WO2019038731A1 - Composition comprenant des points quantiques réticulés - Google Patents

Composition comprenant des points quantiques réticulés Download PDF

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Publication number
WO2019038731A1
WO2019038731A1 PCT/IB2018/056453 IB2018056453W WO2019038731A1 WO 2019038731 A1 WO2019038731 A1 WO 2019038731A1 IB 2018056453 W IB2018056453 W IB 2018056453W WO 2019038731 A1 WO2019038731 A1 WO 2019038731A1
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Prior art keywords
alkyl
heteroaromatic
cycloalkyl
nanoparticle
quantum dots
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PCT/IB2018/056453
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English (en)
Inventor
Changmin Lee
Hyunjin Kang
Namhun Kim
DaeKyung KIM
Heeyeop Chae
Seongwon Kim
Jong Woo Lee
Soonyoung HYUN
Kahee SHIN
Sunyoung Lee
Jeongmin LIM
Chunim LEE
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Sabic Global Technologies B.V.
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Publication of WO2019038731A1 publication Critical patent/WO2019038731A1/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
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • 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

Definitions

  • the present disclosure relates to a composition including a cross-linked quantum dot nanoparticle matrix, and in particular to a composition in which the quantum dot nanoparticle matrix is cross-linked by ligands.
  • Nanoparticles in a polymer matrix are easily aggregated in the matrix due to their high surface energy. Once formed, nanoparticle aggregates are difficult to disrupt. In addition, nanoparticle aggregates have a tendency to grow in size.
  • the aggregates When aggregation occurs in quantum dot nanoparticles in display applications, the aggregates reduce the quantum yield of the quantum dot nanoparticles by causing energy transfer between neighboring quantum dots aggregated in the matrix.
  • Dexter energy transfer occurs between quantum dot nanoparticles spaced less than about 1 nanometer (nm) from each another, and Forster resonance energy transfer (FRET) occurs between quantum dot nanoparticles spaced from about 1 nm to about 10 nm from each other.
  • DET Dexter energy transfer
  • FRET Forster resonance energy transfer
  • FIG. 1 illustrates a portion of a quantum dot nanoparticle matrix 100 according to an aspect of the disclosure.
  • aspects of the disclosure relate to a composition including a cross-linked quantum dot nanoparticle matrix, the cross-linked quantum dot nanoparticle matrix including a plurality of nanoparticle quantum dots cross-linked by ligands.
  • the ligands include one or more various compounds, including but not limited to one or more compounds including an isocyanate group or an isothiocyanate group and one or more compounds including at least two alcohol groups, at least two thiol groups or a combination thereof.
  • the ligands are selected so as to minimize or prevent agglomeration of quantum dots and ensure that the plurality of nanoparticle quantum dots in the cross-linked quantum dot nanoparticle matrix are spaced apart from each other by at least about 10 nanometers, which minimizes or prevents Forster Resonance Energy Transfer between neighboring quantum dots.
  • the resulting cross-linked quantum dot nanoparticle matrix has enhanced optical properties as compared to conventional quantum dot films.
  • aspects of the disclosure further relate to methods for making a cross-linked quantum dot nanoparticle matrix, the cross-linked quantum dot nanoparticle matrix including a plurality of nanoparticle quantum dots cross-linked by ligands.
  • the ligands include one or more various compounds, including but not limited to one or more compounds including an isocyanate group or an isothiocyanate group and one or more compounds including at least two alcohol groups, at least two thiol groups or a combination thereof.
  • the method includes combining the plurality of nanoparticle quantum dots and ligands, and heating the plurality of nanoparticle quantum dots and ligands to cure the composition and form the cross-linked quantum dot nanoparticle matrix.
  • compositions including a cross-linked quantum dot nanoparticle matrix including a plurality of nanoparticle quantum dots cross- linked by ligands include: compounds of the formula
  • one or more compounds including an isocyanate group or an isothiocyanate group one or more compounds including at least two alcohol groups, at least two thiol groups or a combination thereof; or a combination thereof.
  • Ranges can be expressed herein as from one value (first value) to another value (second value). When such a range is expressed, the range includes in some aspects one or both of the first value and the second value. Similarly, when values are expressed as approximations, by use of the antecedent 'about,' it will be understood that the particular value forms another aspect. It will be further understood that the endpoints of each of the ranges are significant both in relation to the other endpoint, and independently of the other endpoint.
  • the terms “about” and “at or about” mean that the amount or value in question can be the designated value, approximately the designated value, or about the same as the designated value. It is generally understood, as used herein, that it is the nominal value indicated ⁇ 10% variation unless otherwise indicated or inferred. The term is intended to convey that similar values promote equivalent results or effects recited in the claims. That is, it is understood that amounts, sizes, formulations, parameters, and other quantities and characteristics are not and need not be exact, but can be approximate and/or larger or smaller, as desired, reflecting tolerances, conversion factors, rounding off, measurement error and the like, and other factors known to those of skill in the art.
  • an amount, size, formulation, parameter or other quantity or characteristic is “about” or “approximate” whether or not expressly stated to be such. It is understood that where "about” is used before a quantitative value, the parameter also includes the specific quantitative value itself, unless specifically stated otherwise.
  • the terms “optional” or “optionally” means that the subsequently described event or circumstance can or cannot occur, and that the description includes instances where said event or circumstance occurs and instances where it does not.
  • the phrase “optional additional additives” means that the additional additives can or cannot be included and that the description includes compositions that both include and do not include additional additives.
  • compositions of the disclosure Disclosed are the components to be used to prepare the compositions of the disclosure as well as the compositions themselves to be used within the methods disclosed herein. These and other materials are disclosed herein, and it is understood that when combinations, subsets, interactions, groups, etc. of these materials are disclosed that while specific reference of each various individual and collective combinations and permutation of these compounds cannot be explicitly disclosed, each is specifically contemplated and described herein. For example, if a particular compound is disclosed and discussed and a number of modifications that can be made to a number of molecules including the compounds are discussed, specifically contemplated is each and every combination and permutation of the compound and the modifications that are possible unless specifically indicated to the contrary.
  • references in the specification and concluding claims to parts by weight of a particular element or component in a composition or article denotes the weight relationship between the element or component and any other elements or components in the composition or article for which a part by weight is expressed.
  • X and Y are present at a weight ratio of 2:5, and are present in such ratio regardless of whether additional components are contained in the compound.
  • a weight percent of a component is based on the total weight of the formulation or composition in which the component is included.
  • weight percent As used herein the terms "weight percent,” “wt%,” and “wt. %,” which can be used interchangeably, indicate the percent by weight of a given component based on the total weight of the composition, unless otherwise specified. That is, unless otherwise specified, all wt% values are based on the total weight of the composition. It should be understood that the sum of wt% values for all components in a disclosed composition or formulation are equal to 100. [0024] Unless otherwise stated to the contrary herein, all test standards are the most recent standard in effect at the time of filing this application.
  • compositions disclosed herein have certain functions.
  • compositions including cross-linked quantum dot nanoparticle matrix
  • compositions including a cross-linked quantum dot nanoparticle matrix.
  • the cross-linked quantum dot nanoparticle matrix includes a plurality of nanoparticle quantum dots cross-linked by ligands.
  • the ligands include:
  • one or more compounds including at least two alcohol groups, at least two thiol or a combinati or (7) (6)
  • Rl is a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C4-24 aryl, a C4-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic,
  • Zl, Z2, Z3, Z4, Z5 and Z6 are independently an isocyanate or isothiocyanate
  • R2 is a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C6-24 aryl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic,
  • R3, R4 and R5 are independently a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl- alkyl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic,
  • VI, V2 and V3 are independently O or S,
  • XI, X2 and X3 are independently N, P or hydrocarbon
  • n 1 or 2
  • R6 is independently H or a methyl group
  • n 1 to 200
  • R7 and R8 are independently a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C6-24 aryl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic,
  • o is an integer from 1 to 1000
  • Z7 is independently an alcohol group or a thiol group
  • R9 is a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C6-24 aryl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic.
  • the plurality of quantum dots in the composition have an absorption wavelength of from about 300 nanometers (nm) to about 480 nm.
  • the plurality of quantum dots can emit green and/or red light when they absorb blue light.
  • composition according to particular aspects of the disclosure may include: from about 0.1 wt% to about 20 wt% nanoparticle quantum dots; from about 10 wt% to about 80 wt% one or more compounds including an isocyanate group or an isothiocyanate group according to Formulas (2) to (5); and from about 10 wt% to about 80 wt% one or more compounds including at least two alcohol groups, at least two thiol groups or a combination thereof, according to Formulas (6) or (7).
  • FIG. 1 illustrates a portion of a quantum dot nanoparticle matrix 100 according to an aspect of the disclosure.
  • the quantum dot nanoparticle matrix 100 includes a plurality of nanoparticle quantum dots 200 and a plurality of ligands 300 that cross-link the plurality of nanoparticle quantum dots 200.
  • the nanoparticle quantum dots 200 are separated from one another by a distance (e.g., dl, d2).
  • the plurality of nanoparticle quantum dots 200 in the nanoparticle matrix 100 are spaced apart from each other by at least about 10 nanometers (nm). The spacing is ensured by selection of ligands 300 according to the formulas described herein.
  • FRET Forster Resonance Energy Transfer
  • a fluorescent donor e.g., a quantum dot emitting light at a higher energy
  • a lower energy acceptor e.g., a quantum dot emitting light at a lower energy
  • one or more of the plurality of nanoparticle quantum dots is a metal nanomaterial or an inorganic nanomaterial.
  • the form of the plurality of nanoparticle quantum dots may include in certain aspects a nanoparticle, a nanofiber, a nanorod, or a nanowire.
  • the plurality of nanoparticle quantum dots may have a size of from about 1 nanometer (nm) to about 100 nm in some aspects. In particular aspects the plurality of nanoparticle quantum dots have a size of from about 1 nm to about 50 nm, or from about 1 nm to about 30 nm.
  • Exemplary quantum dots according to aspects of the disclosure may include, but are not limited to, semiconductor nanocrystals selected from the group consisting of, but not limited to, Group II- VI semiconductor compounds, Group II-V semiconductor compounds, Group III-VI semiconductor compounds, Group III-V semiconductor compounds, Group IV-VI semiconductor compounds, Group II-III-VI compounds, Group II- IV-VI compounds, Group II-IV-V compounds, alloys thereof and combinations thereof.
  • Exemplary Group II elements include Zn, Cd, Hg or a combination thereof.
  • Exemplary Group III elements include Al, Ga, In, Ti or a combination thereof.
  • Exemplary Group IV elements include Si, Ge, Sn, Pb or a combination thereof.
  • Exemplary Group V elements include P, As, Sb, Bi or a combination thereof.
  • Exemplary Group VI elements include O, S, Se, Te or a combination thereof.
  • Exemplary Group II-VI semiconductor compounds include binary compounds, e.g., CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe and HgTe; ternary compounds, e.g., CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS and HgZnSe; and quaternary compounds, e.g., CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZn
  • Exemplary Group III-V semiconductor compounds include binary compounds, e.g., GaN, GaP, GaAs, GaSb, A1N, A1P, AlAs, AlSb, InN, InP, InAs and InSb; ternary compounds, e.g., GaNP, GaNAs, GaNSb, GaPAs, GaPSb, A1NP, AINAs, AINSb, AlPAs, AlPSb, InNP, InNAs, InN Sb, InPAs, InPSb, GaAlNP, AlGaN, AlGaP, AlGaAs, AlGaSb, InGaN, InGaP, InGaAs, InGaSb, AlInN, AllnP, AlInAs and AllnSb; and quaternary compounds, e.g., GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GalnNP, Gain, NAs, GalnNSb, Gal
  • Exemplary Group IV-VI semiconductor compounds include binary compounds, e.g., SnS, SnSe, SnTe, PbS, PbSe and PbTe; ternary compounds, e.g., SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe and SnPbTe; and quaternary compounds, e.g., SnPbSSe, SnPbSeTe and SnPbSTe.
  • Exemplary Group IV semiconductor compounds include unary compounds, e.g., Si and Ge; and binary compounds, e.g., SiC and SiGe.
  • each of the plurality of nanoparticle quantum dots include a concentration-gradient quantum dot.
  • a concentration-gradient quantum dot includes an alloy of at least two semiconductors. The concentration (molar ratio) of the first semiconductor gradually increases from the core of the quantum dot to the outer surface of the quantum dot, and the concentration (molar ratio) of the second semiconductor gradually decreases from the core of the quantum dot to the outer surface of the quantum dot.
  • concentration-gradient quantum dots are described in, e.g., U.S. Patent No.
  • the concentration-gradient quantum dot includes two semiconductors, a first semiconductor having the formula
  • the concentration-gradient quantum dot includes two semiconductors, a first semiconductor having the formula
  • the core and the shell or plurality of shells may independently be formed of the semiconductor materials described above.
  • the quantum dot nanoparticle matrix 100 may further include in some aspects any suitable polymer.
  • suitable polymers include, but are not limited to, polycarbonate (PC), polyethylene terephthalate (PET), polymethyl methacrylate (PMMA), polyaryletherketones (PAEK), polyimides, polyolefins, polystyrene, or a combination thereof.
  • the quantum dot nanoparticle matrix 100 is in the form of a film.
  • the quantum dot nanoparticle matrix 100 may include one or more additional films or layers, such as a barrier film, in certain aspects.
  • a barrier film may provide further protection to the quantum dot nanoparticle matrix 100.
  • Conventional barrier films include an inorganic layer.
  • Exemplary materials for use in a barrier film include, but are not limited to, metal oxides, metal nitrides, metal carbides, metal oxynitrides, metal oxyborides, and combinations thereof, e.g., silicon oxides such as silica, aluminum oxides such as alumina, titanium oxides such as titania, indium oxides, tin oxides, indium tin oxide ("ITO"), tantalum oxide, zirconium oxide, niobium oxide, boron carbide, tungsten carbide, silicon carbide, aluminum nitride, silicon nitride, boron nitride, aluminum oxynitride, silicon oxynitride, boron oxynitride, zirconium oxyboride, titanium oxyboride, and combinations thereof.
  • silicon oxides such as silica
  • aluminum oxides such as alumina
  • titanium oxides such as titania, indium oxides, tin oxides, indium t
  • the quantum dot nanoparticle matrix 100 and/or one or more additional films or layers (if included) may in some aspects include optional additional additives, as desired, that do not adversely affect the optical properties of the plurality of quantum dots 200 in the quantum dot nanoparticle matrix 100.
  • optional additional additives include, but are not limited to, a scattering material, a coupling agent, a leveling agent, a dispersant, a binder, a scavenger, a stabilizer and a combination thereof.
  • the quantum dot nanoparticle matrix 100 and/or one or more additional films or layers (if included) includes a scattering material.
  • Scattering materials which may include but are not limited to metal oxide particles, may be included to modify the optical properties of the plurality of quantum dots 200 by scattering light generated therefrom.
  • Exemplary scattering materials include, but are not limited to, titanium dioxide (TiC ), silicon dioxide (SiC ), aluminum oxide (AI2O3), zinc oxide (ZnO), zinc peroxide (ZnC ), zirconium dioxide (ZrC ), and combinations thereof.
  • the scattering material in some aspects has a particle size of from about 0.1 micrometer ( ⁇ ) to about 10 ⁇ .
  • the quantum dot nanoparticle matrix includes a plurality of nanoparticle quantum dots cross-linked by ligands, and the ligands include one or more compounds including an isocyanate group or an isothiocyanate group having a molecular weight of 800 or greater.
  • aspects of the disclosure further relate to methods for making a composition including a cross-linked quantum dot nanoparticle matrix, including: combining a plurality of nanoparticle quantum dots and ligands; and heating the plurality of nanoparticle quantum dots and ligands to cure the composition and form the cross-linked quantum dot nanoparticle matrix.
  • the ligands include:
  • compounds of Formula (1) one or more compounds including an isocyanate group or an isothiocyanate group according to Formulas (2) to (5) (2)
  • Rl is a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C4-24 aryl, a C4-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic, Zl, Z2, Z3, Z4, Z5 and Z6 are independently an isocyanate or isothiocyanate,
  • R2 is a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C6-24 aryl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic,
  • R3, R4 and R5 are independently a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl- alkyl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic,
  • VI, V2 and V3 are independently O or S,
  • XI, X2 and X3 are independently N, P or hydrocarbon
  • n 1 or 2
  • R6 is independently H or a methyl group
  • n 1 to 200
  • R7 and R8 are independently a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C6-24 aryl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic,
  • o is an integer from 1 to 1000
  • Z7 is independently an alcohol group or a thiol group
  • R9 is a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C6-24 aryl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic.
  • the heating step is performed at a temperature sufficient to cross-link the ligands in the quantum dot nanoparticle matrix. In some aspects the heating is performed at a temperature of from about 60 to about 120 degrees Celsius (°C).
  • the plurality of nanoparticle quantum dots in the nanoparticle matrix are dispersed such that a film/article including the nanoparticle matrix exhibits no appreciable degradation of optical properties after chemical exposure with acetone for 5 minutes.
  • "no appreciable degradation of optical properties” means that, when the composition including the quantum dot nanoparticle matrix is exposed to the stated condition, the emission spectra of the composition either does not change or does not change to a substantial degree (e.g., the change is less than about 10%).
  • Emission spectra of a composition may be quantified by measuring the width of the Gaussian curve of the emission spectra at half of its maximum value, known as "full width at half maximum," or FWHM.
  • no appreciable degradation of optical properties refers to a change in FWHM of no more than about 10% or a shift in peak wavelength (PWL) of no more than about 10%.
  • PWL peak wavelength
  • no appreciable degradation of optical properties means that, when the composition including the quantum dot nanoparticle matrix is exposed to the stated condition, it exhibits a shift in PWL of less than 20 nm, or less than 15 nm, or less than 10 nm, or less than 5 nm.
  • no appreciable degradation of optical properties means that, when the composition including the quantum dot nanoparticle matrix is exposed to the stated condition, it exhibits a reduction in luminance of less than about 10% as compared to the luminance of the composition prior to exposure to the stated condition.
  • aspects of the disclosure also relate to an article including the cross-linked quantum dot nanoparticle matrix described herein.
  • the article is film.
  • the film has a thickness of from about 0.5 micron ( ⁇ ) to about 500 ⁇ .
  • the film may be incorporated into a display for an electronic device.
  • the electronic device may include but is not limited to a mobile device, a tablet device, a gaming system, a handheld electronic device, a wearable device, a television, a desktop computer, or a laptop computer.
  • the quantum dot film may in particular aspects be used in multi-layer extrusion (MLE), micro lens, prism and diffuser applications.
  • MLE multi-layer extrusion
  • the present disclosure pertains to and includes at least the following aspects.
  • a composition comprising, consisting of or consisting essentially of a cross-linked quantum dot nanoparticle matrix, wherein the cross-linked quantum dot nanoparticle matrix comprises a plurality of nanoparticle quantum dots cross-linked by ligands, the ligands comprising:
  • R 2 z 2 one or more compounds comprising at least two alcohol groups, at least two thiol groups or a combination thereof, according to Formulas (6) or (7)
  • Rl is a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C4-24 aryl, a C4-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic,
  • Zl, Z2, Z3, Z4, Z5 and Z6 are independently an isocyanate or isothiocyanate
  • R2 is a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C6-24 aryl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic
  • R3, R4 and R5 are independently a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl- alkyl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic
  • VI, V2 and V3 are independently O or S,
  • XI, X2 and X3 are independently N, P or hydrocarbon
  • n 1 or 2
  • R6 is independently H or a methyl group
  • n 1 to 200
  • R7 and R8 are independently a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C6-24 aryl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic,
  • o is an integer from 1 to 1000
  • Z7 is independently an alcohol group or a thiol group
  • R9 is a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C6-24 aryl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic.
  • Aspect 2 The composition according to Aspect 1, wherein the plurality of quantum dots have an absorption wavelength of from about 300 nanometers (nm) to about 480 nm.
  • Aspect 3 The composition according to Aspect 1 or 2, wherein the plurality of quantum dots have a size of from about 1 nm to about 30 nm.
  • Aspect 4 The composition according to any of Aspects 1 to 3, wherein the composition comprises:
  • Aspect 5 The composition according to any of Aspects 1 to 4, wherein the plurality of nanoparticle quantum dots in the nanoparticle matrix are spaced apart from each other by at least about 10 nanometers (nm).
  • Aspect 6 The composition according to any of Aspects 1 to 5, wherein the plurality of nanoparticle quantum dots in the nanoparticle matrix are dispersed such that the composition exhibits no appreciable degradation of optical properties after chemical exposure with acetone for 5 minutes.
  • Aspect 7 The composition according to any of Aspects 1 to 6, wherein the plurality of nanoparticle quantum dots in the nanoparticle matrix comprise a metal nanomaterial or an inorganic nanomaterial.
  • Aspect 8 The composition according to any of Aspects 1 to 7, wherein one or more of the plurality of nanoparticle quantum dots in the nanoparticle matrix is a nanofiber, a nanorod, or a nanowire.
  • Aspect 9 An article comprising the composition according to any of Aspects l to 8.
  • Aspect 10 The article according to Aspect 9, wherein the article is a film having a thickness of from about 0.5 micron (um) to about 500 ⁇ .
  • Aspect 11 The article according to Aspect 9 or 10, wherein the article is a display for an electronic device.
  • Aspect 12 The article according to Aspect 11, wherein the electronic device is a mobile device, a tablet device, a gaming system, a handheld electronic device, a wearable device, a television, a desktop computer, or a laptop computer.
  • a method for making a composition comprising a cross-linked quantum dot nanoparticle matrix comprising, consisting of or consisting essentially of:
  • Rl is a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C4-24 aryl, a C4-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic,
  • Zl, Z2, Z3, Z4, Z5 and Z6 are independently an isocyanate or isothiocyanate
  • R2 is a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C6-24 aryl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic,
  • R3, R4 and R5 are independently a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl- alkyl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic,
  • VI, V2 and V3 are independently O or S,
  • XI, X2 and X3 are independently N, P or hydrocarbon
  • n 1 or 2
  • R6 is independently H or a methyl group
  • R7 and R8 are independently a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C6-24 aryl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic,
  • o is an integer from 1 to 1000
  • Z7 is independently an alcohol group or a thiol group
  • R9 is a Ci-24 alkyl, a C3-24 cycloalkyl, a C3-24 cycloalkyl-alkyl, a C6-24 aryl, a C6-24 alkyl-aryl, a C4-24 heteroaromatic, or a C4-24 alkyl-heteroaromatic;
  • Aspect 14 The method according to Aspect 13, wherein the heating is performed at a temperature of from about 60 to about 120 degrees Celsius.
  • Aspect 15 The method according to Aspect 13 or 14, wherein the plurality of quantum dots have an absorption wavelength of from about 300 nanometers (nm) to about
  • Aspect 16 The method according to any of Aspects 13 to 15, wherein the plurality of quantum dots have a size of from about 1 nm to about 30 nm.
  • Aspect 17 The method according to any of Aspects 13 to 16, wherein the composition comprises:
  • Aspect 18 The method according to any of Aspects 13 to 17, wherein the plurality of nanoparticle quantum dots in the nanoparticle matrix are spaced apart from each other by at least about 10 nanometers (nm).
  • Aspect 19 The method according to any of Aspects 13 to 18, wherein the plurality of nanoparticle quantum dots in the nanoparticle matrix are dispersed such that the composition exhibits no appreciable degradation of optical properties after chemical exposure with acetone for 5 minutes.
  • Aspect 20 An article formed from the method according to any of Aspects 13 to 19.
  • Aspect 21 The article according to Aspect 20, wherein the article is a film having a thickness of from about 0.5 micron ( ⁇ ) to about 500 ⁇ .
  • Aspect 22 The article according to Aspect 20 or 21, wherein the article is a display for an electronic device.
  • Aspect 23 The article according to Aspect 22, wherein the electronic device is a mobile device, a tablet device, a gaming system, a handheld electronic device, a wearable device, a television, a desktop computer, or a laptop computer.
  • reaction conditions e.g., component concentrations, desired solvents, solvent mixtures, temperatures, pressures and other reaction ranges and conditions that can be used to optimize the product purity and yield obtained from the described process. Only reasonable and routine experimentation will be required to optimize such process conditions.
  • compositions in Table 1 were prepared, including compositions Exl and
  • Exl and C2 included red and green quantum dots with -OH groups (1 milliliter (ml) and 2 ml, respectively), and Ex2 and C2 included red and green quantum dots without -OH groups (1 ml and 2 ml, respectively).
  • Inventive compositions Exl and Ex2 each included a plurality of ligands:
  • Ligand 1 Duranate TKA-100, an isocyanurate trimer, available from Asahi Kasei (2 gram (g)), with the formula
  • compositions of Exl and Ex2 were heated to cross-link the ligands with the quantum dots into the nanoparticle quantum dot matrix.
  • C 1 and C2 substituted 6 grams poly(methyl methacrylate) (PMMA) (molecular weight 110,000, available from Aldrich) for the ligands.
  • PMMA poly(methyl methacrylate)
  • Optical performance of the compositions was measured before and after a chemical resistance test was applied to the compositions.
  • the chemical resistance test was performed by coating a glass slide with the composition, dipping the coated slide into acetone for 5 minutes, and then drying the glass slide in an oven at 120 °C for 3 minutes. Results of the optical testing are shown in Table 2:
  • the luminance of CI and C2 drops precipitously (greater than 50%) after the chemical resistance test).
  • the improved color and luminance of Exl and Ex2 following the chemical resistance test is due to the cross-linked quantum dot matrix, which protects the quantum dots from chemical degradation.
  • the ligands prevent agglomeration of quantum dots in the matrix and minimize Dexter energy transfer (DET) and Forster resonance energy transfer (FRET) between aggregated quantum dots, improving the luminance of the compositions.
  • DET Dexter energy transfer
  • FRET Forster resonance energy transfer
  • Method examples described herein can be machine or computer-implemented at least in part. Some examples can include a computer-readable medium or machine- readable medium encoded with instructions operable to configure an electronic device to perform methods as described in the above examples.
  • An implementation of such methods can include code, such as microcode, assembly language code, a higher-level language code, or the like. Such code can include computer readable instructions for performing various methods. The code may form portions of computer program products. Further, in an example, the code can be tangibly stored on one or more volatile, non-transitory, or nonvolatile tangible computer-readable media, such as during execution or at other times.
  • Examples of these tangible computer-readable media can include, but are not limited to, hard disks, removable magnetic disks, removable optical disks (e.g., compact disks and digital video disks), magnetic cassettes, memory cards or sticks, random access memories (RAMs), read only memories (ROMs), and the like.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Led Device Packages (AREA)
  • Liquid Crystal (AREA)
  • Luminescent Compositions (AREA)

Abstract

L'invention concerne une composition comprenant une matrice de nanoparticules à points quantiques réticulés, la matrice de nanoparticules à points quantiques réticulés comprenant une pluralité de points quantiques nanoparticulaires réticulés par des ligands. Les ligands comprennent un ou plusieurs composés variés, comprenant, mais sans s'y limiter, un ou plusieurs composés comprenant un groupe isocyanate ou un groupe isothiocyanate et un ou plusieurs composés comprenant au moins deux groupes alcool, au moins deux groupes thiol ou une combinaison correspondante. Dans certains aspects, les ligands sont sélectionnés de façon à réduire au minimum ou à empêcher l'agglomération de points quantiques et à assurer que la pluralité de points quantiques nanoparticulaires dans la matrice de nanoparticules à points quantiques réticulés soient espacés les uns des autres d'au moins environ 10 nanomètres, ce qui réduit au minimum ou empêche un transfert d'énergie de résonance de Forster entre des points quantiques voisins. La matrice de nanoparticules à points quantiques réticulés obtenue présente des propriétés optiques améliorées par rapport aux films à points quantiques classiques.
PCT/IB2018/056453 2017-08-25 2018-08-24 Composition comprenant des points quantiques réticulés WO2019038731A1 (fr)

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CN112961666A (zh) * 2021-03-08 2021-06-15 西南石油大学 一种压裂液用纳米复合交联剂及其制备方法
CN113249108A (zh) * 2021-05-14 2021-08-13 西南石油大学 一种耐超高温压裂液及其制备方法

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Publication number Priority date Publication date Assignee Title
CN112961666A (zh) * 2021-03-08 2021-06-15 西南石油大学 一种压裂液用纳米复合交联剂及其制备方法
CN113249108A (zh) * 2021-05-14 2021-08-13 西南石油大学 一种耐超高温压裂液及其制备方法

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