Light-emitting element and nitrogen-containing compound

Abstract

Embodiments provide a nitrogen-containing compound and a light-emitting element. The light emitting element includes a first electrode, a second electrode facing the first electrode, and at least one functional layer disposed between the first electrode and the second electrode, in which the functional layer (e.g., an electron transport region) includes a nitrogen-containing compound. Nitrogen-containing compounds represented by Formula 1 explained in the description: [Formula 1] # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0075798 filed in the Korean Intellectual Property Office on June 13, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present disclosure relates to a light-emitting element, a nitrogen-containing compound used therein, and a display device including the same. Background Art

[0004] Organic electroluminescent display devices are being actively developed as image display devices. In contrast to liquid crystal display devices and the like, organic electroluminescent display devices are so-called self-luminescent display devices, in which holes and electrons injected from the first electrode and the second electrode are recombined in the emission layer, so that the light-emitting material including organic compounds in the emission layer emits light to achieve display.

[0005] When organic electroluminescent elements are applied to display devices, there is a demand for organic electroluminescent elements having high luminous efficiency and long element life, and there is a need to continuously develop materials for light-emitting elements that can stably achieve these characteristics.

[0006] In order to realize a light-emitting element having high luminous efficiency and long element life, development of materials for an electron transport region having excellent electron transport properties and stability is currently underway.

[0007] It should be understood that this background section of the technology section is intended to provide a useful background for understanding the technology. However, the background of the technology section may also include ideas, concepts or cognitions that were not known or understood by a person skilled in the relevant art before the corresponding effective filing date of the subject matter disclosed herein. Summary of the invention

[0008] The present disclosure provides a light-emitting element in which light-emitting efficiency and element life are improved.

[0009] The present disclosure also provides a nitrogen-containing compound capable of improving the luminous efficiency and service life of a light-emitting element.

[0010] The present disclosure also provides a display device including a light emitting element in which light emitting efficiency and element lifespan are improved.

[0011] An embodiment provides a light-emitting element, which may include a first electrode, a hole transport region disposed on the first electrode, an emission layer disposed on the hole transport region, an electron transport region disposed on the emission layer, and a second electrode disposed on the electron transport region, wherein the electron transport region may include a nitrogen-containing compound represented by Formula 1, and the emission layer may include an organic metal compound represented by Formula D-1:

[0012] [Formula 1]

[0013]

[0014] In Formula 1, Ar may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; L 1 and L 2 may be each independently directly linked or substituted or unsubstituted aryl having 6 to 30 ring carbon atoms; R 1 may be a group represented by Formula 2; and R 2 It may be a group represented by Formula 3-1, Formula 3-2 or Formula 3-3:

[0015] [Formula 2]

[0016]

[0017] In formula 2, X 1 To X 7 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, provided that X 1 or X 7 It may be a substituted or unsubstituted phenyl group; and *- is connected to L in Formula 1 1 Location:

[0018] [Formula 3-1]

[0019]

[0020] [Formula 3-2]

[0021]

[0022] [Formula 3-3]

[0023]

[0024] In formula 3-1, Y 1 and Y 2 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; in Formula 3-1 to Formula 3-3, R a1 To R a8 , R b1 To R b18 and R c1 To R c16 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; provided that when R in Formula 1 2 When it is a group represented by Formula 3-1, R in Formula 3-1 a1 To R a8 Any one of them can be connected to L in Formula 1 2 When R in Formula 1 2 When it is a group represented by formula 3-2, R in formula 3-2 b1 To R b18 Any one of them can be connected to L in Formula 1 2 position, and when R in Formula 1 2 When it is a group represented by formula 3-3, R in formula 3-3 c1 To R c16 Any one of them can be connected to L in Formula 1 2 location.

[0025] [Formula D-1]

[0026]

[0027] In formula D-1, Q 1 To Q 4 may be each independently C or N; C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms; L 11 To L 13 Can be directly connected, *-O-*, *-S-*, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, in which L 11 To L 13 In the formula (a), -* represents a bond connected to one of C1 to C4; b1 to b3 may each independently be 0 or 1; R 61 To R 66 Each of d1 to d4 may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, or may be bonded to an adjacent group to form a ring; and d1 to d4 may be independently an integer selected from 0 to 4.

[0028] In an embodiment, the electron transport region may include an electron transport layer disposed on the emission layer and an electron injection layer disposed on the electron transport layer; and the electron transport layer may include the nitrogen-containing compound represented by Formula 1.

[0029] In an embodiment, L 1 may be directly linked or substituted or unsubstituted phenyl; and L 2 Can be a direct connection.

[0030] In an embodiment, Ar may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

[0031] In an embodiment, the nitrogen-containing compound represented by Formula 1 may be represented by any one of Formula 1-1 to Formula 1-4:

[0032] [Formula 1-1]

[0033]

[0034] [Formula 1-2]

[0035]

[0036] [Formula 1-3]

[0037]

[0038] [Formula 1-4]

[0039]

[0040] In Formula 1-1 to Formula 1-4, X 11 To X 18 can each independently be a hydrogen atom or a deuterium atom; n1, n3, n5 and n7 can each independently be an integer selected from 0 to 5; n2, n4, n6 and n8 can each independently be an integer selected from 0 to 6; and Ar, L 2 and R 2 Same as defined in Formula 1.

[0041] In an embodiment, X 11 To X 18 Each may be a hydrogen atom.

[0042] In an embodiment, the nitrogen-containing compound represented by Formula 1 may be represented by any one of Formulas 1-5 to 1-9:

[0043] [Formula 1-5]

[0044]

[0045] [Formula 1-6]

[0046]

[0047] [Formula 1-7]

[0048]

[0049] [Formula 1-8]

[0050]

[0051] [Formula 1-9]

[0052]

[0053] In Formula 1-5 to Formula 1-9, R x1 To R x14 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms; m1 and m2 may each independently be an integer selected from 0 to 7; m3 to m5, m9, m11, m13, and m14 may each independently be an integer selected from 0 to 4; m6 and m10 may each independently be an integer selected from 0 to 3; m7, m8, and m12 may each independently be an integer selected from 0 to 5; and Ar, L 1 and R 1 Same as defined in Formula 1.

[0054] In an embodiment, R x1 To R x3 and Rx5 To R x14 may each be a hydrogen atom; and R x4 It may be a hydrogen atom or an unsubstituted phenyl group.

[0055] In an embodiment, the nitrogen-containing compound represented by Formula 1 may be represented by any one of Formulas 1-10 to 1-14:

[0056] [Formula 1-10]

[0057]

[0058] [Formula 1-11]

[0059]

[0060] [Formula 1-12]

[0061]

[0062] [Formula 1-13]

[0063]

[0064] [Formula 1-14]

[0065]

[0066] In Formula 1-10 to Formula 1-14, Ar, L 1 and R 1 Same as defined in Formula 1.

[0067] In an embodiment, the nitrogen-containing compound represented by Formula 1 may include at least one compound selected from Compound Group 1 explained below.

[0068] The emission layer may further include a compound represented by Formula Fc explained below in an embodiment.

[0069] Embodiments provide nitrogen-containing compounds, which may be represented by Formula 1 explained herein.

[0070] In an embodiment, L 1 may be directly linked or substituted or unsubstituted phenyl; and L 2 Can be a direct connection.

[0071] In an embodiment, Ar may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

[0072] In an embodiment, the nitrogen-containing compound represented by Formula 1 may be represented by any one of Formula 1-1 to Formula 1-4 explained herein.

[0073] In an embodiment, the nitrogen-containing compound represented by Formula 1 may be represented by any one of Formula 1-5 to Formula 1-9 explained herein.

[0074] In an embodiment, the nitrogen-containing compound represented by Formula 1 may be represented by any one of Formulas 1-10 to 1-14 explained herein.

[0075] In an embodiment, the nitrogen-containing compound represented by Formula 1 may be selected from Compound Group 1 explained below.

[0076] Embodiments provide a display device, which may include a circuit layer disposed on a substrate layer, and a display device layer disposed on the circuit layer and including a light-emitting element. The light-emitting element may include a first electrode, a second electrode disposed on the first electrode, and an electron transport region disposed between the first electrode and the second electrode; and the electron transport region may include a nitrogen-containing compound represented by Formula 1 explained herein.

[0077] It should be understood that the above embodiments have been described in a general and illustrative sense only and not for limiting purposes, and the present disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS

[0078] The attached drawings are included to provide a further understanding of the embodiments and are incorporated into and constitute a part of this specification. The drawings illustrate the embodiments of the present disclosure and its principles. The above and other aspects and features of the present disclosure will become more apparent by describing the embodiments of the present disclosure in detail with reference to the attached drawings, in which:

[0079] Figure 1 is a schematic plan view of a display device according to an embodiment;

[0080] Figure 2 is a schematic cross-sectional view of a display device according to an embodiment;

[0081] Figure 3 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0082] Figure 4 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0083] Figure 5 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0084] Figure 6 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0085] Figure 7 is a schematic cross-sectional view of a display device according to an embodiment;

[0086] Figure 8 is a schematic cross-sectional view of a display device according to an embodiment;

[0087] Fig. 9 is a schematic cross-sectional view of a display device according to an embodiment;

[0088] Fig.10 is a schematic cross-sectional view of a display device according to an embodiment; and

[0089] Fig.11 is a schematic perspective view of a vehicle in which a display device is provided according to an embodiment. DETAILED DESCRIPTION

[0090] The present disclosure will now be described more fully below with reference to the accompanying drawings, in which embodiments are shown. However, the present disclosure may be implemented in different forms and should not be construed as being limited to the embodiments set forth herein. Instead, these embodiments are provided to make the present disclosure thorough and complete and to fully convey the scope of the present disclosure to those skilled in the art.

[0091] In the drawings, the sizes, ratios, and dimensions (eg, thickness) of elements may be exaggerated for ease of description and clarity. Like reference numerals and reference characters refer to like elements throughout.

[0092] In the specification, it should be understood that when an element (or region, layer, portion, etc.) is referred to as being "on" another element (or region, layer, portion, etc.), "connected to" or "coupled to" another element (or region, layer, portion, etc.), it can be directly on, directly connected to or coupled to the other element (or region, layer, portion, etc.), or one or more intervening elements (or regions, layers, portions, etc.) may be present therebetween. In a similar sense, when an element (or region, layer, portion, etc.) is described as "covering" another element (or region, layer, portion, etc.), it can directly cover the other element (or region, layer, portion, etc.), or one or more intervening elements (or regions, layers, portions, etc.) may be present therebetween.

[0093] In the specification, when an element is "directly on," "directly connected to," or "directly coupled to" another element, there are no intervening elements. For example, "directly on" may mean that two layers or two elements are disposed without additional elements (such as adhesive elements in between).

[0094] As used herein, expressions used in the singular such as “a”, “an” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0095] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. For example, "A and / or B" may be understood to mean "A, B, or A and B". The terms "and" and "or" may be used in a conjunctive or disjunctive sense and may be understood to be equivalent to "and / or".

[0096] In the specification and claims, the term "at least one of" is intended to include the meaning of "at least one selected from the group consisting of" for the purposes of its meaning and interpretation. For example, "at least one of A, B, and C" may be understood to mean only A, only B, only C, or any combination of two or more of A, B, and C, such as ABC, ACC, BC, or CC. When following a list of elements, the term "at least one of" modifies the entire list of elements and does not modify the individual elements of the list.

[0097] It should be understood that although the terms first, second, etc. can be used to describe various elements in this article, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Therefore, without departing from the teaching of the present disclosure, the first element can be referred to as the second element. Similarly, the second element can be referred to as the first element without departing from the scope of the present disclosure.

[0098] For ease of description, spatially relative terms such as "below", "under", "lower", "above", or "on" may be used herein to describe the relationship between one element or component and another element or component, as shown in the accompanying drawings. It should be understood that in addition to the orientation depicted in the accompanying drawings, the spatially relative terms are intended to cover different orientations of the device in use or operation. For example, in the case where the device shown in the drawings is turned over, a device located "below" or "below" another device can be placed "above" the other device. Therefore, the illustrative term "below" can include both lower and upper positions. The device may also be oriented in other directions, so the spatially relative terms may be interpreted differently depending on the orientation.

[0099] As used herein, the terms "about" or "approximately" include the stated value and mean within an acceptable range of deviation of the stated value as determined by one of ordinary skill in the art, taking into account the measurement in question and the errors associated with the measurement of the stated quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the stated value.

[0100] It should be understood that the terms “comprises,” “comprising,” “includes,” “including,” “have,” “having,” “contain,” and “containing” and the like are intended to specify the presence of specified features, integers, steps, operations, elements, components, or a combination thereof in the present disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or a combination thereof.

[0101] Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as those commonly understood by those skilled in the art to which the present disclosure belongs. It should also be understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the relevant art, and should not be interpreted in an ideal or overly formal sense unless clearly defined in the specification.

[0102] In the specification, the term "substituted or unsubstituted" can describe a group substituted or unsubstituted by at least one substituent selected from the group consisting of: deuterium atoms, halogen atoms, cyano groups, nitro groups, amino groups, amido groups, silyl groups, oxy groups, sulfenyl groups, sulfinyl groups, sulfonyl groups, carbonyl groups, boron groups, phosphine oxide groups, phosphine sulfide groups, alkyl groups, alkenyl groups, alkynyl groups, hydrocarbon ring groups, aryl groups and heterocyclic groups. Each of the substituents listed above can itself be substituted or unsubstituted. For example, biphenyl groups can be interpreted as aryl groups or can be interpreted as phenyl groups substituted by phenyl groups.

[0103] In the specification, the term "bonded to an adjacent group to form a ring" may be interpreted as a group bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring may be aliphatic or aromatic. The heterocyclic ring may be aliphatic or aromatic. The hydrocarbon ring and the heterocyclic ring may each independently be a monocyclic or polycyclic ring. The ring formed by the adjacent groups bonding to each other may itself be connected to another ring to form a spiro structure.

[0104] In the specification, the term "adjacent group" may be interpreted as a substituent of a substituted atom, which is directly connected to the atom substituted by the corresponding substituent, as another substituent of a substituted atom (which is substituted by the corresponding substituent), or as a substituent at a position closest to the corresponding substituent in space. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane may be interpreted as "adjacent groups" to each other. For example, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups" to each other.

[0105] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0106] In the specification, the alkyl group may be linear or branched. The number of carbon atoms in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, alkyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heonicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like, but the embodiment is not limited thereto.

[0107] In the specification, the cycloalkyl group may be a cyclic alkyl group. The number of carbon atoms in the cycloalkyl group may be 3 to 50, 3 to 30, 3 to 20, or 3 to 10. Examples of the cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl, bicycloheptyl, etc., but the embodiment is not limited thereto.

[0108] In the specification, the alkenyl group may be a hydrocarbon group including at least one carbon-carbon double bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. The alkenyl group may be linear or branched. The number of carbon atoms in the alkenyl group is not particularly limited, and may be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups may include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, styrylvinyl, etc., but embodiments are not limited thereto.

[0109] In the specification, the alkynyl group may be a hydrocarbon group including at least one carbon-carbon triple bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. The alkynyl group may be linear or branched. The number of carbon atoms in the alkynyl group is not particularly limited, and may be 2 to 30, 2 to 20, or 2 to 10. Examples of the alkynyl group may include ethynyl, propynyl, etc., but embodiments are not limited thereto.

[0110] In the specification, the hydrocarbon ring group may be any functional group or substituent derived from an aliphatic hydrocarbon ring. For example, the hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 ring-forming carbon atoms.

[0111] In the specification, the aryl group may be any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be monocyclic or polycyclic. The number of ring carbon atoms in the aryl group may be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, triphenylene, pyrenyl, benzofluoranthenyl, 1,2-triphenylenyl, etc., but embodiments are not limited thereto.

[0112] In the specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of the substituted fluorenyl group may include the groups shown below. However, the embodiment is not limited thereto.

[0113]

[0114] In the specification, the heterocyclic group may be any functional group or substituent derived from a ring including at least one of B, O, N, P, Si, S and Se as a heteroatom. The heterocyclic group may be aliphatic or aromatic. The aromatic heterocyclic group may be a heteroaryl. The aliphatic heterocycle and the aromatic heterocycle may each independently be monocyclic or polycyclic.

[0115] In the specification, the heterocyclic group may include at least one of B, O, N, P, Si, S and Se as a heteroatom. If the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be monocyclic or polycyclic, and the heterocyclic group may be a heteroaryl. The number of ring-forming carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10.

[0116] In the specification, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si, S and Se as a heteroatom. The number of ring-forming carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10. Examples of the aliphatic heterocyclic group may include an oxirane group, an oxirane group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, a thiol group, a tetrahydropyranyl group, a 1,4-dioxanyl group and the like, but the embodiment is not limited thereto.

[0117] In the specification, the heteroaryl group may include at least one of B, O, N, P, Si, S and Se as a heteroatom. If the heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be monocyclic or polycyclic. The number of ring carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20 or 2 to 10. Examples of heteroaryl groups may include thienyl, furanyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazine, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzothirolyl, dibenzofuranyl, and the like, but embodiments are not limited thereto.

[0118] In the specification, the above description of the aryl group may be applied to the arylene group, except that the arylene group is a divalent group. In the specification, the above description of the heteroaryl group may be applied to the heteroarylene group, except that the heteroarylene group is a divalent group.

[0119] In the specification, the silyl group may be an alkylsilyl group or an arylsilyl group. The alkyl group in the alkylsilyl group may be linear, branched or cyclic. The number of carbon atoms in the alkylsilyl group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylsilyl group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of silyl groups may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but embodiments are not limited thereto.

[0120] In the specification, the number of carbon atoms in the carbonyl group is not particularly limited, and may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have one of the following structures, but the embodiment is not limited thereto.

[0121]

[0122] In the specification, the number of carbon atoms in the sulfinyl group or the sulfonyl group is not particularly limited, and may be 1 to 30. The sulfinyl group may be an alkylsulfinyl group or an arylsulfinyl group. The sulfonyl group may be an alkylsulfonyl group or an arylsulfonyl group.

[0123] In the specification, the thio group may be an alkylthio group or an arylthio group. The thio group may be a sulfur atom bonded to an alkyl group or an aryl group as defined above. The alkyl group in the alkylthio group may be linear, branched or cyclic. The number of carbon atoms in the alkylthio group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylthio group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of thio groups may include methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, naphthylthio, etc., but embodiments are not limited thereto.

[0124] In the specification, the oxy group may be an oxygen atom bonded to an alkyl group or an aryl group as defined above. The oxy group may be an alkoxy group or an aryloxy group. The alkoxy group may be linear, branched or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, and may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the aryloxy group is not limited, but the number of ring carbon atoms may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of oxy groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc., but embodiments are not limited thereto.

[0125] In the specification, the boryl group may be a boron atom bonded to an alkyl group or an aryl group as defined above. The boryl group may be an alkyl boryl group or an aryl boryl group. The alkyl group in the alkyl boryl group may be linear, branched or cyclic. The number of carbon atoms in the alkyl boryl group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the aryl boryl group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of the boryl group may include dimethyl boryl, diethyl boryl, tert-butyl methyl boryl, diphenyl boryl, phenyl boryl, etc., but the embodiment is not limited thereto.

[0126] In the specification, the amine group may be an alkylamine group or an arylamine group. The alkyl group in the alkylamine group may be linear, branched or cyclic. The number of carbon atoms in the alkylamine group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylamine group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of the amine group may include methylamine, dimethylamine, phenylamine, diphenylamine, naphthylamine, 9-methyl-anthrylamine, etc., but the embodiment is not limited thereto.

[0127] In the specification, the phosphine oxide group may mean an alkyl group or an aryl group defined above combined with -P(=O)-. The number of carbon atoms of the phosphine oxide group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphine oxide group may include an alkyl phosphine oxide group and an aryl phosphine oxide group. For example, the phosphine oxide group may have the following structure, but is not limited thereto.

[0128]

[0129] In the specification, the phosphinosulfide group may mean an alkyl group or an aryl group defined above combined with -P(=S)-. The number of carbon atoms of the phosphinosulfide group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphinosulfide group may include an alkylphosphinosulfide group and an arylphosphinosulfide group. For example, the phosphinosulfide group may have the following structure, but is not limited thereto.

[0130]

[0131] In the specification, the alkyl group in the alkoxy group, the alkylthio group, the alkylsulfonyl group, the alkylaryl group, the alkylamino group, the alkylboryl group, the alkylsilyl group or the alkylamine group may be the same as the examples of the alkyl group described above.

[0132] In the specification, the aryl group in the aryloxy group, the arylthio group, the arylsulfonyl group, the arylamino group, the arylboryl group, the arylsilyl group or the arylamine group may be the same as exemplified in the above-mentioned aryl group.

[0133] In the specification, a direct connection may be a single bond.

[0134] In this manual, the symbol Each represents a bond connecting adjacent atoms in the corresponding formula or moiety.

[0135] Hereinafter, embodiments will be described with reference to the accompanying drawings.

[0136] Figure 1 is a schematic plan view of a display device DD according to an embodiment. Figure 2 is a schematic cross-sectional view of a display device DD according to an embodiment. Figure 2 To explain along Figure 1 Schematic cross-sectional view of a portion taken along line II' in FIG.

[0137] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP includes light emitting elements ED-1, ED-2, and ED-3. The display device DD may include a plurality of light emitting elements ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP to control light reflected at the display panel DP by external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. Although not shown in the drawings, in an embodiment, the optical layer PP may be omitted from the display device DD.

[0138] The base substrate BL may be disposed on the optical layer PP. The base substrate BL may provide a base surface on which the optical layer PP is disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, or the like. However, the embodiment is not limited thereto, and the base substrate BL may include an inorganic layer, an organic layer, or a composite material layer. Although not shown in the drawings, the base substrate BL may be omitted in the embodiment.

[0139] The display device DD according to the embodiment may further include a filling layer (not shown). The filling layer (not shown) may be provided between the display device layer DP-ED and the base substrate BL. The filling layer (not shown) may be an organic material layer. The filling layer (not shown) may include at least one of an acrylic resin, a silicone resin, and an epoxy resin.

[0140] The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED. The display device layer DP-ED may include a pixel defining film PDL, light emitting elements ED-1, ED-2, and ED-3 disposed between the pixel defining films PDL, and an encapsulation layer TFE disposed on the light emitting elements ED-1, ED-2, and ED-3.

[0141] The base layer BS may provide a base surface on which the display device layer DP-ED is disposed. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited thereto, and the base layer BS may include an inorganic layer, an organic layer, or a composite material layer.

[0142] In an embodiment, the circuit layer DP-CL is disposed on the base layer BS, and the circuit layer DP-CL may include transistors (not shown). The transistors (not shown) may each include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include a switching transistor and a driving transistor for driving the light emitting elements ED-1, ED-2, and ED-3 of the display device layer DP-ED.

[0143] The light emitting elements ED-1, ED-2 and ED-3 may each have Figures 3 to 6 The structure of the light-emitting element ED of any one embodiment of the present invention will be described later. The light-emitting elements ED-1, ED-2, and ED-3 may each include a first electrode EL1, a hole transport region HTR, emission layers EML-R, EML-G, and EML-B, an electron transport region ETR, and a second electrode EL2.

[0144] Figure 2An embodiment is explained in which the emission layers EML-R, EML-G and EML-B of the light emitting elements ED-1, ED-2 and ED-3 are disposed in the opening OH defined by the pixel defining film PDL, and the hole transport region HTR, the electron transport region ETR and the second electrode EL2 are each provided as a common layer for the light emitting elements ED-1, ED-2 and ED-3. However, the embodiment is not limited thereto. Although not described in Figure 2 , but in an embodiment, the hole transport region HTR and the electron transport region ETR may each be provided by patterning in the opening OH defined by the pixel definition film PDL. For example, in an embodiment, the hole transport region HTR, the emission layers EML-R, EML-G and EML-B, and the electron transport region ETR of the light emitting elements ED-1, ED-2 and ED-3 may each be provided by patterning by an inkjet printing method.

[0145] The encapsulation layer TFE may cover the light emitting elements ED-1, ED-2 and ED-3. The encapsulation layer TFE may seal the light emitting elements ED-1, ED-2 and ED-3 in the display device layer DP-ED. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be formed of a single layer or multiple layers. The encapsulation layer TFE may include at least one insulating layer. The encapsulation layer TFE according to an embodiment may include at least one inorganic film (hereinafter, encapsulation-inorganic film). In an embodiment, the encapsulation layer TFE may include at least one organic film (hereinafter, encapsulation-organic film) and at least one encapsulation-inorganic film.

[0146] The encapsulation-inorganic film protects the display device layer DP-ED from moisture and / or oxygen, and the encapsulation-organic film protects the display device layer DP-ED from foreign substances such as dust particles. The encapsulation-inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, or aluminum oxide, etc., but the embodiment is not limited thereto. The encapsulation-organic film may include an acrylic compound or an epoxy compound, etc. The encapsulation-organic film may include a photopolymerizable organic material, but the embodiment is not limited thereto.

[0147] The encapsulation layer TFE may be disposed on the second electrode EL2 and may be disposed to fill the opening OH.

[0148] See also Figure 1 and Figure 2 , the display device DD may include a non-light emitting area NPXA and light emitting areas PXA-R, PXA-G, and PXA-B. The light emitting areas PXA-R, PXA-G, and PXA-B may each be an area emitting light generated by the light emitting elements ED-1, ED-2, and ED-3, respectively. The light emitting areas PXA-R, PXA-G, and PXA-B may be separated from each other in a plan view.

[0149] The light-emitting areas PXA-R, PXA-G, and PXA-B may be areas separated from each other by a pixel-defining film PDL. The non-light-emitting area NPXA may be an area between adjacent light-emitting areas PXA-R, PXA-G, and PXA-B, and it may correspond to the pixel-defining film PDL. In an embodiment, the light-emitting areas PXA-R, PXA-G, and PXA-B may each correspond to a pixel. The pixel-defining film PDL may separate the light-emitting elements ED-1, ED-2, and ED-3. The emission layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 may be disposed in the opening OH defined by the pixel-defining film PDL and separated from each other.

[0150] The light emitting areas PXA-R, PXA-G, and PXA-B may be arranged into a plurality of groups according to the colors of the lights generated from the light emitting elements ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In the display device DD according to the embodiment explained in , three light emitting areas PXA-R, PXA-G and PXA-B emitting red light, green light and blue light respectively are explained as examples. For example, the display device DD may include a red light emitting area PXA-R, a green light emitting area PXA-G and a blue light emitting area PXA-B which are different from each other.

[0151] In the display device DD according to the embodiment, the light emitting elements ED-1, ED-2 and ED-3 may emit light having different wavelengths from each other. For example, in the embodiment, the display device DD may include a first light emitting element ED-1 emitting red light, a second light emitting element ED-2 emitting green light, and a third light emitting element ED-3 emitting blue light. For example, the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B of the display device DD may correspond to the first light emitting element ED-1, the second light emitting element ED-2, and the third light emitting element ED-3, respectively.

[0152] However, the embodiment is not limited thereto, and the first to third light emitting elements ED-1, ED-2, and ED-3 may emit light in the same wavelength range, or at least one light emitting element may emit light in a wavelength range different from that of the remaining light emitting elements. For example, the first to third light emitting elements ED-1, ED-2, and ED-3 may each emit blue light.

[0153] The light emitting regions PXA-R, PXA-G, and PXA-B in the display device DD according to the embodiment may be arranged in a stripe configuration. Figure 1, the red light emitting area PXA-R, the green light emitting area PXA-G and the blue light emitting area PXA-B may be arranged along the second direction axis DR2, respectively. In another embodiment, the red light emitting area PXA-R, the green light emitting area PXA-G and the blue light emitting area PXA-B may be arranged in this repeating order along the first direction axis DR1.

[0154] Figure 1 and Figure 2 It is explained that the light-emitting regions PXA-R, PXA-G, and PXA-B all have the same area, but the embodiment is not limited thereto. In an embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B may have sizes or shapes different from each other according to the wavelength range of the emitted light. The areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be areas in a plane view defined by the first direction axis DR1 and the second direction axis DR2. The third direction axis DR3 may be perpendicular to the plane defined by the first direction axis DR1 and the second direction axis DR2.

[0155] The arrangement of the light emitting areas PXA-R, PXA-G and PXA-B is not limited to Figure 1 The configuration explained in , and the order in which the red light emitting area PXA-R, the green light emitting area PXA-G and the blue light emitting area PXA-B are arranged can be provided in various combinations according to the display quality characteristics required by the display device DD. For example, the light emitting areas PXA-R, PXA-G and PXA-B can be arranged in a honeycomb configuration (such as ) or diamond configuration (such as Diamond ) in the form of.

[0156] The areas of the light emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in an embodiment, the area of ​​the green light emitting region PXA-G may be smaller than the area of ​​the blue light emitting region PXA-B, but the embodiment is not limited thereto.

[0157] In the following, Figures 3 to 6 Each is a schematic cross-sectional view of a light-emitting element according to an embodiment. The embodiment provides a light-emitting element ED, which may include a first electrode EL1, a second electrode EL2 disposed on the first electrode EL1, and at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The light-emitting element ED may include a nitrogen-containing compound represented by Formula 1 according to an embodiment to be described below in at least one functional layer (e.g., an electron transport region ETR). In an embodiment, the light-emitting element ED may include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2.

[0158] and Figure 3 compared to, Figure 4Schematic cross-sectional view of a light emitting element ED according to an embodiment, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 3 compared to, Figure 5 Schematic cross-sectional view of a light emitting element ED according to an embodiment, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL and a hole blocking layer HBL. Figure 4 compared to, Figure 6 1 is a schematic cross-sectional view of a light emitting element ED according to an embodiment, and includes a capping layer CPL disposed on the second electrode EL2 .

[0159] The first electrode EL1 has conductivity. The first electrode EL1 may be formed of a metal material, a metal alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the embodiment is not limited thereto. In an embodiment, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. The first electrode EL1 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, an oxide thereof, a compound thereof, or a mixture thereof.

[0160] If the first electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). If the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, and W, a compound thereof, or a mixture thereof (e.g., a mixture of Ag and Mg), or a multilayer structure material such as LiF / Ca (a stacking structure of LiF and Ca) or LiF / Al (a stacking structure of LiF and Al). In another embodiment, the first electrode EL1 may have a multilayer structure including a reflective film or a transflective film formed of the above materials and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the embodiment is not limited thereto. In an embodiment, the first electrode EL1 may include the above metal material, a combination of at least two of the above metal materials, or an oxide of the above metal materials. The thickness of the first electrode EL1 may be about 1000 nm. to about For example, the thickness of the first electrode EL1 may be about to about within the range.

[0161] The hole transport region HTR may be provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a buffer layer (not shown), an emission auxiliary layer (not shown), and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 1000 Å. to about within the range.

[0162] The hole transport region HTR may be a single-layer structure composed of a single material, a single-layer structure including different materials, or a structure including a multi-layer including different materials.

[0163] In an embodiment, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or may have a single-layer structure formed of a hole injection material and a hole transport material. In an embodiment, the hole transport region HTR may have a single-layer structure formed of different materials, or may have a structure in which a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / buffer layer (not shown), a hole injection layer HIL / buffer layer (not shown), a hole transport layer HTL / buffer layer (not shown), or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked in their respective prescribed orders from the first electrode EL1, but the embodiment is not limited thereto.

[0164] The hole transport region HTR may be formed using various methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Brokett (LB) method, an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method.

[0165] In the light emitting element ED according to the embodiment, the hole transport region HTR may include a compound represented by Formula H-1:

[0166] [Formula H-1]

[0167]

[0168] In formula H-1, L 1 and L 2 Each of L is independently a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In formula H-1, a and b are independently an integer selected from 0 to 10. When a or b is 2 or more, multiple L 1 Group or multiple L 2The groups may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0169] In formula H-1, Ar 1 and Ar 2 and Ar may be each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 3 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0170] In an embodiment, the compound represented by formula H-1 may be a monoamine compound. In another embodiment, the compound represented by formula H-1 may be a compound wherein Ar 1 To Ar 3 In another embodiment, the compound represented by formula H-1 may be a diamine compound wherein Ar 1 and Ar 2 At least one of the carbazole compounds includes a substituted or unsubstituted carbazole group, or may be a carbazole compound in which Ar 1 and Ar 2 At least one of the fluorene compounds includes a substituted or unsubstituted fluorenyl group.

[0171] The compound represented by Formula H-1 may be any compound selected from Compound Group H. However, the compounds listed in Compound Group H are only examples, and the compound represented by Formula H-1 is not limited to Compound Group H:

[0172] [Compound Group H]

[0173]

[0174] The hole transport region HTR may include a phthalocyanine compound such as copper phthalocyanine, N 1 ,N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4-dimethylphenylbenzene-1,4-diamine) (DNTPD), 4,4',4"-[tri(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tri(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tri[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (P ANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(1-naphthyl)-N,N'-diphenyl-benzidine (NPB), triphenylamine polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate], dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), etc.

[0175] The hole transport region HTR may include carbazole derivatives such as N-phenylcarbazole or polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4',4"-tri(carbazol-9-yl)triphenylamine (TCTA), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD) or 1,3-bis(N-carbazyl)benzene (mCP), etc.

[0176] The hole transport region HTR may include 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9′-bicarbazole (CCP), 1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene (mDCP), or the like.

[0177] The hole transport region HTR may include the above-mentioned compound of the hole transport region HTR in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

[0178] The thickness of the hole transport region HTR can be to about For example, the thickness of the hole transport region HTR may be in the range of about to about When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have a thickness of about to about When the hole transport region HTR includes the hole transport layer HTL, the hole transport layer HTL may have a thickness of about to about When the hole transport region HTR includes the electron blocking layer EBL, the electron blocking layer EBL may have a thickness of about to about If the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above ranges, satisfactory hole transport properties may be achieved without a significant increase in driving voltage.

[0179] In addition to the above materials, the hole transport region HTR may further include a charge generation material to increase conductivity. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generation material may be, for example, a p-dopant. The p-dopant may include at least one of a metal halide, a quinone derivative, a metal oxide, and a cyano compound, but the embodiment is not limited thereto.

[0180] For example, the p-dopant may include a metal halide such as CuI or RbI; a quinone derivative such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ); a metal oxide such as tungsten oxide or molybdenum oxide; a cyano compound such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9), etc., but the embodiment is not limited thereto.

[0181] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a buffer layer (not shown) and an electron blocking layer EBL. The buffer layer (not shown) may compensate for the resonance distance according to the wavelength of light emitted from the emission layer EML, and thus may increase the light emission efficiency. The material that may be included in the hole transport region HTR may be used as a material in the buffer layer (not shown). The electron blocking layer EBL may prevent the injection of electrons from the electron transport region ETR to the hole transport region HTR.

[0182] The emission layer EML may be provided on the hole transport region HTR. The emission layer EML may have a thickness of about to about For example, the emission layer EML may have a thickness of about to about The emission layer EML may be a single-layer structure composed of a single material, a single-layer structure including different materials, or a structure including a multi-layer including different materials.

[0183] In the light emitting element ED, the emission layer EML may include an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a 1,2-triphenylene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. For example, the emission layer EML may include an anthracene derivative or a pyrene derivative.

[0184] In such Figures 3 to 6 In the light emitting element ED according to the embodiment shown in , the emission layer EML may include a host and a dopant.

[0185] In an embodiment, the emission layer EML may include a first compound represented by one of Formulas Fa to Fc. The compound represented by one of Formulas Fa to Fc may be used as a fluorescent dopant material. For example, the compound represented by Formula Fc may be used as a fluorescent dopant material in the emission layer EML.

[0186] [Formula]

[0187]

[0188] In formula Fa, R a To R j The two of them can be independently represented by *-NAr 1 Ar 2 The group represented by R is substituted. a To R j Not by *-NAr 1 Ar 2 The remaining groups substituted by the groups represented may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms.

[0189] In *-NAr 1 Ar 2 In the group represented by 1 and Ar 2 and Ar may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 and Ar 2 At least one of them may each independently be a heteroaryl group including O or S as a ring-forming atom.

[0190] [Formula Fb]

[0191]

[0192] In formula Fb, R a and R b Each of Ar and Ar may be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, or may be bonded to an adjacent group to form a ring. 1 To Ar 4 and Ar may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To Ar 4 At least one of them may each independently be a heteroaryl group including O or S as a ring-forming atom.

[0193] In Formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring group of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group of 2 to 30 ring carbon atoms.

[0194] In formula Fb, the number of rings represented by U and V may be 0 or 1 independently of each other. If the number of U or V is 1, a condensed ring may be present in the portion indicated by U or V, and if the number of U or V is 0, a condensed ring may not be present in the portion indicated by U or V. If the number of U is 0 and the number of V is 1, or if the number of U is 1 and the number of V is 0, the condensed ring of the fluorene core of formula Fb may be a cyclic compound having four rings. If the number of U and V is each 0, the condensed ring of the fluorene core of formula Fb may be a cyclic compound having three rings. If the number of U and V is each 1, the condensed ring of the fluorene core of formula Fb may be a cyclic compound having five rings.

[0195] [Formula Fc]

[0196]

[0197] In Formula Fc, A 1 and A 2 can be independently O, S, Se or N (R m ); and R mIt may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms. 1 To R 11 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may be bonded to an adjacent group to form a ring.

[0198] In Formula Fc, A 1 and A 2 Each of A and B may independently combine with the substituents of adjacent rings to form a fused ring. 1 and A 2 Each independently is N(R m ), then A 1 Can be used with R 4 or R 5 bond to form a ring. For example, A 2 Can be used with R 7 or R 8 bonded to form a ring.

[0199] In an embodiment, the emission layer EML may include a compound represented by Formula E-1. The compound represented by Formula E-1 may be used as a fluorescent host material.

[0200] [Formula E-1]

[0201]

[0202] In formula E-1, R 31 To R 40 Each of R and R may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or may be bonded to an adjacent group to form a ring. For example, R 31 To R 40 At least one of the groups may combine with an adjacent group to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring, or an unsaturated heterocyclic ring.

[0203] In Formula E-1, c and d may be an integer selected from 0 to 5, each independently.

[0204] In an embodiment, the compound represented by Formula E-1 may be any compound selected from Compound E1 to Compound E19:

[0205]

[0206]

[0207] In an embodiment, the emission layer EML may include: a first compound represented by one of Formulas Fa to Fc; and at least one of a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula D-1.

[0208] In an embodiment, the emission layer EML may further include a second compound represented by Formula HT-1. In an embodiment, the second compound may be used as a hole transport host material in the emission layer EML.

[0209] [Formula HT-1]

[0210]

[0211] In formula HT-1, A 1 To A 8 can be N or C (R 51 ). For example, A 1 To A 8 can be independently C(R 51 As another example, A 1 To A 8 One of can be N, and A 1 To A 8 The remaining groups in may be independently C(R 51 ).

[0212] In formula HT-1, L 1 It may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 1 It may be a direct connection, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted divalent carbazole group, etc., but the embodiment is not limited thereto.

[0213] In formula HT-1, Y a Can be directly connected, C(R 52 )(R 53 ) or Si(R 54 )(R 55). For example, the two aromatic rings bonded to the nitrogen atom of formula HT-1 can be connected directly, directly connected to each other. In formula HT-1, if Y a For direct attachment, the second compound represented by formula HT-1 may include a carbazole moiety.

[0214] In formula HT-1, Ar 1 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 The group may be a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted biphenyl group, but the embodiment is not limited thereto.

[0215] In formula HT-1, R 51 To R 55 Each of R and R may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, or may be bonded to an adjacent group to form a ring. For example, R 51 To R 55 can each independently be a hydrogen atom or a deuterium atom. 51 To R 55 Each independently may be an unsubstituted methyl group or an unsubstituted phenyl group.

[0216] In an embodiment, the second compound represented by Formula HT-1 may be selected from Compound Group 2. In an embodiment, in the light emitting element ED, the second compound may include at least one compound selected from Compound Group 2:

[0217] [Compound Group 2]

[0218]

[0219]

[0220]

[0222]

[0223] In compound group 2, D represents a deuterium atom, and Ph represents a substituted or unsubstituted phenyl group. For example, in compound group 2, Ph may represent an unsubstituted phenyl group.

[0224] In an embodiment, the emission layer EML may further include a third compound represented by Formula ET-1. In an embodiment, the third compound may be used as an electron transport host material in the emission layer EML.

[0225] [Formula ET-1]

[0226]

[0227] In formula ET-1, X 1 To X 3 At least one of them may each be N, and X 1 To X 3 The remaining groups in may be independently C(R 56 ). For example, X 1 To X 3 One of can be N, and X 1 To X 3 The remaining groups in may be independently C(R 56 ). Therefore, the third compound represented by Formula ET-1 may include a pyridine moiety. As another example, X 1 To X 3 Two of them can be N, and X 1 To X 3 The remaining groups in may be C(R 56 ). Therefore, the third compound represented by Formula ET-1 may include a pyrimidine moiety. As another example, X 1 To X 3 Each may be N. Therefore, the third compound represented by Formula ET-1 may include a triazine moiety.

[0228] In formula ET-1, R 56 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms.

[0229] In Formula ET-1, b1 to b3 may each independently be an integer selected from 0 to 10.

[0230] In formula ET-1, Ar 2 To Ar 4and R and R are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms. 2 To Ar 4 Each independently may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazolyl group.

[0231] In formula ET-1, L 2 To L 4 Each of L and L is independently a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 2 To L 4 A plurality of groups of each of the groups may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0232] In an embodiment, the third compound represented by Formula ET-1 may be selected from Compound Group 3. In an embodiment, in the light emitting element ED, the third compound may include at least one compound selected from Compound Group 3:

[0233] [Compound Group 3]

[0234]

[0235]

[0236]

[0237]

[0238] In compound group 3, D represents a deuterium atom, and Ph represents an unsubstituted phenyl group.

[0239] In an embodiment, the emission layer EML may include a second compound and a third compound, and the second compound and the third compound may form an exciplex. In the emission layer EML, the exciplex may be formed by a hole transport host and an electron transport host. The triplet energy level of the exciplex formed by the hole transport host and the electron transport host may correspond to the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the electron transport host and the highest occupied molecular orbital (HOMO) energy level of the hole transport host.

[0240] For example, the absolute value of the triplet energy level (T1 level) of the excited complex formed by the hole transport host and the electron transport host may be in the range of about 2.4 eV to about 3.0 eV. The triplet energy level of the excited complex may have a value less than the energy gap of each host material. The excited complex may have a triplet energy level equal to or less than about 3.0 eV, which is the energy gap between the hole transport host and the electron transport host.

[0241] In an embodiment, the emission layer EML may include a fourth compound in addition to the first compound, the second compound, and the third compound. The fourth compound may serve as a sensitizer in the emission layer EML. Energy may be transferred from the fourth compound to the first compound, thereby emitting light.

[0242] The emission layer EML may include an organic metal complex as a fourth compound, the organic metal complex including platinum (Pt) as a central metal atom and a ligand bonded to the central metal atom. In an embodiment, the emission layer EML may further include a fourth compound represented by Formula D-1. In the specification, the fourth compound may be referred to as an "organic metal compound".

[0243] [Formula D-1]

[0244]

[0245] In formula D-1, Q 1 To Q 4 They may each independently be C or N.

[0246] In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms.

[0247] In formula D-1, L 11 To L 13 Can be directly connected, *-O-*, *-S-*, A substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 11 To L 13 In the formula (a), -* indicates a bond connected to one of C1 to C4.

[0248] In formula D-1, b1 to b3 may each independently be 0 or 1. If b1 is 0, C1 and C2 may not be directly connected to each other. If b2 is 0, C2 and C3 may not be directly connected to each other. If b3 is 0, C3 and C4 may not be directly connected to each other.

[0249] In formula D-1, R 61 To R 66 Each of R and R may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, or may be bonded to an adjacent group to form a ring. For example, R 61 To R 66 Each independently may be a substituted or unsubstituted methyl group or a substituted or unsubstituted tert-butyl group.

[0250] In Formula D-1, d1 to d4 may each independently be an integer selected from 0 to 4. In Formula D-1, if d1 to d4 are each 0, the fourth compound may be respectively not R 61 To R 64 wherein d1 to d4 are each 4 and R 61 To R 64 The case where all groups of each of are hydrogen atoms may be the same as the case where d1 to d4 are each 0. If d1 to d4 are each 2 or more, then R 61 To R 64 The multiple groups of each of may all be the same, or at least one of them may be different from the remaining groups.

[0251] In an embodiment, in Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group or a substituted or unsubstituted heterocyclic group represented by one of Formulas C-1 to C-4:

[0252]

[0253] In Formula C-1 to Formula C-4, P 1 Can be C-* or C(R 74 ), P 2 Can be N-* or N(R 81 ), P 3 Can be N-* or N(R 82 ), and P 4 Can be C-* or C(R 88 ).

[0254] In Formula C-1 to Formula C-4, R 71 To R 88Each may be independently a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, or may bond with an adjacent group to form a ring.

[0255] In Formula C-1 to Formula C-4, represents a bond to Pt, and -* represents a bond to an adjacent ring group (C1 to C4) or a linker (L 11 To L 13 ) key to connect.

[0256] In an embodiment, the emission layer EML may include: a first compound which is a condensed polycyclic compound; and at least one of a second compound, a third compound, and a fourth compound. In an embodiment, the emission layer EML may include the first compound, the second compound, and the third compound. In the emission layer EML, the second compound and the third compound may form an exciplex, and energy may be transferred from the exciplex to the first compound, thereby emitting light.

[0257] In another embodiment, the emission layer EML may include a first compound, a second compound, a third compound, and a fourth compound. In the emission layer EML, the second compound and the third compound may form an exciplex, and energy may be transferred from the exciplex to the fourth compound and the first compound, thereby emitting light. In an embodiment, the fourth compound may be a sensitizer. In the light-emitting element ED, the fourth compound included in the emission layer EML may be used as a sensitizer for transferring energy from the host to the first compound as a light-emitting dopant. For example, the fourth compound used as a sensitizer may accelerate the energy transfer to the first compound used as a light-emitting dopant, thereby increasing the emission ratio of the first compound. Accordingly, the emission layer EML may exhibit improved luminous efficiency. If the energy transfer to the first compound increases, the excitons formed in the emission layer EML may not accumulate and may emit light quickly, so that the degradation of the light-emitting element ED may be reduced. Accordingly, the element service life of the light-emitting element ED may be increased.

[0258] The light emitting element ED may include a first compound, a second compound, a third compound, and a fourth compound, and the emission layer EML may include a combination of two host materials and two dopant materials. In the light emitting element ED, the emission layer EML may include a second compound and a third compound that are two different hosts, a first compound that emits delayed fluorescence, and a fourth compound that is an organic metal complex, so that the light emitting element ED can exhibit excellent luminous efficiency properties.

[0259] In an embodiment, the fourth compound represented by Formula D-1 may be selected from Compound Group 4. In an embodiment, in the light emitting element ED, the fourth compound may include at least one compound selected from Compound Group 4:

[0260] [Compound Group 4]

[0261]

[0262]

[0263] In compound group 4, D represents a deuterium atom.

[0264] In the light-emitting element ED, if the emission layer EML includes a first compound, a second compound, and a third compound, the amount of the first compound may be in the range of about 0.1 wt % to about 5 wt % based on the total weight of the first compound, the second compound, and the third compound. However, the embodiment is not limited thereto. If the amount of the first compound satisfies the above range, the energy transfer from the second compound and the third compound to the first compound may be increased, and accordingly, the luminous efficiency and the element service life may be increased.

[0265] In the emission layer EML, the combined amount of the second compound and the third compound may be the remainder of the total weight of the first compound, the second compound, and the third compound excluding the weight of the first compound. For example, in the emission layer EML, the combined amount of the second compound and the third compound may be in the range of about 65 wt % to about 99 wt % based on the total weight of the first compound, the second compound, and the third compound.

[0266] Within the combined amount of the second compound and the third compound in the emission layer EML, a weight ratio of the second compound to the third compound may be in the range of about 3:7 to about 7:3.

[0267] If the amount of the second compound and the third compound satisfies the above range and ratio, the charge balance property in the emission layer EML can be improved, and the luminous efficiency and the service life of the element can be increased. If the amount of the second compound and the third compound deviates from the above range and ratio, the charge balance in the emission layer EML cannot be achieved, so that the luminous efficiency is reduced, and the light-emitting element is easily degraded.

[0268] If the emission layer EML includes a fourth compound, the amount of the fourth compound in the emission layer EML may be in the range of about 4 wt % to about 30 wt % based on the total weight of the first compound, the second compound, the third compound, and the fourth compound. However, the embodiment is not limited thereto. If the amount of the fourth compound satisfies the above range, the energy transfer from the host to the first compound as a light-emitting dopant may increase, so that the emission ratio may increase. Accordingly, the luminous efficiency of the emission layer EML may be improved. If the amounts of the first compound, the second compound, the third compound, and the fourth compound included in the emission layer EML satisfy the above range and ratio, excellent luminous efficiency and long element life may be achieved.

[0269] In an embodiment, the emission layer EML may include a compound represented by Formula E-2a or Formula E-2b. The compound represented by Formula E-2a or Formula E-2b may be used as a phosphorescent host material.

[0270] [Formula E-2a]

[0271]

[0272] In Formula E-2a, a may be an integer selected from 0 to 10; and L a It may be a directly linked, substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms. If a is 2 or more, then multiple L a The groups may each independently be a substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms.

[0273] In formula E-2a, A 1 To A 5 can be N or C (R i ). In Formula E-2a, R a To R i Each of them may be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, or may be bonded to an adjacent group to form a ring. For example, R a To R i Each of may combine with an adjacent group to form a hydrocarbon ring or a heterocyclic ring including N, O, S, etc. as a ring-constituting atom.

[0274] In formula E-2a, A 1 To A 5Two or three of them can each be N, and A 1 To A 5 The remaining groups in may be independently C(R i ).

[0275] [Formula E-2b]

[0276]

[0277] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazole group or a carbazole group substituted with an aromatic group having 6 to 30 ring carbon atoms. b It may be a directly linked, substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms. In Formula E-2b, b may be an integer selected from 0 to 10. If b is 2 or greater, then the plurality of L b The groups may each independently be a substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms.

[0278] The compound represented by Formula E-2a or Formula E-2b may be any compound selected from Compound Group E-2. However, the compounds listed in Compound Group E-2 are only examples, and the compound represented by Formula E-2a or Formula E-2b is not limited to Compound Group E-2:

[0279] [Compound Group E-2]

[0280]

[0281] The emission layer EML may further include a related art material as a host material. For example, the emission layer EML may include at least one of bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazyl)-1,1'-biphenyl (CBP), 1,3-bis(N-carbazyl)benzene (mCP), 2,8-bis(diphenylphosphino)dibenzo[b,d]furan (PPF), 4,4',4"-tri(carbazol-9-yl)triphenylamine (TCTA), and 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) as a host material. However, embodiments are not limited thereto. For example, tris(8-hydroxyquinoline)aluminum (Alq 3)、9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyrylarene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH 2 ), hexaphenylcyclotrisiloxane (DPSiO 3 ), octaphenylcyclotetrasiloxane (DPSiO 4 ) etc. can be used as the main material.

[0282] In an embodiment, the emission layer EML may include a compound represented by Formula Ma. The compound represented by Formula Ma may be used as a phosphorescent dopant material.

[0283] [Formula]

[0284]

[0285] In formula Ma, Y 1 To Y 4 and Z 1 To Z 4 can be independently C(R 1 ) or N; and R 1 To R 4 Each independently may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted sulfenyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, or bonded to an adjacent group to form a ring. In formula Ma, m may be 0 or 1, and n may be 2 or 3. In formula Ma, if m is 0, n may be 3, and if m is 1, n may be 2.

[0286] The compound represented by formula Ma may be any compound selected from compound M-a1 to compound M-a25. However, compound M-a1 to compound M-a25 are only examples, and the compound represented by formula Ma is not limited to compound M-a1 to compound M-a25:

[0287]

[0288]

[0289] In an embodiment, the emission layer EML may include styryl derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi) and 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), perylene or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene or its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene and 1,4-bis(N,N-diphenylamino)pyrene), etc. as dopant materials in the prior art.

[0290] The emission layer EML may include a phosphorescent dopant material of the prior art. For example, the phosphorescent dopant may use a metal complex including iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm). For example, bis(4,6-difluorophenylpyridyl-N,C2') picolinyl iridium (III) (FIrpic), bis(2,4-difluorophenylpyridyl)-tetrakis(1-pyrazolyl) borate iridium (III) (FIrpic), 6 ) or platinum octaethylporphyrin (PtOEP) may be used as the phosphorescent dopant. However, the embodiment is not limited thereto.

[0291] In an embodiment, the emission layer EML may include a quantum dot material. The quantum dot may be a II-VI group compound, a III-VI group compound, an I-III-VI group compound, a III-V group compound, a III-II-V group compound, a IV-VI group compound, a IV group element, a IV group compound, or any combination thereof.

[0292] Examples of Group II-VI compounds may include: binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; ternary compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, C dZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and mixtures thereof; or any combination thereof.

[0293] Examples of Group III-VI compounds may include: binary compounds such as In 2 S 3 andIn 2 Se 3 ; Ternary compounds, such as InGaS 3 and InGaSe 3 ; or any combination thereof.

[0294] Examples of Group I-III-VI compounds may include: ternary compounds selected from the group consisting of: AgInS, AgInS 2 、CuInS、CuInS 2 、AgGaS 2 、CuGaS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 and mixtures thereof; quaternary compounds, such as AgInGaS 2 、CuInGaS 2 and mixtures thereof; or any combination thereof.

[0295] Examples of Group III-V compounds may include: a binary compound selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; a ternary compound selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; a quaternary compound selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof; or any combination thereof. In an embodiment, the Group III-V compound may further include a Group II metal. Examples of the Group III-II-V compound may include InZnP and the like.

[0296] Examples of Group IV-VI compounds may include: binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and mixtures thereof; quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe and mixtures thereof; or any combination thereof.

[0297] Examples of Group IV elements may include Si, Ge, and mixtures thereof. Examples of Group IV compounds may include binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0298] Each element included in a multi-element compound such as a binary compound, a ternary compound, or a quaternary compound may be present in the particle at a uniform concentration or a non-uniform concentration. For example, a chemical formula may indicate the elements included in the compound, but the ratio of the elements in the compound may vary. For example, AgInGaS 2 Can mean AgIn x Ga 1-x S 2 (where x is a real number between 0 and 1).

[0299] In an embodiment, the quantum dot may have a single structure in which the concentration of each element included in the quantum dot is uniform, or the quantum dot may have a core-shell structure. For example, the material included in the core and the material included in the shell may be different from each other.

[0300] The shell of the quantum dot can be used as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties and / or can be used as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient, wherein the concentration of the element present in the shell decreases toward the center of the core.

[0301] In an embodiment, the quantum dot may have the above core-shell structure including a core and a shell surrounding the core, the core including nanocrystals. Examples of the shell of the quantum dot may include metal oxides, non-metal oxides, semiconductor compounds, or any combination thereof.

[0302] Examples of metal oxides or non-metal oxides may include binary compounds such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 and NiO; or ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 and CoMn 2 O 4 However, the embodiment is not limited thereto.

[0303] Examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but embodiments are not limited thereto.

[0304] The quantum dots may have a full width at half maximum (FWHM) of an emission spectrum equal to or less than about 45 nm. For example, the quantum dots may have a FWHM of an emission spectrum equal to or less than about 40 nm. For example, the quantum dots may have a FWHM of an emission wavelength spectrum equal to or less than about 30 nm. Within any of the above ranges, color purity or color reproducibility may be improved. Light emitted by the quantum dots may be emitted in all directions, so that the light viewing angle properties may be improved.

[0305] The shape of the quantum dot can be any shape used in the prior art. For example, the quantum dot can have a spherical shape, a pyramidal shape, a multi-arm shape or a cubic shape, or the quantum dot can be in the form of nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc.

[0306] By controlling the size of the quantum dots or by controlling the ratio of elements in the quantum dots, the energy band gap can be controlled, and light of various wavelength bands can be obtained from the quantum dot emission layer. Accordingly, by using quantum dots (e.g., using quantum dots with different sizes or controlling the ratio of elements in the quantum dot compound), a light-emitting element that emits light of various wavelength bands can be realized. For example, the size of the quantum dots or the ratio of elements in the quantum dot compound can be adjusted to emit red light, green light, and / or blue light. For example, quantum dots can be configured to emit white light by combining light of various colors.

[0307] In such Figures 3 to 6 In each of the light emitting elements ED according to the embodiments shown in , an electron transport region ETR may be provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the embodiment is not limited thereto.

[0308] The electron transport region ETR may be a single-layer structure composed of a single material, a single-layer structure including different materials, or a structure including multiple layers including different materials.

[0309] For example, the electron transport region ETR may have a single-layer structure of an electron injection layer EIL or an electron transport layer ETL, or may have a single-layer structure formed of an electron injection material and an electron transport material. In other embodiments, the electron transport region ETR may have a single-layer structure formed of different materials, or may have a structure in which an electron transport layer ETL / electron injection layer EIL or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL are stacked from the emission layer EML in their respective prescribed orders, but the embodiment is not limited thereto. The electron transport region ETR may have, for example, a structure of about to about The thickness is within the range of .

[0310] The electron transport region ETR may be formed by using various methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Brokett (LB) method, an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method.

[0311] The light emitting element ED according to the embodiment may include the nitrogen-containing compound represented by Formula 1 in at least one functional layer (e.g., electron transport region ETR) disposed between the first electrode EL1 and the second electrode EL2. In the light emitting element ED, the electron transport region ETR may include the nitrogen-containing compound represented by Formula 1 according to the embodiment. In the embodiment, the electron transport region ETR may include an electron transport layer ETL, and the electron transport layer ETL may include the nitrogen-containing compound represented by Formula 1 according to the embodiment.

[0312] The nitrogen-containing compound represented by Formula 1 according to an embodiment includes a triazine ring, and a first substituent and a second substituent each connected to a carbon atom of the triazine ring. The first substituent and the second substituent are each connected to a carbon atom of the triazine ring via an arylene linker or a heteroarylene linker, or directly connected to a carbon atom of the triazine ring without a linker.

[0313] The first substituent may include a naphthalene moiety and a benzene moiety connected to the naphthalene moiety. In the first substituent, the carbon at the position-2 of the naphthalene moiety may be connected to the triazine ring, and the carbon at the position-1 or the carbon at the position-3 may be connected to the benzene moiety. For example, in the naphthalene moiety of the first substituent, the benzene moiety and the triazine ring may be connected to each other at the ortho position. The numbered positions of the carbon atoms of the naphthalene moiety constituting the first substituent are represented by formula S1:

[0314] [Formula S1]

[0315]

[0316] The second substituent includes a fluorene moiety. The fluorene moiety of the second substituent may be a structure substituted by a methyl group or a phenyl group. In an embodiment, the fluorene moiety of the second substituent may be a structure substituted by two phenyl groups, and the two substituted phenyl groups may be directly bonded to each other to form a spiro structure. Examples of substituted fluorene groups are as follows. However, embodiments are not limited thereto.

[0317]

[0318] In the second substituent, a carbon atom of the aromatic ring in the fluorene moiety may be connected to the triazine ring. In an embodiment, when the second substituent includes a fluorene moiety substituted with a phenyl group, the aromatic ring of the phenyl group may be connected to the triazine ring.

[0319] Since the first substituent and the second substituent are introduced, the nitrogen-containing compound represented by Formula 1 according to the embodiment may have excellent electrical stability and high charge transport capability. Accordingly, the light-emitting element according to the embodiment including the nitrogen-containing compound represented by Formula 1 may have improved luminous efficiency and improved element life.

[0320] The nitrogen-containing compound according to an embodiment may be represented by Formula 1:

[0321] [Formula 1]

[0322]

[0323] In Formula 1, Ar may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. In an embodiment, Ar may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

[0324] In formula 1, L 1 and L 2 L may be independently directly linked or substituted or unsubstituted aryl having 6 to 30 ring carbon atoms. 1 may be directly linked or substituted or unsubstituted phenyl, and L 2 Can be a direct connection.

[0325] In formula 1, R 1 may be a group represented by Formula 2, and R 2 It may be a group represented by Formula 3-1, Formula 3-2 or Formula 3-3.

[0326] [Formula 2]

[0327]

[0328] In formula 2, X 1 To X 7 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, provided that X 1 or X 7 It can be a substituted or unsubstituted phenyl group. For example, X 1 may be unsubstituted phenyl, and X2 To X 7 X may be independently a hydrogen atom or a deuterium atom. 7 may be unsubstituted phenyl, and X 1 To X 6 They may each independently be a hydrogen atom or a deuterium atom.

[0329] In Formula 2, *- is connected to L in Formula 1 1 location.

[0330] [Formula 3-1]

[0331]

[0332] [Formula 3-2]

[0333]

[0334] [Formula 3-3]

[0335]

[0336] In formula 3-1, Y 1 and Y 2 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. 1 and Y 2 Each independently may be a substituted or unsubstituted methyl group.

[0337] In Formula 3-1 to Formula 3-3, R a1 To R a8 , R b1 To R b18 and R c1 To R c16 Each of R and R may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, R a1 To R a8 , R b1 To R b18 and R c1 To R c16 They may each independently be a hydrogen atom, a deuterium atom or a substituted or unsubstituted phenyl group.

[0338] Formula 3-1 to Formula 3-3 include additional conditions. When R in Formula 1 2 When it is a group represented by Formula 3-1, R in Formula 3-1 a1 To R a8 Any one of them can be connected to L in Formula 1 2 When R in Formula 1 2 When it is a group represented by formula 3-2, R in formula 3-2 b1 To R b18 Any one of them can be connected to L in Formula 1 2 position, and when R in Formula 1 2 When it is a group represented by formula 3-3, R in formula 3-3 c1 To R c16 Any one of them can be connected to L in Formula 1 2 location.

[0339] Formula 1 includes a triazine ring as described above. Formula 2 may correspond to the naphthalene portion of the first substituent as described above. In Formula 2, the naphthalene moiety connected to X 1 or X 7 The substituted or unsubstituted phenyl group may correspond to the benzene portion of the first substituent as described above. Formula 3-1, Formula 3-2, and Formula 3-3 may each correspond to the fluorene portion as described above.

[0340] In an embodiment, the nitrogen-containing compound represented by Formula 1 may be represented by any one of Formula 1-1 to Formula 1-4:

[0341] [Formula 1-1]

[0342]

[0343] [Formula 1-2]

[0344]

[0345] [Formula 1-3]

[0346]

[0347] [Formula 1-4]

[0348]

[0349] Formula 1-1 to Formula 1-4 each represent wherein L is further defined in Formula 1 1 and R 1 Formula 1-1 and Formula 1-2 each represent a case where L 1 is the case of direct connection, and Formula 1-3 and Formula 1-4 each represent that L 1Formula 1-1 and Formula 1-3 each represent a case where X in Formula 2 is 1 is a substituted or unsubstituted phenyl group, and Formula 1-2 and Formula 1-4 each represent a case in which X in Formula 2 7 In the case of substituted or unsubstituted phenyl.

[0350] In Formula 1-1 to Formula 1-4, X 11 To X 18 can each independently be a hydrogen atom or a deuterium atom. In an embodiment, X 11 To X 18 Each may be a hydrogen atom.

[0351] In Formula 1-1 to Formula 1-4, n1, n3, n5, and n7 may each independently be an integer selected from 0 to 5. If n1, n3, n5, and n7 are each 0, the nitrogen-containing compound represented by Formula 1 may not be respectively 11 , X 13 , X 15 and X 17 Where n1, n3, n5 and n7 are each 5 and X 11 , X 13 , X 15 and X 17 The case where all groups of each of are hydrogen atoms may be the same as the case where n1, n3, n5 and n7 are each 0. If n1, n3, n5 and n7 are each 2 or more, then X 11 , X 13 , X 15 and X 17 The multiple groups of each of may all be the same, or at least one of them may be different from the remaining groups.

[0352] In Formula 1-1 to Formula 1-4, n2, n4, n6, and n8 may each independently be an integer selected from 0 to 6. If n2, n4, n6, and n8 are each 0, the nitrogen-containing compound represented by Formula 1 may not be respectively 12 , X 14 , X 16 and X 18 wherein n2, n4, n6 and n8 are each 6 and X 12 , X 14 , X 16 and X 18 The case where all groups of each of are hydrogen atoms may be the same as the case where n2, n4, n6 and n8 are each 0. If n2, n4, n6 and n8 are each 2 or greater, then X 12 , X 14 , X 16 and X 18The multiple groups of each of may all be the same, or at least one of them may be different from the remaining groups.

[0353] In Formula 1-1 to Formula 1-4, Ar, L 2 and R 2 Same as described in Formula 1.

[0354] In an embodiment, the nitrogen-containing compound represented by Formula 1 may be represented by any one of Formulas 1-5 to 1-9: [Formula 1-5]

[0355]

[0357] [Formula 1-6]

[0358]

[0359] [Formula 1-7]

[0360]

[0361] [Formula 1-8]

[0362]

[0363] [Formula 1-9]

[0364]

[0365] In Formula 1-5 to Formula 1-9, R x1 To R x14 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms. x1 To R x3 and R x5 To R x14 may each be a hydrogen atom, and R x4 It may be a hydrogen atom or an unsubstituted phenyl group.

[0366] In Formula 1-5 and Formula 1-6, m1 and m2 may each independently be an integer selected from 0 to 7. If m1 and m2 are each 0, the nitrogen-containing compound represented by Formula 1 may not be R x1 and R x2 Wherein m1 and m2 are each 7 and all R x1 Groups and all R x2 The case where all the groups are hydrogen atoms may be the same as the case where m1 and m2 are each 0. If m1 and m2 are each 2 or more, then the plurality of R x1 Groups and multiple R x2The groups may all be identical, or at least one of them may be different from the rest.

[0367] In Formulae 1-7 to 1-9, m3 to m5, m9, m11, m13, and m14 may each independently be an integer selected from 0 to 4. If m3 to m5, m9, m11, m13, and m14 are each 0, the nitrogen-containing compound represented by Formula 1 may not be R x3 To R x5 , R x9 , R x11 , R x13 and R x14 wherein m3 to m5, m9, m11, m13 and m14 are each 4 and R x3 To R x5 , R x9 , R x11 , R x13 and R x14 The case where all groups of each of are hydrogen atoms may be the same as the case where m3 to m5, m9, m11, m13 and m14 are each 0. If m3 to m5, m9, m11, m13 and m14 are each 2 or more, then R x3 To R x5 , R x9 , R x11 , R x13 and R x14 The multiple groups of each of may all be the same, or at least one of them may be different from the remaining groups.

[0368] In Formula 1-7 and Formula 1-8, m6 and m10 may each independently be an integer selected from 0 to 3. If m6 and m10 are each 0, the nitrogen-containing compound represented by Formula 1 may not be R x6 and R x10 Where m6 and m10 are each 3 and all R x6 Groups and all R x10 The case where all the groups are hydrogen atoms may be the same as the case where m6 and m10 are each 0. If m6 and m10 are each 2 or greater, then the plurality of R x6 Groups and multiple R x10 The groups may all be identical, or at least one of them may be different from the rest.

[0369] In Formula 1-8 and Formula 1-9, m7, m8, and m12 may each independently be an integer selected from 0 to 5. If m7, m8, and m12 are each 0, the nitrogen-containing compound represented by Formula 1 may not be R x7 , R x8 and R x12 Wherein m7, m8 and m12 are each 5 and all Rx7 Group, all R x8 Groups and all R x12 The case where all the groups are hydrogen atoms may be the same as the case where m7, m8 and m12 are each 0. If m7, m8 and m12 are each 2 or greater, then the plurality of R x7 Group, multiple R x8 Groups and multiple R x12 The groups may all be identical, or at least one of them may be different from the rest.

[0370] In Formula 1-5 to Formula 1-9, Ar, L 1 and R 1 Same as described in Formula 1.

[0371] In an embodiment, the nitrogen-containing compound represented by Formula 1 may be represented by any one of Formulas 1-10 to 1-14:

[0372] [Formula 1-10]

[0373]

[0374] [Formula 1-11]

[0375]

[0376] [Formula 1-12]

[0377]

[0378] [Formula 1-13]

[0379]

[0380] [Formula 1-14]

[0381]

[0382] In Formula 1-10 to Formula 1-14, Ar, L 1 and R 1 Same as described in Formula 1.

[0383] In an embodiment, the nitrogen-containing compound represented by Formula 1 may be any compound selected from compound group 1. In an embodiment, in the light emitting element ED, at least one functional layer (eg, electron transport region ETR) may include at least one nitrogen-containing compound selected from compound group 1:

[0384] [Compound Group 1]

[0385]

[0386]

[0387]

[0388]

[0389]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398] The nitrogen-containing compound represented by Formula 1 according to the embodiment may include a triazine ring, and a first substituent and a second substituent each connected to the triazine ring. The first substituent may include a phenylnaphthalene portion, and the second substituent may include a fluorene portion. By having such a structure, the nitrogen-containing compound represented by Formula 1 according to the embodiment may therefore have improved material stability and a high glass transition temperature, thereby preventing crystallization. The light-emitting element ED according to the embodiment includes the nitrogen-containing compound represented by Formula 1 according to the embodiment, and thus, thermal stability and chemical stability are improved, thereby showing improved element characteristics. Satisfactory charge transfer characteristics can be achieved without significantly increasing the driving voltage, so that increased luminous efficiency can be achieved.

[0399] In the light emitting element ED according to the embodiment, the electron transport region ETR may further include a compound represented by Formula ET-2:

[0400] [Formula ET-2]

[0401]

[0402] In formula ET-2, X 1 To X 3 At least one of them can be N, and X 1 To X 3The remaining groups in may be independently C(R a ). In formula ET-2, R a It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To Ar 3 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0403] In Formula ET-2, a to c may each independently be an integer selected from 0 to 10. In Formula ET-2, L 1 To L 3 Each of L and L is independently a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 1 To L 3 A plurality of groups of each of may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0404] The electron transport region ETR may include an anthracene compound. However, the embodiment is not limited thereto. The electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq 3 ), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl 1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole ( t Bu-PBD), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB) or a mixture thereof.

[0405] In an embodiment, the electron transport region ETR may include at least one compound selected from compound ET1 to compound ET36:

[0406]

[0407]

[0408] In an embodiment, the electron transport region ETR may include: a metal halide such as LiF, NaCl, CsF, RbCl, RbI, CuI or KI; a lanthanide metal such as Yb; or a co-deposited material of a metal halide and a lanthanide metal. For example, the electron transport region ETR may include KI:Yb, RbI:Yb, LiF:Yb, etc. as a co-deposited material. The electron transport region ETR may include a metal oxide such as Li 2 O or BaO, or 8-hydroxy-quinoline lithium (Liq), etc., but the embodiment is not limited thereto. The electron transport region ETR may also be formed of a mixture material of an electron transport material and an insulating organic metal salt. The insulating organic metal salt may be a material with an energy band gap equal to or greater than about 4 eV. For example, the insulating organic metal salt may include a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate, or a metal stearate.

[0409] In addition to the above materials, the electron transport region ETR may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and 4,7-diphenyl-1,10-phenanthroline (Bphen), but the embodiment is not limited thereto.

[0410] The electron transport region ETR may include the above-mentioned compound of the electron transport region ETR in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

[0411] When the electron transport region ETR includes the electron transport layer ETL, the electron transport layer ETL may have a thickness of about to about For example, the electron transport layer ETL may have a thickness of about to about If the thickness of the electron transport layer ETL satisfies any of the aforementioned ranges, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage. When the electron transport region ETR includes the electron injection layer EIL, the electron injection layer EIL may have a thickness of about to about For example, the electron injection layer EIL may have a thickness of about to about If the thickness of the electron injection layer EIL satisfies any of the above ranges, satisfactory electron injection characteristics may be obtained without significantly increasing the driving voltage.

[0412] The second electrode EL2 may be provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the embodiment is not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode. The second electrode may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, an oxide thereof, a compound thereof, or a mixture thereof.

[0413] The second electrode EL2 may be a transmissive electrode, a transflective electrode or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may be formed of a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.

[0414] When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb and W, a compound thereof, or a mixture thereof (e.g., AgMg, AgYb or MgYb), or a multilayer structure material such as LiF / Ca (a stacked structure of LiF and Ca) or LiF / Al (a stacked structure of LiF and Al). In an embodiment, the second electrode EL2 may have a multilayer structure including a reflective film or a transflective film formed of the above materials and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may include the above metal materials, a combination of at least two of the above metal materials, or an oxide of the above metal materials, etc.

[0415] Although not shown in the drawings, the second electrode EL2 may be electrically connected to the auxiliary electrode. If the second electrode EL2 is electrically connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0416] In an embodiment, the light emitting element ED may further include a capping layer CPL disposed on the second electrode EL2. The capping layer CPL may be a multi-layer or a single layer.

[0417] In an embodiment, the capping layer CPL may include an organic layer and / or an inorganic layer. For example, when the capping layer CPL includes an inorganic material, the inorganic material may include an alkali metal compound (eg, LiF), an alkaline earth metal compound (eg, MgF 2 )、SiON、SiN x 、SiO y wait.

[0418] For example, when the capping layer CPL includes an organic material, the organic material may include N,N'-bis(1-naphthyl)-N,N'-bis(phenyl)-2,2'-dimethylbenzidine (α-NPD), NPB, TPD, m-MTDATA, Alq 3 , CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), etc., or may include epoxy resin or acrylate such as methacrylate. However, the embodiment is not limited thereto, and the capping layer CPL may include at least one of compounds P1 to P5:

[0419]

[0420]

[0421] The capping layer CPL may have a refractive index equal to or greater than about 1.6. For example, the capping layer CPL may have a refractive index equal to or greater than about 1.6 with respect to light in a wavelength range of about 550 nm to about 660 nm.

[0422] Figures 7 to 10 Each is a schematic cross-sectional view of a display device according to an embodiment. Figures 7 to 10 In the description of the display device of the embodiment shown in Figures 1 to 6 The features described will not be explained again and different features will be described.

[0423] See also Figure 7 , the display device DD-a according to the embodiment may include a display panel DP including a display device layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL.

[0424] exist Figure 7 In the embodiment illustrated in FIG. 1 , the display panel DP may include a base layer BS, a circuit layer DP-CL and a display device layer DP-ED provided on the base layer BS, and the display device layer DP-ED may include a light emitting element ED.

[0425] The light emitting element ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emission layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emission layer EML, and a second electrode EL2 disposed on the electron transport region ETR. Figure 7 The structure of the light emitting element ED shown in FIG. Figures 3 to 6 The structure of the light emitting element ED in one of the above is the same.

[0426] The electron transport region ETR of the light emitting element ED included in the display device DD-a according to the embodiment may include the nitrogen-containing compound represented by Formula 1 according to the embodiment as described above.

[0427] See also Figure 7 , the emission layer EML may be disposed in the opening OH defined by the pixel defining film PDL. For example, the emission layer EML separated by the pixel defining film PDL and correspondingly provided to each of the light emitting areas PXA-R, PXA-G, and PXA-B may emit light within the same wavelength range. In the display device DD-a, the emission layer EML may emit blue light. Although not shown in the drawings, in an embodiment, the emission layer EML may be provided as a common layer for each of the light emitting areas PXA-R, PXA-G, and PXA-B.

[0428] The light control layer CCL may be disposed on the display panel DP. The light control layer CCL may include a light converter. The light converter may be a quantum dot or a phosphor, etc. The light converter may convert the wavelength of the provided light and emit the resulting light. For example, the light control layer CCL may be a layer containing quantum dots or a layer containing phosphors.

[0429] The light-control layer CCL may include light-control parts CCP1, CCP2, and CCP3. The light-control parts CCP1, CCP2, and CCP3 may be spaced apart from each other.

[0430] See also Figure 7 , the partition pattern BMP may be disposed between the light control parts CCP1 , CCP2 , and CCP3 that are spaced apart from each other, but the embodiment is not limited thereto. Figure 7 It is explained that the partition pattern BMP does not overlap with the light control parts CCP1 , CCP2 , and CCP3 , but the edges of the light control parts CCP1 , CCP2 , and CCP3 may overlap with at least a portion of the partition pattern BMP.

[0431] The light control layer CCL may include a first light control component CCP1, which contains first quantum dots QD1 that convert the first color light provided from the light emitting element ED into second color light; a second light control component CCP2, which contains second quantum dots QD2 that convert the first color light into third color light; and a third light control component CCP3, which transmits the first color light.

[0432] In an embodiment, the first light control component CCP1 may provide red light as the second color light, and the second light control component CCP2 may provide green light as the third color light. The third light control component CCP3 may provide blue light by transmitting blue light, which is the first color light provided from the light emitting element ED. For example, the first quantum dot QD1 may be a red quantum dot, and the second quantum dot QD2 may be a green quantum dot. The quantum dots QD1 and QD2 may each be a quantum dot as described above.

[0433] The light control layer CCL may further include a scatterer SP. The first light control part CCP1 may include first quantum dots QD1 and a scatterer SP, the second light control part CCP2 may include second quantum dots QD2 and a scatterer SP, and the third light control part CCP3 may not include quantum dots but may include a scatterer SP.

[0434] The scatterer SP may be inorganic particles. For example, the scatterer SP may include TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow silica. The scatterer SP may include TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow silica, or may be selected from TiO 2 、ZnO、Al 2 O 3 、SiO 2 and a mixture of at least two materials selected from hollow silica.

[0435] The first light control component CCP1, the second light control component CCP2, and the third light control component CCP3 may include base resins BR1, BR2, and BR3, in which quantum dots QD1 and QD2 and a scatterer SP are dispersed. In an embodiment, the first light control component CCP1 may include first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second light control component CCP2 may include second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third light control component CCP3 may include a scatterer SP dispersed in the third base resin BR3.

[0436] The base resins BR1, BR2 and BR3 are media in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and may be formed of various resin compositions that may be generally referred to as adhesives. For example, the base resins BR1, BR2 and BR3 may be acrylic resins, urethane resins, polysiloxane resins, epoxy resins, etc. The base resins BR1, BR2 and BR3 may each be a transparent resin. In an embodiment, the first base resin BR1, the second base resin BR2 and the third base resin BR3 may be the same or different from each other.

[0437] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 may prevent the penetration of moisture and / or oxygen (hereinafter, referred to as "moisture / oxygen"). The barrier layer BFL1 may block the light control components CCP1, CCP2, and CCP3 from being exposed to moisture / oxygen. The barrier layer BFL1 may cover the light control components CCP1, CCP2, and CCP3. In an embodiment, the barrier layer BFL2 may be provided between the light control components CCP1, CCP2, and CCP3 and the filters CF1, CF2, and CF3.

[0438] The barrier layers BFL1 and BFL2 may each independently include at least one inorganic layer. For example, the barrier layers BFL1 and BFL2 may each independently include an inorganic material. For example, the barrier layers BFL1 and BFL2 may each independently include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, a metal film ensuring light transmittance, etc. The barrier layers BFL1 and BFL2 may each independently further include an organic film. The barrier layers BFL1 and BFL2 may each independently be formed of a single layer or a multilayer.

[0439] In the display device DD-a, the color filter layer CFL may be disposed on the light control layer CCL. In an embodiment, the color filter layer CFL may be directly disposed on the light control layer CCL. For example, the blocking layer BFL2 may be omitted.

[0440] The color filter layer CFL may include filters CF1, CF2, and CF3. The color filter layer CFL may include a first filter CF1 that transmits a second color light, a second filter CF2 that transmits a third color light, and a third filter CF3 that transmits the first color light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. The filters CF1, CF2, and CF3 may each include a polymer photosensitive resin and a pigment or dye. The first filter CF1 may include a red pigment or dye, the second filter CF2 may include a green pigment or dye, and the third filter CF3 may include a blue pigment or dye.

[0441] However, the embodiment is not limited thereto, and the third filter CF3 may not include a pigment or a dye. The third filter CF3 may include a polymer photosensitive resin, and may not include a pigment or a dye. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.

[0442] In an embodiment, the first filter CF1 and the second filter CF2 may each be a yellow filter. The first filter CF1 and the second filter CF2 may not be separated but may be provided as one filter.

[0443] Although not shown in the drawings, the color filter layer CFL may further include a light shielding member (not shown). The light shielding member (not shown) may be a black matrix. The light shielding member (not shown) may include an organic light shielding material or an inorganic light shielding material each containing a black pigment or dye. The light shielding member (not shown) may prevent light leakage and may separate adjacent filters CF1, CF2, and CF3.

[0444] The first to third filters CF1, CF2, and CF3 may be disposed to correspond to the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B, respectively.

[0445] The base substrate BL may be disposed on the color filter layer CFL. The base substrate BL may provide a base surface on which the color filter layer CFL, the light control layer CCL, and the like are disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, and the like. However, the embodiment is not limited thereto, and the base substrate BL may include an inorganic layer, an organic layer, or a composite material layer. Although not shown in the drawings, in an embodiment, the base substrate BL may be omitted.

[0446] Figure 8 is a schematic cross-sectional view of a portion of a display device according to an embodiment. In the display devices DD-TD according to the embodiment, the light emitting element ED-BT may include light emitting structures OL-B1, OL-B2, and OL-B3.

[0447] The light emitting element ED-BT may include first and second electrodes EL1 and EL2 facing each other, and light emitting structures OL-B1, OL-B2, and OL-B3 stacked in a thickness direction between the first and second electrodes EL1 and EL2. The light emitting structures OL-B1, OL-B2, and OL-B3 may each include an emission layer EML (see Figure 7 ), and a hole transport region HTR with an emission layer EML disposed therebetween (see Figure 7 ) and the electron transport region ETR (see Figure 7 ).

[0448] For example, the light emitting elements ED-BT included in the display devices DD-TD may be light emitting elements having a tandem structure and including a plurality of emission layers EML.

[0449] exist Figure 8 In the embodiment explained in , the light emitted from the light emitting structures OL-B1, OL-B2 and OL-B3 may each be blue light. However, the embodiment is not limited thereto, and the light emitted from each of the light emitting structures OL-B1, OL-B2 and OL-B3 may have a wavelength range different from each other. For example, the light emitting element ED-BT including the light emitting structures OL-B1, OL-B2 and OL-B3 emitting light having a wavelength range different from each other may emit white light.

[0450] The charge generation layers CGL1 and CGL2 may be disposed between adjacent ones of the light emitting structures OL-B1, OL-B2, and OL-B3, respectively. The charge generation layers CGL1 and CGL2 may each independently include a p-type charge generation layer and / or an n-type charge generation layer.

[0451] At least one of the light emitting structures OL-B1, OL-B2, and OL-B3 in the display devices DD-TD may include the nitrogen-containing compound represented by Formula 1 according to the embodiment. For example, at least one of the electron transport regions included in the light emitting element ED-BT may include the nitrogen-containing compound represented by Formula 1.

[0452] See also Fig. 9 , the display device DD-b according to the embodiment may include light emitting elements ED-1, ED-2, and ED-3 in which two emission layers are stacked. Figure 2 Compared with the display device DD explained in Fig. 9 The difference from the embodiment explained in at least is that the first to third light-emitting elements ED-1, ED-2 and ED-3 each include two emission layers stacked in the thickness direction. In each of the first to third light-emitting elements ED-1, ED-2 and ED-3, the two emission layers can emit light in the same wavelength range.

[0453] The first light-emitting element ED-1 may include a first red emission layer EML-R1 and a second red emission layer EML-R2. The second light-emitting element ED-2 may include a first green emission layer EML-G1 and a second green emission layer EML-G2. The third light-emitting element ED-3 may include a first blue emission layer EML-B1 and a second blue emission layer EML-B2. The emission auxiliary component OG may be disposed between the first red emission layer EML-R1 and the second red emission layer EML-R2, between the first green emission layer EML-G1 and the second green emission layer EML-G2, and between the first blue emission layer EML-B1 and the second blue emission layer EML-B2.

[0454] The emission auxiliary component OG may be a single layer or a multilayer. The emission auxiliary component OG may include a charge generation layer. For example, the emission auxiliary component OG may include an electron transport region (not shown), a charge generation layer (not shown), and a hole transport region (not shown) stacked in sequence. The emission auxiliary component OG may be provided as a common layer for all of the first to third light-emitting elements ED-1, ED-2, and ED-3. However, the embodiment is not limited thereto, and the emission auxiliary component OG may be provided by being patterned within the opening OH defined by the pixel defining film PDL.

[0455] The first red emission layer EML-R1, the first green emission layer EML-G1, and the first blue emission layer EML-B1 may be disposed between the emission auxiliary component OG and the electron transport region ETR. The second red emission layer EML-R2, the second green emission layer EML-G2, and the second blue emission layer EML-B2 may be disposed between the hole transport region HTR and the emission auxiliary component OG.

[0456] For example, the first light-emitting element ED-1 may include a first electrode EL1, a hole transport region HTR, a second red emission layer EML-R2, an emission auxiliary component OG, a first red emission layer EML-R1, an electron transport region ETR, and a second electrode EL2 stacked in the following order. The second light-emitting element ED-2 may include a first electrode EL1, a hole transport region HTR, a second green emission layer EML-G2, an emission auxiliary component OG, a first green emission layer EML-G1, an electron transport region ETR, and a second electrode EL2 stacked in the following order. The third light-emitting element ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue emission layer EML-B2, an emission auxiliary component OG, a first blue emission layer EML-B1, an electron transport region ETR, and a second electrode EL2 stacked in the following order.

[0457] The optical auxiliary layer PL may be disposed on the display device layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be disposed on the display panel DP and may control light reflected by external light at the display panel DP. Although not shown in the drawings, in an embodiment, the optical auxiliary layer PL may be omitted from the display device DD-b.

[0458] Included in Fig. 9 At least one electron transport region ETR in the display device DD-b illustrated in the embodiment may include the nitrogen-containing compound represented by Formula 1 described above according to the embodiment. For example, in the embodiment, at least one of the electron transport regions ETR included in the light emitting elements ED-1, ED-2, and ED-3 may include the nitrogen-containing compound represented by Formula 1.

[0459] and Figure 8 and Fig. 9 compared to, Fig.10 A display device DD-c is explained, which is different at least in that it includes four light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1. The light emitting element ED-CT may include a first electrode EL1 and a second electrode EL2 facing each other, and first to fourth light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1 stacked between the first electrode EL1 and the second electrode EL2 in a thickness direction.

[0460] The light emitting structures OL-C1, OL-B1, OL-B2 and OL-B3 are stacked sequentially, and the charge generation layer CGL1 is disposed between the light emitting structures OL-B1 and OL-C1, the charge generation layer CGL2 is disposed between the light emitting structures OL-B1 and OL-B2, and the charge generation layer CGL3 is disposed between the light emitting structures OL-B2 and OL-B3.

[0461] Among the four light emitting structures, the first to third light emitting structures OL-B1, OL-B2, and OL-B3 may each emit blue light, and the fourth light emitting structure OL-C1 may emit green light. However, the embodiment is not limited thereto, and the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light having different wavelength ranges from each other.

[0462] The charge generation layers CGL1, CGL2, and CGL3 disposed between adjacent light emitting structures among the first to fourth light emitting structures OL-C1, OL-B1, OL-B2, and OL-B3 may each independently include a p-type charge generation layer and / or an n-type charge generation layer.

[0463] In the display device DD-c, at least one of the light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may each independently include the nitrogen-containing compound represented by Formula 1 according to the embodiment.

[0464] Fig.11 is a schematic perspective view of a vehicle AM ​​in which first to fourth display devices DD-1, DD-2, DD-3 and DD-4 are provided. At least one of the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 may have a reference image according to the above description. Figure 1 , Figure 2 and Figures 7 to 10 The structure of one of the display devices DD, DD-TD, DD-a, DD-b and DD-c.

[0465] Fig.11 The vehicle AM ​​is explained, but this is only an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may be provided in various transportation vehicles such as bicycles, motorcycles, trains, ships, and airplanes. In an embodiment, at least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 having a structure according to one of the display devices DD, DD-TD, DD-a, DD-b, and DD-c as described above may be included in a personal computer, a laptop computer, a personal digital terminal, a game console, a portable electronic device, a television, a monitor, or a billboard, etc. However, these are given only as examples, and the display device may be included in other electronic devices.

[0466] At least one of the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 may each independently include a Figures 3 to 6 The light emitting element ED according to any one of the embodiments described in the claims. The light emitting element ED may include the nitrogen-containing compound represented by Formula 1 according to the embodiment. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a light emitting element ED including the nitrogen-containing compound represented by Formula 1 according to the embodiment, thereby improving the element lifespan.

[0467] See also Fig.11 The vehicle AM ​​may include a steering wheel HA and a shift device GR for driving the vehicle AM. The vehicle AM ​​may include a front window GL disposed to face the driver.

[0468] The first display device DD-1 may be disposed in a first area overlapping the steering wheel HA. For example, the first display device DD-1 may be a digital instrument panel displaying first information of the vehicle AM. The first information may include a first scale indicating the driving speed of the vehicle AM, a second scale indicating the engine speed (e.g., revolutions per minute (RPM)), a fuel gauge, etc. The first scale and the second scale may be represented by digital images.

[0469] The second display device DD-2 may be arranged in a second zone facing the driver's seat and overlapping with the front window GL. The driver's seat may be a seat in which a steering wheel HA is arranged. For example, the second display device DD-2 may be a head-up display (HUD) that displays the second information of the vehicle AM. The second display device DD-2 may be optically transparent. The second information may include a number indicating the driving speed, and may further include information such as the current time. Although not shown in the accompanying drawings, in an embodiment, the second information of the second display device DD-2 may be displayed by being projected onto the front window GL.

[0470] The third display device DD-3 may be provided in a third area adjacent to the shift device GR. For example, the third display device DD-3 may be provided between the driver's seat and the passenger seat, and may be a central information display (CID) of the vehicle AM ​​for displaying the third information. The passenger seat may be a seat spaced apart from the driver's seat, with the shift device GR provided therebetween. The third information may include information on traffic conditions (e.g., navigation information), playing music or radio or video (or images), the temperature inside the vehicle AM, and the like.

[0471] The fourth display device DD-4 may be disposed in a fourth area spaced apart from the steering wheel HA and the shift device GR and adjacent to one side of the vehicle AM. For example, the fourth display device DD-4 may be a digital side mirror that displays the fourth information. The fourth display device DD-4 may display an image outside the vehicle AM ​​captured by a camera module CM disposed outside the vehicle AM. The fourth information may include an image outside the vehicle AM.

[0472] The first to fourth information as described above are presented only as examples, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may further display information about the inside and outside of the vehicle AM. The first to fourth information may include information different from each other. However, the embodiment is not limited thereto, and part of the first to fourth information may include the same information as each other.

[0473] Hereinafter, a nitrogen-containing compound represented by Formula 1 according to an embodiment and a light emitting element according to an embodiment will be described with reference to Examples and Comparative Examples. The Examples described below are provided only as explanations to help understand the present disclosure, and the scope thereof is not limited thereto.

[0474] [Example]

[0475] 1. Synthesis of nitrogen-containing compounds

[0476] The synthesis method of the nitrogen-containing compound according to the embodiment will be described in detail by describing the synthesis method of Compounds 2, 30, 40, 71, 90, 116, 120, 155 and 161. The synthesis method of the nitrogen-containing compound described below is provided only as an example, and the synthesis method of the nitrogen-containing compound according to the embodiment is not limited to the following examples.

[0477] (1) Synthesis of Compound 2

[0478] (Synthesis of Intermediate 2-2)

[0479]

[0480] Intermediate 2-1 (1.84 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and (3-phenylnaphthalen-2-yl)boronic acid (2.48 g) were dissolved in tetrahydrofuran (THF) / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60°C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain intermediate 2-2 (2.36g, yield: 67%).

[0481] (Synthesis of Intermediate 2-3)

[0482]

[0483] Intermediate 2-2 (3.52 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and [1,1'-biphenyl]-4-ylboronic acid (1.98 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60°C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain intermediate 2-3 (3.75g, yield: 80%).

[0484] (Synthesis of Compound 2)

[0485]

[0486] Intermediate 2-3 (4.69 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and (9,9-dimethyl-9H-fluoren-2-yl)boronic acid (2.38 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60 ° C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain compound 2 (4.26g, yield: 68%).

[0487] (2) Synthesis of Compound 30

[0488] (Synthesis of Intermediate 30-1)

[0489]

[0490] Intermediate 2-2 (3.52 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and 1-naphthalene boronic acid (1.71 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60°C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain intermediate 30-1 (2.70g, yield: 61%).

[0491] (Synthesis of Compound 30)

[0492]

[0493] Intermediate 30-1 (4.43 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3(3.45 g) and 9,9'-spirobi[fluorene]-2-ylboronic acid (3.60 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60 ° C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate, and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain compound 30 (5.56 g, yield: 77%).

[0494] (3) Synthesis of Compound 40

[0495] (Synthesis of Intermediate 40-1)

[0496]

[0497] Intermediate 2-2 (3.52 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and [1,1':3',1"-terphenyl]-5'-ylboronic acid (2.74 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60°C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain intermediate 40-1 (3.43g, yield: 63%).

[0498] (Synthesis of Compound 40)

[0499]

[0500] Intermediate 40-1 (5.46 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and (2'-phenyl-9,9'-spirobi[fluorene]-2-yl)boronic acid (4.36 g) were dissolved in THF / H 2O (100mL / 25mL), and the reaction solution was stirred at about 60 ° C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate, and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain compound 40 (7.57g, yield: 84%).

[0501] (4) Synthesis of Compound 71

[0502] (Synthesis of Intermediate 71-1)

[0503]

[0504] Intermediate 2-1 (1.84 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and (4-(3-phenylnaphthalen-2-yl)phenyl)boronic acid (3.24 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60°C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain intermediate 71-1 (3.12 g, yield: 73%).

[0505] (Synthesis of Intermediate 71-2)

[0506]

[0507] Intermediate 71-1 (4.28 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and 1-naphthalene boronic acid (1.71 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60°C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain intermediate 71-2 (3.84g, yield: 74%).

[0508] (Synthesis of Compound 71)

[0509]

[0510] Intermediate 71-2 (5.20 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and (3-(9-phenyl-9H-fluoren-9-yl)phenyl)boronic acid (3.62 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60 ° C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate, and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain compound 71 (5.04g, yield: 63%).

[0511] (5) Synthesis of Compound 90

[0512] (Synthesis of Intermediate 90-1)

[0513]

[0514] Intermediate 2-1 (1.84 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and (1-phenylnaphthalen-2-yl)boronic acid (2.48 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60°C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain intermediate 90-1 (2.28g, yield: 65%).

[0515] (Synthesis of Intermediate 90-2)

[0516]

[0517] Intermediate 90-1 (3.52 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and naphthalene-2-ylboronic acid (1.71 g) were dissolved in THF / H 2O (100mL / 25mL), and the reaction solution was stirred at about 60°C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain intermediate 90-2 (3.54g, yield: 80%).

[0518] (Synthesis of Compound 90)

[0519]

[0520] Intermediate 90-2 (4.43 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and (9,9-dimethyl-9H-fluoren-2-yl)boronic acid (2.38 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60 ° C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate, and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain compound 90 (3.78 g, yield: 63%).

[0521] (6) Synthesis of Compound 116

[0522] (Synthesis of Intermediate 116-1)

[0523]

[0524] Intermediate 90-1 (3.52 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and [1,1'-biphenyl]-3-ylboronic acid (1.98 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60°C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain intermediate 116-1 (3.33 g, yield: 71%).

[0525] (Synthesis of Compound 116)

[0526]

[0527] Intermediate 116-1 (4.69 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and 9,9'-spirobi[fluorene]-2-ylboronic acid (3.60 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60 ° C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain compound 116 (5.46 g, yield: 73%).

[0528] (7) Synthesis of Compound 120

[0529] (Synthesis of Intermediate 120-1)

[0530]

[0531] Intermediate 90-1 (3.52 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and naphthalene-2-ylboronic acid (1.71 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60 ° C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain compound 120-1 (3.01g, yield: 68%).

[0532] (Synthesis of Compound 120)

[0533]

[0534] Intermediate 120-1 (4.43 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and 9,9'-spirobi[fluorene]-2-ylboronic acid (3.60 g) were dissolved in THF / H2 O (100mL / 25mL), and the reaction solution was stirred at about 60 ° C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain compound 120 (4.98 g, yield: 69%).

[0535] (8) Synthesis of Compound 155

[0536] (Synthesis of Intermediate 155-1)

[0537]

[0538] Intermediate 2-1 (1.84 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and (4-(1-phenylnaphthalen-2-yl)phenyl)boronic acid (3.24 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60°C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and extracted three times with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain intermediate 155-1 (2.82g, yield: 66%).

[0539] (Synthesis of Compound 155-2)

[0540]

[0541] Intermediate 155-1 (4.28 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and [1,1':4',1"-terphenyl]-4-ylboronic acid (2.74 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60°C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and extracted three times with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain intermediate 155-2 (4.16 g, yield: 67%).

[0542] (Synthesis of Compound 155)

[0543]

[0544] Intermediate 155-2 (6.22 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and (9,9-diphenyl-9H-fluoren-2-yl)boronic acid (3.60 g) were dissolved in THF / H 2 The mixture was stirred at about 60 ° C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and the organic layer was separated by three extractions with ether. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain compound 155 (6.32 g, yield: 70%).

[0545] (9) Synthesis of Compound 161

[0546] (Synthesis of Compound 161-1)

[0547]

[0548] Intermediate 155-1 (4.28 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3 (3.45 g) and 1-naphthalene boronic acid (1.71 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60°C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and extracted three times with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain intermediate 161-1 (3.64g, yield: 70%).

[0549] (Synthesis of Compound 161)

[0550]

[0551] Intermediate 161-1 (5.20 g), Pd(PPh 3 ) 4 (0.56g), K 2 CO 3(3.45 g) and 9,9'-spirobi[fluorene]-2-ylboronic acid (3.60 g) were dissolved in THF / H 2 O (100mL / 25mL), and the reaction solution was stirred at about 60 ° C for about 12 hours. The reaction solution was cooled to room temperature and the reaction was terminated with water, and three extractions were performed with ether to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain a residue. The obtained residue was separated and purified by column chromatography to obtain compound 161 (6.39 g, yield: 80%).

[0552] 2. Manufacturing and evaluation of light-emitting components

[0553] (1) Manufacturing of light-emitting elements

[0554] The light-emitting element according to the embodiment including the nitrogen-containing compound according to the embodiment in the electron transport region was manufactured as follows. Compounds 2, 30, 40, 71, 90, 116, 120, 155 and 161, which are the example compounds described above, were respectively used as materials for the electron transport layer to manufacture the light-emitting elements of Examples 1 to 9. Comparative Examples 1 to 5 correspond to light-emitting elements manufactured by using Comparative Example Compounds C1 to C4 as materials for the electron transport layer.

[0555] [Example Compounds]

[0556]

[0557] [Comparative Example Compound]

[0558]

[0559] (Manufacturing of light-emitting elements)

[0560] In the light-emitting elements of the examples and comparative examples, a 15Ω / cm 2 (about A glass substrate (manufactured by Corning) with an ITO electrode of ) as a first electrode was cut into a size of about 50 mm x 50 mm x 0.7 mm, cleaned by ultrasonic wave using isopropyl alcohol and pure water for about 5 minutes each, irradiated with ultraviolet light for about 30 minutes, exposed to ozone and cleaned. The glass substrate was mounted on a vacuum deposition apparatus.

[0561] NPD is deposited on the top of the first electrode to form The compound H-1-1 is deposited on the upper portion of the hole injection layer to form a A thick hole transport layer is formed, and CzSi is deposited on the upper portion of the hole transport layer to form Thick emission assist layer.

[0562] A host material in which the second compound and the third compound are mixed in a weight ratio of about 1:1, a fourth compound as a sensitizer, and a first compound as a dopant material are co-deposited on the upper portion of the emission auxiliary layer in a weight ratio of about 84:15:1 to form TSPO1 is deposited on the upper part of the emission layer to form The example compound or the comparative example compound is deposited on the upper part of the hole blocking layer to form a A thick electron transport layer, LiF is deposited on the upper part of the electron transport layer to form A thick electron injection layer is formed, and Al is deposited on the upper portion of the electron injection layer to form A second electrode having a thickness of 100 mm / s is formed to form a light emitting element. Each layer is formed by a vacuum deposition method.

[0563] Compound HT2 or Compound HT3, each from Compound Group 2 as described above, is used as the second compound; Compound ETH66 or Compound ETH86, each from Compound Group 3 as described above, is used as the third compound; Compound AD-37 or Compound AD-38, each from Compound Group 4 as described above, or Compound AD-C below is used as the fourth compound; and t-DABNA is used as the first compound. Comparative Example 5 does not use a host material in which the second compound and the third compound are mixed at a weight ratio of about 1:1, but uses the following Compound EC as the host material.

[0564]

[0565] (2) Evaluation of light-emitting element characteristics

[0566] (Evaluation of light-emitting element characteristics)

[0567] The luminous efficiency and element life of the light-emitting elements manufactured using Example Compounds 2, 30, 40, 71, 90, 116, 120, 155 and 161 and Comparative Example Compounds C1 to C4 as described above were evaluated. The evaluation results of the light-emitting elements in Examples 1 to 9 and Comparative Examples 1 to 5 are listed in Table 1. In order to evaluate the characteristics of the light-emitting elements manufactured in Examples 1 to 9 and Comparative Examples 1 to 5 above, the luminance at 1,000 cd / m was measured by using Keithley MU 236 and luminance meter PR650, respectively. 2 The driving voltage (V) and luminous efficiency (Cd / A) at a current density of , and the time taken to reach 95% brightness relative to the initial brightness was measured as the element service life (T95), and the relative element service life was calculated based on the light-emitting element of Comparative Example 1, and the results are listed in Table 1.

[0568] [Table 1]

[0569]

[0570]

[0571] As shown in the results of Table 1, compared with the light-emitting element of the comparative example, the light-emitting element of the embodiment using the nitrogen-containing compound according to the embodiment as the material of the electron transport layer shows a relatively low driving voltage, high luminous efficiency and long element life. The embodiment compound has a structure including a triazine ring and a first substituent and a second substituent each connected to the carbon atom of the triazine ring, so that high luminous efficiency and long element life can be achieved. The first substituent may include a phenyl naphthalene portion. The phenyl naphthalene portion of the first substituent may include a naphthalene portion and a benzene portion connected to the naphthalene portion. The benzene portion and the triazine ring may be connected to the naphthalene portion of the first substituent at the ortho position to each other. The second substituent may include a fluorene portion. The fluorene portion of the second substituent may be a structure substituted by a methyl or phenyl group, or two phenyl substituents of the fluorene portion may be bonded to each other to form a spiro structure. In the second substituent, the carbon atom of the aromatic ring in the fluorene portion may be connected to the triazine ring. The nitrogen-containing compound of the embodiment may have a triazine ring to which the first substituent and the second substituent are connected, so as to have charge transport capability. Therefore, the light-emitting element of the example including the example compound as a material for the electron transport layer can be expected to exhibit relatively high light emission efficiency and long element life compared to the light-emitting element in the comparative example.

[0572] Comparative Example Compound C1 includes a heterocyclic ring containing a nitrogen atom, but does not include a triazine ring or the first and second substituents according to the embodiment. Accordingly, it is considered that the light emitting element of Comparative Example 1 including Comparative Example Compound C1 exhibits deterioration in luminous efficiency and element life.

[0573] Comparative example compound C2 includes a triazine ring according to an embodiment and a first substituent connected to the triazine ring, but does not include a second substituent. Accordingly, it can be confirmed that the light-emitting elements of Comparative Example 2 and Comparative Example 5, each including Comparative Example Compound C2, have a relatively high driving voltage value compared to the light-emitting element including the embodiment compound, and exhibit degradation of luminous efficiency and element service life. It is believed that Comparative Example Compound C2 includes a naphthyl or phenylnaphthyl group instead of a second substituent, and thus the characteristics of the light-emitting elements of Comparative Example 2 and Comparative Example 5, including Comparative Example Compound C2, are degraded.

[0574] Comparative example compound C3 includes a triazine ring according to an embodiment and a second substituent connected to the triazine ring, but does not include a first substituent. Accordingly, it can be confirmed that the light-emitting element of Comparative Example 3 including Comparative Example Compound C3 has a relatively high driving voltage value compared to the light-emitting element including the embodiment compound, and exhibits degradation of luminous efficiency and element service life. It is believed that Comparative Example Compound C3 includes an unsubstituted naphthyl group instead of a first substituent, and thus the characteristics of the light-emitting element of Comparative Example 3 including Comparative Example Compound C3 are degraded.

[0575] Comparative example compound C4 includes a triazine ring, but does not include the first substituent and the second substituent according to the embodiment. Accordingly, it can be confirmed that compared with the light-emitting element including the embodiment compound, the light-emitting element of the comparative example 4 including the comparative example compound C4 has a relatively high driving voltage value, and shows the degradation of luminous efficiency and element service life. It is believed that the comparative example compound C4 includes a naphthyl group connected to naphthobenzofuran instead of a first substituent, and a methylfluorenyl group (wherein the triazine ring is connected to the carbon atom of the pentagonal ring in the fluorene part by a phenylene group) connected to the triazine ring instead of a second substituent, thus including the characteristic degradation of the light-emitting element of the comparative example 4 of the comparative example compound C4.

[0576] The light emitting element according to the embodiment may exhibit improved light emitting element characteristics with high light emitting efficiency and long element lifespan.

[0577] The nitrogen-containing compound according to the embodiment may be included in an electron transport region of a light emitting element, contributing to high light emission efficiency and long element life of the light emitting element.

[0578] The display device according to the embodiment may include a light emitting element having excellent light emitting efficiency and element lifespan.

[0579] Embodiments have been disclosed herein, and although terms are used, they are used and interpreted in a general and descriptive sense only and not for purposes of limitation. In some cases, as will be apparent to one of ordinary skill in the art, features, characteristics, and / or elements described in conjunction with an embodiment may be used alone or in combination with features, characteristics, and / or elements described in conjunction with other embodiments, unless otherwise specifically specified. Therefore, one of ordinary skill in the art will understand that various changes in form and details may be made without departing from the spirit and scope of the present disclosure as set forth in the claims.

Claims

1. A nitrogen-containing compound represented by Formula 1: Formula 1 In formula 1, Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, L 1 and L 2 are each independently a directly linked or substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, R 1 is a group represented by Formula 2, and R 2 is a group represented by Formula 3-1, Formula 3-2 or Formula 3-3: Formula 2 In Formula 2, X 1 To X 7 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, The premise is X 1 or X 7 is a substituted or unsubstituted phenyl group, and *- is connected to L in formula 1 1 Location: Formula 3-1 Formula 3-2 Formula 3-3 In formula 3-1, Y 1 and Y 2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, In Formula 3-1 to Formula 3-3, R a1 To R a8 , R b1 To R b18 and R c1 To R c16 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, The premise is When R in Formula 1 2 When it is a group represented by Formula 3-1, R in Formula 3-1 a1 To R a8 Any one of them is connected to L in Formula 1 2 location, When R in Formula 1 2 When it is a group represented by formula 3-2, R in formula 3-2 b1 To R b18 Any one of them is connected to L in Formula 1 2 location, and When R in Formula 1 2 When it is a group represented by formula 3-3, R in formula 3-3 c1 To R c16 Any one of them is connected to L in Formula 1 2 location.

2. The nitrogen-containing compound according to claim 1, wherein Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

3. The nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound represented by Formula 1 is represented by any one of Formulas 1-1 to 1-4: Formula 1-1 Formula 1-2 Formula 1-3 Formula 1-4 In Formula 1-1 to Formula 1-4, X 11 To X 18 are each independently a hydrogen atom or a deuterium atom, n1, n3, n5 and n7 are each independently an integer selected from 0 to 5, n2, n4, n6 and n8 are each independently an integer selected from 0 to 6, and Ar, L 2 and R 2 Same as defined in Formula 1.

4. The nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound represented by Formula 1 is represented by any one of Formulas 1-5 to 1-9: Formula 1-5 Formula 1-6 Formula 1-7 Formula 1-8 Formula 1-9 Wherein in Formula 1-5 to Formula 1-9, R x1 To R x14 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, m1 and m2 are each independently an integer selected from 0 to 7, m3 to m5, m9, m11, m13 and m14 are each independently an integer selected from 0 to 4, m6 and m10 are each independently an integer selected from 0 to 3, m7, m8 and m12 are each independently an integer selected from 0 to 5, and Ar, L 1 and R 1 Same as defined in Formula 1.

5. The nitrogen-containing compound according to claim 4, wherein R x1 To R x3 and R x5 To R x14 are each a hydrogen atom, and R x4 is a hydrogen atom or a substituted or unsubstituted phenyl group.

6. The nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound represented by Formula 1 is represented by any one of Formulas 1-10 to 1-14: Formula 1-10 Formula 1-11 Formula 1-12 Formula 1-13 Formula 1-14 Wherein in Formula 1-10 to Formula 1-14, Ar, L 1 and R 1 Same as defined in Formula 1.

7. The nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound represented by Formula 1 is selected from Compound Group 1: Compound Group 1 8. A light emitting element, include: a first electrode; a hole transport region disposed on the first electrode; an emission layer disposed on the hole transport region; An electron transport region disposed on the emission layer; and A second electrode is disposed on the electron transport region, wherein The electron transport region comprises a nitrogen-containing compound according to any one of claims 1 to 7, and The emission layer includes an organic metal compound represented by Formula D-1: Formula D-1 Wherein in formula D-1, Q 1 To Q 4 are each independently C or N, C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms, L 11 To L 13 Each is independently connected to the a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, in which L 11 To L 13 middle, represents a bond connected to one of C1 to C4, b1 to b3 are each independently 0 or 1, R 61 To R 66 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, or bonds to an adjacent group to form a ring, and d1 to d4 are each independently an integer selected from 0 to 4.

9. The light-emitting element according to claim 8, wherein The electron transport region include: An electron transport layer disposed on the emission layer; and an electron injection layer disposed on the electron transport layer, and The electron transport layer includes the nitrogen-containing compound represented by Formula 1 according to any one of claims 1 to 7.

10. The light-emitting element according to claim 8, wherein the emission layer further comprises a compound represented by formula Fc: Formula Fc Wherein in Formula Fc, A 1 and A 2 Each independently is O, S, Se or N (R m ), R 1 To R 11 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or bonds to an adjacent group to form a ring, and R m is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

Images