Quantum dot-containing material, and composition and electronic device including the same

Abstract

A quantum dot-containing material comprising: a quantum dot; and one or more ligands chemically bonded to the surface of the quantum dot and represented by a predetermined chemical formula; a composition comprising the same and an electronic device are disclosed.

Description

Technology Field

[0001] This invention relates to a quantum dot-containing material, a composition containing the same, and an electronic device. Background Technology

[0002] Quantum dots are nanocrystals of semiconductor materials that exhibit a quantum confinement effect. When a quantum dot receives light from an excitation source and reaches an energy-excited state, it emits energy corresponding to its own energy band gap. At this time, since the wavelength varies depending on the particle size even for the same material, light in a desired wavelength range can be obtained by controlling the size of the quantum dot. Because it can exhibit characteristics such as excellent color purity and high luminous efficiency, it can be applied to various devices.

[0003] In addition, quantum dots can be utilized as materials that perform various optical functions (e.g., photoconversion functions) among optical components. Quantum dots are nanoscale semiconductor nanocrystals, and by controlling the size and composition of the nanocrystals, they can have different energy bandgaps and, accordingly, emit light of various emission wavelengths.

[0004] Optical components containing such quantum dots can have a thin film form, for example, a thin film patterned for each subpixel. Such optical components can also be utilized as color conversion components for devices containing various light sources. The problem to be solved

[0005] The present invention provides a quantum dot-containing material with improved stability by introducing an initiator moiety to a ligand chemically bonded to the surface of the quantum dot, a composition with improved quantum yield by employing the same, and an electronic device. means of solving the problem

[0006] According to one aspect, a quantum dot is provided; and a quantum dot-containing material comprising one or more ligands chemically bonded to the surface of the quantum dot and represented by the following chemical formula 1:

[0007] <Chemical Formula 1>

[0008] R a -(Z1) a1 -(L1) b1 -(Z2) a2 -P1

[0009] <Chemical Formula 2-1>

[0010] -N=N-(Z3) a3 -R1

[0011] <Chemical Formula 2-2>

[0012]

[0013] Among the above chemical formulas 1 and 2-1 to 2-2,

[0014] R a is an anchoring group containing a moiety represented by -COOH, -PO3H, a dithiolane group, or -SH, and

[0015] L1 is *-(CH2) n1 -*', or *-(O-CH2-CH2) n1 -O-*' and,

[0016] b1 is selected from integers 1 to 5, and

[0017] P1 is a group represented by the above chemical formula 2-1 or 2-2, and

[0018] Z1 to Z3 are independently of each other, *-O-*', *-C(=O)-*', *-C(=O)O-*', *-OC(=O)-*', *-OC(=O)-O-*', *-OCH2-*', *-SCH2-*', *-CH2S-*', *-CF2O-*', *-OCF2-*', *-CF2S-*', *-SCF2-*', *-(CH2) n1-*', *-CF2CH2-*', *-CH2CF2-*', *-(CF2) n1 -*', *-C(CH3)CN-*', *-CH=CH-*', *-CF=CF-*', *-C≡C-*', *-CH=CH-C(=O)O-*', *-OC(=O)-CH=CH-*', *-C(Q1)(Q2)-*', and *-O-(CH2)-O(C=O)-(CH2) n2 Selected from -*',

[0019] n1 is selected from integers 1 to 6, and n2 is selected from integers 0 to 2, and

[0020] a1 to a3 are independently selected from integers 0 to 6, and

[0021] R1 is *-(CH2) n3 -CH3, or *-(O-CH2-CH2) n1 -OH and,

[0022] n3 is selected from integers 0 to 5, and

[0023] The above Q1 and Q2 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazino group, hydrazono group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C1-C 60 Selected from heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic heterocondensed polycyclic groups, biphenyl groups and terphenyl groups, and

[0024] * and *' are bonding sites with neighboring atoms.

[0025] According to another aspect, the above quantum dot-containing material; and

[0026] A composition comprising one or more solvents is provided.

[0027] According to another aspect, an electronic device including the above quantum dot-containing material is provided.

[0028] According to one embodiment, the electronic device further comprises a light-emitting element including a first electrode; a second electrode facing the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode, and the quantum dot-containing material may be included in the light-emitting layer.

[0029] According to another embodiment, the electronic device further includes a light source, and the quantum dot-containing material may be placed in the path of light emitted from the light source.

[0030] For example, the above quantum dot-containing material may be included in the color conversion layer.

[0031] For example, the light source may be an organic light-emitting diode (OLED) or a light-emitting diode (LED). Effects of the invention

[0032] The present invention simplifies the process by introducing an initiator moiety into a ligand chemically bonded to the surface of a quantum dot, and allows the ligand to bind to the quantum dot surface without the need to consider miscibility between the initiator and the solvent, thereby inducing polymer growth on the quantum dot surface and protecting the quantum dot from radical attacks that degrade its efficiency. Through this, the quantum yield of the generated thin film and composition can be improved. Brief explanation of the drawing

[0033] Figure 1 is a schematic diagram showing the structure of a quantum dot-containing material according to one embodiment. FIG. 2 is a schematic diagram showing the structure of a light-emitting element included in an electronic device according to one embodiment of the present invention. FIGS. 3 and 4 are cross-sectional views schematically illustrating a light-emitting device according to one embodiment of the present invention. Figures 5a and 5b are graphs showing the change in PCE (%) before and after baking of thin films formed by quantum dot-containing materials according to Comparative Example 1 and Example 1, respectively. Figures 6a and 6b are graphs showing the change in PCE (%) before and after exposure of thin films formed by quantum dot-containing materials according to Comparative Example 1 and Example 2, respectively. Specific details for implementing the invention

[0034] The present invention is capable of various modifications and may have various embodiments; specific embodiments are illustrated in the drawings and described in detail in the detailed description. The effects and features of the present invention, and the methods for achieving them, will become clear by referring to the embodiments described below in detail together with the drawings. However, the present invention is not limited to the embodiments disclosed below but can be implemented in various forms.

[0035] Hereinafter, embodiments of the present invention will be described in detail with reference to the attached drawings. When describing with reference to the drawings, identical or corresponding components are given the same reference numerals, and redundant descriptions thereof will be omitted.

[0036] In the following embodiments, terms such as first, second, etc. are used not in a limiting sense, but for the purpose of distinguishing one component from another component.

[0037] In the following examples, singular expressions include plural expressions unless the context clearly indicates otherwise.

[0038] In the following embodiments, terms such as "include" or "have" mean that the features or components described in the specification are present, and do not preclude the possibility that one or more other features or components may be added.

[0039] In the following embodiments, when various components such as layers, films, regions, and plates are described as being "on" another component, this includes not only cases where they are "directly on" another component, but also cases where other components are interposed between them. Furthermore, for convenience of explanation, the size of components in the drawings may be exaggerated or reduced. For example, the size and thickness of each component shown in the drawings are depicted arbitrarily for convenience of explanation, and therefore the present invention is not necessarily limited to what is illustrated.

[0040] [Quantum dot-containing material]

[0041] FIG. 1 is a schematic diagram showing the structure of a quantum dot-containing material according to one embodiment of the present invention.

[0042] Referring to FIG. 1, the quantum dot-containing material (1) comprises: a quantum dot (2); and one or more ligands (3) chemically bonded to the surface of the quantum dot (2) and represented by the following chemical formula 1:

[0043] <Chemical Formula 1>

[0044] R a -(Z1) a1 -(L1) b1 -(Z2) a2 -P1

[0045] Among the above chemical formula 1,

[0046] R a is an anchoring group (4) containing a moiety represented by -COOH, -PO3H, dithiolane group, or -SH.

[0047] Here, the anchoring group (4) is a coupling group that causes the ligand (3) to be adsorbed onto the quantum dot (2) when the ligand (3) binds to the quantum dot (2).

[0048] According to one embodiment, the above R a-COOH, -PO3H, -SH, or can be selected from the group represented by the following chemical formulas 3-1 to 3-4:

[0049]

[0050] Among the above chemical formulas 3-1 to 3-4,

[0051] * is a bonding site with a neighboring atom.

[0052] For example, the above R a It can be -SH.

[0053] In the above chemical formula 1, L1 is *-(CH2) n1 -*', or *-(O-CH2-CH2) n1 -O-*' is.

[0054] The above L1 is *-(CH2) n1 In the case of -*', the polarity of the quantum dot-containing material may be reduced, and the above L1 is *-(O-CH2-CH2) n1 In the case of -O-*', the polarity of the quantum dot-containing material may increase.

[0055] In the above chemical formula 1, b1 is selected from integers 1 to 5.

[0056] The above b1 is the number of L1s, and if b1 is 2 or more, the 2 or more L1s may be the same or different.

[0057] In the above chemical formula 1, P1 is a group represented by the following chemical formula 2-1 or 2-2.

[0058] <Chemical Formula 2-1>

[0059] -N=N-(Z3) a3 -R1

[0060] <Chemical Formula 2-2>

[0061]

[0062] The above P1 is a group that can be decomposed by exposure (hv) or heat to form radicals.

[0063] For example, the group represented by the above chemical formula 2-1 can be decomposed by heat to form two radicals while releasing N2.

[0064] For example, the group represented by the above chemical formula 2-2 can be decomposed by exposure (hv) to form radicals through the following mechanism.

[0065]

[0066] Among the above chemical formulas 1 and 2-1 to 2-2,

[0067] Z1 to Z3 are independently of each other, *-O-*', *-C(=O)-*', *-C(=O)O-*', *-OC(=O)-*', *-OC(=O)-O-*', *-OCH2-*', *-SCH2-*', *-CH2S-*', *-CF2O-*', *-OCF2-*', *-CF2S-*', *-SCF2-*', *-(CH2) n1 -*', *-CF2CH2-*', *-CH2CF2-*', *-(CF2) n1 -*', *-C(CH3)CN-*', *-CH=CH-*', *-CF=CF-*', *-C≡C-*', *-CH=CH-C(=O)O-*', *-OC(=O)-CH=CH-*', *-C(Q1)(Q2)-*', and *-O-(CH2)-O(C=O)-(CH2) n2 Selected from -*'.

[0068] According to one embodiment, the above Z1 is *-(CH2) n1 -*'It could be.

[0069] According to one embodiment, Z2 and Z3 are independently of each other, *-O-*', *-C(=O)O-*', *-OC(=O)-*', *-(CH2) n1 It can be -*', or *-C(CH3)CN-*'.

[0070] For example, the above *-(Z2) a2 -*' and *-(Z3) a3-*' can be independently selected from the groups represented by the following chemical formulas 4-1 to 4-4:

[0071]

[0072] Among the above chemical formulas 4-1 to 4-4,

[0073] * and *' are bonding sites with neighboring atoms.

[0074] Among the above chemical formulas 1 and 2-1 to 2-2, n1 is selected from integers 1 to 6, and n2 is selected from integers 0 to 2, and

[0075] a1 to a3 are independently selected from integers 0 to 6.

[0076] The above a1 to a3 are each the number of Z1 to Z3, and if a1 is 2 or more, 2 or more Z1s may be the same or different, if a2 is 2 or more, 2 or more Z2s may be the same or different, if a3 is 2 or more, 2 or more Z3s may be the same or different, and if a1 is 0, -(Z1) a1 - is a single bond, and if a2 is 0, -(Z2) a2 - is a single bond, and if a3 is 0, -(Z3) a3 - is a single combination.

[0077] In the above chemical formula 2-1, R1 is *-(CH2) n3 -CH3, or *-(O-CH2-CH2) n1 -OH, and n3 is selected from integers from 0 to 5.

[0078] The above R1 is *-(CH2) n3 In the case of -CH3, the polarity of the quantum dot-containing material may be reduced, and the above R1 is *-(O-CH2-CH2) n1 In the case of -OH, the polarity of the quantum dot-containing material may increase.

[0079] In the above chemical formulas 1 and 2-1 to 2-2, Q1 and Q2 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazino group, hydrazono group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C1-C 60 Selected from heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic heterocondensed polycyclic groups, biphenyl groups and terphenyl groups, and * and *' are bonding sites with neighboring atoms.

[0080] In the above chemical formula 1, d1 is selected from integers from 0 to 4.

[0081] According to one embodiment, the ligand (3) may be represented by the following chemical formula 1A or 1B:

[0082] <Chemical Formula 1A>

[0083]

[0084] <Chemical Formula 1B>

[0085]

[0086] Among the above chemical formulas 1A and 1B,

[0087] R a For a description of , L1, b1 and R1, refer to the above.

[0088] According to one embodiment, the ligand (3) is two or more, and the two or more ligands (3) may be identical or different from each other.

[0089] For example, the ligand (3) can be chemically bonded to the surface of the quantum dot (2) through an anchoring group (4).

[0090] According to one embodiment, the quantum dot (2) may be a semiconductor nanoparticle, a core-shell structure particle including a core including a first semiconductor crystal and a shell including a second semiconductor crystal, or a perovskite compound.

[0091] For example, the quantum dots (2) may be semiconductor nanoparticles or core-shell structured particles.

[0092] For example, the semiconductor nanoparticles, the first semiconductor, and the second semiconductor may independently include a group 10 compound, a group 11 compound, a group 12-16 compound, a group 13-15 compound, a group 14-16 compound, a group 14 compound, a group 11-13-16 compound, a group 11-12-13-16 compound, or any combination thereof.

[0093] For example, the semiconductor nanoparticles, the first semiconductor, and the second semiconductor are independent of each other.

[0094] Au, Pd, Ag;

[0095] CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgS, MgSe; CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe MgZnS, MgZnSe; CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe;

[0096] GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb; GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP; GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb; InZnP;

[0097] SnS, SnSe, SnTe, PbS, PbSe, PbTe; SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe; SnPbSSe, SnPbSeTe, SnPbSTe;

[0098] Si, Ge, SiC, SiGe;

[0099] AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2; or may include any combination thereof.

[0100] For example, the first semiconductor is CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgS, MgSe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnS, MgZnSe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, Comprising GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, or any combination thereof,

[0101] The second semiconductor may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgS, MgSe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnS, MgZnSe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, or any combination thereof.

[0102] According to one embodiment, the average particle size (D50) of the quantum dot (2) may be 2 to 10 nm.

[0103] The average particle size (D50) of the quantum dot-containing material (100) may be 40 nm to 1000 nm, for example, 50 nm to 1000 nm or 100 nm to 500 nm, or as another example, 100 nm to 200 nm. When the average particle size of the quantum dot-containing material (100) satisfies the range described above, the quantum dot-containing material (100) may have excellent dispersion while containing a relatively large amount of quantum dots (2).

[0104] Conventionally, to form thin films using compositions containing quantum dots, compositions containing an initiator, a radical scavenger, a reactive monomer, a dispersant, and ligand-substituted quantum dots were used. In the thin film formation process using such compositions, it was essential to consider the miscibility of the initiator and the solvent; if the dispersion state of the quantum dots and the initiator was non-uniform, non-uniformity of the pattern could occur during pattern formation using the thin film. Furthermore, the efficiency of the quantum dots could be reduced by free radicals.

[0105] The above quantum dot-containing material (1) can induce polymer growth on the surface of the quantum dot (2) by including a ligand (3) containing an initiator moiety, and at the same time, protect the quantum dot (2) from attack by free radicals.

[0106] In addition, by including the initiator moiety in the ligand (3), a separate scavenger or initiator is not required, which can reduce costs and simplify the process. Furthermore, since the quantum dots (2) and the initiator moiety are included in the same quantum dot-containing material (1), the quantum dots (2) and the initiator moiety can be uniformly dispersed. Through this, the efficiency of the quantum dot-containing material (2) can be maintained during the formation of the resulting composition and thin film, and the stability of the quantum dot-containing material (2) can be improved.

[0107] Meanwhile, the above perovskite compound is a material having a three-dimensional crystal structure related to the crystal structure of CaTiO3.

[0108] For example, the above perovskite can be represented by the following chemical formula 4:

[0109] <Chemical Formula 4>

[0110] [A][B m ][X]3

[0111] Among the above chemical formula 4

[0112] A is at least one monovalent organic-cation, a monovalent inorganic-cation, or any combination thereof, and

[0113] B is at least one type of divalent inorganic cation, and

[0114] m is a real number satisfying 0 < m ≤ 1, and

[0115] X is at least one type of monovalent anion.

[0116] [Composition]

[0117] According to another aspect, a composition comprising the above-described quantum dot-containing material; and one or more solvents is provided.

[0118] The content of the quantum dot-containing material in the above composition may be 0.1 weight% or more to 20 weight% or less based on the total weight of the composition, specifically 0.2 weight% or more to 10 weight% or less, but is not limited thereto. If the above range is satisfied, the composition is suitable for use in fabricating a light-emitting device having sufficient luminous efficiency by a solution process.

[0119] A light-emitting device containing the above quantum dot-containing material can provide sufficient improvement in luminous efficiency and / or lifespan due to improved film uniformity, improved charge injection balance, improved influence of quantum dot efficiency by the transport layer, and / or prevention of direct contact between the electron transport layer and the hole transport layer caused by quantum dot vacancies.

[0120] The type of the above solvent is not limited as long as it can adequately disperse the quantum dot-containing material.

[0121] For example, the solvent may be an organic solvent.

[0122] For example, the above solvent may include a solvent having a boiling point of 100°C or higher and 180°C or lower.

[0123] Specifically, the solvent may be selected from chlorine-based, ether-based, ester-based, ketone-based, aliphatic hydrocarbon-based, and aromatic hydrocarbon-based solvents, but is not limited thereto.

[0124] More specifically, the solvent is dichloromethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, cyclohexylbenzene; tetrahydrofuran, dioxane, anisole, 4-methylanisole, butylphenyl ether; toluene, xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene, trimethylbenzene, tetrahydronaphthalene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, dodecane, hexadecane, oxadecane; acetone, methyl ethyl ketone, cyclohexanone, acetophenone; It may include, but is not limited to, ethyl acetate, butyl acetate, methyl sorb acetate, ethyl sorb acetate, methyl benzoate, ethyl benzoate, butyl benzoate, 3-phenoxy benzoate, or any combination thereof.

[0125] The content of the solvent in the above composition may be 80% by weight or more to 99.9% by weight or less based on the total weight of the composition, specifically 90% by weight or more to 99.8% by weight or less, but is not limited thereto. If the above range is satisfied, the quantum dots can be appropriately dispersed in the ink composition and can have a solid content concentration suitable for a solution process.

[0126] According to one embodiment, the composition may further include a monomer comprising one or more double bonds.

[0127] The above monomer may be an acrylic monomer or a styrene monomer.

[0128] For example, the monomer may be methyl methacrylate, styrene, methacrylic acid, or any combination thereof.

[0129] As described above, the quantum dot-containing material of the present invention has a ligand containing an initiator moiety bound, i.e., anchored to the surface of the quantum dot, and accordingly, radicals can be formed on the surface of the quantum dot by exposure (hv) or heating.

[0130] Through the radicals formed in this way, the monomer is polymerized, thereby inducing polymer growth on the surface of the quantum dot.

[0131] For example, the above composition may not include an initiator.

[0132] For example, the above composition may not include a scavenger.

[0133] The above composition may further include a hole-transporting compound or an electron-transporting compound.

[0134] For a description of the hole-transporting compound mentioned above, refer to the description of the compound included in the hole-transporting region described below.

[0135] Refer to the description of the above electron transportable compound for the description of the compounds included in the electron transport region described below.

[0136] The content of the hole transport compound or the electron transport compound in the above composition may be 0.5 weight% or more to 20 weight% or less based on the total weight of the composition, specifically 0.5 weight% or more to 15 weight% or less, but is not limited thereto.

[0137] The viscosity of the above composition may be 1 cP to 10 cP. A composition satisfying the above viscosity range may be suitable for manufacturing a quantum dot-containing layer of a light-emitting device by a solution process.

[0138] The surface tension of the above composition may be 10 dynes / cm to 40 dynes / cm. A composition satisfying the above surface tension range may be suitable for manufacturing a quantum dot-containing layer of a light-emitting device by a solution process.

[0139] [Light-emitting element]

[0140] FIG. 2 schematically illustrates a cross-sectional view of a light-emitting element (10) included in an electronic device according to one embodiment of the present invention. The light-emitting element (10) includes a first electrode (110), an intermediate layer (130), and a second electrode (150).

[0141] Hereinafter, the structure and manufacturing method of a light-emitting element (10) according to one embodiment of the present invention will be described with reference to FIG. 2.

[0142] [First electrode (110)]

[0143] A substrate may be additionally disposed on the lower part of the first electrode (110) of FIG. 2 or on the upper part of the second electrode (150). As the substrate, a glass substrate or a plastic substrate may be used. Alternatively, the substrate may be a flexible substrate and may include a plastic with excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphtalate, polyarylate (PAR), polyetherimide, or any combination thereof.

[0144] The first electrode (110) can be formed, for example, by providing a material for the first electrode on the substrate using a deposition method or a sputtering method. When the first electrode (110) is an anode, a material with a high work function that facilitates hole injection can be used as the material for the first electrode.

[0145] The first electrode (110) may be a reflective electrode, a semi-transparent electrode, or a transparent electrode. To form the first electrode (110) which is a transparent electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used as the material for the first electrode. Alternatively, to form the first electrode (110) which is a semi-transparent electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof may be used as the material for the first electrode.

[0146] The first electrode (110) may have a single-layer structure consisting of a single layer or a multi-layer structure including multiple layers. For example, the first electrode (110) may have a three-layer structure of ITO / Ag / ITO.

[0147] [Middle layer (130)]

[0148] An intermediate layer (130) is disposed on the upper portion of the first electrode (110). The intermediate layer (130) includes a light-emitting layer (133).

[0149] The above intermediate layer (130) may further include a hole transport region (131) disposed between the first electrode (110) and the light-emitting layer (133) and an electron transport region (135) disposed between the light-emitting layer (133) and the second electrode (150).

[0150] The above intermediate layer (130) may further include, in addition to various organic materials, metal-containing compounds such as organometallic compounds, inorganic materials such as quantum dots, etc.

[0151] Meanwhile, the intermediate layer (130) may include i) two or more emitting units sequentially stacked between the first electrode (110) and the second electrode (150), and ii) a charge generation layer disposed between the two emitting units. When the intermediate layer (130) includes the emitting units and charge generation layer as described above, the emitting element (10) may be a tandem emitting element.

[0152] [Middle layer (130) with a positive transport area (131)]

[0153] The hole transport region (131) may have i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a plurality of different materials, or iii) a multilayer structure including a plurality of layers containing a plurality of different materials.

[0154] The hole transport region (131) may include a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting auxiliary layer, an electron blocking layer (EBL), or any combination thereof.

[0155] For example, the hole transport region (131) may have a multilayer structure of a hole injection layer / hole transport layer, a hole injection layer / hole transport layer / light-emitting auxiliary layer, a hole injection layer / light-emitting auxiliary layer, a hole transport layer / light-emitting auxiliary layer, or a hole injection layer / hole transport layer / electron blocking layer stacked sequentially from the first electrode (110).

[0156] The hole transport region (131) may include a compound represented by the following chemical formula 201, a compound represented by the following chemical formula 202, or any combination thereof:

[0157] <Chemical Formula 201>

[0158]

[0159] <Chemical Formula 202>

[0160]

[0161] Among the above chemical formulas 201 and 202,

[0162] L 201 to L 204 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0163] L 205 은, *-O-*', *-S-*', *-N(Q 201 )-*', at least one R 10a C1-C substituted or unsubstituted 20 alkylene group, at least one R 10a C2-C substituted or unsubstituted 20 alkenylene group, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0164] xa1 to xa4 are independently one of integers 0 to 5, and

[0165] xa5 is one of integers from 1 to 10, and

[0166] R 201 to R 204 and Q 201 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0167] R 201 and R 202 is optionally a single bond, at least one R 10a A C1-C5 alkylene group substituted or unsubstituted with or at least one R 10a Connected to each other through C2-C5 alkenylene groups substituted or unsubstituted, at least one R 10a C8-C substituted or unsubstituted 60 It can form polycyclic groups (e.g., carbazole groups, etc.) (e.g., refer to the following compound HT16, etc.),

[0168] R 203 and R 204 is optionally a single bond, at least one R 10a A C1-C5 alkylene group substituted or unsubstituted with or at least one R 10a Connected to each other through C2-C5 alkenylene groups substituted or unsubstituted, at least one R 10a C8-C substituted or unsubstituted 60 It can form polycyclic groups, and

[0169] na1 can be one of integers from 1 to 4.

[0170] For example, each of the above chemical formulas 201 and 202 may include at least one of the group represented by the following chemical formulas CY201 to CY217:

[0171]

[0172] Among the above chemical formulas CY201 to CY217, R 10b and R 10c Descriptions of each of R in this specification 10a Refer to the explanation for, and ring CY 201 Inner ring CY 204 are independently of each other, C3-C 20 Carbocyclic group or C1-C 20It is a heterocyclic group, and at least one hydrogen of the chemical formulas CY201 to CY217 is R as described in this specification. 10a It can be substituted or unsubstituted.

[0173] According to one embodiment, among the chemical formulas CY201 to CY217, the ring CY 201 Inner ring CY 204 It can be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group independently of each other.

[0174] According to another embodiment, each of the above formulas 201 and 202 may include at least one of the group represented by the formulas CY201 to CY203.

[0175] According to another embodiment, the formula 201 may each include at least one of the group represented by formulas CY201 to CY203 and at least one of the group represented by formulas CY204 to CY217.

[0176] According to another embodiment, xa1 in the above chemical formula 201 is 1, and R 201 is a group represented by one of the above chemical formulas CY201 to CY203, xa2 is 0, and R 202 may be a group represented by one of the above chemical formulas CY204 to CY207.

[0177] According to another embodiment, each of the above formulas 201 and 202 may not include the group represented by the above formulas CY201 to CY203.

[0178] According to another embodiment, each of the above formulas 201 and 202 may not include the group represented by formulas CY201 to CY203 and may include at least one of the group represented by formulas CY204 to CY217.

[0179] As another example, each of the above chemical formulas 201 and 202 may not include the group represented by the above chemical formulas CY201 to CY217.

[0180] For example, the hole transport region (131) is one of the following compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PEDOT / PSS (Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), PANI / CSA (Polyaniline / Camphor sulfonic acid It may include (polyaniline / campersulfonic acid)), PANI / PSS (polyaniline / poly(4-styrenesulfonate)), or any combination thereof:

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191] The thickness of the hole transport region (131) may be about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. If the hole transport region (131) includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region (131), the hole injection layer, and the hole transport layer satisfy the ranges described above, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

[0192] The light-emitting auxiliary layer is a layer that increases light emission efficiency by compensating for the optical resonance distance according to the wavelength of light emitted from the light-emitting layer (133), and the electron blocking layer is a layer that prevents electron injection from the electron transport region (135). The light-emitting auxiliary layer and the electron blocking layer may include materials as described above.

[0193] [p-dopant]

[0194] The hole transport region (131) may include a charge-generating material to improve conductivity in addition to the material described above. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region (131) (e.g., in the form of a single layer consisting of the charge-generating material).

[0195] The above charge-generating material may be, for example, a p-dopant.

[0196] For example, the LUMO energy level of the above p-dopant may be -3.5 eV or less.

[0197] According to one embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, an element EL1 and an element EL2-containing compound, or any combination thereof.

[0198] Examples of the above quinone derivatives may include TCNQ, F4-TCNQ, etc.

[0199] Examples of the above cyano group-containing compounds may include HAT-CN, compounds represented by the following chemical formula 221, etc.

[0200]

[0201] <Chemical Formula 221>

[0202]

[0203] Of the above chemical formula 221,

[0204] R 221 to R 223 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0205] The above R 221 to R 223 At least one of which is independently substituted with a cyano group; -F; -Cl; -Br; -I; a cyano group, -F, -Cl, -Br, -I, or any combination thereof C1-C 20 C3-C substituted with an alkyl group; or any combination thereof. 60 Carbocyclic group or C1-C 60 It can be a heterocyclic group.

[0206] Among the above-mentioned compounds containing elements EL1 and EL2, element EL1 may be a metal, a metalloid, or a combination thereof, and element EL2 may be a nonmetal, a metalloid, or a combination thereof.

[0207] Examples of the above metals are alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); Transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.); etc. may be included.

[0208] Examples of the above metalloids may include silicon (Si), antimony (Sb), tellurium (Te), etc.

[0209] Examples of the above nonmetals may include oxygen (O), halogens (e.g., F, Cl, Br, I, etc.).

[0210] For example, the above-mentioned element EL1 and element EL2-containing compounds may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metal tellurides, or any combination thereof.

[0211] Examples of the above metal oxides may include tungsten oxide (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxide (e.g., VO, V2O3, VO2, V2O5, etc.), molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), rhenium oxide (e.g., ReO3, etc.).

[0212] Examples of the above metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, etc.

[0213] Examples of the above alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, etc.

[0214] Examples of the above alkaline earth metal halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, etc.

[0215] Examples of the above transition metal halides include titanium halides (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3, VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halides (e.g., TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), and tungsten. Halides (e.g., WF3, WCl3, WBr3, WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr2, ReI2, etc.), iron halides (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halides (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halides (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halides (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.),It may include silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.), etc.

[0216] Examples of the above-mentioned transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (e.g., InI3, etc.), tin halides (e.g., SnI2, etc.), etc.

[0217] Examples of the above lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3SmCl3, YbBr, YbBr2, YbBr3SmBr3, YbI, YbI2, YbI3, SmI3, etc.

[0218] Examples of the metalloid halides mentioned above may include antimony halides (e.g., SbCl5, etc.).

[0219] Examples of the above metal tellurides include alkali metal tellurides (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), post-transition metal tellurides (e.g., ZnTe, etc.), and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe). It may include TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.

[0220] [Emitting layer (133) in the middle layer (130)]

[0221] When the light-emitting element (10) is a full-color light-emitting element, the light-emitting layer (133) may be patterned into a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer for each individual subpixel. Alternatively, the light-emitting layer (133) may have a structure in which two or more layers among the red light-emitting layer, the green light-emitting layer, and the blue light-emitting layer are stacked in contact or spaced apart, or may have a structure in which two or more materials among the red light-emitting material, the green light-emitting material, and the blue light-emitting material are mixed without layer separation, thereby emitting white light.

[0222] The light-emitting layer (133) may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

[0223] The content of the dopant in the above-mentioned light-emitting layer (133) may be about 0.01 to about 15 parts by weight per 100 parts by weight of the host.

[0224] Alternatively, the light-emitting layer (133) may include quantum dots.

[0225] Meanwhile, the light-emitting layer (133) may include a delay fluorescent material. The delay fluorescent material may act as a host or dopant in the light-emitting layer (133).

[0226] The thickness of the light-emitting layer (133) may be about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-emitting layer (133) satisfies the range described above, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.

[0227] [Host]

[0228] The above host may include a compound represented by the following chemical formula 301:

[0229] <Chemical Formula 301>

[0230] [Ar301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0231] Among the above chemical formula 301,

[0232] Ar 301 and L 301 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0233] xb11 is 1, 2, or 3, and

[0234] xb1 is one of integers from 0 to 5, and

[0235] R 301 Silver, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, at least one R 10a C1-C substituted or unsubstituted 60 alkyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkenyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkynyl group, at least one R 10a C1-C substituted or unsubstituted 60 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group, at least one R 10a C1-C substituted or unsubstituted 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 ), -N(Q 301 )(Q 302 ), -B(Q 301 )(Q 302 ), -C(=O)(Q301 ), -S(=O)2(Q 301 ), or -P(=O)(Q 301 )(Q 302 ) and,

[0236] xb21 is one of integers from 1 to 5, and

[0237] Q 301 to Q 303 For a description of each, refer to the description of Q1 in this specification.

[0238] For example, if xb11 in the above chemical formula 301 is 2 or more, then 2 or more Ar 301 They can be connected to each other through a single bond.

[0239] As another example, the host may include a compound represented by the following chemical formula 301-1, a compound represented by the following chemical formula 301-2, or any combination thereof:

[0240] <Chemical Formula 301-1>

[0241]

[0242] <Chemical Formula 301-2>

[0243]

[0244] Among the above chemical formulas 301-1 to 301-2,

[0245] Ring A 301 inner ring A 304 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0246] X 301 is O, S, N-[(L 304 ) xb4 -R 304 ], C(R 304 )(R 305 ), or Si(R 304)(R 305 ) and,

[0247] xb22 and xb23 are independently 0, 1, or 2, and

[0248] L 301 , xb1 and R 301 For descriptions thereof, refer to those described in this specification, and

[0249] L 302 to L 304 The descriptions regarding are independent of each other, the above L 301 Refer to the explanation for,

[0250] The descriptions for xb2 to xb4 are independent of each other, and refer to the description for xb1 above, and

[0251] R 302 to R 305 and R 311 to R 314 The explanation for each of the above R 301 Refer to the explanation for.

[0252] As another example, the host may include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. For example, the host may include a Be complex (e.g., compound H55 below), an Mg complex, a Zn complex, or any combination thereof.

[0253] As another example, the host may comprise one of the following compounds H1 to H124, ADN (9,10-Di(2-naphthyl)anthracene), MADN (2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), TBADN (9,10-di-(2-naphthyl)-2-t-butyl-anthracene), CBP (4,4′-bis(N-carbazolyl)-1,1′-biphenyl), mCP (1,3-di-9-carbazolylbenzene), TCP (1,3,5-tri(carbazol-9-yl)benzene), mCBP (3,3-Di(9H-carbazol-9-yl)biphenyl), or any combination thereof:

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268] [Phosphorescent Dopant]

[0269] The above phosphorescent dopant may include at least one transition metal as a central metal.

[0270] The phosphorescent dopant may include a monodenate ligand, a two-bed ligand, a three-bed ligand, a four-bed ligand, a five-bed ligand, a six-bed ligand, or any combination thereof.

[0271] The above phosphorescent dopant may be electrically neutral.

[0272] For example, the phosphorescent dopant may include an organometallic compound represented by the following chemical formula 401:

[0273] <Chemical Formula 401>

[0274] M(L 401 ) xc1 (L 402 ) xc2

[0275] <Chemical Formula 402>

[0276]

[0277] Among the above chemical formulas 401 and 402,

[0278] M is a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)), and

[0279] L 401 is a ligand represented by the above chemical formula 402, xc1 is 1, 2, or 3, and if xc1 is 2 or more, 2 or more L 401 They are identical or different from each other,

[0280] L 402 is an organic ligand, xc2 is 0, 1, 2, 3, or 4, and if xc2 is 2 or more, 2 or more L 402 are identical or different from each other,

[0281] X 401and X 402 are independently nitrogen or carbon, and

[0282] Ring A 401 and ring A 402 are independently of each other, C3-C 60 Carbocyclic group or C1-C 60 It is a heterocyclic group, and

[0283] T 401 is a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*', *-C(Q 411 )(Q 412 )-*', *-C(Q 411 )=C(Q 412 )-*', *-C(Q 411 )=*' or *=C(Q 411 )=*' and,

[0284] X 403 and X 404 are independently of each other, chemical bonds (e.g., covalent bonds or coordinate bonds), O, S, N(Q 413 ), B(Q 413 ), P(Q 413 ), C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ) and,

[0285] Above Q 411 to Q 414 For descriptions regarding each, refer to the description of Q1 in this specification, and

[0286] R 401 and R 402 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, at least one R 10a C1-C substituted or unsubstituted 20 alkyl group, at least one R 10a C1-C substituted or unsubstituted 20 Alkoxy group, at least one R 10aC3-C substituted or unsubstituted 60 Carbocyclic group, at least one R 10a C1-C substituted or unsubstituted 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q 401 ) or -P(=O)(Q 401 )(Q 402 ) and,

[0287] Above Q 401 to Q 403 For descriptions regarding each, refer to the description of Q1 in this specification, and

[0288] xc11 and xc12 are independently one of integers from 0 to 10, and

[0289] In the above chemical formula 402, * and *' are each binding sites with M in the above chemical formula 401.

[0290] For example, i) X in the above chemical formula 402 401 is nitrogen, and X 402 is carbon, or ii) X 401 and X 402 All of it can be nitrogen.

[0291] As another example, if xc1 in the above chemical formula 402 is 2 or more, then 2 or more L 401 Two of the rings A 401 is optionally, the connector T 402 Connected to each other through, or 2 rings A 402 is optionally, the connector T 403 They can be connected to each other through (see compounds PD1 to PD4 and PD7 below). The above T 402 and T 403The descriptions for each of T in this specification 401 Refer to the explanation for.

[0292] L in the above chemical formula 401 402 can be any organic ligand. For example, the above L 402 It may include a halogen group, a diketone group (e.g., acetylacetonate group), a carboxylic acid group (e.g., picolinate group), -C (=O), an isonitrile group, a -CN group, a phosphorus group (e.g., phosphine group, phosphite group, etc.), or any combination thereof.

[0293] The above phosphorescent dopant may include, for example, one of the following compounds PD1 to PD25, or any combination thereof:

[0294]

[0295]

[0296]

[0297] [Fluorescent Dopant]

[0298] The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.

[0299] For example, the fluorescent dopant may include a compound represented by the following chemical formula 501:

[0300] <Chemical Formula 501>

[0301]

[0302] Among the above chemical formula 501,

[0303] Ar 501 , L 501 to L 503 , R 501 and R 502 are independent of each other, at least one R 10a C3-C substituted or unsubstituted60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0304] xd1 to xd3 are independently 0, 1, 2, or 3, and

[0305] xd4 can be 1, 2, 3, 4, 5, or 6.

[0306] For example, Ar in the above chemical formula 501 501 It may include a condensed ring group in which three or more monocyclic groups are condensed together (e.g., anthracene group, chrysene group, pyrene group, etc.).

[0307] As another example, xd4 in the above chemical formula 501 can be 2.

[0308] For example, the fluorescent dopant may include one of the following compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316] [Delayed Fluorescence]

[0317] The light-emitting layer (133) may include a delayed fluorescent material.

[0318] In this specification, the delayed fluorescent material may be selected from any compound capable of emitting delayed fluorescence by a delayed fluorescence emission mechanism.

[0319] The delay fluorescent material included in the light-emitting layer (133) can act as a host or a dopant depending on the type of other material included in the light-emitting layer (133).

[0320] According to one embodiment, the difference between the triplet energy level (eV) of the delay fluorescent material and the singlet energy level (eV) of the delay fluorescent material may be 0 eV or more and 0.5 eV or less. By satisfying the range described above, the reverse energy transfer (up-conversion) from the triplet state to the singlet state of the delay fluorescent material is effectively achieved, thereby improving the luminous efficiency of the light-emitting device (10).

[0321] For example, the above-mentioned delay fluorescent material comprises: i) at least one electron donor (e.g., a π-electron-excess C3-C such as a carbazole group). 60 Cyclic group (π electron-rich C3-C 60 cyclic group) etc.) and at least one electron acceptor (e.g., sulfoxide group, cyano group, π electron-deficient nitrogenous C1-C 60 cyclic group (π electron-deficient nitrogen-containing C1-C 60 ii) a substance containing a cyclic group, etc., and ii) a C8-C containing two or more cyclic groups condensed while sharing boron (B). 60 It may include materials including polycyclic groups.

[0322] Examples of the above-mentioned delayed fluorescent materials may include at least one of the following compounds DF1 to DF9:

[0323]

[0324]

[0325] [Quantum Dot]

[0326] The light-emitting layer (133) may include quantum dots.

[0327] In this specification, a quantum dot refers to a crystal of a semiconductor compound and may include any material capable of emitting light of various emission wavelengths depending on the size of the crystal.

[0328] The diameter of the above quantum dots may be, for example, about 1 nm to 10 nm.

[0329] The above quantum dots can be synthesized by a wet chemical process, an organometallic chemical vapor deposition process, a molecular beam epitaxy process, or a similar process.

[0330] The above wet chemical process is a method of growing quantum dot particle crystals after mixing an organic solvent and a precursor material. When the crystals grow, the organic solvent naturally acts as a dispersant coordinated to the surface of the quantum dot crystals and controls the growth of the crystals. Therefore, the growth of quantum dot particles can be controlled through a process that is easier and lower cost than vapor deposition methods such as Metal Organic Chemical Vapor Deposition (MOCVD) or Molecular Beam Epitaxy (MBE).

[0331] The above quantum dots may include a group II-VI semiconductor compound; a group III-V semiconductor compound; a group III-VI semiconductor compound; a group I-III-VI semiconductor compound; a group IV-VI semiconductor compound; a group IV element or compound; or any combination thereof.

[0332] Examples of the above-mentioned group II-VI semiconductor compounds include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, etc.; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, etc.; It may include four-element compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, etc.; or any combination thereof.

[0333] Examples of the above III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, GaAlNP, etc.; quaternary compounds such as GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, etc.; or any combination thereof. Meanwhile, the above III-V semiconductor compounds may further include a group II element. Examples of III-V semiconductor compounds containing additional group II elements may include InZnP, InGaZnP, InAlZnP, etc.

[0334] Examples of the above-mentioned group III-VI semiconductor compounds may include binary compounds such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, etc.; ternary compounds such as InGaS3, InGaSe3, etc.; or any combination thereof.

[0335] Examples of the above-mentioned group I-III-VI semiconductor compounds may include ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, etc.; or any combination thereof.

[0336] Examples of the above-mentioned group IV-VI semiconductor compounds may include binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, etc.; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, etc.; quaternary compounds such as SnPbSSe, SnPbSeTe, SnPbSTe, etc.; or any combination thereof.

[0337] The above Group IV elements or compounds may include single-element compounds such as Si, Ge, etc.; dual-element compounds such as SiC, SiGe, etc.; or any combination thereof.

[0338] Each element included in the multi-element compounds, such as the above-mentioned binary compounds, ternary compounds, and quaternary compounds, may exist within the particle at a uniform or non-uniform concentration.

[0339] Meanwhile, the above quantum dot may have a single structure in which the concentration of each element contained in the quantum dot is uniform, or a core-shell dual structure. For example, the material contained in the core and the material contained in the shell may be different from each other.

[0340] The shell of the quantum dot can serve as a protective layer to maintain semiconductor properties by preventing chemical degradation of the core, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be a single layer or a multilayer. The interface between the core and the shell may have a concentration gradient in which the concentration of elements present in the shell decreases toward the center.

[0341] Examples of the shell of the above quantum dot include oxides of metals, metalloids, or nonmetals, semiconductor compounds, or combinations thereof. Examples of the oxides of metals, metalloids, or nonmetals may include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, etc.; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, etc.; or any combination thereof. Examples of the above semiconductor compounds may include group II-VI semiconductor compounds; group III-V semiconductor compounds; group III-VI semiconductor compounds; group I-III-VI semiconductor compounds; group IV-VI semiconductor compounds; or any combination thereof, as described in this specification. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.

[0342] Quantum dots can have a full width of half maximum (FWHM) of the emission wavelength spectrum of about 45 nm or less, specifically about 40 nm or less, and more specifically about 30 nm or less, and color purity or color reproducibility can be improved in this range. In addition, since the light emitted through these quantum dots is emitted in all directions, the wide viewing angle can be improved.

[0343] In addition, the shape of the quantum dots can specifically be spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplate-like particles, etc.

[0344] By controlling the size of the quantum dots, the energy band gap can be controlled, allowing light of various wavelengths to be obtained from the quantum dot light-emitting layer. Therefore, by using quantum dots of different sizes, a light-emitting device that emits light of various wavelengths can be realized. Specifically, the size of the quantum dots can be selected to emit red, green, and / or blue light. Additionally, the size of the quantum dots can be configured to emit white light by combining light of various colors.

[0345] [Electronic transport region (135) in the middle layer (130)]

[0346] The electron transport region (135) may have i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a plurality of different materials, or iii) a multilayer structure including a plurality of layers containing a plurality of different materials.

[0347] The electron transport region (135) may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer (ETL), an electron injection layer, or any combination thereof.

[0348] For example, the electron transport region (135) may have a structure such as an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron control layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / electron injection layer, which are stacked sequentially from the light-emitting layer (133).

[0349] The electron transport region (135) (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer among the electron transport region (135)) is at least one π electron-deficient nitrogen-containing C1-C 60 cyclic group (π electron-deficient nitrogen-containing C1-C 60 It may include metal-free compounds containing a cyclic group.

[0350] For example, the electron transport region (135) may include a compound represented by the following chemical formula 601.

[0351] <Chemical Formula 601>

[0352] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0353] Among the above chemical formula 601,

[0354] Ar 601 , and L 601 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and

[0355] xe11 is 1, 2, or 3, and

[0356] xe1 is 0, 1, 2, 3, 4, or 5, and

[0357] R601 is, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group, at least one R 10a C1-C substituted or unsubstituted 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), or -P(=O)(Q 601 )(Q 602 ) and,

[0358] Above Q 601 to Q 603 For descriptions regarding each, refer to the description of Q1 in this specification, and

[0359] xe21 is 1, 2, 3, 4, or 5, and

[0360] The above Ar 601 , L 601 and R 601 At least one of them is independent of each other, at least one R 10a π electron-deficient nitrogenous C1-C substituted or unsubstituted 60 It could be a click group.

[0361] For example, if xe11 in the above chemical formula 601 is 2 or more, then 2 or more Ar 601 They can be connected to each other through a single bond.

[0362] As another example, Ar in the above chemical formula 601 601 It may be a substituted or unsubstituted anthracene group.

[0363] As another example, the electron transport region (135) may include a compound represented by the following chemical formula 601-1:

[0364] <Chemical Formula 601-1>

[0365]

[0366] In the above chemical formula 601-1,

[0367] X 614 is N or C(R 614 ) and, X 615 is N or C(R 615 ) and, X 616 is N or C(R 616 ) and, X 614 To X 616 At least one of them is N, and

[0368] L 611 to L 613 The explanation for each of the above L 601 Refer to the explanation for,

[0369] For descriptions of xe611 to xe613, refer to the description of xe1 above, and

[0370] R 611 to R 613 The explanation for each of the above R 601 Refer to the explanation for,

[0371] R 614 to R 616 They are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group, C1-C 20 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group, or at least one R 10a C1-C substituted or unsubstituted 60 It can be a heterocyclic group.

[0372] For example, xe1 and xe611 to xe613 in the above chemical formulas 601 and 601-1 may be 0, 1, or 2 independently of each other.

[0373] The electron transport region (135) may comprise one of the following compounds ET1 to ET45, BCP (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-Diphenyl-1,10-phenanthroline), Alq3, BAlq, TAZ, NTAZ, TSPO1 (diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide), or any combination thereof:

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381] The thickness of the electron transport region (135) may be about 160 Å to about 5000 Å, for example, about 100 Å to about 4000 Å. If the electron transport region (135) includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be independently about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. If the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and / or the electron transport layer satisfies the ranges described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

[0382] The above electron transport region (135) (for example, the electron transport layer of the above electron transport region (135)) may further include a metal-containing material in addition to the material described above.

[0383] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ions of the alkali metal complex may be Li ions, Na ions, K ions, Rb ions, or Cs ions, and the metal ions of the alkaline earth metal complex may be Be ions, Mg ions, Ca ions, Sr ions, or Ba ions. The ligands coordinated to the metal ions of the alkali metal complex and the alkaline earth metal complex may independently include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0384] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, the following compounds ET-D1 (LiQ) or ET-D2:

[0385]

[0386] The electron transport region (135) may include an electron injection layer that facilitates electron injection from the second electrode (150). The electron injection layer may be in direct contact with the second electrode (150).

[0387] The electron injection layer may have i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a plurality of different materials, or iii) a multilayer structure having a plurality of layers containing a plurality of different materials.

[0388] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0389] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0390] The alkali metal-containing compound, alkaline earth metal-containing compound and the rare earth metal-containing compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), tellurides, or any combination thereof of the alkali metal, alkaline earth metal, and rare earth metal, respectively.

[0391] The above alkali metal-containing compound may include alkali metal oxides such as Li2O, Cs2O, K2O, etc., alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, etc., or any combination thereof. The above alkaline earth metal-containing compound may include BaO, SrO, CaO, Ba x Sr 1-x O(x is 0 <x<1를 만족하는 실수임), Ba x Ca 1-xO(x is 0 <x<1를 만족하는 실수임) 등과 같은 알칼리 토금속 화합물을 포함할 수 있다. 상기 희토류 금속-함유 화합물은, YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, 또는 이의 임의의 조함을 포함할 수 있다. 또는, 상기 희토류 금속-함유 화합물은, 란타나이드 금속 텔루라이드를 포함할 수 있다. 상기 란타나이드 금속 텔루라이드의 예는, LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, Lu2Te3등을 포함할 수 있다.

[0392] The above alkali metal complex, alkaline earth metal complex, and rare earth metal complex may comprise i) one of the ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and ii) a ligand bound to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0393] The electron injection layer described above may consist only of alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof, or may further include organic materials (e.g., compounds represented by the chemical formula 601).

[0394] According to one embodiment, the electron injection layer may be composed of i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, etc.

[0395] If the electron injection layer further comprises an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix containing the organic material.

[0396] The thickness of the electron injection layer may be about 1 Å to about 100 Å or about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0397] [Second electrode (150)]

[0398] A second electrode (150) is disposed on the upper portion of the intermediate layer (130) as described above. The second electrode (150) may be a cathode, which is an electron injection electrode. In this case, a metal, alloy, electrically conductive compound, or any combination thereof having a low work function may be used as the material for the second electrode (150).

[0399] The second electrode (150) may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode (150) may be a transmissive electrode, a semitransmissive electrode, or a reflective electrode.

[0400] The second electrode (150) may have a single-layer structure or a multi-layer structure having multiple layers.

[0401] [Capping layer]

[0402] A first capping layer may be disposed on the outer side of the first electrode (110), and / or a second capping layer may be disposed on the outer side of the second electrode (150). Specifically, the light-emitting element (10) may have a structure in which the first capping layer, the first electrode (110), the intermediate layer (130), and the second electrode (150) are stacked in order, a structure in which the first electrode (110), the intermediate layer (130), the second electrode (150), and the second capping layer are stacked in order, or a structure in which the first capping layer, the first electrode (110), the intermediate layer (130), the second electrode (150), and the second capping layer are stacked in order.

[0403] Light generated in the light-emitting layer (133) of the intermediate layer (130) of the light-emitting element (10) can be emitted to the outside through the first electrode (110), which is a semi-transparent electrode or a transparent electrode, and the first capping layer, and light generated in the light-emitting layer (133) of the intermediate layer (130) of the light-emitting element (10) can be emitted to the outside through the second electrode (150), which is a semi-transparent electrode or a transparent electrode, and the second capping layer.

[0404] The first capping layer and the second capping layer can serve to improve external light emission efficiency based on the principle of constructive interference. As a result, the light extraction efficiency of the light-emitting element (10) is increased, and the light emission efficiency of the light-emitting element (10) can be improved.

[0405] Each of the above first capping layer and second capping layer may include a material having a refractive index of 1.6 or higher (at 589 nm).

[0406] The first capping layer and the second capping layer may independently be an organic capping layer containing organic material, an inorganic capping layer containing inorganic material, or a composite capping layer containing organic and inorganic material.

[0407] At least one of the first capping layer and the second capping layer may independently comprise a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally be substituted with a substituent comprising O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. According to one embodiment, at least one of the first capping layer and the second capping layer may independently comprise an amine group-containing compound.

[0408] For example, at least one of the first capping layer and the second capping layer may independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

[0409] According to another embodiment, at least one of the first capping layer and the second capping layer may independently comprise one of the compounds HT28 to HT33, one of the following compounds CP1 to CP6, β-NPB, or any of the same:

[0410]

[0411]

[0412] [Electronic device]

[0413] The light-emitting element may be included in various electronic devices. For example, an electronic device including the light-emitting element may be a light-emitting device, an authentication device, etc.

[0414] The electronic device (e.g., light-emitting device) may further include, in addition to the light-emitting element, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or color conversion layer may be disposed in at least one direction of propagation of light emitted from the light-emitting element. For example, the light emitted from the light-emitting element may be blue light or white light. Refer to the description of the light-emitting element above. According to one embodiment, the color conversion layer may include quantum dots. The quantum dots may be, for example, a quantum dot-containing material as described herein.

[0415] The electronic device may include a first substrate. The first substrate may include a plurality of subpixel regions, the color filter may include a plurality of color filter regions corresponding to each of the plurality of subpixel regions, and the color conversion layer may include a plurality of color conversion regions corresponding to each of the plurality of subpixel regions.

[0416] A pixel defining film is placed between the plurality of subpixel regions above to define each subpixel region.

[0417] The above color filter may further include a plurality of color filter regions and a light-blocking pattern disposed between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light-blocking pattern disposed between the plurality of color conversion regions.

[0418] The plurality of color filter regions (or plurality of color conversion regions) comprises a first region emitting a first color light; a second region emitting a second color light; and / or a third region emitting a third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the plurality of color filter regions (or plurality of color conversion regions) may include quantum dots. Specifically, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. Refer to the description of quantum dots as provided in this specification. The first region, the second region, and / or the third region may each further include scatterers.

[0419] For example, the light-emitting element may emit a first light, the first region may absorb the first light to emit a first-1 color light, the second region may absorb the first light to emit a second-1 color light, and the third region may absorb the first light to emit a third-1 color light. In this case, the first-1 color light, the second-1 color light, and the third-1 color light may have different maximum emission wavelengths. Specifically, the first light may be blue light, the first-1 color light may be red light, the second-1 color light may be green light, and the third-1 color light may be blue light.

[0420] The above electronic device may further include a thin-film transistor in addition to the light-emitting element described above. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, and either one of the source electrode and the drain electrode may be electrically connected to either one of the first electrode and the second electrode of the light-emitting element.

[0421] The above thin-film transistor may further include a gate electrode, a gate insulating film, etc.

[0422] The above active layer may include crystalline silicon, amorphous silicon, organic semiconductor, oxide semiconductor, etc.

[0423] The electronic device may further include a sealing portion for sealing a light-emitting element. The sealing portion may be disposed between the color filter and / or color conversion layer and the light-emitting element. The sealing portion allows light from the light-emitting element to be emitted to the outside while simultaneously blocking external air and moisture from penetrating the light-emitting element. The sealing portion may be a sealing substrate comprising a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer comprising one or more organic and / or inorganic layers. If the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.

[0424] On the sealing portion, in addition to the color filter and / or color conversion layer, various functional layers may be additionally disposed depending on the application of the electronic device. Examples of the functional layers may include a touchscreen layer, a polarizing layer, etc. The touchscreen layer may be a pressure-sensitive touchscreen layer, a capacitive touchscreen layer, or an infrared touchscreen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual using biometric information (e.g., fingertip, pupil, etc.).

[0425] The authentication device described above may further include means for collecting biometric information in addition to the light-emitting element described above.

[0426] The above electronic device can be applied to various displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical devices (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram display devices, ultrasound diagnostic devices, endoscope display devices), fish finders, various measuring instruments, instruments (e.g., instruments for vehicles, aircraft, and ships), projectors, etc.

[0427] [Explanation of Figures 3 and 4]

[0428] FIG. 3 is a cross-sectional view of a light-emitting device according to one embodiment of the present invention.

[0429] The light-emitting device of FIG. 3 includes a substrate (100), a thin-film transistor (TFT), a light-emitting element, and a sealing portion (300) that seals the light-emitting element.

[0430] The substrate (100) may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer (210) may be disposed on the substrate (100). The buffer layer (210) may prevent the penetration of impurities through the substrate (100) and may serve to provide a flat surface on the upper surface of the substrate (100).

[0431] A thin-film transistor (TFT) may be disposed on the buffer layer (210). The thin-film transistor (TFT) may include an active layer (220), a gate electrode (240), a source electrode (260), and a drain electrode (270).

[0432] The active layer (220) may include an inorganic semiconductor, an organic semiconductor, or an oxide semiconductor such as silicon or polysilicon, and includes a source region, a drain region, and a channel region.

[0433] A gate insulating film (230) for insulating the active layer (220) and the gate electrode (240) may be disposed on the upper part of the active layer (220), and a gate electrode (240) may be disposed on the upper part of the gate insulating film (230).

[0434] An interlayer insulating film (250) may be disposed on the upper portion of the gate electrode (240). The interlayer insulating film (250) is disposed between the gate electrode (240) and the source electrode (260) and between the gate electrode (240) and the drain electrode (270) to insulate them.

[0435] A source electrode (260) and a drain electrode (270) may be disposed on the interlayer insulating film (250). The interlayer insulating film (250) and the gate insulating film (230) may be formed so as to expose the source region and the drain region of the active layer (220), and the source electrode (260) and the drain electrode (270) may be disposed to be in contact with the exposed source region and the drain region of the active layer (220).

[0436] Such a thin-film transistor (TFT) can be electrically connected to a light-emitting element to drive the light-emitting element and is covered and protected by a passivation layer (280). The passivation layer (280) may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light-emitting element is provided on the passivation layer (280). The light-emitting element includes a first electrode (110), an intermediate layer (130), and a second electrode (150).

[0437] The first electrode (110) may be disposed on the passivation layer (280). The passivation layer (280) may be disposed so as to expose a certain area without covering the entire drain electrode (270), and the first electrode (110) may be disposed to be connected to the exposed drain electrode (270).

[0438] A pixel defining film (290) including an insulating material may be disposed on the first electrode (110). The pixel defining film (290) exposes a predetermined area of ​​the first electrode (110), and an intermediate layer (130) may be formed in the exposed area. The pixel defining film (290) may be a polyimide or polyacrylic-based organic film. Although not shown in FIG. 3, some or more layers of the intermediate layer (130) may extend to the upper part of the pixel defining film (290) and be disposed in the form of a common layer.

[0439] A second electrode (150) is disposed on the intermediate layer (130), and a capping layer (170) may be additionally formed on the second electrode (150). The capping layer (170) may be formed to cover the second electrode (150).

[0440] A sealing portion (300) may be disposed on the capping layer (170). The sealing portion (300) may be disposed on a light-emitting element and serve to protect the light-emitting element from moisture or oxygen. The sealing portion (300) may include an inorganic film comprising silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy resin (e.g., AGE (aliphatic glycidyl ether), etc.) or any combination thereof; or a combination of an inorganic film and an organic film.

[0441] FIG. 4 is a cross-sectional view of a light-emitting device according to another embodiment of the present invention.

[0442] The light-emitting device of FIG. 4 is the same light-emitting device as FIG. 3, except that a light-blocking pattern (500) and a functional area (400) are additionally disposed on the upper part of the encapsulation portion (300). The functional area (400) may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. According to one embodiment, the light-emitting element included in the light-emitting device of FIG. 4 may be a tandem light-emitting element.

[0443] Each layer included in the hole transport region, the light-emitting layer, and the electron transport region can be formed in a predetermined area using various methods such as vacuum deposition, spin coating, casting, the Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0444] When each layer included in the hole transport region (131), the light-emitting layer (133), and each layer included in the electron transport region (135) are formed by vacuum deposition, the deposition conditions are, for example, a deposition temperature of about 100 to about 500°C, about 10 -8 to about 10 -3 Within a vacuum level of torr and a deposition rate range of about 0.01 to about 100 Å / sec, the material to be included in the layer to be formed and the structure of the layer to be formed can be selected.

[0445] [Definition of Terms]

[0446] C3-C in this specification 60 A carbocyclic group refers to a cyclic group consisting solely of carbon atoms with 3 to 60 carbon atoms, and C1-C 60 A heterocyclic group refers to a cyclic group having 1 to 60 carbon atoms that includes a heteroatom in addition to carbon. The above C3-C 60 Carbocyclic group and C1-C 60Each heterocyclic group may be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed together. For example, the above C1-C 60 The number of ring-forming atoms in a heterocyclic group can be 3 to 61.

[0447] In this specification, the cyclic group is the above C3-C 60 Carbocyclic group and C1-C 60 Includes all heterocyclic groups.

[0448] In this specification, π electron-excess C3-C 60 Cyclic group (π electron-rich C3-C 60 A cyclic group refers to a cyclic group having 3 to 60 carbon atoms that does not contain *-N=*' as a ring-forming moiety, and π electron-deficient nitrogen-containing C1-C 60 cyclic group (π electron-deficient nitrogen-containing C1-C 60 A cyclic group refers to a heterocyclic group having 1 to 60 carbon atoms containing *-N=*' as a ring-forming moiety.

[0449] for example,

[0450] The above C3-C 60The carbocyclic group may be i) group T1 or ii) a condensed ring group formed by the condensation of two or more groups T1 (e.g., cyclopentadiene group, adamantane group, norbornane group, benzene group, pentylene group, naphthalene group, azulene group, indacene group, acenaphtylene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, perylene group, pentapene group, heptylene group, naphthacene group, fisene group, hexacene group, pentacene group, rubicene group, coronene group, ovalene group, indene group, fluorene group, spiro-bifluorene group, benzofluorene group, indenophenanthrene group, or indenoanthracene group), and

[0451] The above C1-C 60A heterocyclic group is i) group T2, ii) a condensed ring group formed by the condensation of two or more groups T2, or iii) a condensed ring group formed by the condensation of one or more groups T2 and one or more groups T1 (e.g., pyrrole group, thiophene group, furan group, indole group, benzodole group, naphthoyndole group, isodole group, benzisoindole group, naphthoyisoindole group, benzocillol group, benzothiophene group, benzofuran group, carbazole group, dibenzocillol group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarbazole group, benzocillolocarbazole group, benzodolocarbazole group, benzoindolocarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthiophene group, Benzonaphthosilol group, benzofurodibenzofuran group, benzofurodibenzothiophen group, benzothienodibenzothiophen group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiaazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiaazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazolin group, benzoquinazolin group, phenanthroline group, sinoline group, phthalazine group, It may be the naftiridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluoren group, azadibenzocilol group, azadibenzothiophen group, azadibenzofuran group, etc.),

[0452] The above π electron-excess C3-C 60A cyclic group is i) group T1, ii) a condensed ring group formed by condensing two or more groups T1 together, iii) group T3, iv) a condensed ring group formed by condensing two or more groups T3 together, or v) a condensed ring group formed by condensing one or more groups T3 and one or more groups T1 together (e.g., the above C3-C 60 May be carbocylic group, pyrrole group, thiophene group, furan group, indole group, benzodole group, naphthoyndole group, isodole group, benzoisoindole group, naphthoyisoindole group, benzocylol group, benzothiophene group, benzofuran group, carbazole group, dibenzocylol group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarbazole group, benzocylololocarbazole group, benzodolocarbazole group, benzoindolocabazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthiophene group, benzonaphthocilol group, benzofurodibenzofuran group, benzofurodibenzothiophene group, benzothienodibenzothiophene group, etc.),

[0453] The above π electron-deficient nitrogen-containing C1-C 60A cyclic group is i) group T4, ii) a condensed ring group formed by the condensation of two or more groups T4, iii) a condensed ring group formed by the condensation of one or more groups T4 and one or more groups T1, iv) a condensed ring group formed by the condensation of one or more groups T4 and one or more groups T3, or v) a condensed ring group formed by the condensation of one or more groups T4, one or more groups T1, and one or more groups T3 (e.g., pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiaazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiaazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, It may be the isoquinoline group, benzoquinoline group, benzisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazolin group, benzoquinazolin group, phenanthroline group, sinoline group, phthalazine group, naftiridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluoren group, azadibenzocilol group, azadibenzothiophen group, azadibenzofuran group, etc.),

[0454] The above group T1 is a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, norbornane (or, bicyclo[2.2.1]heptane)) group, norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.1.1]octane group, or a benzene group, and

[0455] The above group T2 is a furan group, a thiophene group, a 1H-pyrrole group, a silol group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiaazole group, a thiadiazole group, an azacilol group, an azaborol group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group, and

[0456] The above group T3 is a furan group, a thiophene group, an 1H-pyrrole group, a silol group, or a borole group, and

[0457] The above group T4 may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazol group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiaazole group, a thiadiazole group, an azacilol group, an azaborol group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.

[0458] In this specification, the cyclic group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, π electron-excess C3-C 60 Cyclic group or π electron-deficient nitrogenous C1-C 60 The term "cyclic group" may be a group condensed to any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) depending on the structure of the chemical formula in which the term is used. For example, "benzene group" may be a benzo group, a phenyl group, a phenylene group, etc., which can be easily understood by a person skilled in the art depending on the structure of the chemical formula containing the "benzene group."

[0459] For example, 1 valence C3-C 60 Carbocyclic group and 1 valence C1-C 60 An example of a heterocyclic group is C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C1-C 60 It may include a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocondensed polycyclic group, and a divalent C3-C 60 Carbocyclic group and 1 valence C1-C 60 An example of a heterocyclic group is C3-C 10 Cycloalkylene group, C1-C 10 Heterocycloalkylene group, C3-C 10 Cycloalkenylene group, C1-C 10 Heterocycloalkenylene group, C6-C 60 Aryllene group, C1-C 60 It may include a heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group.

[0460] C1-C in this specification 60The alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, n -Propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -Pentyl, tert -Pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -Isopentyl group, n - Hexyl group, isohexyl group, sec -hexyl group, tert -hexyl group, n - heptyl group, isoheptyl group, sec -Heptyl group, tert -Heptyl group, n -Octyl group, iso-octyl group, sec -Octyl group, tert -Octyl group, n -Nonilgi, Isononilgi, sec -Playing, tert -Playing, n - Decyl group, isodecyl group, sec -Desil, tert - Includes decyl groups, etc. C1-C in this specification. 60 The alkylene group is the C1-C 60 It refers to a divalent group having the same structure as an alkyl group.

[0461] C2-C in this specification 60 The alkenyl group is C2-C 60 It refers to a monovalent hydrocarbon group comprising one or more carbon-carbon double bonds at the middle or terminal of an alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group, etc. In this specification, C2-C 60 The alkenylene group is the above C2-C 60 It refers to a divalent group having the same structure as an alkenyl group.

[0462] C2-C in this specification 60 The alkynyl group is C2-C 60It refers to a monovalent hydrocarbon group comprising one or more carbon-carbon triple bonds at the middle or terminal of an alkyl group, and specific examples thereof include ethinyl groups, propynyl groups, etc. In this specification, C2-C 60 The alkynylene group is the above C2-C 60 It refers to a divalent group having the same structure as an alkynyl group.

[0463] C1-C in this specification 60 The alkoxy group is -OA 101 (Here, A 101 The above C1-C 60 It refers to a monovalent group having the chemical formula of an alkyl group, and specific examples thereof include a methoxy group, an ethoxy group, an isopropyloxy group, etc.

[0464] C3-C in this specification 10 A cycloalkyl group refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, norbornanyl group (or, a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.1.1]octyl group, etc. In this specification, C3-C 10 The cycloalkylene group is the C3-C 10 It refers to a divalent group having the same structure as a cycloalkyl group.

[0465] C1-C in this specification 10A heterocycloalkyl group refers to a monovalent cyclic group having 1 to 10 carbon atoms, comprising at least one heteroatom as a ring-forming atom in addition to a carbon atom, and specific examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, etc. In this specification, C1-C 10 The heterocycloalkylene group is the C1-C 10 It refers to a divalent group having the same structure as a heterocycloalkyl group.

[0466] C3-C in this specification 10 A cycloalkenyl group refers to a monovalent cyclic group having 3 to 10 carbon atoms, having at least one carbon-carbon double bond within the ring, but not having aromaticity; specific examples thereof include cyclopentenyl groups, cyclohexenyl groups, cycloheptenyl groups, etc. In this specification, C3-C 10 The cycloalkenylene group is the above C3-C 10 It refers to a divalent group having the same structure as a cycloalkenyl group.

[0467] C1-C in this specification 10 The heterocycloalkenyl group is a monovalent cyclic group having 1 to 10 carbon atoms, comprising, in addition to the carbon atom, at least one heteroatom as a ring-forming atom, and has at least one double bond within the ring. The C1-C 10 Specific examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazoleyl groups, 2,3-dihydrofuranyl groups, 2,3-dihydrothiophenyl groups, etc. In this specification, C1-C 10 The heterocycloalkenylene group is the above C1-C 10 It refers to a divalent group having the same structure as a heterocycloalkenyl group.

[0468] C6-C in this specification 60An aryl group refers to a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms, and C6-C 60 An arylene group refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. The above C6-C 60 Specific examples of aryl groups include phenyl groups, penthalenyl groups, naphthyl groups, azulenyl groups, indacenyl groups, acenaphthyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, perylenyl groups, pentaphenyl groups, hepthalenyl groups, naphthacenyl groups, fisenyl groups, hexacenyl groups, penthacenyl groups, rubisenyl groups, coronenyl groups, ovalenyl groups, etc. The above C6-C 60 Aryl group and C6-C 60 If the arylene group contains two or more rings, the two or more rings can be condensed together.

[0469] C1-C in this specification 60 A heteroaryl group refers to a monovalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms, comprising at least one heteroatom as a ring-forming atom in addition to a carbon atom, and C1-C 60 A heteroarylene group refers to a divalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms, which additionally includes at least one heteroatom as a ring-forming atom in addition to the carbon atoms. 60 Specific examples of heteroaryl groups include pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolinyl groups, benzoquinolinyl groups, isoquinolinyl groups, benzisoquinolinyl groups, quinoxalinyl groups, benzoquinoxalinyl groups, quinazolinyl groups, benzoquinazolinyl groups, cinolinyl groups, phenanthrolinyl groups, phthalazinyl groups, naphthalidinyl groups, etc. The above C1-C 60 heteroaryl group and C1-C 60 When a heteroarylene group contains two or more rings, the two or more rings can be condensed together.

[0470] In this specification, a monovalent non-aromatic condensed polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are condensed together, and the entire molecule contains only carbon as a ring-forming atom and has non-aromaticity. Specific examples of the monovalent non-aromatic condensed polycyclic group include indenyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, indenopenantrenyl groups, indenoanthracenyl groups, etc. In this specification, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

[0471] In this specification, a monovalent non-aromatic condensed heteropolycyclic group means a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are condensed together, and in addition to carbon atoms as ring-forming atoms, at least one heteroatom is included, and the entire molecule is non-aromatic. Specific examples of the above monovalent non-aromatic heterocondensed polycyclic group include: a pyrrole group, a thiophenyl group, a furanyl group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzocylol group, a benzothiophenyl group, a benzofuranyl group, a carbazole group, a dibenzocylol group, a dibenzothiophenyl group, a dibenzofuranyl group, azacarbazole group, azafluorenyl group, azadibenzocylol group, azadibenzothiophenyl group, azadibenzofuranyl group, a pyrazol group, an imidazole group, a triazole group, a tetrazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a thiadiazole group, Includes benzopyrazol group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, imidazopyridinyl group, imidazopyrimidinyl group, imidazotriazinyl group, imidazopyrazinyl group, imidazopyridazinyl group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarbazole group, benzosilolocarbazole group, benzindolocarbazole group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, benzonaphthosilol group, benzofurodibenzofuranyl group, benzofurodibenzothiophenyl group, benzothienodibenzothiophenyl group, etc. In this specification, a divalent non-aromatic heterocondensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic heterocondensed polycyclic group.

[0472] C6-C in this specification 60 The aryloxy group is -OA 102 (Here, A 102 is the above C6-C 60 Pointing to arylgime), and the above C6-C 60The arylthio group is -SA 103 (Here, A 103 The above C6-C 60 It refers to the Arilgigiim).

[0473] "R" in this specification 10a "Is,

[0474] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group;

[0475] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ), or substituted or unsubstituted with any combination thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, or C1-C 60 Alkoxygenation;

[0476] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, -Si(Q 21)(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), or substituted or unsubstituted with any combination thereof, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, or C6-C 60 Arylthiogi; or

[0477] -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), or -P(=O)(Q 31 )(Q 32 );

[0478] It could be.

[0479] Q1 to Q3, Q in this specification 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 They are independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; or deuterium, -F, cyano group, C1-C 60 Alkyl group, C1-C 60 C3-C substituted or unsubstituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof60 Carbocyclic group or C1-C 60 It can be a heterocyclic group.

[0480] In this specification, a heteroatom refers to any atom other than a carbon atom. Examples of such heteroatoms include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

[0481] In this specification, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, and "ter-Bu" or "Bu t " represents the tert-butyl group, and "OMe" represents the methoxy group.

[0482] In this specification, "biphenyl group" means "phenyl group substituted with a phenyl group." The "biphenyl group" is a substituent of "C6-C 60 It belongs to the "substituted phenyl group" which is an "aryl group".

[0483] In this specification, "terphenyl group" means "phenyl group substituted with a biphenyl group." The "terphenyl group" is a substituent of "C6-C 60 C6-C substituted with aryl groups 60 It belongs to the "substituted phenyl group" which is an "aryl group".

[0484] In this specification, * and *' refer to bonding sites with adjacent atoms in the corresponding chemical formulas, unless otherwise defined.

[0485] [Example]

[0486] Synthesis Example 1: Synthesis of Ligand 1

[0487]

[0488] To 14.0 g of intermediate 1-A, 2.90 ml of dihydropyran (DHP), 1.20 ml of p-toluenesulfonic acid (TsOH), and 500 ml of CH2Cl2 were added to obtain 16.5 g of intermediate 1-B.

[0489] 14.5 g of potassium thioacetate (KSAc) was added to 16.5 g of the above intermediate 1-B under 500 ml of ethanol (EtOH) and refluxed to obtain 11 g of intermediate 1-C.

[0490] 8.00 g of TsOH was added to 11.0 g of the above intermediate 1-C under 500 ml of methanol (MeOH) and refluxed to obtain 12.5 g of intermediate 1-D.

[0491] To 14.0 g of intermediate 1-E, 11.0 g of dicyclohexylcarbodiimide (DCC), 2.70 g of dimethylaminopyridine (DMAP), and 10.0 ml of tetraethylene glycol dimethyl ether (TEGDME) were added, followed by the addition of 500 ml of CH2Cl2, and the mixture was stored at room temperature for 12 hours to obtain 17.0 g of intermediate 1-F.

[0492] To 17.0 g of the above intermediate 1-F, 10.0 g of DCC, 4.50 g of DMAP, and 12.5 g of the above intermediate 1-D were added, and 1000 ml of CH2Cl2 was added and stored at room temperature for 12 hours to obtain 14 g of the intermediate 1-G.

[0493] 250 ml of hydrazine was added to 14 g of the above intermediate 1-G to obtain 12 g of ligand 1. The NMR of ligand 1 is as follows:

[0494] 1 H NMR (500 MHz, CHCl3): δ 4.20-4.13 (m, 4H), 3.63-3.40 (m, 15H), 2.53 (d, 2H), 2.35 (t, 4H), 2.13 (m, 2H), 2.0 (t, 4H), 1.79 (s, 6H) 1.60-1.29 (m, 6H)

[0495] 13C NMR (125 MHz, CHCl3): δ173.1, 114.5, 71.6, 70.4, 70.1, 69.3, 66.9, 65.2, 56.5, 33.9, 30.5, 28.2, 25.2,24.6, 24.4, 23.9.

[0496] Synthesis Example 2: Synthesis of Ligand 2

[0497]

[0498] To 10 g of intermediate 1-A, 14.6 g of DCC, 6.00 ml of DMAP, and 7.00 ml of glutaric acid were added, followed by the addition of 500 ml of CH2Cl2. The mixture was stored at room temperature for 12 hours to obtain 10 g of ligand 2. The NMR of ligand 2 is as follows:

[0499] 1 H NMR (500 MHz, DMSO): δ12.01 (s, 1H), 7.94 (d, 4H), 6.99 (d, 4H), 4.42-4.45 (m, 4H)2.30-2.36 (m, 4H), 2.13 (m, 2H), 1.35 (s, 6H)

[0500] 13 C NMR (125 MHz, DMSO): δ198.6, 178.4, 66.8, 129.7, 129.4, 126.7, 81.3, 66.4, 62.3, 33.3, 32.7, 27.9, 19.7.

[0501] Synthesis Example 3: Preparation of Quantum Dot-Containing Material 1

[0502] 0.6 mmol and 0.31 g of the ligand obtained in Synthesis Example 1 were completely dissolved in 5 mL of chloroform, a solvent, and InP (1 st 1.5 g of Exciton peak: 460 nm) was added, and the mixture was reacted at room temperature for 0.5 hours under a nitrogen atmosphere to prepare a quantum dot-containing material in which ligand 1 was bound to the surface of InP quantum dots.

[0504] Synthesis Example 4: Preparation of Quantum Dot-Containing Material 2

[0505] 0.6 mmol and 0.2 g of the quantum dot-containing material obtained in Synthesis Example 2 were dissolved in 5 mL of chloroform, and InP (1 st 1.5 g of (Exciton peak: 460 nm) was added, and then reacted at 60°C for 0.5 hours under a nitrogen atmosphere to prepare a quantum dot-containing material in which ligand 2 is bound to the surface of InP quantum dots.

[0506] Synthesis Example 5: Preparation of Quantum Dot-Containing Material A

[0507] A quantum dot-containing material was prepared in the same manner as in Synthesis Example 3, except that the following ligand A was used instead of ligand 1.

[0508] <Ligand A>

[0509] Example 1: Preparation of quantum dot dispersion solution

[0510] 1.2 g of the quantum dot-containing material obtained in Synthesis Example 3 is dispersed in a mixed solution (monomer, dispersant, scatterer).

[0511] Example 2 and Comparative Example 1

[0512] A quantum dot dispersion solution was prepared in the same manner as in Example 1, except that the quantum dot-containing material obtained in Synthesis Examples 4 and 5 was used instead of the quantum dot-containing material obtained in Synthesis Example 3.

[0513] Evaluation Example 1: Quantum Efficiency Evaluation

[0514] The quantum efficiency (PCE) of solution samples containing the quantum dot-containing materials of Examples 1 and 2 and Comparative Example 1 was evaluated using a QE-2100 instrument, and the results are shown in FIGS. 5a and 5b and FIGS. 6a and 6b, respectively. (※ PCE = Photoconversion efficiency).

[0515] FIGS. 5a and 5b are graphs showing the change in PCE (%) before and after baking of thin films formed by quantum dot-containing materials according to Comparative Example 1 and Example 1, respectively, and FIGS. 6a and 6b are graphs showing the change in PCE (%) before and after exposure of thin films formed by quantum dot-containing materials according to Comparative Example 1 and Example 2, respectively.

[0516] Referring to FIGS. 5a to 5b and FIGS. 6a to 6b, it can be seen that the change in PCE before and after baking and before and after exposure during thin film formation is lower when ligand 1 or ligand 2 is used. Therefore, it can be seen that the quantum dot-containing material containing the ligand according to the present invention is more resistant to radical attack and has excellent stability. Explanation of the symbols

[0517] 1: Quantum dot-containing material 2: Quantum Dots 3: Ligand 4: Anchoring group 10: Light-emitting element 110: First electrode 150: Second electrode 130: Middle layer 131: Precision Transport Area 132: Emissive layer 133: Electronic Transport Area

Claims

Claim 1 Quantum dot; and a quantum dot-containing material comprising one or more ligands chemically bonded to the surface of the quantum dot and represented by the following chemical formula 1, wherein the quantum dot is a semiconductor nanoparticle, a core-shell structured particle comprising a core comprising a first semiconductor crystal and a shell comprising a second semiconductor crystal, or a perovskite compound: <Chemical Formula 1>R a -(Z1) a1 -(L1) b1 -(Z2) a2 -P1<Chemical Formula 2-1>*-N=N-(Z3) a3 -R1<Chemical Formula 2-2> In the above chemical formulas 1 and 2-1 to 2-2, R a is an anchoring group containing a moiety represented by -COOH, -PO3H, a dithiolane group, or -SH, and L1 is *-(CH2) n1 -*', or *-(O-CH2-CH2) n1 -O-*', b1 is selected from integers 1 to 5, P1 is a group represented by the above chemical formula 2-1 or 2-2, and Z1 to Z3 are independently *-O-*', *-C(=O)-*', *-C(=O)O-*', *-OC(=O)-*', *-OC(=O)-O-*', *-OCH2-*', *-SCH2-*', *-CH2S-*', *-CF2O-*', *-OCF2-*', *-CF2S-*', *-SCF2-*', *-(CH2) n1 -*', *-CF2CH2-*', *-CH2CF2-*', *-(CF2) n1 -*', *-C(CH3)CN-*', *-CH=CH-*', *-CF=CF-*', *-C≡C-*', *-CH=CH-C(=O)O-*', *-OC(=O)-CH=CH-*', *-C(Q1)(Q2)-*', and *-O-(CH2)-O(C=O)-(CH2) n2 Selected from -*', and at least one Z3 is *-O-*', *-C(=O)-*', *-C(=O)O-*', *-OC(=O)-*', *-OC(=O)-O-*', *-OCH2-*', *-SCH2-*', *-CH2S-*', *-CF2O-*', *-OCF2-*', *-CF2S-*', *-SCF2-*', *-CF2CH2-*', *-CH2CF2-*', *-(CF2) n1 -*', *-CH=CH-*', *-CF=CF-*', *-C≡C-*', *-CH=CH-C(=O)O-*', *-OC(=O)-CH=CH-*', *-C(Q1)(Q2)-*', and *-O-(CH2)-O(C=O)-(CH2) n2 Selected from -*', wherein Q1 and Q2 do not contain cyano groups, n1 is selected from integers 1 to 6, n2 is selected from integers 0 to 2, a1 to a3 are independently selected from integers 0 to 6, and R1 is *-(CH2) n3 -CH3, or *-(O-CH2-CH2) n1 -OH, n3 is selected from integers from 0 to 5, and Q1 and Q2 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazino group, hydrazono group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C1-C 60 Selected from heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic heterocondensed polycyclic groups, biphenyl groups and terphenyl groups, and * and *' are bonding sites with neighboring atoms. Claim 2 In paragraph 1, the above R a A quantum dot-containing material selected from the group represented by -COOH, -PO3H, -SH, or the following chemical formulas 3-1 to 3-4: In the above chemical formulas 3-1 to 3-4, * is a bonding site with an adjacent atom. Claim 3 In paragraph 1, the above Z1 is *-(CH2) n1 -*'Pheno, quantum dot-containing material. Claim 4 In paragraph 1, the above Z2 and Z3 are independently of each other, *-O-*', *-C(=O)O-*', *-OC(=O)-*', *-(CH2) n1 A quantum dot-containing material that is -*', or *-C(CH3)CN-*'. Claim 5 In paragraph 1, the above *-(Z2) a2 -*' and *-(Z3) a3 -*' are quantum dot-containing materials independently selected from the group represented by the following chemical formulas 4-1 to 4-4: In the above chemical formulas 4-1 to 4-4, * and *' are bonding sites with neighboring atoms. Claim 6 In claim 1, the ligand is a quantum dot-containing material represented by the following chemical formula 1A or 1B: <Chemical Formula 1A> <Chemical Formula 1B> Among the above chemical formulas 1A and 1B, R a For the description of , L1, b1 and R1, refer to the definition in Paragraph 1. Claim 7 In claim 1, the ligands are two or more, and the two or more ligands are identical or different quantum dot-containing materials. Claim 8 In claim 1, the ligand is a quantum dot-containing material that is chemically bonded to the surface of the quantum dot through an anchoring group. Claim 9 delete Claim 10 A quantum dot-containing material according to claim 1, wherein the semiconductor nanoparticles, the first semiconductor, and the second semiconductor independently comprise a group 10 compound, a group 11 compound, a group 12-16 compound, a group 13-15 compound, a group 14-16 compound, a group 14 compound, a group 11-13-16 compound, a group 11-12-13-16 compound, or any combination thereof. Claim 11 In claim 1, the semiconductor nanoparticles, the first semiconductor, and the second semiconductor are independently Au, Pd, Ag; CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgS, MgSe; CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnS, MgZnSe; CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe;GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb; GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP; GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb; Quantum dot-containing material comprising InZnP; SnS, SnSe, SnTe, PbS, PbSe, PbTe; SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe; SnPbSSe, SnPbSeTe, SnPbSTe; Si, Ge, SiC, SiGe; AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2; or any combination thereof. Claim 12 A quantum dot-containing material according to claim 1, wherein the average particle size (D50) of the quantum dots is 2 to 10 nm. Claim 13 Quantum dots; and a quantum dot-containing material chemically bonded to the surface of the quantum dots and comprising one or more ligands represented by the following compounds 1 or 2, wherein the quantum dots are semiconductor nanoparticles, core-shell structured particles comprising a core comprising a first semiconductor crystal and a shell comprising a second semiconductor crystal, or perovskite compounds: . Claim 14 A composition comprising a quantum dot-containing material according to any one of claims 1 to 8 and claims 10 to 13; and one or more solvents. Claim 15 A composition according to claim 14, further comprising a monomer comprising one or more double bonds. Claim 16 In Clause 14, the above composition is a composition that does not contain an initiator. Claim 17 An electronic device comprising a quantum dot-containing material according to any one of claims 1 through 8 and claims 10 through 13. Claim 18 In claim 17, the electronic device further comprises a light-emitting element including a first electrode; a second electrode opposite to the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode, wherein the quantum dot-containing material is included in the light-emitting layer. Claim 19 An electronic device according to claim 17, further comprising a light source, wherein the quantum dot-containing material is positioned in the path of light emitted from the light source. Claim 20 In paragraph 19, the above quantum dot-containing material is an electronic device included in a color conversion layer. Claim 21 An electronic device according to claim 19, wherein the light source is an organic light-emitting diode (OLED) or a light-emitting diode (LED).

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