Quantum dot, electroluminescent device, and ink composition

Abstract

To provide a quantum dot having excellent stability and giving high emission efficiency when used as a luminescent material of an electroluminescent element, and to provide an electroluminescent element and an ink composition containing the quantum dot.SOLUTION: The quantum dot contains a semiconductor particle surface-treated with a surface treatment agent, wherein the surface treatment agent contains a compound represented by general formula (1) or the like.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to quantum dots, an electroluminescent device using the same, and an ink composition. [Background technology]

[0002] Electroluminescence (EL) devices are attracting attention as surface-emitting devices that are lightweight, thin, consume little power, and offer excellent shape flexibility. These devices have many excellent features, such as high-brightness emission, fast response, a wide viewing angle, thinness, lightness, and high resolution, and their application to flat panel displays and lighting is being considered. Quantum dots are attracting attention as one type of electroluminescent device.

[0003] Quantum dots are small nanoscale semiconductor particles that exhibit behavior intermediate between that of atoms or molecules and that of macroscopic solids (bulk structures). Nanoscale materials (semiconductor particles) in which charge carriers and excitons are confined in all three dimensions are called quantum dots. As quantum dot size decreases, their effective band gap increases. As quantum dot size decreases, their absorption and emission shift toward shorter wavelengths, i.e., from red to blue. Furthermore, by controlling the composition and size of quantum dots in combination, a wide spectrum from the infrared to ultraviolet range can be obtained. Furthermore, by controlling the size distribution, a spectrum with a narrow half-width and excellent color purity can be obtained. Therefore, taking advantage of these properties, quantum dot-based organic electroluminescent devices using quantum dots composed of semiconductor nanocrystals as the light-emitting material have been proposed in recent years.

[0004] Quantum dots are generally surface-treated with ligands. Many of these ligands have a structure in which an adsorption group is attached to the end of a long-chain alkyl group. While these ligands have the effect of improving the chemical stability of the quantum dot surface, thereby increasing durability, and enhancing dispersibility and dispersion stability in organic solvents and water, they are insulating and do not exhibit sufficient performance when used in electroluminescent devices. For this reason, in recent years, ligands have been designed with the aim of improving the electrical properties of quantum dots, such as charge injection (Patent Documents 1 and 2). However, when used as a light-emitting material in electroluminescent devices, the luminescence efficiency and stability are insufficient, and there are also issues with film-forming properties when used in ink compositions. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2004-315661 [Patent Document 2] Japanese Patent Application Laid-Open No. 2008-214363 Summary of the Invention [Problem to be solved by the invention]

[0006] The problem to be solved by the present invention is to provide quantum dots with excellent stability that can provide high luminous efficiency when used as a light-emitting material in an electroluminescent device. Another object of the present invention is to provide an electroluminescent device with high luminous efficiency and little decrease in luminance even when driven for a long period of time. Another object of the present invention is to provide an ink composition with high stability, little decrease in fluorescence quantum yield when stored for a long period of time, and excellent film-forming properties. [Means for solving the problem]

[0007] The present inventors have conducted extensive research to solve the above problems, and have found that the problems of the present invention can be solved in the following aspects, thereby completing the present invention.

[0008] [1]: Quantum dots containing semiconductor particles that have been surface-treated with a surface treatment agent, wherein the surface treatment agent contains a compound represented by any one of the following general formulas (1) to (6): [ka] [In general formula (1), X 1 ~X 6 are each independently, CR 1 -R 2 , or N, X 1 ~X 6 At least one of them is N, X 1 ~X 6 Among them, CR 1 -R 2 The number of is greater than or equal to the number of N. R 1 are each independently a direct bond, —O—, —CO—, —COO—, or —SO 2 —. R 2 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group. However, R 2 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R 1 is a direct bond. X 1 ~X 6 At least one of these has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. However, X 1 ~X 6 If one of X has an unsubstituted amino group, 1 ~X6 The number of unsubstituted amino groups contained in X is 1, and 1 ~X 6 does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group.] [ka] [In general formula (2), X 7 ~X 14 are each independently, CR 1 -R 2 , or N, X 7 ~X 14 At least one of them is N, X 7 ~X 14 Among them, CR 1 -R 2 The number of is greater than or equal to the number of N. 1 are each independently a direct bond, —O—, —CO—, —COO—, or —SO 2 —. R 2 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group. However, R 2 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R 1 is a direct bond. X 7 ~X 14 At least one of these has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. However, X 7 ~X 14 If one of X has an unsubstituted amino group,7 ~X 14 The number of unsubstituted amino groups contained in X is 1, and 7 ~X 14 does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group. General formula (2) excludes cases where it is represented by general formula (1). [ka] [In general formula (3), X 15 ~X 18 are each independently, CR 1 -R 2 , or N, X 15 ~X 18 At least one of them is N, X 15 ~X 18 Among them, CR 1 -R 2 The number of is greater than or equal to the number of N. R 1 are each independently a direct bond, —O—, —CO—, —COO—, or —SO 2 —. R 2 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group. However, R 2 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R 1 is a direct bond. X 15 ~X 18 At least one of these has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. However, X 15 ~X 18 If one of X has an unsubstituted amino group, 15 ~X 18 The number of unsubstituted amino groups contained in X is 1, and 15 ~X 18 does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group. Z 1 is CR 3 R 4 , N.R. 5 , O, or S, and R 3 ~R 5 are each independently a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group. General formula (3) excludes cases where it is represented by any of general formulas (1) and (2). [ka] [In general formula (4), X 19 ~X 24 are each independently, CR 1 -R 2 , or N, X 19 ~X 24 At least one of them is N, X 19 ~X 24 Among them, CR 1 -R 2 The number of is greater than or equal to the number of N. R 1 are each independently a direct bond, —O—, —CO—, —COO—, or —SO 2 —. R 2are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group. However, R 2 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R 1 is a direct bond. X 19 ~X 24 At least one of these has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. However, X 19 ~X 24 If one of X has an unsubstituted amino group, 19 ~X 24 The number of unsubstituted amino groups contained in X is 1, and 19 ~X 24 does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group. Z 2 is CR 3 R 4 , N.R. 5 , O, or S, and R 3 ~R 5 are each independently a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group. General formula (4) excludes cases where it is represented by any of general formulas (1) to (3). [ka] [In general formula (5), X 25 ~X 30 are each independently, CR1 -R 2 , or N, X 25 ~X 30 At least one of them is N, X 25 ~X 30 Among them, CR 1 -R 2 The number of is greater than or equal to the number of N. R 1 are each independently a direct bond, —O—, —CO—, —COO—, or —SO 2 —. R 2 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group. However, R 2 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R 1 is a direct bond. X 25 ~X 30 At least one of these has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. However, X 25 ~X 30 If one of X has an unsubstituted amino group, 25 ~X 30 The number of unsubstituted amino groups contained in X is 1, and 25 ~X 30 does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group. Z 3 is CR 3 R 4 , N.R. 5 , O, or S, and R 3 ~R5 are each independently a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group. General formula (5) excludes cases where it is represented by any of general formulas (1) to (4). [ka] [In general formula (6), X 31 ~X 37 are each independently, CR 1 -R 2 , or N, X 31 ~X 37 At least one of them is N, X 31 ~X 37 Among them, CR 1 -R 2 The number of is greater than or equal to the number of N. R 1 are each independently a direct bond, —O—, —CO—, —COO—, or —SO 2 —. R 2 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group. However, R 2 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R 1 is a direct bond. X 31 ~X 37 At least one of these has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. However, X 31~X 37 If one of X has an unsubstituted amino group, 31 ~X 37 The number of unsubstituted amino groups contained in X is 1, and 31 ~X 37 does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group. General formula (6) excludes cases where it is represented by any of general formulas (1) to (5).

[0009] [2]: The quantum dot according to [1], wherein the surface treatment agent contains a compound represented by any one of the following general formulas (7) to (9): [ka] [In general formula (7), R 5 ~R 7 are each independently -R 22 -R 23 and R 22 are each independently a direct bond, —O—, —CO—, or —COO—; R 23 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), or a substituted amino group. However, R 23 is a hydrogen atom, a halogen atom, a cyano group, or a substituted amino group, R 22 is a direct bond.] [ka] [In general formula (8), R 8 ~R 14 are each independently -R 22 -R 23 and R 22are each independently a direct bond, —O—, —CO—, or —COO—; R 23 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), or a substituted amino group. However, R 23 is a hydrogen atom, a halogen atom, a cyano group, or a substituted amino group, R 22 is a direct bond.] [ka] [In general formula (9), R 15 ~R 21 , , are each independently, -R 22 -R 23 and R 22 are each independently a direct bond, —O—, —CO—, or —COO—; R 23 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), or a substituted amino group. However, R 23 is a hydrogen atom, a halogen atom, a cyano group, or a substituted amino group, R 22 is a direct bond.]

[0010] [3]: An ink composition comprising the quantum dots according to [1] or [2] and a dispersion medium.

[0011] [4]: An electroluminescent device having an anode, a light-emitting layer, and a cathode on a substrate, wherein the light-emitting layer contains the quantum dots according to [1] or [2]. [Effects of the Invention]

[0012] The present invention has the excellent effect of providing quantum dots with excellent stability that can achieve high luminous efficiency when used as a light-emitting material in an electroluminescent element. It also has the excellent effect of providing an electroluminescent element with high luminous efficiency and little decrease in luminance during long-term operation. Furthermore, it has the excellent effect of providing an ink composition with high stability, little decrease in fluorescence quantum yield during long-term storage, and excellent film-forming properties. DETAILED DESCRIPTION OF THE INVENTION

[0013] <Quantum dots> The quantum dots of the present invention are characterized by containing semiconductor particles that have been surface-treated with a surface treatment agent containing a compound represented by any one of the above general formulas (1) to (6). The present invention will be described in detail below.

[0014] <Semiconductor particles> The materials of the semiconductor particles include carbon (C) (amorphous carbon, graphite, graphene, carbon nanotubes, etc.), silicon (Si), germanium (Ge), tin (Sn), and other elements of group IV of the periodic table, phosphorus (P) (black phosphorus), and other elements of group V of the periodic table, selenium (Se), tellurium (Te), and other elements of group VI of the periodic table, tin oxide (IV), boron nitride (BN), boron phosphide (BP), boron arsenide (BAs), aluminum nitride (AlN), aluminum phosphide (AlP), aluminum arsenide (AlAs), and aluminum antimonide (AlSb). ), gallium nitride (GaN), gallium phosphide (GaP), gallium arsenide (GaAs), gallium antimonide (GaSb), indium nitride (InN), indium phosphide (InP), indium arsenide (InAs), indium antimonide (InSb), and other compounds of group III elements and group V elements of the periodic table. Aluminum sulfide (Al2S3), aluminum selenide (Al2Se3), gallium sulfide (Ga2S3), gallium selenide (GaSe, Ga2Se3), gallium telluride (GaTe, Ga2Te3), indium oxide (In2O 3)Compounds of Group III elements of the periodic table and Group VI elements of the periodic table, such as indium sulfide (In2S3, InS), indium selenide (In2Se3), and indium telluride (In2Te3), zinc oxide (ZnO), zinc sulfide (ZnS), zinc selenide (ZnSe), zinc telluride (ZnTe), cadmium oxide (CdO), cadmium sulfide (CdS), cadmium selenide (CdSe), cadmium telluride (CdTe), mercury sulfide (HgS), mercury selenide (HgSe), and mercury telluride (HgTe). Examples of suitable semiconductors include compounds of Group II elements and Group VI elements, such as copper(I) oxide (CuO), compounds of Group I elements and Group VI elements, such as copper(I) chloride (CuCl), copper(I) bromide (CuBr), copper(I) iodide (CuI), silver chloride (AgCl), and silver bromide (AgBr), and chalcopalite-type compound semiconductors of Group I-III-VI2 elements, such as AgInS and CuInS. Two or more of these may be used in combination, if necessary. These semiconductors may contain elements other than the constituent elements. For example, in the III-V group, alloys such as InGaP and InGaN may be used. Semiconductor particles doped with rare earth elements or transition metal elements may also be used. Examples include ZnS:Mn, ZnS:Tb, ZnS:Ce, and LaPO:Ce.

[0015] Among these, alloys such as silicon (Si), germanium (Ge), gallium nitride (GaN), gallium phosphide (GaP), gallium arsenide (GaAs), indium nitride (InN), indium phosphide (InP), indium arsenide (InAs), gallium selenide (GaSe, Ga2Se3), indium sulfide (In2S3, InS), zinc oxide (ZnO), zinc sulfide (ZnS), zinc selenide (ZnSe), zinc telluride (ZnTe), cadmium oxide (CdO), cadmium sulfide (CdS), cadmium selenide (CdSe), cadmium telluride (CdTe), InGaP, and InGaN are preferably used, and indium phosphide (InP), cadmium selenide (CdSe), zinc sulfide (ZnS), and zinc selenide (ZnSe) are particularly preferably used. In particular, it is preferable to use InP for the core and ZnS and / or ZnSe for the shell.

[0016] Furthermore, perovskite crystals can also be suitably used as the material for the semiconductor particles. Perovskite crystals have a composition represented by the following formula (I) and have a three-dimensional crystal structure. Formula (I): AQX3 [In formula (I), A is a monovalent cation of at least one amine compound selected from the group consisting of methylammonium (CH3NH2) and formamidinium (NH2CHNH), or a monovalent cation of at least one alkali metal element selected from the group consisting of rubidium (Rb), cesium (Ce), and francium (Fr); Q is a divalent cation of at least one metal element selected from the group consisting of lead (Pb) and tin (Sn); and X is a monovalent anion of at least one halogen element selected from the group consisting of iodine (I), bromine (Br), and chlorine (Cl)]

[0017] The semiconductor particles preferably have a core-shell structure. Core-shell semiconductor particles have a core structure coated with a material composed of a different component from the core material. By selecting a semiconductor with a large band gap for the shell, excitons (electron-hole pairs) generated by photoexcitation are confined within the core. As a result, the probability of nonradiative transitions at the particle surface is reduced, improving the quantum yield of light emission and the stability of fluorescence properties. The shell may also have multiple layers. Furthermore, the boundaries between the core and shell, and between one shell and another, may be clear or may have a gradient structure in which the layers are gradually joined together by providing a concentration gradient. Furthermore, the shell may cover only a portion of the core or the entire core.

[0018] The average particle size of the semiconductor particles, including the core and shell, is usually 0.5 nm to 100 nm, preferably 1 to 50 nm, and more preferably 1 to 15 nm.

[0019] The average particle size referred to here refers to the average value obtained by observing semiconductor particles with a transmission electron microscope (TEM) and measuring the sizes of 30 randomly selected particles. Since the semiconductor particles in quantum dots are accompanied by a surface treatment agent (described below), a scanning transmission electron microscope equipped with energy dispersive X-ray analysis is used to identify the semiconductor particles. The particle size of the semiconductor particles is measured by utilizing the fact that, due to differences in electron density, the semiconductor particle portion appears dark relative to the surface treatment agent in the transmission electron microscope image. Furthermore, the shape of the semiconductor particles is not limited to spherical, but may also be rod-shaped, disk-shaped, or other shapes.

[0020] <Surface treatment agent> The surface treatment agent (hereinafter sometimes abbreviated as "treatment agent") used in the present invention contains a compound represented by any one of the above general formulas (1) to (6).

[0021] The above general formula (1) will be explained.

[0022] In general formula (1), X 1 ~X 6are each independently, CR 1 -R 2 , or N and X 1 ~X 6 At least one of them is N and X 1 ~X 6 Among them, CR 1 -R 2 The number of X is equal to or greater than the number of N. In one embodiment, from the viewpoint of availability of synthetic raw materials, 1 ~X 6 In another embodiment, from the viewpoint of durability of the electroluminescent device, X 1 ~X 6 Among these, it is preferable that N is two or more.

[0023] R 1 are each independently a direct bond, -O-, -CO-, -COO-, or -SO2-. 2 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, provided that R 2 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R 1 is a direct bond. The phrase "excluding the case where the compound is a residue of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine" also includes cases where the compound has a substituent, and the substituent has the same meaning as the substituent of the present invention (the same applies to general formulas (2) to (6) described later).

[0024] where R 2 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0025] R 2 The monovalent aliphatic hydrocarbon group is preferably a monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, and examples of such groups include alkyl groups, alkenyl groups, alkynyl groups, and cycloalkyl groups. The monovalent aliphatic hydrocarbon group may be linear or branched.

[0026] Here, examples of the alkyl group include alkyl groups having 1 to 18 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, decyl, dodecyl, pentadecyl, and octadecyl groups.

[0027] Examples of the alkenyl group include alkenyl groups having 2 to 18 carbon atoms, such as vinyl, 1-propenyl, 2-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-octenyl, 1-decenyl, and 1-octadecenyl.

[0028] Examples of the alkynyl group include alkynyl groups having 2 to 18 carbon atoms, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-octynyl, 1-decynyl, and 1-octadecynyl.

[0029] Examples of the cycloalkyl group include cycloalkyl groups having 3 to 18 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclooctadecyl, and 2-indeno groups.

[0030] Furthermore, R 2 Examples of the monovalent aromatic hydrocarbon group include monovalent single ring, fused ring, and ring assembly aromatic hydrocarbon groups, and are preferably monovalent aromatic hydrocarbon groups having 6 to 18 carbon atoms.

[0031] Here, examples of the monovalent monocyclic aromatic hydrocarbon group include monovalent monocyclic aromatic hydrocarbon groups having 6 to 18 carbon atoms, such as a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2,4-xylyl group, a p-cumenyl group, and a mesityl group.

[0032] Furthermore, examples of the monovalent fused ring aromatic hydrocarbon group include monovalent fused ring aromatic hydrocarbon groups having 10 to 18 carbon atoms, such as a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 5-anthryl group, a 1-phenanthryl group, a 9-phenanthryl group, a 1-acenaphthyl group, a 2-azulenyl group, a 1-pyrenyl group, and a 2-triphenylyl group.

[0033] Examples of the monovalent ring assembly aromatic hydrocarbon group include monovalent ring assembly aromatic hydrocarbon groups having 12 to 18 carbon atoms, such as o-biphenylyl group, m-biphenylyl group, and p-biphenylyl group.

[0034] Furthermore, R 2 Examples of the monovalent aromatic heterocyclic group include a triazolyl group, a 3-oxadiazolyl group, a 2-furanyl group, a 3-furanyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3-thienyl group, a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-pyrazyl group, a 2-oxazolyl group, a 3-isoxazolyl group, a 2-thiazolyl group, a 3-isothiazolyl group, and a 2-imidazolyl group. and monovalent aromatic heterocyclic groups having 2 to 18 carbon atoms such as a 3-pyrazolyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group, an 8-quinolyl group, a 1-isoquinolyl group, a 2-quinoxalinyl group, a 2-benzofuryl group, a 2-benzothienyl group, an N-indolyl group, an N-acridinyl group, a 2-thiophenyl group, a 3-thiophenyl group, a bipyridyl group, and a phenanthrolyl group.

[0035] R 2The monovalent aliphatic hydrocarbon group, the monovalent aromatic hydrocarbon group, and the monovalent aromatic heterocyclic group may further have a substituent, and in this case, examples of the substituent that may be had include a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group, a cyano group, a nitro group, or a carboxy group. R 2 The amino group may further have a substituent, and in this case, examples of the substituent include a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group. For details of these substituents, the above-mentioned explanations of the monovalent aliphatic hydrocarbon group, monovalent aromatic hydrocarbon group, and monovalent aromatic heterocyclic group of R2 can be cited.

[0036] X 1 ~X 6 At least one of X has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. 1 ~X 6 From the viewpoints of the stability of the ink composition and the luminous efficiency and durability of the electroluminescent device, it is preferable that the compound has at least one sulfonic acid group, phosphonic acid group, or unsubstituted amino group. In particular, from the viewpoint of improving the electron transport property, it is preferable that the compound has at least one sulfonic acid group or phosphonic acid group, and from the viewpoint of improving the hole transport property, it is preferable that the compound has at least one unsubstituted amino group. However, X 1 ~X 6 If one of X has an unsubstituted amino group, 1 ~X 6 The number of unsubstituted amino groups contained in X is 1, and 1 ~X 6 does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group.

[0037] Among the compounds represented by general formula (1), the compound represented by general formula (7) is preferred from the viewpoint of long-term dispersion stability.

[0038] The general formula (2) will be explained below: The general formula (2) does not include the case where it is represented by the general formula (1).

[0039] In general formula (2), X 7 ~X 14 are each independently, CR 1 -R 2 , or N and X 7 ~X 14 At least one of them is N and X 7 ~X 14 Among them, CR 1 -R 2 The number of is greater than or equal to the number of N.

[0040] R 1 are each independently a direct bond, -O-, -CO-, -COO-, or -SO2-. 2 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, provided that R 2 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R 1 is a direct bond.

[0041] R 2 The above explanation of general formula (1) can be applied to the substituted or unsubstituted monovalent aliphatic hydrocarbon group, substituted or unsubstituted monovalent aromatic hydrocarbon group, and substituted or unsubstituted monovalent aromatic heterocyclic group.

[0042] X7 ~X 14 At least one of X has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. 7 ~X 14 If one of X has an unsubstituted amino group, 7 ~X 14 The number of unsubstituted amino groups contained in X is 1, and 7 ~X 14 does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group.

[0043] X 7 ~X 14 The preferred embodiment of X in the general formula (1) is as follows: 1 ~X 6 The explanation about this can be used.

[0044] Among the compounds represented by general formula (2), the compounds represented by the above general formula (8) or (9) are preferred from the viewpoint of long-term dispersion stability.

[0045] The general formula (3) will be explained below: The general formula (3) does not include the cases where it is represented by any of the general formulas (1) and (2) above.

[0046] In general formula (3), X 15 ~X 18 are each independently, CR 1 -R 2 , or N and X 15 ~X 18 At least one of them is N and X 15 ~X 18 Among them, CR 1 -R 2 The number of X is equal to or greater than the number N. From the viewpoint of durability of the electroluminescent device, 15 ~X 18 Among these, it is preferable that N is two or more.

[0047] R 1 are each independently a direct bond, -O-, -CO-, -COO-, or -SO2-. 2are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, provided that R 2 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R 1 is a direct bond.

[0048] R 2 The above explanation of general formula (1) can be applied to the substituted or unsubstituted monovalent aliphatic hydrocarbon group, the substituted or unsubstituted monovalent aromatic hydrocarbon group, the substituted or unsubstituted monovalent aromatic heterocyclic group, and the substituted or unsubstituted amino group.

[0049] X 15 ~X 18 At least one of X has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. 15 ~X 18 If one of X has an unsubstituted amino group, 15 ~X 18 The number of unsubstituted amino groups contained in X is 1, and 15 ~X 18 does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group.

[0050] X 15 ~X 18 The preferred embodiment of X in the general formula (1) is as follows: 1 ~X 6 The explanation about this can be used.

[0051] Z 1 is CR 3 R 4, N.R. 5 , O, or S, and R 3 ~R 5 are each independently a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group.

[0052] Z 1 is preferably O or S from the viewpoint of durability of the electroluminescent device.

[0053] R 3 , R 4 , and R 5 As the substituted or unsubstituted monovalent aliphatic hydrocarbon group, the substituted or unsubstituted monovalent aromatic hydrocarbon group, or the substituted or unsubstituted monovalent aromatic heterocyclic group, R 2 The explanation about this can be used.

[0054] The general formula (4) will be explained below: The general formula (4) does not include the cases where it is represented by any of the general formulae (1) to (3) above.

[0055] In general formula (4), X 19 ~X 24 are each independently, CR 1 -R 2 , or N and X 19 ~X 24 At least one of them is N and X 19 ~X 24 Among them, CR 1 -R 2 The number of X is equal to or greater than the number N. From the viewpoint of durability of the electroluminescent device, 19 ~X 24 Among these, it is preferable that N is two or more.

[0056] R 1 are each independently a direct bond, -O-, -CO-, -COO-, or -SO2-. 2are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, provided that R 2 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R 1 is a direct bond.

[0057] R 2 The above explanation of general formula (1) can be applied to the substituted or unsubstituted monovalent aliphatic hydrocarbon group, the substituted or unsubstituted monovalent aromatic hydrocarbon group, the substituted or unsubstituted monovalent aromatic heterocyclic group, and the substituted or unsubstituted amino group.

[0058] X 19 ~X 24 At least one of X has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. 19 ~X 24 If one of X has an unsubstituted amino group, 19 ~X 24 The number of unsubstituted amino groups contained in X is 1, and 19 ~X 24 does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group.

[0059] X 19 ~X 24 The preferred embodiment of X in the general formula (1) is as follows: 19 ~X 24 The explanation about this can be used.

[0060] Z 2 is CR 3 R 4, N.R. 5 , O, or S, and R 3 ~R 5 are each independently a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group.

[0061] Z 2 is preferably O or S from the viewpoint of durability of the electroluminescent device.

[0062] R 3 , R 4 , and R 5 As the substituted or unsubstituted monovalent aliphatic hydrocarbon group, the substituted or unsubstituted monovalent aromatic hydrocarbon group, or the substituted or unsubstituted monovalent aromatic heterocyclic group, R 2 The explanation about this can be used.

[0063] The general formula (5) will be explained below: The general formula (5) does not include the cases where it is represented by any of the general formulae (1) to (4) above.

[0064] In general formula (5), X 25 ~X 30 are each independently, CR 1 -R 2 , or N and X 25 ~X 30 At least one of them is N and X 25 ~X 30 Among them, CR 1 -R 2 The number of X is equal to or greater than the number N. From the viewpoint of durability of the electroluminescent device, 25 ~X 30 Among these, it is preferable that N is two or more.

[0065] R 1 are each independently a direct bond, -O-, -CO-, -COO-, or -SO2-. 2are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, provided that R 2 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R 1 is a direct bond.

[0066] R 2 The above explanation of general formula (1) can be applied to the substituted or unsubstituted monovalent aliphatic hydrocarbon group, the substituted or unsubstituted monovalent aromatic hydrocarbon group, the substituted or unsubstituted monovalent aromatic heterocyclic group, and the substituted or unsubstituted amino group.

[0067] X 25 ~X 30 At least one of X has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. 25 ~X 30 If one of X has an unsubstituted amino group, 25 ~X 30 The number of unsubstituted amino groups contained in X is 1, and 25 ~X 30 does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group.

[0068] X 25 ~X 30 The preferred embodiment of X in the general formula (1) is as follows: 19 ~X 24 The explanation about this can be used.

[0069] Z 3 is CR 3 R 4, N.R. 5 , O, or S, and R 3 ~R 5 are each independently a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group.

[0070] Z 3 is preferably O or S from the viewpoint of durability of the electroluminescent device.

[0071] R 3 , R 4 , and R 5 As the substituted or unsubstituted monovalent aliphatic hydrocarbon group, the substituted or unsubstituted monovalent aromatic hydrocarbon group, or the substituted or unsubstituted monovalent aromatic heterocyclic group, R 2 The explanation about this can be used.

[0072] The general formula (6) will be explained below: The general formula (6) does not include the cases where it is represented by any of the general formulae (1) to (5) above.

[0073] In general formula (6), X 31 ~X 37 are each independently, CR 1 -R 2 , or N and X 31 ~X 37 At least one of them is N and X 31 ~X 37 Among them, CR 1 -R 2 The number of is greater than or equal to the number of N. 31 ~X 37 Among these, it is preferable that N is two or more.

[0074] R 1 are each independently a direct bond, -O-, -CO-, -COO-, or -SO2-. 2are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, provided that R 2 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R 1 is a direct bond.

[0075] R 2 The above explanation of general formula (1) can be applied to the substituted or unsubstituted monovalent aliphatic hydrocarbon group, the substituted or unsubstituted monovalent aromatic hydrocarbon group, the substituted or unsubstituted monovalent aromatic heterocyclic group, and the substituted or unsubstituted amino group.

[0076] X 31 ~X 37 At least one of X has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. 31 ~X 37 If one of X has an unsubstituted amino group, 31 ~X 37 The number of unsubstituted amino groups contained in X is 1, and 31 ~X 37 does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group.

[0077] X 31 ~X 37 The preferred embodiment of X in the general formula (1) is as follows: 19 ~X 24 The explanation about this can be used.

[0078] The compounds of the general formulas (1) to (6) preferably have an electron-withdrawing group in their structure, from the viewpoint of suppressing a decrease in luminance during long-term operation. Examples of the electron-withdrawing group include a halogen atom, a perfluoroalkyl group, a cyano group, and R 1 -R when is -CO-, -COO-, or -SO2- 1 -R 2 etc. A perfluoroalkyl group is one in which all hydrogen atoms in the alkyl chain are replaced with fluorine atoms, and is represented by -(CF2) n It is represented by -CF3 (n is any integer), and n is preferably in the range of 0 to 18. Examples of perfluoroalkyl groups include a trifluoromethyl group, a pentafluoroethyl group, a pentadecafluorooctyl group, and a heptatriacontafluorooctadecyl group. As the electron-withdrawing group, a fluorine atom, a trifluoromethyl group, and a cyano group are particularly preferred.

[0079] The compounds of general formulas (1) to (6) are R 1 is a direct bond and R 2 -R is a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. 1 -R 2 From the viewpoint of luminous efficiency, it is preferable to have the following. This is thought to be because carrier transfer between the ligand and the quantum dot is excellent.

[0080] From the viewpoint of ink stability and film-forming properties, the number of carboxy groups, sulfonic acid groups, phosphonic acid groups, or unsubstituted amino groups that the compounds of general formulas (1) to (6) have is preferably one.

[0081] From the viewpoint of avoiding coloration, the compounds of general formulas (1) to (6) preferably do not contain an alkoxy group, a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, an N-indolyl group, a 2-indolyl group, a 3-carbazolyl group, or an N-carbazolyl group. In particular, the compounds of general formulas (1) to (6) preferably do not contain a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, an N-indolyl group, a 2-indolyl group, a 3-carbazolyl group, or an N-carbazolyl group.

[0082] Specific examples of the treating agent include, but are not limited to, those listed in Tables 1 to 142. In the structural formulas below, when cis- and trans-geometric isomers exist, the agent may be either the cis- or trans-form, or a mixture of the cis- and trans-form isomers. The same applies to syn-anti geometric isomerism.

[0083] <Ink composition> The quantum dot-containing ink composition of the present invention contains the above-mentioned quantum dots and a dispersion medium. The dispersion medium is used to disperse the quantum dots and to facilitate coating the quantum dots of the present invention on a substrate such as a glass substrate so as to have a desired dry film thickness.

[0084] (dispersion medium) The dispersion medium is not particularly limited, and examples thereof include 1,2,3-trichloropropane, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, and 3-methoxymethyl-1,3-propanediol. dibutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylacetamide, N,N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, N-methylpyrrolidone, toluene, octane, nonane, hexane, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, water, methanol, ethanol ethanol, isopropyl alcohol, tert-tert-butanol, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotert-butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone,Examples of the dispersion medium include dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methylcyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, and dibasic acid esters. These dispersion media can be used alone or in combination of two or more in any ratio as needed.

[0085] The viscosity of the ink composition of the present invention may be adjusted using a dispersion medium, resin, polymerizable monomer, etc. When the ink composition of the present invention is used as an inkjet ink, it is preferable to adjust the viscosity at 25°C to 3 to 50 mPa·s. Furthermore, depending on the physical properties required for the printed matter, resins, crosslinking agents, polymerizable monomers, photosensitive substances, thermosensitive substances, etc. may be added to the ink composition.

[0086] <Electroluminescent device> The quantum dot-containing layer of the present invention can be used as a light-emitting layer in an electroluminescent device. The electroluminescent device has a substrate, a cathode and an anode provided on the substrate, and a light-emitting layer between the two electrodes. Furthermore, due to the nature of the light-emitting device, at least one of the anode and the cathode is transparent.

[0087] A preferred embodiment of the layered structure of the light-emitting element is one in which a hole transport layer, a light-emitting layer, and an electron transport layer are stacked in this order from the anode side. Furthermore, a charge blocking layer or the like may be present between the hole transport layer and the light-emitting layer, or between the light-emitting layer and the electron transport layer. A hole injection layer may be present between the anode and the hole transport layer, and an electron injection layer may be present between the cathode and the electron transport layer. The light-emitting layer may be a single layer, or may be divided into a first light-emitting layer, a second light-emitting layer, a third light-emitting layer, or the like. Furthermore, each layer may be divided into multiple sublayers. Representative element configurations of multilayer electroluminescent devices include: (1) anode / hole injection layer / light-emitting layer / cathode; (2) anode / hole injection layer / hole transport layer / light-emitting layer / cathode; (3) anode / hole injection layer / light-emitting layer / electron injection layer / cathode; (4) anode / hole injection layer / hole transport layer / light-emitting layer / electron injection layer / cathode; (5) anode / hole injection layer / light-emitting layer / hole blocking layer / electron injection layer / cathode; and (6) anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron injection layer. Possible device configurations include (6) anode / light-emitting layer / hole-blocking layer / electron injection layer / cathode, (7) anode / light-emitting layer / hole-blocking layer / electron injection layer / cathode, (8) anode / light-emitting layer / electron injection layer / cathode, (9) anode / hole injection layer / hole transport layer / interlayer layer / light-emitting layer / cathode, (10) anode / hole injection layer / interlayer layer / light-emitting layer / electron injection layer / cathode, and (11) anode / hole injection layer / hole transport layer / interlayer layer / light-emitting layer / electron injection layer / cathode.

[0088] The substrate for forming the electroluminescent device may be, for example, a substrate used in a known organic EL device. The substrate may be a resin film or a gas barrier film, and the gas barrier films described in JP-A Nos. 2004-136466, 2004-148566, 2005-246716, and 2005-262529 may also be preferably used. The thickness of the substrate is not particularly limited, but is preferably 30 μm to 700 μm, more preferably 40 μm to 200 μm, and even more preferably 50 μm to 150 μm. In either case, the haze is preferably 3% or less, more preferably 2% or less, and even more preferably 1% or less, and the total light transmittance is preferably 70% or more, more preferably 80% or more, and even more preferably 90% or more.

[0089] <Anode> The anode generally functions as an electrode that supplies holes to an organic or inorganic compound layer. There are no particular limitations on its shape, structure, size, etc., and it can be appropriately selected from known electrode materials depending on the use and purpose of the light-emitting device. As mentioned above, the anode is usually provided as a transparent anode. Transparent anodes are described in detail in "New Developments in Transparent Electrode Films" edited by Yutaka Sawada, published by CMC (1999). When a plastic substrate with low heat resistance is used as the substrate, a transparent anode formed at a low temperature of 150°C or less using ITO, IZO, or IGZO is preferred.

[0090] <Cathode> The cathode generally functions as an electrode for injecting electrons into an organic or inorganic compound layer. There are no particular limitations on its shape, structure, size, etc., and it can be appropriately selected from known electrode materials depending on the application and purpose of the light-emitting device. Examples of materials constituting the cathode include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Specific examples include Group II metals (e.g., Mg, Ca, etc.), gold, silver, lead, aluminum, lithium-aluminum alloys, magnesium-silver alloys, and rare earth metals such as indium and ytterbium. While these materials may be used alone, two or more can be suitably used in combination to achieve both stability and electron injection properties.

[0091] Among these, materials mainly composed of aluminum are preferred as materials for constituting the cathode. Materials mainly composed of aluminum include aluminum alone and alloys of aluminum and 0.01 to 100 mass% of an alkali metal or Group II metal (e.g., lithium-aluminum alloy, magnesium-aluminum alloy, etc.). Cathode materials are described in detail in JP-A-2-15595 and JP-A-5-121172. A dielectric layer of a fluoride or oxide of an alkali metal or Group II metal with a thickness of 0.1 to 5 nm may be inserted between the cathode and the organic compound or inorganic compound layer. This dielectric layer can also be considered as a type of electron injection layer.

[0092] The thickness of the cathode can be appropriately selected depending on the material constituting the cathode and cannot be generally specified, but is usually about 10 nm to 5 μm, and preferably 50 nm to 1 μm. The cathode may be transparent or opaque. A transparent cathode can be formed by depositing a thin film of the cathode material to a thickness of 1 to 10 nm and then laminating a transparent conductive material such as ITO, IZO, or IGZO on top.

[0093] <Light-emitting layer> The light-emitting layer is a layer that, upon application of an electric field, receives holes from the anode, hole injection layer, or hole transport layer and electrons from the cathode, electron injection layer, or electron transport layer, providing a site for recombination of holes and electrons to emit light. The light-emitting layer may be composed solely of the quantum dots of the present invention, or may be a mixed layer of quantum dots and a host material. The light-emitting material may further contain a fluorescent material and / or a phosphorescent material, and the dopant may be one or more types. The host material is preferably a charge transport material. The host material may be one or more types, such as a mixture of an electron-transporting host material and a hole-transporting host material. The light-emitting layer may further contain a material that does not have charge transport properties and does not emit light. The light-emitting layer may also be one layer or two or more layers, and each layer may emit light of a different color.

[0094] Examples of fluorescent materials include benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives, condensed aromatic compounds, perinone derivatives, oxadiazole derivatives, oxazine derivatives, aldazine derivatives, pyridine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styrylamine derivatives, diketopyrrolopyrrole derivatives, aromatic dimethylidine compounds, various metal complexes typified by metal complexes of 8-quinolinol derivatives and metal complexes of pyrromethene derivatives, polymer compounds such as polythiophene, polyphenylene, and polyphenylenevinylene, and compounds such as organosilane derivatives.

[0095] Examples of phosphorescent materials include complexes containing transition metal atoms or lanthanoid atoms. The transition metal atoms are not particularly limited, but preferably include ruthenium, rhodium, palladium, tungsten, rhenium, osmium, iridium, and platinum, and more preferably include rhenium, iridium, and platinum. Examples of lanthanoid atoms include lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium. Among these lanthanoid atoms, neodymium, europium, and gadolinium are preferred.

[0096] Examples of the ligand for the complex include those described in G. Wilkinson et al., Comprehensive Coordination Chemistry, published by Pergamon Press in 1987; H. Yersin, "Photochemistry and Photophysics of Coordination Compounds," published by Springer-Verlag in 1987; and Akio Yamamoto, "Organometallic Chemistry - Fundamentals and Applications," published by Shokabosha in 1982.

[0097] Examples of the host material contained in the light-emitting layer include those having a carbazole skeleton, a diarylamine skeleton, a pyridine skeleton, a pyrazine skeleton, a triazine skeleton, and an arylsilane skeleton, as well as materials exemplified in the sections on the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer described later.

[0098] <Hole injection layer, hole transport layer> The hole injection layer and the hole transport layer are layers having the function of receiving holes from the anode or the anode side and transporting them to the cathode side. As long as they have the above-mentioned function, they may be made of an organic compound or an inorganic compound, a low-molecular-weight compound, a high-molecular-weight compound, or a metal oxide. Specifically, the hole injection layer and the hole transport layer are preferably layers containing low molecular weight compounds such as carbazole derivatives, triphenylamine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidine compounds, porphyrin compounds, phthalocyanine compounds, and organic silane derivatives; carbon compounds such as carbon and fullerene; inorganic compounds made of metal oxides such as vanadium pentoxide and molybdenum trioxide; and polymer compounds such as polyvinylcarbazole, polypyrrole, and poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT-PSS).

[0099] <Electron injection layer, electron transport layer> The electron injection layer and the electron transport layer are layers that have the function of receiving electrons from the cathode or the cathode side and transporting them to the anode side. Specifically, the electron injection layer and the electron transport layer are preferably layers containing triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, aromatic ring tetracarboxylic acid anhydrides such as naphthalene and perylene, phthalocyanine derivatives, various metal complexes typified by metal complexes of 8-quinolinol derivatives, metal phthalocyanines, metal complexes having benzoxazole or benzothiazole as a ligand, low molecular weight compounds such as organosilane derivatives, metal oxides such as zinc oxide (ZnO) and titanium oxide (TiO), and alkali metal-doped organic or inorganic compounds, and in particular, magnesium-doped zinc oxide (ZnMgO) is preferred.

[0100] <Hole-blocking layer> The hole-blocking layer has the function of preventing holes transported from the anode side to the light-emitting layer from passing through to the cathode side. In the present invention, a hole-blocking layer can be provided as an organic compound layer adjacent to the light-emitting layer on the cathode side. In addition, the electron-transporting layer and / or the electron-injecting layer may also function as the hole-blocking layer. Examples of organic compounds that can be used to form the hole-blocking layer include aluminum complexes such as BAlq, triazole derivatives, and phenanthroline derivatives such as BCP. A layer that prevents electrons transported from the cathode to the light-emitting layer from passing through to the anode can also be provided adjacent to the light-emitting layer on the anode side. The hole-transporting layer and / or hole-injecting layer may also perform this function. [Example]

[0101] The present invention will be described in more detail below with reference to examples, but the technical scope of the present invention is not limited by these examples. In the examples, "parts" and "%" represent "parts by mass" and "% by mass", respectively, unless otherwise specified.

[0102] <Production of Quantum Dot-Containing Composition> [Synthesis Example 1] An additive solution was prepared by heating and dissolving 0.55 parts of anhydrous zinc acetate, 7.0 parts of dodecanethiol (treatment agent R1), and 5.0 parts of oleylamine. Separately, 0.22 parts of indium chloride and 8.25 parts of octylamine were placed in a reaction vessel and heated to 165°C while bubbling with nitrogen. After the indium chloride was dissolved, 0.86 parts of diethylaminophosphine was added to the reaction vessel and the mixture was maintained at 165°C for 20 minutes. The mixture was then cooled to 40°C. Next, the additive solution was added to the reaction vessel, heated to 240°C for 2 hours, and then allowed to cool to 25°C. After cooling, the mixture was purified by reprecipitation using hexane and ethanol to obtain quantum dots EX1, which consisted of core-shell semiconductor particles with an InP core and a ZnS shell surface-treated with dodecanethiol.

[0103] [Synthesis Example 2] 2.0 mL of oleic acid and 10 mL of 1-octadecene were added to the flask, and the mixture was heated and stirred at 100°C under reduced pressure and degassed for 1 hour. Nitrogen was then purged into the flask, and the mixture was heated to 270°C. Once the solution temperature stabilized, 0.2 mL of a tellurium / trioctylphosphine solution (prepared separately by adding tellurium to trioctylphosphine and dissolving it to a concentration of 0.3 M) and 0.8 mL of a selenium / trioctylphosphine solution (prepared by adding selenium to trioctylphosphine and dissolving it to a concentration of 0.3 M) were added to the flask. 0.3 mmol of diethylzinc solution was then added, and the mixture was maintained at 270°C for 30 minutes to synthesize ZnTeSe core semiconductor particles. In a separate flask, 3.0 g (4.74 mmol) of zinc stearate and 15 mL of octadecene were added, heated to 100°C, dissolved, and then stirred under vacuum for 1 hour to degas a zinc precursor solution. 10 mL (3.16 mmol) of the zinc precursor solution and 2.4 mL (0.3 mmol) of a 1.25 M selenium / trioctylphosphine solution prepared in a separate flask were simultaneously added to the reaction solution at 270°C in the flask where the ZnTeSe core semiconductor particles had been synthesized, and the reaction solution was stirred for 30 minutes. Next, 0.16 g (5.0 mmol) of sulfur was added to 4.0 mL of trioctylphosphine and heated to 150 °C to dissolve it, preparing a 1.25 M sulfur / trioctylphosphine solution. 1.0 mL of this solution was added to the reaction mixture and stirred for 1 hour. Next, 0.22 g (1.1 mmol) of zinc acetate was added to the reaction mixture and dissolved by heating to 100 °C under reduced pressure. The flask was again purged with nitrogen, and the temperature was raised to 230 °C. 0.48 mL (2 mmol) of dodecanethiol was added and the mixture was maintained for 1 hour. The resulting reaction solution was cooled to 25 °C. After cooling, the mixture was purified by reprecipitation using toluene and ethanol to obtain core-shell semiconductor particles (EX2) with a ZnTeSe core and a ZnSe / ZnS bilayer shell treated with dodecanethiol.

[0104] [Synthesis Example 3] A flask was charged with 0.033 g (0.20 mmol) of silver(I) acetate, 0.058 g (0.20 mmol) of indium acetate, 0.65 mL (2.7 mmol) of 1-dodecanethiol, and 4.0 mL of oleylamine. The mixture was heated and stirred at 100°C under reduced pressure for 1 hour. Nitrogen was then purged into the flask, and the mixture was heated to 200°C and maintained at this temperature for 20 minutes. The flask was then heated to 230°C, and 1.0 mL of a separately prepared 1.25 M sulfur / trioctylphosphine solution was added to the reaction solution, followed by stirring for 1 hour. Finally, 0.066 g (0.36 mmol) of zinc acetate, 0.24 mL (0.76 mmol) of oleic acid, and 0.15 mL of oleylamine were added to the flask, followed by heating and stirring at 230°C for 1 hour. The resulting solution was cooled to 25°C. After cooling, the mixture was purified by reprecipitation using Toluene and ethanol to obtain quantum dots EX3, which are core-shell semiconductor particles with a core of AgInS2 and a shell of ZnS, surface-treated with dodecanethiol.

[0105] [Example 1] (Quantum dots and ink compositions) The quantum dots EX1 obtained in Synthesis Example 1 were diluted with toluene to a solids concentration of 1%. The same amount of a 5% toluene solution of Treatment Agent 1 (Table 1) was added and stirred for 12 hours. Purification was performed by reprecipitation using toluene and ethanol. Mesitylene was used to adjust the solids concentration to 10% to obtain ink composition 1, which contained quantum dots in which core-shell semiconductor particles with an InP core and a ZnS shell were surface-treated with Treatment Agent 1. The average particle size of the semiconductor particles was measured for quantum dots separated from the resulting ink composition 1. A scanning transmission electron microscope equipped with energy dispersive X-ray analysis was used to identify the semiconductor particle portion, and the particle size of the semiconductor particles was measured, taking advantage of the fact that the semiconductor particle portion appears dark in transmission electron microscope images relative to the surface treatment agent due to differences in electron density. Specifically, the minor and major axis diameters of the semiconductor particles were measured, and the average of the minor and major axis diameters was used as the particle size of the semiconductor particles. The average value was calculated for 30 randomly selected semiconductor particles to determine the average particle size of the semiconductor particles. The average particle size of the semiconductor particles contained in the quantum dots EX1 was 13 nm.

[0106] [Examples 2 to 414, Comparative Examples 1 to 3] Ink compositions 2 to 414 and ink compositions R1 to R3 containing quantum dots in which core-shell semiconductor particles having an InP core and a ZnS shell were surface-treated with a treating agent were obtained in the same manner as in Example 1, except that treating agent 1 was changed to treating agents 2 to 414 and treating agents R1 to R3 shown in Tables 1 to 61. Ink compositions 2 to 414 are ink compositions of the present invention, and ink compositions R1 to R3 are comparative ink compositions that are not ink compositions of the present invention.

[0107] [Example 415] Ink composition 415 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was replaced with treatment agent 5 in Table 1. The procedure was changed to that of Example 1, whereby an ink composition 415 containing quantum dots in which core-shell type semiconductor particles having a core of ZnTeSe and a double-layered ZnSe / ZnS shell were surface-treated with treatment agent 5 was obtained.

[0108] [Example 416] Ink composition 416 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was replaced with treatment agent 110 shown in Table 11. The procedure was changed to that of Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was changed to treatment agent 110 shown in Table 11.

[0109] [Example 417] Ink composition 417 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX2 obtained in Synthesis example 2, and treatment agent 1 was replaced with treatment agent 178 in Table 19. The procedure was changed to that of Example 1, whereby core-shell semiconductor particles having a core of ZnTeSe and a double-layered ZnSe / ZnS shell were surface-treated with treatment agent 178.

[0110] [Example 418] Ink composition 418 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was replaced with treatment agent 215 shown in Table 24. The procedure was changed to that of Example 1, whereby an ink composition 418 containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a double-layered ZnSe / ZnS shell were surface-treated with treatment agent 215.

[0111] [Example 419] Ink composition 419 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX2 obtained in Synthesis example 2, and treatment agent 1 was replaced with treatment agent 269 shown in Table 35. The procedure was changed to that of Example 1, whereby core-shell semiconductor particles having a core of ZnTeSe and a double-layered ZnSe / ZnS shell were surface-treated with treatment agent 269.

[0112] [Example 420] Ink composition 420 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was replaced with treatment agent 329 in Table 46. The procedure was changed to that of Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was changed to treatment agent 329 in Table 46. The procedure was changed to that of Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 was replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was changed to treatment agent 329 in Table 46.

[0113] [Example 421] Ink composition 421 containing quantum dots in which core-shell semiconductor particles having a core of AgInS2 and a shell of ZnS were surface-treated with treatment agent 28 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and treatment agent 1 was replaced with treatment agent 28 shown in Table 3.

[0114] [Example 422] Ink composition 422 containing quantum dots in which core-shell semiconductor particles having a core of AgInS2 and a shell of ZnS were surface-treated with treatment agent 147 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 147 in Table 15.

[0115] [Example 423] Ink composition 423 containing quantum dots in which core-shell semiconductor particles having a core of AgInS2 and a shell of ZnS were surface-treated with treatment agent 166 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 166 in Table 20.

[0116] [Example 424] Ink composition 424 containing quantum dots in which core-shell semiconductor particles having a core of AgInS2 and a shell of ZnS were surface-treated with treatment agent 216 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and treatment agent 1 was replaced with treatment agent 216 shown in Table 25.

[0117] [Example 425] Ink composition 425 containing quantum dots in which core-shell semiconductor particles having a core of AgInS2 and a shell of ZnS were surface-treated with treatment agent 273 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 273 in Table 36.

[0118] [Example 426] Ink composition 426 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and treatment agent 1 was replaced with treatment agent 364 in Table 51. The procedure was changed to that of Example 1, whereby ink composition 426 contained quantum dots in which core-shell semiconductor particles having an AgInS core and a ZnS shell were surface-treated with treatment agent 364.

[0119] [Examples 427 to 662] Ink compositions 427 to 662 containing quantum dots in which core-shell semiconductor particles having an InP core and a ZnS shell were surface-treated with a treating agent were obtained in the same manner as in Example 1, except that treating agent 1 was changed to treating agents 415 to 650 shown in Tables 62 to 100.

[0120] [Example 663] Ink composition 663 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was replaced with treatment agent 418 shown in Table 62. The procedure was changed to that of Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 was replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was changed to treatment agent 418 shown in Table 62.

[0121] [Example 664] Ink composition 664 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was replaced with treatment agent 419 in Table 62. The procedure was changed to that of Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 was replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was changed to treatment agent 419 in Table 62.

[0122] [Example 665] Ink composition 665 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was replaced with treatment agent 420 shown in Table 62. The procedure was changed to that of Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 was replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was changed to treatment agent 420 shown in Table 62.

[0123] [Example 666] Ink composition 666 was obtained in the same manner as in Example 1, except that quantum dots EX1 obtained in Synthesis Example 1 were replaced with quantum dots EX2 obtained in Synthesis Example 2, and treating agent 1 was replaced with treating agent 477 shown in Table 72. The procedure was changed to that of Example 1, except that quantum dots EX1 obtained in Synthesis Example 1 was replaced with quantum dots EX2 obtained in Synthesis Example 2, and treating agent 1 was changed to treating agent 477 shown in Table 72.

[0124] [Example 667] Ink composition 667 was obtained in the same manner as in Example 1, except that quantum dots EX1 obtained in Synthesis Example 1 were replaced with quantum dots EX2 obtained in Synthesis Example 2, and treating agent 1 was replaced with treating agent 478 shown in Table 72. The procedure was changed to that of Example 1, except that quantum dots EX1 obtained in Synthesis Example 1 was replaced with quantum dots EX2 obtained in Synthesis Example 2, and treating agent 1 was changed to treating agent 478 shown in Table 72.

[0125] [Example 668] Ink composition 668 was obtained in the same manner as in Example 1, except that quantum dots EX1 obtained in Synthesis example 1 were replaced with quantum dots EX2 obtained in Synthesis example 2, and treating agent 1 was replaced with treating agent 479 in Table 72. The procedure was changed to that of Example 1, whereby ink composition 668 contained quantum dots in which core-shell semiconductor particles each having a ZnTeSe core and a two-layer ZnSe / ZnS shell were surface-treated with treating agent 479.

[0126] [Example 669] Ink composition 669 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX2 obtained in Synthesis example 2, and treatment agent 1 was replaced with treatment agent 522 shown in Table 79. The procedure was changed to that of Example 1, whereby an ink composition 669 containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a double-layered ZnSe / ZnS shell were surface-treated with treatment agent 522 was obtained.

[0127] [Example 670] Ink composition 670 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was replaced with treatment agent 523 shown in Table 79. The procedure was changed to that of Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 was replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was changed to ...

[0128] [Example 671] Ink composition 671 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX2 obtained in Synthesis example 2, and treatment agent 1 was replaced with treatment agent 524 in Table 79. The procedure was changed to that of Example 1, whereby an ink composition 671 containing quantum dots in which core-shell type semiconductor particles having a core of ZnTeSe and a double-layered ZnSe / ZnS shell were surface-treated with treatment agent 524.

[0129] [Example 672] Ink composition 672 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX2 obtained in Synthesis example 2, and treatment agent 1 was replaced with treatment agent 555 shown in Table 84. The procedure was changed to that of Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX2 obtained in Synthesis example 2, and treatment agent 1 was changed to treatment agent 555 shown in Table 84.

[0130] [Example 673] Ink composition 673 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX2 obtained in Synthesis example 2, and treatment agent 1 was replaced with treatment agent 553 shown in Table 84. The procedure was changed to that of Example 1, whereby ink composition 673 contained quantum dots in which core-shell type semiconductor particles having a core of ZnTeSe and a double-layered ZnSe / ZnS shell were surface-treated with treatment agent 553.

[0131] [Example 674] Ink composition 674 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX2 obtained in Synthesis example 2, and treatment agent 1 was replaced with treatment agent 554 in Table 84. The procedure was changed to that of Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX2 obtained in Synthesis example 2, and treatment agent 1 was changed to treatment agent 554 in Table 84.

[0132] [Example 675] Ink composition 675 was obtained in the same manner as in Example 1, except that quantum dots EX1 obtained in Synthesis example 1 were replaced with quantum dots EX2 obtained in Synthesis example 2, and treating agent 1 was replaced with treating agent 588 in Table 89. The procedure was changed to that of Example 1, whereby ink composition 675 contained quantum dots in which core-shell type semiconductor particles each having a core of ZnTeSe and a double-layered ZnSe / ZnS shell were surface-treated with treating agent 588.

[0133] [Example 676] Ink composition 676 was obtained in the same manner as in Example 1, except that quantum dots EX1 obtained in Synthesis example 1 were replaced with quantum dots EX2 obtained in Synthesis example 2, and treating agent 1 was replaced with treating agent 589 in Table 89. The procedure was changed to that of Example 1, whereby ink composition 676 contained quantum dots in which core-shell type semiconductor particles each having a core of ZnTeSe and a double-layered ZnSe / ZnS shell were surface-treated with treating agent 591.

[0134] [Example 677] Ink composition 677 was obtained in the same manner as in Example 1, except that quantum dots EX1 obtained in Synthesis example 1 were replaced with quantum dots EX2 obtained in Synthesis example 2, and treating agent 1 was replaced with treating agent 590 shown in Table 89. The procedure was changed to that of Example 1, whereby ink composition 677 contained quantum dots in which core-shell type semiconductor particles each having a core of ZnTeSe and a double-layered ZnSe / ZnS shell were surface-treated with treating agent 590.

[0135] [Example 678] Ink composition 678 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was replaced with treatment agent 622 shown in Table 95. The procedure was changed to that of Example 1, whereby an ink composition 678 containing quantum dots was obtained in which core-shell semiconductor particles, each having a core of ZnTeSe and a double-layered ZnSe / ZnS shell, were surface-treated with treatment agent 622.

[0136] [Example 679] Ink composition 679 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX2 obtained in Synthesis example 2, and treatment agent 1 was replaced with treatment agent 623 shown in Table 95. The procedure was changed to that of Example 1, whereby an ink composition 679 containing quantum dots was obtained in which core-shell semiconductor particles, each having a core of ZnTeSe and a double-layered ZnSe / ZnS shell, were surface-treated with treatment agent 623.

[0137] [Example 680] Ink composition 680 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was replaced with treatment agent 624 shown in Table 96. The procedure was changed to that of Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with quantum dots EX2 obtained in Synthesis Example 2, and treatment agent 1 was changed to treatment agent 624 shown in Table 96.

[0138] [Example 681] Ink composition 681 containing quantum dots in which core-shell semiconductor particles having a core of AgInS2 and a shell of ZnS were surface-treated with treatment agent 418 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 418 shown in Table 62.

[0139] [Example 682] Ink composition 682 containing quantum dots in which core-shell semiconductor particles having a core of AgInS2 and a shell of ZnS were surface-treated with treatment agent 419 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 419 in Table 62.

[0140] [Example 683] Ink composition 683 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 420 shown in Table 62. The procedure was changed to that of Example 1, whereby an ink composition 683 containing quantum dots was obtained in which core-shell semiconductor particles having an AgInS core and a ZnS shell were surface-treated with treatment agent 420.

[0141] [Example 684] Ink composition 684 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 477 in Table 72. The procedure was changed to that of Example 1, whereby an ink composition 684 containing quantum dots was obtained in which core-shell semiconductor particles having an AgInS2 core and a ZnS shell were surface-treated with treatment agent 477.

[0142] [Example 685] Ink composition 685 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 478 in Table 72. The procedure was changed to that of Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was changed to treatment agent 478 in Table 72.

[0143] [Example 686] Ink composition 686 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 479 in Table 72. The procedure was changed to that of Example 1, whereby an ink composition 686 containing quantum dots was obtained in which core-shell semiconductor particles having an AgInS core and a ZnS shell were surface-treated with treatment agent 479.

[0144] [Example 687] Ink composition 687 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 522 in Table 79. The procedure was changed to that of Example 1, whereby an ink composition 687 containing quantum dots was obtained in which core-shell semiconductor particles having an AgInS core and a ZnS shell were surface-treated with treatment agent 522.

[0145] [Example 688] Ink composition 688 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 523 in Table 79. The procedure was changed to that of Example 1, whereby an ink composition 688 containing quantum dots in which core-shell semiconductor particles having an AgInS core and a ZnS shell were surface-treated with treatment agent 523 was obtained.

[0146] [Example 689] Ink composition 689 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 524 in Table 79. The procedure was changed to that of Example 1, whereby an ink composition 689 containing quantum dots in which core-shell semiconductor particles having an AgInS core and a ZnS shell were surface-treated with treatment agent 524 was obtained.

[0147] [Example 690] Ink composition 690 containing quantum dots in which core-shell semiconductor particles having a core of AgInS2 and a shell of ZnS were surface-treated with treatment agent 555 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 555 shown in Table 84.

[0148] [Example 691] Ink composition 691 containing quantum dots in which core-shell semiconductor particles having a core of AgInS2 and a shell of ZnS were surface-treated with treatment agent 553 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 553 in Table 84.

[0149] [Example 692] Ink composition 692 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 554 in Table 84. The procedure was changed to that of Example 1, whereby an ink composition 692 containing quantum dots was obtained in which core-shell semiconductor particles having an AgInS core and a ZnS shell were surface-treated with treatment agent 554.

[0150] [Example 693] Ink composition 693 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 588 in Table 89. The procedure was changed to that of Example 1, whereby an ink composition 693 containing quantum dots was obtained in which core-shell semiconductor particles having an AgInS core and a ZnS shell were surface-treated with treatment agent 588.

[0151] [Example 694] Ink composition 694 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 589 in Table 89. The procedure was changed to that of Example 1, whereby an ink composition 694 containing quantum dots was obtained in which core-shell semiconductor particles having an AgInS core and a ZnS shell were surface-treated with treatment agent 589.

[0152] [Example 695] Ink composition 695 containing quantum dots in which core-shell semiconductor particles having a core of AgInS2 and a shell of ZnS were surface-treated with treatment agent 590 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 590 in Table 89.

[0153] [Example 696] Ink composition 696 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and treatment agent 1 was replaced with treatment agent 622 shown in Table 95. The procedure was changed to that of Example 1, whereby an ink composition 696 containing quantum dots was obtained in which core-shell semiconductor particles having an AgInS core and a ZnS shell were surface-treated with treatment agent 622.

[0154] [Example 697] Ink composition 697 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis example 1 were replaced with the quantum dots EX3 obtained in Synthesis example 3, and treatment agent 1 was replaced with treatment agent 623 shown in Table 95. The procedure was changed to that of Example 1, whereby an ink composition 697 containing quantum dots was obtained in which core-shell semiconductor particles having an AgInS core and a ZnS shell were surface-treated with treatment agent 623.

[0155] [Example 698] Ink composition 698 was obtained in the same manner as in Example 1, except that the quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and treatment agent 1 was replaced with treatment agent 624 shown in Table 96. The procedure was changed to that of Example 1, whereby an ink composition 698 containing quantum dots was obtained in which core-shell semiconductor particles having an AgInS core and a ZnS shell were surface-treated with treatment agent 624. [Examples 699 to 972] Ink compositions 699 to 972 containing quantum dots in which core-shell semiconductor particles having an InP core and a ZnS shell were surface-treated with a treating agent were obtained in the same manner as in Example 1, except that treating agent 1 was changed to treating agents 651 to 924 shown in Tables 101 to 142.

[0156] [Table 1]

[0157] [Table 2]

[0158] [Table 3]

[0159] [Table 4]

[0160] [Table 5]

[0161] [Table 6]

[0162] [Table 7]

[0163] Table 8

[0164] Table 9

[0165] Table 10

[0166] Table 11

[0167] Table 12

[0168] Table 13

[0169] Table 14

[0170] Table 15

[0171] Table 16

[0172] Table 17

[0173] Table 18

[0174] Table 19

[0175] Table 20

[0176] Table 21

[0177] Table 22

[0178] Table 23

[0179] Table 24

[0180] Table 25

[0181] Table 26

[0182] Table 27

[0183] Table 28

[0184] Table 29

[0185] Table 30

[0186] Table 31

[0187] Table 32

[0188] Table 33

[0189] Table 34

[0190] Table 35

[0191] Table 36

[0192] Table 37

[0193] Table 38

[0194] Table 39

[0195] Table 40

[0196] Table 41

[0197] Table 42

[0198] Table 43

[0199] Table 44

[0200] Table 45

[0201] Table 46

[0202] Table 47

[0203] Table 48

[0204] Table 49

[0205] Table 50

[0206] Table 51

[0207] Table 52

[0208] Table 53

[0209] Table 54

[0210] Table 55

[0211] Table 56

[0212] Table 57

[0213] Table 58

[0214] Table 59

[0215] Table 60

[0216] Table 61

[0217] Table 62

[0218] Table 63

[0219] Table 64

[0220] Table 65

[0221] Table 66

[0222] Table 67

[0223] Table 68

[0224] Table 69

[0225] Table 70

[0226] Table 71

[0227] Table 72

[0228] Table 73

[0229] Table 74

[0230] Table 75

[0231] Table 76

[0232] Table 77

[0233] Table 78

[0234] Table 79

[0235] Table 80

[0236] Table 81

[0237] Table 82

[0238] Table 83

[0239] Table 84

[0240] Table 85

[0241] Table 86

[0242] Table 87

[0243] Table 88

[0244] Table 89

[0245] Table 90

[0246] Table 91

[0247] Table 92

[0248] Table 93

[0249] Table 94

[0250] Table 95

[0251] Table 96

[0252] Table 97

[0253] Table 98

[0254] Table 99

[0255] Table 100

[0256] Table 101

[0257] Table 102

[0258] Table 103

[0259] Table 104

[0260] Table 105

[0261] Table 106

[0262] Table 107

[0263] Table 108

[0264] Table 109

[0265] Table 110

[0266] Table 111

[0267] Table 112

[0268] Table 113

[0269] Table 114

[0270] Table 115

[0271] Table 116

[0272] Table 117

[0273] Table 118

[0274] Table 119

[0275] Table 120

[0276] Table 121

[0277] Table 122

[0278]

Table 123

[0279] Table 124

[0280] Table 125

[0281] Table 126

[0282] Table 127

[0283] Table 128

[0284] Table 129

[0285] Table 130

[0286] Table 131

[0287] Table 132

[0288] Table 133

[0289] Table 134

[0290] Table 135

[0291] Table 136

[0292] Table 137

[0293] Table 138

[0294] Table 139

[0295] Table 140

[0296] Table 141

[0297] Table 142

[0298] (Ink stability evaluation) The stability of fluorescence quantum yield over time was evaluated for ink compositions 1 to 938 and ink compositions R1 to R3 obtained in the examples and comparative examples. A quantum efficiency measurement system QE-2000 manufactured by Otsuka Electronics Co., Ltd. was used to measure the fluorescence quantum yield. The ratio of the fluorescence quantum yield after storage in a sealed state in the atmosphere for 100 hours to the fluorescence quantum yield immediately after synthesis was taken as 1.0 was used as an index of ink stability. The results are shown in Tables 143 to 167. The criteria were as follows: A+: 1.0 or less, 0.80 or more A: Less than 0.80, 0.75 or more B+: Less than 0.75, 0.70 or more B: Less than 0.70, 0.65 or more C+: Less than 0.65, 0.60 or more C: Less than 0.60, 0.55 or more D+: Less than 0.55, 0.50 or more D: Less than 0.50

[0299] (Evaluation of long-term dispersion stability of ink) The long-term dispersion stability of ink compositions 1 to 938 and ink compositions R1 to R3 obtained in the examples and comparative examples was evaluated. Specifically, the ink compositions were sealed in a glove box filled with argon gas with an oxygen concentration of 1 ppm or less and a dew point of -80°C or less, and stored in an oven at 80°C for 480 hours. After that, the ink compositions were visually inspected for the presence or absence of turbidity or precipitation. The results are shown in Tables 143 to 167. A: No turbidity can be detected. B: Slight turbidity is observed. C: Turbid and sediment is observed. D: Aggregated and precipitated.

[0300] (Comparison of electroluminescent device characteristics made with ink before and after evaluation of long-term dispersion stability) For the ink compositions 1 to 938 and ink compositions R1 to R3 obtained in the examples and comparative examples, electroluminescent devices were produced using the inks before and after evaluation of long-term dispersion stability, and the device characteristics were compared. The electroluminescent device performance was evaluated by the following method. Vapor deposition (vacuum vapor deposition) was performed at 10 -6 The experiment was carried out in a vacuum of Torr without temperature control such as heating or cooling of the substrate. The light-emitting characteristics of the device were measured using an electroluminescent device with a light-emitting device area of ​​2 mm x 2 mm.

[0301] A 2.3-2.7% by mass dispersion of molybdenum oxide nanoparticles (purchased from Sigma-Aldrich) was spin-coated onto a cleaned glass plate equipped with an ITO electrode, followed by drying at 150°C for 20 minutes to form a hole injection layer with a thickness of 20 nm. Poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] was then dissolved in monochlorobenzene at a concentration of 1.0% by mass, spin-coated onto the substrate, and dried at 110°C for 20 minutes to form a hole transport layer with a thickness of 35 nm. The ink compositions of the present invention obtained in the Examples and Comparative Examples were diluted 20-fold with mesitylene, spin-coated onto the substrate, and dried at 25°C for 5 minutes in a nitrogen atmosphere to form a 25-nm light-emitting layer. An isopropanol dispersion of zinc oxide nanoparticles N-10 (Avantama) was applied thereon by spin coating, and then heated and dried on a hot plate at 80°C for 20 minutes to form an 80 nm electron transport layer. Finally, aluminum (Al) was deposited to a thickness of 200 nm to form an electrode, yielding an electroluminescent device. The resulting device was measured at a current density of 10 (mA / cm 2 The luminous efficiency (cd / A) when driven at 1000 kJ / s was measured, and the luminous efficiency of the element fabricated with the ink before the long-term dispersion stability evaluation was divided by the luminous efficiency of the element fabricated with the ink after the long-term dispersion stability evaluation. The results are shown in Tables 143 to 167. A: 0.80 or more B: Less than 0.80, 0.60 or more C: Less than 0.60 D: The ink coagulated and the element could not be created, or the element did not light up.

[0302] (Evaluation of ink film forming properties) The film-forming properties of ink compositions 1 to 698 and R1 to R3 obtained in the examples and comparative examples were evaluated. After cleaning with an electronics industry detergent and solvent, a glass substrate was further treated with UV ozone, and the ink composition was spin-coated onto the substrate, followed by heat treatment on a hot plate at 80°C to form a film. The arithmetic mean roughness (Ra) (nm) of the formed film was determined according to the method specified in Japanese Industrial Standard (JIS) R1683:2014, and evaluated according to the following criteria. The results are shown in Tables 143 to 167. The criteria are as follows: A: 0 or more, 3.0 or less B: More than 3.0, less than 5.0 C: over 5.0, under 10.0 D: Exceeding 10.0

[0303] (Evaluation of electroluminescent devices) The electroluminescent device performance of the ink compositions 1 to 938 and ink compositions R1 to R3 obtained in the examples and comparative examples was evaluated by the following method. -6 The experiment was carried out in a vacuum of Torr without temperature control such as heating or cooling of the substrate. The light-emitting characteristics of the device were measured using an electroluminescent device with a light-emitting element area of ​​2 mm x 2 mm. The results are shown in Tables 143 to 167.

[0304] A 2.3-2.7% by mass dispersion of molybdenum oxide nanoparticles (purchased from Sigma-Aldrich) was spin-coated onto a cleaned glass plate equipped with an ITO electrode, followed by drying at 150°C for 20 minutes to form a hole injection layer with a thickness of 20 nm. Poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] was then dissolved in monochlorobenzene at a concentration of 1.0% by mass, spin-coated onto the substrate, and dried at 110°C for 20 minutes to form a hole transport layer with a thickness of 35 nm. The ink compositions of the present invention obtained in the Examples and Comparative Examples were diluted 20-fold with mesitylene, spin-coated onto the substrate, and dried at 25°C for 5 minutes in a nitrogen atmosphere to form a 25-nm light-emitting layer. An isopropanol dispersion of zinc oxide nanoparticles N-10 (Avantama) was applied thereon by spin coating, and then heated and dried on a hot plate at 80°C for 20 minutes to form an 80 nm electron transport layer. Finally, aluminum (Al) was deposited to a thickness of 200 nm to form an electrode, yielding an electroluminescent device. The resulting device was measured at a current density of 10 (mA / cm 2 The luminous efficiency (cd / A) when driven at 6 V and the relative luminance (= (luminance after 100 hours) / (initial luminance)) after 100 hours of continuous driving were measured. The results are shown in Tables 69 to 79. When the ink composition of Example 1 was used, the external quantum efficiency was 4.8% and the luminous luminance was 28,000 (cd / m) at 6 V. 2 The peak wavelength of the emission spectrum was 615 nm, and the full width at half maximum was 28 nm. The evaluation criteria for the luminous efficiency (cd / A) and the relative brightness after 100 hours of continuous operation are as follows:

[0305] Luminous efficacy (cd / A) A+: 5.5 or above A: Less than 5.5, 5.0 or more B+: Less than 5.0, 4.5 or more B: Less than 4.5, 4.0 or more C+: Less than 4.0, 3.5 or above C: Less than 3.5, 3.0 or more D+: Less than 3.0, 2.0 or more D: Less than 2.0

[0306] Relative luminance A+: 1.0 or less, 0.70 or more A: Less than 0.70, 0.65 or more B+: Less than 0.65, 0.60 or more B: Less than 0.60, 0.55 or more C+: Less than 0.55, 0.50 or more C: Less than 0.50, 0.45 or more D+: Less than 0.45, 0.30 or more D: Less than 0.30

[0307] [Table 143]

[0308] [Table 144]

[0309] [Table 145]

[0310] [Table 146]

[0311] [Table 147]

[0312] [Table 148]

[0313] [Table 149]

[0314] [Table 150]

[0315] Table 151

[0316] Table 152

[0317] Table 153

[0318] Table 154

[0319] Table 155

[0320] Table 156

[0321] Table 157

[0322] Table 158

[0323] Table 159

[0324] Table 160

[0325] Table 161

[0326] Table 162

[0327] Table 163

[0328] Table 164

[0329] Table 165

[0330] Table 166

[0331] Table 167

Claims

1. Quantum dots containing semiconductor particles surface-treated with a surface treatment agent, wherein the surface treatment agent contains a compound represented by any one of the following general formulas (1) to (6): 【Chemistry 1】 [In general formula (1), X １ ~X ６ are each independently C-R １ -R ２ , or N, X １ ~X ６ at least one of them is N, X １ ~X ６ Among them, C-R １ -R ２ is equal to or greater than the number N. R １ each independently represents a direct bond, —O—, —CO—, —COO—, or —SO ２ - is. R ２ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group. However, R ２ is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R １ is a direct bond. X １ ~X ６ At least one of these has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. However, X １ ~X ６ When one of X has an unsubstituted amino group, １ ~X ６ The number of unsubstituted amino groups contained in X is 1, and １ ~X ６ does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group.] 【Chemistry 2】 [In general formula (2), X ７ ~X １４ are each independently C-R １ -R ２ , or N, X ７ ~X １４ at least one of them is N, X ７ ~X １４ Among them, C-R １ -R ２ The number of is equal to or greater than the number of N. １ each independently represents a direct bond, —O—, —CO—, —COO—, or —SO ２ - is. R ２ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group. However, R ２ is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R １ is a direct bond. X ７ ~X １４ At least one of these has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. However, X ７ ~X １４ When one of X has an unsubstituted amino group, ７ ~X １４ The number of unsubstituted amino groups contained in X is 1, and ７ ~X １４ does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group. General formula (2) excludes the case where it is represented by general formula (1). 【Transformation 3】 [In general formula (3), X １５ ~X １８ are each independently C-R １ -R ２ , or N, X １５ ~X １８ at least one of them is N, X １５ ~X １８ Among them, C-R １ -R ２ is equal to or greater than the number N. R １ each independently represents a direct bond, —O—, —CO—, —COO—, or —SO ２ - is. R ２ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group. However, R ２ is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R １ is a direct bond. X １５ ~X １８ At least one of these has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. However, X １５ ~X １８ When one of X has an unsubstituted amino group, １５ ~X １８ The number of unsubstituted amino groups contained in X is 1, and １５ ~X １８ does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group. Z １ is CR ３ R ４ , N.R. ５ , O, or S, and R ３ ~R ５ are each independently a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group. General formula (3) excludes cases where it is represented by any of general formulas (1) and (2). 【Chemistry 4】 [In general formula (4), X １９ ~X ２４ are each independently C-R １ -R ２ , or N, X １９ ~X ２４ at least one of them is N, X １９ ~X ２４ Among them, C-R １ -R ２ is equal to or greater than the number N. R １ each independently represents a direct bond, —O—, —CO—, —COO—, or —SO ２ - is. R ２ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group. However, R ２ is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R １ is a direct bond. X １９ ~X ２４ At least one of these has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. However, X １９ ~X ２４ When one of X has an unsubstituted amino group, １９ ~X ２４ The number of unsubstituted amino groups contained in X is 1, and １９ ~X ２４ does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group. Z ２ is CR ３ R ４ , N.R. ５ , O, or S, and R ３ ~R ５ are each independently a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group. General formula (4) excludes cases where it is represented by any of general formulas (1) to (3). 【Transformation 5】 [In general formula (5), X ２５ ~X ３０ are each independently C-R １ -R ２ , or N, X ２５ ~X ３０ at least one of them is N, X ２５ ~X ３０ Among them, C-R １ -R ２ is equal to or greater than the number N. R １ each independently represents a direct bond, —O—, —CO—, —COO—, or —SO ２ - is. R ２ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group. However, R ２ is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R １ is a direct bond. X ２５ ~X ３０ At least one of these has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. However, X ２５ ~X ３０ When one of X has an unsubstituted amino group, ２５ ~X ３０ The number of unsubstituted amino groups contained in X is 1, and ２５ ~X ３０ does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group. Z ３ is CR ３ R ４ , N.R. ５ , O, or S, and R ３ ~R ５ are each independently a hydrogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group. General formula (5) excludes cases where it is represented by any of general formulas (1) to (4). 【Transformation 6】 [In general formula (6), X ３１ ~X ３７ are each independently C-R １ -R ２ , or N, X ３１ ~X ３７ at least one of them is N, X ３１ ~X ３７ Among them, C-R １ -R ２ is equal to or greater than the number N. R １ each independently represents a direct bond, —O—, —CO—, —COO—, or —SO ２ - is. R ２ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding residues of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group. However, R ２ is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfonic acid group, a phosphonic acid group, or a substituted or unsubstituted amino group, R １ is a direct bond. X ３１ ~X ３７ At least one of these has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. However, X ３１ ~X ３７ When one of X has an unsubstituted amino group, ３１ ~X ３７ The number of unsubstituted amino groups contained in X is 1, and ３１ ~X ３７ does not have a hydroxyl group, a thiol group, a carboxyl group, a sulfonic acid group, a phosphonic acid group, or a phosphinic acid group. General formula (6) excludes cases where it is represented by any of general formulas (1) to (5).

2. The quantum dot according to claim 1, wherein the surface treatment agent comprises a compound represented by any one of the following general formulas (7) to (9): 【Transformation 7】 [In general formula (7), R ５ ~R ７ are each independently -R ２２ -R ２３ and R ２２ each independently represents a direct bond, —O—, —CO—, or —COO—, R ２３ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding the case where they are a residue of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), or a substituted amino group. However, R ２３ is a hydrogen atom, a halogen atom, a cyano group, or a substituted amino group, R ２２ is a direct bond.] 【Transformation 8】 [In general formula (8), R ８ ~R １４ are each independently -R ２２ -R ２３ and R ２２ each independently represents a direct bond, —O—, —CO—, or —COO—, R ２３ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding the case where they are a residue of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), or a substituted amino group. However, R ２３ is a hydrogen atom, a halogen atom, a cyano group, or a substituted amino group, R ２２ is a direct bond.] 【Chemistry 9】 [In general formula (9), R １５ ~R ２１ and each independently represent -R ２２ -R ２３ and R ２２ each independently represents a direct bond, —O—, —CO—, or —COO—, R ２３ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic heterocyclic group (excluding the case where they are a residue of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine), or a substituted amino group. However, R ２３ is a hydrogen atom, a halogen atom, a cyano group, or a substituted amino group, R ２２ is a direct bond.]

3. An ink composition comprising the quantum dots according to claim 1 or 2 and a dispersion medium.

4. 3. An electroluminescent device having an anode, a light-emitting layer, and a cathode on a substrate, wherein the light-emitting layer contains the quantum dots according to claim 1.

Images