WO2014073895A1 - Composite, composition le contenant et appareil - Google Patents

Composite, composition le contenant et appareil Download PDF

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Publication number
WO2014073895A1
WO2014073895A1 PCT/KR2013/010094 KR2013010094W WO2014073895A1 WO 2014073895 A1 WO2014073895 A1 WO 2014073895A1 KR 2013010094 W KR2013010094 W KR 2013010094W WO 2014073895 A1 WO2014073895 A1 WO 2014073895A1
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Prior art keywords
wax
composite
based compound
quantum
quantum dot
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PCT/KR2013/010094
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English (en)
Korean (ko)
Inventor
권두효
최정옥
권오관
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주식회사 엘엠에스
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Priority claimed from KR1020130079501A external-priority patent/KR101396871B1/ko
Application filed by 주식회사 엘엠에스 filed Critical 주식회사 엘엠에스
Priority to US14/442,083 priority Critical patent/US20160068749A1/en
Publication of WO2014073895A1 publication Critical patent/WO2014073895A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
    • C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/88—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing selenium, tellurium or unspecified chalcogen elements
    • C09K11/881—Chalcogenides
    • C09K11/883—Chalcogenides with zinc or cadmium

Definitions

  • the present invention relates to a composite, a composition and a device comprising the same, and a composite, a composition and a device comprising the improved dispersibility and luminescent properties.
  • Quantum dots are materials with crystal structures ranging in size from tens to tens of nanometers and consist of hundreds to thousands of atoms. Quantum dots are very small in size, resulting in quantum confinement effects.
  • the quantum confinement effect refers to a phenomenon in which a band gap of the object becomes large when the object becomes smaller than the nano size.
  • the quantum dots are excited by absorbing the light and falling to the ground state while emitting light of a specific wavelength.
  • the wavelength of the emitted light has a value corresponding to the band gap. Since quantum dots have different light emission characteristics due to quantum confinement effects, they are used in various light emitting devices and electronic devices by controlling them.
  • the quantum dots when a plurality of quantum dots are dispersed in a solvent or a resin, the quantum dots may be easily aggregated with each other, thereby decreasing quantum efficiency.
  • the quantum dots made of metal are very vulnerable to moisture, so that the quantum efficiency may be lowered by being easily oxidized by moisture in the air.
  • the quantum dot has a problem in that it is difficult to store because it has low dispersibility in a solvent or resin and low stability in moisture, heat or light.
  • the quantum dots may be easily damaged as the use time of the light emitting device increases because the quantum dots themselves have low stability against moisture, heat, or light. That is, there is a problem in that the lifetime of the light emitting device is shortened by applying the quantum dots to the light emitting device.
  • One object of the present invention is to provide a composite with improved dispersibility and stability against heat, light and moisture as well as quantum efficiency.
  • Another object of the present invention is to provide a composition comprising the complex.
  • Another object of the present invention is to provide a device comprising a coating layer or a film made of the composition.
  • the composite according to an embodiment of the present invention includes at least one quantum dot and a wax-based compound covering the surface of the quantum dot.
  • the wax-based compound may encapsulate the quantum dots.
  • the wax-based compound may encapsulate one quantum dot.
  • the two or more quantum dots may be spaced apart from each other in the aggregate formed by the wax-based compound, so that the quantum dots may be encapsulated by the wax-based compound.
  • the molecular weight of the wax-based compound may be 1,000 or more and 20,000 or less.
  • the melting point of the wax-based compound may be at least 80 °C 200 °C.
  • the wax-based compound may include a polyethylene-based wax, a polypropylene-based wax or an amide-based wax.
  • the acid value of the wax-based compound may be 1 mg KOH / g to 200 mg KOH / g.
  • the density of the wax-based compound may be 0.95 g / cm 3 or more.
  • composition according to the embodiment of the present invention includes a solvent and a complex.
  • the composite includes a wax-based compound dispersed in the solvent and covering at least one quantum dot and the quantum dot.
  • a composition according to another embodiment of the present invention includes a resin and a composite.
  • the composite includes a wax-based compound dispersed in the resin and covering at least one quantum dot and the quantum dot.
  • the resin may include a silicone resin, an epoxy resin, or an acrylic resin.
  • Coating layer or film according to an embodiment of the present invention is prepared using the composition.
  • the complexes may be uniformly dispersed in a solvent or a resin without aggregation with each other.
  • the composite can be maintained in a uniform dispersed state for a long time.
  • the wax-based compound protects the quantum dots, thereby preventing damage to the quantum dots due to moisture, light, heat, and the like, thereby improving stability of the composite with respect to the surrounding environment such as temperature, humidity, and ultraviolet rays.
  • the wax-based compound may constitute one complex such that each of the wax-based compounds may be encapsulated without being aggregated with each other.
  • the composite having improved quantum efficiency than the respective quantum dots can be manufactured and used in various fields.
  • the composites according to the present invention in a light emitting device or an electronic device, it is possible to prevent the lifespan from being reduced while improving color reproducibility, color rendering index, and the like.
  • FIG. 1A and 1B are conceptual views illustrating a composite according to an embodiment of the present invention.
  • Figure 1c is a conceptual diagram for explaining the composite according to another embodiment of the present invention.
  • Figure 2 is a flow chart for explaining a method for producing a composite and a composition comprising the same according to an embodiment of the present invention.
  • 3 to 5 are cross-sectional views illustrating an apparatus according to another embodiment of the present invention.
  • first and second may be used to describe various components, but the components should not be limited by the terms. The terms are used only for the purpose of distinguishing one component from another.
  • the first component may be referred to as the second component, and similarly, the second component may also be referred to as the first component.
  • FIG. 1A and 1B are conceptual views illustrating a composite according to an embodiment of the present invention.
  • the composite 101 includes a quantum dot 111 and a wax-based compound 130.
  • the "wax-based compound” is defined as a compound having a melting point (Melting point) higher than the room temperature in the solid state at room temperature. That is, in this specification, unless otherwise specified, “wax” refers to a solid state.
  • “Room temperature” is defined as about 15 ° C to about 25 ° C. Melting point of the wax-based compound 130 may be about 80 °C to about 200 °C.
  • FIG. 1A and FIG. 1B two quantum dots 111 are illustrated to describe the relationship between adjacent quantum dots. However, since the two quantum dots 111 are substantially the same, one quantum dot will be described and overlapping descriptions will be omitted. do.
  • the quantum dot 111 is a particle having a crystal structure of several to several tens of nanometers in size, and is composed of hundreds to thousands of atoms. Since the size of the quantum dot 111 is a nano size, a quantum confinement effect appears in the quantum dot 111.
  • the quantum confinement effect refers to a phenomenon in which the band gap of the particle is discontinuously quantized when the particle size is several tens of nanometers or less. The smaller the particle size, the larger the band gap.
  • the quantum dot 111 absorbs the incident light into an excited state, and the quantum dot in the excited state is based It falls to the ground state and emits light of a specific wavelength corresponding to the band gap.
  • the band gap of the quantum dot 111 may be adjusted through the size, composition, etc. of the quantum dot 111 itself.
  • the structure of the quantum dot 111 is not particularly limited.
  • the quantum dot 111 may be a single structure consisting of only a core, a core-single shell structure consisting of a core and a single layer shell, or a core-multishell shell structure consisting of a core and a multilayer shell.
  • the material forming the core or the shell include II-VI compound semiconductor nanocrystals such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, HgS, HgSe, HgTe, GaN, GaP, GaAs, InP, InAs, etc.
  • Group III-V compound semiconductor nanocrystal or a mixture thereof is mentioned.
  • the quantum dot 111 may have a CdSe / ZnS (core / shell) structure having a core including CdSe and a shell including ZnS.
  • the quantum dot 111 may have an InP / ZnS (core / shell) structure having a core including InP and a shell including ZnS.
  • the quantum dot 111 may further include a ligand (SC) bonded to the surface of the central particle made of the above-described compounds.
  • the ligand SC may prevent quantum dots 111 adjacent to each other from being aggregated and quenched.
  • the ligand (SC) may include a hydrophobic compound.
  • the amine compound which has a C6-C30 alkyl group or an alkenyl group, the carboxylic acid compound which has a C6-C30 alkyl group or an alkenyl group, etc. are mentioned.
  • the quantum dot 111 illustrated in FIG. 1A may include the ligand SC.
  • the wax-based compound 130 covers the quantum dot 111.
  • the wax-based compound 130 may encapsulate the quantum dot 111 by covering the surface of the quantum dot 111 as a whole. In this case, the wax-based compound 130 may form a capsule layer having a predetermined thickness on the surface of the quantum dot 111.
  • the quantum dot 111 may be prevented from being damaged by moisture, heat, light, or the like caused by an external environment.
  • the molecular weight (MW) of the wax-based compound 130 may be about 1,000 to 20,000.
  • the said molecular weight is a number average molecular weight converted into polystyrene.
  • the wax-based compound 130 cannot encapsulate the quantum dots 111 because the wax-based compound 130 may not have a property of a wax present in a solid state at room temperature. It is difficult.
  • the size (average diameter) of the recrystallization of the wax-based compound 130 is several hundred ⁇ m or more, so that even if a composite is prepared using the solvent or There is a problem that is difficult to disperse in the resin.
  • the wax-based compound 130 may be in a liquid phase at a temperature exceeding about 200 °C in the process of encapsulating the quantum dot 111 The quantum dot 111 may be damaged.
  • Synthetic wax may be used as the wax-based compound 130.
  • the wax-based compound 130 may be a polymer, a copolymer or an oligomer.
  • the wax-based compound 130 may include a polyethylene-based wax, a polypropylene-based wax, or an amide-based wax.
  • the wax compound 130 may include at least one of units represented by the following Chemical Formulas 1 to 7.
  • R 1 , R 3 , R 5, and R 7 each independently represent a single bond or an alkylene group having 1 to 10 carbon atoms (*-(CH 2 )).
  • x- *, x represents an integer of 1 to 10
  • R 2 , R 4 , R 6 and R 8 each independently represent hydrogen or an alkyl group having 1 to 10 carbon atoms
  • R a , R b , R c , R d , R e , R f and R g each independently represent hydrogen or an alkyl group having 1 to 3 carbon atoms.
  • R 2 of Formula 1 when R 2 of Formula 1 includes hydrogen, the unit of Formula 1 includes a carboxyl group.
  • R 2 in Formula 1 represents an alkyl group having 1 to 10 carbon atoms, the unit of Formula 1 includes an ester group.
  • R 4 of Formula 2 includes hydrogen
  • the unit of Formula 2 includes an aldehyde group.
  • R 4 in Formula 2 represents an alkyl group having 1 to 10 carbon atoms
  • the unit of Formula 2 includes a ketone group.
  • R 6 of Formula 3 When R 6 of Formula 3 includes hydrogen, the unit of Formula 3 includes a hydroxy group. On the contrary, when R 6 in Formula 3 represents an alkyl group having 1 to 10 carbon atoms, the unit of Formula 3 includes an ether group.
  • the polyethylene wax may be defined.
  • the polyethylene wax includes a polyethylene wax (PE wax) including only a unit in which R g of Formula 7 is hydrogen.
  • the polyethylene wax is selected from units in which R g of Formula 7 is hydrogen, and units in which R a , R b , R c , R d , R e and R f of Formulas 1 to 6 are hydrogen. At least one oxygen-containing unit may be included at the same time.
  • polyethylene wax containing at least one oxygen-containing unit examples include oxidized polyethylene wax (PE wax), an ethylene-acrylic acid copolymer, and ethylene-vinyl acetate, which are oxides of polyethylene.
  • PE wax oxidized polyethylene wax
  • ethylene-acrylic acid copolymer an ethylene-acrylic acid copolymer
  • ethylene-vinyl acetate which are oxides of polyethylene.
  • Ethylene-vinyl acetate copolymer Ethylene-maleic anhydride copolymer etc. are mentioned.
  • the polypropylene wax may be defined. have.
  • the polypropylene wax includes a polypropylene wax (PP wax) including only a unit in which R g of Formula 7 is a methyl group.
  • the polypropylene wax is a unit in which R g of Formula 7 is a methyl group, and units of R a , R b , R c , R d , R e and R f of Formulas 1 to 6 are hydrogen.
  • At least one oxygen-containing unit selected may be included at the same time.
  • a propylene-maleic anhydride copolymer etc. are mentioned.
  • the amide wax has a main chain including an amide bond (-CONH-). That is, the amide wax may be a polymer, copolymer or oligomer including a unit containing an amide bond.
  • the unit of the amide wax may have 1 to 10 carbon atoms.
  • the amide wax may further include one or more kinds of oxygen-containing units represented by Formulas 1 to 6.
  • the quantum dot 111 may be stably compared with the case where only the unit represented by Chemical Formula 7 is included. It can be encapsulated. That is, the PE wax or the PP wax encapsulates the surface of the quantum dot 111 at random, while the wax-based compound 130 and the quantum dot 111 are formed by the polarity of oxygen included in the oxygen-containing unit. The interaction with the metal constituting the is strong. Therefore, when the wax-based compound 130 includes at least one oxygen-containing unit among the units represented by Chemical Formulas 1 to 6, the wax-based compound 130 may stably encapsulate the quantum dots 111. have.
  • the unit represented by Chemical Formula 1, particularly a carboxyl group is most advantageous for encapsulating the quantum dots 111 because the wax-based compound 130 has a strong interaction with the quantum dots 111. Therefore, the wax compound 130 according to the present invention preferably includes at least a carboxy group as a substituent.
  • the wax-based compound 130 including at least one oxygen-containing unit of the units represented by Formulas 1 to 6 may encapsulate a maximum amount of the quantum dots 111. That is, when the amount of the quantum dot 111 added to the solution in which PE wax, PP wax or the like is dissolved is "1" and the amount of the encapsulated quantum dot 111 is "A", "A" is not 0. It can have a value greater than 1 and less than 1.
  • An oxygen-containing wax-based compound which is a wax-based compound 130 including oxygen-containing units represented by Chemical Formulas 1 to 6, may be prepared by oxidizing polyethylene or polypropylene as a base material.
  • the oxygen-containing wax-based compound may be prepared by polymerizing single monomers or copolymerizing two or more different monomers.
  • the recrystallization formed when the PE wax containing ethylene as a unit is recrystallized, it can be easily used without difficulty in encapsulating the quantum dots 111, but the wax-based compound 130 In consideration of the interaction between the quantum dot 111 and the oxygen-based PE wax, the quantum dot 111 can be encapsulated relatively more stably than the PE wax.
  • the wax-based compound 130 may have an acid value of about 1 mg KOH / g to about 200 mg KOH / g.
  • the "acid value" of the wax-based compound 130 refers to the number of mg of potassium hydroxide (KOH) required to neutralize 1 g of the wax-based compound 130.
  • the wax-based compound 130 may have an acid value of about 1 mg KOH / g or more. That is, the larger the acid value, the more carboxyl groups included in the wax-based compound 130.
  • the acid value of the wax-based compound 130 is less than about 1 mg KOH / g, the amount of the carboxyl group interacting with the quantum dot 111 is very small, so that the wax-based compound 130 and the quantum dot ( 111) the interactions between them are almost the same as with PE wax or PP wax.
  • the acid value of the wax-based compound 130 exceeds about 200 mg KOH / g, the ligand (SC) rather than by the carboxy group may be deteriorated to oxidize the surface of the quantum dot (111). Even if the quantum dot 111 is encapsulated due to oxidation of the quantum dot 111, a problem occurs that quantum efficiency is lowered.
  • the wax-based compound 130 preferably has an acid value of about 1 mg KOH / g to about 200 mg KOH / g. More preferably, the wax-based compound 130 may have an acid value of about 5 mg KOH / g to about 50 mg KOH / g.
  • the acid value of the wax-based compound 130 may be measured according to the ASTM 1386 standard. For example, after quantifying about 2 g of the wax-based compound 130 as a sample, the mixture is put into a Erlenmeyer flask, and 40 ml of xylene is heated to raise the temperature. When the sample becomes a completely colorless transparent solution, 2-3 drops of phenolphthalein solution are added.
  • the acid value can be calculated by adding a titration with a KOH solution of about 0.1 N and maintaining the color of the solution for about 10 seconds.
  • the acid value may be calculated by the following Equation 1.
  • Equation 1 "A” represents the amount of KOH (unit: ml) used for sample titration, "N” represents the normal concentration of KOH (unit: N), and "B” represents the amount of sample (unit) : g) is shown.
  • the wax-based compound 130 may have a high density of about 0.95 g / cm 3 or more.
  • the melting point of the composite 101 including the wax-based compound 130 is higher than that of the low-density wax having a low density of less than about 0.95 g / cm 3 . Heat resistance can be improved.
  • the wax-based compound 130 has a high density, since the crystallinity of recrystallization of the wax-based compound 130 is superior to that of the low-density wax, the quantum dot 111 may be stably encapsulated.
  • PE wax may be classified into high density PE wax (HDPE wax) and low density PE wax (LDPE wax) according to the above criteria. That is, HDPE wax has a density of at least about 0.95 g / cm 3 . In this case, the density of the HDPE wax may be about 1.20 g / cm 3 or less.
  • the HDPE wax may have a melting point of about 120 ° C. to about 200 ° C.
  • LDPE wax may have a density of less than about 0.95 g / cm 3 .
  • the melting point of the LDPE wax may be about 80 ° C to about 110 ° C. Therefore, when using the PE wax as the wax-based compound 130, encapsulating the quantum dots 111 with HDPE wax rather than LDPE wax can encapsulate the quantum dots 111 more uniformly.
  • the content of the units represented by Formulas 1 to 7 included in the wax-based compound 130 may vary depending on the molecular weight of the wax-based compound 130 and the acid value of the wax-based compound 130.
  • the diameter d1 of the composite 101 may be about 10 nm to 50 nm.
  • the diameter d1 of the composite 101 is a value measured by a dynamic light scattering method (DLS method) calculated by a Stokes-Einstein equation for a diffusion coefficient (hydrodynamic diameter).
  • DLS method dynamic light scattering method
  • Figure 1c is a conceptual diagram for explaining the composite according to another embodiment of the present invention.
  • the composite 102 includes at least two or more quantum dots 112 and 114 and a wax-based compound 130.
  • the quantum dots 112 and 114 included in the complex 102 are described for convenience by referring to reference numeral 112 as a “first quantum dot” and referring to reference numeral 114 as a “second quantum dot”. Since each of the first and second quantum dots 112 and 114 is substantially the same as the quantum dot 111 described with reference to FIGS. 1A and 1B, detailed descriptions thereof will be omitted.
  • the wax-based compound 130 may cover the first and second quantum dots 112 and 114 to prevent the first and second quantum dots 112 and 114 from aggregation with each other. That is, the wax-based compound 130 may make one aggregate so that the first and second quantum dots 112 and 114 may be encapsulated without being aggregated with each other.
  • the aggregate may be defined as one "composite 102". In the composite 102, the first and second quantum dots 112 and 114 are disposed in an aggregate formed by the wax-based compound 130. The number of quantum dots disposed in the aggregate may be several tens to tens of millions.
  • the diameter (d2) of the composite (102) may be about 5 nm to about 50 ⁇ m, and the diameter (d2) of the composite (102) is about 0.5 in view of the dispersibility for the resin described below. ⁇ m to about 10 ⁇ m.
  • the diameter d2 of the composite 102 may vary depending on the recrystallization rate (cooling rate) in the process of manufacturing the composite 102.
  • wax-based compound 130 is substantially the same as the wax-based compound described with reference to FIGS. 1A and 1B, detailed descriptions thereof will be omitted.
  • the composite 101 described with reference to FIGS. 1A and 1B may be formed, or the complex 102 described with reference to FIG. 1C may be formed.
  • the composite 101 described with reference to FIGS. 1A and 1B and the composite 102 described with reference to FIG. 1C may be simultaneously manufactured.
  • FIG. 2 is a flowchart illustrating a method of manufacturing a composite according to an embodiment of the present invention.
  • the wax powder is added to the organic solvent (step S210).
  • the organic solvent may include toluene.
  • the wax powder is a solid made of a wax-based compound, and the wax-based compound constituting the wax powder is substantially the same as that described in FIGS. 1A to 1C, and thus detailed descriptions thereof will be omitted.
  • solid wax pellets may be added to the organic solvent.
  • step S220 the wax powder is dissolved.
  • the wax powder or the wax pellet can be dissolved by heating the organic solvent.
  • the organic solvent is heated to a temperature above the melting point of the wax powder.
  • the organic solvent may be heated to about 200 °C to 220 °C. Accordingly, it is possible to prepare a wax solution in which the wax powder is dissolved in the organic solvent.
  • the quantum dots are mixed in the wax solution (step S230).
  • the quantum dots When the quantum dots are mixed with the wax solution, the quantum dots are dispersed in the wax solution. In this case, the ligands of the quantum dots may be easily dispersed in the wax solution without aggregation with each other. Since the quantum dots are substantially the same as the quantum dots described with reference to FIGS. 1A to 1C, detailed descriptions thereof will not be repeated.
  • step S240 the wax solution in which the quantum dots are dispersed is cooled.
  • the dissolved wax compound may be recrystallized.
  • the wax solution in which the quantum dots are dispersed may be slowly cooled to room temperature and cooled or quenched to control the recrystallization rate (cooling rate).
  • the recrystallization rate is high, that is, when the temperature of the wax solution is drastically lowered, the size of the aggregate formed by the wax-based compound may be reduced.
  • the temperature of the wax solution is gradually lowered, the size of the aggregate can be increased.
  • Recrystallized wax-based compound can encapsulate quantum dots.
  • the wax-based compound can encapsulate one quantum dot to form a composite 101, as described in Figure 1c
  • Multiple quantum dots can be encapsulated to form a composite 102.
  • composites 101 and 102 according to the present invention can be manufactured.
  • Composites 101 and 102 according to the present invention described above may be stored and used in powder form by removing the organic solvent.
  • the complexes 101 and 102 may be stored and used in a dispersed state in the organic solvent.
  • the composites 101 and 102 may be stably stored and used by the wax-based compound 130 encapsulating the quantum dots 111, 112 and 114 in a powder form with little effect on moisture.
  • the organic solvent may be uniformly dispersed and stored in the organic solvent without aggregation of the composites 101 and 102.
  • the composition comprising the composites 101 and 102 may include a resin.
  • the resin may itself be a liquid phase.
  • the resin may be dissolved in a solvent even if the resin itself is a solid phase, and the composites 101 and 102 may be dispersed in a solution containing the resin and the solvent.
  • the composition including the resin may include at least one of the composite 101 illustrated in FIGS. 1A and 1B and the composite 102 illustrated in FIG. 1C.
  • Specific examples of the resin include vinyl siloxane resins, epoxy siloxane resins, polydimethylsiloxane (PDMS), thermoplastic silicone vulcanizate (TPSiV), thermoplastic silicone polycarbonate-urethane (TSPCU), and the like.
  • the composition may further include a crosslinking agent, a catalyst, an initiator, and the like together with the resin.
  • the composition is about 0.001 to 10 parts by weight of the composite (101, 102) and about 5 parts by weight to about 60 parts by weight of hydride siloxane as the crosslinking agent based on 100 parts by weight of the vinyl siloxane compound as a resin. , About 0.01 parts by weight to about 0.5 parts by weight of the platinum catalyst.
  • the composition comprising the complexes 101 and 102 may include at least one monomer and an initiator.
  • the monomer may include an acrylate compound, an epoxy compound, a siloxane compound, or the like. These may be used alone or in combination of two or more, respectively.
  • the composition may include at least one of the composite 101 shown in FIGS. 1A and 1B and the complex 102 shown in FIG. 1C.
  • the monomers may be polymerized to form a cured product, and the composites 101 and 102 may be dispersed in the cured product.
  • the present invention provides a coating layer or film formed of the composition.
  • the coating layer or film may be formed by crosslinking the resin of the composition or by drying the composition.
  • the composition may be cured using light or heat, and ultraviolet rays may be used when photocuring.
  • the coating layer or film may be formed by polymerizing monomers of the composition.
  • the method for forming the coating layer or film is not particularly limited.
  • the coating layer or the film may have a form in which the composites 101 and 102 are dispersed in a matrix structure formed by the resin.
  • the present invention also provides a device comprising the coating layer or film.
  • the range of the device is not particularly limited, and may be, for example, a lighting device or a display device.
  • the composite The fields 101 and 102 may be uniformly dispersed in a solvent or a resin without aggregation with each other.
  • the composites 101 and 102 may be maintained in a uniform dispersed state for a long time.
  • the wax-based compound 130 protects the quantum dots (111, 112, 114) to prevent damage to the quantum dots due to moisture, light, heat, etc., so that the stability of the composite (101, 102) to the surrounding environment Can improve.
  • the wax-based compound 130 may constitute one composite 101 and 102 such that each of the quantum dots 111 may be encapsulated without being aggregated with each other. Accordingly, the composite having improved quantum efficiency than the respective quantum dots can be manufactured and used in various fields.
  • the wax compound After mixing 20 mg of the wax compound in 1 ml of toluene, the wax compound was dissolved by raising the temperature to about 130 ° C. to prepare a wax solution.
  • the wax solution was mixed with a solution of Nanodot-HE-606 (trade name, QD solution, Korea), which was about 20 mg of CdSe-based red quantum dots in 1 ml of toluene, was cooled to room temperature. Then, after removing toluene using an evaporator, a composite according to Example 1 of the present invention in a powder state was prepared.
  • Nanodot-HE-606 trade name, QD solution, Korea
  • Licowax PED 136 wax (trade name, Clariant, Switzerland) having an acid value of about 50 mg KOH / g was used as an oxidized high density polyethylene wax (Oxidized HDPE Wax).
  • Example 2 of the present invention was prepared in substantially the same manner as the composite was prepared in Example 1.
  • Licowax PED 191 wax (trade name, Clariant, Switzerland) was used as Oxidized High Density Polyethylene Wax (Oxidized HDPE Wax) having an Acid value of about 7 mg KOH / g.
  • Example 3 of the present invention was prepared in substantially the same manner as the composite was prepared in Example 1.
  • L-C 301E wax (trade name, Lion Chemtech Co., Korea) was used as an oxidized low density polyethylene wax (Oxidized LDPE Wax) having an acid value of about 16 mg KOH / g.
  • Example 4 of the present invention was prepared in substantially the same manner as the composite was prepared in Example 1.
  • Escor TM 5000 ExCo wax (trade name, ExxonMobil Chemical, USA) is an ethylene acrylic acid copolymer having an acid value of about 75 mg KOH / g (Ethylene-Acrylic Acid Copolymer). was used.
  • Example 5 of the present invention was prepared in substantially the same manner as the composite was prepared in Example 1.
  • an EVATANE 18-150 wax (trade name, ARKEMA, France), which was an ethylene vinyl acetate copolymer, was used.
  • the composite according to Example 6 of the present invention was prepared in substantially the same manner as the composite according to Example 1.
  • Licomont AR 504 wax (trade name, Clariant, Switzerland) is a polypropylene wax having an acid value of about 40 mg KOH / g to about 45 mg KOH / g. ) was used.
  • the composite according to Example 7 was prepared in substantially the same manner as the composite according to Example 1 was prepared.
  • LC 104N wax Non-Oxidized HDPE Wax
  • having an acid value of 0 mg KOH / g (trade name, Lion Chemtech Co., Korea) was used. .
  • the composite according to Example 8 was prepared in substantially the same manner as the composite according to Example 1.
  • Escor TM 5100 ExCo wax (trade name, ExxonMobil Chemical, USA) is an ethylene acrylic acid copolymer having an acid value of about 180 mg KOH / g. Was used.
  • Nanodot-HE-606 (trade name, QD solution, Korea), which is a CdSe-based red quantum dot, was prepared.
  • Measurement samples 1 to 8 were prepared by mixing toluene with each of the composites according to Examples 1 to 8 of the present invention.
  • the quantum efficiency (Quantum Yield, QY) and the emission wavelength of the composite according to Example 1 of the present invention were measured using C9920-02 (trade name, HAMAMATSU, Japan) as an absolute quantum efficiency meter. .
  • Comparative Sample 1 was prepared by mixing quantum dots according to Comparative Example 1 with toluene. Quantum efficiency and emission wavelength of the quantum dots according to Comparative Example 1 were measured using Comparative Sample 1. The results are shown in Table 1.
  • the quantum efficiencies of the composites according to Examples 1 to 6 in the state dispersed in toluene are 83.8%, 83.1%, 83.0%, 82.7%, 82.9% and 82.6%. Able to know.
  • the quantum efficiencies of the composites according to Examples 7 and 8 in the state dispersed in toluene are 82.9% and 82.5%, respectively.
  • the quantum efficiency of the composite according to Examples 1 to 8 of the present invention in the state dispersed in toluene is the same as that of Comparative Example 1 It can be seen that higher than the quantum efficiency. That is, even when the composite is manufactured using the quantum dots, it can be seen that the quantum efficiency of the composite is not lower than the quantum efficiency of the quantum dots themselves.
  • the emission wavelengths of the composites according to Examples 1 to 6 were 606.4 nm, 606.7 nm, 606.5 nm, 606.3 nm, 606.1 nm and 606.9 nm, and Example 7 And it can be seen that the emission wavelength of each of the composites according to 8 are 606.3 nm and 606.8 nm.
  • the emission wavelength of the quantum dot according to Comparative Example 1 is 606.0 nm.
  • the emission wavelength of the composite dispersed in toluene is longer than the emission wavelength of the quantum dot itself.
  • the emission wavelength of the composite according to the present invention is longer than the emission wavelength of the quantum dot itself, but the difference is less than about 1 nm, the emission wavelength of the composite in the state dispersed in toluene is substantially the same as the emission wavelength of the quantum dot itself. The same can be said. That is, even when the quantum dot is encapsulated with a wax-based compound, it can be seen that there is almost no shift in the emission wavelength compared to the emission wavelength of the quantum dot itself.
  • Each of the composites according to Examples 1 to 8 of the present invention has a B kit and an optical density (OD) value of 0.1 in an OE-6630 A / B kit (trade name, Dow Corning Silicon, USA), which is a siloxane resin. Mixtures at concentrations produced measurement samples 9-16.
  • Comparative Sample 2 was prepared by mixing quantum dots according to Comparative Example 1 with OE-6630 and an OD value of 0.1.
  • the quantum efficiencies of the composites according to Examples 1 to 6 were 87.3%, 86.5%, 84.9%, 85.7%, 83.5%, and 82.9. %, And the quantum efficiencies of the composites according to Examples 7 and 8 are 75.0% and 74.6%, respectively.
  • the composite including the quantum dots encapsulated by the wax-based compound shows a high quantum efficiency compared to the quantum dots dispersed in the siloxane resin, even in the state dispersed in the siloxane resin. It can be seen.
  • the quantum efficiency of measurement sample 9 in which the composite was dispersed in siloxane resin was 87.3%, which is different from the quantum efficiency of 83.8% of measurement sample 1 in which the composite was dispersed in toluene. It can be seen that + 3.5%.
  • the quantum efficiency of measurement sample 10 is 86.5%, and it can be seen that the difference from 83.1%, which is the quantum efficiency of measurement sample 2, is + 3.4%. It can be seen that the quantum efficiencies of each of the measurement samples 11 to 14 are + 1.9%, + 3%, + 0.6%, and + 0.3% from the quantum efficiency of each of the measurement samples 3 to 6.
  • the composites according to Examples 1 to 6 of the present invention maintain or increase quantum efficiency even when dispersed in the siloxane resin, whereas the quantum dot is significantly reduced when dispersed in the siloxane resin.
  • the quantum dots are encapsulated when the wax-based compound is an oxygen-free wax or a wax having an acid value of about 180 mg KOH / g. If the quantum dot itself is improved than the quantum efficiency itself, it can be seen that the quantum efficiency may be lowered when mixed with the siloxane resin.
  • the emission wavelength of the composite according to Examples 1 to 6 is 609.5 nm, 609.7 nm, 610.6 nm, 610.3 nm, 611.6 nm and 612.4 nm, and Example 7 and It can be seen that the emission wavelength of each of the composites according to 8 is 614.3 nm and 612.6 nm. It can be seen that the emission wavelength of the quantum dot according to Comparative Example 1 is 614.5 nm.
  • both of the composites according to Examples 1 to 8 of the present invention and the quantum dots according to Comparative Example 1 have a longer emission wavelength when dispersed in the siloxane resin than 606.0 nm, which is the emission wavelength of the quantum dots themselves dispersed in toluene. Able to know.
  • the emission wavelength of Measurement Sample 9 is longer by 3.1 nm than the emission wavelength of Measurement Sample 1. It can be seen that the emission wavelength of each of the measurement samples 10 to 14 increases by 3.0 nm, 4.1 nm, 4.0 nm, 5.0 nm and 5.5 nm compared to the emission wavelength of each of the measurement samples 2 to 6. It can be seen that the emission wavelength of each of the measurement samples 15 and 16 increases by 8 nm and 5.8 nm compared to the emission wavelength of the measurement samples 7 and 8 respectively.
  • the change in the emission wavelength of the composites according to Examples 1 to 6 of the present invention is smaller than the change in the emission wavelength of the quantum dot according to Comparative Example 1. That is, in the process of dispersing the composite or the quantum dots in the siloxane resin, the composite or the quantum dots are aggregated (aggregation), the phenomenon that the emission wavelength is relatively longer when dispersed in the siloxane resin than the emission wavelength in toluene, which is a simple dispersion solvent This happens. Nevertheless, when the composites according to the present invention are dispersed in the siloxane resin, it can be seen that the change in the emission wavelength is relatively small compared to the case where the quantum dots are dispersed in the siloxane resin as it is.
  • the composite according to Example 7 shows quantum efficiency at a level similar to that of the measurement samples 1 to 6 in the state dispersed in toluene.
  • the wax-based compound constituting the composite according to Example 7 does not contain oxygen, so that when dispersed in the siloxane resin, although the quantum efficiency is higher than that of the quantum dots according to Comparative Example 1, the examples 1 to It can be seen that the quantum efficiency is lower than the composite according to 6.
  • the composite according to Example 7 was dispersed in siloxane resin (measurement sample 15), it was found that the change in emission wavelength was large when compared with the case where the emission wavelength was dispersed in toluene (measurement sample 7).
  • the quantum efficiency is shown to be similar to those of the measurement samples 1 to 6 in the state dispersed in toluene.
  • the quantum efficiency is higher than that of the quantum dot according to Comparative Example 1, It can be seen that the quantum efficiency is lower than the resulting composite.
  • transmittance immediately after dispersion is a value calculated from an arithmetic mean of a transmittance within a range of about 400 nm to about 700 nm, which is a visible light region measured by a transmittance measuring device immediately after the measurement sample or the comparative sample is prepared. :%)to be.
  • transmittance measured after one month refers to a transmittance within a range of about 400 nm to about 700 nm, which is a visible light region measured by a transmittance measuring device at a point in which one month has elapsed after the measurement sample or the comparative sample is manufactured. , Calculated as the arithmetic mean (%).
  • Dispersion stability of Table 3 is computed by calculating the transmittance
  • the dispersion stability of measurement samples 9 to 16 is 2%, 4%, 3%, 5%, 6%, 6%, 13% and 14%, respectively.
  • the dispersion stability of Comparative Sample 2 is 18%. That is, it can be seen that the dispersion stability of the measurement samples 9 to 16 including the composite according to the embodiments of the present invention is relatively superior to the comparative sample 2. It can be seen that even after time, no precipitation occurs and the state remains dispersed in the siloxane resin. In particular, in the case of measurement samples 15 and 16, although dispersion stability is good compared with the comparative sample 2, it turns out that dispersion stability is not good compared with the measurement samples 9-14.
  • the ultraviolet stability of the composite according to Examples 1 to 8 is 15%, 19%, 21%, 19%, 22%, 21%, 29% and 30%, respectively, according to Comparative Example 1
  • the UV stability of the quantum dot is 52%.
  • the better the stability to ultraviolet rays the smaller the change in the quantum efficiency under the harsh conditions of the ultraviolet rays (irradiation amount of about 540 J / cm 2 ), the smaller the ultraviolet stability. That is, it can be seen that the ultraviolet stability of the composite according to Examples 1 to 8 of the present invention is superior to the quantum dots according to Comparative Example 1.
  • the ultraviolet stability of the composite according to Examples 1 to 6 is superior to the ultraviolet stability of the composite according to Examples 7 and 8.
  • the thermal / moisture stability of the composites according to Examples 1 to 8 were 16%, 18%, 21%, 21%, 24%, 25%, 41% and 42%, respectively, whereas the quantum dots according to Comparative Example 1
  • the heat / moisture stability is 55%.
  • the greater the stability to temperature and humidity the smaller the change in quantum efficiency under high temperature and high humidity (temperature 85 ° C. and relative humidity 85%), and therefore the smaller the heat / moisture stability. That is, it can be seen that the thermal / moisture stability of the composites according to Examples 1 to 8 of the present invention is superior to the quantum dots according to Comparative Example 1.
  • the thermal / moisture stability of the composites according to Examples 1 to 6 is superior to that of the composites according to Examples 7 and 8.
  • the composite according to Example 1 was dispersed in OE-6630 B kit and OE-6630 A kit and 1: 4 (A kit: B kit) The mixture was mixed at a mass ratio of and a heat treatment was performed in an oven at about 150 ° C. for about 2 hours to prepare a first film sample having a thickness of about 200 ⁇ m.
  • the second to eighth film samples were prepared through a process substantially the same as that of preparing the first film sample.
  • the first comparative film sample was manufactured through a process substantially the same as the process of preparing the first film sample using the quantum dot according to Comparative Example 1.
  • the ultraviolet stability of the first to eighth film samples is compared with the ultraviolet stability of the first comparative film sample, the ultraviolet stability of the film samples including the composite according to Examples 1 to 8 of the present invention is quantum dots It can be seen that it is superior to the first comparative film sample including the.
  • the ultraviolet stability of the seventh and eighth film samples is better than that of the first comparative film sample, but it is not good compared to the first to sixth film samples. That is, it can be seen that the ultraviolet stability of the first to sixth film samples is very excellent at a level of about 6% or less.
  • the heat / moisture stability of the film samples comprising the composite according to Examples 1 to 8 of the present invention. It turns out that it is excellent compared with this 1st comparative film sample.
  • the heat / moisture stability of the seventh and eighth film samples is better than that of the first comparative film sample, but not as good as the first to sixth film samples. have. That is, it can be seen that the heat / moisture stability of the first to sixth film samples is very good at a level of about 11% or less.
  • the ultraviolet stability and the heat / moisture stability of the composite according to the present invention are superior to those of using the quantum dot as it is.
  • Example 1 After dissolving MB2478 (trade name, Mitsubishi Rayon, Japan) in toluene, the composite according to Example 1 was dispersed and dried at about 80 ° C. to prepare a ninth film sample having a thickness of about 200 ⁇ m.
  • the tenth to sixteenth film samples were prepared by substantially the same process as the process for preparing the ninth film sample using the composite according to Examples 2 to 8.
  • the second comparative film sample was manufactured by substantially the same process as the process of manufacturing the ninth film sample using the quantum dot according to Comparative Example 1.
  • the ultraviolet stability of the ninth to sixteenth film samples with the ultraviolet stability of the second comparative film sample, the ultraviolet stability of the film samples including the composite according to Examples 1 to 8 of the present invention, respectively 8%, 9%, 11%, 14%, 13%, 16%, 27% and 35%, the UV stability of the second comparative film sample containing quantum dots is excellent when compared to 48%. .
  • the ultraviolet stability of the fifteenth and sixteenth film samples is better than that of the second comparative film sample, but it is not good compared to the ninth to fourteenth film samples. That is, it can be seen that the ultraviolet stability of the ninth to fourteenth film samples is excellent at a level of about 16% or less.
  • the heat / moisture stability of the ninth to sixteenth film samples when comparing the heat / moisture stability of the ninth to sixteenth film samples with the heat / moisture stability of the second comparative film sample, the heat / moisture stability of the film samples including the composite according to Examples 1 to 8 of the present invention. As 5%, 7%, 7%, 13%, 10%, 12%, 32% and 34%, it can be seen that the heat / moisture stability of the first comparative film sample is superior to that of 43%.
  • the heat / moisture stability of the fifteenth and sixteenth film samples is better than that of the second comparative film sample, but not as good as the ninth to fourteenth film samples. have. That is, it can be seen that the heat / moisture stability of the ninth to fourteenth film samples is very good at a level of about 13% or less.
  • the ultraviolet stability and the heat / moisture stability of the composite according to the present invention are superior to those of using the quantum dots as they are.
  • 3 to 5 are cross-sectional views illustrating an apparatus according to another embodiment of the present invention.
  • a light emitting device 501 is formed on a light emitting diode (LED) element portion 10 and the LED element portion 10 and includes a first composite including the composite according to the present invention as described above.
  • the cured product layer 310 and the second cured product layer 320 are included.
  • the LED element part 10 includes a base part 2 and an LED chip 1 formed in a groove part of the base part 2.
  • the first cured product layer 310 includes a green composite 311 dispersed in a matrix structure formed by the curable resin.
  • the green composite 311 includes green quantum dots, and the green quantum dots are encapsulated by a wax-based compound.
  • the "matrix structure” means the internal structure of the cured product formed by the curable resin of the composition used to form the first cured product layer 310 by chemical reaction. Since the wax-based compound is substantially the same as described with reference to FIGS. 1A, 1B, and 1C, detailed descriptions thereof will not be repeated.
  • the second cured product layer 320 includes an encapsulated red composite material 321 dispersed in a matrix structure formed by the curable resin.
  • the red complex 321 includes red quantum dots, and the red quantum dots are encapsulated by a wax-based compound.
  • the wax compound encapsulating the red quantum dots may be the same as or different from the wax compound encapsulating the green quantum dots.
  • the green composite 311 may have a light emission peak at about 520 nm to about 570 nm, which is a green wavelength region.
  • the red complex 321 may have a light emission peak at about 600 nm to about 680 nm, which is a red wavelength region.
  • the red wavelength region may be about 620 nm to about 670 nm.
  • the LED chip 1 generates blue light.
  • the blue light may have a wavelength of about 400 nm to about 480 nm.
  • the blue wavelength region may be about 400 nm to about 450 nm.
  • the first cured material layer 310 may include a red composite 321, and the second cured material layer 320 may include a green composite 311.
  • the light emitting device includes a green composite 311 and a red composite 321, and includes a cured product layer covering the LED chip 1. May have
  • the light emitting device 502 includes a phosphor layer 410 including an LED element unit 10, a first cured product layer 310, a second cured product layer 320, and a phosphor 411. Include.
  • the light emitting device 502 is substantially the same as the light emitting device 501 described with reference to FIG. 3 except for the fluorescent layer 410. Therefore, redundant descriptions are omitted.
  • the fluorescent layer 410 may compensate for light emission of the green composite 311 of the first cured product layer 310 and / or the red composite 321 of the second cured material layer 320.
  • the phosphor 411 may have a light emission peak at, for example, about 520 nm to about 570 nm in a green region and / or about 600 nm to about 680 nm in a red region. In contrast, the phosphor 411 may have a light emission peak at about 580 nm to about 600 nm, which is a yellow region.
  • the light emitting device 503 includes an LED element unit 10 and a cured product layer ML.
  • the cured product layer ML may include all of the green composite 311, the red composite 321, and the phosphor 411 dispersed in a matrix structure formed by the curable resin.
  • the light emitting device includes a first layer including two compounds of the green complex 311, the red complex 321, and the phosphor 411, and a second layer including the remaining one compound. It may include.
  • the light emitting device when the LED chip is a light emitting chip that generates UV light, the light emitting device includes a first layer including a blue composite, a second layer including a green composite, and a third layer including a red composite on the light emitting chip. It may have a laminated structure. At this time, each of the red, green and blue composites includes a quantum dot encapsulated with a wax-based compound according to the present invention. The stacking order of the first to third layers may be variously changed.
  • the composite according to the present invention having good UV stability and heat / moisture stability, and the life of the light emitting device can be shortened due to damage of the quantum dots. You can prevent it.
  • the composite according to the present invention is dispersed in a resin to form a cured product layer, shift of emission peaks can be minimized. Accordingly, the light emitting device or the display device can be easily controlled to have the color characteristics (spectrum) required by the user, and color reproducibility can be improved.
  • a light emitting device that satisfies both color reproducibility and lifespan characteristics can be manufactured.

Abstract

L'invention concerne un composite qui comprend au moins un point quantique et un composé à base de cire qui couvre une surface du point quantique. Le composite a une efficacité quantique remarquable, un petit changement du pic d'émission même si le composite est dispersé dans une résine et une excellente stabilité de dispersion, une excellente stabilité aux rayons UV et une excellente thermostabilité/stabilité à l'humidité.
PCT/KR2013/010094 2012-11-09 2013-11-07 Composite, composition le contenant et appareil WO2014073895A1 (fr)

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KR10-2012-0126925 2012-11-09
KR20120126925 2012-11-09
KR1020130079501A KR101396871B1 (ko) 2012-11-09 2013-07-08 복합체, 이를 포함하는 조성물 및 장치
KR10-2013-0079501 2013-07-08

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
US10267488B2 (en) * 2014-12-08 2019-04-23 Lg Electronics Inc. Method for preparing quantum dot-polymer complex, quantum dot-polymer complex, light conversion film, backlight unit and display device having the same
CN112424268A (zh) * 2018-06-29 2021-02-26 株式会社尹诺丘迪 量子点膜的制备方法、由此制备的量子点膜及包括该量子点膜的波长转换片和显示器

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KR20070119104A (ko) * 2006-06-14 2007-12-20 재단법인서울대학교산학협력재단 양자점을 이용한 백색광 ｌｅｄ 구조 및 그 제조 방법
KR20100030264A (ko) * 2008-09-10 2010-03-18 연세대학교 산학협력단 형광 자성 나노복합체 및 그 제조방법
WO2011036446A1 (fr) * 2009-09-23 2011-03-31 Nanoco Technologies Ltd Matériaux à base de nanoparticules semi-conductrices
US20120004345A1 (en) * 2010-07-05 2012-01-05 Doris Pik-Yiu Chun Polymer-encapsulated colorant nanoparticles

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KR20070119104A (ko) * 2006-06-14 2007-12-20 재단법인서울대학교산학협력재단 양자점을 이용한 백색광 ｌｅｄ 구조 및 그 제조 방법
KR20100030264A (ko) * 2008-09-10 2010-03-18 연세대학교 산학협력단 형광 자성 나노복합체 및 그 제조방법
WO2011036446A1 (fr) * 2009-09-23 2011-03-31 Nanoco Technologies Ltd Matériaux à base de nanoparticules semi-conductrices
US20120004345A1 (en) * 2010-07-05 2012-01-05 Doris Pik-Yiu Chun Polymer-encapsulated colorant nanoparticles

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10267488B2 (en) * 2014-12-08 2019-04-23 Lg Electronics Inc. Method for preparing quantum dot-polymer complex, quantum dot-polymer complex, light conversion film, backlight unit and display device having the same
CN112424268A (zh) * 2018-06-29 2021-02-26 株式会社尹诺丘迪 量子点膜的制备方法、由此制备的量子点膜及包括该量子点膜的波长转换片和显示器

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