Composition

Abstract

Disclosed are examples of compounds useful as ligands for luminescent particles such as nanoparticles, populations of particles containing such ligands, films and other compositions containing the ligand-bound particles, and methods of synthesis.

Description

[Background technology]

[0001] Nanostructures such as quantum dots (QDs) form colloids in common solvents and are applied to device fabrication by solution processes such as inkjet printing.

[0002] To disperse QDs in ultraviolet (UV)-curable ink compositions, it may be necessary to replace their native nonpolar ligands with more polar species. Commercially available chemicals (e.g., Jeffamine® (polyetheramines based primarily on a polyethylene glycol (PEG) backbone, collectively known as "Jeffamine"), available from Huntsman, Inc., The Woodlands, Texas) aid QD dispersion in commonly used monomer systems, but such ligands may not be optimal for optimizing QD thermal and air stability. In the case of Jeffamine, one cause for concern is the presence of ether linkages near the QD surface. Such groups possess abstractable hydrogens and are prone to radical formation, potentially resulting in radical-mediated damage to the QD surface. Indeed, quantum yields of QDs functionalized with Jeffamine have been observed to rapidly decrease upon exposure to air, even under yellow light. Other candidate ligand systems, such as PEG-280 (a PEG with an average molecular weight of 280 atomic mass units), frequently contain similar ether groups near the amine anchoring group, causing the same problem.

[0003] There remains a need for ligands that can aid in the dispersion of quantum dots (QDs) in polar solutions (e.g., polar UV-curable monomers) and / or can at least partially reduce the degradation of QDs due to thermal and / or oxidative processes. Summary of the Invention

[0004] One aspect of the present disclosure relates to a class of chemical compounds useful as ligands for light-emitting particles, such as nanoparticles. Other aspects relate to populations of particles containing such ligands, films and other compositions containing the ligand-bound particles, and methods of synthesis.

[0005] This Summary is provided to introduce some concepts in a simplified form that are further described in the Detailed Description. This Summary is not intended to identify key features or essential features of the claimed subject matter, nor is it intended to be used to limit the scope of the claimed subject matter. The claimed subject matter is not limited to implementations that solve any shortcomings noted in any part of this disclosure. [Brief explanation of the drawings]

[0006] [Figure 1] FIG. 1 is a line graph showing Fourier transform infrared spectroscopy (FT-IR) spectra of 4-hydroxybutyl acrylate (HBA) alone and (1,3-bis(aminomethyl)cyclohexane) (CHBMA) mixed in a 1:1 molar ratio after 1 minute and 5 minutes of mixing. [Figure 2] FIG. 2 is a line graph showing the proton nuclear magnetic resonance spectrum (H NMR) of the adduct formed between HBA and CHBMA (compound 15), including an inset showing the disappearance of the resonance associated with the double bond of HBA. [Figure 3] Figure 3 is a line graph showing the FT-IR spectrum of AgInGaS / GaS quantum dots in which compounds 15 and 22 are combined as ligands. [Figure 4] Figure 4 shows the 1H NMR spectrum of AgInGaS / GaS quantum dots in which compounds 15 and 22 were combined as ligands. [Figure 5] FIG. 5 is an example box plot showing the photoconversion efficiency (PCE) of a nanostructure film with and without hydroxyl functional groups on the nanostructure ligands. [Figure 6]FIG. 6 is a line graph showing the proton nuclear magnetic resonance spectrum (H NMR) of the adduct formed between CHBMA and AHPMA (compound 113). [Figure 7] FIG. 7 is a line graph showing the proton nuclear magnetic resonance spectrum ( 1 H NMR) of an AIGS quantum dot (AIGSQD) having compound 113 as a ligand. [Figure 8] Figure 8 shows the FTIR spectra of the complete ink liquid printable composition, AHPMA, containing AIGS quantum dots with acylated monomers and CAH ligands, and the final film obtained after curing the film. [Figure 9] FIG. 9 shows a schematic cross-sectional side view of an exemplary light source. [Figure 10A] 10A and 10B show an embodiment of an exemplary display device. [Figure 10B] 10A and 10B show an embodiment of an exemplary display device. [Figure 11] FIG. 11 illustrates an embodiment of an exemplary computer system. DETAILED DESCRIPTION OF THE INVENTION

[0007] Compounds according to examples herein can coordinate to luminescent nanostructures. In examples, these ligands aid in the dispersion of the nanostructures in polar solutions (e.g., polar UV-curable monomers). The compound structures can also at least partially reduce degradation of the nanostructures due to thermal and / or oxidative processes by spacing reactive sites within the ligands away from the nanostructure surface. Some examples herein can include compounds capable of forming hydrogen bonds with other ligands on the nanostructure surface. This allows the ligands to further reduce degradation of the nanostructures due to thermal and / or oxidative processes.

[0008] Additionally, compounds according to the examples herein can be obtained by Michael addition reactions. By selecting a combination of Michael donor and Michael acceptor reagents, the addition reaction can produce a compound or compounds that provide nanostructures with, for example, desired polarity or resistance to degradation processes.

[0009] Some examples herein involve the ligand forming a crosslink with the carrier monomer upon polymerization of the monomer (e.g., by UV or heat), which is believed to lock the ligand and nanostructure in place, potentially reducing nanostructure aggregation and improving the quantum efficiency of the device in use. This cross-linking may also reduce the risk of the nanostructures being exposed to thermal and / or oxidative degradation.

[0010] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the relevant art.

[0011] As used in this specification and the appended claims, the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to a "nanostructure" may include a plurality of such nanostructures.

[0012] As used herein, the term "about" indicates that a given quantity value varies by ±10% of that value. For example, "about 100 nm" encompasses a range of sizes from 90 nm to 110 nm.

[0013] The term nanostructure, as used herein, refers to a structure having at least one region or characteristic dimension, e.g., a dimension of less than about 500 nm. In some examples, nanostructures have dimensions of less than about 200 nm, less than about 100 nm, less than about 50 nm, less than about 20 nm, or less than about 10 nm. Generally, the region or characteristic dimension will be along the smallest axis of the structure. Examples of such nanostructures include nanowires, nanorods, nanotubes, branched nanostructures, nanodots, quantum dots (QDs), nanoparticles, etc. In some examples, each of the three orthogonal dimensions of the nanostructure has a dimension of less than about 500 nm, less than about 200 nm, less than about 100 nm, less than about 50 nm, less than about 20 nm, or less than about 10 nm.

[0014] The term "quantum dot" or "QD" as used herein refers to a nanostructure that is substantially single-crystalline (e.g., includes a single crystal). For example, a QD can have a core-shell structure, where the core is substantially single-crystalline and has one or more shells thereon. A QD has at least one region or characteristic dimension, for example, having a dimension of less than about 500 nm, down to the order of less than about 1 nm. In some examples, a QD has a maximum dimension of about 2 nm to about 30 nm. The quantum dots described herein can be considered fluorescent semiconductor structures, each having a diameter of less than twice the Bohr radius of an exciton induced in the semiconductor crystallite. Such a radius results in quantum confinement of the exciton when induced in the semiconductor crystallite. The Bohr radius depends on the elemental composition of the semiconductor crystallite. For example, the Bohr radius of cadmium selenide (CdSe) is 5.4 nm, so a quasi-spherical CdSe semiconductor crystallite is a quantum dot if its radius is less than 5.4 nm. Examples include zinc selenide telluride (ZnSeTe) microcrystals with a diameter of 4-5 nm, which are blue-emitting quantum dots; indium phosphide (InP) microcrystals with a diameter of 2-2.5 nm, which are green-emitting quantum dots; and InP microcrystals with a diameter of 2.8-3.5 nm, which are red-emitting quantum dots. Quantum confinement of excitons produces fluorescence. Quantum confinement can be induced in three dimensions, two dimensions (quantum wires), or one dimension (quantum wells). Other morphologies of semiconductor microcrystals, such as cubic or tetrahedral, are envisioned.Quantum dots are semiconductors containing III-V semiconductors, II-VI semiconductors, zinc telluride selenide (ZnTeSe), zinc telluride (ZnTe), zinc selenide (ZnSe), zinc sulfide (ZnS), indium phosphide (InP), indium gallium phosphide (InGaP), indium arsenide (InAs), indium arsenide phosphide (InAsP), indium gallium arsenide phosphide (InGaAsP), silver indium gallium sulfide (AgInG The quantum dots may include at least one of copper indium sulfide (CuInS or AIGS), copper indium sulfide (CuInS or CIS), copper indium gallium selenide (CuInGaSe or CIGS), cadmium selenide (CdSe), cadmium sulfide (CdS), cadmium telluride (CdTe), cadmium selenide telluride (CdSeTe), cadmium zinc selenide (CdZnSe), molybdenum sulfide (MoS), or alloys thereof. The ratio between the elements of the alloy is not specified, and various ratios are contemplated as will be understood by those skilled in the art. Each quantum dot may include a core-shell structure with at least one shell on a core, the diameter of the core corresponding to or less than 2x the Bohr radius. The shell may be, for example, a metal sulfide and / or a metal oxide. Exemplary core-shell structures may be formed from CdSe(core) / CdS / ZnS or AgInGaS(core) / GaS. The quantum dots may be functionalized with at least one ligand. Shell and / or ligand functionalization can enhance quantum dot properties, such as quantum yield, thermal stability, and / or photostability. The quantum dots may be encapsulated, for example, to reduce the toxicity of the quantum dots. As those skilled in the art will appreciate, many encapsulants, such as silanes or metal oxides, are contemplated.

[0015] The optical properties of quantum dots can be affected by their particle size, chemical composition, and / or surface composition and can be determined by appropriate optical tests available in the art. The ability to tune nanocrystal size, for example, between about 1 nm and about 15 nm, allows for photon emission across the entire optical spectrum, providing a wide variety of color rendering properties.

[0016] A "ligand," in embodiments, refers to a compound or molecule that can interact with one surface of a nanostructure, for example, through a covalent, ionic, van der Waals, dative or coordination bond, or other molecular interaction with the surface of the nanostructure. In some examples, the ligand may interact through a covalent, ionic, or dative bond.

[0017] "Ligand corona" refers to, for example, a state in which multiple ligands are bound to a luminescent nanostructure, and the nanostructure is substantially surrounded by ligands, for example, a state in which more than 50% of the nanostructure is surrounded by ligands.

[0018] "Quantum yield" refers to, for example, the ratio of photon emission rate to photon absorption rate in a photoluminescent sample.

[0019] "Emission wavelength peak" refers to, for example, the wavelength that exhibits an emission maximum in an emission spectrum. The emission maximum may be a local maximum and / or a global maximum.

[0020] As used herein, the term "Michael donor" refers to a nucleophile that can undergo a Michael addition reaction with a Michael acceptor. Suitable compounds include those with a thiol or amino functionality.

[0021] As used herein, the term "Michael acceptor" refers to a compound having an unsaturated electrophilic group (alkene), which may generally be an α,β-unsaturated carbonyl group.

[0022] The terms "Michael reaction," "Michael addition," "Michael addition reaction," and the like refer to the reaction of a Michael donor with a Michael acceptor to form a donor carbon bond to the β-carbon of the acceptor to produce a Michael adduct. This term includes the aza-Michael reaction (nitrogen nucleophiles), the oxa-Michael reaction (oxygen nucleophiles), and the thia-Michael reaction (sulfur nucleophiles).

[0023] The terms "halo" or "halogen," as used herein alone or as part of another group, refer to -Cl, -F, -Br, or -I.

[0024] The term "nitro" as used herein alone or as part of another group refers to --NO.sub.2.

[0025] The term "cyano" as used herein alone or as part of another group refers to --CN.

[0026] The term "hydroxy" as used herein alone or as part of another group refers to --OH.

[0027] The term "phenoxy," as used herein alone or as part of another group, refers to an oxygen group attached to a phenyl group, i.e., a C6 aryl. The term phenoxy includes phenoxy groups substituted at any position on the phenyl ring with one, two, or three groups selected from C1-C6 alkyl, C1-C6 alkoxy, hydroxy, halo, nitro, cyano, and amino. In some examples, the phenoxy has the following structure: In some examples, the phenoxy group has the following structure:

[0028] [ka]

[0029] The term "amino" when used alone or as part of another group refers to a group of the formula -NR a R b where R a and R b are each independently hydrogen or an alkyl group. In one example, the amino group is -NH. In another example, the amino group is an "alkylamino," i.e., R a C 1-6 R in alkyl b is an amino group where R ais C1-C4 alkyl. Examples of alkylamino groups include, but are not limited to, -N(H)CH3 and -N(H)CH2CH3. In another example, the amino group is a "dialkylamino," i.e., R a and R b are each independently an amino group which is a C1-C6 alkyl group. a and R b are each independently a C1-C4 alkyl group. Exemplary dialkylamino groups include, but are not limited to, -N(CH3)2 and -N(CH3)CH2CH(CH3)2.

[0030] The term "alkyl" as used herein alone or as part of another group refers to a straight- or branched-chain aliphatic hydrocarbon monovalent radical containing 1 to 12 carbon atoms, i.e., C-C 12 It refers to alkyl or a specified number of carbon atoms (e.g., C1-C3 alkyl (methyl, ethyl, propyl, isopropyl, etc.), C1-C4 alkyl (methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, etc.), and the like. In some instances, alkyl is a straight chain alkyl. In other instances, alkyl is a branched chain alkyl. In some instances, alkyl is a C1-C8 alkyl. In other instances, alkyl is a C1-C6 alkyl. In other instances, alkyl is a C1-C4 alkyl. In other instances, alkyl is a C1-C3 alkyl. For example, C1-C 12 Alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, iso-butyl, 3-pentyl, hexyl, heptyl, octyl, nonyl, and decyl. The term alkyl also includes alkyl groups substituted with one, two, or three groups selected from C1-C6 alkyl, C1-C6 alkoxy, hydroxy, halo, nitro, cyano, and amino.

[0031] The term "alkylene" refers to a divalent radical corresponding to the monovalent alkyl group defined above. In certain instances, the alkylene corresponds to any of the list of alkyl groups given above.

[0032] The term "cycloalkyl" as used herein alone or as part of another group refers to saturated and partially unsaturated (e.g., containing one or two double bonds), monocyclic, bicyclic, or tricyclic aliphatic hydrocarbon monovalent radicals containing from 3 to 12 carbon atoms, i.e., C-C 12 It refers to a cyclic alkyl group, or a group having a specified number of carbon atoms (e.g., a C3-C6 cyclic alkyl group), including cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. In some instances, the cycloalkyl is bicyclic, i.e., having two rings. In other instances, the cycloalkyl is monocyclic, i.e., having one ring. In other instances, the cycloalkyl is a C3-C8 cycloalkyl. In other instances, the cycloalkyl is a C3-C6 cycloalkyl. In other instances, the cycloalkyl is a C5 cycloalkyl, i.e., cyclopentyl. In other instances, the cycloalkyl is a C6 cycloalkyl, i.e., cyclohexyl. Examples include C3-C 12 Cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, decalin, adamantyl, and cyclohexenyl. The term cyclic alkyl also includes cyclic alkyl groups substituted with one, two, or three groups selected from C1-C6 alkyl, C1-C6 alkoxy, hydroxy, halogen, nitro, cyano, and amino. In one example, the cycloalkyl is bicyclo[2.2.1]heptanyl and substituted with three methyl groups, forming, for example, 1,7,7-trimethylbicyclo[2.2.1]heptanyl. In another example, the cycloalkyl is bicyclo[2.2.1]heptanyl and substituted with two aminomethyl groups, forming, for example, 2,3-(bisaminomethyl)bicyclo[2.2.1]heptanyl.

[0033] The term "cycloalkylene" refers to a divalent radical corresponding to the monovalent cycloalkyl group defined above. In certain instances, the cycloalkylene corresponds to any of the list of cycloalkyl groups given above.

[0034] The term "heterocyclyl," as used herein alone or as part of another group, refers to saturated and partially unsaturated (e.g., containing one or two double bonds), monocyclic, bicyclic, or tricyclic monovalent radical groups containing from 3 to 18 ring members, i.e., 3- to 18-membered heterocyclyl rings, and containing 1, 2, 3, or 4 heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. Each sulfur atom can be independently oxidized to form a sulfoxide (i.e., S(=O)) or sulfone (i.e., S(=O)). The term heterocyclyl group refers to groups in which one or more -CH- groups are replaced by one or more -C[=O] groups, including cyclic ureido groups such as imidazolidinyl-2-one, cyclic amide groups such as pyrrolidin-2-one or piperidin-2-one, and cyclic carbamate groups such as oxazolidinyl-2-one. The term heterocyclyl also includes groups having an optionally substituted aryl group or an optionally substituted heteroaryl group bonded to the ring. In some instances, the heterocyclyl is a six-membered ring containing two nitrogen atoms, such as indoline, indolin-2-one, 2,3-dihydro-1H-pyrrolo[2,3-c]pyridine, 2,3,4,5-tetrahydro-1H-benzo[d]azepine, or 1,3,4,5-tetrahydro-2H-benzo[d]azepin-2-one. The term heterocyclyl also includes heterocyclyl groups substituted with one, two, or three groups selected from C-C alkyl, C-C alkoxy, hydroxy, halo, nitro, cyano, and amino.

[0035] The term "heterocyclylene" refers to a divalent radical corresponding to the monovalent heterocyclyl group defined above. In certain instances, the heterocyclylene corresponds to any of the list of heterocyclyl groups given above.

[0036] The term "aryl" as used herein alone or as part of another group refers to a monovalent aromatic ring system radical having from 6 to 14 carbon atoms, i.e., C6-C 14 It refers to aryl. Examples of aryl groups include, but are not limited to, phenyl (abbreviated as "Ph"), naphthyl, phenanthryl, anthracyl, indenyl, azulenyl, biphenyl, biphenylene, and fluorenyl groups. In one example, the aryl group is a phenyl or naphthyl group. In another example, the aryl group is a phenyl group. The term aryl also includes aryl groups optionally substituted with one, two, or three groups selected from C1-C6 alkyl groups, C1-C6 alkoxy groups, hydroxy groups, halo groups, nitro groups, cyano groups, and amino groups.

[0037] The term "arylene" refers to a divalent radical corresponding to the monovalent aryl group defined above. In certain instances, the arylene corresponds to any of the list of aryl groups given above.

[0038] The term "heteroaryl" as used herein alone or as part of another group refers to a monovalent radical monocyclic aromatic ring system having 5 to 6 ring members, i.e., a 5- to 6-membered heteroaryl containing 1, 2, 3, 4, or 5 heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. In one example, the heteroaryl has three heteroatoms. In another example, the heteroaryl has two heteroatoms. In another example, the heteroaryl has one heteroatom. In another example, the heteroaryl has five ring atoms, such as a furyl group, which is a five-membered heteroaryl having four carbon atoms and one oxygen atom. In another example, the heteroaryl has six ring atoms, such as a pyridyl group, which is a six-membered heteroaryl having five carbon atoms and one nitrogen atom. Examples of heteroaryl groups include, but are not limited to, thienyl, furyl, pyranyl, 2H-pyrrolyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazolyl, isothiazolyl, and isoxazolyl. In certain examples, heteroaryl is thienyl (e.g., thien-2-yl and thien-3-yl), furyl (e.g., 2-furyl and 3-furyl), pyrrolyl (e.g., 1H-pyrrol-2-yl and 1H-pyrrol-3-yl), imidazolyl (e.g., 2H-imidazol-2-yl and 2H-imidazol-4-yl), pyrazolyl (e.g., 1H-pyrazol-3-yl, 1H-pyrazol-4-yl, 1H-pyrazol-5-yl), pyridyl (e.g., pyridin-2-yl, pyridin-3-yl, pyridin-4-yl), pyrimidinyl (e.g., The heteroaryl is selected from the group consisting of pyrimidin-2-yl, pyrimidin-4-yl, and pyrimidin-5-yl, thiazolyl (e.g., thiazol-2-yl, thiazol-4-yl, and thiazol-5-yl), isothiazolyl (e.g., isothiazol-3-yl, isothiazol-4-yl, and isothiazol-5-yl), oxazolyl (e.g., oxazol-2-yl, oxazol-4-yl, and oxazol-5-yl), and isoxazolyl (e.g., isoxazol-3-yl, isoxazol-4-yl, and isoxazol-5-yl). The term heteroaryl also includes N-oxides. For example, N-oxides include, but are not limited to, pyridyl N-oxides.The term heteroaryl group also includes heteroaryl groups optionally substituted with one, two, or three substituents selected from C1-C6 alkyl, C1-C6 alkoxy, hydroxy, halogen, nitro, cyano, and amino.

[0039] The term "polyalkyleneiminyl," as used herein alone or as part of another group, refers to a linear or branched polymer that includes -(amino)-(C-C alkyl)-(C-C alkyl) groups as repeat units. In another example, a polyalkyleneiminyl is a linear polymer having the formula:

[0040] [ka]

[0041] where n and m are each independently an integer from 1 to 5000. In another example, the polyalkyleneiminyl is a branched polymer, such as a polymer comprising the following fragment:

[0042] [ka]

[0043] where (*) indicates the point of attachment to additional optionally branched (amino)ethyl repeat units. In another example, the molecular weight (MW) of the polyalkyleneiminyl is from about 1,000 to about 250,000.

[0044] The term "polyalkylene glycol," as used herein alone or as part of another group, refers to a linear or branched polymer chain of repeating -(hydroxy)-(C2-C6 alkyl) units. In some examples, one or more C2-C6 alkyl groups may be substituted with one or two C1-C4 alkyl groups. In another example, the polyalkylene glycol is a linear polymer having the formula:

[0045] [ka]

[0046] Here, o is an integer between 1 and 5000.

[0047] "-(C 1-6 "(C-C alkylene)(C-C cycloalkylene)(C-C alkylene)-" refers to a structure in which a C-C alkyl group is substituted with a C-C cycloalkyl group, which is in turn substituted with a C-C alkyl group, and there is an additional point of attachment to the C-C alkyl group. In some examples, -(C-C alkylene)(C-C cycloalkylene)(C-C alkylene)- has the following structure:

[0048] [ka]

[0049] In some examples, -(C-C alkylene)(C-C cycloalkylene)(C-C alkylene)- is further substituted with an additional group A, A-(C-C alkylene)(C-C cycloalkylene)(C-C alkylene)-. In some examples, A is an amino group or an -SH group. In some examples, A-(C-C alkylene)(C-C cycloalkylene)(C-C alkylene)- has the following structure:

[0050] [ka]

[0051] As used herein, the term "-(C1-C6 alkylene)(4- to 7-membered heterocyclylene)(C1-C6 alkylene)-" refers to a C1-C6 alkyl group substituted with a 4- to 7-membered heterocyclyl group, which is itself substituted with a C1-C6 alkyl group, which itself contains an additional point of attachment. In one example, -(C1-C6 alkylene)(4- to 7-membered heterocyclylene)(C1-C6 alkylene)- has the following structure:

[0052] [ka]

[0053] In some examples, -(C1-C6 alkylene)(4- to 7-membered heterocyclylene)(C1-C6 alkylene)- is further substituted with an additional group A to form A-(C1-C6 alkylene)(4- to 7-membered heterocyclylene)(C1-C6 alkylene)-. In some examples, A is an amino group or an -SH group. As an example, A-(C1-C6 alkylene)(4- to 7-membered heterocyclylene)(C1-C6 alkylene)- has the following structure:

[0054] [ka]

[0055] "-(C1-C6 alkylene)(C6-C 14 "(C1-C6 alkylene)-" means that the C1-C6 alkyl group is C6-C 14 It refers to a structure substituted with an aryl group, which is further substituted with a C1-C6 alkyl group, and where there is an additional point of attachment to the alkyl group. In one example, -(C1-C6 alkylene)(C6-C 14 Arylene)(C1-C6 alkylene)- has the following structure:

[0056] [ka]

[0057] In some examples, -(C1-C6 alkylene)(C6-C 14 arylene)(C1-C6 alkylene)- is further substituted with an additional group A, such that A-(C1-C6 alkylene)(C6-C 14 In some instances, A is an amino group or an -SH group. In some instances, A-(C-C alkylene)(C-C 14 Arylene)(C1-C6 alkylene)- has the following structure:

[0058] [ka]

[0059] As used herein, "-(C3-C8 cycloalkylene)(C1-C6 alkylene)" refers to a C3-C8 cycloalkyl substituted with a C1-C6 alkyl. "(C3-C8 cyclic alkylene)-" refers to a structure in which a C3-C8 cyclic alkyl group is attached as a substituent, which is further substituted with a C1-C6 alkyl group, and the C1-C6 alkyl group itself has an additional point of attachment. In one example, -(C3-C8 cycloalkylene)(C1-C6 alkylene)(C3-C8 cycloalkylene)- has the following structure:

[0060] [ka]

[0061] In some examples, -(C3-C8 cycloalkylene)(C1-C6 alkylene)(C3-C8 cycloalkylene)- is further substituted with an additional group A to form A-(C3-C8 cycloalkylene)(C1-C6 alkylene)(C3-C8 cycloalkylene)-. In some examples, A is an amino group or an -SH group. In one example, A-(C3-C8 cycloalkylene)(C1-C6 alkylene)(C3-C8 cycloalkylene)- has the following structure:

[0062] [ka]

[0063] "-(C1-C6 alkylene)(4-7 membered heterocyclylene)-" refers to a 4-7 membered heterocyclyl substituted with a C1-C6 alkyl, where the C1-C6 alkyl itself has an additional point of attachment. In some examples, the -(C1-C6 alkylene)(4-7 membered heterocyclyl)- is further substituted with an additional group A to form A-(C1-C6 alkylene)(4-7 membered heterocyclylene)-. In some examples, A is an amino group or an -SH group. In one example, A-[C1-C6 alkylene-(4-7 membered heterocyclylene)] has the following structure:

[0064] [ka]

[0065] "-(C1-C 12 "Alkylene)-" refers to a C-C alkylene having an additional point of attachment thereto. 12 It refers to alkyl. In some examples, it is -(C1-C6 alkylene)-, having the following structure:

[0066] [ka]

[0067] In some instances, R 1 Regarding -(C1-C 12 alkylene)- is further substituted with an additional group A, A-(C-C 12 In some examples, A is an amino group or an -SH group. In some examples, A is A-(C1-C6 alkylene)-, for example having the following structure:

[0068] [ka]

[0069] I. Compound The present disclosure provides compounds (also called adducts) that can coordinate to luminescent nanostructures. For example, these compounds are L-type ligands, i.e., Lewis bases, that donate two electrons upon coordination by forming a coordinate bond with the nanostructure. In some instances, when a compound coordinates to a nanostructure, the coordination may result in some structural change to the compound. For example, the compound may lose a proton that was bonded to a coordinating atom. Thus, reference herein to a compound or adduct that binds to a nanostructure may also include compounds (e.g., deprotonated forms of the compound) with structural changes (which may not be shown) that occur upon coordination beyond the coordinate bond.

[0070] The present disclosure provides compounds having formula (I): [ka]

[0071] where: Y is -NH- or -S-; R 1 teeth, (i) Z-(C1-C6 alkylene)(C3-C8 cycloalkylene)(C1-C6 alkylene)-, (ii) Z-(C1-C6-alkylene)(4- to 7-membered heterocyclylene)(C1-C6-alkylene)-, (iii) Z-(C1-C6-alkylene)(C6-C 14 -arylene)(C1-C6-alkylene)-, (iv) Z-(C3-C8 cycloalkylene)(C1-C6 alkylene)(C3-C8 cycloalkylene)-, (v) polyalkyleneiminyl, and (vi) Z-(C 1-12 alkylene)-, or Y is absent and R 1 (vii) Z-(C1-C6 alkylene)(4- to 7-membered heterocyclylene)-, wherein the nitrogen atom in the heterocyclylene is in the R1 Given the connection points of Z is an amino group or -SH; R 3 is selected from the group consisting of hydrogen and C1-C6 alkyl; R 2 teeth, (i) C substituted with 0, 1, 2, or 3 groups independently selected from a C-C alkyl group, a C-C alkoxy group, a phenoxy group, an amino group, a halogen atom, a nitro group, a cyano group, and a hydroxy group. 1-12 alkyl groups, (ii) C3-C8 cycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from C1-C4 alkyl, C1-C6 alkoxy, amino, halogen, nitro, cyano, and hydroxy; and (iii) Polyalkylene glycols in which 0 or 1 or more units of the polyalkylene glycol chain are substituted with 1 or 2 C1-C4 alkyl groups; or selected from the group consisting of: R 2 (iv)C 1-12 Alkylene methacrylate or C 1-12 alkylene methacrylamide, and R 3 is hydrogen, and C 1-12 the alkylene is substituted with zero, one, or more groups independently selected from C1-C4 alkyl, C1-C6 alkoxy, phenoxy, amino, halo, nitro, cyano, and hydroxy; X is —NH— or —O—.

[0072] In some examples, Z is an amino group and Y is -NH-. 1 is (amino)(C-C alkylene)(C-C cycloalkylene)(C-C alkylene)-. In some examples, R 1 teeth:

[0073] [ka] is.

[0074] In some instances, R 1 is (amino)(C1-C6 alkylene)(4- to 7-membered heterocyclylene)(C1-C6 alkylene)-. In some examples, R 1 teeth:

[0075] [ka] is.

[0076] In some instances, R 1 (amino)(C1-C6 alkylene)(C6-C 14 arylene)(C1-C6 alkylene)-. In some examples, R 1 teeth:

[0077] [ka] is.

[0078] In some instances, R 1 is (amino)(C-C cycloalkylene)(C-C alkylene)(C-C cycloalkylene)-. In some examples, R 1 teeth:

[0079] [ka] is.

[0080] In some instances, R 1 (amino)(C 1-6 alkylene)(4- to 7-membered heterocyclylene) group, Y is absent, and a nitrogen atom in the heterocyclylene group is bonded to the carbon atom that is β-positioned relative to the carbonyl group in formula (I) by R 1 provides a connection point for

[0081] In some instances, Y is absent and R 1 teeth: [ka] is.

[0082] In some instances, R 1 is polyalkyleneiminyl. In some instances, R 1 is polyethyleneiminyl. In some instances, R 1 teeth:

[0083] [ka] is.

[0084] In some instances, R 2 is a C1-C substituted with 0, 1, 2, or 3 groups selected from C1-C4 alkyl, C1-C6 alkoxy, phenoxy, amino, halo, nitro, cyano, and hydroxy. 12 In some instances, R 2 is selected from the following group:

[0085] [ka]

[0086] In some instances, R 2 is C-C cycloalkyl substituted with zero, one, two, or three groups selected from C-C alkyl, C-C alkoxy, amino, halogen, nitro, cyano, and hydroxy. 2 teeth:

[0087] [ka] is.

[0088] In some instances, R 2 is a polyalkylene glycol. In some instances, R 2 is polyethylene glycol. In some instances, R 2contains a hydroxyl group. In some examples, X is —NH—.

[0089] In some examples, X is -O-. In some examples, R 3 is hydrogen. In some instances, R 3 is a methyl group. In some instances, R 2 is C 1-12 Alkylene methacrylate or C 1-12 alkylene methacrylamide, R 3 is hydrogen, where C 1-12 The alkylene is substituted with zero, one, or more groups independently selected from C1-C4 alkyl, C1-C6 alkoxy, phenoxy, amino, halogen, nitro, cyano, and hydroxy. 3 is hydrogen and R 2 teeth:

[0090] [ka] is.

[0091] In some examples, the compound is selected from the list in Table 1.

[0092] [Table 1-1]

[0093] [Table 1-2]

[0094] [Table 1-3]

[0095] [Table 1-4]

[0096] Table 1-5

[0097] Table 1-6

[0098] Table 1-7

[0099] Table 1-8

[0100] Table 1-9

[0101] Table 1-10

[0102] Table 1-11

[0103] Table 1-12

[0104] Table 1-13

[0105] Table 1-14

[0106] [Table 1-15]

[0107] [Table 1-12]

[0108] II. Particles The luminescent nanostructures used in embodiments of the present invention can be fabricated from any suitable material, preferably inorganic, and more preferably inorganic conductive or semiconducting materials. Suitable semiconducting materials include any type of semiconductor, including II-VI, III-V, IV-VI, and IV semiconductors. Suitable semiconductor materials include, but are not limited to, Si, Ge, Sn, Se, Te, B, C (including diamond), P, BN, BP, BAs, AlN, AlP, AlAs, AlSb, GaN, GaP, GaAs, GaSb, InN, InP, InAs, InSb, ZnO, ZnS, ZnSe, ZnTe, CdS, CdSe, CdSeZn, CdTe, HgS, HgSe, HgTe, BeS, BeSe, BeTe, MgS, MgSe, GeS, GeSe, GeTe, SnS, SnSe, SnTe, PbO, PbS, PbSe, PbTe, CuF, CuCl, CuBr, CuI, SiN, GeN, AlO, AlCO, and combinations thereof.

[0109] In some examples, the core is a II-VI nanocrystal selected from the group consisting of ZnO, ZnSe, ZnS, ZnTe, CdO, CdSe, CdS, CdTe, HgO, HgSe, HgS, and HgTe.

[0110] Although II-VI nanostructures, such as CdSe and CdS quantum dots, can exhibit desirable luminescence behavior, issues such as the toxicity of cadmium limit the applications in which such nanostructures can be used. Therefore, less toxic alternatives with favorable luminescence properties are highly desirable. III-V nanostructures in general, and InP-based nanostructures in particular, offer the most popular alternative to cadmium-based materials due to their compatible luminescence range. AgInGaS (AIGS) nanostructures are also a less toxic alternative.

[0111] In some examples, the nanostructures are cadmium-free. As used herein, "cadmium-free" refers to nanostructures containing less than 100 ppm cadmium by weight. Restriction of Hazardous Substances (RoHS) compliance defines raw, homogeneous precursor materials as containing no more than 0.01% by weight (100 ppm) of cadmium. The cadmium level in cadmium-free nanostructures is limited by the trace metal concentration in the precursor material. The trace metal (including cadmium) concentration in cadmium-free nanostructure precursor materials can be measured at parts per billion (ppb) levels by inductively coupled plasma mass spectrometry (ICP-MS). In some examples, "cadmium-free" nanostructures contain less than about 50 ppm, less than about 20 ppm, less than about 10 ppm, or less than about 1 ppm of cadmium.

[0112] Examples of materials for producing the shell of a core-shell nanostructure include, but are not limited to, Si, Ge, Sn, Se, Te, B, C (including diamond), P, Co, Au, BN, BP, BAs, AlN, AlP, AlAs, AlSb, GaN, GaP, GaAs, GaS, GaSb, InN, InP, InAs, InSb, GaSb, ZnO, ZnS, ZnSe, ZnTe, CdS, CdSe, CdSeZn, CdTe, HgS, HgSe, HgTe, BeS, BeSe, BeTe, MgS, MgSe, GeS, GeSe, GeTe, SnS, SnSe, SnTe, PbO, PbS, PbSe, PbTe, CuF, CuCl, CuBr, CuI, SiN, GeN, AlO, AlCO, and combinations thereof.

[0113] Examples of core / shell luminescent nanostructures include, but are not limited to, CdSe / ZnSe, InP / ZnSe, InP / ZnSe / ZnS, and AgInGaS / GaS (represented as core / shell).

[0114] In some examples, luminescent nanostructures are synthesized in the presence of at least one compound that forms ligands on the structure surface. After synthesis, the ligands on the nanostructure surface can be exchanged for different ligands with other desirable properties. The ligands can, for example, increase the miscibility of the nanostructures in a solvent or polymer (e.g., disperse the nanostructures throughout the composition so they do not aggregate), increase the quantum yield of the nanostructures (e.g., protect the nanostructures from degradation due to exposure to environmental conditions), and / or preserve the luminescence of the nanostructures (e.g., when the nanostructures are incorporated into a UV-curable monomer).

[0115] Ligands suitable for use in the synthesis of luminescent nanostructures are known to those skilled in the art. In some examples, the ligand is a fatty acid selected from the group consisting of lauric acid, caproic acid, myristic acid, palmitic acid, stearic acid, and oleic acid. In some examples, the ligand is an organophosphine or organophosphine oxide selected from trioctylphosphine oxide (TOPO), trioctylphosphine (TOP), diphenylphosphine (DPP), triphenylphosphine oxide, and tributylphosphine oxide. In some examples, the ligand is an amine selected from the group consisting of dodecylamine, oleylamine, hexadecylamine, dioctylamine, and octadecylamine. In some examples, the ligand is oleic acid.

[0116] In some examples, the nanostructures comprise Ag, In, Ga, and S (AIGS). In some examples, the nanostructures have a peak emission wavelength in the range of 480 to 545 nanometers. In some examples, at least about 80% of the emission is band edge emission. The quantum yield of the luminescent nanostructures can be greater than any of 0.7, 0.8, 0.9, 0.95, or 0.99.

[0117] In some examples herein, particles are provided that include a luminescent nanostructure and a ligand, wherein the ligand includes at least one compound represented by formula (I).

[0118] In some examples, the particle includes a second ligand attached to the nanostructure, where the second ligand is a compound according to Formula (I) and is different from the first ligand.

[0119] In some examples, the luminescent nanostructures include Si, Ge, Sn, Se, Te, B, C, P, BN, BP, BAs, AlN, AlP, AlAs, AlSb, AgInS, AgGaS, AgInGaS, GaN, GaP, GaAs, GaSb, InN, InP, InAs, InSb, ZnO, ZnS, ZnSe, ZnTe, CdS, CdSe, CdSeZn, CdTe, HgS, HgSe, HgTe, BeS, BeSe, BeTe, MgS, MgSe, GeS, GeSe, GeTe, SnS, SnSe, SnTe, PbO, PbS, PbSe, PbTe, CuF, CuCl, CuBr, CuI, SiN, GeN, AlO, AlCO, or a combination thereof. In some examples, the luminescent nanostructures have a core-shell structure. In some such examples, the core comprises AgInGaS and the shell comprises GaS.

[0120] The particles in some examples can be made by: two of: a Michael acceptor compound, wherein the Michael acceptor compound comprises an acrylate group, a methacrylate group, an acrylamide group, or a methacrylamide group; a Michael donor compound, wherein the Michael donor compound is selected from a diamine, a dithiol, or a compound having an amine group and a thiol group, and wherein a Michael reaction between the Michael donor compound and the Michael acceptor compound forms an adduct; and a population of luminescent nanostructures; are mixed to form a mixture, and a third of (i) through (iii) is added to the mixture, wherein a Michael reaction between the Michael donor and the Michael acceptor compound forms an adduct, wherein particles comprise luminescent nanostructures and a ligand, and wherein the ligand comprises the adduct.

[0121] In some examples, the particles are generated by mixing a population of nanostructures with ex-situ synthesized ligands. In some examples, to generate the particles, the population of luminescent nanostructures is mixed with ligand precursors (e.g., Michael donors and Michael acceptors) to form the ligands in situ. The precursors may be added to the population of nanostructures in any order.

[0122] Thus, in some instances, (i) and (ii) are first mixed to form the adduct, and then (iii) is added to the mixture. This may be referred to herein as ex-situ generation of the adduct or ligand. In other instances, (i) or (ii) is first mixed with (iii), and then the other of (i) and (ii) is added to the mixture. The ligand / adduct is generated in the presence of the luminescent nanostructure, which may be referred to herein as in-situ ligand / adduct formation.

[0123] Thus, the present disclosure provides different methods for producing particle populations, as summarized in aspects P37-P39 below. Each method offers different advantages. The choice of method may depend on the desired combination of quantum dot system and one or more ligands.

[0124] Regarding embodiment P37, nanostructures and a Michael donor compound are mixed, and then a Michael acceptor compound is added to the mixture. Initially, the quantum dot surface is covered with a native ligand, such as oleylamine (OAm). By adding the Michael donor compound first, the free amine concentration is maximized, allowing for more efficient replacement of OAm. As a result, this method may result in a higher degree of ligand exchange (i.e., complete replacement of OAm with a new ligand) compared to similar approaches.

[0125] Regarding embodiment P38, the nanostructures and Michael acceptor compound are mixed together, and then the Michael donor compound is added to the mixture. If the native ligand (e.g., OAm) is too strongly bound to the quantum dot surface, it may be necessary to add the Michael acceptor compound first to displace it. Excess Michael acceptor compound will first react sacrificially with OAm to form a non-binding adduct. Removal of the OAm leaves vacant sites on the quantum dot surface to which new ligands can be attached.

[0126] Regarding embodiment P39, the Michael donor compound and the Michael acceptor compound are mixed together, and then the nanostructures are added to the mixture. The advantage of this method is its simplicity and robustness. Here, the Michael donor and the Michael acceptor compound react first to generate a distinct ligand species. This ligand species can then displace the native ligand through a direct ligand exchange reaction. This method has fewer potential side reactions and therefore fewer variables.

[0127] Each Michael donor compound herein is a compound having an amine group and a thiol group. The Michael donor compound can be selected from diamines, dithiols, or monoamines and monothiols. Thiol groups are often more reactive toward Michael addition, and diamines of dithiols may be preferred depending on the type of quantum dot. However, as discussed below, the group can be selected more generally depending on the type of nanoparticle. For example, amines can bind strongly to the surface of AIGS quantum dots, and thiols can bind strongly to the surface of ZnSe, ZnS, CdS nanostructures, and the like.

[0128] In some instances, the most preferred structural units of the Michael donor compound are diamine or dithiol structures. These units drive the Michael addition reaction while leaving free amine or thiol groups available for binding to the quantum dot surface. In these and other instances, the remaining chemical structure of the Michael donor compound may vary.

[0129] The Michael acceptor compound is selected to be compatible with the Michael addition reaction and to provide good solubility in the target solvent. For the first condition, the presence of a double bond and its adjacent XC=O group are important, as they activate the double bond and act as an efficient Michael acceptor. Thus, X can be O or NH. For the second condition, R 2 and R 3R may have chemical properties that ensure that the final ligand exhibits good solubility in the target solvent system. The specific design rules depend on the solvent properties. For example, in more polar solvents (e.g., acrylate monomer formulations), R may be chosen to impart relatively high solubility to the quantum dots. 2 or R 3 contains polar subunits (e.g., ether linkages and hydroxyl groups).

[0130] In some examples, the Michael donor compound is a compound of formula (II): [ka] Additionally, the Michael acceptor compound is a compound represented by formula (III):

[0131] [ka] The adduct also conforms to formula (I):

[0132] [ka]

[0133] where: Y is -NH- or -S-, and R 1 teeth, (i) Z-(C1-C6 alkylene)(C3-C8 cycloalkylene)(C1-C6 alkylene)-, (ii) Z-(C1-C6-alkylene)(4- to 7-membered heterocyclylene)(C1-C6-alkylene)-, (iii) Z-(C1-C6-alkylene)(C6-C 14 -arylene)(C1-C6-alkylene)-, (iv) Z-(C3-C8 cycloalkylene)(C1-C6 alkylene)(C3-C8 cycloalkylene)-, (v) polyalkyleneiminyl, and (vi) Z-(C 1-12alkylene)-, or Y is absent and R 1 (vii) Z-(C1-C6 alkylene)(4- to 7-membered heterocyclylene)-, wherein the nitrogen atom in the heterocyclylene is in the R 1 Given the connection points of Z is an amino group or -SH; R 3 is selected from the group consisting of hydrogen and C1-C6 alkyl; R 2 teeth, (i) C substituted with 0, 1, 2, or 3 groups independently selected from a C-C alkyl group, a C-C alkoxy group, a phenoxy group, an amino group, a halogen atom, a nitro group, a cyano group, and a hydroxy group. 1-12 alkyl groups, (ii) C3-C8 cycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from C1-C4 alkyl, C1-C6 alkoxy, amino, halogen, nitro, cyano, and hydroxy; and (iii) Polyalkylene glycols in which 0 or 1 or more units of the polyalkylene glycol chain are substituted with 1 or 2 C1-C4 alkyl groups; or selected from the group consisting of: R 2 (iv)C 1-12 Alkylene methacrylate or C 1-12 alkylene methacrylamide, and R 3 is hydrogen, C 1-12 the alkylene is substituted with zero, one, or more groups independently selected from C1-C4 alkyl, C1-C6 alkoxy, phenoxy, amino, halo, nitro, cyano, and hydroxy; X is —NH— or —O—.

[0134] The reader should be aware that R 1 Note that the R and Z groups are shown. 1(ii) to (vii) are R 1 This is a Michael addition reaction similar to (i) of formula (I). Z in formula (I) or formula (II) affects the reactivity of the Michael donor. 2 (ii) to (iv) are R 2 This is a Michael addition reaction similar to (i) above.

[0135] III. Compositions, Films, Devices, and Applications Some examples are given below: A composition comprising: (a) particles comprising luminescent nanostructures and a ligand; and (b) a carrier, wherein the ligand comprises at least one compound according to Formula (I).

[0136] In some examples, the following compositions are given: A composition comprising: (a) particles comprising luminescent nanostructures and a ligand; and (b) a carrier comprising a curable acrylate monomer, wherein the ligand comprises one or more acrylate, methacrylate, acrylamide, or methacrylamide groups that are crosslinkable with the acrylate monomer of the carrier upon curing.

[0137] Additionally, the following compositions are provided: A composition comprising: (a) particles comprising a luminescent nanostructure and a ligand; and (b) a carrier comprising a cured acrylate polymer, wherein the ligand is crosslinked with the acrylate polymer of the carrier. In some such cases, the ligand comprises one or more acrylate, methacrylate, acrylamide, or methacrylamide groups, which upon curing crosslink with the acrylate of the carrier.

[0138] Additionally, a method of making the composition is provided, comprising: (a) (i) mixing particles comprising luminescent nanostructures and ligands comprising one or more of an acrylate group, a methacrylate group, an acrylamide group, or a methacrylamide group, and (ii) a carrier comprising an acrylate monomer; and (b) curing at least a portion of the acrylate monomer of the carrier to form an acrylate polymer crosslinked with the ligand.

[0139] In some examples, the carrier is liquid and includes at least one additive. In some examples, the suitable additive is a photoinitiator. In some examples, the additive is triphenyl phosphite, tetra[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]pentaerythritol, isopropyl thioxanthone, 2,4-diethyl thioxanthone, or 3-(trimethoxysilyl)propyl acrylate.

[0140] In some instances, the carrier is a liquid.

[0141] In some examples, the carrier comprises a crosslinkable acrylate monomer. Examples of the acrylate monomer include, but are not limited to, methyl (meth)acrylate, ethylene glycol phenyl (meth)acrylate, di(ethylene glycol) methyl ether (meth)acrylate, diethylene glycol monoethyl ether acrylate, ethylene glycol methyl ether (meth)acrylate, 1,3-butylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, and 1,6-hexanediol diacrylate, isobornyl acrylate, 2-phenoxyethyl acrylate, 4-hydroxybutyl acrylate, 2-hydroxy-3-phenoxypropyl acrylate, or a combination thereof. In some examples, the acrylate monomer is isobornyl acrylate, 2-phenoxyethyl acrylate, 4-hydroxybutyl acrylate, 2-hydroxy-3-phenoxypropyl acrylate, or a combination thereof.

[0142] In some instances, the liquid carrier additionally comprises a solvent.

[0143] In some instances, the carrier is solid. In some instances, a solid carrier can be formed from a liquid carrier. Converting the liquid carrier to a solid carrier can include curing the monomers in the carrier to form a polymer, for example, by UV curing or thermal curing.

[0144] In some examples, the carrier comprises a cross-linked acrylate polymer. Examples of cross-linked acrylates include poly(methyl (meth)acrylate), polyethylene glycol phenyl (meth)acrylate, poly(di(ethylene glycol) methyl ether (meth)acrylate), poly(diethylene glycol monoethyl ether acrylate), poly(ethylene glycol methyl ether (meth)acrylate), poly(1,3-butylene glycol di(meth)acrylate), poly(polyethylene glycol di(meth)acrylate), poly(1,6-hexanediol diacrylate), poly( isobornyl acrylate), poly(tetrahydrofurfuryl acrylate), poly(lauryl acrylate), poly(tricyclodecane dimethanol diacrylate), poly(glycerol triacrylate), poly(1,1,1-trimethylolpropane triacrylate), poly(pentaerythritol tetraacrylate), poly(bistrimethylolpropane triacrylate), poly(dipentaerythritol pentaacrylate), poly(pentaerythritol triacrylate), poly(pentaerythritol tetraacrylate) acrylate), poly(trimethylolpropane triacrylate), poly(dipentaerythritol pentaacrylate ester), poly(isobornyl methacrylate), poly(tetrahydrofurfuryl methacrylate), poly(lauryl methacrylate), poly(tricyclodecane dimethanol dimethacrylate), poly(glycerol trimethacrylate), poly(1,1,1-trimethylolpropane trimethacrylate), poly(pentaerythritol tetramethacrylate), poly(bistrimethylolpropane tetramethacrylate). methacrylate), poly(dipentaerythritol pentamethacrylate), poly(pentaerythritol trimethacrylate), poly(pentaerythritol tetramethacrylate), poly(trimethylolpropane trimethacrylate), poly(dipentaerythritol pentamethacrylate ester), poly(1,6-hexanediol dimethacrylate), poly(1,4-butanediol diacrylate), poly(1,9-nonanediol diacrylate), poly(1,4-butanediol dimethacrylate), poly(1,Examples of crosslinked acrylates include, but are not limited to, poly(9-nonanediol dimethacrylate), poly(2-phenoxyethyl acrylate), poly(4-hydroxybutyl acrylate), poly(2-hydroxy-3-phenoxypropyl acrylate), or combinations thereof. In some examples, the crosslinked acrylate is poly(isobornyl acrylate), poly(2-phenoxyethyl acrylate), poly(4-hydroxybutyl acrylate), poly(2-hydroxy-3-phenoxypropyl acrylate), or combinations thereof.

[0145] In some examples, the composition including the solid carrier contains from about 70% to about 90% by weight of one or more crosslinked polymers. In some examples, the composition including the solid carrier contains from about 70% to about 85% by weight, from about 70% to about 80% by weight, from about 75% to about 90% by weight, or from about 75% to about 85% by weight, or from about 75% to about 80% by weight of one or more cured polymers.

[0146] In some examples, the composition including the solid carrier comprises particles and a crosslinked polymer, and the weight ratio of the particles to the crosslinked polymer ranges from about 1:9 to about 1:4. In some examples, the composition including the solid carrier comprises particles and a crosslinked polymer, and the weight ratio of the particles to the crosslinked polymer ranges from about 1:4 to about 1:6.

[0147] In some examples, the composition comprising the solid carrier comprises from about 10% to about 30% by weight of particles, hi some examples, the composition comprising the solid carrier comprises from about 10% to about 20% by weight of particles.

[0148] In some examples, the composition is provided as a film or layer. In some such examples, the film exhibits a photon conversion efficiency (PCE) of about 20% to about 35%, or about 25% to about 30%.

[0149] In some examples, the film thickness is 500 pm or less, 100 pm or less, or 50 pm or less. In some examples, the film thickness is about 15 pm or less.

[0150] In some examples, the film further comprises one or more barrier layers immediately adjacent to the film that have low oxygen and water vapor permeability and protect the nanostructures from degradation.

[0151] In some examples, the film does not include a barrier layer. While not intending to be bound by theory, it is believed that the ligands in the examples herein provide sufficient protection from degradation in the presence of oxygen and / or water while dispersing the nanostructures in polar solvents, resins, and / or matrices. It is believed that strong hydrogen bonds between the ligands increase the cohesive energy of the ligand corona, acting as a more efficient physical barrier against oxygen and reactive oxygen species (ROS).

[0152] In some examples, the photon conversion efficiency (PCE) of the film is about 25%. In some examples, the PCE of the film is about 5%, about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, about 40%, about 45%, or about 50%.

[0153] In some examples, the PCE of the film is about 10% to about 40%, about 15% to about 40%, about 20% to about 40%, about 25% to about 40%, about 30% to about 40%, about 35% to about 40%, about 10% to about 35%, about 15% to about 35%, about 20% to about 35%, about 25% to about 35%, about 30% to about 35%, about 10% to about 30%, about 15% to about 30%, about 20% to about 30%, about 25% to about 30%, about 10% to about 25%, about 15% to about 25%, about 20% to about 25%, about 10% to about 20%, about 15% to about 20%, or about 10% to about 15%.

[0154] In some examples, the film maintains about 95% of its PCE after 24 hours of exposure to air and 20 lux yellow light compared to the PCE value before exposure. In some examples, the film maintains about 80%, about 85%, about 90%, about 93%, about 95%, about 96%, about 97%, about 98%, or about 99% of its PCE after 24 hours of exposure to air and 20 lux yellow light compared to the PCE before exposure.

[0155] In some examples, the film maintains a PCE of about 85% to about 99%, about 90% to about 99%, about 93% to about 99%, or about 95% to about 97% of the pre-exposure PCE value after 24 hours of exposure to air and 20 lux yellow light.

[0156] Films according to embodiments described herein can be produced, for example, by depositing a composition comprising a liquid carrier as described herein, and then curing and / or solidifying the composition from a liquid state to a more solid-like state, for example, by UV curing and / or heating.

[0157] Depositing the composition in a liquid state can be done, for example, by printing (e.g., using inkjet printing techniques). In other examples, depositing can include extruding or spreading the composition in a liquid state before solidifying and / or curing.

[0158] Once the liquid composition solidifies and / or hardens, it can be referred to as a film or layer. As described below, such a film or layer can be referred to as a quantum dot-enhanced film (QDEF) or, in other examples, as a quantum dot color conversion (QDCC) film. Such a QDEF is, for example, a film that extends to cover all subpixels and / or pixels of a display device. On the other hand, a QDCC is, for example, composed of an array of multiple films corresponding to each light source of a display device. Thus, one film can correspond to one light source, i.e., one subpixel. In such a QDCC film, the composition can, for example, include: a first region including a first particle population; the first particle population having first luminescent nanostructures that emit light of a first color (e.g., red); and a second region including a second particle population; the second particle population having second luminescent nanostructures that emit light of a second color (e.g., green). Thus, for example, a first film in an array or a plurality of films may have a first region with a first population, and a second film in the array or a plurality of films may have a second region with a second population. Inkjet printing is useful for depositing such films. First, an array of a first type of film (e.g., having nanostructures that emit red light) may be printed, followed by an array of a second type of film (e.g., having nanostructures different from those of the first type of film and for green light emission), and optionally, one or more arrays of yet another type of film (e.g., having nanostructures different from those of the first and second types of films). Thus, such an array of films may be printed to have regions corresponding to the red, green, and blue subpixels of a display device.

[0159] In further examples, such as FIG. 9 , instead of a film such as a QDEF or QDCC film, particles with exemplary ligands are incorporated into the light source 118 itself. Such light sources can generate light by electroluminescence, whereby the nanostructures emit light as a result of an electric current applied to them. Such light sources 118, e.g., referred to as light-emitting diodes, include, for example: (a) a first electrode 102, (b) a second electrode 112, and (c) a layer 108 disposed between the first and second electrodes. In some examples not shown, the layer is in contact with one or both of the first and / or second electrodes. Layer 108 is comprised of particles in one or more examples described herein (including nanostructures with ligands in one or more examples described herein). Such layers may be referred to as light-emitting layers. Such layers may be, for example, films or layers described above, fabricated, for example, by inkjet printing. An array of such light sources can be fabricated, for example, by printing at least a layer of each light source in a manner similar to forming the array of films described above in the context of QDCC films.

[0160] As one skilled in the art will appreciate, the light source 118, in some examples, such as in Figure 9, includes one or more additional layers (104, 106, 110, 112) between the first electrode and the second electrode, such as a hole injection layer 104, a hole transport layer 106, an electron transport layer 110, and / or an electron injection layer 112. In some examples, at least one of the layers between the first electrode and the second electrode includes an organic material.

[0161] As will be understood by those skilled in the art, when a voltage is applied between the first electrode and the second electrode, holes injected from the first electrode migrate to the light-emitting layer via the hole injection layer and / or hole transport layer, and electrons injected from the second electrode migrate to the light-emitting layer via the electron transport layer, where they recombine to generate excitons.

[0162] In some examples, the light source 118 includes a substrate 114. The substrate is, for example, glass or a flexible material such as polyimide or polyethylene terephthalate. In some examples, the substrate has a thickness ranging from about 0.1 mm to about 2 mm. In some examples, the substrate is a glass substrate, a plastic substrate, a metal substrate, or a silicon substrate.

[0163] In some examples, the first electrode is disposed on a substrate. In some examples, the first electrode is a stack of conductive layers. In some examples, the first electrode is deposited as a thin film using known deposition techniques, such as sputtering or electron beam evaporation. In some examples, the first electrode is an anode or a cathode.

[0164] In some examples, the first electrode is an anode and the second electrode is a cathode. In other examples, the first electrode is a cathode and the second electrode is an anode. The first electrode and / or electrode layer may include any one of indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO), zinc oxide (ZnO), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), silver (Ag), gold (Au), or a mixture thereof. In some examples, the second electrode is a stack of conductive layers. For example, the second electrode may include a layer of silver sandwiched between two layers of ITO (ITO / Ag / ITO).

[0165] In some examples, the light source 118 further includes a hole injection layer 104. In some examples not shown, the hole injection layer 104 is deposited on the first electrode. In some examples, the hole injection layer is deposited by vacuum deposition, spin coating, printing, casting, slot-die coating, or Langmuir-Blodgett (LB) deposition.

[0166] In some examples, the hole injection layer comprises copper phthalocyanine, 4,4',4''-tris[(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4''-tris(diphenylamino)triphenylamine (TDATA), 4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine (2T-NATA), polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / polystyrenesulfonate (PEDOT / PSS), polyaniline / camphorsulfonic acid, or polyaniline / poly(4-styrenesulfonate).

[0167] In some examples, the light source 118 further includes transport layers (110 and 106) to facilitate transport of electrons and holes under the influence of an electric field generated between the first electrode 102 and the second electrode 112. In some examples, the light source 118 includes a first transport layer associated with the first electrode. In some examples, the first transport layer is a hole transport layer (and electron and / or exciton blocking layer). In some examples, the first transport layer is deposited on the first conductive layer. In some examples, the first transport layer is deposited on the hole injection layer. In some examples, the first transport layer is substantially transparent to visible light.

[0168] In some examples, the first transport layer comprises a material selected from the group consisting of an amine, a triarylamine, a thiophene, a carbazole, a phthalocyanine, a porphyrin, or a mixture thereof. In some examples, the first transport layer comprises N,N'-di(naphthalen-l-yl)-N,N'-bis(4-vinylphenyl)-4,4'-diamine, poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl))diphenylamine)], and poly(9-vinylcarbazole).

[0169] In some examples, the light source further comprises a second transport layer. In some examples, the second transport layer is an electron transport layer (and hole and / or exciton blocking layer). In some examples, the second transport layer contacts the light-emitting layer. In some examples, the second transport layer is between the light-emitting layer and the second conductive layer. In some examples, the second transport layer is transparent to visible light.

[0170] In some examples, the electron transport layer comprises at least one of zinc oxide or zinc magnesium oxide.

[0171] In examples, devices include the aforementioned compositions, e.g., film or liquid compositions. Such devices may include a light source configured to emit light at one or more wavelengths absorbed by the nanostructures. In some examples, a filter array includes a red light filter for transmitting red light, a green light filter for transmitting green light, and a blue light filter for transmitting blue light, as well as a light valve array. In other such examples, the light source is an LED including the composition or film, e.g., as a layer (e.g., a top layer) of the LED arranged to receive light generated by the LED and forward output light from the nanostructures. In this manner, each light source may be comprised of the composition or film. Such light sources are, for example, the aforementioned electroluminescent light sources. Another example of a device in which each light source has a corresponding film is, for example, an array of films arranged to receive light emitted from each of a plurality of light sources. Such a plurality or array may be provided, for example, as a layer separate from the light sources and inkjet printed, and may be referred to as the aforementioned QDCC film.

[0172] Further details of such devices are described in more detail below.

[0173] An example of a device herein is described with reference to Figures 10A and 10B. The device shown schematically in Figures 10A and 10B is a display device 402 having functional elements configured to operate together to generate and output an image. Several such functional elements are stacked and collectively referred to herein as a display stack 404. The display stack 404 may include, for example, a light source 410 configured to emit light 407 (e.g., an LED or organic LED (OLED) backlight), a light valve array 414 (e.g., a liquid crystal display (LCD) panel) for modulating the amount of light received from the light source, and a filter array 416 (e.g., a color filter array such as a red, green, and blue subpixel filter array) for determining the color of light output by the display device 402 (e.g., by each subpixel region of the device). The example film 400 may be positioned between a light source 410 and a light valve array 414 (as shown in FIG. 10A), or may be positioned between a light valve array 414 and a filter array 416 (e.g., as shown in FIG. 10B).

[0174] The display device 402 includes a light source 410 arranged to provide, for example, a backlight or edge-lit display device. The light source may be, for example, at least one of an LED, an LED array, an organic LED (OLED), an OLED array, a laser, a laser array, or a lamp. The light source may be configured to illuminate multiple pixels of the display device, or there may be multiple light sources each illuminating a single pixel. A pixel may be, for example, a subpixel or pixel of the display device. A display device typically includes multiple independently controllable pixels to display an image. The pixels may be arranged according to a pattern, for example, as an array, matrix, or grid, as will be understood by those skilled in the art. A display device capable of displaying color images typically includes multiple pixels, each pixel including multiple subpixels, for example, a pixel including a red (R), green (G), and blue (B) subpixel that together function as an RGB pixel. An additional independently controllable subpixel, for example, a white (W) subpixel, may be provided to provide an RGBW pixel.

[0175] In addition to such a light source, the display device includes a light modulator configured to modulate the light emitted by the light source to display an image. The light modulator has an array of light modulator regions that modulate the light. Each light modulator region in the array of light modulator regions corresponds to a respective pixel of the display device. Thus, for example, when looking at the viewing side of the display device to display an image to a user's eye, the perimeter of one light modulator region defines the extent of one pixel. The light source or light guide has an extent covered by the array of light modulator regions, such that each light modulator region is illuminated by a light source. The light valve array 414 described above is an example of such a light modulator.

[0176] A display device control system (not shown) is configured to control the array of light modulator regions through which the display device outputs images. Each light modulator region is independently controllable to modulate, for each pixel, the amount of light transmitted through the modulator region toward the viewer. Thus, one light modulator region can be switched to transmit less light (a darker state) than another light modulator region (a brighter state), so that, with appropriate light modulation across the array of light modulator regions (and thus pixels), the display device can display a desired image.

[0177] As those skilled in the art will appreciate, one type of light modulator uses liquid crystal (LC) molecules for light modulation. By applying an appropriate electric field to the electrodes in the light modulator region, the orientation of the LC molecules can be changed to modulate the light output by each pixel and display an image on the viewing side. An LC-type light modulator has a polarizing layer that linearly polarizes the light input to the light modulator. The polarizing layer is on a substrate (e.g., glass). On the substrate is a circuit layer connected to an array of electrodes (e.g., indium tin oxide (ITO)), each of which is electrically insulated from the others and has an extent that defines the shape and size of each pixel. On the electrodes is a layer containing LC molecules, whose LC molecules and their density in the layer are selected to provide the required rotation of linearly polarized light depending on the magnitude of the applied electric field. An alignment layer is in contact with the layer containing LC molecules and orients the LC molecules in contact with the alignment layer in a specific orientation. A separate linear polarizer layer is used to polarize the light exiting the light modulator, which is oriented, for example, to linearly polarize the light in a direction perpendicular to the polarizer layer. Above the other linear polarizer layer is a substrate (e.g., glass). There is an electrode that extends over two or more (e.g., all) pixels, sometimes called a common electrode.

[0178] Each pixel also includes a color filter between the alignment film and the separate linear polarizer layer in these examples. By appropriate selection of color filters for each pixel, an RGB pixel (of three subpixels) can be created using a red filter that transmits red light, e.g., at a wavelength of 630 nm, a green filter that transmits green light, e.g., at a wavelength of 532 nm, and a blue filter that transmits blue light, e.g., at a wavelength of 467 nm. Such an array of color filters is an example of the filter array mentioned above.

[0179] For example, a display device may have a display stack of functional elements including a light source, a QDEF, and a filter array. In these examples, there is also a light modulator. Starting from the bottom of the stack, there is a substrate (e.g., glass), a light source circuit layer on the substrate, and a plurality of LEDs as light sources connected to the circuit layer. In the example of a backlight, a plurality of LEDs are arranged, for example, as an array of LEDs superimposed by the light modulator to illuminate the light modulator.

[0180] The density and positioning of the LEDs depends at least in part on the shape and size of the display's pixels, but also on the illumination characteristics of each LED and any layers, such as diffusers or reflectors, that transmit light from the LEDs to the light modulator. In some such examples, each LED of a lighting device's multiple LEDs is configured to illuminate multiple pixels (e.g., 50-100 or even thousands) of the display device. Each of the multiple pixels can be considered a region having a so-called mini-LED configuration, and in some examples, each region is independently controllable relative to the other regions. Switching different regions separately can improve contrast, for example, by turning off one region to provide a darker black, and is sometimes referred to as "local dimming."

[0181] In other edge-lit examples, instead of an array of LEDs, there is a light guide overlaid with a light modulator, with at least one of the LEDs positioned along at least a portion of the periphery of the light guide to illuminate the light modulator through the light guide. In some such examples or other examples, a diffuser is overlaid with the light modulator. Between the LED and the light modulator may be one or more layers, such as a diffuser to distribute the light from the LED more evenly across the light modulator and / or an alignment film (e.g., a so-called brightness enhancement film (BEF)) that uses prisms to align the light from the LED with each pixel. Such diffusers and / or alignment films may also be used. Various other functional elements may be used, for example to modify the light, as will be understood by those skilled in the art. This may include, for example, a so-called dual back-effect filter (DBEF) (e.g., polarizing light for the liquid crystal light valve array and reflecting light that is not of the desired polarization for the liquid crystal light valve array back to the backlight for re-reflection towards the DBEF), the aforementioned TFE layer, a prism layer, a reflector, a partial reflector, a polarizer, a diffuser, a barrier layer, an anti-reflection material, or a collimator.

[0182] The circuit layers for the light source and the light modulator are each connected to a display device control system and configured for control of the light source and the light modulator by the display device control system to output a desired image. The circuit layer for the light modulator is configured for so-called active matrix control of the light modulator regions, for example, by using switching elements (e.g., thin film transistors (TFTs)) for each pixel and configuring each light modulator region to transmit a desired amount of light by appropriately applying electrical signals to the source and gate terminals of each TFT. The circuit layer for the light source is configured to control the light output by the LEDs, for example, by turning on certain regions of the LEDs while turning off other regions of the LEDs. Depending on the number of LEDs and their layout, the circuit layer for the light source may also include switching elements (e.g., TFTs) for active matrix control of the LEDs.

[0183] A display device control system is connected to the circuit layer and the common electrode by signal lines. The display device control system has, for example, a data input for receiving data representing one or more images for the display device to display. As one skilled in the art will appreciate, the display device control system may include circuitry for determining and applying appropriate electrical signals to the electrodes of the light modulators and the LEDs of the light source (and based on the data representing the images to be displayed).

[0184] As those skilled in the art will appreciate, the magnitude of the voltage applied between the common electrode and the electrode of a given pixel's light modulator region, and therefore the magnitude of the applied electric field, determines the rotational orientation of the LC molecules through the pixel relative to the orientation set by the alignment film and relative to the linear polarizer layer. Thus, the degree of light modulation in each light modulator region can be controlled, and thus the amount of transmitted light that is aligned with or at least partially rotated in orientation relative to the alignment film.

[0185] As will be appreciated by those skilled in the art, further types of examples are envisioned that have a light modulator combined with a light source, but that use technologies other than LC molecules for light modulation (e.g., microelectromechanical (MEM) technology or electrophoretic technology).

[0186] Rather than using a separate light modulator in combination with the lighting device, it is further contemplated that each LED of the light source corresponds to a respective pixel and can be controlled to modulate the light output of each pixel. For example, each subpixel may include a blue LED, and / or multiple subpixels may be illuminated by a single white LED, or alternatively, by green and red LEDs. By appropriately controlling each of the blue, green, and red LEDs, the color of the image output by the display device can be adjusted.

[0187] Examples of display devices as described herein may be, for example, display panels, display units, or display screens for devices such as televisions, computer monitors, tablet computing devices, laptop computing devices, mobile telecommunications devices such as smartphones, portable (e.g., mobile) devices, electronic reader devices, watches, satellite navigation devices, heads-up display devices, game consoles, flexible displays, augmented reality (XR) devices, virtual reality (VR) devices, and / or augmented reality (AR) devices.

[0188] Thus, for example, the display device may be incorporated into an apparatus comprising a display device, at least one processor, and at least one memory comprising computer program instructions, the at least one memory and the computer program including instructions operable together with the at least one processor to control a display device control system for controlling the display device to output images.

[0189] 11 shows a system diagram illustrating an example of the basic hardware architecture of a system 650, such as a laptop computing device. Note that in other implementations, some of the components shown in FIG. 11 are not present. For example, in the case of a computer monitor implementation, system storage and / or a battery may not be present. System 650 includes a display device 654, at least one processor 658 connected to, and therefore in data communication with, e.g., a display device control system 652 (e.g., according to the example above), a communication system 656, a user input system 660, a power system 662, and a system storage device 664. The display device control system is connected to, and therefore in data communication with, display device 654.

[0190] The display device control system 652 includes, for example, driver components for use in applying voltages to any of the pixels to address different such pixels. In an example, the light modulator regions of the pixels are driven using an active matrix control scheme, and the display device control system is configured to control switching elements, such as thin film transistors (TFTs), of the display device 654 via circuitry to control the pixels. The circuitry may include signal lines and control lines. For example, the display device control system 652 may include display drivers, such as a display column driver and a display row driver.

[0191] The at least one processor 658 herein may be, for example, a general-purpose processor, a microprocessor, a digital signal processor (DSP), an application-specific integrated circuit (ASIC), a field-programmable gate array (FPGA), a programmable logic element, discrete gate or transistor logic, discrete hardware components, or any suitable combination thereof configurable for the functions described herein. A processor may also be a combination of computing devices, such as a DSP and a microprocessor, multiple microprocessors, a microprocessor in conjunction with a DSP core, or any other such configuration. The processor 658 may be coupled to read information from or write information to a memory of a storage device via one or more buses. The processor 658 may additionally or alternatively include memory, such as processor registers.

[0192] The communications system 656 configures the system 650 to communicate with computing devices over, for example, a data network, a computer network such as the Internet, a local area network (LAN), a wide area network (WAN), a telecommunications network, a wired network, a wireless network, or another network. The communications system may include an input / output (I / O) interface such as a universal serial bus (USB) connection, a Bluetooth connection, or an infrared connection, or a data network interface for connecting the device to a data network such as any of the above. Content data, as described below, may be transferred to the system via the communications system.

[0193] The user input system 660 may include input devices for receiving input from a user of the system. Examples of input devices include, but are not limited to, a keyboard, roller ball, button, key, switch, pointing device, mouse, joystick, remote control, infrared detector, voice recognition system, barcode reader, scanner, video camera (possibly coupled with video processing software for detecting hand or facial gestures), motion detection device, microphone (possibly coupled with audio processing software for detecting voice commands), VR gloves, AR gloves, haptic input device, computer vision device, simultaneous localization and mapping (SLAM) device, eye tracking device, hand tracking device, or other device capable of transmitting information from a user to the device. The input device may also take the form of a touchscreen associated with the display device 654, where the user responds to prompts on the display device 654 by touch. The user may enter textual information via an input device such as a keyboard or touchscreen.

[0194] The system may also include a user output system (not shown), including, for example, an output device for providing output to a user of the system. Examples include, but are not limited to, a printing device, an audio output device including, for example, one or more speakers, headphones, earphones, an alarm, or a tactile output device. The output device may also be a connector port for connecting to one of the other output devices described, such as earphones.

[0195] The power system 662 includes, for example, power circuitry for use in transmitting and controlling the power consumed by the system. Power may be provided by a mains power source or from a battery (not shown) via the power circuitry. The power circuitry may also be used to charge the battery from the mains power source.

[0196] The storage device 664 may include memory, such as at least one volatile memory 666 and a nonvolatile memory 670, and may include non-transitory computer-readable storage media. The volatile memory may be, for example, random access memory (RAM). The non-volatile (NV) memory may be, for example, a solid-state drive (SSD) such as flash memory or read-only memory (ROM). Additional storage technologies may be used, such as magnetic media, optical media, tape media, compact discs (CDs), digital versatile discs (DVDs), Blu-rays, or other data storage media. The volatile and / or non-volatile memory may be removable or non-removable. Any of the memories may store data for controlling the system. Such data may be, for example, in the form of computer-readable and / or executable instructions, e.g., computer program instructions. Thus, the at least one memory and the computer program instructions may be operable to control, using at least one processor, a display device control system for controlling the display device 654 to output images.

[0197] In the example of FIG. 11 , volatile memory 666 stores, for example, display device data 668 representing an image to be rendered by the system. Processor 658 may send data based on display device data 668 to control system 652 to display image 675, which then outputs signals to the display device to energize pixels. Non-volatile memory 670 stores, for example, program data 672 and / or content data 674. Program data, for example, in the form of computer software, is data representing computer-executable instructions for the system to execute an application or program module for the system or a component of the system to perform a particular function or task and / or to control the component or component of the system. For example, application or program module data includes any of routines, programs, objects, components, data structures, etc. Content data, for example, is data representing user content; such content may represent any form of media, such as text, at least one image or portion thereof, at least one video or portion thereof, or at least one sound or music or portion thereof. Data representing an image or part thereof may, for example, represent the image provided by at least one pixel of a display device. Such data may include one type of content data, but may alternatively include a mixture of different types of content data, for example a movie may be represented by data including at least image data and audio data.

[0198] IV. Compound Examples Example 1: Synthesis of Michael adduct ligands from acrylate and diamine precursors. Reaction Scheme 1

[0199] [ka]

[0200] 4-Hydroxybutyl acrylate (HBA) and 1,3-bis(aminomethyl)cyclohexane (CHBMA) were mixed at room temperature in a 1:1 molar ratio to produce the Michael adduct, compound 15, as shown in Reaction Scheme 1. The conversion of the starting material to the product was confirmed by Fourier transform infrared spectroscopy (FT-IR) and proton nuclear magnetic resonance spectroscopy ( 1 The results were observed using H NMR, and are shown in Figures 1 and 2, respectively. In Figure 1, the dashed line corresponds to HBA, the dashed line corresponds to the HBA + CHBMA mixture after 1 minute, and the solid line corresponds to the mixture after 5 minutes. -1 The disappearance of the sharp peak in the range indicates the complete conversion of the initial acrylate species. In Figure 2, the solid line in the inset corresponds to the HBA / CHBMA adduct, and the dashed line corresponds to HBA.

[0201] Compounds 22 and 29 were synthesized in a similar manner, as shown in Reaction Scheme 2. Reaction Scheme 2

[0202] [ka]

[0203] As another example, the reaction of N-butylacrylamide with (1,3-bis(aminomethyl)cyclohexane) (CHBMA) produces the ligand S1 shown below. Using this ligand, a successful ligand exchange was carried out following a method similar to the above reaction in Reaction Scheme 1 (Aspect P38). This reaction produced a colloidally stable quantum dot solution.

[0204] [ka] S1: Ligand generated by the reaction of CHBMA with N-butylacrylamide.

[0205] Example 2: Ligand exchange onto quantum dots. Ligand exchange was performed on AgInGaS / GaS quantum dots, replacing the native ligand with a combination of compound 15 and compound 22. FT-IR and 1 Ligand exchange was confirmed by H NMR, as shown in Figures 3 and 4, respectively. Regarding Figure 4, the presence of bound Michael adduct is indicated by the presence of broader resonances, consistent with those seen in the spectrum of the ex-situ free adduct. Residual native oleylamine ligand is also observed. The thin dashed line in Figure 4 corresponds to the HBA / CHBMA adduct, the thin solid line corresponds to the PhEA / CHBMA adduct, and the thick solid line corresponds to quantum dots bound to a combination of these two adducts.

[0206] The ligand exchange could be carried out ex-situ after the Michael adduct ligand has been synthesized, or in-situ in the presence of the Michael adduct ligand starting material.

[0207] Example 3: Films containing quantum dots with Michael adduct ligands. The AgInGaS / GaS quantum dots were ligand-exchanged using the in-situ or ex-situ methods described in Example 2 and incorporated into a support consisting of 1,6-hexanediol diacrylate and a photoinitiator. The photoconversion efficiency (PCE) of the resulting films was then measured both pristinely and after 24 hours of exposure to air and 20 lux yellow light. The results are shown in Table 2. Films containing the Michael adduct ligand exhibited up to 96.7% retention of PCE after 24 hours of exposure to air and 20 lux yellow light.

[0208] [Table 2]

[0209] Abbreviations: IBOA = isobornyl acrylate, HOPhEA = 2-hydroxy-3-phenoxypropyl acrylate, TPP = triphenyl phosphite, ITX = isopropyl thioxanthone, DETX = 2,4-diethyl thioxanthone, TMPSA = 3-(trimethoxysilyl)propyl acrylate.

[0210] In particular, films composed of quantum dots containing the commonly used polyetheramine ligand, but without Jeffamine, maintained significantly higher initial PCEs than films containing Jeffamine-containing quantum dots. While not intending to be bound by theory, it is believed that the use of Jeffamine ligands with ether linkages bearing abstractable hydrogen groups leads to radical generation near the quantum dot surface, resulting in subsequent radical-mediated damage to the quantum dot surface. The Michael adduct ligands disclosed herein are expected to bind via the amine moiety of the ligand, forming a buffer layer between the quantum dot surface and the oxygen-containing portion of the ligand, making this problem less likely to occur. Furthermore, when a Michael adduct ligand capable of forming hydrogen bonds (e.g., when the ligand contains hydroxyl groups) is added to a quantum dot population, the strong hydrogen bonds are believed to increase the cohesive energy of the ligand corona, acting as a more efficient physical barrier against oxygen and reactive oxygen species (ROS). Figure 5 shows that when hydroxyl groups are present in the ligand shell of quantum dots (e.g., when compound 15 is the ligand), films containing the quantum dots can have higher PCEs after 24 hours of exposure to air and 20 lux yellow light.

[0211] Example 4: Acrylate film containing quantum dots with ligands bearing methacrylic groups. 1,3-Bis(aminomethyl)cyclohexane (CHBMA) and 3-(acryloyloxy)-2-hydroxypropyl methacrylate (AHPMA) were mixed in a 1:1 molar ratio at room temperature to form the Michael adduct, compound 113, as shown in Reaction Scheme 3 as "CAH."

[0212] [ka] Reaction Scheme 3

[0213] The resulting adduct was mixed with 1,6-hexanediol diacrylate (HDDA), and the mixture was cured under UV irradiation, forming cross-links between the methacrylic acid groups of CAH and the acrylic acid groups of HDDA.

[0214] The structural changes described above can be explained using a combination of NMR and FTIR spectroscopy. First, ex-situ NMR measurements of the reaction of CHBMA with AHPMA demonstrate the continued presence of methacrylate groups during ligand formation. Figure 6 shows the disappearance of resonances associated with acrylate groups (indicating complete reaction with the amine), but the persistence of peaks associated with less reactive methacrylate groups. Next, in ligand exchange involving this system as part of a mixture, the same peaks (in this case broadened) indicate the presence of CAH within the ligand shell. In Figure 7, peaks corresponding to methacrylate groups are observed. Finally, upon film curing, FTIR analysis reveals a near-quantitative attenuation of the peaks associated with the C=C bonds of AHPMA, indicating that they have formed covalent bonds with the monomer in the ink to form a polymeric matrix. In Figure 8, the features associated with the presence of methacrylate groups almost completely disappear from the film spectrum, indicating that this group has reacted with the monomer ink.

[0215] AHPMA contains both acrylate and methacrylate groups. The synthetic concept described above is similar to the "dual cure" approach used in polymer engineering and relies on the fact that acrylate groups are more reactive than methacrylate groups. As a result, this compound can be used in a planned two-step reaction scheme. The first reaction is a Michael addition reaction between the acrylate unit and the amine group on the diamine. The resulting compound has 1) an amine anchor group that functions as a ligand and 2) a terminal methacrylate group that can form a covalent bond with acrylate monomers such as HDDA.

[0216] Without intending to be bound by theory, we believe that the covalent bonds formed between the ligands and the surrounding polymer network enhance the robustness of the ligand shell as a physical barrier in two ways. First, by anchoring the ligands to the polymer backbone of the film, the ligands are held in place, preventing dissociation and migration away from the QD surface. Furthermore, the newly formed bonds increase the effective "crosslink density" near the QD surface, preventing oxygen, water, and other harmful substances from reaching the QD surface.

[0217] As one skilled in the art will appreciate, it is possible to crosslink a ligand to the surrounding polymer network, rather than the ligand being the product of a Michael addition reaction. This can be achieved by using a ligand bearing an acrylate, methacrylate, acrylamide, or methacrylamide group in combination with a monomeric precursor of the acrylate to the polymer network.

[0218] In conclusion, aspect P1 of the present specification relates to compounds having formula (I): Formula (I):

[0219] [ka]

[0220] In the formula, the symbol R 1 , R 2 , R 3 , X, and Y are as defined above. Aspect P2 relates to compounds of aspect P1 in which Z is an amino group and Y is -NH-. Aspect P3 herein relates to compounds of aspect P1 or P2 in which R 1 (amino)(C1-C6 alkylene)(C 3- Aspect P4 herein relates to compounds of aspect P3, wherein R 1 is the following group:

[0221] [ka]

[0222] Embodiment P5 is a compound of embodiment P1 or P2, wherein R 1 (amino)(C 1-6 Alkylene)(4-7-membered heterocyclylene)(C 1-6 Aspect P6 relates to compounds of aspect P5, wherein R 1 is as follows:

[0223] [ka]

[0224] Embodiment P7 is a compound of embodiment P1 or P2, wherein R 1 (amino)(C1-C6 alkylene)(C6-C 12 Aspect P8 relates to compounds of aspect P7 in which R 1 is as follows:

[0225] [ka]

[0226] Embodiment P9 is a compound of embodiment P1 or P2, wherein R 1 (amino)(C 3-8 Cycloalkylene)(C 1-6 alkylene)(C 3-8 Aspect P10 relates to compounds of aspect P9, wherein R 1 has the following structure:

[0227] [ka]

[0228] Embodiment P11 is a compound of embodiment P1, wherein R 1 (Amino) (C 1-6 alkylene)(4- to 7-membered heterocyclylene) group, Y is absent, and the nitrogen atom in the heterocyclylene group is R to the carbon atom that is in the para position to the carbonyl group in formula (I). 1 Aspect P12 relates to compounds according to aspect P11, characterized in that they provide a binding site for R 1 has the following structure:

[0229] [ka]

[0230] Embodiment P13 is a compound of embodiment P1 or P2, wherein R 1 is polyalkyleneiminyl. 1 is polyethyleneiminyl. Embodiment P15 is a compound of embodiment P1 or P2, wherein R 1 is Z-(C1-C 12 Embodiment P16 is a compound of embodiment P15, wherein R 1 has the following structure:

[0231] [ka]

[0232] Aspect P17 is a compound according to any one of aspects P1 to P16, wherein R 2 is C1-C 12 Aspect P18 relates to compounds of aspect P17, wherein R is an alkyl group substituted with zero, one, two, or three groups selected from C1-C4 alkyl groups, C1-C6 alkoxy groups, phenoxy groups, amino groups, halogen groups, nitro groups, cyano groups, and hydroxy groups. 2 has the following structure:

[0233] [ka]

[0234] Aspect P19 is a compound according to any one of aspects P1 to P16, wherein R 2 is C3-C8 cycloalkyl and has zero, one, two, or three substituents selected from C1-C4 alkyl, C1-C6 alkoxy, amino, halogen, nitro, cyano, and hydroxy. 2 has the following structure:

[0235] [ka]

[0236] Aspect P21 is a compound according to any one of aspects P1 to P16, wherein R 2 Aspect P22 relates to compounds according to aspect P21, wherein R 2 Aspect P23 relates to a compound according to any one of aspects P1 to P22, wherein R 3 Aspect P24 relates to compounds according to any one of aspects P1 to P22, wherein R 3 Aspect P25 relates to compounds according to any of claims P1 to P16, wherein R 2 C 1-12 Alkylene methacrylate or C 1-12 alkylene methacrylamide, R 3 is hydrogen, and C 1-12 The alkylene is substituted with zero, one or more substituents independently selected from C1-C4 alkyl, C1-C6 alkoxy, phenoxy, amino, halo, nitro, cyano, and hydroxy groups. 2 is of the following structure:

[0237] [ka]

[0238] Aspect P27 relates to compounds according to any one of aspects P1 to P22, wherein X is -NH-. Aspect P28 relates to compounds according to any one of aspects P1 to P22, wherein X is -O-. Aspect P29 relates to compounds according to aspect P1 selected from Table 1 above.

[0239] Aspect P30 relates to a particle comprising (a) a luminescent nanostructure and (b) a ligand consisting of at least one compound included in any one of aspects P1 to P29. Aspect P31 relates to the particle of aspect P30, wherein the particle comprises a second ligand bound to the nanostructure, the second ligand being a compound according to formula (I) and different from the first ligand. Aspect P32 relates to the particle of aspect P31, wherein the particle comprises the following ligand:

[0240] [ka]

[0241] Embodiment P33 is the particle of any one of embodiments P30 to P32, wherein the luminescent nanostructure is selected from the group consisting of Si, Ge, Sn, Se, Te, B, C, P, BN, BP, BAs, AlN, AlP, AlAs, AlSb, AgInS, AgGaS, AgInGaS, GaN, GaP, GaAs, GaSb, InN, InP, InAs, InSb, ZnO, ZnS, ZnSe, ZnTe, and C.

[0033] Aspect P34 relates to the particle of aspect P33, wherein the luminescent nanostructure has a core-shell structure. Aspect P35 relates to the particle of aspect P34, wherein the core comprises AgInGaS and the shell comprises GaS.

[0242] Embodiment P36 relates to a method of making particles according to any of embodiments P30-P35, comprising mixing luminescent nanostructures with at least one compound according to any of embodiments P1-P29.

[0243] Embodiment P37 relates to a method of making a particle population, the method comprising: (a) combining a population of luminescent nanostructures with a Michael donor compound to form a mixture, wherein the Michael donor compound is selected from a diamine, a dithiol, or a compound having an amine group and a thiol group. (b) adding a Michael acceptor compound to the mixture, wherein the Michael acceptor compound comprises an acrylate group, a methacrylate group, an acrylamide group, or a methacrylamide group, wherein an adduct is formed by a Michael reaction between the Michael donor compound and the Michael acceptor compound, and wherein each particle comprises a luminescent nanostructure and a ligand, and the ligand comprises the adduct.

[0244] Embodiment P38 relates to a method of making a particle population, the method comprising: (a) combining a population of luminescent nanostructures with a Michael acceptor compound to form a mixture, wherein the Michael acceptor compound comprises an acrylate group, a methacrylate group, an acrylamide group, or a methacrylamide group. (b) adding a Michael donor compound to the mixture, wherein the Michael donor compound is selected from a diamine, a dithiol, or a compound having an amine group and a thiol group, wherein an adduct is formed by a Michael reaction between the Michael donor compound and the Michael acceptor compound, wherein each particle comprises a luminescent nanostructure and a ligand, wherein the ligand comprises the adduct.

[0245] Embodiment P39 relates to a method of making a particle population according to embodiment P36, the method comprising: (a) combining a Michael acceptor compound and a Michael donor compound to form a mixture, wherein the Michael donor compound is selected from a diamine, a dithiol, or a compound having an amine group and a thiol group, and the Michael acceptor compound comprises an acrylate, methacrylate, acrylamide, or methacrylamide group, and wherein an adduct is formed by a Michael reaction between the Michael donor compound and the Michael acceptor compound. (b) adding a population of luminescent nanostructures to the mixture to form a population of particles, wherein each particle comprises a luminescent nanostructure and a ligand, the ligand comprising the adduct.

[0246] Embodiment P40 is the method of any of embodiments P37-P39, wherein the Michael donor compound is a compound of formula (II):

[0247] [ka] and the Michael acceptor compound is a compound of formula (III),

[0248] [ka] and wherein the adduct conforms to formula (I):

[0249] [ka] In the formula, the symbol R 1 , R 2 , R 3 , X, and Y are as defined above.

[0250] Aspect P41 relates to a composition comprising (a) a plurality of particles according to any one of aspects P30 to P35 and / or any one of aspects P36 to P40, and (b) a carrier. Aspect P42 relates to the composition of aspect P41, wherein the carrier additionally comprises triphenyl phosphite, pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], isopropyl thioxanthone, 2,4-diethyl thioxanthone, or 3-(trimethoxysilyl)propyl acrylate. Aspect P43 relates to the composition of any one of aspects P41 to P42, wherein the carrier is a liquid. Aspect P44 relates to the composition of aspect P43, wherein the carrier comprises a curable acrylate monomer. Aspect P45 relates to the composition of any one of aspects P41 to P42, wherein the carrier is a solid. Aspect P46 relates to the composition of aspect P45, wherein the carrier comprises a cured acrylate polymer. Aspect P47 relates to the composition of any one of aspects P45-P46, wherein the composition is a film. Aspect P48 relates to the composition of any one of aspects P45-P47, wherein the composition comprises: (a) a first region comprising a first population of a plurality of particles having a first luminescent nanostructure that emits light having a first color, the first population of the plurality of particles being dispersed in a carrier; and, (b) a second region comprising a second population of particles comprising second emissive nanostructures that emit a second color different from the first color, the second population of particles dispersed in a carrier. Embodiment P49 relates to the composition of embodiment P47 or P48, wherein the film exhibits a photon conversion efficiency (PCE) of about 20% to about 35%. Embodiment P50 relates to the composition of embodiment P49, wherein the film exhibits a PCE of about 25% to about 30%. Embodiment P51 relates to a display device comprising the composition of any one of embodiments P45-P50.

[0251] Aspect P52 relates to the following composition: (a) a particle comprising a luminescent nanostructure and a ligand; and (b) a carrier comprising a curable acrylate monomer, wherein the ligand comprises one or more acrylate, methacrylate, acrylamide or methacrylamide groups that are crosslinkable with the acrylate monomer of the carrier upon curing.

[0252] Aspect P53 relates to the following composition: (a) a particle comprising a luminescent nanostructure and a ligand; and (b) A carrier comprising an acrylate polymer, wherein the ligand is crosslinked to the acrylate polymer of the carrier.

[0253] In embodiment P54, a method of making a composition is provided, comprising: (a) (i) mixing particles comprising luminescent nanostructures and ligands comprising one or more of an acrylate group, a methacrylate group, an acrylamide group, or a methacrylamide group, and (ii) a carrier comprising an acrylate monomer; and (b) curing at least a portion of the acrylate monomers of the carrier to form an acrylate polymer crosslinked with the ligand;

[0254] Aspect P55 relates to a composition obtainable by the method of aspect P54.

[0255] Embodiment P56 relates to a method of making the composition of embodiment P47 or P48, the method including depositing the composition of embodiment P43 or P44 or P52, and then curing and / or solidifying the composition.

[0256] Embodiment P57 relates to the method of embodiment P56, wherein the depositing comprises inkjet printing.

[0257] Embodiment P58 relates to a light source comprising a first electrode, a second electrode, and a layer arranged between the first and second electrodes, the layer comprising particles according to any one of claims 30 to 35 and / or particles obtained according to any one of embodiments P36 to P40. Embodiment P59 relates to the light source of embodiment P58, wherein the layer comprises a composition according to any one of embodiments P45 to P50 or any one of embodiments P53 to P55.

[0258] Aspect P60 relates to a device comprising the composition of any one of aspects P45-P50, or P53 or P55, and a light source configured to emit light of a wavelength absorbed by the nanostructure. Aspect P61 relates to the device of aspect P60, including a filter array including red filters that pass red light, green filters that pass green light, and blue filters that pass blue light, and a light valve array. Aspect P62 relates to the device of aspect P60, including: a plurality of light sources, and a light source of aspect P60 or P61, and a plurality of compositions according to any one of aspects P45-P50, or P53 or P55, each corresponding to a respective light source of the plurality of light sources and arranged to receive light emitted by a respective light source of the plurality of light sources. Aspect P63 relates to the device of any one of aspects P60-P62, including: and at least one memory containing computer program instructions, the at least one memory and the computer program instructions operable with the at least one processor to control the device to output an image.

[0259] The above examples should be understood as illustrative examples. It should be understood that any feature described in connection with any one example may be used alone or in combination with other features described, and may also be used in combination with one or more features of any other example, or any combination of any other example. Furthermore, equivalents and modifications not described above may also be employed without departing from the scope of the appended claims.

Claims

1. A compound comprising the following structure: 【Chemistry 1】 where: Y is —NH— or —S—; R １ teeth, (i) Z-(C １ -C ６ alkylene) (C ３ -C ８ Cycloalkylene) (C １ -C ６ alkylene)-, (ii) Z-(C １ -C ６ -alkylene) (4- to 7-membered heterocyclylene) (C １ -C ６ -alkylene)-, (iii) Z-(C １ -C ６ -alkylene) (C ６ -C １４ -arylene) (C １ -C ６ -alkylene)-, (iv) Z-(C ３ -C ８ Cycloalkylene) (C １ -C ６ alkylene) (C ３ -C ８ cycloalkylene)-, (v) polyalkyleneiminyl, and (vi) Z-(C １－１２ alkylene)-, or Y is absent and R １ is (vii)Z-(C １ -C ６ alkylene)(4- to 7-membered heterocyclylene)-, wherein the nitrogen atom in said heterocyclylene is linked to the carbon of formula (I) that is in the β-position to the carbonyl group. １ Given the connection points of Z is an amino group or —SH; R ３ is hydrogen and C １ -C ６ is selected from the group consisting of alkyl, R ２ teeth, (i) C １ -C ４ Alkyl group, C １ -C ６ C substituted with 0, 1, 2, or 3 groups independently selected from alkoxy groups, phenoxy groups, amino groups, halogen atoms, nitro groups, cyano groups, and hydroxy groups; １－１２ alkyl groups, (ii) C １ -C ４ Alkyl, C １ -C ６ C substituted with 0, 1, 2, or 3 groups independently selected from alkoxy, amino, halogen, nitro, cyano, and hydroxy; ３ -C ８ cycloalkyl, and (iii) 0 or 1 or more units of the polyalkylene glycol chain contain 1 or 2 C １ -C ４ alkyl-substituted polyalkylene glycols, or selected from the group consisting of: R ２ (iv) C １－１２ Alkylene methacrylate or C １－１２ alkylene methacrylamide, and R ３ is hydrogen, and the C １－１２ Alkylene is C １ -C ４ Alkyl, C １ -C ６ substituted with zero, one, or more groups independently selected from alkoxy, phenoxy, amino, halo, nitro, cyano, and hydroxy; X is —NH— or —O—.

2. The compound according to claim 1, wherein Z is an amino group and Y is -NH-.

3. 30. A particle comprising a luminescent nanostructure and a ligand comprising a compound according to any one of claims 1 to 29.

4. 4. The particle of claim 3, wherein the particle comprises a second ligand bound to the nanostructure, the second ligand being a compound according to formula (I) and different from the first ligand.

5. The particle of claim 4 , wherein the particle comprises the following ligand: 【Chemistry 2】

6. The luminescent nanostructure may be Si, Ge, Sn, Se, Te, B, C, P, BN, BP, BAs, AlN, AlP, AlAs, AlSb, AgIn. S, AgGaS, AgInGaS, GaN, GaP, GaAs, GaSb, InN, InP, InAs, InSb, ZnO, ZnS, ZnSe, ZnTe, CdS, CdSe, CdSeZn, CdTe, HgS, HgSe, HgTe, BeS, BeSe, BeTe, MgS, MgSe, G eS, GeSe, GeTe, SnS, SnSe, SnTe, PbO, PbS, PbSe, PbTe, CuF, CuCl, CuBr, CuI, Si ３ N ４ , Ge ３ N ４ , Al ２ O ３ , Al ２ 6. The particle of claim 3, comprising: a hydroxybenzoate; ...

7. The particle of claim 6 , wherein the luminescent nanostructure has a core-shell structure.

8. The particle of claim 7 , wherein the core comprises AgInGaS and the shell comprises GaS.

9. 6. A method for producing particles according to any one of claims 3 to 5, comprising mixing the luminescent nanostructures with at least one compound according to any one of claims 1 or 2.

10. combining the population of luminescent nanostructures with a Michael donor compound to form a mixture, wherein said Michael donor compound is selected from a diamine, a dithiol, or a compound having an amine group and a thiol group; and adding a Michael acceptor compound to the mixture, wherein the Michael acceptor compound comprises an acrylate group, a methacrylate group, an acrylamide group, or a methacrylamide group, and wherein an adduct is formed by a Michael reaction between the Michael donor compound and the Michael acceptor compound, and wherein each of the particles comprises a luminescent nanostructure and a ligand, and the ligand comprises the adduct; 1. A method for producing a particle population, comprising:

11. combining the population of luminescent nanostructures with a Michael acceptor compound to form a mixture, wherein the Michael acceptor compound comprises an acrylate group, a methacrylate group, an acrylamide group, or a methacrylamide group; and, adding a Michael donor compound to said mixture, wherein said Michael donor compound is selected from a diamine, a dithiol, or a compound having an amine group and a thiol group, and wherein an adduct is formed by a Michael reaction between said Michael donor compound and said Michael acceptor compound, and wherein each of said particles comprises a luminescent nanostructure and a ligand, said ligand comprising said adduct; 1. A method for producing a particle population, comprising:

12. combining a Michael acceptor compound and a Michael donor compound to form a mixture, wherein said Michael donor compound is selected from a diamine, a dithiol, or a compound having an amine group and a thiol group, and said Michael acceptor compound comprises an acrylate, methacrylate, acrylamide, or methacrylamide group, and wherein an adduct is formed by a Michael reaction between said Michael donor compound and said Michael acceptor compound; and, adding a population of luminescent nanostructures to the mixture to form a population of particles, wherein each of the particles comprises a luminescent nanostructure and a ligand, the ligand comprising the adduct; 1. A method for producing a particle population, comprising:

13. The Michael donor compound is a compound represented by formula (II), 【Transformation 3】 The Michael acceptor compound is a compound represented by formula (III): 【Chemistry 4】 and the adduct is according to formula (I): 【Transformation 5】 where: Y is —NH— or —S—; R １ teeth, (i) Z-(C １ -C ６ alkylene) (C ３ -C ８ Cycloalkylene) (C １ -C ６ alkylene)-, (ii) Z-(C １ -C ６ -alkylene) (4- to 7-membered heterocyclylene) (C １ -C ６ -alkylene)-, (iii) Z-(C １ -C ６ -alkylene) (C ６ -C １４ -arylene) (C １ -C ６ -alkylene)-, (iv) Z-(C ３ -C ８ Cycloalkylene) (C １ -C ６ alkylene) (C ３ -C ８ cycloalkylene)-, (v) polyalkyleneiminyl, and (vi) Z-(C １ー１２ alkylene)-, or Y does not exist and R １ is (vii)Z-(C １ -C ６ alkylene)(4- to 7-membered heterocyclylene)-, wherein the nitrogen atom in said heterocyclylene is linked to the carbon of formula (I) that is in the β-position to the carbonyl group. １ Given the connection points of Z is an amino group or —SH; R ３ is hydrogen and C １ -C ６ is selected from the group consisting of alkyl, R ２ teeth, (i) C １ -C ４ Alkyl group, C １ -C ６ C substituted with 0, 1, 2, or 3 groups independently selected from alkoxy groups, phenoxy groups, amino groups, halogen atoms, nitro groups, cyano groups, and hydroxy groups; １－１２ alkyl groups, (ii) C １ -C ４ Alkyl, C １ -C ６ C substituted with 0, 1, 2, or 3 groups independently selected from alkoxy, amino, halogen, nitro, cyano, and hydroxy; ３ -C ８ cycloalkyl, and (iii) 0 or 1 or more units of the polyalkylene glycol chain are 1 or 2 C １ -C ４ alkyl-substituted polyalkylene glycols, or selected from the group consisting of: R ２ (iv) C １－１２ Alkylene methacrylate or C １－１２ alkylene methacrylamide, and R ３ is hydrogen, and the C １－１２ Alkylene is C １ -C ４ Alkyl, C １ -C ６ substituted with zero, one, or more groups independently selected from alkoxy, phenoxy, amino, halo, nitro, cyano, and hydroxy; X is —NH— or —O—; 13. The method according to any one of claims 10 to 12.

14. A plurality of particles according to any one of claims 3 to 8 and / or produced by the method according to any one of claims 36 to 40; A carrier; A composition comprising:

15. The composition of claim 14, wherein the composition is a film.

16. a first region including a first population of particles having first luminescent nanostructures that emit light having a first color, the first population of particles being dispersed in the carrier; and, a second region comprising a second population of particles comprising second luminescent nanostructures that emit a second color different from the first color, the second population of particles being dispersed in the carrier; 16. The composition of claim 14 or 15, comprising:

17. 17. The composition of claim 15 or 16, wherein the film exhibits a photon conversion efficiency (PCE) of 20% to 35%.

18. a particle comprising a luminescent nanostructure and a ligand, and a carrier comprising a curable acrylate monomer; wherein the ligand comprises one or more acrylate, methacrylate, acrylamide or methacrylamide groups that are crosslinkable with the acrylate monomer of the carrier upon curing.

19. a particle comprising a luminescent nanostructure and a ligand, and a carrier comprising an acrylate polymer; wherein said ligand is crosslinked with said acrylate polymer of said carrier.

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