조성물:<화학식 1>(상기 화학식 1에서,R1 및 R2는 각각 독립적으로, 수소, 치환 또는 비치환된 탄소수 1-10의 알킬기, 치환 또는 비치환된 탄소수 2-10의 헤테로알킬기, 치환 또는 비치환된 탄소수 6-20의 아릴기, 치환 또는 비치환된 탄소수 4-20의 헤테로아릴기, 치환 또는 비치환된 탄소수 7-21의 아릴알킬기, 치환 또는 비치환된 탄소수 1-10의 실릴기 또는 하기 화학식 2이고,<화학식 2>(상기 화학식 2에서,*는 원소의 연결 부위이고, R4는 수소 또는 탄소수 1-5의 알킬기이다)R1 및 R2 중 적어도 하나는 상기 화학식 2이고,R3은 수소, 수산기, 할로겐, -NR'R"(R', R"은 각각 독립적으로 수소, 치환 또는 비치환된 탄소수 1-10의 알킬기, 치환 또는 비치환된 탄소수 2-10의 헤테로알킬기, 치환 또는 비치환된 탄소수 6-20의 아릴기, 치환 또는 비치환된 탄소수 4-20의 헤테로아릴기, 또는 치환 또는 비치환된 탄소수 7-21의 아릴알킬기이다), 치환 또는 비치환된 탄소수 1-10의 알킬기, 치환 또는 비치환된 탄소수 2-10의 헤테로알킬기, 치환 또는 비치환된 탄소수 6-20의 아릴기, 치환 또는 비치환된 탄소수 4-20의 헤테로아릴기, 치환 또는 비치환된 탄소수 7-21의 아릴알킬기, 또는 치환 또는 비치환된 탄소수 1-10의 실릴기이고,X1, X2는 각각 독립적으로 단일결합 또는 산소이고,X3, Y1 및 Y2는 각각 독립적으로, 치환 또는 비치환된 탄소수 1-10의 알킬렌기, 치환 또는 비치환된 탄소수 2-10의 헤테로알킬렌기, 치환 또는 비치환된 탄소수 6-20의 아릴렌기, 치환 또는 비치환된 탄소수 7-21의 아릴알킬렌기, 치환 또는 비치환된 탄소수 4-20의 헤테로아릴렌기, 또는 치환 또는 비치환된 탄소수 3-10의 시클로알킬렌기이다).
- 제1항에 있어서, 상기 (A)시아노기 함유 실리콘계 광경화 모노머는 단독 또는 2종 이상으로 포함되는 광경화 조성물.
- 제2항에 있어서, 상기 광경화 조성물은 모노(메트)아크릴레이트형의 상기 (A)시아노기 함유 실리콘계 광경화 모노머와 디(메트)아크릴레이트형의 상기 (A) 시아노기 함유 실리콘계 광경화 모노머의 혼합물을 포함하는 광경화 조성물.
- 제1항에 있어서, 상기 조성물은 (C)비-시아노계 실리콘 함유 광경화 모노머, (D)비-실리콘계 광경화 모노머 중 하나 이상을 더 포함하는 광경화 조성물.
- 제4항에 있어서, 상기 (C)비-시아노계 실리콘 함유 광경화 모노머는 하기 화학식 3으로 표시되는 광경화 조성물:<화학식 3>(상기 화학식 3에서,R10,R11,R12,R13,R14,R15은 각각 독립적으로, 수소, 치환 또는 비치환된 탄소수 1-10의 알킬기, 치환 또는 비치환된 탄소수 1-10의 헤테로알킬기, 치환 또는 비치환된 탄소수 2-20의 알케닐기, 치환 또는 비치환된 탄소수 2-20의 헤테로알케닐기, 치환 또는 비치환된 탄소수 6-20의 아릴기, 치환 또는 비치환된 탄소수 4-20의 헤테로아릴기, 치환 또는 비치환된 탄소수 1-10의 알콕시기, 치환 또는 비치환된 탄소수 1-10의 실릴기, 치환 또는 비치환된 탄소수 1-10의 실릴옥시기, 또는 하기 화학식 4이고,<화학식 4>(상기 화학식 4에서,*는 상기 화학식 3 중 Si에 대한 연결 부위이고,R4는 수소, 또는 탄소수 1-5의 알킬기이고,Z는 단일결합, 치환 또는 비치환된 탄소수 1-10의 알킬렌기, 치환 또는 비치환된 탄소수 1-10의 헤테로알킬렌기, 치환 또는 비치환된 탄소수 2-20의 알케닐렌기, 치환 또는 비치환된 탄소수 2-20의 헤테로알케닐렌기, 치환 또는 비치환된 탄소수 6-20의 아릴렌기, 또는 치환 또는 비치환된 탄소수 4-20의 헤테로아릴렌기, 치환 또는 비치환된 탄소수 1-10의 알콕시렌기이다)R10, R11, R12 중 적어도 하나는 상기 화학식 4이고,R13, R14, R15 중 적어도 하나는 상기 화학식 4이다).
- 제4항에 있어서, 상기 (D)비-실리콘계 광경화 모노머는 탄소수 2-20의 폴리올의 디(메트)아크릴레이트, 탄소수 2-20의 폴리올의 트리(메트)아크릴레이트, 탄소수 2-20의 폴리올의 테트라(메트)아크릴레이트, 탄소수 2-20의 폴리올의 펜타(메트)아크릴레이트, 탄소수 2-20의 폴리올의 헥사(메트)아크릴레이트 중 하나 이상을 포함하는 광경화 조성물.
- 제1항에 있어서, 상기 조성물은 고형분 기준 (A)+(B) 중 상기 (A)광경화 모노머 약 1-99중량% 및 상기 (B)개시제 약 1-99중량%를 포함하는 광경화 조성물.
- 제4항에 있어서, 상기 조성물은 고형분 기준 (A)+(B)+(C) 중 상기 (A)광경화 모노머 약 40-55중량%, 상기 (B)개시제 약 1-5중량%, 상기 (C)광경화 모노머 약 40-55중량%를 포함하는 광경화 조성물.
- 제4항에 있어서, 상기 조성물은 고형분 기준 (A)+(B)+(D) 중 상기 (A)광경화 모노머 약 40-55중량%, 상기 (B)개시제 약 1-5중량%, 상기 (D)광경화 모노머 약 40-55중량%를 포함하는 광경화 조성물.
- 제4항에 있어서, 상기 조성물은 고형분 기준 (A)+(B)+(C)+(D) 중 상기 (A)광경화 모노머 약 40-55중량%, 상기 (B)개시제 약 1-5중량%, 상기 (C)광경화 모노머 약 35-45중량%, 및 상기 (D)광경화 모노머 약 5-15중량%를 포함하는 광경화 조성물.
- 제1항 내지 제11항 중 어느 한 항의 광경화 조성물을 포함하는 유기발광소자 봉지용 조성물.
- 장치용 부재; 및상기 장치용 부재 위에 형성되고, 무기 장벽층과 제1항 내지 제11항 중 어느 한 항의 광경화 조성물로 형성되는 유기 장벽층을 포함하는 장벽 스택(barrier stack)을 포함하는, 봉지화된 장치.
- 제13항에 있어서, 상기 무기 장벽층은 금속, 비금속, 금속 또는 비금속간의 화합물 또는 합금, 금속 또는 비금속의 산화물, 금속 또는 비금속의 불화물, 금속 또는 비금속의 질화물, 금속 또는 비금속의 탄화물, 금속 또는 비금속의 산소질화물, 금속 또는 비금속의 붕소화물, 금속 또는 비금속의 산소붕소화물, 금속 또는 비금속의 실리사이드 또는 이들의 혼합물을 포함하고, 상기 금속, 비금속은 실리콘(Si), 알루미늄(Al), 셀레늄(Se), 아연(Zn), 안티몬(Sb), 인듐(In), 게르마늄(Ge), 주석(Sn), 비스무트(Bi), 전이금속, 란탄족 금속 중 하나 이상을 포함하는 봉지화된 장치.
- 제13항에 있어서, 상기 장치용 부재는 플렉시블(flexible) 유기발광소자, 유기발광소자, 조명 장치, 금속 센서 패드, 마이크로디스크 레이저, 전기변색 장치, 광변색장치, 마이크로전자기계 시스템, 태양전지, 집적 회로, 전하 결합 장치, 발광 중합체 또는 발광 다이오드인 봉지화된 장치.
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