Light-emitting element, display device, and organometallic compound therefor

Abstract

Provided are a light-emitting element, a display device, and an organometallic compound represented by Formula 1 for the same. The light emitting element may include a first electrode, a second electrode on the first electrode, and an emission layer between the first electrode and the second electrode. The emission layer may contain an organometallic compound represented by Formula 1 as a first compound and exhibit low driving voltage and improved luminous efficiency characteristics. Formula 1 # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0093757 filed in the Korean Intellectual Property Office on July 19, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Embodiments of the present disclosure herein relate to a light-emitting element, an organometallic compound used therein, and a display device including the light-emitting element. Background Art

[0004] As image display devices, organic electroluminescent display devices and the like have been actively developed recently. The organic electroluminescent display device and the like are display devices including a so-called self-luminous light-emitting element in which holes and electrons injected from a first electrode and a second electrode, respectively, are recombined in an emission layer, and thus the light-emitting material in the emission layer emits light to provide display.

[0005] In order to apply light-emitting elements to display devices, there is an interest in higher light efficiency and lifetime, and research is being continued on the development of materials for light-emitting elements that can stably obtain such characteristics. Summary of the invention

[0006] Embodiments of the present disclosure provide a light-emitting element having a low driving voltage property and improved light-emitting efficiency.

[0007] Embodiments of the present disclosure also provide an organometallic compound designed to improve light efficiency of a light emitting element.

[0008] Embodiments of the present disclosure also provide a display device having excellent display quality, which includes a light emitting element having improved light emitting efficiency.

[0009] Embodiments of the present disclosure provide an organometallic compound represented by Formula 1 below.

[0010] Formula 1

[0011]

[0012] In the above formula 1, W 1 To W 3At least one of them is O or S and the rest are CRa, Ra is a hydrogen atom, a deuterium atom, a halogen atom, 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 oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 ring-forming carbon atoms, or is bonded to an adjacent group to form a ring, and R 1 , R 2 and R 11 To R 26 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, 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 oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 ring-forming carbon atoms.

[0013] In the embodiment, the above Formula 1 may be represented by the following Formula 1-1.

[0014] Formula 1-1

[0015]

[0016] In the above formula 1-1, W 11 O or S, R a1 and R a2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, 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 oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 ring carbon atoms, and R 1 , R 2 and R 11 To R 26 Same as defined above with respect to Formula 1.

[0017] In an embodiment, R a1 and R a2 It may be a hydrogen atom.

[0018] In an embodiment, the above Formula 1 may be represented by the following Formula 1-2.

[0019] Formula 1-2

[0020]

[0021] In the above formula 1-2, W 11 is O or S, Cy is a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring having 3 to 30 ring carbon atoms, and R 1 , R 2 and R 11 To R 26 Same as defined above with respect to Formula 1.

[0022] In an embodiment, Cy above may be a substituted or unsubstituted benzene ring.

[0023] In an embodiment, the compound represented by Formula 1 above may emit phosphorescence (eg, may emit light by way of phosphorescence).

[0024] In an embodiment of the present disclosure, a light-emitting element includes a first electrode, a second electrode on the first electrode, and an emission layer between the first electrode and the second electrode and containing a first compound, the first compound being the organic metal compound of the embodiment.

[0025] In the embodiment, the light-emitting element may further include at least one of the following second compound represented by Formula HT-1 and the third compound represented by Formula ET-1.

[0026] Formula HT-1

[0027]

[0028] In the above formula HT-1, A 1 To A 8 Each independently is N or CR 51 , L 1 is a direct bond, 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, Y a For direct connection key, CR 52 R 53 or SiR 54 R 55 , and Ar 1 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. 51 To R 55Each is 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 is bonded to an adjacent group to form a ring.

[0029] Formula ET-1

[0030]

[0031] In the above formula ET-1, X 1 To X 3 At least one of them is N and the rest are CR 56 , CR 56 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 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, and b1 to b3 are each independently an integer of 0 to 10. Ar 2 To Ar 4 are each independently 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, and L 2 To L 4 Each is independently a direct bond, 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.

[0032] In an embodiment, the emission layer may further include a fourth compound represented by the following Formula F-1.

[0033] Formula F-1

[0034]

[0035] In the above formula F-1, A 1 and A 2 Each independently is O, S, Se or NR m , R mis 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, and R 1a To R 11a Each is independently 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 is bonded to an adjacent group to form a ring.

[0036] In an embodiment, the emission layer may include the first compound, the second compound, the third compound, and the fourth compound.

[0037] In an embodiment, the emission layer may include a host and a phosphorescent dopant, and the phosphorescent dopant may be the first compound.

[0038] In an embodiment, the emitting layer may emit blue light having a maximum center wavelength of about 470 nm or less.

[0039] In an embodiment of the present disclosure, a display device includes a base layer, a circuit layer on the base layer, and a display element layer on the circuit layer and including a light-emitting element, wherein the light-emitting element includes a first electrode, a second electrode facing the first electrode, and an emission layer between the first electrode and the second electrode and containing an organic metal compound.

[0040] In an embodiment, the light emitting element may emit blue light.

[0041] In an embodiment, the display device may include a light management layer including quantum dots. BRIEF DESCRIPTION OF THE DRAWINGS

[0042] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated in and constitute a part of this specification. The accompanying drawings illustrate embodiments of the present disclosure and together with the description serve to explain the principles of the present disclosure. In the drawings:

[0043] Figure 1 is a plan view showing a display device according to the embodiment;

[0044] Figure 2 is shown along Figure 1A cross-sectional view of a portion taken along line II';

[0045] Figure 3 is a cross-sectional view schematically showing a light emitting element according to the embodiment;

[0046] Figure 4 is a cross-sectional view schematically showing a light emitting element according to the embodiment;

[0047] Figure 5 is a cross-sectional view schematically showing a light emitting element according to the embodiment;

[0048] Figure 6 is a cross-sectional view schematically showing a light emitting element according to the embodiment;

[0049] Figure 7 is a cross-sectional view schematically showing a light emitting element according to the embodiment;

[0050] Figure 8 is a cross-sectional view showing a display device according to the embodiment;

[0051] Fig. 9 is a cross-sectional view showing a display device according to the embodiment;

[0052] Fig.10 is a cross-sectional view showing a display device according to the embodiment;

[0053] Fig.11 is a cross-sectional view showing a display device according to the embodiment; and

[0054] Fig.12 is a view showing the interior of a vehicle in which the display device of the embodiment is provided. DETAILED DESCRIPTION

[0055] The subject matter of the present disclosure can be modified in many ways and have many forms, so example embodiments will be shown in the drawings and described in more detail in the "Detailed Description" section of the present disclosure. However, it should be understood that it is not intended to limit the subject matter of the present disclosure to the specific form disclosed, but is intended to cover all modifications, equivalents and substitutions that fall within the spirit and scope of the present disclosure.

[0056] When explaining each accompanying drawing, the same reference numerals are used to refer to the same elements. In the accompanying drawings, for the clarity of the present disclosure, the size of each structure can be illustrated in an amplified manner. It should be understood that although the terms "first", "second", etc. can be used to describe various components in this article, these components should not be limited by these terms. These terms are only used to distinguish one component from another component. For example, without departing from the scope of the exemplary embodiments of the present disclosure, the first component can be referred to as the second component, and similarly, the second component can be referred to as the first component. As used herein, the singular "a", "an", and "the" are intended to also include plural forms, unless the context clearly states otherwise.

[0057] In the present disclosure, it should be understood that the terms "including", "having", etc. specify the existence of features, numbers, steps, operations, components, parts or combinations thereof disclosed in the specification, but do not exclude the existence or addition of one or more other features, numbers, steps, operations, components, parts or combinations thereof.

[0058] In the present disclosure, when a layer, film, region or plate is referred to as being "on" or "in the upper part of" another layer, film, region or plate, it may not only be directly on the layer, film, region or plate, but also there may be intervening layers, films, regions or plates. In contrast, when a layer, film, region or plate is referred to as being "under" or "in the lower part of" another layer, film, region or plate, it may not only be directly under the layer, film, region or plate, but also there may be intervening layers, films, regions or plates. In addition, it should be understood that when a component is referred to as being "on" another component, it may be above the other component, or it may also be below the other component.

[0059] In the specification, the term "substituted or unsubstituted" can mean substituted or unsubstituted by at least one substituent selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, nitro groups, amino 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. In addition, each of the substituents exemplified above can be substituted or unsubstituted. For example, a biphenyl group can be interpreted as an aryl group or a phenyl group substituted by a phenyl group.

[0060] In the specification, the phrase "bonded to an adjacent group to form a ring" may mean that a group is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles may be monocyclic or polycyclic. In addition, the ring formed by bonding to each other may be connected to another ring to form a spiro structure.

[0061] In the specification, the term "adjacent group" may mean a substituent that replaces an atom directly connected to an atom substituted by a corresponding substituent, another substituent that replaces an atom substituted by a corresponding substituent, or a substituent that is spatially located at the nearest position to the corresponding substituent. 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. In addition, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups" to each other.

[0062] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0063] In the specification, the alkyl group may be straight chain or branched. The number of carbons 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 a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, a tert-butyl group, an isobutyl group, a 2-ethylbutyl group, a 3,3-dimethylbutyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a 1-methylpentyl group, a 3-methylpentyl group, a 2-ethylpentyl group, a 4-methyl-2-pentyl group, an n-hexyl group, a 1-methylhexyl group, a 2-ethyl tert-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, n-nonyl group, n-decyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group, An n-undecyl group, an n-dodecyl group, a 2-ethyldodecyl group, a 2-butyldodecyl group, a 2-hexyldodecyl group, a 2-octyldodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, a 2-ethylhexadecyl group, a 2-butylhexadecyl group, a 2-hexylhexadecyl group, a 2-octylhexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, an n-eicosyl group, a 2-ethyleicosyl group, a 2-butyleicosyl group, a 2-hexyleicosyl group, a 2-octyleicosyl group, an n-heneicosyl group, an n-docosyl group, an n-tricosyl group, an n-tetracosyl group, an n-pentacosyl group, an n-hexacosyl group, an n-heptacosyl group, an n-octacosyl group, an n-nonacosyl group, an n-triacontyl group, and the like, but the embodiments of the present disclosure are not limited thereto.

[0064] In the specification, a cycloalkyl group may refer to a cyclic alkyl group. The carbon number in the cycloalkyl group may be 3 to 50, 3 to 30, 3 to 20 or 3 to 10. Examples of cycloalkyl groups may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a norbornyl group, a 1-adamantyl group, a 2-adamantyl group, an isobornyl group, a bicycloheptyl group, etc., but the embodiments of the present disclosure are not limited thereto.

[0065] In the specification, alkenyl group means a hydrocarbon group containing at least one carbon-carbon double bond in the main chain (e.g., in the middle) or at the end of an alkyl group having 2 or more carbon atoms. The alkenyl group can be straight chain or branched. The number of carbon atoms in the alkenyl group is not particularly limited, but can be 2 to 30, 2 to 20 or 2 to 10. Examples of alkenyl groups include vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienyl groups, styryl groups, styryl vinyl groups, etc., but the embodiments of the present disclosure are not limited thereto.

[0066] In the specification, alkynyl group means a hydrocarbon group containing at least one carbon-carbon triple bond in the main chain (e.g., in the middle) or at the end of an alkyl group having 2 or more carbon atoms. Alkynyl group can be straight chain or branched. Although the number of carbon atoms is not specifically limited, it can be 2 to 30, 2 to 20 or 2 to 10. Examples of alkynyl groups can include ethynyl groups, propynyl groups, etc., but are not limited thereto.

[0067] In the specification, the hydrocarbon ring group means any suitable functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 (e.g., 5 to 15, 5 to 10, or 5 to 8) ring-forming carbon atoms.

[0068] In the specification, aryl group means any suitable functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group can be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms in the aryl group can be 6 to 30, 6 to 20 or 6 to 15. Examples of aryl groups can include phenyl groups, naphthyl groups, fluorenyl groups, anthracenyl groups, phenanthrenyl groups, biphenyl groups, terphenyl groups, quaterphenyl groups, pentaphenyl groups, hexaphenyl groups, triphenylenyl groups, pyrenyl groups, benzofluoranthenyl groups, However, the embodiments of the present disclosure are not limited thereto.

[0069] 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 substituted fluorenyl groups are as follows. However, embodiments of the present disclosure are not limited thereto.

[0070]

[0071] Heterocyclic groups herein mean any suitable functional group or substituent derived from a ring containing at least one of B, O, N, P, Si and S as a heteroatom (e.g., 1 to 15, 1 to 10, 1 to 5 or 1 to 3 heteroatoms). Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl groups. Aliphatic heterocyclic rings and aromatic heterocyclic rings may be monocyclic or polycyclic.

[0072] In the specification, the heterocyclic group may contain at least one of B, O, N, P, Si and S as a heteroatom. If the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and includes a heteroaryl group. The number of ring carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10.

[0073] In the specification, the aliphatic heterocyclic group may contain at least one of B, O, N, P, Si and S as a heteroatom. The number of ring 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, a thiirane group, a pyrrolidine group, a piperidine group, a tetrahydrofuran group, a tetrahydrothiophene group, a thihexane group, a tetrahydropyran group, a 1,4-dioxane group, and the like, but embodiments of the present disclosure are not limited thereto.

[0074] In the specification, the heteroaryl group may contain at least one of B, O, N, P, Si and S as a heteroatom (e.g., 1 to 15, 1 to 10, 1 to 5 or 1 to 3 heteroatoms). If the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20 or 2 to 10. Examples of the heteroaryl group may include a thiophene group, a furan group, a pyrrole group, an imidazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group, a pyridazine group, a pyrazine group, a quinoline group, a quinazoline group, a quinoxaline group, a phenoxazine group, a phthalazine group, a pyridopyrimidine group, a pyridopyrazine group, a pyrazinopyrazine group, an isoquinoline group, an indole group, a carbazole group, an N-arylcarbazole group, N-heteroarylcarbazole group, N-alkylcarbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, thienothiophene group, benzofuran group, phenanthroline group, thiazole group, isoxazole group, oxazole group, oxadiazole group, thiadiazole group, phenothiazine group, dibenzosilole group, dibenzofuran group and the like, but the embodiments of the present disclosure are not limited thereto.

[0075] 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. The above description of the heteroaryl group may be applied to the heteroarylene group, except that the heteroarylene group is a divalent group.

[0076] In the present specification, silyl groups include alkylsilyl groups and arylsilyl groups. Examples of silyl groups may include trimethylsilyl groups, triethylsilyl groups, tert-butyldimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, phenylsilyl groups, etc., but the embodiments of the present disclosure are not limited thereto.

[0077] In the specification, the number of carbon atoms and / or the number of ring-forming carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have the following structure, but embodiments of the present disclosure are not limited thereto.

[0078]

[0079] In the specification, the number of carbon atoms in the sulfinyl group and the sulfonyl group is not particularly limited, but may be 1 to 30, 1 to 20, 1 to 10, or 1 to 6. The sulfinyl group may include an alkylsulfinyl group and an arylsulfinyl group. The sulfonyl group may include an alkylsulfonyl group and an arylsulfonyl group.

[0080] In the specification, the thiol group may include an alkylthiol group and an arylthiol group. The thiol group may mean that the sulfur atom is bonded to an alkyl group or an aryl group as defined above. Examples of thiol groups may include a methylthiol group, an ethylthiol group, a propylthiol group, a pentylthiol group, a hexylthiol group, an octylthiol group, a dodecylthiol group, a cyclopentylthiol group, a cyclohexylthiol group, a phenylthiol group, a naphthylthiol group, etc., but the embodiments of the present disclosure are not limited thereto.

[0081] In the specification, an oxy group may mean that an oxygen atom is bonded to an alkyl group or an aryl group as defined above. An oxy group may include an alkoxy group and an aryloxy group. An alkoxy group may be a straight chain, a branched chain or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of oxy groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc., but the embodiments of the present disclosure are not limited thereto.

[0082] Boron group means herein that a boron atom is bonded to an alkyl group or an aryl group as defined above. Boron groups include alkyl boron groups and aryl boron groups. Examples of boron groups may include dimethyl boron groups, tert-butyl methyl boron groups, diphenyl boron groups, phenyl boron groups, etc., but embodiments of the present disclosure are not limited thereto.

[0083] In the specification, the number of carbon atoms in the amine group is not particularly limited, but may be 1 to 30, 1 to 20, 1 to 10, or 1 to 6. The amine group may include an alkylamine group and an arylamine group. Examples of the amine group may include a methylamine group, a dimethylamine group, a phenylamine group, a diphenylamine group, a naphthylamine group, a 9-methyl-anthrylamine group, etc., but the embodiments of the present disclosure are not limited thereto.

[0084] In the specification, the alkyl group in the alkylthio group, the alkylsulfonyloxy group, the alkylaryl group, the alkylamino group, the alkylboron group, the alkylsilyl group, and the alkylamine group is the same as the examples of the alkyl group described above.

[0085] In the specification, the aryl group in the aryloxy group, arylthio group, arylsulfonyloxy group, arylamino group, arylboron group, arylsilyl group, arylamine group is the same as the examples of the aryl group described above.

[0086] In the specification, a direct bond may mean a single bond.

[0087] In the manual, and "-*" means the location to be linked.

[0088] Hereinafter, embodiments of the present disclosure will be described with reference to the accompanying drawings.

[0089] Figure 1 is a plan view of a display device DD according to an exemplary embodiment. Figure 2 is a cross-sectional view of a display device DD of the embodiment. Figure 2 is an example along Figure 1 A cross-sectional view of a portion taken along line II'.

[0090] The display device DD may include a display panel DP and an optical layer PP 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 on the display panel DP to control reflected light due to external light in the display panel DP. The optical layer PP may include, for example, a polarizing layer and / or a color filter layer. In some embodiments, the optical layer PP may be omitted from the display device DD of the embodiment.

[0091] The base substrate BL may be on the optical layer PP. The base substrate BL may be a member providing a base surface on which the optical layer PP is provided. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or an organic-inorganic composite material layer. In some embodiments, the base substrate BL may be omitted.

[0092] The display device DD according to the embodiment may further include a filling layer. The filling layer may be between the display element layer DP-ED and the base substrate BL. The filling layer may be an organic material layer. The filling layer may include at least one of an acrylic-based resin, a silicone-based resin, and an epoxy-based resin.

[0093] The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED. The display element layer DP-ED may include a pixel defining layer PDL, light emitting elements ED-1, ED-2, and ED-3 between portions of the pixel defining layer PDL, and an encapsulation layer TFE on the light emitting elements ED-1, ED-2, and ED-3.

[0094] The base layer BS may be a member providing a base surface on which the display element layer DP-ED is provided. 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 be an inorganic layer, an organic layer, or an organic-inorganic composite material layer.

[0095] In the embodiment, the circuit layer DP-CL is on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors. Each of the transistors may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include a switch transistor and a driving transistor for driving the light-emitting elements ED-1, ED-2, and ED-3 of the display element layer DP-ED.

[0096] Each of the light emitting elements ED-1, ED-2 and ED-3 may have a light emitting element having ... Figures 3 to 7 Each of the light emitting elements ED-1, ED-2 and ED-3 may 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.

[0097] Figure 2 An embodiment is illustrated 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 in the opening OH defined in the pixel defining layer PDL, and the hole transport region HTR, the electron transport region ETR and the second electrode EL2 are provided as a common layer in the entire light-emitting elements ED-1, ED-2 and ED-3. However, the embodiments of the present disclosure are not limited thereto, and in some embodiments, the hole transport region HTR and the electron transport region ETR in the embodiments can be provided by patterning in the opening OH defined in the pixel defining layer PDL. For example, 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 in the embodiments can be provided by patterning using an inkjet printing method.

[0098] The encapsulation layer TFE may cover the light emitting elements ED-1, ED-2 and ED-3. The encapsulation layer TFE may seal the display element layer DP-ED. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be formed by laminating one or more layers. The encapsulation layer TFE includes at least one insulating layer (e.g., an electrical insulating layer). The encapsulation layer TFE according to the embodiment may include at least one inorganic film (hereinafter, encapsulation inorganic film). The encapsulation layer TFE according to the embodiment may also include at least one organic film (hereinafter, encapsulation organic film) and at least one encapsulation inorganic film.

[0099] The encapsulated inorganic film protects the display element layer DP-ED from moisture / oxygen, and the encapsulated organic film protects the display element layer DP-ED from foreign substances such as dust particles. The encapsulated inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, aluminum oxide, etc., but the embodiments of the present disclosure are not particularly limited thereto. The encapsulated organic film may include an acrylic-based compound, an epoxy-based compound, etc. The encapsulated organic film may include a photopolymerizable organic material, but the embodiments of the present disclosure are not particularly limited thereto.

[0100] The encapsulation layer TFE may be on the second electrode EL2 and may fill the opening OH.

[0101] refer to 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 be areas in which light generated by the respective light emitting elements ED-1, ED-2, and ED-3 is emitted. The light emitting areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other on a plane.

[0102] Each of the light-emitting areas PXA-R, PXA-G, and PXA-B may be an area separated by a pixel defining layer PDL. The non-light-emitting area NPXA may be an area between adjacent light-emitting areas PXA-R, PXA-G, and PXA-B, which corresponds to the pixel defining layer PDL. In some embodiments, the light-emitting areas PXA-R, PXA-G, and PXA-B may correspond to pixels, respectively. The pixel defining layer 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 in the opening OH defined in the pixel defining layer PDL and separated from each other.

[0103] The light emitting areas PXA-R, PXA-G, and PXA-B may be divided into a plurality of groups according to the colors of the lights generated by the light emitting elements ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In the display device DD of the embodiment illustrated in FIG, three light emitting areas PXA-R, PXA-G and PXA-B emitting red light, green light and blue light respectively are illustrated as examples. For example, the display device DD of the embodiment may include a red light emitting area PXA-R, a green light emitting area PXA-G and a blue light emitting area PXA-B separated from each other.

[0104] In the display device DD according to the embodiment, a plurality of light emitting elements ED-1, ED-2, and ED-3 may emit light beams 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. In some embodiments, 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.

[0105] However, the embodiments of the present disclosure are not limited thereto, and the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light beams in the same wavelength range, or at least one light-emitting element may emit a light beam in a wavelength range different from the others. For example, the first to third light-emitting elements ED-1, ED-2, and ED-3 may all emit blue light.

[0106] The light emitting areas PXA-R, PXA-G, and PXA-B in the display device DD according to the embodiment may be arranged in a stripe form. Figure 1 , a plurality of red light emitting areas PXA-R, a plurality of green light emitting areas PXA-G, and a plurality of blue light emitting areas PXA-B may be arranged along the second direction axis DR2, respectively. In addition, the red light emitting areas PXA-R, the green light emitting areas PXA-G, and the blue light emitting areas PXA-B may be alternately arranged in this order along the first direction axis DR1.

[0107] Figure 1 and Figure 2 It is illustrated that all the light-emitting regions PXA-R, PXA-G, and PXA-B have similar areas, but the embodiments of the present disclosure are not limited thereto. Therefore, the light-emitting regions PXA-R, PXA-G, and PXA-B may have different areas from each other according to the wavelength range of the emitted light. In this case, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may mean the areas when viewed on a plane defined by the first direction axis DR1 and the second direction axis DR2.

[0108] In some embodiments, the arrangement of the light-emitting areas PXA-R, PXA-G, and PXA-B is not limited to Figure 1 The configuration illustrated in FIG. 1 and the order in which the red light emitting areas PXA-R, the green light emitting areas PXA-G, and the blue light emitting areas PXA-B are arranged may be provided in various suitable combinations according to the characteristics of the display quality required or desired by the display device DD. For example, the arrangement form of the light emitting areas PXA-R, PXA-G, and PXA-B may be: Arrangement structure (eg, RGBG matrix, RGBG structure, or RGBG matrix structure) or DIAMOND Lay out the structure. It is an officially registered trademark of Samsung Display Co., Ltd.

[0109] In addition, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in the 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 embodiments of the present disclosure are not limited thereto.

[0110] In the following, Figures 3 to 7 1 is a cross-sectional view schematically illustrating a light emitting element according to the embodiment. Each of the light emitting elements ED according to the embodiment 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 sequentially stacked.

[0111] and Figure 3 compared to, Figure 4 A cross-sectional view of a light emitting element ED according to an embodiment is illustrated, 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 A cross-sectional view of a light emitting element ED according to an embodiment is illustrated, 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 3 compared to, Figure 6 A cross-sectional view of a light emitting element ED according to an embodiment is illustrated, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an emission auxiliary layer EAL, 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 7 A cross-sectional view of a light emitting element ED illustrating an embodiment including a cover layer CPL on the second electrode EL2 .

[0112] The first electrode EL1 has conductivity (e.g., electrical conductivity). The first electrode EL1 may be formed of a metal material, a metal alloy and / or a conductive compound (e.g., a conductive compound). The first electrode EL1 may be an anode or a cathode. However, the embodiments of the present disclosure are not limited thereto. In addition, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a semi-transmissive reflective electrode or a reflective electrode. The first electrode EL1 may include at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn and Zn, a compound selected from two or more of these, a mixture selected from two or more of these, or an oxide thereof.

[0113] 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), and / or indium tin zinc oxide (ITZO). If the first electrode EL1 is a semi-transmissive reflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, W, a compound or a mixture thereof (e.g., a mixture of Ag and Mg); or LiF / Ca (a stacking structure of LiF and Ca) or LiF / Al (a stacking structure of LiF and Al). In some embodiments, the first electrode EL1 may have a multilayer structure including a reflective film or a semi-transmissive reflective 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 embodiments of the present disclosure are not limited thereto. In addition, the embodiments of the present disclosure are not limited thereto, and the first electrode EL1 may include the metal material described above, a combination of at least two of the metal materials described above, an oxide of the metal material described above, etc. The thickness of the first electrode EL1 may be about 1000 Å. to about For example, the thickness of the first electrode EL1 may be about to about

[0114] The hole transport region HTR is 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, an emission auxiliary layer EAL, or an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 100 Å. to about The emission assistance layer EAL may be referred to as a buffer layer.

[0115] The hole transport region HTR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multi-layer structure including a plurality of layers formed of a plurality of different materials.

[0116] For example, 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 addition, the hole transport region HTR may have a single-layer structure formed of a plurality of different materials, or a structure in which hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / emission auxiliary layer EAL, hole injection layer HIL / emission auxiliary layer EAL, hole transport layer HTL / emission auxiliary layer EAL, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are sequentially stacked from the first electrode EL1, but the embodiments of the present disclosure are not limited thereto.

[0117] The hole transport region HTR may be formed using various suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and / or laser induced thermal imaging (LITI).

[0118] The hole transport region HTR may include the following compound represented by Formula H-1.

[0119] Formula H-1

[0120]

[0121] In the above formula H-1, L 1 and L 2 Each of a and b may be independently a direct bond, 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. a and b may be independently an integer from 0 to 10. In some embodiments, when a or b is an integer of 2 or greater, multiple L 1 and L 2 Each may 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.

[0122] In formula H-1, Ar 1 and Ar 2 Each of them 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. 3It 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.

[0123] The compound represented by the above formula H-1 may be a monoamine compound. In some embodiments, the compound represented by the above formula H-1 may be a diamine compound, wherein Ar 1 To Ar 3 At least one of them contains an amine group as a substituent. In addition, the compound represented by the above formula H-1 may be 1 and Ar 2 A carbazole-based compound including a substituted or unsubstituted carbazole group in at least one of Ar 1 and Ar 2 A fluorene-based compound including a substituted or unsubstituted fluorene group in at least one of the foregoing.

[0124] The compound represented by Formula H-1 may be represented by any one of the compounds in the following Compound Group H. However, the compounds listed in the following Compound Group H are examples, and the compound represented by Formula H-1 is not limited to those represented by the following Compound Group H.

[0125] Compound Group H

[0126]

[0127]

[0128] 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(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing 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.

[0129] The hole transport region HTR may include carbazole-based derivatives (e.g., N-phenylcarbazole and / or polyvinylcarbazole), fluorene-based derivatives, triphenylamine-based derivatives (e.g., N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) and / or 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA)), N,N'-di(naphthalene-l-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), 1,3-bis(N-carbazolyl)benzene (mCP), and the like.

[0130] In addition, 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.

[0131] The hole transport region HTR may include the compound of the hole transport region described above in at least one of the hole injection layer HIL, the hole transport layer HTL, the emission auxiliary layer EAL, and the electron blocking layer EBL.

[0132] The thickness of the hole transport region HTR may be about to about For example, about to about When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have, for example, 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 For example, 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-described ranges, suitable or satisfactory hole transport properties may be achieved without a significant increase in driving voltage.

[0133] In addition to the materials described above, the hole transport region HTR may further include a charge generating material to increase conductivity (e.g., electrical conductivity). The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may include at least one of a halogenated metal compound, a quinone derivative, a metal oxide, and a cyano group-containing compound, but the embodiments of the present disclosure are not limited thereto. For example, the p-dopant may include a metal halide compound such as CuI and / or RbI, a quinone derivative such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (F4-TCNQ)), a metal oxide such as tungsten oxide and / or molybdenum oxide, a cyano group-containing 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) and the like, but the embodiments of the present disclosure are not limited thereto.

[0134] 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 an auxiliary emission layer EAL and an electron blocking layer EBL. The auxiliary emission layer EAL may compensate for the resonance distance according to the wavelength of light emitted from the emission layer EML and may adjust the hole charge balance to increase the luminous efficiency. In addition, the auxiliary emission layer EAL may be used to prevent electrons from being injected into the hole transport region HTR. The material that may be included in the hole transport region HTR may be included in the auxiliary emission layer EAL. The electron blocking layer EBL is a layer for preventing or reducing electrons from being injected from the electron transport region ETR to the hole transport region HTR.

[0135] In the light-emitting element ED of the embodiment, the emission layer EML may include a first compound, which is an organic metal compound according to the embodiment. In addition, in the light-emitting element ED of the embodiment, in addition to the first compound, the emission layer EML may further include a second compound and a third compound as a host material. In the embodiment, the second compound may include a fused ring of three rings, which contains nitrogen atoms as ring atoms. The third compound may include a C6 ring group containing at least one nitrogen atom as a ring atom. In the light-emitting element ED of the embodiment, in addition to the first compound (which is an organic metal compound according to the embodiment), the emission layer EML may further include a fourth compound, which is a thermally activated delayed fluorescence dopant. The second compound to the fourth compound will be described in more detail below.

[0136] Herein, the first compound may be referred to as an organometallic compound of the embodiment. The organometallic compound of the embodiment may include Pt as a central metal atom, and one of the ligands bonded to the central metal atom may include a heteropolycyclic structure of the following formula A. In formula A, is a portion bonded to the central metal atom, and "-*" is a portion connected to each adjacent ligand. The heteropolycyclic structure represented by formula A may include a C5 ring containing O or S as a heteroatom in addition to a C6 ring containing a N atom. In the following formula A, W 1 To W 3 At least one of can be O or S.

[0137] Formula A

[0138]

[0139] The organometallic compound of the embodiment may further include a carbene derivative ligand and a pyridine derivative ligand in addition to the heteropolycyclic structure of Formula A above.

[0140] The organometallic compound of the embodiment includes a heteropolycyclic structure represented by Formula A, and thus can have a deep HOMO level, thereby obtaining a low driving voltage and a deep blue emission color. In addition, the organometallic compound of the embodiment can exhibit excellent luminous efficiency in a deep blue emission wavelength range.

[0141] The organometallic compound of the embodiment may be represented by Formula 1 below.

[0142] Formula 1

[0143]

[0144] In formula 1, W 1 To W 3At least one of them is O or S and the rest are CRa. Ra may be a hydrogen atom, a deuterium atom, a halogen atom, 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 oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 ring-forming carbon atoms, or bond to an adjacent group to form a ring.

[0145] In an embodiment, selected from W 1 To W 3 One of them can be O or S, or selected from W 1 To W 3 Two or more of may be independently O or S. When selected from W 1 To W 3 When two or more than two of the heteroatoms are O or S, the plurality of heteroatoms may all be the same or at least one may be different from the others.

[0146] For example, in the organometallic compound represented by Formula 1, W 1 Can be O or S, and W 2 and W 3 In some embodiments, when Ra is bonded to an adjacent group to form a ring, the formed ring may be a hydrocarbon ring or a heterocyclic ring. For example, the ring formed by combining with the adjacent group may be an aryl ring or a heteroaryl ring.

[0147] In formula 1, R 1 , R 2 and R 11 To R 26 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, 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 oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 ring-forming carbon atoms.

[0148] For example, in an embodiment, R 11 To R 26 and R and R are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. 1 and R 2Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0149] The organometallic compound of the embodiment is bonded to the central metal atom Pt, and includes 3- or 4-ring fused polycyclic heteropolycyclic as a ligand, and therefore can exhibit a deep HOMO (highest occupied molecular orbital) energy level. In addition, the inclusion of heteropolycyclic can provide excellent luminous efficiency and blue luminescent properties together. In addition, the organometallic compound of the embodiment can exhibit deep blue light emission with a relatively short wavelength.

[0150] The organometallic compound of the embodiment may emit phosphorescence (eg, may emit light by phosphorescence). The organometallic compound of the embodiment may be used as a phosphorescent dopant.

[0151] The organometallic compound of the embodiment represented by Formula 1 may be represented by the following Formula 1-1.

[0152] Formula 1-1

[0153]

[0154] In formula 1-1, W 11 Can be O or S. In addition, R a1 and R a2 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, 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 oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 ring-forming carbon atoms.

[0155] In an embodiment, R a1 and R a2 can be the same or different. For example, in Formula 1-1, R a1 and R a2 They can all be hydrogen atoms.

[0156] In some embodiments, in Formula 1-1, the above description of Formula 1 may also be applied to R 1 , R 2 and R 11 To R 26 .

[0157] The organometallic compound of the embodiment represented by Formula 1 may be represented by the following Formula 1-2.

[0158] Formula 1-2

[0159]

[0160] In formula 1-2, W 11 It may be O or S, and Cy may be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 3 to 30 ring carbon atoms.

[0161] In an embodiment, Cy may be a substituted or unsubstituted hexagonal hydrocarbon ring or a substituted or unsubstituted hexagonal heterocyclic ring. For example, Cy may be a substituted or unsubstituted benzene ring.

[0162] In some embodiments, in Formula 1-2, the above description of Formula 1 may also be applied to R 1 , R 2 and R 11 To R 26 .

[0163] The organometallic compound according to the embodiment may be represented by any one of the compounds in the following compound group 1. The light emitting element ED according to the embodiment may include at least one of the compounds in the following compound group 1. In the following compound group 1, D is a deuterium atom, and Ph is an unsubstituted phenyl group.

[0164] Compound Group 1

[0165]

[0166]

[0167]

[0168]

[0169]

[0170] The organometallic compound of the embodiment includes a heteropolycyclic ring that forms a 3- or 4-ring condensed ring, and the heteropolycyclic ring has the structure of the above-mentioned formula A, and thus can exhibit a deep HOMO energy level. For example, the organometallic compound of the embodiment can have a relatively lower HOMO energy level value than a compound having a polycyclic ring of a type (or species) different from the heteropolycyclic ring having the structure of formula A. For example, the organometallic compound in the embodiment can have a HOMO energy level of less than about -5.0 eV.

[0171] In addition, the light emitting element including the organic metal compound according to the embodiment can exhibit low driving voltage and high efficiency characteristics. In some embodiments, the light emitting element including the organic metal compound in the emission layer can emit blue light and also exhibit excellent light efficiency.

[0172] In the light-emitting element according to the embodiment, the emission layer EML may include a host and a dopant, and the organic metal compound of the embodiment may be included in the emission layer EML as a dopant. In the embodiment, the emission layer EML may include a phosphorescent dopant, and the phosphorescent dopant may include the organic metal compound of the embodiment. In some embodiments, the organic metal compound of the embodiment may emit phosphorescence (for example, light may be emitted by phosphorescence).

[0173] The organometallic compound of the embodiment can emit blue light. For example, the organometallic compound of the embodiment can be a luminescent material having a maximum emission wavelength in a wavelength range of about 440nm to about 470nm. In some embodiments, the organometallic compound of the embodiment can be a luminescent material having a maximum emission wavelength in a wavelength range of about 445nm to about 465nm.

[0174] In the embodiment, the emission layer EML may include the organic metal compound of the embodiment, and include at least one of the second to fourth compounds.

[0175] In the embodiment, the emission layer EML may further include a second compound represented by the following Formula HT-1. For example, the second compound may be used as a hole transport host material of the emission layer EML.

[0176] Formula HT-1

[0177]

[0178] In formula HT-1, A 1 To A 8 Can be N or CR independently 51 For example, A 1 To A 8 Can be CR 51 In some embodiments, A 1 To A 8 Any one of them can be N, and the rest can be CR 51 .

[0179] In formula HT-1, L 1 It may be a direct bond, 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.1 It may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent carbazole group, or the like, but embodiments of the present disclosure are not limited thereto.

[0180] In formula HT-1, Y a Can be direct key, CR 52 R 53 or SiR 54 R 55 That is, the two benzene rings connected to the nitrogen atom of formula HT-1 can be connected by a direct bond, In formula HT-1, when Y a When it is a direct bond, the second compound represented by Formula HT-1 may include a carbazole moiety, and -* refers to a position to be connected.

[0181] In formula HT-1, Ar 1 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. 1 It may be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted biphenyl group, etc., but the embodiments of the present disclosure are not limited thereto.

[0182] In formula HT-1, R 51 To R 55 and R and R are each 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms. In some embodiments, R 51 To R 55 Each may be bonded to an adjacent group to form a ring. For example, R 51 To R 55 R may each independently be a hydrogen atom or a deuterium atom. 51 To R 55 Each may independently be an unsubstituted methyl group or an unsubstituted phenyl group.

[0183] In the embodiment, the second compound represented by Formula HT-1 may be represented by any one of the compounds shown in the following Compound Group 2. The emission layer EML may include at least one of the compounds shown in the following Compound Group 2 as an electron transport host material.

[0184] Compound Group 2

[0185]

[0186]

[0187]

[0188]

[0189] In the example compounds presented in compound group 2, "D" may represent a deuterium atom, and "Ph" may represent a substituted or unsubstituted phenyl group. For example, in the example compounds presented in compound group 2, "Ph" may be an unsubstituted phenyl group.

[0190] In the embodiment, the emission layer EML may further include a third compound represented by the following Formula E-1. For example, the third compound may be used as an electron transport host material of the emission layer EML.

[0191] Formula ET-1

[0192]

[0193] In formula ET-1, X 1 To X 3 At least one of them may be N and the rest may be CR 56 For example, X 1 To X 3 Any one of them can be N, and the other two can each independently be CR 56 In this case, the third compound represented by Formula ET-1 may include a pyridine moiety. In some embodiments, X 1 To X 3 Two of them can be N and the remaining one can be CR 56 In this case, the third compound represented by Formula ET-1 may include a pyrimidine moiety. In some embodiments, X 1 To X 3 All may be N. In this case, the third compound represented by Formula ET-1 may include a triazine moiety.

[0194] In formula ET-1, R 56It 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.

[0195] In Formula ET-1, b1 to b3 may each independently be an integer of 0 to 10.

[0196] In formula ET-1, Ar 2 To Ar 4 Each of them may be independently 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. 2 To Ar 4 It may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazole group.

[0197] In formula ET-1, L 2 To L 4 and L may be independently a direct bond, 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. 2 To L 4 Each may 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.

[0198] In the embodiment, the third compound may be represented by any one of the compounds of the following compound group 3. The light emitting element ED according to the embodiment may include any one of the compounds of the following compound group 3.

[0199] Compound Group 3

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207] In the example compounds presented in Compound Group 3, "D" represents a deuterium atom, and "Ph" represents an unsubstituted phenyl group.

[0208] In addition to the first compound, the emission layer EML may further 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 hole transport host and the electron transport host may form an exciplex. In this case, the triplet energy level of the exciplex formed by the hole transport host and the electron transport host corresponds to 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.

[0209] For example, the triplet energy level (T1) of the exciplex formed by the hole transport host and the electron transport host may have an absolute value of about 2.4 eV to about 3.0 eV. In addition, the triplet energy level of the exciplex may have a value less than the band gap of each host material. The exciplex may have a triplet energy level of 3.0 eV or less, which is the band gap between the hole transport host and the electron transport host.

[0210] In the embodiment, the emission layer EML may further include a fourth compound represented by the following Formula F-1.

[0211] Formula F-1

[0212]

[0213] In formula F-1, A 1 and A 2 can be independently O, S, Se or NR m , and R m 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. 1a To R 11a Each is independently 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 is bonded to an adjacent group to form a ring.

[0214] In formula F-1, A 1 and A 2 can each independently bond to the substituents of the adjacent rings to form a fused ring. 1 and A 2 Each is independently NR m When A 1 Can be bonded to R 4a or R 5a To form a ring. In addition, A 2 Can be bonded to R 7a or R 8a to form a ring.

[0215] For example, the fourth compound represented by Formula F-1 may be included in the emission layer EML as a dopant. In an embodiment, the fourth compound represented by Formula F-1 may be a thermally activated delayed fluorescence dopant.

[0216] The fourth compound may be represented by any one of the compounds of the following compound group 4.

[0217] Compound Group 4

[0218]

[0219] In some embodiments, when the emission layer EML further includes the second to fourth compounds in addition to the first compound, the first compound, which is the organic metal compound of the embodiments, may be used as a phosphorescence sensitizer.

[0220] In the embodiment, the emission layer EML may include a first compound (which is an organic metal compound according to the embodiment), and at least one of the second compound to the fourth compound. For example, the light-emitting element ED of the embodiment may include all of the first compound, the second compound, the third compound, and the fourth compound, and the emission layer EML may therefore include a combination of two main materials and two dopant materials. In the light-emitting element ED of the embodiment, the emission layer EML includes the second compound and the third compound as two different main bodies, the fourth compound emitting delayed fluorescence, and the first compound as an organic metal complex, and therefore can exhibit excellent luminous efficiency.

[0221] For example, in the emission layer EML of the embodiment, the second compound and the third compound form an exciplex, and energy can be transferred from the exciplex to the first compound and the fourth compound to emit light. In the embodiment, the first compound can be a sensitizer. In the light-emitting element ED of the embodiment, the first compound contained in the emission layer EML can be used as a sensitizer to transfer energy from the host to the fourth compound as a thermally activated delayed fluorescent dopant. In some embodiments, the first compound as an auxiliary dopant can accelerate the energy transfer to the fourth compound used as a light-emitting dopant, thereby increasing the light emission ratio of the fourth compound.

[0222] In some embodiments, the emission layer EML may include the first compound as an organic metal compound and the fourth compound as a thermally activated delayed fluorescence dopant, or the emission layer EML may include the first compound as an organic metal compound and the second and third compounds as host materials.

[0223] When the emission layer EML in the light emitting element ED according to the embodiment includes the first, second and third compounds, the amount of the second and third compounds may be about 65 wt % to about 95 wt % relative to the total weight of the first, second and third compounds.

[0224] The weight ratio of the second compound to the third compound may be about 3:7 to about 7:3 relative to the total weight of the second compound and the third compound. When the amount of the second compound and the third compound satisfies the ratio described above, the charge balance in the emission layer EML may be improved, thereby increasing the luminous efficiency and the service life of the element. When the amount of the second compound and the third compound is outside the ratio range described above, the charge balance in the emission layer EML may be destroyed, thereby reducing the luminous efficiency and easily degrading the element.

[0225] The emission layer EML may have, for example, approximately to about or about to about The emission layer EML may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multilayer structure having a plurality of layers formed of a plurality of different materials.

[0226] exist Figures 3 to 7 In the light emitting element ED of the embodiment shown in FIG. 1 , the emission layer EML may contain the organic metal compound of the above embodiment as a dopant. Figures 3 to 7In the light-emitting element ED of the embodiment shown in , the emission layer EML may include a first compound (which is an organic metal compound of the embodiment), and at least one of a second compound represented by formula HT-1 and a third compound represented by formula ET-1. Figures 3 to 7 In the light-emitting element ED of the embodiment shown in , the emission layer EML may include a first compound (which is the organic metal compound of the embodiment), a second compound represented by formula HT-1, a third compound represented by formula ET-1, and a fourth compound represented by formula F-1.

[0227] In the light emitting element ED of the embodiment, the emission layer EML may further include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, In some embodiments, the emission layer EML may further include anthracene derivatives and / or pyrene derivatives.

[0228] exist Figures 3 to 7 In each of the light emitting elements ED of the embodiment illustrated in , the emission layer EML may further include a host and a dopant, and for example, the emission layer EML may further include a compound represented by the following Formula E-1.

[0229] Formula E-1

[0230]

[0231] In formula E-1, R 31 To R 40 may each 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-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. In some embodiments, R 31 To R 40 It may be bonded to an adjacent group to form a saturated hydrocarbon ring or an unsaturated hydrocarbon ring, a saturated heterocyclic ring or an unsaturated heterocyclic ring.

[0232] In Formula E-1, c and d may each independently be an integer of 0 to 5.

[0233] The compound represented by Formula E-1 may be represented by any one of the following Compound E1 to Compound E19.

[0234]

[0235]

[0236] In the embodiment, the emission layer EML may further include a compound represented by the following Formula E-2a or Formula E-2b. The compound represented by the following Formula E-2a or Formula E-2b may be used as a phosphorescent host material.

[0237] Formula E-2a

[0238]

[0239] In Formula E-2a, a may be an integer from 0 to 10, and L a It may be a direct bond, 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 some embodiments, when a is an integer of 2 or greater, multiple L a Each may 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.

[0240] In addition, in formula E-2a, A 1 To A 5 Can be N or CR independently i . R a To R i Each may independently be 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 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-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. a To R i It may be bonded to an adjacent group to form a hydrocarbon ring or a heterocyclic ring containing N, O, S, etc. as a ring-constituting atom.

[0241] In some embodiments, in Formula E-2a, selected from A 1 To A 5 Two or three of them can be N, and the rest can be CR i .

[0242] Formula E-2b

[0243]

[0244] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 ring carbon atoms. b is a direct bond, 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 some embodiments, b is an integer from 0 to 10, and when b is an integer of 2 or greater, multiple L b Each may 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.

[0245] The compound represented by formula E-2a or formula E-2b can be represented by any one of the compounds of the following compound group E-2. However, the compounds listed in the following compound group E-2 are examples, and the compounds represented by formula E-2a or formula E-2b are not limited to those presented in the following compound group E-2.

[0246] Compound Group E-2

[0247]

[0248]

[0249]

[0250] The emission layer EML may include a compound represented by the following Formula Ma. The compound represented by the following Formula Ma may be used as a phosphorescent dopant material.

[0251] Formula Ma

[0252]

[0253] In the above formula Ma, Y 1 To Y 4 and Z 1 To Z 4 Can be CR independently 1 or N, R 1 To R 4Each independently may be 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 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-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. In formula Ma, m is 0 or 1, and n is 2 or 3. In formula Ma, when m is 0, n is 3, or when m is 1, n is 2.

[0254] The compound represented by the formula Ma may be used as a phosphorescent dopant.

[0255] The compound represented by the formula Ma may be represented by any one of the following compounds M-a1 to M-a25. However, the following compounds M-a1 to M-a25 are examples, and the compound represented by the formula Ma is not limited to those represented by the following compounds M-a1 to M-a25.

[0256]

[0257]

[0258] The emission layer EML may further include a compound represented by any one of the following Formulae Fa to Fc. The compounds represented by the following Formulae Fa to Fc may be used as a fluorescent dopant material.

[0259] Formula

[0260]

[0261] In the above formula Fa, R a To R j The two of them can be independently *-NAr 1 Ar 2 Replace. a To R j Unrecognized*-NAr 1 Ar 2 The remainder of the substitution may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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. -* refers to the position to be connected.

[0262] In *-NAr 1 Ar2 in Ar 1 and Ar 2 Each of them 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 may be a heteroaryl group containing O or S as a ring-forming atom.

[0263] Formula Fb

[0264]

[0265] In the above formula Fb, R a and R b 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 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, or may be bonded to an adjacent group to form a ring. Ar 1 To Ar 4 Each may independently 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.

[0266] In Formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms. 1 To Ar 4 At least one of may be a heteroaryl group containing O or S as a ring-forming atom.

[0267] In formula Fb, the number of rings represented by U and V can be 0 or 1 independently of each other. For example, in formula Fb, it means that when the number of U or V is 1, one ring constitutes a fused ring at the portion indicated by U or V, and when the number of U or V is 0, there is no ring indicated by U or V. Specifically, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the fused ring with fluorene core in formula Fb can be a cyclic compound with four rings. In addition, when each number of U and V is 0, the fused ring with fluorene core in formula Fb can be a cyclic compound with three rings. In addition, when each number of U and V is 1, the fused ring with fluorene core in formula Fb can be a cyclic compound with five rings.

[0268] Formula Fc

[0269]

[0270] In Formula Fc, A 1 and A 2 can be independently O, S, Se or NR m , and R m 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 R 11 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boryl 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 is bonded to an adjacent group to form a ring.

[0271] In Formula Fc, A 1 and A 2 can each independently bond to the substituents of the adjacent rings to form a fused ring. 1 and A 2 Each is independently NR m When A 1 Can be bonded to R 4 or R 5 To form a ring. In some embodiments, A 2 Can be bonded to R 7 or R 8 to form a ring.

[0272] In an embodiment, the emission layer EML may further include a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]phenylene (DPAVB), and N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-2-yl)vinyl) As dopant materials, 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and / or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and / or its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene) and the like can be used.

[0273] The emission layer EML may further include any suitable phosphorescent dopant material generally available in the art. For example, a metal complex comprising iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm) may be used as a phosphorescent dopant. In some embodiments, bis(4,6-difluorophenylpyridinyl-N,C2') picolinate iridium (III) (FIrpic), bis(2,4-difluorophenylpyridinyl)-tetra(1-pyrazolyl) borate iridium (III) (FIr6) and / or octaethylporphyrin platinum (PtOEP) may be used as a phosphorescent dopant. However, the embodiments of the present disclosure are not limited thereto.

[0274] The emission layer EML may include a quantum dot material. The core of the quantum dot may be selected from II-VI group compounds, I-II-VI group compounds, II-IV-VI group compounds, I-II-IV-VI group compounds, II-IV-V group compounds, III-VI group compounds, I-III-VI group compounds, III-V group compounds, III-II-V group compounds, IV-VI group compounds, IV group elements, IV group compounds, and combinations thereof.

[0275] The II-VI compound may be selected from the group consisting of a binary compound selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; a ternary compound selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS , CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and mixtures thereof.

[0276] III-VI compounds may include binary compounds such as In 2 S 3 and / or In 2 Se 3 , ternary compounds such as InGaS 3 and / or InGaSe 3 , or any combination thereof.

[0277] The I-III-VI group compound may be selected from: a ternary compound selected from AgInS, AgInS 2 、CuInS、CuInS 2 、AgGaS 2 、CuGaS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 and mixtures thereof; and / or quaternary compounds such as AgInGaS 2 and / or CuInGaS 2 .

[0278] The III-V compound may be selected from the group consisting of: a binary compound selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb and a mixture 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 a mixture thereof; and 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 a mixture thereof. In some embodiments, the III-V group compound may further include a II group metal. For example, InZnP or the like may be selected as the III-II-V group compound.

[0279] The IV-VI compound may be selected from the group consisting of: a binary compound selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; a ternary compound selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and a quaternary compound selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. The IV group element may be selected from the group consisting of Si, Ge, and mixtures thereof. The IV group compound may be a binary compound selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0280] Each element contained in a multi-component compound (e.g., a binary compound, a ternary compound, or a quaternary compound) may be present in the particle in a uniform or non-uniform concentration distribution. In some embodiments, the formula refers to the type (or kind) of element contained in the compound, and the ratio of elements in the compound may be different. For example, AgInGaS 2 Can mean AgIn x Ga 1-x S 2 (where x is a real number between 0 and 1).

[0281] In some embodiments, the quantum dot may have a single structure or a core-shell dual structure, wherein the concentration of each element contained in the quantum dot is uniform. For example, the material contained in the core may be different from the material contained in the shell.

[0282] The shell of the quantum dot can act as a protective layer to prevent or reduce chemical denaturation of the core to maintain semiconductor properties, and / or can act 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 becomes lower along the direction toward the center of the core.

[0283] Examples of quantum dot shells may include metal and / or non-metal oxides, semiconductor compounds, or combinations thereof. For example, metal or non-metal oxides may be binary compounds (e.g., 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 / or NiO), and / or ternary compounds (such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 and / or CoMn 2 O 4 ), but the embodiments of the present disclosure are not limited thereto.

[0284] In addition, 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 the embodiments of the present disclosure are not limited thereto.

[0285] The quantum dots may have a full width at half maximum (FWHM) of an emission wavelength spectrum of about 45 nm or less, preferably about 40 nm or less, and more preferably about 30 nm or less, and within the above range, color purity or color reproducibility may be improved. In addition, light emitted by such quantum dots is emitted in all (e.g., substantially all) directions, and thus a wide viewing angle may be improved.

[0286] In addition, although the form of quantum dots is not particularly limited as long as it is a form commonly used in the art, for example, quantum dots in the form of spherical, pyramidal, multi-arm and / or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc. can be used.

[0287] When adjusting the size of the quantum dot or adjusting the ratio of elements in the quantum dot compound, the band gap can be controlled, and therefore light in various suitable wavelength ranges can be obtained in the quantum dot emission layer. Therefore, quantum dots as described above are used (using different sizes of quantum dots or different ratios of elements in quantum dot compounds), and therefore a light-emitting element emitting light of various suitable wavelengths can be realized. In some embodiments, the size of the quantum dot or the adjustment of the ratio of elements in the quantum dot compound can be selected to emit red light, green light and / or blue light. In addition, quantum dots can be configured to emit white light by combining various suitable colors of light.

[0288] exist Figures 3 to 7 In each of the light emitting elements ED of the embodiment illustrated in , an electron transport region ETR is 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 embodiments of the present disclosure are not limited thereto.

[0289] The electron transport region ETR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multilayer structure including a plurality of layers formed of a plurality of different materials.

[0290] 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, and may have a single-layer structure formed of an electron injection material and an electron transport material. In addition, the electron transport region ETR may have a single-layer structure formed of a plurality of different materials, or may have a structure in which an electron transport layer ETL / electron injection layer EIL, a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL are stacked in order from the emission layer EML, but the embodiments of the present disclosure are not limited thereto. The electron transport region ETR may have, for example, about to about Thickness.

[0291] The electron transport region ETR may be formed using various suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing and / or laser induced thermal imaging (LITI) method.

[0292] The electron transport region ETR may include a compound represented by the following Formula ET-2.

[0293] Formula ET-2

[0294]

[0295] In formula ET-2, X 1 To X 3 At least one of them is N and the rest are CR a . 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.

[0296] In Formula ET-2, a to c may each independently be an integer from 0 to 10. In Formula ET-2, L 1 To L 3 Each of a to c is independently a direct bond, 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 some embodiments, when a to c are each independently an integer of 2 or greater, L 1 To L 3 Each may 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.

[0297] The electron transport region ETR may include an anthracene-based compound. However, the embodiments of the present disclosure are not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinolinato)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 (Bp hen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-ato)aluminum (BAlq), bis(benzoquinolinolato-10-atoberyllium) (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB) or a mixture thereof.

[0298] The electron transport region ETR may include at least one of the following compounds ET1 to ET36.

[0299]

[0300]

[0301]

[0302]

[0303] In addition, the electron transport region ETR may include metal halides (e.g., LiF, NaCl, CsF, RbCl, RbI, CuI, and KI), lanthanide metals (e.g., Yb), and co-deposited materials of metal halides and lanthanide metals. For example, the electron transport region ETR may include KI:Yb, RbI:Yb, LiF:Yb, etc. as co-deposited materials. In some embodiments, the electron transport region ETR may use materials such as Li 2O and / or BaO metal oxide and / or 8-hydroxy-quinoline lithium (Liq) etc. are formed, but the embodiments of the present disclosure are not limited thereto. The electron transport region ETR can also be formed by a mixture material of an electron transport material and an insulating organic metal salt (e.g., an electrically insulating organic metal salt). The organic metal salt can be a material having an energy band gap of about 4 eV or greater than 4 eV. In some embodiments, the organic metal salt may include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates and / or metal stearates.

[0304] In addition to the materials described above, 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 embodiments of the present disclosure are not limited thereto.

[0305] The electron transport region ETR may include the compound of the electron transport region ETR described above in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

[0306] 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, about to about If the thickness of the electron transport layer ETL satisfies the above range, suitable or 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, about to about If the thickness of the electron injection layer EIL satisfies the above-described range, suitable or satisfactory electron injection characteristics may be obtained without a significant increase in driving voltage.

[0307] The second electrode EL2 is 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 embodiments of the present disclosure are 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.

[0308] The second electrode EL2 may be a transmissive electrode, a semi-transmissive reflective 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 (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.).

[0309] When the second electrode EL2 is a semi-transmissive reflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, Yb, W, or a compound or mixture thereof (e.g., AgMg, AgYb and / or MgYb); or LiF / Ca or LiF / Al. In some embodiments, the second electrode EL2 may have a multilayer structure including a reflective film or a semi-transmissive reflective 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, an oxide of the above metal materials, etc.

[0310] In some embodiments, the second electrode EL2 may be connected to an auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the impedance (eg, resistance) of the second electrode EL2 may be reduced.

[0311] In some embodiments, a cover layer CPL may be further on the second electrode EL2 of the light emitting element ED of the embodiments. The cover layer CPL may include a plurality of layers or a single layer.

[0312] In an embodiment, the capping layer CPL may be 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.

[0313] For example, when the capping layer CPL includes an organic material, the organic material may include 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., and / or epoxy resin, and / or acrylate, such as methacrylate. However, the embodiments of the present disclosure are not limited thereto, and the cover layer CPL may include at least one of the following compounds P1 to P5.

[0314]

[0315] In some embodiments, the refractive index of the cover layer CPL may be about 1.6 or greater. In some embodiments, the refractive index of the cover layer CPL may be about 1.6 or greater with respect to light in a wavelength range of about 550 nm to about 660 nm.

[0316] Figures 8 to 11 Each of them is a cross-sectional view of a display device according to an embodiment of the present disclosure. Figures 8 to 11 When describing the display device of the embodiment, the description of the Figures 1 to 7 Instead of describing the repeated features, their differences will be mainly described.

[0317] refer to Figure 8 According to the embodiment, the display device DD-a may include a display panel DP including a display element layer DP-ED, a light control layer CCL and a color filter layer CFL disposed on the display panel DP. Figure 8 In the embodiment illustrated in FIG. 4 , the display panel DP may include a base layer BS, a circuit layer DP-CL and a display element layer DP-ED on the base layer BS, and the display element layer DP-ED may include a light emitting element ED.

[0318] The light emitting element ED may include a first electrode EL1, a hole transport region HTR on the first electrode EL1, an emission layer EML disposed on the hole transport region HTR, an electron transport region ETR on the emission layer EML, and a second electrode EL2 on the electron transport region ETR. Figures 3 to 7 The structure of the light emitting element can be similarly applied to Figure 8 The structure of the light-emitting element ED is illustrated in FIG. Figure 8 The light emitting element ED shown in the embodiment may include the organic metal compound of the embodiment. Therefore, the light emitting element ED may exhibit improved luminous efficiency and low driving voltage characteristics. In addition, the light emitting element ED may emit deep blue light and exhibit excellent color conversion efficiency.

[0319] refer to Figure 8 , the emission layer EML may be in the opening OH defined in the pixel defining layer PDL. For example, the emission layer EML provided corresponding to each light emitting area PXA-R, PXA-G, and PXA-B separated by the pixel defining layer PDL may emit light in the same wavelength range. In the display device DD-a of the embodiment, the emission layer EML may emit blue light. In some embodiments, the emission layer EML may be provided as a common layer in the entire light emitting area PXA-R, PXA-G, and PXA-B.

[0320] The light control layer CCL may be on the display panel DP. The light control layer CCL may include a light converter. The light converter may be a quantum dot, a phosphor, etc. The light converter may emit the provided light by converting its wavelength. In some embodiments, the light control layer CCL may include a layer including quantum dots and / or a layer including a phosphor.

[0321] The light-control layer CCL may include a plurality of light-control parts CCP1, CCP2, and CCP3. The light-control parts CCP1, CCP2, and CCP3 may be spaced apart from each other.

[0322] refer to Figure 8 , the separated pattern BMP may be between the light control parts CCP1 , CCP2 , and CCP3 that are spaced apart from each other, but embodiments of the present disclosure are not limited thereto. Figure 8 It is illustrated that the separated pattern BMP does not overlap the light control parts CCP1 , CCP2 , and CCP3 , but at least a portion of the edges of the light control parts CCP1 , CCP2 , and CCP3 may overlap the separated pattern BMP.

[0323] The light control layer CCL may include: a first light control component CCP1 containing first quantum dots QD1 that convert the first color light provided by the light emitting element ED into second color light, a second light control component CCP2 containing second quantum dots QD2 that convert the first color light into third color light, and a third light control component CCP3 that transmits the first color light.

[0324] 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 as the first color light provided by 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. With respect to quantum dots QD1 and QD2, the same contents as described above may apply.

[0325] In addition, the light control layer CCL may further include a scatterer SP (e.g., a light scatterer SP). The first light control component CCP1 may include a first quantum dot QD1 and a scatterer SP, the second light control component CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third light control component CCP3 may not include any quantum dot but include a scatterer SP.

[0326] The scatterer SP may be inorganic particles. For example, the scatterer SP may include TiO 2 、ZnO、Al 2 O 3 、SiO2 and hollow spherical silica. The scatterer SP may include TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow spherical silica, or may be selected from TiO 2 、ZnO、Al 2 O 3 、SiO 2 and a mixture of at least two of the materials selected from hollow spherical silica.

[0327] The first light control component CCP1, the second light control component CCP2, and the third light control component CCP3 may each include matrix resins BR1, BR2, and BR3 in which quantum dots QD1 and QD2 and scatterers SP are dispersed. In an embodiment, the first light control component CCP1 may include first quantum dots QD1 and scatterers SP dispersed in a first matrix resin BR1, the second light control component CCP2 may include second quantum dots QD2 and scatterers SP dispersed in a second matrix resin BR2, and the third light control component CCP3 may include scatterers SP dispersed in a third matrix resin BR3.

[0328] The matrix resins BR1, BR2 and BR3 are the medium in which the quantum dots QD1 and QD2 and the scatterers SP are dispersed, and can be formed by various suitable resin compositions that can be generally referred to as adhesives. For example, the matrix resins BR1, BR2 and BR3 can be acrylic-based resins, urethane-based resins, silicone-based resins, epoxy-based resins, etc. The matrix resins BR1, BR2 and BR3 can be transparent resins. In an embodiment, the first matrix resin BR1, the second matrix resin BR2 and the third matrix resin BR3 can be the same or different from each other.

[0329] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 may play a role in preventing or reducing the penetration of moisture and / or oxygen (hereinafter, referred to as "moisture / oxygen"). The barrier layer BFL1 may block or reduce the exposure of the light control components CCP1, CCP2, and CCP3 to moisture / oxygen. In some embodiments, the barrier layer BFL1 may cover the light control components CCP1, CCP2, and CCP3. In addition, the barrier layer BFL2 may be between the light control components CCP1, CCP2, and CCP3 and the color filter layer CFL.

[0330] The barrier layers BFL1 and BFL2 may include at least one inorganic layer. In some embodiments, the barrier layers BFL1 and BFL2 may include inorganic materials. For example, the barrier layers BFL1 and BFL2 may 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 transmittance, etc. In some embodiments, the barrier layers BFL1 and BFL2 may further include an organic film. The barrier layers BFL1 and BFL2 may be formed by a single layer or multiple layers.

[0331] In the display device DD-a of the embodiment, the color filter layer CFL may be on the light-controlling layer CCL. For example, the color filter layer CFL may be directly on the light-controlling layer CCL. In this case, the blocking layer BFL2 may be omitted.

[0332] The color filter layer CFL may include filters CF1, CF2, and CF3. The color filter layer CFL may include a first filter CF1 configured to transmit a second color light, a second filter CF2 configured to transmit a third color light, and a third filter CF3 configured to transmit 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 and / or dye. The first filter CF1 may include a red pigment and / or dye, the second filter CF2 may include a green pigment and / or dye, and the third filter CF3 may include a blue pigment and / or dye.

[0333] However, the embodiments of the present disclosure are 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.

[0334] Furthermore, in the embodiment, the first filter CF1 and the second filter CF2 may be yellow filters. The first filter CF1 and the second filter CF2 may not be separated but provided as one filter.

[0335] In some embodiments, the color filter layer CFL may further include a light shielding member. The light shielding member may be a black matrix. The light shielding member may include an organic light shielding material or an inorganic light shielding material including a black pigment and / or dye. The light shielding member may prevent or reduce light leakage and may separate the boundaries between adjacent filters CF1, CF2, and CF3. In addition, in an embodiment, the light shielding member may be formed by a blue filter.

[0336] The first to third filters CF1 , CF2 , and CF3 may be provided corresponding to the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B, respectively.

[0337] The base substrate BL may be on the color filter layer CFL. The base substrate BL may be a member providing a base surface in which the color filter layer CFL, the light control layer CCL, etc. are provided. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or an organic-inorganic composite material layer. In some embodiments, the base substrate BL may be omitted.

[0338] Fig. 9 is a cross-sectional view showing a portion of a display device according to an embodiment. In the display device DD-TD of the embodiment, the light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. At least one of the plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 may contain the organic metal compound of the embodiment. Therefore, the light-emitting element ED-BT may exhibit improved luminous efficiency and low driving voltage characteristics. In addition, the light-emitting element ED-BT may emit deep blue light and exhibit excellent color conversion efficiency.

[0339] The light emitting element ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other, and a plurality of light emitting structures OL-B1, OL-B2, and OL-B3 sequentially stacked in a thickness direction between the first electrode EL1 and the second electrode EL2. Each of the light emitting structures OL-B1, OL-B2, and OL-B3 may include an emission layer EML ( Figure 8 ) and the emission layer EML, with the hole transport region HTR and the electron transport region ETR ( Figure 8 ). In some embodiments, the light emitting elements ED-BT included in the display devices DD-TD of the embodiments may be light emitting elements having a tandem structure and including a plurality of emission layers.

[0340] exist Fig. 9 In the embodiment illustrated in , all the light beams emitted by the light emitting structures OL-B1, OL-B2 and OL-B3 respectively may be blue light. However, the embodiments of the present disclosure are not limited thereto, and the light beams emitted by the light emitting structures OL-B1, OL-B2 and OL-B3 respectively may have wavelength ranges different from each other. For example, the light emitting element ED-BT including a plurality of light emitting structures OL-B1, OL-B2 and OL-B3 emitting light beams having wavelength ranges different from each other may emit white light.

[0341] The charge generation layer CGL may be between adjacent light emitting structures OL-B1, OL-B2, and OL-B3. The charge generation layer CGL may include a p-type charge generation layer and / or an n-type charge generation layer.

[0342] refer to Fig.10 , 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. At least one of the light-emitting elements ED-1, ED-2 and ED-3 may contain the organic metal compound of the embodiment. Therefore, the light-emitting elements ED-1, ED-2 and ED-3 may exhibit improved luminous efficiency and low driving voltage characteristics. In addition, the light-emitting elements ED-1, ED-2 and ED-3 may emit deep blue light and exhibit excellent color conversion efficiency.

[0343] and Figure 2 Compared with the display device DD of the embodiment illustrated in FIG. Fig.10 The difference of the embodiment illustrated in 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 region.

[0344] 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. In addition, 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 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.

[0345] The emission auxiliary component OG may include a single layer or a multilayer. The emission auxiliary component OG may include a charge generation layer. In some embodiments, the emission auxiliary component OG may include an electron transport region, a charge generation layer, and a hole transport region stacked in sequence. The emission auxiliary component OG may be provided as a common layer in all the first to third light-emitting elements ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto, and the emission auxiliary component OG may be provided by patterning in an opening OH defined in a pixel defining layer PDL.

[0346] 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 electron transport region ETR and the emission auxiliary component OG. 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 emission auxiliary component OG and the hole transport region HTR.

[0347] In some embodiments, 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 sequence. 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 sequence. 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 sequence.

[0348] In some embodiments, the optical auxiliary layer PL may be on the display element layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be on the display panel DP and control reflected light due to external light in the display panel DP. In some embodiments, the optical auxiliary layer PL in the display device according to the embodiment may be omitted.

[0349] and Fig. 9 and Fig.10 The difference is, Fig.11 The display device DD-c is illustrated as including four light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1. The light emitting element ED-BT 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 sequentially stacked in the thickness direction between the first electrode EL1 and the second electrode EL2. At least one of the first to fourth light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1 may include the organic metal compound of the embodiment. Therefore, the light emitting element ED-CT may exhibit improved luminous efficiency and low driving voltage characteristics. In addition, the light emitting element ED-CT may emit deep blue light and exhibit excellent color conversion efficiency.

[0350] The charge generation layers CGL1, CGL2, and CGL3 may be between the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. Among the four light emitting structures, the first to third light emitting structures OL-B1, OL-B2, and OL-B3 may emit blue light, and the fourth light emitting structure OL-C1 may emit green light. However, the embodiments of the present disclosure are not limited thereto, and the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light in different wavelength regions. The charge generation layers CGL1, CGL2, and CGL3 disposed between adjacent light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may include a p-type charge generation layer and / or an n-type charge generation layer.

[0351] In an embodiment, the electronic device may include a display device including a plurality of light emitting elements, and a control unit for controlling the display device. The electronic device of the embodiment may be a device activated according to an electrical signal. The electronic device may include the display device of various embodiments. For example, the electronic device may include not only large electronic devices (such as televisions, monitors and / or outdoor billboards), but also small electronic devices and medium-sized electronic devices (such as personal computers, laptop computers, personal digital terminals, display devices for vehicles, game consoles, portable electronic devices and / or cameras).

[0352] Fig.12 is a view illustrating 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 include a Figure 1 and Figure 2 as well as Figures 8 to 11 The described display devices DD, DD-TD, DD-a, DD-b and DD-c have the same configuration.

[0353] Fig.12The vehicle AM ​​is illustrated, but this is an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may be in another means of transportation (e.g., a bicycle, a motorcycle, a train, a ship, and / or an airplane). In addition, at least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 including the same configuration as the display devices DD, DD-TD, DD-a, DD-b, and DD-c of the embodiment may be used in a personal computer, a laptop computer, a personal digital terminal, a game console, a portable electronic device, a television, a monitor, an outdoor billboard, etc. In addition, these are provided only as embodiments, and therefore may be used in other suitable electronic devices, unless departing from the spirit and scope of the present disclosure.

[0354] At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a reference Figures 3 to 7 At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include the organic metal compound of the embodiment. Therefore, the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may have improved display quality.

[0355] refer to Fig.12 , the vehicle AM ​​may include a steering wheel HA and a gear member GR for driving the vehicle AM. In addition, the vehicle AM ​​may include a front window GL provided to face the driver.

[0356] The first display device DD-1 may be in a first area overlapping with the steering wheel HA. For example, the first display device DD-1 may be a digital cluster component that displays first information of the vehicle AM. The first information may include a first scale indicating the travel speed of the vehicle AM, a second scale indicating the engine speed (i.e., revolutions per minute (RPM)), an image indicating the fuel status, etc. The first scale and the second scale may be represented as digital images.

[0357] The second display device DD-2 can be in the second zone facing the driver's seat and overlapping with the front window GL. The driver's seat can be a seat in which a steering wheel HA is provided. For example, the second display device DD-2 can be a head-up display (HUD) showing the second information of the vehicle AM. The second display device DD-2 can be optically transparent. The second information can include a digital number indicating the driving speed, and can further include information such as the current time. In some embodiments, the second information of the second display device DD-2 can be projected onto the front window GL to be displayed.

[0358] The third display device DD-3 may be in a third zone adjacent to the gear member GR. For example, the third display device DD-3 may be between the driver's seat and the passenger seat and may be a central information display (CID) of a vehicle for displaying the third information. The passenger seat may be a seat spaced apart from the driver's seat, with the gear member GR in between. The third information may include information about traffic (e.g., navigation information), playing music and / or broadcasting and / or video (or images), the temperature inside the vehicle AM, etc.

[0359] The fourth display device DD-4 may be spaced apart from the steering wheel HA and the shift member GR, and may be in a fourth zone adjacent to the 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 of the outside of the vehicle AM ​​captured by a camera module CM outside the vehicle AM. The fourth information may include an image of the outside of the vehicle AM.

[0360] The above-mentioned first to fourth information may be examples, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may further display information about the interior and exterior of the vehicle AM. The first to fourth information may include different information. However, the embodiments of the present disclosure are not limited thereto, and a portion of the first to fourth information may include the same information as each other.

[0361] Hereinafter, the organometallic compound and the light emitting element of the embodiment of the present disclosure will be further described with reference to Examples and Comparative Examples.In addition, the examples shown below are only exemplified for understanding the subject matter of the present disclosure, and the scope of the present disclosure is not limited thereto.

[0362] Example

[0363] 1. Synthesis of Organometallic Compounds of Examples

[0364] The method of synthesizing the organometallic compound according to the embodiment of the present disclosure will be described in more detail by presenting a method of synthesizing Compound 9, Compound 29, Compound 31, Compound 38, Compound 43, Compound 45, Compound 53, Compound 60, Compound 73, and Compound 81 as examples. In addition, the method of synthesizing the organometallic compound described hereinafter is provided as an example, and thus the method of synthesizing the compound according to the embodiment of the present disclosure is not limited to the following examples.

[0365] (1) Synthesis of Compound 9

[0366] The organometallic compound 9 according to the embodiment may be synthesized by, for example, the method of the following Reaction Formula 1.

[0367] Reaction 1

[0368]

[0369] Synthesis of intermediate 9-1

[0370] 6-methoxy-9-phenyl-4,9-dihydrothieno[3,2,b]quinoline (5.3 g, 18 mmol), 2-bromo-4(tert-butyl)pyridine (5.8 g, 27 mmol), tripotassium phosphate (8.3 g, 36 mmol), CuI (0.66 g, 3.6 mmol) and picolinic acid (0.4 g, 3.6 mmol) were placed in a reaction vessel and suspended in dimethyl sulfoxide (100 mL). The resulting reaction mixture was heated and stirred at 160 ° C for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water (100 mL) was added thereto, and the resulting mixture was then extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (5.8 g, 13.7 mmol).

[0371] Synthesis of intermediate 9-2

[0372] Intermediate 9-1 (5.8g, 13.7mmol) is suspended in an excess of hydrobromic acid solution. The resulting reaction mixture is heated and stirred at 110°C for 24 hours. After the reaction is complete, the mixture is cooled to room temperature and neutralized by adding an appropriate amount of sodium bicarbonate. Distilled water (100mL) is added thereto, and then the mixture obtained is extracted with ethyl acetate. The extracted organic layer is washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (4.6g, 11.1mmol).

[0373] Synthesis of intermediate 9-3

[0374] Intermediate 9-2 (4.6g, 11.1mmol), 1-bromo-3-fluorobenzene (2.9g, 16.7mmol) and tripotassium phosphate (5.2g, 22.2mmol) are placed in a reaction vessel and suspended in dimethyl sulfoxide (100mL). The resulting reaction mixture is heated and stirred at 160°C for 12 hours. After the reaction is complete, the mixture is cooled to room temperature, distilled water (100mL) is added thereto, and then the mixture obtained is extracted with ethyl acetate. The extracted organic layer is washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (5.2g, 9.2mmol).

[0375] Synthesis of intermediate 9-4

[0376] Intermediate 9-3 (5.2 g, 9.2 mmol), N1-([1,1:3',1"-terphenyl]-2'-yl)benzene-1,2-diamine (3.1 g, 9.2 mmol), SPhos (0.70 mmol), Pd 2 (dba) 3 4-nitropropene (0.46mmol) and sodium tert-butoxide (18mmol) are suspended in toluene solvent (100ml), and then the mixture is heated to 110 ℃ and stirred for 5 hours. After the reaction is completed, the solvent is removed under reduced pressure, and the mixture is extracted with dichloromethane and distilled water. The organic layer extracted is washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (6.8g, 8.3mmol).

[0377] Synthesis of intermediate 9-5

[0378] Intermediate 9-4 (6.8 g, 8.3 mmol) was dissolved in triethyl orthoformate (415 mmol), and HCl (10 mmol) was added dropwise thereto. Then, the mixture was heated to 80 ° C and stirred for 20 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the mixture was extracted with dichloromethane and distilled water. The extracted organic layer was washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent was separated using column chromatography to obtain the target compound (6.9 g, 7.9 mmol).

[0379] Synthesis of compound 9

[0380] Intermediate 9-5 (6.9 g, 7.9 mmol), potassium tetrachloroplatinate (3.6 g, 8.7 mmol) and 2,6-lutidine (3.4 g, 32 mmol) were suspended in 1,2-dichlorobenzene (150 ml). The resulting reaction mixture was heated and stirred at 120 ° C for 18 hours. After the reaction was completed, the resultant was cooled to room temperature, and the residue remaining after the solvent was removed was then separated using column chromatography to obtain the target compound (3.3 g, 3.2 mmol).

[0381] (2) Synthesis of Compound 29

[0382] The organometallic compound 29 according to the embodiment may be synthesized by, for example, the method of the following Reaction Formula 2.

[0383] Reaction 2

[0384]

[0385] Synthesis of Intermediate 29-1

[0386] 3-methoxy-11-phenyl-5,11-dihydrobenzo[4,5]thieno[3,2,b]quinoline (6.2 g, 18 mmol), 2-bromo-4(tert-butyl)pyridine (5.8 g, 27 mmol), tripotassium phosphate (8.3 g, 36 mmol), CuI (0.66 g, 3.6 mmol) and picolinic acid (0.4 g, 3.6 mmol) were placed in a reaction vessel and suspended in dimethyl sulfoxide (100 mL). The resulting reaction mixture was heated and stirred at 160 ° C for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water (100 mL) was added thereto, and the resulting mixture was then extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (6.8 g, 14.2 mmol).

[0387] Synthesis of intermediate 29-2

[0388] Intermediate 29-1 (6.8 g, 14.2 mmol) was suspended in an excess of hydrobromic acid solution. The resulting reaction mixture was heated and stirred at 110 ° C for 24 hours. After the reaction was completed, the mixture was cooled to room temperature and neutralized by adding an appropriate amount of sodium bicarbonate. Distilled water (100 mL) was added thereto, and the resulting mixture was then extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (5.2 g, 11.3 mmol).

[0389] Synthesis of intermediate 29-3

[0390] Intermediate 29-2 (5.2g, 11.3mmol), 1-bromo-3-fluorobenzene (3.0g, 17mmol) and tripotassium phosphate (5.3g, 22.6mmol) are placed in a reaction vessel and suspended in dimethyl sulfoxide (100mL). The resulting reaction mixture is heated and stirred at 160°C for 12 hours. After the reaction is complete, the mixture is cooled to room temperature, distilled water (100mL) is added thereto, and then the resulting mixture is extracted with ethyl acetate. The extracted organic layer is washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (5.7g, 9.3mmol).

[0391] Synthesis of Intermediate 29-4

[0392] Intermediate 29-3 (5.7 g, 9.3 mmol), N1-([1,1':3',1"-terphenyl]-2'-yl)benzene-1,2-diamine (3.1 g, 9.3 mmol), SPhos (0.70 mmol), Pd 2 (dba) 3 In 4% paraformaldehyde (0.46mmol) and sodium tert-butoxide (18mmol) were suspended in toluene solvent (100ml), and the mixture was then heated to 110°C and stirred for 4 hours. After the reaction was complete, the solvent was removed under reduced pressure, and the mixture was extracted with dichloromethane and distilled water. The organic layer extracted was washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent was separated using column chromatography to obtain the target compound (7.3g, 8.4mmol).

[0393] Synthesis of Intermediate 29-5

[0394] Intermediate 29-4 (7.3 g, 8.4 mmol) was dissolved in triethyl orthoformate (420 mmol), and HCl (10 mmol) was added dropwise thereto. Afterwards, the resulting reaction mixture was stirred for 20 hours at a temperature elevated to 80°C. After the reaction was complete, the solvent was removed under reduced pressure, and the mixture was extracted with dichloromethane and distilled water. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent was separated using column chromatography to obtain the target compound (7.2 g, 7.8 mmol).

[0395] Synthesis of compound 29

[0396] Intermediate 29-5 (7.2 g, 7.8 mmol), potassium tetrachloroplatinate (3.6 g, 8.6 mmol) and 2,6-lutidine (3.4 g, 32 mmol) were suspended in 1,2-dichlorobenzene (150 ml). The resulting reaction mixture was heated and stirred at 120 ° C for 18 hours. After the reaction was completed, the resultant was cooled to room temperature, and the residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (3.3 g, 3.1 mmol).

[0397] (3) Synthesis of compound 31

[0398] The organometallic compound 31 according to the embodiment may be synthesized by, for example, the method of the following Reaction Scheme 3.

[0399] Reaction 3

[0400]

[0401] Synthesis of Intermediate 31-1

[0402] Intermediate 29-3 (6.2g, 10mmol) and potassium tert-butoxide (0.23g, 2.0mmol) are placed in a reaction vessel and suspended in dimethyl sulfoxide-D6 (200mL). The resulting reaction mixture is heated and stirred at 80°C for 6 hours. After the reaction is complete, the mixture is cooled to room temperature, distilled water (200mL) is added thereto, and the resulting mixture is extracted with ethyl acetate. The extracted organic layer is washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (5.3g, 8.6mmol).

[0403] Synthesis of intermediate 31-2

[0404] Intermediate 31-1 (5.3 g, 8.6 mmol), Intermediate A-1 (3.9 g, 8.6 mmol), SPhos (0.65 mmol), Pd 2 (dba) 3 In 4% paraformaldehyde (0.43mmol) and sodium tert-butoxide (16.7mmol) were suspended in toluene solvent (100ml), and the resulting reaction mixture was heated to 110°C and stirred for 4 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the mixture obtained was extracted with dichloromethane and distilled water. The organic layer extracted was washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent was separated using column chromatography to obtain the target compound (7.7g, 7.8mmol).

[0405] Synthesis of intermediate 31-3

[0406] Intermediate 31-2 (7.7 g, 7.8 mmol) was dissolved in triethyl orthoformate (390 mmol), and HCl (9.4 mmol) was added dropwise thereto. Afterwards, the resulting reaction mixture was stirred for 20 hours at a temperature elevated to 80°C. After the reaction was complete, the solvent was removed under reduced pressure, and the resulting mixture was extracted with dichloromethane and distilled water. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent was separated using column chromatography to obtain the target compound (7.4 g, 7.1 mmol).

[0407] Synthesis of compound 31

[0408] Intermediate 31-3 (7.4 g, 7.1 mmol), potassium tetrachloroplatinate (3.3 g, 7.8 mmol) and 2,6-lutidine (3.1 g, 29 mmol) were suspended in 1,2-dichlorobenzene (130 ml). The resulting reaction mixture was heated and stirred at 120 ° C for 18 hours. After the reaction was completed, the resultant was cooled to room temperature, and the residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (3.5 g, 2.9 mmol).

[0409] (4) Synthesis of Compound 38

[0410] The organometallic compound 38 according to the embodiment may be synthesized by, for example, the method of the following Reaction Formula 4.

[0411] Reaction 4

[0412]

[0413] Synthesis of Intermediate 38-1

[0414] 3-Methoxy-11-phenyl-5,11-dihydrobenzo[4,5]thieno[3,2,b]quinoline (6.2 g, 18 mmol), 2-fluoro-4-methyl-5-phenylpyridine (3.4 g, 18 mmol) and tripotassium phosphate (8.3 g, 36 mmol) were placed in a reaction vessel and suspended in dimethyl sulfoxide (180 mL). The resulting reaction mixture was heated and stirred at 160 ° C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water (200 mL) was added thereto, and the resulting mixture was then extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (7.7 g, 15.1 mmol).

[0415] Synthesis of Intermediate 38-2

[0416] Intermediate 38-1 (7.7 g, 15.1 mmol) and potassium tert-butoxide (0.35 g, 3.0 mmol) are placed in a reaction vessel and suspended in dimethyl sulfoxide-D6 (300 mL). The resulting reaction mixture is heated and stirred at 80 ° C for 6 hours. After the reaction is complete, the mixture is cooled to room temperature, distilled water (200 mL) is added thereto, and then the resulting mixture is extracted with ethyl acetate. The extracted organic layer is washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the solvent is removed is separated using column chromatography to obtain the target compound (6.8 g, 13.2 mmol).

[0417] Synthesis of intermediate 38-3

[0418] Intermediate 38-2 (6.8 g, 13.2 mmol) is placed in a reaction vessel and suspended in dichloromethane (130 mL). The resulting reaction mixture is stirred at 0 ° C, and then boron tribromide is slowly added dropwise. The resulting reaction mixture is brought to room temperature and stirred for 2 hours, and then distilled water (200 mL) is added thereto, and the mixture is extracted with dichloromethane. The extracted organic layer is washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (4.4 g, 8.9 mmol).

[0419] Synthesis of Intermediate 38-4

[0420] Intermediate 38-3 (4.4g, 8.9mmol), 1-bromo-3-fluorobenzene (2.4g, 13mmol) and tripotassium phosphate (4.2g, 17.8mmol) are placed in a reaction vessel and suspended in dimethyl sulfoxide (90mL). The resulting reaction mixture is heated and stirred at 160°C for 12 hours. After the reaction is complete, the mixture is cooled to room temperature, distilled water (100mL) is added thereto, and then the resulting mixture is extracted with ethyl acetate. The extracted organic layer is washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (4.4g, 6.8mmol).

[0421] Synthesis of Intermediate 38-5

[0422] Intermediate 38-4 (4.4 g, 6.8 mmol), intermediate A-2 (2.9 g, 6.8 mmol), SPhos (0.51 mmol), Pd 2 (dba) 3 4-[ ...

[0423] Synthesis of Intermediate 38-6

[0424] Intermediate 38-5 (5.7 g, 6.1 mmol) was dissolved in triethyl orthoformate (305 mmol), and HCl (7.3 mmol) was added dropwise thereto. The resulting reaction mixture was heated to 80 ° C and stirred for 20 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the resulting mixture was extracted with dichloromethane and distilled water. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent was separated using column chromatography to obtain the target compound (5.5 g, 5.6 mmol).

[0425] Synthesis of compound 38

[0426] Intermediate 38-6 (5.5 g, 5.6 mmol), potassium tetrachloroplatinate (2.6 g, 6.2 mmol) and 2,6-lutidine (2.4 g, 23 mmol) were suspended in 1,2-dichlorobenzene (100 ml). The resulting reaction mixture was heated and stirred at 120 ° C for 18 hours. After the reaction was completed, the resultant was cooled to room temperature, and the residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (2.8 g, 2.4 mmol).

[0427] (5) Synthesis of Compound 43

[0428] The organometallic compound 43 according to the embodiment may be synthesized by, for example, the method of the following Reaction Formula 5.

[0429] Reaction 5

[0430]

[0431] Synthesis of Intermediate 43-1

[0432] 6-methoxy-9,9-dimethyl-4,9-dihydrothieno[3,2,b]quinoline (4.4 g, 18 mmol), 2-bromo-4(tert-butyl)pyridine (5.8 g, 27 mmol), tripotassium phosphate (8.3 g, 36 mmol), CuI (0.66 g, 3.6 mmol) and picolinic acid (0.4 g, 3.6 mmol) were placed in a reaction vessel and suspended in dimethyl sulfoxide (100 mL). The resulting reaction mixture was heated and stirred at 160 ° C for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water (100 mL) was added thereto, and the resulting mixture was then extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (5.2 g, 13.8 mmol).

[0433] Synthesis of Intermediate 43-2

[0434] Intermediate 43-1 (5.2 g, 13.8 mmol) was suspended in an excess of hydrobromic acid solution. The resulting reaction mixture was heated and stirred at 110 ° C for 24 hours. After the reaction was completed, the mixture was cooled to room temperature and neutralized by adding an appropriate amount of sodium bicarbonate. Distilled water (100 mL) was added thereto, and the resulting mixture was then extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (4.3 g, 11.8 mmol).

[0435] Synthesis of Intermediate 43-3

[0436] Intermediate 43-2 (4.3g, 11.8mmol), intermediate A-3 (4.8g, 17.7mmol), tripotassium phosphate (5.5g, 23.6mmol), CuI (0.43g, 0.14mmol) and picolinic acid (0.02g, 0.24mmol) are placed in a reaction vessel and suspended in dimethyl sulfoxide (80mL). The resulting reaction mixture is heated and stirred at 160°C for 20 hours. After the reaction is complete, the mixture is cooled to room temperature, distilled water (100mL) is added thereto, and then the resulting mixture is extracted with ethyl acetate. The extracted organic layer is washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the solvent is removed is separated using column chromatography to obtain the target compound (4.7g, 8.4mmol).

[0437] Synthesis of Intermediate 43-4

[0438] Intermediate 43-3 (4.7 g, 8.4 mmol), intermediate A-4 (7.4 g, 12.6 mmol) and Cu(OAc) were mixed. 2 In 4% paraformaldehyde (0.15g, 0.84mmol), 4-(4-(4-(4-nitropropene)-2-yl)-1-nitropropene (0.15g, 0.84mmol) was added to dimethyl sulfoxide, and the obtained reaction mixture was heated and stirred at 150°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water (100mL) was added thereto, and then the mixture obtained by ethyl acetate extraction was used. The organic layer extracted was washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent was separated using column chromatography to obtain the target compound (4.6g, 5.2mmol).

[0439] Synthesis of compound 43

[0440] Intermediate 43-4 (4.6 g, 5.2 mmol), potassium tetrachloroplatinate (2.4 g, 5.8 mmol) and 2,6-lutidine (2.2 g, 21 mmol) were suspended in 1,2-dichlorobenzene (100 ml). The resulting reaction mixture was heated and stirred at 120 ° C for 18 hours. After the reaction was completed, the resultant was cooled to room temperature, and the residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (2.2 g, 2.3 mmol).

[0441] (6) Synthesis of Compound 45

[0442] The organometallic compound 45 according to the embodiment may be synthesized by, for example, the method of the following Reaction Formula 6.

[0443] Reaction 6

[0444]

[0445] Synthesis of Intermediate 45-1

[0446] Intermediate 43-2 (4.1 g, 11.3 mmol), 1-bromo-3-fluorobenzene (3.0 g, 17 mmol) and tripotassium phosphate (5.3 g, 22.6 mmol) are placed in a reaction vessel and suspended in dimethyl sulfoxide (100 mL). The resulting reaction mixture is heated and stirred at 160 ° C for 12 hours. After the reaction is complete, the mixture is cooled to room temperature, distilled water (100 mL) is added thereto, and then the mixture obtained is extracted with ethyl acetate. The extracted organic layer is washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (4.7 g, 9.0 mmol).

[0447] Synthesis of Intermediate 45-2

[0448] Intermediate 45-1 (4.7 g, 9.0 mmol), N1-([1,1':3',1"-terphenyl]-2'-yl)benzene-1,2-diamine (3.0 g, 9.0 mmol), SPhos (0.68 mmol), Pd 2 (dba) 34-nitropropene (0.45mmol) and sodium tert-butoxide (18mmol) are suspended in toluene solvent (100ml), and the reaction mixture obtained is then heated to 110°C and stirred for 4 hours. After the reaction is complete, the solvent is removed under reduced pressure, and the mixture obtained is extracted with dichloromethane and distilled water. The organic layer extracted is washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (6.0g, 7.8mmol).

[0449] Synthesis of Intermediate 45-3

[0450] Intermediate 45-2 (6.0 g, 7.8 mmol) was dissolved in triethyl orthoformate (390 mmol), and HCl (9.4 mmol) was added dropwise thereto. Afterwards, the resulting reaction mixture was heated to 80 ° C and stirred for 20 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the resulting mixture was extracted with dichloromethane and distilled water. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (5.8 g, 7.0 mmol).

[0451] Synthesis of compound 45

[0452] Intermediate 45-3 (5.8 g, 7.0 mmol), potassium tetrachloroplatinate (3.2 g, 7.7 mmol) and 2,6-lutidine (3.0 g, 28.7 mmol) were suspended in 1,2-dichlorobenzene (140 ml). The resulting reaction mixture was heated and stirred at 120 ° C for 18 hours. After the reaction was completed, the resultant was cooled to room temperature, and the residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (2.8 g, 2.9 mmol).

[0453] (7) Synthesis of Compound 53

[0454] The organometallic compound 53 according to the embodiment may be synthesized by, for example, the method of the following Reaction Formula 7.

[0455] Reaction 7

[0456]

[0457] Synthesis of Intermediate 53-2

[0458] Intermediate 53-1 (4.7 g, 11.3 mmol), 1-bromo-3-fluorobenzene (3.0 g, 17 mmol) and tripotassium phosphate (5.3 g, 22.6 mmol) are placed in a reaction vessel and suspended in dimethyl sulfoxide (100 mL). The resulting reaction mixture is heated and stirred at 160 ° C for 12 hours. After the reaction is complete, the mixture is cooled to room temperature, distilled water (100 mL) is added thereto, and then the resulting mixture is extracted with ethyl acetate. The extracted organic layer is washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (5.2 g, 9.2 mmol).

[0459] Synthesis of Intermediate 53-3

[0460] Intermediate 53-2 (5.2 g, 9.2 mmol), N1-([1,1':3',1"-terphenyl]-2'-yl)benzene-1,2-diamine (3.1 g, 9.2 mmol), SPhos (0.69 mmol), Pd 2 (dba) 3 4-nitropropene (0.46mmol) and sodium tert-butoxide (18mmol) are suspended in toluene solvent (100ml), and the reaction mixture obtained is then heated to 110°C and stirred for 4 hours. After the reaction is complete, the solvent is removed under reduced pressure, and the mixture obtained is extracted with dichloromethane and distilled water. The organic layer extracted is washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (6.5g, 7.9mmol).

[0461] Synthesis of Intermediate 53-4

[0462] Intermediate 53-3 (6.5 g, 7.9 mmol) was dissolved in triethyl orthoformate (395 mmol), and HCl (9.4 mmol) was added dropwise thereto. The resulting reaction mixture was stirred for 20 hours at a temperature elevated to 80°C. After the reaction was complete, the solvent was removed under reduced pressure, and the resulting mixture was extracted with dichloromethane and distilled water. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent was separated using column chromatography to obtain the target compound (5.9 g, 6.8 mmol).

[0463] Synthesis of compound 53

[0464] Intermediate 53-4 (5.9 g, 6.8 mmol), potassium tetrachloroplatinate (3.1 g, 7.5 mmol) and 2,6-lutidine (2.9 g, 27.9 mmol) were suspended in 1,2-dichlorobenzene (140 ml). The resulting reaction mixture was heated and stirred at 120 ° C for 18 hours. After the reaction was completed, the resultant was cooled to room temperature, and the residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (2.9 g, 2.8 mmol).

[0465] (8) Synthesis of Compound 60

[0466] The organometallic compound 60 according to the embodiment may be synthesized by, for example, the method of the following Reaction Formula 8.

[0467] Reaction 8

[0468]

[0469] Synthesis of Intermediate 60-1

[0470] Intermediate 53-1 (4.7 g, 11.3 mmol), 1-bromo-3-fluorobenzene-2,4,5,6-D4 (3.0 g, 17 mmol) and tripotassium phosphate (5.3 g, 22.6 mmol) were placed in a reaction vessel and suspended in dimethyl sulfoxide (100 mL). The resulting reaction mixture was heated and stirred at 160 ° C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water (100 mL) was added thereto, and then the resulting mixture was extracted with ethyl acetate. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (5.2 g, 9.0 mmol).

[0471] Synthesis of Intermediate 60-2

[0472] Intermediate 60-1 (5.2 g, 9.0 mmol), intermediate A-5 (4.6 g, 9.0 mmol), SPhos (0.68 mmol), Pd 2 (dba) 3 In 4% paraformaldehyde (0.05g, 0.2mmol), 4-dichloro-2-nitropropene (0.45mmol) and sodium tert-butoxide (18mmol) were suspended in toluene solvent (100ml), and the reaction mixture obtained was heated to 110°C and stirred for 4 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the mixture obtained was extracted with dichloromethane and distilled water. The organic layer extracted was washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent was separated using column chromatography to obtain the target compound (8.0g, 8.0mmol).

[0473] Synthesis of Intermediate 60-3

[0474] Intermediate 60-2 (8.0 g, 8.0 mmol) was dissolved in triethyl orthoformate (400 mmol), and HCl (9.5 mmol) was added dropwise thereto. Afterwards, the resulting reaction mixture was heated to 80 ° C and stirred for 20 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the resulting mixture was extracted with dichloromethane and distilled water. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent was separated using column chromatography to obtain the target compound (7.6 g, 7.2 mmol).

[0475] Synthesis of compound 60

[0476] Intermediate 60-3 (7.6 g, 7.2 mmol), potassium tetrachloroplatinate (3.3 g, 7.9 mmol) and 2,6-lutidine (3.1 g, 29.5 mmol) were suspended in 1,2-dichlorobenzene (140 ml). The resulting reaction mixture was heated and stirred at 120 ° C for 18 hours. After the reaction was completed, the resultant was cooled to room temperature, and the residue remaining after the solvent was removed was then separated using column chromatography to obtain the target compound (3.7 g, 3.1 mmol).

[0477] (9) Synthesis of Compound 73

[0478] The organometallic compound 73 according to the embodiment may be synthesized by, for example, the method of the following Reaction Formula 9.

[0479] Reaction 9

[0480]

[0481] Synthesis of Intermediate 73-2

[0482] Intermediate 73-1 (5.0 g, 11.3 mmol), 1-bromo-3-fluorobenzene (3.0 g, 17 mmol) and tripotassium phosphate (5.3 g, 22.6 mmol) are placed in a reaction vessel and suspended in dimethyl sulfoxide (100 mL). The resulting reaction mixture is heated and stirred at 160 ° C for 12 hours. After the reaction is complete, the mixture is cooled to room temperature, distilled water (100 mL) is added thereto, and then the resulting mixture is extracted with ethyl acetate. The extracted organic layer is washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (5.1 g, 8.5 mmol).

[0483] Synthesis of Intermediate 73-3

[0484] Intermediate 73-2 (5.1 g, 8.5 mmol), intermediate A-6 (2.9 g, 8.5 mmol), SPhos (0.64 mmol), Pd 2 (dba) 3 4-nitropropene (0.42mmol) and sodium tert-butoxide (17mmol) are suspended in toluene solvent (100ml), and the reaction mixture obtained is then heated to 110°C and stirred for 4 hours. After the reaction is complete, the solvent is removed under reduced pressure, and the mixture obtained is extracted with dichloromethane and distilled water. The organic layer extracted is washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (6.6g, 7.6mmol).

[0485] Synthesis of Intermediate 73-4

[0486] Intermediate 73-3 (6.6 g, 7.6 mmol) was dissolved in triethyl orthoformate (380 mmol), and HCl (9.0 mmol) was added dropwise thereto. Afterwards, the resulting reaction mixture was heated to 80 ° C and stirred for 20 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the resulting mixture was extracted with dichloromethane and distilled water. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (6.4 g, 7.0 mmol).

[0487] Synthesis of compound 73

[0488] Intermediate 73-4 (6.4 g, 7.0 mmol), potassium tetrachloroplatinate (3.2 g, 7.7 mmol) and 2,6-lutidine (3.0 g, 28.7 mmol) were suspended in 1,2-dichlorobenzene (140 ml). Afterwards, the resulting reaction mixture was heated and stirred at 120 ° C for 18 hours. After the reaction was completed, the resultant was cooled to room temperature, and then the residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (3.2 g, 3.0 mmol).

[0489] (10) Synthesis of Compound 81

[0490] The organometallic compound 81 according to the embodiment may be synthesized by, for example, the method of the following Reaction Scheme 10.

[0491] Reaction 10

[0492]

[0493] Synthesis of Intermediate 81-2

[0494] Intermediate 81-1 (4.5g, 11.3mmol), 1-bromo-3-fluorobenzene (3.0g, 17mmol) and tripotassium phosphate (5.3g, 22.6mmol) are placed in a reaction vessel and suspended in dimethyl sulfoxide (100mL). The resulting reaction mixture is heated and stirred at 160°C for 12 hours. After the reaction is complete, the mixture is cooled to room temperature, distilled water (100mL) is added thereto, and then the resulting mixture is extracted with ethyl acetate. The extracted organic layer is washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent is separated using column chromatography to obtain the target compound (4.5g, 8.2mmol).

[0495] Synthesis of Intermediate 81-3

[0496] Intermediate 81-2 (4.5 g, 8.2 mmol), intermediate A-6 (2.8 g, 8.2 mmol), SPhos (0.62 mmol), Pd 2 (dba) 3 4-nitropropene (5.8g, 7.1mmol) was added into 4-nitropropene (0.41mmol) and sodium tert-butoxide (16.4mmol) and were suspended in toluene solvent (100ml), and the reaction mixture obtained was then heated to 110°C and stirred for 4 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the mixture obtained was extracted with dichloromethane and distilled water. The organic layer extracted was washed with saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent was separated using column chromatography to obtain the target compound (5.8g, 7.1mmol).

[0497] Synthesis of Intermediate 81-4

[0498] Intermediate 81-3 (5.8 g, 7.1 mmol) was dissolved in triethyl orthoformate (350 mmol), and HCl (8.4 mmol) was added dropwise thereto. Thereafter, the resulting reaction mixture was stirred for 20 hours at a temperature elevated to 80°C. After the reaction was complete, the solvent was removed under reduced pressure, and the resulting mixture was extracted with dichloromethane and distilled water. The extracted organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue remaining after the removal of the solvent was separated using column chromatography to obtain the target compound (5.6 g, 6.5 mmol).

[0499] Synthesis of compound 81

[0500] Intermediate 81-4 (5.6 g, 6.5 mmol), potassium tetrachloroplatinate (3.0 g, 7.2 mmol) and 2,6-lutidine (2.8 g, 26.4 mmol) were suspended in 1,2-dichlorobenzene (130 ml). The resulting reaction mixture was heated and stirred at 120 ° C for 18 hours. After the reaction was completed, the resultant was cooled to room temperature, and the residue remaining after the solvent was removed was separated using column chromatography to obtain the target compound (2.7 g, 2.6 mmol).

[0501] 2. Determination of organometallic compounds

[0502] The compound synthesized as an example of the synthesis of the above-mentioned organometallic compound 1 H-NMR and MS / FAB analysis results are shown in the following Table 1. Methods for synthesizing compounds other than those synthesized in the synthesis examples described with reference to Reaction Formulas 1 to 10 can be easily modified and applied by referring to the above-mentioned synthesis routes and starting materials.

[0503] Table 1

[0504]

[0505]

[0506] 3. Evaluation of organometallic compounds

[0507] Table 2 below shows the organometallic compounds used in Examples and Comparative Examples.

[0508] Table 2

[0509]

[0510]

[0511]

[0512] The following Table 3 shows the results of evaluating the material properties of the organometallic compounds used in the Examples and Comparative Examples. The HOMO level (eV), LUMO level (eV), maximum emission wavelength (λ) of the above-mentioned Compound 9, Compound 29, Compound 31, Compound 38, Compound 43, Compound 45, Compound 53, Compound 60, Compound 73 and Compound 81 and Comparative Compound C1, Comparative Compound C2, Comparative Compound C3 and Comparative Compound C4 were evaluated using a density functional theory (DFT) method of the Gaussian09 program with structural optimization at the B3LYP / 6-311g(d,p) / LANL2DZ level (e.g., using a B3LYP mixed functional and a 6-311g(d,p) and LANL2DZ mixed basis set).max exp ) and triplet metal-to-ligand charge transfer states ( 3 The presence rate (%) of MLCT).

[0513] Table 3

[0514]

[0515]

[0516] Referring to the results in Table 3, the Example compounds showed a smaller HOMO energy level value than the Comparative Example compounds. In addition, the Example compounds showed a relatively shorter maximum emission wavelength than the Comparative Example compounds. That is, it was determined that the Example compounds emitted deep blue light, which is blue light in the short wavelength range, compared with the Comparative Example compounds. In addition, based on the fact that the Example compounds had higher 3 Based on the MLCT ratio, it is considered that the Example compounds can show relatively higher luminescence efficiency than the compounds of Comparative Examples 1 and 2.

[0517] Meanwhile, the compounds of Comparative Examples 3 and 4 have similar high 3 MLCT ratio, but the Example compound has a smaller HOMO level (deep level) than Comparative Examples 3 and 4, and thus can have low driving voltage characteristics.

[0518] 4. Preparation and evaluation of light-emitting elements

[0519] (1) Preparation of light-emitting elements

[0520] A light-emitting element comprising an organic metal compound according to the embodiment or a comparative example compound was prepared by the following method. The organic metal compounds of the examples were each used as a dopant material for the emission layer to manufacture the light-emitting elements of Examples 1 to 10. Comparative Example Compound C3 and Comparative Example Compound C4 were used as dopant materials for the emission layer to prepare the light-emitting elements of Comparative Examples 3 and 4.

[0521] As the first electrode, an ITO electrode (Corning, 15Ω / cm 2 , ) was cut into a size of about 50 mm×50 mm×0.7 mm, ultrasonically cleaned for 5 minutes and irradiated with ultraviolet rays for 30 minutes using isopropyl alcohol and pure water respectively, and then exposed to ozone for cleaning to be mounted on a vacuum deposition apparatus.

[0522] The first electrode is vacuum deposited with 2-TNATA to form a The hole injection layer is formed by vacuum deposition of N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (hereinafter referred to as "NPB") to form a hole injection layer having a thickness of The hole transport layer has a thickness of .

[0523] The hole transport layer is vacuum deposited with the example compound or the comparative example compound (first compound), the compound ETH2 (second compound) and the compound HT33 (third compound) to form a In this case, the amount of the example compound or the comparative example compound relative to the total weight (100 wt %) of the emission layer is 10 wt %, and the compound ETH2 and the compound HT33 are adjusted to have a weight ratio of 3:7.

[0524] The emission layer is vacuum deposited with compound ETH2 to form Then, the hole blocking layer was vacuum deposited with CNNPTRZ and Liq (8-hydroxy-quinoline lithium) in a weight ratio of 1:1 to form a hole blocking layer having a thickness of Then, Yb was vacuum deposited on the top of the electron transport layer to form an electron transport layer having a thickness of The electron injection layer is formed by vacuum deposition of Mg to form an electron injection layer having a thickness of A second electrode with a thickness of , thereby preparing a light-emitting element.

[0525]

[0526] (2) Evaluation of light-emitting elements

[0527] The evaluation results of the light-emitting elements of the examples and comparative examples are shown in Table 4 below. 2 The driving voltage (V) at the brightness of , CIE color coordinates, luminous efficiency, color conversion efficiency based on the CIE color coordinate y, and the maximum emission wavelength indicating the maximum value at the emission peak. The color conversion efficiency values ​​in Table 4 correspond to the luminous efficiency shown in Table 4 divided by the CIE color coordinate y.

[0528] Table 4

[0529]

[0530]

[0531] Referring to the results in Table 4, it can be seen that the light-emitting element of the embodiment shows a lower driving voltage than the comparative example. In addition, the light-emitting element of the embodiment shows different CIE color coordinates (x, y) compared with the light-emitting element of the comparative example (comprising a comparative example compound having a heteropolycyclic ring different from the embodiment compound). That is, it is determined that the embodiment shows a luminescent property shifted to the blue region compared with the comparative example. In addition, it can be seen that based on the blue-shifted color coordinate value y, the embodiment shows a higher color conversion efficiency than the comparative example.

[0532] In addition, it can be seen that the embodiment shows a shorter wavelength emission characteristic than the comparative example. In particular, it is determined that the comparative example 4 using the comparative example compound C4 without a bulky substituent (e.g., an aromatic ring) emits light of a longer wavelength than the embodiment. This indicates that in the absence of a bulky substituent (e.g., an aromatic ring), the formation of an exciplex with the host is promoted, and therefore, due to the change in the emission spectrum, the emission wavelength from the light-emitting element is shifted to a longer wavelength.

[0533] In the light-emitting element of the embodiment, the emission layer may include the organic metal compound of the embodiment. The organic metal compound of the embodiment includes a group or a specific heteropolycyclic ring in the ligand bonded to the central metal atom, and thus may exhibit deep blue light emission properties.

[0534] The organometallic compound of the embodiment includes a group or a specific heteropolycyclic ring as a ligand, and thus has an increased 3 MLCT properties and low HOMO energy level, and therefore, can exhibit excellent light efficiency, low driving voltage, and also maintain deep blue light emitting properties.

[0535] Furthermore, the organometallic compound of the embodiment can be used as a phosphorescent material, and a light-emitting element including the organometallic compound of the embodiment can exhibit high efficiency and low driving voltage.

[0536] The light-emitting element of the embodiment includes the organic metal compound of the embodiment, and thus can exhibit low driving voltage and high efficiency.

[0537] The organometallic compound of the embodiment may contribute to achieving deep blue color and increasing the light efficiency of the light emitting element.

[0538] The display device of the embodiment can exhibit high display quality.

[0539] Although the subject matter of the present disclosure has been described with reference to exemplary embodiments thereof, it should be understood that the disclosure should not be limited to these exemplary embodiments but various changes and modifications may be made by those skilled in the art without departing from the spirit and scope of the disclosure.

[0540] Therefore, the technical scope of the present disclosure is not intended to be limited to the contents set forth in the detailed description of the specification, but is intended to be defined by the appended claims and their equivalents.

Claims

1. An organometallic compound represented by formula 1: Formula 1 In formula 1, At least one of W1 to W3 is O or S and the rest are CRa, Ra is a hydrogen atom, a deuterium atom, a halogen atom, 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 oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 ring-forming carbon atoms, or bonds to an adjacent group to form a ring, and R1, R2 and R 11 To R 26 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, 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 oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 ring-forming carbon atoms.

2. The organometallic compound according to claim 1, wherein Formula 1 is represented by Formula 1-1: Formula 1-1 In formula 1-1, W 11 is O or S, R a1 and R a2 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, 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 oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 ring carbon atoms, and R1, R2 and R 11 To R 26 The same as defined with respect to Formula 1.

3. The organometallic compound according to claim 2, wherein R a1 and R a2 It's a hydrogen atom.

4. The organometallic compound according to claim 1, wherein Formula 1 is represented by Formula 1-2: Formula 1-2 In formula 1-2, W 11 is O or S, Cy is a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring having 3 to 30 ring carbon atoms, and R1, R2 and R 11 To R 26 The same as defined with respect to Formula 1. The organometallic compound according to claim 4 , wherein Cy is a substituted or unsubstituted benzene ring. The organometallic compound of claim 1 , wherein the organometallic compound represented by Formula 1 emits phosphorescence.

7. The organometallic compound according to claim 1, wherein Formula 1 is represented by any one of the compounds of Compound Group 1: Compound Group 1 Wherein in compound group 1, D is a deuterium atom, and Ph is an unsubstituted phenyl group.

8. Light-emitting element, including: a first electrode; a second electrode on the first electrode; as well as an emission layer between the first electrode and the second electrode and including a first compound, The first compound is an organometallic compound according to any one of claims 1 to 7.

9. The light-emitting element according to claim 8, further comprising at least one of a second compound represented by Formula HT-1 and a third compound represented by Formula ET-1: Formula HT-1 Wherein in formula HT-1, A1 to A8 are each independently N or CR 51 , L1 is a direct bond, 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, Y a It is a direct key, CR 52 R 53 or SiR 54 R 55 , Ar1 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, and R 51 To R 55 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-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, or is bonded to an adjacent group to form a ring, Formula ET-1 Wherein in formula ET-1, At least one of X1 to X3 is N and the rest are CR 56 , R 56 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 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, b1 to b3 are each independently an integer from 0 to 10, Ar2 to Ar4 are each independently 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, and L2 to L4 are each independently a direct bond, 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.

10. The light-emitting element according to claim 9, wherein the emission layer further comprises a fourth compound represented by Formula F-1: Formula F-1 Wherein in formula F-1, A1 and A2 are each independently O, S, Se or NR m , 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, and R 1a To R 11a Each is independently 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 is bonded to an adjacent group to form a ring. 11 . The light-emitting element according to claim 10 , wherein the emission layer comprises the first compound, the second compound, the third compound, and the fourth compound. 12 . The light-emitting element according to claim 8 , wherein the emission layer comprises a host and a phosphorescent dopant, and the phosphorescent dopant is the first compound. 13 . The light-emitting element according to claim 8 , wherein the emission layer emits blue light having a maximum central wavelength of 470 nm or less.

14. A display device comprising: Base layer; a circuit layer on the substrate layer; as well as a display element layer on the circuit layer and including light-emitting elements, The light-emitting element includes a first electrode, a second electrode facing the first electrode, and an emission layer between the first electrode and the second electrode and containing the organic metal compound according to any one of claims 1 to 7. The display device according to claim 14 , wherein the light emitting element emits blue light.

16. The display device of claim 15, further comprising a light control layer comprising quantum dots.

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