Quantum dots, electroluminescent element, and ink composition

Surface-treated quantum dots with compounds in specific formulas enhance luminous efficiency and stability in electroluminescent devices, addressing inefficiencies in existing quantum dot-based electroluminescent devices and ink compositions.

WO2026034600A1PCT designated stage Publication Date: 2026-02-12TOYO INK MFG CO LTD
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Patent Information

Application Number
PCT/JP2025/028174
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-09-24
Filing Date
2025-08-07
Publication Date
2026-02-12

AI Technical Summary

Technical Problem

Quantum dots used as light-emitting materials in electroluminescent devices suffer from insufficient luminous efficiency, stability, and film-forming properties, particularly when used in ink compositions.

Method used

Surface-treating semiconductor particles with a compound represented by specific general formulas, such as (1) to (6), to enhance electrical properties and stability, resulting in improved luminous efficiency and film-forming properties.

Benefits of technology

The treated quantum dots exhibit high luminous efficiency, maintain luminance over long-term operation, and provide stable ink compositions with minimal fluorescence quantum yield degradation.

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Abstract

Provided are: quantum dots having excellent stability which make it possible to attain high luminous efficiency when used as a light-emitting material of an electroluminescent element; an electroluminescent element containing said quantum dots; and an ink composition. The quantum dots contain semiconductor particles surface-treated with a surface treatment agent containing a compound represented by general formula (1).
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Description

Quantum dots, electroluminescent device and ink composition

[0001] The present disclosure relates to quantum dots, electroluminescent devices using the same, and ink compositions.

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

[0003] Quantum dots are small nanoscale semiconductor particles that exhibit behavior intermediate between that of atoms or molecules and that of macroscopic solids (bulk forms). Nanoscale materials (semiconductor particles) in which charge carriers and excitons are confined in all three dimensions are called quantum dots, and their effective band gap increases with decreasing size. That is, 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 regions 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-type organic EL devices using quantum dots made 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 enhancing 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.

[0005] JP 2004-315661 A JP 2008-214363 A

[0006] The problem to be solved by the present disclosure 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. It is also an object of the present disclosure to provide an electroluminescent device with high luminous efficiency and little decrease in luminance even when driven for a long period of time. It is also an object of the present disclosure 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.

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

[0008] [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): [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 the groups is N, and X 1 ~X 6 Among them, C-R 1 -R 2 The number of is equal to or greater than the number of N. 1each 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. 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. 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 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.] [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 the groups is N, and 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 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. 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. 7 ~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 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) does not include the case where it is represented by general formula (1). [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 the groups is N, and X 15 ~X 18 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 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. 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. 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 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. 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). [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 the groups is N, and X 19 ~X 24 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. 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. 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 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. 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). [In general formula (5), X 25 ~X 30 are each independently C-R 1 -R2 , or N, X 25 ~X 30 At least one of the groups is N, and X 25 ~X 30 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. 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. 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 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. 3 is CR 3 R 4 , N.R. 5 , O, or S, and R 3 ~R 5are 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). [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 the groups is N, and X 31 ~X 37 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. 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. 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 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 37does 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) does not include the 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): [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. 23 is a hydrogen atom, a halogen atom, a cyano group, or a substituted amino group, R 22 is a direct bond.] [In general formula (8), R 8 ~R 14 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. 23 is a hydrogen atom, a halogen atom, a cyano group, or a substituted amino group, R 22 is a direct bond.] [In general formula (9), R15 ~R 21 and each independently represent -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. 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].

[0012] The present disclosure provides 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 device. It also provides the excellent effect of providing an electroluminescent device with high luminous efficiency and little decrease in luminance during long-term operation. It also provides 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.

[0013] <Quantum Dots> The quantum dots of the present disclosure 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 disclosure will be described in detail below.

[0014] <Semiconductor Particles> Examples of materials for semiconductor particles include carbon (C) (amorphous carbon, graphite, graphene, carbon nanotubes, etc.), silicon (Si), germanium (Ge), tin (Sn), and other simple substances of group IV elements in the periodic table, phosphorus (P) (black phosphorus), and other simple substances of group V elements in the periodic table, selenium (Se), tellurium (Te), and other simple substances of group VI elements in the periodic table, tin oxide (IV), boron nitride (BN), boron phosphide (BP), boron arsenide (BAs), aluminum nitride (AlN), and lithium. compounds of elements in Group III of the periodic table and elements in Group V of the periodic table, such as aluminum sulphide (AlP), aluminum arsenide (AlAs), aluminum antimonide (AlSb), gallium nitride (GaN), gallium phosphide (GaP), gallium arsenide (GaAs), gallium antimonide (GaSb), indium nitride (InN), indium phosphide (InP), indium arsenide (InAs), and indium antimonide (InSb); 2 S 3 ), aluminum selenide (Al 2 Se 3 ), gallium sulfide (Ga 2 S 3 ), gallium selenide (GaSe, Ga 2 Se 3 ) Gallium telluride (GaTe, Ga 2 Te 3 ), indium oxide (In 2 O 3) , indium sulfide (In 2 S 3 , InS), indium selenide (In 2 Se 3 ), indium telluride (In 2 Te 3 compounds of Group III elements of the periodic table and Group VI elements of the periodic table, such as 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); compounds of Group II elements of the periodic table and Group VI elements of the periodic table, such as copper(I) oxide (Cu 2compounds of Group I elements of the periodic table and Group VI elements of the periodic table, such as copper(I) chloride (CuCl), copper(I) bromide (CuBr), copper(I) iodide (CuI), silver chloride (AgCl), silver bromide (AgBr), compounds of Group I elements of the periodic table and Group VII elements of the periodic table, such as AgInS 2 , CuInS 2 I-III-VI etc. 2 Examples of suitable semiconductors include group III-V chalcopalite-type compound semiconductors, and 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 case of group III-V semiconductors, alloys such as InGaP and InGaN may be used. Semiconductor particles doped with rare earth elements or transition metal elements may also be used. For example, ZnS:Mn, ZnS:Tb, ZnS:Ce, LaPO 4 : Ce, etc.

[0015] Among these, 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, Ga 2 Se 3 ), indium sulfide (In 2 S 3 , 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, InGaN, and other alloy systems 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): AQX 3[In formula (I), A is methylammonium (CH 3 NH 2 ) and formamidinium (NH 2 Q is a monovalent cation of at least one amine compound selected from the group consisting of ammonium nitrate, ...

[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 material forming the core. 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 non-radiative transitions at the particle surface is reduced, improving the quantum yield of light emission and the stability of fluorescent 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 shells 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. In quantum dots, since the semiconductor particles 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. In transmission electron microscope images, the semiconductor particle portion appears dark relative to the surface treatment agent due to differences in electron density, and this is utilized to measure the particle size of the semiconductor particles. 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 disclosure includes a compound represented by any one of the above general formulas (1) to (6).

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

[0022] In general formula (1), X 1 ~X 6 are each independently C-R 1 -R 2 , or N, and X 1 ~X 6 At least one of them is N, and X 1 ~X 6 Among them, C-R 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, it is preferable that N is one. 1 ~X 6 Among these, it is preferable that N is two or more.

[0023] R 1 each independently represents a direct bond, —O—, —CO—, —COO—, or —SO 2 - is. 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. 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 residue is a residue of carbazole, benzofurocarbazole, thienocarbazole, indolocarbazole, bicarbazole, or phenazine" also includes cases where these compounds have a substituent, and the substituent has the same meaning as the substituent in the present disclosure (the same applies to general formulas (2) to (6) described later).

[0024] Here, 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 a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, a dodecyl group, a pentadecyl group, and an octadecyl group.

[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, condensed-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] 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, R2 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 2 The monovalent aliphatic hydrocarbon group, monovalent aromatic hydrocarbon group, and 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. 2 The amino group may further have a substituent, and in this case, the substituent may be 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, see the above-mentioned section R 2 The explanations for the monovalent aliphatic hydrocarbon group, the monovalent aromatic hydrocarbon group, and the monovalent aromatic heterocyclic group can be applied.

[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 6From the viewpoints of the stability of the ink composition and the luminous efficiency and durability of the electroluminescent device, it is preferable that X 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 X 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 X has at least one unsubstituted amino group. 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.

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

[0038] The general formula (2) is 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 C-R 1 -R 2 , or N, and X 7 ~X 14 At least one of them is N, and X 7 ~X 14 Among them, C-R 1 -R 2 is equal to or greater than the number N.

[0040] R 1 each independently represents a direct bond, —O—, —CO—, —COO—, or —SO 2 - is. 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. 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, the substituted or unsubstituted monovalent aromatic hydrocarbon group, and the substituted or unsubstituted monovalent aromatic heterocyclic group.

[0042] X 7 ~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 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.

[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 general formula (8) or (9) are preferred from the viewpoint of long-term dispersion stability.

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

[0046] In general formula (3), X 15 ~X 18 are each independently C-R 1 -R 2 , or N, and X 15 ~X 18 At least one of them is N, and X 15 ~X 18 Among them, C-R 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 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. 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 18At least one of X has a carboxy group, a sulfonic acid group, a phosphonic acid group, or an unsubstituted amino group. 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.

[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 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 includes R 2 The explanation about this can be used.

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

[0055] In general formula (4), X 19 ~X 24 are each independently C-R 1 -R2 , or N, and X 19 ~X 24 At least one of them is N, and X 19 ~X 24 Among them, C-R 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 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. 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 When one of X has an unsubstituted amino group, 19 ~X 24 The number of unsubstituted amino groups contained in X is 1, and19 ~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 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 includes R 2 The explanation about this can be used.

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

[0064] In general formula (5), X 25 ~X 30 are each independently C-R 1 -R 2 , or N, and X 25 ~X 30 At least one of them is N, and X 25 ~X 30 Among them, C-R 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 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. 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 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.

[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 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 includes 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 formulas (1) to (5).

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

[0074] R 1 each independently represents a direct bond, —O—, —CO—, —COO—, or —SO 2 - is. 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. 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 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.

[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 in order to prevent a decrease in brightness during long-term operation. Examples of the electron-withdrawing group include a halogen atom, a perfluoroalkyl group, a cyano group, and R 1 is -CO-, -COO-, or -SO 2 -R when - 1 -R 2 A perfluoroalkyl group is one in which all hydrogen atoms in an alkyl chain are replaced with fluorine atoms, and is represented by -(CF 2 ) n -CF 3 (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. Particularly preferred electron-withdrawing groups are a fluorine atom, a trifluoromethyl group, and a cyano group.

[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 contained in the compounds of general formulas (1) to (6) 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 shown 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 ink composition containing the quantum dots of the present disclosure contains the above-described quantum dots and a dispersion medium. The dispersion medium is used to disperse the quantum dots and to facilitate application of the quantum dots of the present disclosure to 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, 3-methoxy-3-methylbutyl ether ... 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 dispersing 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 dispersing mediums 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 disclosure may be adjusted using a dispersion medium, a resin, a polymerizable monomer, etc. When the ink composition of the present disclosure 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 disclosure can be used as an emitting layer in an electroluminescent device. The electroluminescent device has a substrate, a cathode and an anode provided on the substrate, and a emitting layer between the two electrodes. Furthermore, due to the nature of the light-emitting device, at least one of the anode and 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. (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, (11) anode / hole injection layer / hole transport layer / interlayer layer / light-emitting layer / electron injection layer / cathode, and the like are conceivable.

[0088] The substrate for forming the electroluminescent element can be, for example, a substrate used in known organic EL elements. The substrate may be a resin film or a gas barrier film, and gas barrier films described in JP-A Nos. 2004-136466, 2004-148566, 2005-246716, and 2005-262529 are also preferably used. The thickness of the substrate is not particularly specified, but is preferably 30 μm to 700 μm, more preferably 40 μm to 200 μm, and even more preferably 50 μm to 150 μm. Furthermore, 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 is generally sufficient as long as it functions as an electrode that supplies holes to an organic compound 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 described above, the anode is generally 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 that injects electrons into an organic compound 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. Examples of materials constituting the cathode include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Specific examples include Group 2 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. These materials may be used alone, but from the viewpoint of achieving both stability and electron injection properties, two or more types can be suitably used in combination.

[0091] Among these, materials primarily composed of aluminum are preferred as materials for constituting the cathode. Materials primarily 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 alloys, magnesium-aluminum alloys, etc.). Cathode materials are described in detail in JP-A-2-15595 and JP-A-5-121172. Furthermore, 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 forming 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 disclosure, 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, for example, a mixture of an electron-transporting host material and a hole-transporting host material. Furthermore, the light-emitting layer may contain a material that does not have charge transport properties and does not emit light. The light-emitting layer may also be a single 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 having the function of receiving electrons from the cathode or the cathode side and transporting them to the anode side. Specific examples of the electron injection layer and the electron transport layer include 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, metal complexes of 8-quinolinol derivatives, metal phthalocyanines, various metal complexes typified by metal complexes having benzoxazole or benzothiazole as a ligand, low molecular weight compounds such as organic silane derivatives, zinc oxide (ZnO), titanium oxide (TiO 2 The layer is preferably a layer containing a metal oxide such as zinc oxide, or an organic or inorganic compound doped with an alkali metal, and particularly preferably zinc oxide doped with magnesium, ZnMgO.

[0100] <Hole Blocking Layer> The hole blocking layer is a layer that 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 disclosure, a hole blocking layer can be provided as an organic compound layer adjacent to the light-emitting layer on the cathode side. The electron transport layer and / or the electron injection layer may also function as the hole blocking layer. Examples of organic compounds that constitute the hole blocking layer include aluminum complexes such as BAlq, triazole derivatives, and phenanthroline derivatives such as BCP. A layer that has the function of preventing electrons transported from the cathode side to the light-emitting layer from passing through to the anode side can also be provided adjacent to the light-emitting layer on the anode side. The hole transport layer and / or the hole injection layer may also have this function.

[0101] The present disclosure will be described in more detail below with reference to examples, but the following examples do not limit the technical scope of the present disclosure in any way. 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] 0.55 parts of anhydrous zinc acetate, 7.0 parts of dodecanethiol (treatment agent R1), and 5.0 parts of oleylamine were heated and dissolved to prepare an additive solution. Separately, 0.22 parts of indium chloride and 8.25 parts of octylamine were placed in a reaction vessel, and the mixture was 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 maintained at 165 ° C. for 20 minutes. The mixture was then cooled to a liquid temperature of 40 ° C. Next, the additive solution was added to the reaction vessel, heated at 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, in which core-shell semiconductor particles having an InP core and a ZnS shell were surface-treated with dodecanethiol.

[0103] Synthesis Example 2: 2.0 mL of oleic acid and 10 mL of 1-octadecene were added to a 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. Furthermore, 0.3 mmol of diethylzinc solution was 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, dissolved by heating at 100°C, and degassed under vacuum for 1 hour with stirring to prepare 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 were synthesized, and the reaction solution was stirred for 30 minutes. Next, 4.0 mL of trioctylphosphine was added to 0.16 g (5.0 mmol) of sulfur, and the mixture was heated to 150 ° C and dissolved to prepare a 1.25 M sulfur / trioctylphosphine solution. 1.0 mL was added to the reaction solution and stirred for 1 hour. Next, 0.22 g (1.1 mmol) of zinc acetate was added to the reaction solution, and the mixture was dissolved by heating and stirring at 100 ° C under reduced pressure. The flask was again purged with nitrogen and heated to 230 ° C, and 0.48 mL (2 mmol) of dodecanethiol was added and 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 quantum dots EX2, which are core-shell type semiconductor particles having a core of ZnTeSe and a shell consisting of two layers of ZnSe / ZnS, and which are surface-treated with dodecanethiol.

[0104] Synthesis Example 3: 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 were added to a 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 200°C and maintained for 20 minutes. Subsequently, the flask was 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, and the mixture was heated and stirred 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 AgInS 2 Thus, quantum dots EX3 were obtained in which core-shell type semiconductor particles with a shell of ZnS were surface-treated with dodecanethiol.

[0105] Example 1 (Quantum Dots and Ink Composition) 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 shown in 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%, yielding ink composition 1 containing 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 axis diameter and major axis diameter of the semiconductor particles were measured, and the average value of the minor axis diameter and major axis diameter was taken as the particle size of the semiconductor particles. The average particle size of 30 randomly selected semiconductor particles was calculated, and this was taken as 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 treatment agent were obtained in the same manner as in Example 1, except that treatment agent 1 was changed to treatment agents 2 to 414 and treatment agents R1 to R3 shown in Tables 1 to 61. Ink compositions 2 to 414 are ink compositions of the present disclosure, and ink compositions R1 to R3 are comparative ink compositions that are not ink compositions of the present disclosure.

[0107] Example 415 Ink composition 415 containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 5 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.

[0108] Example 416 Ink composition 416 containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 110 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 in Table 11.

[0109] Example 417 Ink composition 417 containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 178 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.

[0110] Example 418 Ink composition 418 containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 215 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 in Table 24.

[0111] Example 419 Ink composition 419 containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 269 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 in Table 35.

[0112] Example 420 Ink composition 420 containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 329 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.

[0113] Example 421 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treating agent 1 was replaced with treating agent 28 in Table 3. The same procedure as in Example 1 was repeated to obtain quantum dots having a core of AgInS. 2 Thus, an ink composition 421 containing quantum dots in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 28 was obtained.

[0114] Example 422 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with treatment agent 147 in Table 15. The same procedure as in Example 1 was repeated to obtain quantum dots having a core of AgInS. 2 Thus, an ink composition 422 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 147.

[0115] Example 423 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 166 in Table 20, and the same procedure as in Example 1 was repeated to obtain quantum dots having a core of AgInS. 2 Thus, an ink composition 423 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 166.

[0116] Example 424 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 216 in Table 25. The same procedure as in Example 1 was repeated to obtain quantum dots having a core of AgInS. 2 Thus, an ink composition 424 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with the treating agent 216.

[0117] Example 425 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with treatment agent 273 in Table 36. The same procedure as in Example 1 was repeated to obtain quantum dots with a core of AgInS. 2 Thus, ink composition 425 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 273.

[0118] Example 426 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with treatment agent 364 in Table 51, and the same procedure as in Example 1 was repeated to obtain quantum dots having a core of AgInS. 2 Thus, an ink composition 426 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with the treating 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 containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 418, 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 in Table 62.

[0121] Example 664 Ink composition 664 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 419, 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.

[0122] Example 665 Ink composition 665 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 420, 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 in Table 62.

[0123] Example 666 Ink composition 666 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a two-layer ZnSe / ZnS shell were surface-treated with treatment agent 477, 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 477 in Table 72.

[0124] Example 667 Ink composition 667 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a two-layer ZnSe / ZnS shell were surface-treated with treatment agent 478, 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 478 in Table 72.

[0125] Example 668 Ink composition 668 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 479, 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 479 in Table 72.

[0126] Example 669 Ink composition 669 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 522, 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 in Table 79.

[0127] Example 670 Ink composition 670 containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 523 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 in Table 79.

[0128] Example 671 Ink composition 671 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a two-layer ZnSe / ZnS shell were surface-treated with treatment agent 524, 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.

[0129] Example 672 Ink composition 672 containing quantum dots in which core-shell type semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / 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 EX2 obtained in Synthesis example 2 and treatment agent 1 was replaced with treatment agent 555 in Table 84.

[0130] Example 673 Ink composition 673 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a two-layer ZnSe / ZnS shell were surface-treated with treatment agent 553, 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 in Table 84.

[0131] Example 674 Ink composition 674 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a two-layer ZnSe / ZnS shell were surface-treated with treatment agent 554, 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.

[0132] Example 675 Ink composition 675 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 588, 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 588 in Table 89.

[0133] Example 676 Ink composition 676 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 591, 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 589 in Table 89.

[0134] Example 677 Ink composition 677 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 590, 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 590 in Table 89.

[0135] Example 678 Ink composition 678 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 622, 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.

[0136] Example 679 Ink composition 679 was obtained containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a two-layer ZnSe / ZnS shell were surface-treated with treatment agent 623, 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 in Table 95.

[0137] Example 680 Ink composition 680 containing quantum dots in which core-shell semiconductor particles having a core of ZnTeSe and a shell of two layers of ZnSe / ZnS were surface-treated with treatment agent 624 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 624 in Table 96.

[0138] Example 681 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 418 shown in Table 62. 2 Thus, an ink composition 681 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with the treating agent 418.

[0139] Example 682 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with treatment agent 419 shown in Table 62. The same procedure as in Example 1 was repeated to obtain quantum dots with AgInS cores. 2 Thus, ink composition 682 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 419.

[0140] Example 683 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 420 shown in Table 62. 2 Thus, an ink composition 683 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 420.

[0141] Example 684 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with treatment agent 477 shown in Table 72. The same procedure as in Example 1 was repeated to obtain quantum dots with AgInS cores. 2 Ink composition 684 was obtained, which contained quantum dots in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 477.

[0142] Example 685 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with treatment agent 478 shown in Table 72. The same procedure as in Example 1 was repeated to obtain quantum dots with AgInS cores. 2 Thus, ink composition 685 containing quantum dots in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 478 was obtained.

[0143] Example 686 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with treatment agent 479 shown in Table 72. The same procedure as in Example 1 was repeated to obtain quantum dots with AgInS cores. 2 Thus, ink composition 686 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 479.

[0144] Example 687 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 522 in Table 79. The same procedure as in Example 1 was repeated to obtain quantum dots with AgInS cores. 2 Thus, ink composition 687 containing quantum dots in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 522 was obtained.

[0145] Example 688 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 523 shown in Table 79. 2 Thus, ink composition 688 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 523.

[0146] Example 689 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 524 in Table 79. The same procedure as in Example 1 was repeated to obtain quantum dots having a core of AgInS. 2 Thus, ink composition 689 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 524.

[0147] Example 690 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 555 shown in Table 84. 2 Thus, ink composition 690 containing quantum dots in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 555 was obtained.

[0148] Example 691 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 553 shown in Table 84. 2 Ink composition 691 containing quantum dots in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 553 was obtained.

[0149] Example 692 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 554 shown in Table 84. 2 Thus, an ink composition 692 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with the treating agent 554.

[0150] Example 693 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 588 shown in Table 89. 2 Thus, ink composition 693 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with treating agent 588.

[0151] Example 694 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with treatment agent 589 shown in Table 89. 2 Ink composition 694 was obtained, which contained quantum dots in which core-shell type semiconductor particles with a shell of ZnS were surface-treated with treating agent 589.

[0152] Example 695 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 590 shown in Table 89. 2 Thus, an ink composition 695 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with the treating agent 590.

[0153] Example 696 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 622 shown in Table 95. The same procedure as in Example 1 was repeated to obtain a quantum dot having a core of AgInS. 2 Thus, an ink composition 696 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with the treating agent 622.

[0154] Example 697 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 623 shown in Table 95. The same procedure as in Example 1 was repeated to obtain a quantum dot having an AgInS core. 2 Thus, an ink composition 697 containing quantum dots was obtained in which core-shell type semiconductor particles having a shell of ZnS were surface-treated with the treating agent 623.

[0155] Example 698 The quantum dots EX1 obtained in Synthesis Example 1 were replaced with the quantum dots EX3 obtained in Synthesis Example 3, and the treatment agent 1 was replaced with the treatment agent 624 shown in Table 96. The same procedure as in Example 1 was repeated to obtain a quantum dot having an AgInS core. 2Ink composition 698 was obtained, which contained quantum dots in which core-shell semiconductor particles having a core of InP and a shell of ZnS were surface-treated with treating agent 624. [Examples 699 to 972] Ink compositions 699 to 972 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, which contained quantum dots in which core-shell semiconductor particles having a core of InP and a shell of ZnS were surface-treated with a treating agent.

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[0298] (Evaluation of Ink Stability) 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, taken as 1.0, was used to evaluate the ink stability. The results are shown in Tables 143 to 167. The criteria are 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 inks 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 presence or absence of turbidity or precipitation was confirmed visually. The results are shown in Tables 143 to 167. A: No turbidity was observed. B: Slight turbidity was observed. C: Turbidity and precipitation were also observed. D: Aggregation and precipitation occurred.

[0300] (Comparison of electroluminescent device properties produced with inks before and after evaluation of long-term dispersion stability) For 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 properties were compared. The electroluminescent device performance was evaluated by the following method. Vapor deposition (vacuum vapor deposition) was performed for 10 -6 The measurement 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 element were measured using an electroluminescent element having a light emitting element area of ​​2 mm x 2 mm.

[0301] An ethanol dispersion of molybdenum oxide nanoparticles (concentration: 2.3 to 2.7% by mass) purchased from Sigma-Aldrich was applied to a cleaned glass plate equipped with an ITO electrode by spin coating, followed by drying at 150°C for 20 minutes to obtain a hole injection layer with a thickness of 20 nm. Next, poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] was dissolved in monochlorobenzene at a concentration of 1.0% by mass, applied by spin coating, 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 disclosure obtained in the Examples and Comparative Examples were diluted 20-fold with mesitylene, applied by spin coating, and then dried for 5 minutes in a nitrogen atmosphere at 25°C to form a 25-nm light-emitting layer. An isopropanol dispersion of zinc oxide nanoparticles N-10 manufactured by 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, thereby obtaining an electroluminescent device. The obtained device was subjected to a current density test 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 produced with the ink before the long-term dispersion stability evaluation was divided by the luminous efficiency of the element produced with the ink after the long-term dispersion stability evaluation was calculated. 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, making it impossible to produce an element, 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. A film was formed by spin-coating the ink composition on a glass substrate that had been cleaned with an electronics industry detergent and solvent and then treated with UV ozone, followed by heat treatment on a hot plate at 80°C. The arithmetic mean roughness (Ra) (nm) of the formed film was determined according to the method specified in Japanese Industrial Standards (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, 5.0 or less; C: More than 5.0, 10.0 or less; D: More than 10.0.

[0303] (Evaluation of electroluminescent devices) The electroluminescent device performance of 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 experiments were carried out in a vacuum of 1000 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] An ethanol dispersion of molybdenum oxide nanoparticles (concentration: 2.3 to 2.7% by mass) purchased from Sigma-Aldrich was applied to a cleaned glass plate equipped with an ITO electrode by spin coating, followed by drying at 150°C for 20 minutes to obtain a hole injection layer with a thickness of 20 nm. Next, poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] was dissolved in monochlorobenzene at a concentration of 1.0% by mass, applied by spin coating, 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 disclosure obtained in the Examples and Comparative Examples were diluted 20-fold with mesitylene, applied by spin coating, and then dried for 5 minutes in a nitrogen atmosphere at 25°C to form a 25-nm light-emitting layer. An isopropanol dispersion of zinc oxide nanoparticles N-10 manufactured by 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, thereby obtaining an electroluminescent device. The obtained device was subjected to a current density test 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 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 luminance after 100 hours of continuous operation are as follows:

[0305] Luminous efficiency (cd / A) A+: 5.5 or more. 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 more. 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]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332] This application claims priority based on Japanese Patent Application No. 2024-133864 filed on August 9, 2024, and Japanese Patent Application No. 2024-164755 filed on September 24, 2024, the disclosures of which are incorporated herein in their entireties.

Claims

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): [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 the groups is N, and X 1 ~X 6 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. 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. 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 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.] [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 the groups is N, and 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. 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. 7 ~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 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) does not include the case where it is represented by general formula (1). [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 the groups is N, and X 15 ~X 18 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. 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. 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 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. 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). [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 the groups is N, and X 19 ~X 24 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. 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. 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 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. 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). [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 the groups is N, and X 25 ~X 30 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. 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. 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 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. 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). [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 the groups is N, and X 31 ~X 37 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. 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. 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 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) does not include the 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 contains a compound represented by any one of the following general formulas (7) to (9): [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. 23 is a hydrogen atom, a halogen atom, a cyano group, or a substituted amino group, R 22 is a direct bond.] [In general formula (8), R 8 ~R 14 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. 23 is a hydrogen atom, a halogen atom, a cyano group, or a substituted amino group, R 22 is a direct bond.] [In general formula (9), R 15 ~R 21 and each independently represent -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. 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. 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 or 2.

Citation Information

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