Semiconducting nanoparticles

Abstract

The present invention relates to semiconducting nanoparticles.

Description

[Technical Field]

[0001] Field of the present invention The present invention relates to semiconducting nanoparticles, compositions and formulations comprising the nanoparticles. Furthermore, the present invention relates to the use of the nanoparticles, optical media and optical devices comprising the nanoparticles, and processes for preparing optical devices. [Background technology]

[0002] Background technology The stability of semiconducting luminescent nanoparticles such as quantum dots (QDs) is essential for their application in electronic, optical, or biomedical devices. Properly stabilized QDs do not significantly lose photoluminescence intensity when exposed to high temperatures, air, moisture, and chemicals that may occur during processing, device fabrication, and device operation.

[0003] Monomer compounds having functional groups (so-called "anchor groups") that can be chemically adsorbed onto the nanoparticle surface to stabilize semiconducting luminescent nanoparticles, particularly QDs, and polymerizable functional groups that form polymerizable monolayers are of interest as stabilizer ligands. The advantage of using such bifunctional polymerizable stabilizer ligands is that, on the one hand, the polymerizable monomer molecules act as correct stabilizers by binding to the nanoparticle surface, and on the other hand, they enable surface polymerization with other suitable monomers, such as molecules from other ligands or matrix materials, thereby ensuring increased stability of the resulting nanoparticles. That is, the polymerizable functional groups of the ligand bound to the surface can be polymerized or crosslinked to produce a polymer shell or coating layer that can further enhance the stability of the underlying nanoparticles. Thus, depending on the properties of the polymerizable stabilizer ligand used and the polymer shell formed on the nanoparticle surface, the original properties of the nanoparticle core can be significantly altered or modified according to the application requirements.

[0004] Kim et al. ("Heat- and water-proof quantum dot / siloxane composite film: Effect of quantum dot-siloxane linkage", Journal of the SID, 25 / 2, 2017, 108-116) describes CdSe / ZnS quantum dots (QDs) functionalized with oleic acid chemically bonded to a siloxane (methacrylate) matrix. US 2015 / 0344776 A1 describes nanoparticles having a first coating layer containing a fatty acid ligand such as oleic acid, and a second coating layer containing an organic material having polar acrylate head groups and nonpolar alkyl chains. The second coating layer interacts with the first layer via the intercalation of the alkyl chains. Crouse et al. ("Influencing Solvent Miscibility and Aqueous Stability of Aluminum Nanoparticles through Surface Functionalization with Acrylic Monomers", ACS Applied Materials in Interfaces, Vol. 2, No. 9, 2010, 2560-2569) describe aluminum nanoparticles functionalized with 2-carboxyethyl acrylate.

[0005] WO2018 / 056632 A1 describes a QD functionalized with a bifunctional ligand having an anchor group such as a thiol group that chemically bonds to the surface of the QD, and a silane functional group that can interact with a silane-based material. [Prior art documents] [Patent Documents]

[0006] Patent Documents 1. US 2015 / 0344776 A1 2. WO 2018 / 056632 A1 [Non-patent literature]

[0007] Non-patent literature 3. Kim et al. (“Heat- and water-proof quantum dot / siloxane composite film: Effect of quantum dot-siloxane linkage”, Journal of the SID, 25 / 2, 2017, 108-116 4. Crouse et al. (“Influencing Solvent Miscibility and Aqueous Stability of Aluminum Nanoparticles through Surface Functionalization with Acrylic Monomers”, ACS Applied Materials in Interfaces, Vol. 2, No. 9, 2010, 2560-2569 [Overview of the Initiative]

[0008] Summary of the present invention However, the inventors have found that there is still a need for novel semiconducting luminescent nanoparticles that have improved thermal stability and long-term stability, preferably good solubility in polar solvents, that can maintain a stable dispersion in solutions, formulations, or films (including after curing), and that can exhibit high quantum yield and luminescence efficiency when used in electronic devices, optical devices, or biomedical devices.

[0009] The present invention has been made in view of the above-mentioned problems. Accordingly, an object of the present invention is to provide semiconducting luminescent nanoparticles that have improved thermal stability and long-term stability and exhibit high quantum yield and luminescence efficiency, particularly when used in electronic devices, optical devices, or biomedical devices. 0]]A further object of the present invention is to have a high chemical affinity with various polymer systems commonly used in the manufacture of electronic, optical or biomedical devices, such as (meth)acrylate or epoxy-based systems, and to have high solubility in solvents, especially polar solvents such as PGMEA commonly used in photolithography, to provide a semiconductive light-emitting nanoparticle. A further object of the present invention is to provide a semiconductive light-emitting nanoparticle capable of maintaining stable dispersion in a solution, formulation, or film (including after the polymerization / curing step).

[0010] A further object of the present invention is to provide a polymerizable compound that can impart increased stability to the nanoparticle surface and can be polymerized and / or crosslinked to further enhance the stability of the underlying nanoparticles, which is suitable for application as a stabilizer ligand or additive for semiconductive light-emitting nanoparticles. A further object of the present invention is to passivate the nanoparticle surface, and to provide chemical affinity to the nanoparticle with polar solvents such as PGMEA, and various solvents and polymer systems such as (meth)acrylate or epoxy-based used in the manufacture of electronic, optical, or biomedical devices, and to prevent aggregation of the nanoparticles, and to provide a polymerizable compound that can ensure good dispersion of the nanoparticles in a solution, formulation, or film (including after curing), which is suitable for application as a stabilizer ligand or additive for semiconductive light-emitting nanoparticles.

[0011] Furthermore, an object of the present invention is to provide an optical device having high luminous efficiency, high brightness, high contrast, high reliability, and short response time. A further object of the present invention is to provide a simple process for preparing an optical device. The inventors have found that one or more of the above objects can be addressed by the features defined in the claims. Specifically, to solve one or more of the above-described problems, the present invention provides a core, optionally one or more shell layers, and the following chemical formula (I) as defined herein

Chemical formula

Chemical formula

[0012] Furthermore, the present invention relates to a composition further containing a semiconducting light-emitting nanoparticle according to the present invention and at least one functional material, and to a composition containing a semiconducting light-emitting nanoparticle, a compound represented by chemical formula (I) as defined herein, and at least one additional functional material. In addition, the present invention relates to a formulation containing a semiconducting light-emitting nanoparticle according to the present invention, or a composition as defined herein, and at least one solvent.

[0013] The present invention further provides the use of a semiconducting light-emitting nanoparticle or composition or formulation according to the present invention in an optical device or a biomedical device. Furthermore, the present invention relates to an optical medium and an optical device, and a process for preparing the optical device. The advantages of the present invention will be apparent from the following detailed description.

Brief description of the drawings

[0014] Simple description of the drawing [Figure 1] FIG. 1 is a graph of external quantum efficiency (EQE) / % showing the change in EQE of a quantum material containing a film obtained from Example 13 measured under the same conditions. [Figure 2] ​Figure 2 shows the normalized intensity emission spectra across wavelengths, illustrating the shift in maximum intensity of the quantum materials containing the film obtained from Example 13, each measured under the same conditions. [Figure 3] Figure 3 shows the EQE measurement results for Example 14. [Modes for carrying out the invention]

[0015] Detailed description of the present invention The best mode for carrying out the present invention will be described in detail thereafter. When used herein, dashed lines or asterisks ("a" or "*") are generally used to indicate a bond or connection point to an adjacent unit or group of a compound, for example, in the case of a polymer, an adjacent repeating or constituent unit, or another group, for example, a side chain in the case of a monomer compound. As used herein, the term “anchor group” refers to an organic functional group that can interact with the surface of a semiconducting nanoparticle, thereby binding or chemisorbing a compound containing the anchor group to the nanoparticle surface, for example, by covalent or ionic bonding, or via dipole-dipole interactions. A compound that is bound to or attached to the surface of a nanoparticle (these terms are used interchangeably herein) or can be bound to or attached is referred herein to as a “ligand” or “surface ligand.” The following definitions apply to chemical groups used as general definitions. They apply only when no more specific definition is given. In the sense of this invention, an aryl group contains 5 to 40 aromatic ring atoms, none of which are heteroatoms. In this specification, an aryl group is understood to mean either a simple aromatic ring, such as benzene, or a condensed aromatic polycycle, such as naphthalene, phenanthrene, or anthracene. A condensed aromatic polycycle in the sense of this application consists of two or more simple aromatic rings that are condensed with each other. As a result, an arylene group in the sense of this invention is derived from an aryl group, but with hydrogen atoms removed from two ring carbon atoms, such as phenylene.

[0016] In the sense of the present invention, a heteroaryl group is an aromatic group containing 5 to 40 aromatic ring atoms, at least one of which is a heteroatom, i.e., a heteroaromatic group. The heteroatom is preferably selected from N, O, and S. In this specification, a heteroaryl group is understood to mean either a simple heteroaromatic ring such as pyridine, pyrimidine, or thiophene, or a condensed heteroaromatic polycyclic ring such as quinoline or carbazole. A condensed heteroaromatic polycyclic ring in the sense of this application consists of two or more simple heteroaromatic rings that are condensed with each other. As a result, a heteroarylene group in the sense of the present invention is derived from a heteroaryl group, but with hydrogen atoms removed from two ring carbon atoms.An aryl or heteroaryl group, which may be substituted in each case as defined below, and may be linked to an aromatic or heteroaromatic ring system via any desired position, or an arylene or heteroarylene group, in particular, benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluorantene, benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran Dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthidine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quino Xalinoimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthyrizine, azacarbazole, benzocarbolin, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1 This is interpreted to mean groups derived from 2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purines, pteridines, indidines, and benzothiadiazole.

[0017] In the sense of the present invention, an alkaryl or alkarylene group is understood to mean an aryl or arylene group as defined above, to which an alkyl group is bonded and which may be substituted as defined below. In the context of this invention, an alkyl heteroaryl or alkyl heteroarylene group is understood to mean a heteroaryl or heteroarylene group as defined above, to which an alkyl group as defined below is attached and which may be substituted as defined below. In the sense of the present invention, an aromatic ring system contains 5 to 40 C aromatic ring atoms in the ring system and does not contain heteroatoms as aromatic ring atoms. Therefore, an aromatic ring system in the sense of this application does not contain heteroaryl groups. A heteroaromatic ring system in the sense of the present invention contains 5 to 40 aromatic ring atoms, at least one of which is a heteroatom. The heteroatom is preferably selected from N, O, or S. A heteroaromatic ring system is defined as the above aromatic ring system, except that it must have at least one heteroatom as one of the aromatic ring atoms.

[0018] In the sense of the present invention, an aromatic or heteroaromatic ring system is intended to be interpreted as meaning a system that does not necessarily contain only aryl or heteroaryl groups, but in addition, multiple aryl or heteroaryl groups may be connected by one or more optionally substituted nonaromatic units such as C, Si, N, O, or S atoms. In such cases, the nonaromatic units preferably constitute less than 10% of the total number of non-H atoms in the entire aromatic ring system. Thus, for example, systems such as 9,9'-spirobifluorene, 9,9'-diarylfluorene, triarylamine, diaryl ether, and stilbene are also understood in the sense of the present invention as systems in which two or more aryl groups are connected, for example, by linear or cyclic alkyl, alkenyl, or alkynyl groups, or by silyl groups. Furthermore, systems in which two or more aryl or heteroaryl groups are linked to each other via single bonds, such as biphenyl, terphenyl, or bipyridine, are also understood as aromatic ring systems in the sense of the present invention.

[0019] For the purposes of the present invention, a linear alkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl group having 3 to 40 carbon atoms, or a linear alkenyl or alkynyl group having 2 to 40 carbon atoms, or a branched alkenyl or alkynyl group with 3 to 40 carbon atoms, wherein the individual H atoms or CH2 groups in the above-mentioned groups may be substituted as follows, preferably radical methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methyl-butyl, n-butyl It is understood to mean s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neo-hexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethinyl, propynyl, butynyl, pentynyl, hexynyl, or octinyl. Considering the above definition, a linear alkylene group having 1 to 40 carbon atoms, a cyclic or branched alkylene group having 3 to 40 carbon atoms, a linear alkenylene or alkynylene group having 2 to 40 carbon atoms, or a branched alkenylene or alkynylene group having 3 to 40 carbon atoms is understood to mean the diradicals of each of the radicals described above. In the sense of the present invention, an aralkyl or alkylene group is understood to mean an alkyl or alkylene group as defined above, to which an aryl group as defined above is attached and which may be substituted as defined below.

[0020] In the sense of the present invention, a heteroarylalkyl or heteroarylalkylene group is understood to mean an alkyl or alkylene group as defined above, to which a heteroaryl group as defined above is bonded and which may be substituted as defined below.

[0021] An alkoxy group having 1 to 40 carbon atoms is preferably understood to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, or 2,2,2-trifluoroethoxy. According to the present invention, semiconductive light-emitting nanoparticles are provided, comprising a core, optionally one or more shell layers, and a compound represented by chemical formula (I) [Chemical formula] and containing a compound represented by . The index “o” is 1, 2 or 3, preferably 1.

[0022] The group R a , a , a , a , a , a , a , a , a , a is H, D, CN, a linear alkyl or alkoxy group having 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms), each of which may be substituted by one or more groups R a wherein in each case one or more CH2 groups are R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a , -C(=O)O-, or -C(=O)NR a- may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); Aromatic ring systems or heteroaromatic ring systems having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a (These may be substituted by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2)

[0023] base R 2 , R 3 These are: a linear alkyl or alkoxy group having H, D, CN, and 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more R groups). a It may also be substituted by, where in each case one or more CH2 groups are R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); or an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a (These may be substituted by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2)

[0024] Preferably, base R 2 and R 3 One of them is H, and the other is as defined above. More preferably both groups R 2 and R 3 H is H. A 1 teeth, [ka] and n=0 or 1; or divalent base [ka] And, Y is O, N, S, preferably O or N, where the dashed line indicates bonding to the rest of the compound (i.e., divalent group A). 1 From unit C=CR 1 (These are the bondings to and to the base L, respectively.) Here A 2 This refers to an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a It may be substituted by a divalent group selected from D, F, Cl, Br, I, CN, NO2, where one or more H atoms of the aromatic ring system or heteroaromatic ring system may be replaced by D, F, Cl, Br, I, CN, NO2. In a preferred embodiment, A 1 is a divalent base [ka] And Y is as defined above.

[0025] R aEach occurrence may be the same or different, and the groups are: a linear alkyl or alkoxy group having H, D, and 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms); a linear alkenyl or alkynyl group having 2 to 40 carbon atoms (preferably 2 to 24 carbon atoms, more preferably 2 to 12 carbon atoms); a branched alkenyl or alkynyl group having 3 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 3 to 12 carbon atoms); and an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (wherein one or more H atoms in each of the above groups may be replaced by D, F, Cl, Br, I, and wherein two or more adjacent substituents R a These elements may form arbitrary monocyclic or polycyclic aliphatic ring systems with respect to one another.

[0026] The linking group L is a linear alkylene group having 1 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms); a linear alkenylene or alkynylene group having 2 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); or a branched alkenylene or alkynylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms) (each of which is one or more groups R a Each of these may be substituted by, and in each case one or more CH2 groups are arylene groups or heteroarylene groups having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), Si(R a )2, Ge(R a )2, Sn(R a)2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), aralkylene group, heteroaralkylene group, alkylarylene group or alkylheteroarylene group (each of which is one or more groups R a (which may be substituted by, and in each case one or more H atoms may be replaced by D, F, Cl, Br, I, CN, NO2), or the following chemical formula (II) [ka]

[0027] During the ceremony m is an integer between 1 and 50, preferably between 1 and 25, more preferably between 2 and 20, and even more preferably between 4 and 12; l is an integer between 1 and 25, preferably between 1 and 20, more preferably between 1 and 12, and even more preferably between 1 and 8; L 1 teeth, [ka] is; L 2 teeth, [ka] is;

[0028] Here, the dashed line indicates the bond to the rest of the compound, and the symbol "*" indicates the group L 1 and base L 2 Mark the bond between and here L 1 and L2 Each of these is one or more base R a It may also be replaced by, where L 1 and L 2 One or more CH2 groups are -R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, NR a , or -C(=O)NR a - may be replaced by, and here L 1 and L 2 One or more H atoms in are divalent groups selected from the groups represented by D, F, Cl, Br, I, CN, or NO2.

[0029] In a preferred embodiment, L is a linear alkylene group having 1 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms); a linear alkenylene or alkynylene group having 2 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); or a branched alkenylene or alkynylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms) (each of which is one or more groups R a Each of these may be substituted by, and in each case one or more CH2 groups are arylene groups or heteroarylene groups having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), aralkylene group, heteroaralkylene group, alkylarylene group or alkylheteroarylene group (each of which is one or more groups R a (These may be substituted by, and in each case, one or more H atoms may be replaced by D, F, Cl, Br, I, CN, NO2),

[0030] Alternatively, the following chemical formula (II) [ka] L in the ceremony 1 teeth, [ka] [ka] is; and L 2 teeth, [ka] Here, m, l and R a It is as defined above, Selected from, where the dashed line indicates the bond to the rest of the compound (i.e., group L, L) 1 , and L 2 From Base A 1 or base X 1 The symbol "*" indicates a connection to the base L. 1 and L 2 The bond between and and the symbol "*" indicates the base L 1 and base L 2 Mark the connection between them.

[0031] X 1 is an anchor group that is the same or different in each occurrence, preferably -COOM 1 , -PO(OH)(OM 1 ), -PO(OM 1 )2, -OC(S)SM 1 , -NH2, -NHR a , -N(R a )2, -SO3M 1 , -SM 1 , -Ar 1 -SM 1 , -OCO-A 3 -SM 1 , -COO-A 3 -SM 1 , -NCO-A 3 -SM 1 , SiOR a , or -N(CS2M 1 )2. In a preferred embodiment, X 1 is the same or different in each occurrence, and is -OC(S)SM 1 , -SM 1 , -Ar 1 -SM 1 , -OCO-A 3 -SM 1 , -COO-A 3 -SM 1 , -NCO-A 3 -SM 1 , or -N(CS2M 1 )2. Ar 1 is a divalent group selected from an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), each of which may be substituted by one or more groups R a , and wherein one or more H atoms of the aromatic or heteroaromatic ring system may be replaced by D, F, Cl, Br, I, CN, NO2. <​​​This includes a linear alkylene group having 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms), and a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more groups R a They may be substituted with Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring systems or heteroaromatic ring systems having 5 to 25 aromatic ring atoms (preferably 5 to 18 aromatic ring atoms, more preferably 5 to 12 aromatic ring atoms) (each of which has one or more groups R a It may be substituted by a divalent group selected from D, F, Cl, Br, I, CN, NO2, where one or more H atoms of the aromatic ring system or heteroaromatic ring system may be replaced by D, F, Cl, Br, I, CN, NO2. M 1 is a hydrogen atom, or 1 / 2 Mg 2+ , 1 / 2 Cu 2+ , 1 / 2 Zn 2+ , 1 / 2 Pb 2+ , 1 / 2 Sn 2+ , 1 / 2 Cd 2+ , 1 / 3 Bi 3+ , or 1 / 4 Sn 4+ A metal cation selected from, preferably a hydrogen atom, 1 / 2 Mg 2+ , 1 / 2 Cu 2+ , or 1 / 2 Zn 2+ More preferably, it shows a hydrogen atom.

[0033] When used in this specification, the notation "1 / 2 Mg 2+"1 / 2 Cu 2+ "1 / 2 Zn 2+ " or "1 / 2 Cd 2+ " is the symbol M 1 is Mg 2+ Cu 2+ Zn 2+ or Cd 2+ When referring to divalent cations such as those mentioned above, it should be understood that the divalent cation shares its positive charge with two separate monovalent anionic groups. In other words, it is a single positive charge attached to a monovalent anionic group X 1 It shares a positive charge with another monovalent anionic group, for example, another monovalent anionic group X located in the same molecule (intramolecular) or in a different molecule (intermolecular) of the compound represented by chemical formula (I). 1 Share it with them. Similarly, trivalent or tetravalent cations share their three or four positive charges with the anionic group.

[0034] According to the present invention, semiconducting luminescent nanoparticles comprise a core, optionally one or more shell layers, and a bifunctional polymerizable compound represented by chemical formula (I) as defined herein, exhibiting improved thermal stability and long-term stability, as well as high quantum yield and high luminescence efficiency, and thus are considered to be advantageously applicable in electronic devices, optical devices, or biomedical devices. Furthermore, according to the present invention, semiconducting luminescent nanoparticles have been found to have high chemical affinity with a variety of solvents and polymer systems, in particular (meth)acrylate or epoxy-based systems typically used as matrix materials in optical devices, and thus interact well with matrix materials, achieve a high degree of crosslinking, exhibit good solubility in solvents, especially polar solvents, and maintain a stable dispersion in solution, formulation, or film (i.e., even after curing) without aggregation. As used herein, the term “polymerizable” means that each compound (e.g., a monomer compound) can chemically react or crosslink, preferably at initiation, to form polymer chains or a three-dimensional network. Polymerization initiation may occur in response to light irradiation or heat, or using an initiator compound, but is not limited to these.

[0035] In a more preferred embodiment of the present invention, in chemical formula (I), A 1 teeth, [ka] and X 1 In each occurrence, -OC(S)SM may be the same or different. 1 -SM 1 ,-Ar 1 -SM 1 , -OCO-A 3 -SM 1 ,-COO-A 3 -SM 1 ,-NCO-A 3 -SM 1 , or -N(CS2M 1 ) Selected from 2, Here, the symbols are Y and Ar. 1 , A 3 and M 1 The divalent linking group L is as defined above.

[0036] In a still more preferred embodiment of the present invention, in chemical formula (I), A 1 teeth, [ka] And, L is a linear alkylene group having 1 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms); a linear alkenylene or alkynylene group having 2 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); or a branched alkenylene or alkynylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms) (each of which is one or more groups R a Each of these may be substituted by, and in each case one or more CH2 groups are arylene groups or heteroarylene groups having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), aralkylene group, heteroaralkylene group, alkylarylene group or alkylheteroarylene group (each of which is one or more groups R a (which may be substituted by, and in each case one or more H atoms may be replaced by D, F, Cl, Br, I, CN, NO2), or the following chemical formula (II) [ka] L in the ceremony 1 teeth, [ka] [ka] is;

[0037] and L 2 teeth, [ka] is; and X 1 In each occurrence, -OC(S)SM may be the same or different. 1 -SM 1 ,-Ar 1 -SM 1 , -OCO-A 3 -SM 1 ,-NCO-A 3 -SM 1 ,-COO-A 3 -SM 1 , or -N(CS2M 1 ) Selected from 2, where the symbols and indices m, l, Y, R a Ar 1 , A 3 and M 1 It is defined as above. More preferably, the compound represented by chemical formula (I) is the following chemical formula (III) [ka] Here, the symbols are Y and R. 1 , R 2 , R 3 , A 3 , L and M 1 As defined above, and where Z is N or O, This represents a compound represented by [this symbol].

[0038] In a more preferred embodiment of the present invention, the compound represented by chemical formula (I) or chemical formula (III) is the following: chemical formula (IV), (Va), or (Vb), preferably chemical formula (IV) or (Va) [ka] In the formulas, the symbols have the meanings defined above, and in chemical formula (IV), the index j is an integer between 1 and 40, preferably between 3 and 24, more preferably between 4 and 12. This represents a compound represented by [this symbol].

[0039] The compounds represented by chemical formula (I), and the compounds represented by chemical formulas (IV) and (Va), are the following: (IV-1) to (IV-6) and (V-1) to (V-6) [ka] [ka] [ka] The symbols and indices in the formula have the meanings defined above, where indices g and f represent integers between 1 and 40, preferably between 3 and 24, and more preferably between 4 and 12. Specifically, preferably, among the compounds represented by chemical formulas (IV-1) to (IV-6) and (V-1) to (V-6), M 1 It is hydrogen. According to a more preferred embodiment of the present invention, the compound represented by chemical formula (I) has a molecular weight in the range of 150 to 2000 Da. More preferably, it has a molecular weight in the range of 150 to 1500 Da, and even more preferably in the range of 200 to 1000 Da.

[0040] - Semiconducting luminescent nanoparticles In accordance with the present invention, a wide variety of publicly known semiconducting luminescent nanoparticles may be used as the inorganic portion of the semiconducting luminescent nanoparticles as needed. The type of shape of the semiconducting luminescent nanoparticles of the present invention is not specifically limited. Any type of semiconducting luminescent nanoparticle, such as spherical, elongated, star-shaped, or polyhedral semiconducting luminescent nanoparticles, may be used. The semiconducting luminescent nanoparticles of the present invention include a core and may optionally include one or more shell layers. In accordance with the present invention, the term “shell layer” means a structure that completely or partially covers the core. Preferably, the one or more shell layers completely cover the core. The terms “core” and “shell” are well known in the art and are typically used in the field of quantum materials, such as in US 8221651 B2.

[0041] The one or more shell layers of the semiconducting luminescent nanoparticles are not specifically limited and may be a single shell layer, a double shell layer, or a multi-shell layer having two or more shell layers, preferably a double shell layer. In accordance with the present invention, the term "nano" means a size between 1 nm and 999 nm. Preferably, it is from 1 nm to 150 nm. In a preferred embodiment of the present invention, the semiconducting luminescent nanoparticles of the present invention are quantum-sized materials. In accordance with the present invention, the term "quantum size" refers to the size of the semiconducting material itself, without any compounds or other surface modifications, and may exhibit quantum confinement effects as described in, for example, ISBN: 978-3-662-44822-9. Preferably, the overall structural size of the quantum-sized material is from 1 nm to 100 nm, more preferably from 1 nm to 30 nm, and even more preferably from 5 nm to 15 nm.

[0042] In accordance with the present invention, the core of the semiconducting light-emitting nanoparticles may be modified. For example, CdS, CdSe, CdTe, ZnS, ZnSe, ZnSeS, ZnTe, ZnO, GaAs, GaP, GaSb, HgS, HgSe, HgSe, HgTe, InAs, InP, InPS, InPZnS, InPZn, InPGa, InSb, AlAs, AlP, AlSb, Cu2S, Cu2Se, CuInS2, CuInSe2, Cu2(ZnSn)S4, Cu2(InGa)S4, TiO2 alloys, and any combination thereof may be used.

[0043] In a preferred embodiment of the present invention, the core of the semiconducting luminescent nanoparticle comprises one or more Group 13 elements and one or more Group 15 elements of the periodic table. For example, GaAs, GaP, GaSb, InAs, InP, InPS, InPZnS, InPZn, InPGa, InSb, AlAs, AlP, AlSb, CuInS2, CuInSe2, Cu2(InGa)S4, and any combination thereof. Alternatively, the core may contain In and P atoms. For example, InP, InPS, InPZnS, InPZn, InPGa. At least one of the shell layers contains a first element from group 12, 13, or 14 of the periodic table and a second element from group 15 or 16 of the periodic table, preferably all of the shell layers contain a first element from group 12, 13, or 14 of the periodic table and a second element from group 15 or 16 of the periodic table.

[0044] In a preferred embodiment of the present invention, at least one of the shell layers may contain a first element from group 12 of the periodic table and a second element from group 16 of the periodic table, such as CdS, CdZnS, ZnS, ZnSe, ZnSSe, ZnSSeTe, CdS / ZnS, ZnSe / ZnS, or ZnS / ZnSe shell layers. Preferably, all shell layers contain elements from Group 12 (First) and Group 16 (Second) of the periodic table. More preferably, at least one shell layer is given by the following equation (VI) ZnS x Se y Te z - (VI) In equation (I), 0≦x≦1, 0≦y≦1, 0≦z≦1, and x+y+z=1, where more preferably 0≦x≦1, 0≦y≦1, z=0, and x+y=1. For example, ZnS, ZnSe, ZnSeS, ZnSeSTe, CdS / ZnS, ZnSe / ZnS, and ZnS / ZnSe shell layers may preferably be used.

[0045] Preferably, all shell layers are represented by equation (VI). For example, CdSe / CdS, CdSeS / CdZnS, CdSeS / CdS / ZnS, ZnSe / CdS, CdSe / ZnS, InP / ZnS, InP / ZnSe, InP / ZnSe / ZnS, InP / ZnS / ZnSe, InPZn / ZnS, InPZn / ZnSe / ZnS, InPZn / ZnS / ZnSe, ZnSe / CdS, ZnSe / ZnS semiconducting luminescent nanoparticles or any combination thereof may be used as semiconducting luminescent nanoparticles for the use of green and / or red radiation. More preferably, InP / ZnS, InP / ZnSe, InP / ZnSe / ZnS, InP / ZnS / ZnSe, InPZn / ZnS, InPZn / ZnSe / ZnS, and InPZn / ZnS / ZnSe may be used. In a more preferred embodiment of the present invention, the shell layer of the semiconducting light-emitting nanoparticles is a double shell layer. These semiconducting luminescent nanoparticles are, for example, publicly available from Sigma-Aldrich and / or described in ACS Nano, 2016, 10 (6), pp 5769-5781, Chem. Moter. 2015, 27, 4893-4898 and in international patent application publication No. WO2010 / 095140A.

[0046] - Additional compounds In accordance with aspects of the present invention, the semiconducting luminescent nanoparticles according to the present invention comprise a compound or ligand attached to the outermost surface of the nanoparticle (i.e., the outermost surface of the core or, if present, the shell layer), wherein the compound or ligand is preferably a bifunctional polymerizable compound represented by chemical formula (I) as defined herein. The semiconducting luminescent nanoparticles of the present invention may optionally further contain a compound or ligand, different from the compound represented by chemical formula (I), that adheres to the outermost surface of the nanoparticle. Consequently, the outermost surface of the core or shell layer of the semiconducting luminescent nanoparticles may be overcoated with a different type of compound, along with the compound represented by chemical formula (I).

[0047] When one or more of the other compounds or ligands are attached to the outermost surface of the core or to the shell layer of the semiconducting luminescent nanoparticles, the amount of the compound represented by formula (I) is in the range of 30 wt.% to 99.9 wt%, preferably 50 wt% to 95 wt%, and more preferably 60 wt% to 90 wt%, of the total amount of compounds attached to the outermost surface of the core or to the shell layer. While we do not wish to be constrained by theory, such compounds may more readily result in the dispersion of semiconducting luminescent nanoparticles in a solvent.

[0048] Other compounds in common use include phosphines and phosphine oxides such as trioctylphosphine oxide (TOPO), trioctylphosphine (TOP), and tributylphosphine (TBP); phosphonic acids such as dodecylphosphonic acid (DDPA), tridecylphosphonic acid (TDPA), octadecylphosphonic acid (ODPA), and hexylphosphonic acid (HPA); amines such as decylamine (DDA), tetradecylamine (TDA), hexadecylamine (HDA), and octadecylamine (ODA), and oleylamine (OLA); thiols such as hexadecanethiol and hexanethiol; carboxylic acids such as oleic acid, stearic acid, and myristic acid; acetic acid, and any combination thereof.

[0049] Examples of such compounds are described, for example, as ligands in International Patent Application Publication No. WO 2012 / 059931A. -Compound The present invention further or general formula (III) [ka] During the ceremony, Y is O, N, or S, preferably O or N. Z is either O or N, R 1This includes H, D, CN, a linear alkyl or alkoxy group having 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more R groups). a It may also be substituted by, where in each case one or more CH2 groups are R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); Aromatic ring systems or heteroaromatic ring systems having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a (These may be substituted by D, F, Cl, Br, I, CN or NO2, where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2);

[0050] R 2 , R 3 These are: a linear alkyl or alkoxy group having H, D, CN, and 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more R groups). a It may also be substituted by, where in each case one or more CH2 groups are R a C=CR a -, -C≡C-, Si(Ra )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); or an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a (These may be substituted by D, F, Cl, Br, I, CN or NO2, where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2);

[0051] R a Each occurrence may be the same or different, and the groups are: a linear alkyl or alkoxy group having H, D, and 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms); a linear alkenyl or alkynyl group having 2 to 40 carbon atoms (preferably 2 to 24 carbon atoms, more preferably 2 to 12 carbon atoms); a branched alkenyl or alkynyl group having 3 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 3 to 12 carbon atoms); and an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (wherein one or more H atoms in each of the above groups may be replaced by D, F, Cl, Br, I, and wherein two or more adjacent substituents R a (These elements may form any monocyclic or polycyclic aliphatic ring system with each other;

[0052] L is a linear alkylene group having 1 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms); a linear alkenylene or alkynylene group having 2 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); or a branched alkenylene or alkynylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms) (each of which is one or more groups R a Each of these may be substituted by, and in each case one or more CH2 groups are arylene groups or heteroarylene groups having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), aralkylene group, heteroaralkylene group, alkylarylene group or alkylheteroarylene group (each of which is one or more groups R a (which may be substituted by, and in each case one or more H atoms may be replaced by D, F, Cl, Br, I, CN, NO2), or the following chemical formula (II) [ka]

[0053] During the ceremony m is an integer between 1 and 50, preferably between 1 and 25, more preferably between 2 and 20, and even more preferably between 4 and 12; l is an integer between 1 and 25, preferably between 1 and 20, more preferably between 1 and 12, and even more preferably between 1 and 8; L 1 teeth, [ka] is; L 2 teeth, [ka] is;

[0054] Here, the dashed lines represent the bonds to the remaining compound (i.e., L, L). 1 and L 2 The symbol "*" indicates a bond from base Y or base Z, and the symbol "*" indicates base L 1 and base L 2 Mark the bond between and here L 1 and L 2 Each of these is one or more base R a It may also be replaced by, where L 1 and L 2 One or more CH2 groups are -R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, NR a , or -C(=O)NR a - may be replaced by, and here L 1 and L 2 One or more H atoms in are divalent groups selected from the groups represented by D, F, Cl, Br, I, CN, or NO2;

[0055] A 3This includes a linear alkylene group having 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms), and a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more groups R a They may be substituted with Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring systems or heteroaromatic ring systems having 5 to 25 aromatic ring atoms (preferably 5 to 18 aromatic ring atoms, more preferably 5 to 12 aromatic ring atoms) (each of which has one or more groups R a (which may be substituted by, and where one or more H atoms in the aromatic ring system or heteroaromatic ring system are divalent groups selected from D, F, Cl, Br, I, CN, NO2); and

[0056] M 1 is a hydrogen atom, or 1 / 2 Mg 2+ , 1 / 2 Cu 2+ , 1 / 2 Zn 2+ , 1 / 2 Pb 2+ , 1 / 2 Sn 2+ , 1 / 2 Cd 2+ , 1 / 3 Bi 3+ , or 1 / 4 Sn 4+ A metal cation selected from, preferably a hydrogen atom, 1 / 2 Mg 2+ , 1 / 2 Cu 2+ , or 1 / 2 Zn 2+ More preferably, showing hydrogen atoms, This relates to compounds represented by [the specified method / function]. In relation to semiconducting luminescent nanocrystals, preferred embodiments, symbols, and indices of the compound represented by chemical formula (III) as defined above are equally preferred in this context. Specifically, preferably, the compound represented by chemical formula (III) according to the present invention represents the compound represented by chemical formula (IV), (Va), or (Vb) as defined above. More preferably, the compound represented by chemical formula (III) according to the present invention represents one of the compounds represented by chemical formulas (IV-1) to (IV-6) and (V-1) to (V-6) as defined above.

[0057] The bifunctional polymerizable compounds represented by chemical formula (III) as defined herein, comprising a thiol / thiolate functional group and a polymerizable acrylate-based functional group, separated from each other by a divalent linking or crosslinking group (i.e., group L), are particularly suitable for application as ligands or additives for semiconducting luminescent nanoparticles because they have high affinity (i.e., can chemically interact with) polar solvents such as PGMEA and (meth)acrylate or epoxy-based systems typically used in device manufacturing processes. Due to their high affinity, these compounds can chemically bond to ((meth)acrylate) matrix materials via crosslinking containing double bonds, thereby providing higher stability to the nanoparticles, particularly after film curing and film heating, preventing nanoparticle aggregation, ensuring good dispersion of nanoparticles in solutions, formulations, or films (including after film curing), thereby further enhancing the stability of the nanoparticles.

[0058] -composition When used in electronic, optical, or biomedical devices, the semiconducting luminescent nanoparticles according to the present invention may be combined with host or matrix materials and / or optically transparent polymers, or other functional materials commonly used in prior art electronic, optical, or biomedical devices, to form compositions. A wide variety of suitable functional materials are known to those skilled in the art in the fields of electronic, optical, or biomedical devices, and these may be preferably used. In a first aspect, the present invention thus further provides semiconducting luminescent nanoparticles according to the present invention, i.e., semiconducting luminescent nanoparticles comprising a core, optionally one or more shell layers, and a compound represented by chemical formula (I) as defined herein, and compositions comprising at least one further functional material.

[0059] In this aspect of the present invention, the semiconducting luminescent nanoparticles comprise a compound or ligand attached to the outermost surface of the nanoparticle (i.e., the outermost surface of the core or, if present, the shell layer), wherein the compound or ligand is preferably a bifunctional polymerizable compound represented by chemical formula (I) as defined herein. At least one further functional material is preferably selected from the group consisting of organic light-emitting materials, inorganic light-emitting materials, charge transport materials, host or matrix materials, optically transparent polymers, antioxidants or stabilizers, radical quenchers, photoinitiators or polymerization initiators, wetting and dispersing agents, scattering particles, refractive index modifiers, developer dissolution accelerators, scum removers, adhesion enhancers, polymerization inhibitors, defoamers, surfactants, and sensitizers. Preferably, at least one further functional material is a host or matrix material, more preferably selected from (meth)acrylate monomers or polymers. (Meth)acrylate monomers represented by chemical formula (VII) as defined below are particularly preferred. Further preferred examples of functional materials that can be used in accordance with the present invention are described below, but are not limited to them.

[0060] When used herein, polymerization initiators are molecules or compounds that generate reactive species (free radicals, cations, or anions) through different pathways involving dissociation and electron transfer in order to initiate or accelerate a crosslinking or polymerization reaction. Thus, photoinitiators are molecules or compounds that generate such reactive species when exposed to light (UV or visible light), and thermal initiators are molecules or compounds that generate such reactive species when heat is applied. The polymerization initiator is not specifically limited within the scope of the present invention and may be, for example, a photoinitiator, a nucleophilic initiator, a radical initiator, or a thermal initiator. Suitable examples of these are known to those skilled in the art. Preferably, a photoinitiator or a thermal initiator is used.

[0061] Preferred wetting and dispersing agents preferably include anchor groups selected from phosphine groups, phosphine oxide groups, phosphate groups, phosphonate groups, thiol groups, tertiary amine groups, carboxyl groups, heterocyclic groups, silane groups, sulfonic acids, hydroxyl groups, and phosphonic acids. Examples of preferred wetting and dispersing agents are disclosed, for example, in WO 2017 / 054898 A1. In accordance with the present invention, any type of publicly known material can be used as the organic light-emitting material and charge transport material. For example, well-known organic fluorescent materials, organic host materials, organic dyes, organic electron transport materials, organometallic complexes, and organic hole transport materials can be preferably used. In accordance with the present invention, any type of publicly known light scattering particle having a refractive index different from that of the matrix material of the layer containing the light scattering particle and capable of giving a Mie scattering effect may be used as the light scattering particle, if desired.

[0062] Preferably, the scattering particles may be small inorganic oxides such as SiO2, SnO2, CuO, CoO, Al2O3TiO2, Fe2O3, Y2O3, ZnO, MgO, polymerized organic particles such as polymerized polystyrene and polymerized PMMA, or inorganic hollow oxides such as hollow silica, or any combination thereof. The adhesion promoter has the function of preventing the pattern from peeling off due to stress applied after curing when forming a cured film from the polymerizable composition of the present invention. It is preferable to use imidazole and a silane coupling agent as the adhesion promoter. Imidazole and a silane coupling agent are preferably used as adhesion enhancers. Examples of imidazole include 2-hydroxybenzimidazole, 2-hydroxyethylbenzimidazole, benzimidazole, 2-hydroxyimidazole, imidazole, 2-mercaptoimidazole, and 2-aminoimidazole. Among these, 2-hydroxybenzimidazole, benzimidazole, 2-hydroxyimidazole, and imidazole are specifically preferred.

[0063] Developer dissolving accelerators or scum removers control the solubility of the coating formed in the developer, thereby preventing scum from remaining on the substrate after development. Crown ethers can be used as this additive. The simplest crown ether has the general formula (-CH2-CH2-O-) nIt is represented as follows. Among these, in the present invention, crown ethers of the formula n = 4 to 7 are preferably used. On the other hand, crown ethers are often individually referred to as "x-crown-y-ethers," where x and y represent the total number of atoms forming the ring and the number of oxygen atoms contained therein, respectively. In the present invention, the additive may be preferably selected from the group consisting of crown ethers X = 12, 15, 18 and 21 and y = x / 3, their benzo-condensed (-condensed) products, and their cyclohexyl-condensed (-condensed) products. Preferred examples of crown ethers include 2-crown-7-ether, 18-crown-6-ether, 15-crown-5-ether, 12-crown-4-ether, dibenzo-21-crown-7-ether, dibenzo-18-crown-6-ether, dibenzo-15-crown-5-ether, dibenzo-12-crown-4-ether, dicyclohexyl-21-crown-7-ether, dicyclohexyl-18-crown-6-ether, dicyclohexyl-5-crown-5-ether, and dicyclohexyl-12-crown-4-ether. Among these, additives selected from the group consisting of 18-crown-6-ether and 15-crown-5-ether are particularly preferred. The amount is preferably 0.05 to 15 parts by weight, more preferably 0.1 to 10 parts by weight, based on 100 parts by weight of the organic polysilicon compound of the present invention.

[0064] As polymerization inhibitors, nitrone derivatives, nitroxide radical derivatives, and hydroquinone derivatives such as hydroquinone, methylhydroquinone, and butylhydroquinine may be incorporated. These may be used alone or in combination of two or more. The amount is preferably 0.1 to 10 parts by weight, based on 100 parts by weight of the organic polysilicon compound of the present invention. Examples of defoaming agents include alcohol (C1-C1). 18This includes higher fatty acids such as oleic acid and stearic acid, higher fatty acid esters such as glycerin monolaurate, polyethers such as polyethylene glycol (PEG) (Mn: 200-10000) and polypropylene glycol (Mn: 200-10000), silicone compounds such as dimethyl silicone oil, alkyl-modified silicone oil, and fluorosilicone oil, and organic siloxane surfactants, which are described in detail below. These may be used alone or in combination of two or more. The amount is preferably 0.1 to 3 parts by weight, based on 100 parts by weight of the organic polysilicon compound of the present invention. If necessary, the polymerizable composition of the present invention may further contain surfactants incorporated for the purpose of improving coating properties, developability, etc. Examples of surfactants usable in the present invention include nonionic, anionic, and amphoteric surfactants.

[0065] Examples of nonionic surfactants include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene oleyl ether and polyoxyethylene cetyl ether, polyoxyethylene fatty acid diether, polyoxyethylene fatty acid monoether, and polyoxyethylene-polyoxypropylene block polymer; acetylene glycol derivatives such as acetylene alcohol, acetylene glycol, polyethoxyate of acetylene alcohol, and polyethoxyate of acetylene glycol; silicone-containing surfactants such as Fluorad ([Trademark], manufactured by Sumitomo 3M Limited), MEGAFAC ([Trademark], manufactured by DIC Corporation), and Surufuron ([Trademark], manufactured by Asahi Glass Co., Ltd.); and organosiloxane surfactants such as KP341 ([Trademark], manufactured by Shin-Etsu Chemical Co., Ltd.). The acetylene glycols listed above include 3-methyl-1-butyne-3-ol, 3-methyl-1-pentin-3-ol, 3,6-dimethyl-4-octin-3,6-diol, 2,4,7,9-tetramethyl-5-decine-4,7-diol, 3,5-dimethyl-1-hexyn-3-ol, 2,5-dimethyl-3-hexyn-2,5-diol, and 2,5-dimethyl-2,5-hexanediol.

[0066] Examples of anionic surfactants include ammonium and organic amine salts of alkyldiphenyl ether disulfonic acid, ammonium and organic amine salts of alkyldiphenyl ether sulfonic acid, ammonium and organic amine salts of alkylbenzene sulfonic acid, ammonium and organic amine salts of polyoxyethylene alkyl ether sulfate, and ammonium and organic amine salts of alkyl sulfate. Furthermore, examples of amphoteric surfactants include 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolium betaine and lauryl amidopropyl hydroxysulfone betaine.

[0067] These surfactants may be used individually or in combination of two or more. Their amount is typically 50 to 2000 ppm, preferably 100 to 1000 ppm, based on the polymerizable composition of the present invention. If necessary, sensitizers may be incorporated into the polymerizable compositions of the present invention. Examples of sensitizers preferably used in the compositions of the present invention include coumarin, ketocoumarin, their derivatives, thiopyrillium salts, and acetophenone. Specifically, the examples are p-bis(o-methylstyryl)benzene, 7-dimethylamino-4-methylquinolone-2,7-amino-4-methylcoumarin, 4,6-dimethyl-7-ethylaminocoumarin, 2-(p-dimethylaminostyryl)pyridyliodide methyl, 7-diethylaminocoumarin, 7-diethylamino-4-methylcoumarin, 2,3,5,6-1H,4H-tetrahydro-8-methylquinolidino-<9,9a,1-gh>coumarin, 7-diethylamino-4-trifluoromethylcoumarin, 7-dimethylamino-4-trifluoromethylcoumarin, 7-amino-4-trifluoromethylcoumarin, 2,3,5,6-1H,4H-tetrahydroquinolidino<9,9a,1-gh>coumarin, 7-E This includes tylamino-6-methyl-4-trifluoromethylcoumarin, 7-ethylamino-4-trifluoromethylcoumarin, 2,3,5,6-1H,4H-tetrahydro-9-carboethoxyquinolidino-<9,9a,1-gh>coumarin, 3-(2'-N-methylbenzimidazolyl)-7-N,N-diethylaminocoumarin, N-methyl-4-trifluoromethylpiperidino-<3,2-g>coumarin, 2-(p-dimethylaminostyryl)benzothiazolylethyliodide, 3-(2'-benzimidazolyl)-7-N,N-diethylaminocoumarin, 3-(2'-benzothiazolyl)-7-N,N-diethylaminocoumarin, and pyrylium or thiopyrillium salts represented by the following formulas. [ka]

[0068] The added infection agent enables patterning using inexpensive light sources such as high-pressure mercury lamps (360-430 nm). The amount is preferably 0.05 to 15 parts by weight, more preferably 0.1 to 10 parts by weight, based on 100 parts by weight of the organic polysilicon compound of the present invention. As a sensitizer, it is also feasible to employ a compound having an anthracene skeleton, for example, as disclosed in WO2012 / 059331 A1 or JP3820633B. When an anthracene skeleton-containing sensitizer is added, the amount is preferably 0.01 to 5 parts by weight, based on 100 parts by weight of the organic polysilicon compound of the present invention.

[0069] Furthermore, if necessary, stabilizers may be added to the compositions of the present invention. Stabilizers can be freely selected from those that are generally known. However, in the present invention, aromatic amines are preferred because they have a high stabilizing effect. Among these aromatic amines, pyridine derivatives are preferred, and pyridine derivatives having bulky substituents at the 2 and 6 positions are particularly preferred. Specific examples are as follows: [ka]

[0070] In a more preferred embodiment of this aspect of the present invention, at least one further functional material is an optically transparent polymer. In accordance with the present invention, a wide variety of publicly known transparent matrix materials suitable for optical devices can preferably be used as optically transparent polymers. As used herein, the term “transparent” means at least about 60% of the incident light transmitted through the thickness used in the optical medium and the wavelength or wavelength range used during the operation of the optical medium. Preferably, it is greater than 70%, more preferably greater than 75%, and most preferably greater than 80%.

[0071] In a preferred embodiment of the present invention, the optically transparent polymer is a transparent matrix material. As used herein, the term “polymer” means a material having repeating units and having a weight-average molecular weight (Mw) of 1000 g / mol or more. The molecular weight Mw is determined by GPC (= gel permeation chromatography) against an internal polystyrene standard. In a more preferred embodiment of the present invention, the glass transition temperature (Tg) of the clear polymer is 70°C or higher and 250°C or lower.

[0072] Tg is measured based on the change in heat capacity observed by differential scanning calorimetry, as described in http: / / pslc.ws / macrog / dsc.htm; Rickey J Seyler, Assignment of the Glass Transition, ASTM publication code number (PCN) 04-012490-50, etc. For example, poly(meth)acrylates, epoxys, polyurethanes, or polysiloxanes can be preferably used as transparent polymers for transparent matrix materials. More preferably, the weight-average molecular weight (Mw) of the polymer as a transparent matrix material is in the range of 1,000 to 300,000 g / mol, and more preferably 10,000 to 250,000 g / mol.

[0073] In further aspects, the present invention also relates to compounds represented by chemical formula (I) as defined herein, or compounds represented by chemical formula (III) as defined herein, or compounds represented by formula (IV), (Va), or (Vb) as defined herein, and The present invention provides a composition comprising at least one further functional material, preferably selected from the group consisting of organic light-emitting materials, inorganic light-emitting materials, charge transport materials, host or matrix materials, optically transparent polymers, antioxidants or stabilizers, radical quenchers, photoinitiators or polymerization initiators, wetting and dispersing agents, scattering particles, refractive index modifiers, developer dissolution accelerators, scum removers, adhesion enhancers, polymerization inhibitors, defoamers, surfactants, and sensitizers. Preferred examples of further functional materials as defined above are equally preferred in this context.

[0074] In preferred embodiments of compositions according to this aspect of the present invention, at least one further functional material is a host or matrix material, which is more preferably selected from (meth)acrylate monomers or polymers. A (meth)acrylate monomer represented by the following chemical formula (VII) is particularly preferred. In another aspect, the present invention also relates to semiconducting luminescent nanoparticles having at least a core and optionally one or more shell layers, a compound represented by chemical formula (I) as defined herein, [ka] The present invention also provides compositions comprising at least one further functional material, preferably selected from the group consisting of organic light-emitting materials, inorganic light-emitting materials, charge transport materials, host or matrix materials, optically transparent polymers, antioxidants or stabilizers, radical quenchers, photoinitiators or polymerization initiators, wetting and dispersing agents, scattering particles, refractive index modifiers, developer dissolution accelerators, scum removers, adhesion enhancers, polymerization inhibitors, defoamers, surfactants, and sensitizers.

[0075] Preferred examples of further functional materials as defined above are equally preferred in this context. As the inorganic portion of the semiconducting luminescent nanoparticles included in the composition according to this aspect of the present invention, a wide variety of publicly known semiconducting luminescent nanoparticles may be used as desired. In particular, the type of shape of the semiconducting luminescent nanoparticles, their core, and any one or more shell layers may be as defined above with respect to the semiconducting luminescent nanoparticles of the present invention. In addition, the outermost surface of the core or shell layer of the semiconducting luminescent nanoparticles contained in a composition according to this aspect of the present invention may be coated with a different type of compound or ligand, as defined above with respect to the semiconducting luminescent nanoparticles of the present invention.

[0076] In a preferred embodiment of a composition according to this aspect of the present invention, at least one further functional material is a host or matrix material more preferably selected from (meth)acrylate monomers or polymers. (Meth)acrylate monomer is preferably the following chemical formula (VII) [ka] During the ceremony, R 4 This is a linear alkylene chain or alkoxylene chain having 1 to 15 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms. k is either 0 or 1. R 5 This is a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, and one or more radicals R b It may also be replaced by, Preferably, the cyclic alkyl or alkoxy group is a cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, and in each case, one or more radicals R b It may also be substituted by, where one or more non-adjacent CH2 groups are R b C=CR b , C≡C, Si(R b )2, Ge(R b )2, Sn(R b )2, C=O, C=S, C=Se, C=NR b , P(=O)(R b ), SO, SO2, NR b , OS, or CONR b It may be replaced by, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2,

[0077] R bEach occurrence is identical or different, H, D, or an alkyl group having 1 to 20 carbon atoms, a cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, an aromatic ring system having 5 to 60 carbon ring atoms, or a heteroaromatic ring system having 5 to 60 carbon atoms, where the H atom may be replaced by D, F, Cl, Br, or I, and where there are two or more adjacent substituents R b These may form mono- or polycyclic, aliphatic, aromatic, or heteroaromatic ring systems with each other, and R 6 is either H or CH3. It is represented as follows.

[0078] Specific preferred examples of (meth)acrylate monomers used as matrix materials in compositions according to this aspect of the present invention include lauryl acrylate (LA), lauryl methacrylate (LMA), 4-tert-butylcyclohexyl acrylate (TBCH), trimethylolpropane triacrylate (TMPTA), cyclohexyl methacrylate (CHMA), tripropylene glycol diacrylate (TPGDA), 1,6-hexanediol dimethacrylate (HDDMA), isobornyl acrylate (IBA), isobornyl methacrylate (IBMA), 1,9-nonanediol diacrylate (NDDA), or any combination of one or more of these. More preferably, the (meth)acrylate monomer represented by chemical formula (VII) used as the matrix material has a viscosity of 25 cP or less at 25°C, preferably 1 to 25 cP, more preferably 2 to 20 cP, and even more preferably 2 to 10 cP, and / or a boiling point (BP) of 180°C or higher, preferably in the range of 180°C to 350°C, more preferably 250°C to 350°C.

[0079] According to the present invention, the viscosity can be measured at room temperature using a vibrating viscometer VM-10A (SEKONIC). https: / / www.sekonic.co.jp / english / product / viscometer / vm / vm_series.html In a more preferred embodiment of a composition according to this aspect of the present invention, the compound represented by chemical formula (I) is the compound represented by chemical formula (III) as defined herein. [ka] This represents a compound represented by [this symbol]. In a more preferred embodiment of the composition according to this aspect of the present invention, in chemical formula (III), L is the chemical formula (II). [ka] Selected from, During the ceremony, L 1 teeth, [ka] is;

[0080] L 2 teeth, [ka] is; Here, the dashed lines represent the bonds to the remaining compound (i.e., L, L). 1 and L 2 The symbol "*" indicates a bond from base Y or base Z, and the symbol "*" indicates base L 1 and base L 2 Mark the bond between and here L 1 and L 2 Each of these is one or more base R a It may also be replaced by, where L 1 and L 2 One or more CH2 groups are -R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NRa , P(=O)(R a ), SO, SO2, NR a , or -C(=O)NR a - may be replaced by, and here L 1 and L 2 One or more H atoms in are divalent groups selected from the groups represented by D, F, Cl, Br, I, CN, or NO2; M 1 H is, And here the indices m and l and the symbol R a This is defined herein.

[0081] More preferably, in compositions according to this aspect of the present invention, L 1 teeth, [ka] [ka] is; L 2 teeth, [ka] That is the case.

[0082] In a specifically preferred embodiment of a composition according to this aspect of the present invention, the compound represented by chemical formula (I) or (III) is a compound represented by chemical formula (Va) or (Vb), preferably (Va) [ka] This represents a compound represented by , In the formulas, the symbols and indices are as defined herein, and Z is N or O, and M 1 H is H. Specific preferred examples of compounds of chemical formula (Va) that may be included in compositions according to this aspect of the present invention are represented by the chemical formulas (V-1) to (V-6) defined above, where M 1 H is H.

[0083] A composition according to this aspect of the present invention more preferably contains the compound represented by chemical formula (I) in an amount of 1 to 50 wt.%, more preferably 5 to 40 wt.%, and even more preferably 10 to 30 wt.%, based on wt.% of the total weight of the composition. More preferably, a composition according to this aspect of the present invention contains, based on the total weight of the composition, 1 to 50 wt.%, more preferably 20 to 45 wt.%, and even more preferably 25 to 40 wt.%, of semiconducting luminescent nanoparticles (only the inorganic portion of the nanoparticles). The inventors have surprisingly found that when a bifunctional polymerizable acrylate-based compound represented by chemical formula (I) as defined herein is used as an additive added directly to a composition comprising semiconducting luminescent nanoparticles and at least one further functional material, preferably a host material or matrix material, more preferably selected from (meth)acrylate monomers or polymers as defined in relation to this aspect of the Invention, improved optical properties such as improved stability of nanoparticles and high luminescence efficiency can be achieved, even after film curing and / or film heating.

[0084] -Formulation To process semiconducting luminescent nanoparticles, compounds, or compositions according to the present invention from a liquid phase, for example by spin coating or printing, a formulation containing the nanoparticles, compounds, or compositions of the present invention is required. These formulations may be, for example, solutions, dispersions, or emulsions.

[0085] Accordingly, the present invention further relates to a formulation comprising a semiconducting luminescent nanoparticle according to the present invention as defined herein, or a compound or composition according to the present invention as defined herein, and at least one solvent. Preferably, at least one solvent is selected from the group consisting of esters such as PGMEA (propylene glycol methyl ether acetate), ethyl acetate, butyl acetate, amyl acetate, ethylene carbonate, and methoxypropyl acetate; ketones such as methyl ethyl ketone (MEK), methyl isobutyl ketone, and cyclohexanone; glycols such as ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, triethylene glycol, glycol ethers, and hexylene glycol; ethers such as diethyl ether and tetrahydrofuran; alcohols such as methanol, ethanol, isopropanol, and butanol; or aromatic, halogenated, and aliphatic hydrocarbons such as toluene, xylene, chloroform, dichloromethane, and heptane. It is also preferable to use a mixture of two or more solvents.

[0086] The amount of solvent in the formulation can be freely controlled depending on the coating method. For example, when spray coating is used, the solvent can be included in an amount of 90 wt% or more. Furthermore, when using the slit coating method, which is often employed when coating large substrates, the solvent content is usually 60 wt% or more, preferably 70 wt% or more. Methods for preparing such formulations are known to those skilled in the art and are described, for example, in WO 2002 / 072714, WO 2003 / 019694 and the literature cited herein.

[0087] -use The present invention further relates to the use of semiconducting luminescent nanoparticles according to the present invention as defined herein, or compositions or formulations according to the present invention as defined herein, in electronic devices, optical devices, or biomedical devices. In another aspect, the present invention further relates to a compound represented by chemical formula (I) as defined herein, or a compound represented by chemical formula (III) as defined herein. The present invention relates to the use of semiconducting luminescent nanoparticles having at least a core and optionally one or more shell layers, and at least one further functional material, which is preferably selected from the group consisting of organic luminescent materials, inorganic luminescent materials, charge transport materials, host or matrix materials, optically transparent polymers, antioxidants or stabilizers, radical quenchers, photoinitiators or polymerization initiators, wetting and dispersing agents, scattering particles, refractive index modifiers, developer dissolution accelerators, scum removers, adhesion enhancers, polymerization inhibitors, defoamers, surfactants, and sensitizers, as additives in compositions.

[0088] More preferably, at least one further functional material is a host or matrix material, and even more preferably, is selected from (meth)acrylate monomers or polymers.

[0089] The definitions and preferred examples of further functional materials mentioned above in relation to the compositions of the present invention are also preferred in this use. The (meth)acrylate monomer is specifically preferably represented by chemical formula (VII) as defined above. As the inorganic portion of the semiconducting luminescent nanoparticles used in accordance with this aspect of the present invention, a wide variety of known semiconducting luminescent nanoparticles may be used as desired. In particular, the type of shape of the semiconducting luminescent nanoparticles and their core and any one or more shell layers may be as defined above in relation to the semiconducting luminescent nanoparticles of the present invention. In addition, the outermost surface of the core or shell layer(s) of the semiconducting luminescent nanoparticles contained in a composition according to this aspect of the present invention may be coated with a different type of compound as defined above in relation to the semiconducting luminescent nanoparticles of the present invention.

[0090] In a preferred embodiment of use according to this aspect of the present invention, the compound used is the compound of chemical formula (III) as defined herein. [ka] It is a compound represented by the following: During the ceremony L is selected from chemical formula (II), [ka] During the ceremony L 1 teeth, [ka] and L 2 teeth [ka] And, In the formula, the dashed line represents the bond to the remaining compound (i.e., L, L). 1 and L 2 The symbol "*" indicates a bond from base Y or base Z, and the symbol "*" indicates base L 1 and base L 2 Mark the bond between and here L 1 and L 2 Each of these is one or more base R a It may also be replaced by, where L 1 and L 2 One or more CH2 groups are -R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, NR a , or -C(=O)NR a - may be replaced by, and here L 1 and L 2 In this, one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, and,

[0091] M 1 H is, And here the indices m and l and the symbol R a The terms are defined above in relation to the compounds of the present invention. L 1 teeth [ka] [ka] And, Preferably, L 1 teeth, [ka] And, and L 2 teeth, [ka] That is the case.

[0092] In a more preferred embodiment of the use according to this aspect of the present invention, the compound represented by chemical formula (I) or (III) represents the compound represented by chemical formula (Va) or (Vb), preferably (Va): [ka] In the formula, the symbols and indices are as defined above with respect to the compounds of the present invention, and Z is N or O, and M 1 H is H.

[0093] Specific preferred examples of compounds represented by chemical formula (Va) used in accordance with this aspect of the present invention are those represented by chemical formulas (V-1) to (V-6) as defined above, where M 1 H is H.

[0094] -Optical media The present invention further relates to an optical medium comprising semiconducting luminescent nanoparticles according to the present invention as defined herein, or a composition or formulation according to the present invention as defined herein. In a preferred embodiment, the optical medium is an optical film, such as a color filter, a color conversion film, a remote phosphor tape, or another film or filter, more preferably a color conversion film, and even more preferably a pixelated color conversion film.

[0095] - Optical devices The present invention further relates to semiconducting light-emitting nanoparticles according to the present invention as defined herein, or compositions or formulations according to the present invention as defined herein, or optical devices comprising the optical medium of the present invention. In preferred embodiments of the present invention, the optical device is a liquid crystal display, an organic light-emitting diode (OLED), a backlight unit for a display, a light-emitting diode (LED), a micro-electromechanical system (MEMS), an electro-wet display, an electroluminescent quantum dot light-emitting diode (EL-Q-LED as described in US 2016 / 248029 A2, EP 2221355 A1), or an electrophoretic display, a lighting device, and / or a solar cell.

[0096] -process The present invention further provides a simple process for preparing the optical device of the present invention, the process comprising the following steps a) to c), preferably in this order: a) Semiconducting luminescent nanoparticles having a core and at least one shell layer, at least one further functional material, chemical formula (I) as defined below [ka] To prepare a mixture by mixing a compound represented by and optionally at least one solvent; Providing a mixture onto a b-substrate; c) The obtained mixture is subjected to light irradiation having a peak light wavelength in the range of 300 to 650 nm, preferably 320 to 520 nm, more preferably 350 nm to 500 nm, and even more preferably 360 nm to 470 nm.

[0097] Preferred embodiments of the compound, symbol, and index represented by chemical formula (I) mentioned above in relation to the semiconducting luminescent nanoparticles according to the present invention are also preferred embodiments in this process. In particular, compounds represented by chemical formula (III) as defined above, and compounds represented by chemical formulas (IV), (Va), and (Vb) as defined above are preferred. Embodiments represented by chemical formulas (IV-1) to (IV-6) and (V-1) to (V-6) as defined above are even more specifically preferred. According to an aspect of the process for preparing an optical device in accordance with the present invention, the compound represented by chemical formula (I) as defined herein is first mixed with the semiconducting luminescent nanoparticles before being mixed with at least one further functional material and any at least one solvent.

[0098] According to another aspect of the process for preparing an optical device according to the present invention, semiconducting luminescent nanoparticles, at least one further functional material, and any at least one solvent are first mixed before adding and mixing with the compound represented by chemical formula (I) as defined herein. Preferably, according to this aspect of the process of the present invention, the compound represented by chemical formula (I) is added in an amount of 1 to 50 wt.%, more preferably 5 to 40 wt.%, and even more preferably 10 to 30 wt.%, based on the total weight of the composition (excluding the solvent).

[0099] At least one further functional material is preferably selected from the group consisting of organic light-emitting materials, inorganic light-emitting materials, charge transport materials, host or matrix materials, optically transparent polymers, antioxidants or stabilizers, radical quenchers, photoinitiators or polymerization initiators, wetting and dispersing agents, scattering particles, refractive index modifiers, developer dissolution accelerators, scum removers, adhesion enhancers, polymerization inhibitors, defoamers, surfactants, and sensitizers. Preferably, at least one further functional material is a host or matrix material, more preferably selected from (meth)acrylate monomers or polymers. In the process for preparing optical devices according to the present invention, (meth)acrylate monomers represented by the chemical formula (VII) defined above are particularly preferred.

[0100] Preferred examples of further functional materials as defined above in the "Compositions" section are also preferred in this context. At least one solvent optionally added according to the process for preparing an optical device according to the present invention is preferably selected from the group consisting of esters such as PGMEA (propylene glycol methyl ether acetate), ethyl acetate, butyl acetate, amyl acetate, ethylene carbonate, and methoxypropyl acetate; ketones such as methyl ethyl ketone (MEK), methyl isobutyl ketone, and cyclohexanone; glycols such as ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, triethylene glycol, glycol ethers, and hexylene glycol; ethers such as diethyl ether and tetrahydrofuran; alcohols such as methanol, ethanol, isopropanol, and butanol; or aromatic, halogenated, and aliphatic hydrocarbons such as toluene, xylene, chloroform, dichloromethane, and heptane.

[0101] The light source for light irradiation in step (c) is preferably selected from one or more artificial light sources, and is preferably selected from light-emitting diodes, organic light-emitting diodes, cold cathode fluorescent lamps, or laser devices. The mixture obtained in step a) may be sealed in a clear container such as a vial. In a preferred embodiment of the present invention, steps a), b), and / or c) are carried out under inert conditions, such as a nitrogen (N2) or argon (Ar) atmosphere. More preferably, all of steps a) and b), and optionally step c), are carried out under these inert conditions. In step c), the irradiation intensity of the light (i.e., the total luminous flux incident on the surface) is 0.25 to 100 mW / cm². 2 It is preferably in the range of 0.5 to 50 mW / cm², and more preferably in the range of 0.5 to 50 mW / cm². 2 It is within the range of [the specified range].

[0102] In accordance with the present invention, any known type of coating method can preferably be used to provide a photosensitive composition to a substrate according to step a). For example, dipping coating, gravure coating, roll coating, bar coating, brush coating, spray coating, doctor coating, flow coating, spin coating, and slit coating. The substrate is not particularly limited and can be appropriately selected from, for example, silicon substrates, glass substrates, polymer films, etc., and each may be flexible, semi-rigid, or rigid. Preferably, a transparent substrate is used. Known transparent substrates suitable for optical devices may be used as desired.

[0103] Preferably, transparent substrates can include transparent polymer substrates, glass substrates, thin glass substrates laminated on transparent polymer films, and transparent metal oxides (e.g., silicone oxide, aluminum oxide, titanium oxide). A heating step (preheating treatment) may be optionally performed before the light irradiation step and after the step of supplying the mixture onto the substrate, if necessary. Preheating is carried out using a hot plate, oven, furnace or similar device at a temperature of preferably 50 to 150°C, more preferably 90 to 150°C, for 10 seconds to 30 minutes, preferably 10 seconds to 5 minutes.

[0104] Furthermore, a post-irradiation heating step may be optionally performed after the light irradiation step, if necessary. Post-irradiation heating is carried out using a hot plate, oven, furnace or similar device, at a temperature of preferably 40-150°C, more preferably 60-120°C, for 10 seconds to 10 minutes, more preferably 20 seconds to 5 minutes. In a more preferred embodiment of the present invention, step c) is performed at a temperature of 70°C or less, preferably in the range of 60°C to 0°C, more preferably in the range of 50°C to 20°C, and / or for a period of time from 1 second to 1 hour, preferably from 10 seconds to 30 minutes, more preferably from 1 minute to 15 minutes.

[0105] Preferred embodiment 1. Core, optionally one or more shell layers, and chemical formula (I) [ka] During the ceremony o is 1, 2, or 3, preferably 1; R 1 This includes H, D, CN, a linear alkyl or alkoxy group having 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more R groups). a It may also be substituted by, where in each case one or more CH2 groups are R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a- may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); Aromatic ring systems or heteroaromatic ring systems having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a (These may be substituted by D, F, Cl, Br, I, CN or NO2, where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); R 2 , R 3 These are: a linear alkyl or alkoxy group having H, D, CN, and 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more R groups). a It may also be substituted by, where in each case one or more CH2 groups are R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); or an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a (These may be substituted by D, F, Cl, Br, I, CN or NO2, where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2);

[0106] A1 teeth, [ka] and n=0 or 1; Y is O, N, or S, preferably O or N; A 2 This refers to an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a It may be substituted by a divalent group selected from D, F, Cl, Br, I, CN, NO2, where one or more H atoms in the aromatic or heteroaromatic ring system may be replaced by D, F, Cl, Br, I, CN, NO2;

[0107] R a Each occurrence may be the same or different, and the groups are: a linear alkyl or alkoxy group having H, D, and 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms); a linear alkenyl or alkynyl group having 2 to 40 carbon atoms (preferably 2 to 24 carbon atoms, more preferably 2 to 12 carbon atoms); a branched alkenyl or alkynyl group having 3 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 3 to 12 carbon atoms); and an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (wherein one or more H atoms in each of the above groups may be replaced by D, F, Cl, Br, I, and wherein two or more adjacent substituents R a (These elements may form any monocyclic or polycyclic aliphatic ring system with each other;

[0108] L is a linear alkylene group having 1 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms); a linear alkenylene or alkynylene group having 2 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); or a branched alkenylene or alkynylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms) (each of which is one or more groups R a Each of these may be substituted by, and in each case one or more CH2 groups are arylene groups or heteroarylene groups having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), aralkylene group, heteroaralkylene group, alkylarylene group or alkylheteroarylene group (each of which is one or more groups R a (which may be substituted by, and in each case one or more H atoms may be replaced by D, F, Cl, Br, I, CN, NO2), or the following chemical formula (II) [ka]

[0109] During the ceremony m is an integer between 1 and 50, preferably between 1 and 25, more preferably between 2 and 20, and even more preferably between 4 and 12; l is an integer between 1 and 25, preferably between 1 and 20, more preferably between 1 and 12, and even more preferably between 1 and 8; L 1 teeth, [ka] is; L 2 teeth, [ka] is;

[0110] Here, the dashed line indicates the bond to the rest of the compound, and the symbol "*" indicates the group L 1 and base L 2 Mark the bond between and here L 1 and L 2 Each of these is one or more base R a It may also be replaced by, where L 1 and L 2 One or more CH2 groups are -R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, NR a , or -C(=O)NR a - may be replaced by, and here L 1 and L 2 One or more H atoms in are divalent groups selected from the groups represented by D, F, Cl, Br, I, CN, or NO2; X 1 These are the same or different in each occurrence, -COOM 1 ,-PO(OH)(OM 1 ), -PO(OM1 )2, -OC(S)SM 1 -NH2, -NHR a , -N(R a )2, -SO3M 1 -SM 1 ,-Ar 1 -SM 1 , -OCO-A 3 -SM 1 ,-COO-A 3 -SM 1 ,-NCO-A 3 -SM 1 , OSIOR a , or -N(CS2M 1 ) an anchor group preferably selected from 2;

[0111] Ar 1 This is a divalent group selected from an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), each of which has one or more groups R a It may be substituted by, and here one or more H atoms of the aromatic or heteroaromatic ring system may be replaced by D, F, Cl, Br, I, CN, NO2;

[0112] A 3 This includes a linear alkylene group having 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms), and a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more groups R a They may be substituted with Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a- may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring systems or heteroaromatic ring systems having 5 to 25 aromatic ring atoms (preferably 5 to 18 aromatic ring atoms, more preferably 5 to 12 aromatic ring atoms) (each of which has one or more groups R a It may be substituted by a divalent group selected from D, F, Cl, Br, I, CN, NO2, where one or more H atoms in the aromatic or heteroaromatic ring system are replaced by D, F, Cl, Br, I, CN, NO2;

[0113] M 1 is a hydrogen atom, or 1 / 2 Mg 2+ , 1 / 2 Cu 2+ , 1 / 2 Zn 2+ , 1 / 2 Pb 2+ , 1 / 2 Sn 2+ , 1 / 2 Cd 2+ , 1 / 3 Bi 3+ , or 1 / 4 Sn 4+ A metal cation selected from, preferably a hydrogen atom, 1 / 2 Mg 2+ , 1 / 2 Cu 2+ , or 1 / 2 Zn 2+ More preferably, showing hydrogen atoms, Semiconducting luminescent nanoparticles containing a compound represented by [formula].

[0114] 2.In chemical formula (I) A 1 but [ka] The semiconducting luminescent nanoparticle according to embodiment 1, wherein Y is as defined above.

[0115] 3.In chemical formula (I) X 1 However, each occurrence is either the same or different, -OC(S)SM 1 -SM 1 ,-Ar 1 -SM 1 , -OCO-A 3-SM 1 ,-COO-A 3 -SM 1 ,-NCO-A 3 -SM 1 , or -N(CS2M 1 ) Selected from 2; Here Ar 1 , A 3 and M 1 However, as defined in Embodiment 1, Semiconducting luminescent nanoparticles according to embodiment 1 or 2.

[0116] 4.In chemical formula (I) A 1 but [ka] and X 1 However, each occurrence is either the same or different, -OC(S)SM 1 -SM 1 ,-Ar 1 -SM 1 , -OCO-A 3 -SM 1 ,-COO-A 3 -SM 1 ,-NCO-A 3 -SM 1 , or -N(CS2M 1 ) Selected from 2; Here, Y, Ar 1 , A 3 and M 1 However, as defined in Embodiment 1, Semiconducting luminescent nanoparticles according to any one of embodiments 1 to 3.

[0117] 5.In chemical formula (I), L is a linear alkylene group having 1 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms); a linear alkenylene or alkynylene group having 2 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); or a branched alkenylene or alkynylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms) (each of which is one or more groups R a Each of these may be substituted by, and in each case one or more CH2 groups are arylene groups or heteroarylene groups having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), aralkylene group, heteroaralkylene group, alkylarylene group or alkylheteroarylene group (each of which is one or more groups R a (which may be substituted by, and in each case one or more H atoms may be replaced by D, F, Cl, Br, I, CN, NO2), or the following chemical formula (II) [ka] L in the ceremony 1 teeth, [ka] [ka] is; and L 2 teeth, [ka] Here, m, l and R a This is as defined in Embodiment 1, Semiconducting luminescent nanoparticles according to any one of embodiments 1 to 4, selected from the above.

[0118] 6. In chemical formula (I), A 1 teeth [ka] is; L is a linear alkylene group having 1 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms); a linear alkenylene or alkynylene group having 2 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); or a branched alkenylene or alkynylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms) (each of which is one or more groups R a Each of these may be substituted by, and in each case one or more CH2 groups are arylene groups or heteroarylene groups having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a-C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), aralkylene group, heteroaralkylene group, alkylarylene group or alkylheteroarylene group (each of which is one or more groups R a (which may be substituted by, and in each case one or more H atoms may be replaced by D, F, Cl, Br, I, CN, NO2), or the following chemical formula (II) [ka] During the ceremony

[0119] L 1 teeth [ka] [ka] And preferably L 1 teeth, [ka] is; L 2 teeth, [ka] is; and

[0120] X 1 This is the same or different in each occurrence, -OC(S)SM 1 -SM 1 ,-Ar 1 -SM 1 , -OCO-A 3 -SM 1 ,-NCO-A 3 -SM1 ,-COO-A 3 -SM 1 , or -N(CS2M 1 ) Selected from 2, Here, m, l, Y, R a Ar 1 , A 3 and M 1 This is as defined in Embodiment 1, Semiconducting luminescent nanoparticles according to any one of embodiments 1 to 5, selected from the above.

[0121] 7. The compound represented by chemical formula (I) is the same as the following chemical formula (III) [ka] The symbols present in the formula are defined in any one of the embodiments 1 to 6, and In the formula, Z is either N or O. A semiconducting luminescent nanoparticle according to any one of embodiments 1 to 6, representing a compound represented by [the specified formula].

[0122] 8. The compound represented by chemical formula (I) is the same as the following chemical formulas (IV), (Va), or (Vb) [ka] The symbols and indices present in the formula are as defined in any one of embodiments 1 to 7, and j is an integer between 1 and 40, preferably 3 to 24, more preferably 4 to 12. A semiconducting luminescent nanoparticle according to any one of embodiments 1 to 7, representing a compound represented by [the specified formula].

[0123] 9. The compound represented by chemical formula (I) is the same as the following chemical formulas (IV-1) to (IV-6) and (V-1) to (V-6) [ka] [ka] [ka] The symbols and indices present in the formula have the meanings defined in any one of embodiments 1 to 8, and the indices g and f are either the same or different, and are integers between 1 and 40, preferably 3 and 24, more preferably 4 and 12. A semiconducting luminescent nanoparticle according to any one of embodiments 1 to 8, representing a compound represented by one of the following.

[0124] 10. Semiconducting luminescent nanoparticle according to any one of embodiments 1 to 9, wherein the compound represented by chemical formula (I) has a molecular weight in the range of 150 to 2000 Da, more preferably 150 to 1500 Da, and even more preferably 200 to 1000 Da.

[0125] 11.General formula (III) [ka] During the ceremony, Y is O, N, or S, preferably O or N; Z is either O or N; R 1 This includes H, D, CN, a linear alkyl or alkoxy group having 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more R groups). a It may also be substituted by, where in each case one or more CH2 groups are R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a- may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); Aromatic ring systems or heteroaromatic ring systems having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a (These may be substituted by D, F, Cl, Br, I, CN or NO2, where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2);

[0126] R 2 , R 3 These are: a linear alkyl or alkoxy group having H, D, CN, and 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more R groups). a It may also be substituted by, where in each case one or more CH2 groups are R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); or an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a (These may be substituted by D, F, Cl, Br, I, CN or NO2, where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2);

[0127] R a Each occurrence may be the same or different, and the groups are: a linear alkyl or alkoxy group having H, D, and 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms); a linear alkenyl or alkynyl group having 2 to 40 carbon atoms (preferably 2 to 24 carbon atoms, more preferably 2 to 12 carbon atoms); a branched alkenyl or alkynyl group having 3 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 3 to 12 carbon atoms); and an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (wherein one or more H atoms in each of the above groups may be replaced by D, F, Cl, Br, I, and wherein two or more adjacent substituents R a (These elements may form any monocyclic or polycyclic aliphatic ring system with each other;

[0128] L is a linear alkylene group having 1 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms); a linear alkenylene or alkynylene group having 2 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); or a branched alkenylene or alkynylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms) (each of which is one or more groups R a Each of these may be substituted by, and in each case one or more CH2 groups are arylene groups or heteroarylene groups having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), Si(R a )2, Ge(R a)2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), aralkylene group, heteroaralkylene group, alkylarylene group or alkylheteroarylene group (each of which is one or more groups R a (which may be substituted by, and in each case one or more H atoms may be replaced by D, F, Cl, Br, I, CN, NO2), or the following chemical formula (II) [ka]

[0129] During the ceremony, m is an integer between 1 and 50, preferably between 1 and 25, more preferably between 2 and 20, and even more preferably between 4 and 12. l is an integer between 1 and 25, preferably 1 and 20, more preferably 1 and 12, and even more preferably 1 and 8. L 1 teeth, [ka] is;

[0130] L 2 teeth, [ka] is; Here, the dashed line indicates the bond to the rest of the compound, and the symbol "*" indicates the group L 1 and base L 2 Mark the bond between and here L1 and L 2 Each of these is one or more base R a It may also be replaced by, where L 1 and L 2 One or more CH2 groups are -R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, NR a , or -C(=O)NR a - may be replaced by, and here L 1 and L 2 One or more H atoms in are divalent groups selected from the groups represented by D, F, Cl, Br, I, CN, or NO2;

[0131] A 3 This includes a linear alkylene group having 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms), and a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more groups R a They may be substituted with Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a- may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring systems or heteroaromatic ring systems having 5 to 25 aromatic ring atoms (preferably 5 to 18 aromatic ring atoms, more preferably 5 to 12 aromatic ring atoms) (each of which has one or more groups R a It may be substituted by a divalent group selected from D, F, Cl, Br, I, CN, NO2, where one or more H atoms in the aromatic or heteroaromatic ring system are replaced by D, F, Cl, Br, I, CN, NO2; And,

[0132] M 1 is a hydrogen atom, or 1 / 2 Mg 2+ , 1 / 2 Cu 2+ , 1 / 2 Zn 2+ , 1 / 2 Pb 2+ , 1 / 2 Sn 2+ , 1 / 2 Cd 2+ , 1 / 3 Bi 3+ , or 1 / 4 Sn 4+ A metal cation selected from, preferably a hydrogen atom, 1 / 2 Mg 2+ , 1 / 2 Cu 2+ , or 1 / 2 Zn 2+ More preferably, showing hydrogen atoms, A compound represented by the formula.

[0133] 12. The compound is of the following chemical formulas: (IV), (Va), or (Vb) [ka] In the formula, j is an integer between 1 and 40, preferably between 3 and 24, and more preferably between 4 and 12. The compound described in embodiment 11, which is represented by one of the following.

[0134] 13. Nanoparticles according to any one of the embodiments 1 to 10, At least one further functional material, which is preferably selected from the group consisting of organic light-emitting materials, inorganic light-emitting materials, charge transport materials, host or matrix materials, optically transparent polymers, antioxidants or stabilizers, radical quenchers, photoinitiators or polymerization initiators, wetting and dispersing agents, scattering particles, refractive index modifiers, developer dissolution accelerators, scum removers, adhesion enhancers, polymerization inhibitors, defoamers, surfactants, and sensitizers. A composition containing the following:

[0135] 14. Compounds described in embodiment 11 or 12, and At least one further functional material, which is preferably selected from the group consisting of organic light-emitting materials, inorganic light-emitting materials, charge transport materials, host or matrix materials, optically transparent polymers, antioxidants or stabilizers, radical quenchers, photoinitiators or polymerization initiators, wetting and dispersing agents, scattering particles, refractive index modifiers, developer dissolution accelerators, scum removers, adhesion enhancers, polymerization inhibitors, defoamers, surfactants, and sensitizers. A composition containing the following:

[0136] 15. Semiconducting luminescent nanoparticle having a core and at least one shell layer, chemical formula (I) [ka] During the ceremony, o is 1, 2, or 3, preferably 1; R 1 This includes H, D, CN, a linear alkyl or alkoxy group having 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more R groups). a It may also be substituted by, where in each case one or more CH2 groups are R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a)2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); Aromatic ring systems or heteroaromatic ring systems having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a (These may be substituted by D, F, Cl, Br, I, CN or NO2, where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2);

[0137] R 2 , R 3 These are: a linear alkyl or alkoxy group having H, D, CN, and 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more R groups). a It may also be substituted by, where in each case one or more CH2 groups are R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a- may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); or an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a (These may be substituted by D, F, Cl, Br, I, CN or NO2, where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); A 1 teeth, [ka] That is,

[0138] n=0 or 1, Y is O, N, S, preferably O or N. A 2 This refers to an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a It may be substituted by a divalent group selected from D, F, Cl, Br, I, CN, NO2, where one or more H atoms in the aromatic or heteroaromatic ring system may be replaced by D, F, Cl, Br, I, CN, NO2;

[0139] R aEach occurrence may be the same or different, and the groups are: a linear alkyl or alkoxy group having H, D, and 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms); a linear alkenyl or alkynyl group having 2 to 40 carbon atoms (preferably 2 to 24 carbon atoms, more preferably 2 to 12 carbon atoms); a branched alkenyl or alkynyl group having 3 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 3 to 12 carbon atoms); and an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (wherein one or more H atoms in each of the above groups may be replaced by D, F, Cl, Br, I, and wherein two or more adjacent substituents R a (These elements may form any monocyclic or polycyclic aliphatic ring system with each other;

[0140] L is a linear alkylene group having 1 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms); a linear alkenylene or alkynylene group having 2 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); or a branched alkenylene or alkynylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms) (each of which is one or more groups R a Each of these may be substituted by, and in each case one or more CH2 groups are arylene groups or heteroarylene groups having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), Si(R a )2, Ge(R a )2, Sn(R a)2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), aralkylene group, heteroaralkylene group, alkylarylene group or alkylheteroarylene group (each of which is one or more groups R a (which may be substituted by, and in each case one or more H atoms may be replaced by D, F, Cl, Br, I, CN, NO2), or the following chemical formula (II) [ka]

[0141] During the ceremony, m is an integer between 1 and 50, preferably between 1 and 25, more preferably between 2 and 20, and even more preferably between 4 and 12; l is an integer between 1 and 25, preferably between 1 and 20, more preferably between 1 and 12, and even more preferably between 1 and 8; L 1 teeth, [ka] is; L 2 teeth, [ka] is;

[0142] Here, the dashed line indicates the bond to the rest of the compound, and the symbol "*" indicates the group L 1 and base L 2 Mark the bond between and here L 1 and L2 Each of these is one or more base R a It may also be replaced by, where L 1 and L 2 One or more CH2 groups are -R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, NR a , or -C(=O)NR a - may be replaced by, and here L 1 and L 2 One or more H atoms in are divalent groups selected from the groups represented by D, F, Cl, Br, I, CN, or NO2; X 1 These are the same or different in each occurrence, -COOM 1 ,-PO(OH)(OM 1 ), -PO(OM 1 )2, -OC(S)SM 1 -NH2, -NHR a , -N(R a )2, -SO3M 1 -SM 1 ,-Ar 1 -SM 1 , -OCO-A 3 -SM 1 ,-COO-A 3 -SM 1 ,-NCO-A 3 -SM 1 , OSIOR a , or -N(CS2M 1 ) an anchor group preferably selected from 2;

[0143] Ar 1 This is a divalent group selected from an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), each of which has one or more groups Ra It may be substituted by, and here one or more H atoms of the aromatic or heteroaromatic ring system may be replaced by D, F, Cl, Br, I, CN, NO2; A 3 This includes a linear alkylene group having 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms), and a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more groups R a They may be substituted with Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring systems or heteroaromatic ring systems having 5 to 25 aromatic ring atoms (preferably 5 to 18 aromatic ring atoms, more preferably 5 to 12 aromatic ring atoms) (each of which has one or more groups R a It may be substituted by a divalent group selected from D, F, Cl, Br, I, CN, NO2, where one or more H atoms in the aromatic or heteroaromatic ring system are replaced by D, F, Cl, Br, I, CN, NO2;

[0144] M 1 is a hydrogen atom, or 1 / 2 Mg 2+ , 1 / 2 Cu 2+ , 1 / 2 Zn 2+ , 1 / 2 Pb 2+ , 1 / 2 Sn 2+ , 1 / 2 Cd 2+ , 1 / 3 Bi 3+ , or 1 / 4 Sn 4+ A metal cation selected from, preferably a hydrogen atom, 1 / 2 Mg2+ , 1 / 2 Cu 2+ , or 1 / 2 Zn 2+ More preferably, showing hydrogen atoms, Compounds represented by; and

[0145] At least one further functional material, which is preferably selected from the group consisting of organic light-emitting materials, inorganic light-emitting materials, charge transport materials, host or matrix materials, optically transparent polymers, antioxidants or stabilizers, radical quenchers, photoinitiators or polymerization initiators, wetting and dispersing agents, scattering particles, refractive index modifiers, developer dissolution accelerators, scum removers, adhesion enhancers, polymerization inhibitors, defoamers, surfactants, and sensitizers. A composition containing the following:

[0146] 16. The compound represented by chemical formula (I) is the same as the following chemical formula (III) [ka] In the formula, Z is either N or O. The composition according to embodiment 15, which represents a compound represented by [the specified compound].

[0147] 17. L is chemical formula (II) [ka] L 1 teeth, [ka] is; L 2 teeth, [ka] is;

[0148] Here, the dashed line indicates the bond to the rest of the compound, and the symbol "*" indicates the group L 1 and base L 2 Mark the bond between and here L 1 and L 2Each of these is one or more base R a It may also be replaced by, where L 1 and L 2 One or more CH2 groups are -R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, NR a , or -C(=O)NR a - may be replaced by, and here L 1 and L 2 One or more H atoms in may be replaced by D, F, Cl, Br, I, CN or NO2, selected from the groups represented by M 1 H is m, l, and R a The composition is as defined in Embodiment 15.

[0149] 18. The composition according to any one of embodiments 15 to 17, wherein the composition contains a compound represented by chemical formula (I) in an amount of 1 to 30 wt.% based on the total weight of the composition.

[0150] 19. The composition according to embodiment 13 or embodiment 14, or any one of embodiments 15 to 18, wherein at least one further functional material is a host or matrix material, preferably selected from (meth)acrylate monomers or polymers.

[0151] 20. Nanoparticles according to any one of embodiments 1 to 10, or compounds according to embodiment 11 or 12, or compositions according to any one of embodiments 13 to 19, At least one solvent, which is preferably selected from the group consisting of esters such as PGMEA (propylene glycol methyl ether acetate), ethyl acetate, butyl acetate, amyl acetate, ethylene carbonate, and methoxypropyl acetate; ketones such as methyl ethyl ketone (MEK), methyl isobutyl ketone, and cyclohexanone; glycols such as ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, triethylene glycol, glycol ethers, and hexylene glycol; ethers such as diethyl ether and tetrahydrofuran; alcohols such as methanol, ethanol, isopropanol, and butanol; or aromatic, halogenated, and aliphatic hydrocarbons such as toluene, xylene, chloroform, dichloromethane, and heptane. A compound containing the following:

[0152] 21. Use as an additive in a composition comprising the compound described in embodiment 11, a semiconducting light-emitting nanoparticle having at least a core and optionally one or more shell layers, and at least one further functional material.

[0153] 22. Use of nanoparticles according to any one of embodiments 1 to 10, a composition according to any one of embodiments 12 to 19, or a formulation according to embodiment 20 in an electronic device, an optical device, or a biomedical device.

[0154] 23. An optical medium comprising nanoparticles according to any one of embodiments 1 to 10, or a compound according to embodiment 11 or 12, or a composition according to any one of embodiments 12 to 19, or a formulation according to embodiment 20.

[0155] 24. An optical device comprising nanoparticles according to any one of embodiments 1 to 9, or a compound according to embodiment 10 or 11, or a composition according to any one of embodiments 12 to 15, or a formulation according to embodiment 16, or an optical medium according to embodiment 18.

[0156] 25. Steps a) to c): a) Preparing a mixture by mixing semiconducting luminescent nanoparticles having a core and at least one shell layer, at least one further functional material, a compound represented by the chemical formula (I) defined below, and at least one solvent; b) Providing the mixture onto the substrate; c) The resulting mixture is subjected to light irradiation having a peak light wavelength in the range of 300 to 650 nm, preferably 320 to 520 nm, more preferably 350 nm to 500 nm, and even more preferably 360 nm to 470 nm: [ka] During the ceremony, o is 1, 2, or 3, preferably 1;

[0157] R 1 This includes H, D, CN, a linear alkyl or alkoxy group having 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more R groups). a It may also be substituted by, where in each case one or more CH2 groups are R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a- may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); Aromatic ring systems or heteroaromatic ring systems having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a (These may be substituted by D, F, Cl, Br, I, CN or NO2, where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2);

[0158] R 2 , R 3 These are: a linear alkyl or alkoxy group having H, D, CN, and 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); and a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more R groups). a It may also be substituted by, where in each case one or more CH2 groups are R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); or an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a (These may be substituted by D, F, Cl, Br, I, CN or NO2, where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2);

[0159] A 1 teeth, [ka] is; n = 0 or 1; Y is O, N, or S, preferably O or N;

[0160] A 2 This refers to an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (each of which has one or more groups R a It may be substituted by a divalent group selected from D, F, Cl, Br, I, CN, NO2, where one or more H atoms in the aromatic or heteroaromatic ring system may be replaced by D, F, Cl, Br, I, CN, NO2; R a Each occurrence may be the same or different, and the groups are: a linear alkyl or alkoxy group having H, D, and 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms); a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms); a linear alkenyl or alkynyl group having 2 to 40 carbon atoms (preferably 2 to 24 carbon atoms, more preferably 2 to 12 carbon atoms); a branched alkenyl or alkynyl group having 3 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 3 to 12 carbon atoms); and an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms) (wherein one or more H atoms in each of the above groups may be replaced by D, F, Cl, Br, I, and wherein two or more adjacent substituents R a (These elements may form any monocyclic or polycyclic aliphatic ring system with each other;

[0161] L is a linear alkylene group having 1 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms); a linear alkenylene or alkynylene group having 2 to 40 carbon atoms (preferably 3 to 24 carbon atoms, more preferably 4 to 12 carbon atoms); or a branched alkenylene or alkynylene group having 3 to 40 carbon atoms (preferably 4 to 24 carbon atoms, more preferably 5 to 12 carbon atoms) (each of which is one or more groups R a Each of these may be substituted by, and in each case one or more CH2 groups are arylene groups or heteroarylene groups having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a - may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), aralkylene group, heteroaralkylene group, alkylarylene group or alkylheteroarylene group (each of which is one or more groups R a (which may be substituted by, and in each case one or more H atoms may be replaced by D, F, Cl, Br, I, CN, NO2), or the following chemical formula (II) [ka] During the ceremony,

[0162] m is an integer between 1 and 50, preferably between 1 and 25, more preferably between 2 and 20, and even more preferably between 4 and 12; l is an integer between 1 and 25, preferably between 1 and 20, more preferably between 1 and 12, and even more preferably between 1 and 8; L 1 teeth, [ka] is; L 2 teeth, [ka] is;

[0163] Here, the dashed line indicates the bond to the rest of the compound, and the symbol "*" indicates the group L 1 and base L 2 Mark the bond between and here L 1 and L 2 Each of these is one or more base R a It may also be replaced by, where L 1 and L 2 One or more CH2 groups are -R a C=CR a -, -C≡C-, Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, NR a , or -C(=O)NR a - may be replaced by, and here L 1 and L 2 One or more H atoms in are divalent groups selected from the groups represented by D, F, Cl, Br, I, CN, or NO2; X 1 In each occurrence, -COOM may be the same or different. 1 ,-PO(OH)(OM 1 ), -PO(OM 1)2, -OC(S)SM 1 -NH2, -NHR a , -N(R a )2, -SO3M 1 -SM 1 ,-Ar 1 -SM 1 , -OCO-A 3 -SM 1 ,-COO-A 3 -SM 1 ,-NCO-A 3 -SM 1 , OSIOR a , or -N(CS2M 1 )2 selected;

[0164] Ar 1 This is a divalent group selected from an aromatic ring system or heteroaromatic ring system having 5 to 40 aromatic ring atoms (preferably 5 to 25 aromatic ring atoms, more preferably 5 to 18 aromatic ring atoms), each of which has one or more groups R a It may be substituted by, and here one or more H atoms of the aromatic or heteroaromatic ring system may be replaced by D, F, Cl, Br, I, CN, NO2; A 3 This includes a linear alkylene group having 1 to 40 carbon atoms (preferably 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms), and a branched or cyclic alkylene group having 3 to 40 carbon atoms (preferably 3 to 25 carbon atoms, more preferably 3 to 15 carbon atoms) (each of which has one or more groups R a They may be substituted with Si(R a )2, Ge(R a )2, Sn(R a )2, C=O, C=S, C=Se, C=NR a , P(=O)(R a ), SO, SO2, -O-, NR a -C(=O)O-, or -C(=O)NR a- may be replaced by, and here one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2); aromatic ring systems or heteroaromatic ring systems having 5 to 25 aromatic ring atoms (preferably 5 to 18 aromatic ring atoms, more preferably 5 to 12 aromatic ring atoms) (each of which has one or more groups R a It may be substituted by a divalent group selected from D, F, Cl, Br, I, CN, NO2, where one or more H atoms in the aromatic or heteroaromatic ring system are replaced by D, F, Cl, Br, I, CN, NO2;

[0165] M 1 is a hydrogen atom, or 1 / 2 Mg 2+ , 1 / 2 Cu 2+ , 1 / 2 Zn 2+ , 1 / 2 Pb 2+ , 1 / 2 Sn 2+ , 1 / 2 Cd 2+ , 1 / 3 Bi 3+ , or 1 / 4 Sn 4+ A metal cation selected from, preferably a hydrogen atom, 1 / 2 Mg 2+ , 1 / 2 Cu 2+ , or 1 / 2 Zn 2+ More preferably, showing hydrogen atoms, A process for preparing an optical device according to embodiment 24, including the process described in embodiment 24. 27. At least one further functional material is selected from the group consisting of organic light-emitting materials, inorganic light-emitting materials, charge transport materials, host or matrix materials, optically transparent polymers, antioxidants or stabilizers, radical quenchers, photoinitiators or polymerization initiators, wetting and dispersing agents, scattering particles, refractive index modifiers, developer dissolution accelerators, scum removers, adhesion enhancers, polymerization inhibitors, defoamers, surfactants and sensitizers, and preferably selected from host or matrix materials, more preferably selected from (meth)methacrylate monomers or polymers, and / or The process according to embodiment 26, wherein at least one arbitrary solvent is selected from the group consisting of esters such as PGMEA (propylene glycol methyl ether acetate), ethyl acetate, butyl acetate, amyl acetate, ethylene carbonate, and methoxypropyl acetate; ketones such as methyl ethyl ketone (MEK), methyl isobutyl ketone, and cyclohexanone; glycols such as ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, triethylene glycol, glycol ethers, and hexylene glycol; ethers such as diethyl ether and tetrahydrofuran; alcohols such as methanol, ethanol, isopropanol, and butanol; or aromatic halogens and aliphatic hydrocarbons such as toluene, xylene, chloroform, dichloromethane, and heptane.

[0166] Effects of the present invention The present invention provides one or more of the following technical effects: Novel semiconducting luminescent nanoparticles that, when used in electronic devices, optical devices, or biomedical devices, can exhibit particularly high quantum yield and high luminescence efficiency. Novel semiconducting luminescent nanoparticles with improved thermal stability, Novel semiconducting luminescent nanoparticles with improved long-term stability, Preferably, novel semiconducting luminescent nanoparticles having good solubility in polar solvents,

[0167] Novel semiconducting luminescent nanoparticles having high chemical affinity to various polymer bases used in the manufacture of electronic, optical, or biomedical devices, particularly (meth)acrylate-based or epoxy-based nanoparticles. Novel semiconducting luminescent nanoparticles that can maintain stable dispersion in solutions, formulations, or films (including after film curing), Novel compounds that can further enhance the increased stability of the nanoparticle surface and the stability of the underlying nanoparticles that can be polymerized and / or crosslinked. Novel compounds that can passivate the surface of nanoparticles and provide chemical affinity between nanoparticles and various solvents and polymer bases used in the manufacture of electronic, optical, and biomedical devices, particularly polar solvents or (meth)acrylate bases, epoxy bases,

[0168] Novel compounds that can prevent aggregation of nanoparticles and ensure good dispersion of nanoparticles in solutions, formulations, and films (including after film curing), Optical devices having high luminous efficiency, high brightness, high contrast, high reliability, and short response time, and A simple preparation process for fabricating optical devices. The present invention will be described in more detail with reference to the following examples, but these are merely illustrative and do not limit the scope of the present invention. [Examples]

[0169] Examples: Compounds used in the example

[0170] Table 1: Compounds related to chemical formula (I) used in the examples [Table 1]

[0171] Example 1 - Preparation of 4-[(2-sulfanylacetyl)oxy]butylpropa-2-enoate (1) In the absence of light, 180 mL of ultra-dry toluene, benzene-1,4-diol (0.038 g, 0.01 eq.), 4-hydroxybutylprop-2-enoate (5.3 g, 1 eq.), and 2-sulfanylacetic acid (2.3 g, 0.67 eq.) were added with stirring to a 250 mL round-bottom flask connected to a Dean-Stark apparatus under an argon atmosphere. 4-methylbenzene-1-sulfonic acid (0.25 g, 0.04 eq.) was added to this mixture. The resulting mixture was boiled under reflux and an argon atmosphere with stirring for 18 hours. Heating was then stopped, and the system was cooled to room temperature (without external cooling). In the next step, the mixture was washed with distilled water, phase separated, dried over MgSO4, and filtered using a Buchner funnel apparatus, after which benzene-1,4-diol (0.010 g) was added. Next, the solvent is removed using a rotary evaporator at 5 mbar and 30°C. 7.1 g of pure 4-[(2-sulfanylacetyl)oxy]butylprop-2-enoate is obtained (yield: 87.9%).

[0172] Example 2 - Preparation of 2,5,8,11,14,17-hexamethyl-20-[(2-sulfanylacetyl)oxy]-3,6,9,12,15,18-hexaoxahenicosan-1-ylpropa-2-enoate(2) In the absence of light, 180 mL of ultra-dried toluene, benzene-1,4-diol (0.050 g, 0.03 eq.), 20-hydroxy-2,5,8,11,14,17-hexamethyl-3,6,9,12,15,18-hexaoxahenicosan-1-ylprop-2-enoate (7.65 g, 1 eq.), and 2-sulfanylacetic acid (0.98 g, 0.67 eq.) were added with stirring to a 250 mL round-bottom flask connected to a Dean-Stark apparatus under an argon atmosphere. Then, 4-methylbenzene-1-sulfonic acid (0.2 g, 0.07 eq.) was added. The resulting mixture was boiled under reflux under an argon atmosphere with stirring for 18 hours. Then, heating was stopped and the system was allowed to cool to room temperature (without external cooling). In the next step, the mixture is washed with distilled water, phase separation is performed, drying is carried out over MgSO4, and filtration is carried out using a Buchner funnel apparatus, after which benzene-1,4-diol (0.010 g) is added. The solvent is removed using a rotary evaporator at 5 mbar and 30°C. 8 g of pure 2,5,8,11,14,17-hexamethyl-20-[(2-sulfanylacetyl)oxy]-3,6,9,12,15,18-hexaoxahenicosan-1-ylprop-2-enoate (yield: 90.5%) is obtained as the product.

[0173] Example 3 - Functionalization of a quantum material having compound (1) and compound (2) as ligands Mix 30 mg of compound (1) or (2) into 298 μL (containing 30 mg of inorganic material) of quantum dot (QD) solution (red luminescent QD prepared as described in WO2014 / 162208 and / or US9, 343, 301BB, hereinafter referred to as "Red QD@Native") and stir at room temperature under an inert atmosphere for 16 hours. The sample containing compound (1) will form some precipitate, which will be removed by centrifugation (5500 rpm, 5 minutes), and the supernatant will be collected. The sample containing compound (2) will not form any precipitate. The resulting QDs, functionalized with either compound (1) or (2) as a ligand, will be denoted as Red QD@Ligand #1 and #2, respectively (in both cases, TGA indicates 60 wt.% ligand based on the total weight of the QD). The amount of organic ligand (compound (1) or (2)) is calculated using thermogravimetric analysis (TGA) (model TGA2, Metler Toledo). The quantum material is dissolved in toluene. The quantum yield is measured using a Hamamatsu absolute quantum yield analyzer (model: Quantaurus C11347). The quantum yield measurement results are summarized in Table 2 below.

[0174] Example 4 - Stability measurement of QDs ("Red QD@Native", "Red QD@Ligand #1", and "Red QD@Ligand #2") in a hydrophobic ink formulation (Formulation 1) Preparation of ink formulation: TBCH (4-tert butylsucrose hexyl acrylate), LA (lauryl acrylate), and trimethylolpropane triacrylate (TMPTA) are mixed in a weight ratio of 67.5:27.5:5 to prepare a hydrophobic ink formulation (referred to as "Formulation 1" herein). Then, 1 wt.% of the photopolymerization initiator Irgacure 819 is dissolved to form the ink formulation. Each QD obtained from Example 5 (i.e., "Red QD@Native", "Red QD@Ligand #1", and "Red QD@Ligand #2") was used in the following synthesis (including film preparation and thermal stability testing). The QD obtained from Example 3 is dried under vacuum. The dried QD is mixed with ink formulation 1 at a concentration of 30 wt.% (organic and inorganic weight) (this mixture is referred to as "QD@TBCH-1"). Film preparation: A glass substrate (4 × 4 cm) is coated with QD@TBCH-1 to form a film approximately 10 μm thick. The monomer is polymerized by irradiation with UV light (wavelength 365 nm) for 10 minutes under inert conditions (argon). The quantum yield after film curing is measured (on the same day) using a Hamamatsu absolute quantum yield analyzer (model: Quantaurus C11347). The quantum yield measurement results are summarized in Table 3 below. Thermal stability test: The film obtained after UV curing is placed in a tube oven under an argon atmosphere and heated to 180°C for 0.5 hours. The quantum yield of the heated film is measured one day after heating, and in certain cases, one week after heating. The results of the quantum yield measurement are summarized in Table 3 below.

[0175] Example 5: Stability measurement of QDs ("Red QD@Native", "Red QD@Ligand #1", and "Red QD@Ligand #2") in a hydrophobic ink formulation (Formulation 2) Preparation of ink formulations: A hydrophobic ink formulation (referred to herein as "Formulation 2") is prepared by dissolving 1 wt.% of Irgacure 819 in isobornyl acrylate (IBOA). The QDs obtained in Example 3 ("Red QD@Native", "Red QD@Ligand #1", "Red QD@Ligand #2") are dried under vacuum. Each dried QD is mixed with Ink Formulation 2 at a concentration of 30 wt% (organic and inorganic weight). Film preparation: Same as in Example 4. The quantum yield measurement results are summarized in Table 3 below. Thermal stability test: Same as Example 4. The quantum yield measurement results are summarized in Table 3 below.

[0176] Example 6 - Functionalization of a quantum material having compound (2) as a ligand 30 mg (or 15 mg) of compound (2) was mixed with 500 μL (containing 30 mg of inorganic) of QD solution (green luminescent QD prepared as described in WO 2014 / 162208 and / or US 9,343,301 BB, referred to as "Green QD@Native") and stirred at room temperature under an inert atmosphere for 16 hours, after which a solution of compound (2) was added. No precipitate was formed. In some cases, excess compound (2) was not washed away. The QD thus functionalized with compound (2) as a ligand is referred to as "Green QD@Ligand #2 Unwashed" (TGA indicates 5 wt.% ligand based on the total weight of OD). In the other case, 1 mL of anhydrous ethanol was added and the QD was separated by centrifugation (5500 rpm, 5 min). The supernatant was removed and the resulting solid was dried under vacuum. The QDs functionalized with the compound (2) obtained in this way are referred to as "Washed Green QD @ Ligand #2" (in TGA, 30 wt% ligand is indicated based on the total weight of the QD). The amount of organic ligand (compound (2)) is calculated using thermogravimetric analysis (TGA) (model TGA2, Metler Toledo). The quantum material is dissolved in 1 mL of toluene. The quantum yield is measured using a Hamamatsu absolute quantum yield analyzer (model: Quantaurus C11347). The quantum yield measurement results are summarized in Table 2 below.

[0177] Example 7 - Stability measurement of QDs ("Green QD@Native", "Green QD@Ligand #2 Unwashed", "Green QD@Ligand #2 Washed") in Ink Formulation 1 Using each QD obtained in Example 6 (i.e., "Green QD@Native", "Green QD@Ligand #4 Unwashed", and "Green QD@Ligand #2 Washed"), the following synthesis (including film preparation and thermal stability testing) was performed. The QD obtained in Example 6 is dried under vacuum. The dried QD is mixed with ink formulation 1 at a concentration of 30 wt.% (organic and inorganic weight) (this mixture is referred to as "QD@TBCH-2"). Film preparation: A glass substrate (4 × 4 cm) is coated with QD@TBCH-2 to form a film approximately 10 μm thick. The monomer is polymerized by irradiation with UV light (wavelength 365 nm) for 10 minutes under inert conditions (argon). The quantum yield after film curing is measured (on the same day) using a Hamamatsu absolute quantum yield analyzer (model: Quantaurus C11347). The quantum yield measurement results are summarized in Table 3 below. Thermal stability test: The film obtained after UV curing is placed in a tube oven under an argon atmosphere and heated to 180°C for 0.5 hours. The quantum yield of the heated film is measured one day after heating, and in certain cases, one week after heating. The results of the quantum yield measurement are summarized in Table 3 below.

[0178] Example 8 - Stability measurement of QD ("Green QD@Native") in ink formulation 1 containing compound (2) as an additive. The QDs from Example 6 (green QD@native) are dried and dissolved in ink formulation 1 at a concentration of 30 wt% (organic and inorganic weight). 30 μL of compound (2) is added directly to the ink (this mixture is referred to as "QD@TBCH-3"). Film preparation: A glass substrate (4 × 4 cm) was coated with 25 μL of QD@TBCH-3 using a hand bar coater to form a film approximately 10 μm thick. The monomer was polymerized by irradiating with ultraviolet light (wavelength 365 nm) for 10 minutes under inert conditions (argon). The quantum yield after film curing was measured (on the same day) using a Hamamatsu absolute quantum yield analyzer (model: Quantaurus C11347). The quantum yield measurement results are summarized in Table 3 below. Thermal stability test: The film obtained after UV curing is placed in a tube oven under an argon atmosphere and heated to 180°C for 0.5 hours. The quantum yield of the heated film is measured one day after heating. The results of the quantum yield measurement are summarized in Table 3 below.

[0179] Example 9 - Stability measurement of QD ("Green QD@Native") in ink formulation 2 The QDs from Example 6 ("Green QD@Native") are dried and dissolved in ink formulation 2 at a concentration of 30 wt% (organic and inorganic weight). Film preparation and thermal stability testing were carried out as described in Example 8. The quantum yield measurement results are summarized in Table 3 below.

[0180] Example 10 - Stability measurement of QD ("Green QD@Native") in ink formulation 2 containing compound (2) as an additive. The QDs from Example 6 ("Green QD@Native") are dried and dissolved in ink formulation 2 at a concentration of 30 wt.% (organic and inorganic weight). 30 μL of compound (2) is added directly to the ink formulation. Film preparation and thermal stability testing were carried out as described in Example 8. The quantum yield measurement results are summarized in Table 3 below.

[0181] Example 11 - Preparation of a monomer mixed ink containing 33.1 wt% green Cd-free QM and 26.5 wt% compound (2) as an additive. 0.39 g of 4-tert-butylcyclohexyl acrylate (TBCH, BASF), 0.95 g of lauryl acrylate (LA, Sigma Aldrich), and trimethylolpropane triacrylate (TMPTA, Sigma Aldrich) are mixed, stirred, and sonicated to obtain a mixture to which 0.01 g of dispersant (MD-1000, Otsuka Chemical) is dispersed. Next, 0.15 g of scattering beads (CR-67, Ishihara Sangyo) are mixed into the resulting mixture by sonication and grinding with zirconium beads. 13.9 ml of a green Cd-free QM toluene solution containing 1.32 g of solid QM (green luminescent QD prepared by the method described in WO 2014 / 162208 and / or US 9,343,301 BB, indicated as "Green QD@Native") is mixed into the resulting mixture by sonication, and the toluene is evaporated under low pressure at 40°C. Finally, 1.06 g of compound (2) prepared according to Example 2, 0.03 g of photoinitiator (Omnirad 819, IGM RESINS BV), and 0.02 g of stabilizer (Irganox 1010, BASF) are mixed with a mixture obtained by stirring and sonication.

[0182] Comparative Example 1 - Preparation of a monomer-mixed ink containing 33.1 wt% green Cd-free QM 0.68 g of 4-tert-butylcyclohexyl acrylate (TBCH, BASF), 1.67 g of lauryl acrylate (LA, Sigma Aldrich), and 0.12 g of trimethylolpropane triacrylate (TMPTA, Sigma Aldrich) are mixed, stirred, and sonicated to obtain a mixture to which 0.01 g of a dispersant (MD-1000, Otsuka Chemical) is dispersed. Then, 0.15 g of scattering beads (CR-67, Ishihara Sangyo) are mixed into the resulting mixture by sonication and grinding with zirconium beads. To the resulting mixture, 13.9 ml of a green Cd-free QM toluene solution containing 1.32 g of solid QM (a green luminescent QD prepared as described in WO 2014 / 162208 and / or US 9,343,301 BB, referred to as "Green QD@Native") is mixed by sonication, and the toluene is evaporated under low pressure at 40°C. Finally, 0.03 g of photoinitiator (Omnirad 819, IGM RESINS BV) and 0.02 g of stabilizer (Irganox 1010, BASF) are mixed with the resulting mixture by stirring and sonication.

[0183] Example 12 - Preparation of a monomer mixed ink containing 38.1 wt% green Cd-free QM and 15.3 wt% compound (2) as an additive. 0.45 g of 4-tert-butylcyclohexyl acrylate (TBCH, BASF), 1.10 g of lauryl acrylate (LA, Sigma Aldrich), and 0.08 g of trimethylolpropane triacrylate (TMPTA, Sigma Aldrich) are mixed, stirred, and sonicated to obtain a mixture to which 0.01 g of dispersant (MD-1000, Otsuka Chemical) is dispersed. Then, 0.17 g of scattering beads (CR-67, Ishihara Sangyo) are mixed into the resulting mixture by sonication and grinding with zirconium beads. To the resulting mixture, 16.0 ml of a green Cd-free QM toluene solution containing 1.53 g of solid QM (green luminescent QD prepared as described in WO2014 / 162208 and / or US9, 343, 301 BB, indicated as "Green QD@Native") was mixed by sonication, and the toluene was evaporated at 40°C under low pressure to obtain the mixture. Finally, 0.61 g of compound (2) prepared according to Example 2, 0.03 g of photoinitiator (Omnirad 819, IGM RESINS BV), and 0.03 g of stabilizer (Irganox 1010, BASF) were mixed with the mixture obtained by stirring and sonication.

[0184] Comparative Example 2 - Preparation of a monomer-mixed ink containing 38.1 wt% green Cd-free QM 0.61 g of 4-tert-butylcyclohexyl acrylate (TBCH, BASF), 1.51 g of lauryl acrylate (LA, Sigma Aldrich), and 0.11 g of trimethylolpropane acrylate (TMPTA, Sigma Aldrich) are mixed and sonicated, and 0.01 g of dispersant (MD-1000, Otsuka Chemical) is dispersed in the resulting mixture. Next, 0.17 g of scattering beads (CR-67, Ishihara Sangyo) are mixed into the resulting mixture by sonication and pulverization with zirconium beads. 16.0 ml of a green Cd-free QM toluene solution containing 1.53 g of solid QM (green luminescent QD prepared as described in WO 2014 / 162208 and / or US 9,343,301 BB, indicated as "Green QD@Native") is mixed into the resulting mixture by sonication, and the toluene is evaporated at 40°C under low pressure. Finally, 0.03 g of photoinitiator (Omnirad 819, IGM RESINS BV) and 0.03 g of stabilizer (Irganox 1010, BASF) are mixed with the mixture obtained by stirring and sonication. The compositions of the monomer mixed inks prepared according to Examples 11 and 12 and Comparative Examples 1 and 2 are shown in Table 4 below.

[0185] Example 13 - Optical Measurement Film preparation: Each monomer mixed ink obtained in Examples 11 and 12 and Comparative Examples 1 and 2 was capillarily injected into a cell containing a glass substrate sandwiched between sealing materials to form films with a thickness of approximately 15 μm. Under inert conditions (N2), the monomers were polymerized by irradiation with UV light (365 nm (i-ray) at 3.9 mW / cm2) for 200 seconds.

[0186] optical measurement The external quantum efficiency of the fabricated film was measured using an external quantum efficiency measuring device that includes a halogen lamp (LUMOLUX fuse optik), a bandpass filter (CWL: 450 nm / FWHM: 10 nm), an integrating sphere (ISP-50-8-R, Ocean Optics), and a spectrometer (USB-4000, Ocean Optics). The emission spectrum of the fabricated film was measured by irradiating the glass surface side of the film with 450 nm blue excitation light through an optical fiber. The diameter of the irradiation area was approximately 5 mm. The size of the film substrate was larger than the port of the integrating sphere. Green emission light from the QD film and unabsorbed blue excitation light entered the integrating sphere. The integrating light was sent to the spectrometer via an optical fiber. The results of optical measurements of quantum material-containing films prepared using monomer-mixed inks obtained in Examples 11 and 12 and Comparative Examples 1 and 2 are shown in Figures 1 and 2.

[0187] Experimental results: Table 2: Quantum yield and ligand amount of functionalized QDs with acrylic acid-thiol ligands. [Table 2] Based on the total weight of the QD

[0188] Table 3: Quantum yield measurement results of QD (red and green) films after UV curing and heating. [Table 3] (*QY is measured 5-15 minutes after curing, ** is based on the total weight of the ink composition), calculated using TGA; Model TGA2, Metler Toledo)

[0189] As can be seen from the results presented in Tables 2 and 3, in all experiments, the quantum yield of red or green QDs did not decrease significantly after UV curing of the film (in specific cases, QY remained higher after curing). On the other hand, as can be seen from the results presented in Table 3, when the cured film was heated (1 day after heating), a decrease in quantum yield was observed. However, while the decrease in quantum yield was very large for QDs with native ligands, the decrease in quantum yield was significantly suppressed for QDs according to the present invention (i.e., QY stability increased). This shows that the thermal stability of QDs according to the present invention is significantly increased after ligand exchange with a bifunctional acrylate-based compound as defined herein (here, after thiol-acrylate compound (1) or (2)). Specifically, as can be seen from Examples 4 and 5 in Table 3, the bifunctional acrylate-based ligand according to the present invention can contribute to the high stability of red QDs in the IBOA-containing ink formulation (Formulation 2), as well as in the TBCH / LA / TMPTA-containing ink formulation (Formulation 1). Furthermore, as can be seen from Example 7, the bifunctional acrylate-based ligand according to the present invention can contribute to the high stability of green QDs in the TBCH / LA / TMPTA formulation (Formulation 1) even one week after heating ("Green QD @ Ligand #2 without washing"). Comparison of the experimental results of Examples 7 and 8 and 9 and 10 also reveals that higher stability is obtained when the bifunctional acrylate-based compound represented by chemical formula (I) as defined herein (here, thiol-acrylate compound (2)) is used according to the present invention as an additive added directly to the QD-containing ink formulation.

[0190] Table 4: Composition of monomer mixed inks prepared in Examples 11 and 12 and Comparative Examples 1 and 2. [Table 4]

[0191] Figure 1 is a chart showing the change in external quantum efficiency (EQE) / % of the QD-containing film obtained from Example 13 using the inks prepared in Examples 11 and 12 and Comparative Examples 1 and 2. Figure 2 shows the wavelength-normalized emission spectra of the QD-containing films obtained from Example 13 using the inks prepared in Examples 11 and 12 and Comparative Examples 1 and 2, illustrating the shift in maximum intensity. As can be seen from the measurement results presented in Figures 1 and 2, when a bifunctional polymerizable acrylate-based compound represented by chemical formula (I) as defined herein (here, thiol-acrylate compound (2)) is used in accordance with the present invention as an additive directly added to a QD-containing ink formulation (Examples 11 and 12), a 1-2% increase in EQE and a 1-2 nm reduction in red shift at wavelength are achieved compared to ink formulations that do not contain such a compound (Comparative Examples 1 and 2).

[0192] Example 14 - Preparation of monomer mixture ink Monomer mixed inks were prepared in the same manner as described in the section for Example 11, except that compound 2 was used in amounts of 1.5, 3, 7.5, 15, 25, and 25 wt.% as an additive. A monomer mixed ink (0 wt.%) without compound 2 was also prepared as a comparative example. EQE measurement is performed in the same manner as described in Example 13. Table 5 shows the results of the EQE measurement.

[0193] Table 5 [Table 5]

Claims

1. A core, one or more shell layers, and the following chemical formula (1) or (2) 【Chemistry 1】 【Chemistry 2】 Semiconducting luminescent nanoparticles containing a compound represented by [formula].

2. The following chemical formula (1) or (2) 【Transformation 3】 【Chemistry 4】 A compound represented by [this symbol].

3. The nanoparticles according to claim 1, and A composition comprising at least one further functional material.

4. The composition according to claim 3, wherein the at least one further functional material is a host or matrix material.

5. The nanoparticles according to claim 1, or the composition according to claim 3 or 4, A formulation containing at least one solvent.

6. Use of the nanoparticles described in claim 1, the composition described in claim 3 or 4, or the formulation described in claim 5 in an electronic device, an optical device, or a biomedical device.

7. An optical medium comprising the nanoparticles described in claim 1, the compound described in claim 2, the composition described in claim 3 or 4, or the formulation described in claim 5.

8. An optical device comprising nanoparticles according to claim 1, or a compound according to claim 2, or a composition according to claim 3 or 4, or a formulation according to claim 5, or an optical medium according to claim 7.

9. Steps a) to c): a) Semiconducting luminescent nanoparticles having a core and at least one shell layer, at least one further functional material, chemical formula (1) or (2) as defined below 【Transformation 5】 【Transformation 6】 To prepare a mixture by mixing the compound represented by and optionally at least one solvent; b) Providing a mixture onto a substrate; and c) The resulting mixture is subjected to light irradiation having a peak light wavelength in the range of 300 to 650 nm: A process for preparing an optical device according to claim 8, including the process described in claim 8.

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