Light emitting element and organometallic compound for light emitting element

Abstract

A light-emitting element of one embodiment may include a first electrode, a second electrode, and a light-emitting layer disposed between the first electrode and the second electrode and comprising an organometallic compound represented by the following chemical formula 1, and may exhibit high light-emitting efficiency, high color purity characteristics, and long lifespan characteristics. [Chemical Formula 1]

Description

Technology Field

[0001] The present invention relates to a light-emitting element and an organometallic compound for a light-emitting element, and specifically to a light-emitting element comprising an organometallic compound in a light-emitting layer and an organometallic compound used therein. Background Technology

[0002] Recently, there has been active development of organic electroluminescence displays as image display devices. Unlike liquid crystal displays, organic electroluminescence displays are so-called self-emissive display devices that realize a display by causing a light-emitting material containing an organic compound in the light-emitting layer to emit light by recombining holes and electrons injected from a first electrode and a second electrode in the light-emitting layer.

[0003] In applying light-emitting devices to display devices, there is a demand for lower driving voltage, higher luminous efficiency, and longer lifespan of the light-emitting devices, and there is a continuous need for the development of materials for light-emitting devices that can stably realize these requirements. The problem to be solved

[0004] The object of the present invention is to provide a light-emitting device having high luminous efficiency, high color purity, and long lifespan characteristics, and an organometallic compound used therein. means of solving the problem

[0005] One embodiment comprises a second electrode disposed on the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode, comprising at least one of a first compound represented by the following chemical formula 1 and a second to fourth compound, wherein the first to fourth compounds provide different light-emitting elements.

[0006] [Chemical Formula 1]

[0008]

[0010] In the above chemical formula 1, M is Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, or Os, and A1 to A3, and A 41 To A 44 are each independently a ring-forming hydrocarbon ring with 5 to 60 carbon atoms, or a heterocycle with 1 to 60 carbon atoms; b1 to b3 are each independently integers from 0 to 4; b41 to b44 are each independently integers from 0 to 3; and L1 to L4 are each independently direct linkage, *-O-*', *-S-*', *-C(R 11 )(R 12 )-*', *-C(R 13 )=*', *-C(R 14 )=C(R 15 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 16 )-*', *-N(R 17 )-*', *-P(R 18 )(R 19 )-*', *-Si(R 20 )(R 21 )-*', and *-Ge(R 22 )(R 23 Selected from )-*', n1 and n3 are each independently integers from 0 to 3, n2 and n4 are each independently integers from 1 to 3, and R1 to R3, and R 41 to R 44 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group with 3 to 30 carbon atoms, and R 11 to R 23Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[0011] The above chemical formula 1 may be represented by the following chemical formula 2.

[0012] [Chemical Formula 2]

[0013] In the above Chemical Formula 2, X1 and X2 are each independently CRa or N, and Ra is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, and A1 to A3, n1, n3, n4, L1, L 3, L4, b1 to b3, b41 to b44, R1 to R3, and R 41 to R 44 It is the same as defined in Chemical Formula 1 above.

[0014] The above chemical formula 2 may be represented by the following chemical formula 3-1 or chemical formula 3-2.

[0015] [Chemical Formula 3-1]

[0016]

[0017] [Chemical Formula 3-2]

[0018]

[0019] In the above chemical formula 3-1 and the above chemical formula 3-2, A1 to A3, n1, n3, n4, L1, L3, L4, b1 to b3, b41 to b44, R1 to R3, and R 41 to R 44 It is the same as defined in Chemical Formula 1 above.

[0020] The above chemical formula 3-1 may be represented by the following chemical formula 3A or chemical formula 3B.

[0021] [Chemical Formula 3A]

[0022]

[0023] [Chemical Formula 3B]

[0024]

[0025] In the above chemical formulas 3A and 3B, A1 to A3, n1, n3, L1, L3, b1 to b3, b41 to b44, R1 to R3, R 41 to R 44 , and R 17 It is the same as defined in Chemical Formula 1.

[0026] R in the above chemical formula 3B 17 It may be a substituted or unsubstituted phenyl group.

[0027] R in the above chemical formula 3-2 43 and R 44 Each can be a hydrogen atom.

[0028] The above chemical formula 2 may be represented by the following chemical formula 4.

[0029] [Chemical Formula 4]

[0030]

[0031] In the above chemical formula 4, n4, L4, b2, b3, b41 to b44, R1 to R3, R 41 to R 44 , X1, and X2 are the same as defined in Chemical Formula 2.

[0032] R1 to R3, and R 41 to R 44 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted phenyl group.

[0033] The light-emitting layer comprises the second compound and the third compound, wherein the first compound may be a phosphorescent dopant, the second compound may be a hole-transporting host, and the third compound may be an electron-transporting host.

[0034] The light-emitting layer comprises the fourth compound, and the fourth compound may be a delayed fluorescence dopant.

[0035] The above-mentioned light-emitting layer may emit blue light.

[0036] Another embodiment provides an organometallic compound represented by the following chemical formula 1.

[0037] [Chemical Formula 1]

[0038]

[0039] In the above chemical formula 1, M is Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, or Os, and A1 to A3, and A 41 To A 44 are each independently a ring-forming hydrocarbon ring with 5 to 60 carbon atoms, or a heterocycle with 1 to 60 carbon atoms, b1 to b3 are each independently integers from 0 to 4, b41 to b44 are each independently integers from 0 to 3, and L1 to L4 are each independently direct bonds, *-O-*', *-S-*', *-C(R 11 )(R 12 )-*', *-C(R 13 )=*', *-C(R 14 )=C(R 15 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 16 )-*', *-N(R 17 )-*', *-P(R 18 )(R 19 )-*', *-Si(R 20 )(R 21 )-*', and *-Ge(R 22 )(R 23Selected from )-*', n1 and n3 are each independently integers from 0 to 3, n2 and n4 are each independently integers from 1 to 3, and R1 to R3, and R 41 to R 44 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group with 3 to 30 carbon atoms, and R 11 to R 23 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[0040] The above chemical formula 1 may be represented by the following chemical formula 2.

[0041] [Chemical Formula 2]

[0042]

[0043] In the above Chemical Formula 2, X1 and X2 are each independently CRa or N, and Ra is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, and A1 to A3, n1, n3, n4, L1, L 3, L4, b1 to b3, b41 to b44, R1 to R3, and R 41 to R 44 It is the same as defined in Chemical Formula 1 above.

[0044] The above chemical formula 2 may be represented by the following chemical formula 3-1 or chemical formula 3-2.

[0045] [Chemical Formula 3-1]

[0046]

[0047] [Chemical Formula 3-2]

[0048]

[0049] In the above chemical formula 3-1 and the above chemical formula 3-2, A1 to A3, n1, n3, n4, L1, L3, L4, b1 to b3, b41 to b44, R1 to R3, and R 41 to R 44 It is the same as defined in Chemical Formula 1.

[0050] The above chemical formula 3-1 may be represented by the following chemical formula 3A or chemical formula 3B.

[0051] [Chemical Formula 3A]

[0052]

[0053] [Chemical Formula 3B]

[0054]

[0055] In the above chemical formulas 3A and 3B, A1 to A3, n1, n3, L1, L3, b1 to b3, b41 to b44, R1 to R3, R 41 to R 44 , and R 17 It is the same as defined in Chemical Formula 1.

[0056] R in the above chemical formula 3B 17 It may be a substituted or unsubstituted phenyl group.

[0057] R in the above chemical formula 3-2 43 and R 44 Each can be a hydrogen atom.

[0058] The above chemical formula 2 may be represented by the following chemical formula 4.

[0059] [Chemical Formula 4]

[0060]

[0061] In the above chemical formula 4, n4, L4, b2, b3, b41 to b44, R2, R3, R 41 to R 44 , X1, and X2 are the same as defined in Chemical Formula 2. Effects of the invention

[0062] The light-emitting element of one embodiment is high 3 MLCT values ​​and high 3 Organometallic compounds having an MC value can exhibit high efficiency, high color purity, and long lifespan characteristics.

[0063] The organometallic compound of one embodiment includes spirobiacridine, high 3 MLCT value and high 3 You can have an MC. Brief explanation of the drawing

[0064] FIG. 1 is a plan view showing a display device according to one embodiment. FIG. 2 is a cross-sectional view of a display device according to one embodiment. FIG. 3 is a cross-sectional view schematically showing a light-emitting element according to one embodiment. FIG. 4 is a cross-sectional view schematically showing a light-emitting element according to one embodiment. FIG. 5 is a cross-sectional view schematically showing a light-emitting element according to one embodiment. FIG. 6 is a cross-sectional view schematically showing a light-emitting element according to one embodiment. FIG. 7 is a cross-sectional view of a display device according to one embodiment. FIG. 8 is a cross-sectional view of a display device according to one embodiment. FIG. 9 is a cross-sectional view of a display device according to one embodiment. FIG. 10 is a cross-sectional view of a display device according to one embodiment. Specific details for implementing the invention

[0065] The present invention is capable of various modifications and may take various forms, and specific embodiments are illustrated in the drawings and described in detail in the text. However, this is not intended to limit the invention to the specific disclosed forms, and it should be understood that the invention includes all modifications, equivalents, and substitutions that fall within the spirit and scope of the invention.

[0066] In describing each drawing, similar reference numerals have been used for similar components. In the attached drawings, the dimensions of the structures are depicted enlarged from their actual size for clarity of the invention. Terms such as "first," "second," etc., may be used to describe various components, but said components should not be limited by said terms. These terms are used solely for the purpose of distinguishing one component from another. For example, without departing from the scope of the invention, the first component may be named the second component, and similarly, the second component may be named the first component. A singular expression includes a plural expression unless the context clearly indicates otherwise.

[0067] In this application, terms such as "comprising" or "having" are intended to specify the existence of the features, numbers, steps, actions, components, parts, or combinations thereof described in the specification, and should be understood as not precluding the existence or addition of one or more other features, numbers, steps, actions, components, parts, or combinations thereof.

[0068] In this application, when a part such as a layer, film, region, or plate is described as being "on" or "upper" to another part, this includes not only cases where it is "immediately above" the other part, but also cases where there is another part in between. Conversely, when a part such as a layer, film, region, or plate is described as being "under" or "lower" to another part, this includes not only cases where it is "immediately below" the other part, but also cases where there is another part in between. Furthermore, in this application, being "placed on" may include cases where it is placed not only on the upper part but also on the lower part.

[0069] In this specification, "substituted or unsubstituted" may mean substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, nitro groups, amino groups, silyl groups, oxy groups, thio 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. Additionally, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or as a phenyl group substituted with a phenyl group.

[0070] In this specification, "forming a ring by combining with adjacent groups" may mean forming a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted hetero ring by combining with adjacent groups. The hydrocarbon ring includes an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring. The hetero ring includes an aliphatic hetero ring and an aromatic hetero ring. The hydrocarbon ring and the hetero ring may be monocyclic or polycyclic. Additionally, the ring formed by combining with each other may be connected to another ring to form a spiro structure.

[0071] In this specification, "adjacent group" may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, another substituent substituted on the atom on which the substituent is substituted, or a substituent that is stereostructively closest to the substituent. For example, in 1,2-dimethylbenzene, two methyl groups may be interpreted as "adjacent groups," and in 1,1-diethylcyclopentane, two ethyl groups may be interpreted as "adjacent groups." Additionally, in 4,5-dimethylphenanthrene, two methyl groups may be interpreted as "adjacent groups."

[0072] In this specification, examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0073] In this specification, the alkyl group may be of the straight chain or branched chain type. The number of carbon atoms in the alkyl group is 1 or more and 50 or less, 1 or more and 30 or less, 1 or more and 20 or less, 1 or more and 10 or less, or 1 or more and 6 or less. Examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group, n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, n-heptyl group, 1-methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group. 3,7-dimethyloctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-icosyl group, 2-ethylicosyl group, 2-butylicosyl group, Examples include, but are not limited to, 2-hexylicosyl groups, 2-octylicosyl groups, n-henicosyl groups, n-docosyl groups, n-tricosyl groups, n-tetracosyl groups, n-pentacosyl groups, n-hexacosyl groups, n-heptacosyl groups, n-octacosyl groups, n-nonacosyl groups, and n-triacontyl groups.

[0074] In this specification, a cycloalkyl group may refer to a cyclic alkyl group. The number of carbon atoms in a cycloalkyl group is 3 or more and 50 or less, 3 or more and 30 or less, or 3 or more and 20 or less, or 3 or more and 10. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, norbornyl group, 1-adamantyl group, 2-adamantyl group, isobornyl group, bicycloheptyl group, etc.

[0075] In this specification, an alkenyl group refers to a hydrocarbon group comprising one or more carbon double bonds at the middle or terminal of an alkyl group having two or more carbon atoms. The alkenyl group may be straight or branched. The number of carbon atoms is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienyl aryl groups, styrenyl groups, styrylvinyl groups, etc.

[0076] In this specification, an alkynyl group refers to a hydrocarbon group comprising one or more carbon triple bonds at the middle or terminal of an alkyl group having two or more carbon atoms. The alkynyl group may be straight or branched. The number of carbon atoms is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Specific examples of alkynyl groups may include, but are not limited to, ethinyl groups, propynyl groups, etc.

[0077] In this specification, a hydrocarbon ring group refers to any 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 carbon atoms forming the ring.

[0078] In this specification, an aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring-forming carbon atoms in the aryl group may be 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 15 or less. Examples of aryl groups may include, but are not limited to, phenyl groups, naphthyl groups, fluorenyl groups, anthracenyl groups, phenanthryl groups, biphenyl groups, terphenyl groups, quarterphenyl groups, quinquephenyl groups, sexphenyl groups, triphenylenyl groups, pyrenyl groups, benzofluranthenyl groups, crisenyl groups, etc.

[0079] In this specification, the fluorenyl group may be substituted, and two substituents may be combined to form a spiro structure. Examples of cases where the fluorenyl group is substituted are as follows. However, it is not limited thereto.

[0080]

[0081] In this specification, a heterocyclic group refers to any functional group or substituent derived from a ring comprising one or more of B, O, N, P, Si, and S as heteroatoms. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl groups. Aliphatic heterocyclic groups and aromatic heterocyclic groups may be monocyclic or polycyclic.

[0082] In this specification, a heterocyclic group may include one or more of B, O, N, P, Si, and S as heteroatoms. If the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be identical or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and is a concept that includes a heteroaryl group. The number of ring-forming carbons of the heterocyclic group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less.

[0083] In this specification, the aliphatic heterocyclic group may include one or more of B, O, N, P, Si, and S as heteroatoms. The number of ring-forming carbon atoms in the aliphatic heterocyclic group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of the aliphatic heterocyclic group include, but are not limited to, oxirane groups, thiran groups, pyrrolidine groups, piperidine groups, tetrahydrofuran groups, tetrahydrothiophene groups, thian groups, tetrahydropyran groups, 1,4-dioxane groups, etc.

[0084] In this specification, the heteroaryl group may include one or more of B, O, N, P, Si, and S as heteroatoms. If the heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be identical or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring-forming carbons in the heteroaryl group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acryl group, pyridazine group, pyrazinyl group, quinoline group, quinazolin group, quinoxaline group, phenoxazine group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, N-arylcarbazole group, N-heteroarylcarbazole group, N-alkylcarbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophen group, dibenzothiophen group, thienothiophene group, benzofuran group, phenanthroline group. Thiazol groups, isooxazole groups, oxazole groups, oxadiazole groups, thiadiaazole groups, phenothiazine groups, dibenzosilol groups and dibenzofuran groups, etc., are included but are not limited to these.

[0085] In this specification, the description of the aryl group described above may apply except that the arylene group is a divalent group. The description of the heteroaryl group described above may apply except that the heteroarylene group is a divalent group.

[0086] In this specification, silyl groups include alkyl silyl groups and aryl silyl groups. Examples of silyl groups include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, t-butyldimethylsilyl groups, vinyldimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, phenylsilyl groups, etc.

[0087] In this specification, the number of carbon atoms in the amino group is not particularly limited, but may be 1 or more and 30 or less. The amino group may include an alkyl amino group, an aryl amino group, or a heteroaryl amino group. Examples of amino groups include, but are not limited to, methylamino groups, dimethylamino groups, phenylamino groups, diphenylamino groups, naphthylamino groups, 9-methyl-anthracenylamino groups, triphenylamino groups, etc.

[0088] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40 or fewer, 1 to 30 or fewer, or 1 to 20 or fewer. For example, it may have the following structure, but is not limited thereto.

[0089]

[0090] In this specification, the number of carbon atoms in the sulfinyl group and the sulfonyl group is not particularly limited, but may be 1 or more and 30 or less. The sulfinyl group may include an alkyl sulfinyl group and an aryl sulfinyl group. The sulfonyl group may include an alkyl sulfonyl group and an aryl sulfonyl group.

[0091] In this specification, the thio group may include alkyl thio groups and aryl thio groups. The thio group may mean that a sulfur atom is bonded to the alkyl or aryl group defined above. Examples of thio groups include, but are not limited to, methyl thio group, ethyl thio group, propyl thio group, pentyl thio group, hexyl thio group, octyl thio group, dodecyl thio group, cyclopentyl thio group, cyclohexyl thio group, phenyl thio group, naphthyl thio group, etc.

[0092] In this specification, an oxy group may refer to an alkyl group or aryl group defined above in which an oxygen atom is bonded. An oxy group may include an alkoxy group and an aryl oxy group. An alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in an alkoxy group is not particularly limited, but may be, for example, 1 or more and 20 or less, or 1 or more and 10 or less. Examples of oxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc.

[0093] In this specification, a boron group may mean that a boron atom is bonded to the alkyl group or aryl group defined above. Boron groups include alkyl boron groups and aryl boron groups. Examples of boron groups include, but are not limited to, dimethyl boron groups, diethyl boron groups, t-butylmethyl boron groups, diphenyl boron groups, phenyl boron groups, etc.

[0094] In this specification, the alkenyl group may be a straight chain or a branched chain. The number of carbon atoms is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, butenyl, 1-pentenyl, 1,3-butadienyl aryl, styrenyl, styrylvinyl, etc., but are not limited to these.

[0095] In this specification, the number of carbon atoms in the amine group is not particularly limited, but may be 1 or more and 30 or less. The amine group may include alkyl amine groups and aryl amine groups. Examples of amine groups include, but are not limited to, methylamine groups, dimethylamine groups, phenylamine groups, diphenylamine groups, naphthylamine groups, 9-methyl-anthracenylamine groups, triphenylamine groups, etc.

[0096] In this specification, among alkyl thio groups, alkyl sulfoxy groups, alkyl aryl groups, alkyl amino groups, alkyl boron groups, alkyl silyl groups, and alkyl amine groups, the alkyl groups are the same as the examples of alkyl groups described above.

[0097] In this specification, the aryl group among the aryloxy group, arylthio group, arylsulfoxy group, arylamino group, arylboron group, arylsilyl group, and arylamine group is the same as the examples of aryl groups described above.

[0098] In this specification, direct linkage may mean a single linkage.

[0099] Meanwhile, in this specification " " and " " means the location where it is connected.

[0100] Hereinafter, an embodiment of the present invention will be described with reference to the drawings.

[0101] FIG. 1 is a plan view showing one embodiment of a display device (DD). FIG. 2 is a cross-sectional view of the display device (DD) of one embodiment. FIG. 2 is a cross-sectional view showing the portion corresponding to line I-I' of FIG. 1.

[0102] A display device (DD) may include a display panel (DP) and an optical layer (PP) disposed on the display panel (DP). The display panel (DP) includes light-emitting elements (ED-1, ED-2, ED-3). The display device (DD) may include a plurality of light-emitting elements (ED-1, ED-2, ED-3). The optical layer (PP) is disposed on the display panel (DP) to control reflected light from the display panel (DP) caused by external light. The optical layer (PP) may include, for example, a polarizing layer or a color filter layer. Meanwhile, unlike what is shown in the drawings, the optical layer (PP) may be omitted in the display device (DD) of one embodiment.

[0103] A base substrate (BL) may be disposed on the optical layer (PP). The base substrate (BL) may be a member that provides a base surface on which the optical layer (PP) is disposed. The base substrate (BL) may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited thereto, and the base substrate (BL) may be an inorganic layer, an organic layer, or a composite material layer. In addition, unlike what is illustrated, the base substrate (BL) may be omitted in one embodiment.

[0104] A display device (DD) according to one embodiment may further include a filling layer (not shown). The filling layer (not shown) may be disposed between a display element layer (DP-ED) and a base substrate (BL). The filling layer (not shown) may be an organic layer. The filling layer (not shown) may include at least one of an acrylic resin, a silicone resin, and an epoxy resin.

[0105] 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, ED-3) disposed between the pixel defining layers (PDL), and an encapsulation layer (TFE) disposed on the light-emitting elements (ED-1, ED-2, ED-3).

[0106] The base layer (BS) may be a member that provides a base surface on which the display element layer (DP-ED) is placed. The base layer (BS) may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited thereto, and the base layer (BS) may be an inorganic layer, an organic layer, or a composite material layer.

[0107] In one embodiment, the circuit layer (DP-CL) is disposed on the base layer (BS), and the circuit layer (DP-CL) may include a plurality of transistors (not shown). Each of the transistors (not shown) may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer (DP-CL) may include a switching transistor and a driving transistor for driving light-emitting elements (ED-1, ED-2, ED-3) of the display element layer (DP-ED).

[0108] Each of the light-emitting elements (ED-1, ED-2, ED-3) may have the structure of a light-emitting element (ED) according to one embodiment of FIGS. 3 to 6 described below. Each of the light-emitting elements (ED-1, ED-2, ED-3) may include a first electrode (EL1), a hole transport region (HTR), a light-emitting layer (EML-R, EML-G, EML-B), an electron transport region (ETR), and a second electrode (EL2).

[0109] FIG. 2 illustrates an embodiment in which the light-emitting layers (EML-R, EML-G, EML-B) of light-emitting elements (ED-1, ED-2, ED-3) are disposed within an opening (OH) defined in a pixel defining film (PDL), and the hole transport region (HTR), electron transport region (ETR), and second electrode (EL2) are provided as a common layer throughout the light-emitting elements (ED-1, ED-2, ED-3). However, the embodiment is not limited thereto, and unlike FIG. 2, in one embodiment, the hole transport region (HTR) and electron transport region (ETR) may be patterned and provided within the opening (OH) defined in the pixel defining film (PDL). For example, in one embodiment, the hole transport region (HTR), light-emitting layer (EML-R, EML-G, EML-B), and electron transport region (ETR) of the light-emitting element (ED-1, ED-2, ED-3) may be provided by patterning using an inkjet printing method.

[0110] The encapsulation layer (TFE) may cover light-emitting elements (ED-1, ED-2, ED-3). The encapsulation layer (TFE) may seal a display element layer (DP-ED). The encapsulation layer (TFE) may be a thin film encapsulation layer. The encapsulation layer (TFE) may be a single layer or a plurality of layers stacked. The encapsulation layer (TFE) includes at least one insulating layer. The encapsulation layer (TFE) according to one embodiment may include at least one inorganic film (hereinafter, encapsulation inorganic film). Additionally, the encapsulation layer (TFE) according to one embodiment may include at least one organic film (hereinafter, encapsulation organic film) and at least one encapsulation inorganic film.

[0111] The encapsulation inorganic film protects the display device layer (DP-ED) from moisture / oxygen, and the encapsulation organic film protects the display device layer (DP-ED) from foreign substances such as dust particles. The encapsulation inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, or aluminum oxide, but is not particularly limited thereto. The encapsulation organic film may include acrylic compounds, epoxy compounds, etc. The encapsulation organic film may include photopolymerizable organic materials and is not particularly limited thereto.

[0112] The encapsulation layer (TFE) can be placed on the second electrode (EL2) and can fill the opening (OH).

[0113] Referring to FIGS. 1 and 2, the display device (DD) may include a non-emissive region (NPXA) and emissive regions (PXA-R, PXA-G, PXA-B). Each of the emissive regions (PXA-R, PXA-G, PXA-B) may be a region where light generated from each of the emissive elements (ED-1, ED-2, ED-3) is emitted. The emissive regions (PXA-R, PXA-G, PXA-B) may be spaced apart from each other in a plane.

[0114] Each of the light-emitting regions (PXA-R, PXA-G, PXA-B) may be a region separated by a pixel defining film (PDL). Non-light-emitting regions (NPXA) may be regions between adjacent light-emitting regions (PXA-R, PXA-G, PXA-B) and may be regions corresponding to the pixel defining film (PDL). Meanwhile, in this specification, each of the light-emitting regions (PXA-R, PXA-G, PXA-B) may correspond to a pixel. The pixel defining film (PDL) may separate light-emitting elements (ED-1, ED-2, ED-3). The light-emitting layers (EML-R, EML-G, EML-B) of the light-emitting elements (ED-1, ED-2, ED-3) may be separated by being placed in an opening (OH) defined in the pixel defining film (PDL).

[0115] The light-emitting regions (PXA-R, PXA-G, PXA-B) can be divided into multiple groups according to the color of light generated from the light-emitting elements (ED-1, ED-2, ED-3). In the display device (DD) of one embodiment illustrated in FIGS. 1 and 2, three light-emitting regions (PXA-R, PXA-G, PXA-B) emitting red light, green light, and blue light are illustrated as examples. For example, the display device (DD) of one embodiment may include a red light-emitting region (PXA-R), a green light-emitting region (PXA-G), and a blue light-emitting region (PXA-B) that are distinct from each other.

[0116] In a display device (DD) according to one embodiment, a plurality of light-emitting elements (ED-1, ED-2, ED-3) may emit light in different wavelength regions. For example, in one embodiment, the display device (DD) may include a first light-emitting element (ED-1) that emits red light, a second light-emitting element (ED-2) that emits green light, and a third light-emitting element (ED-3) that emits blue light. That is, the red light-emitting region (PXA-R), the green light-emitting region (PXA-G), and the blue light-emitting region (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.

[0117] However, the embodiments are not limited thereto, and the first to third light-emitting elements (ED-1, ED-2, ED-3) may emit light in the same wavelength range, or at least one may emit light in a different wavelength range. For example, the first to third light-emitting elements (ED-1, ED-2, ED-3) may all emit blue light.

[0118] In a display device (DD) according to one embodiment, the light-emitting regions (PXA-R, PXA-G, PXA-B) may be arranged in a stripe shape. Referring to FIG. 1, a plurality of red light-emitting regions (PXA-R), a plurality of green light-emitting regions (PXA-G), and a plurality of blue light-emitting regions (PXA-B) may each be aligned along a second directional axis (DR2). Additionally, they may be arranged alternately along a first directional axis (DR1) in the order of red light-emitting regions (PXA-R), green light-emitting regions (PXA-G), and blue light-emitting regions (PXA-B).

[0119] In FIGS. 1 and 2, the areas of the light-emitting regions (PXA-R, PXA-G, PXA-B) are all depicted as similar, but the embodiment is not limited thereto, and the areas of the light-emitting regions (PXA-R, PXA-G, PXA-B) may differ from one another depending on the wavelength range of the emitted light. Meanwhile, the areas of the light-emitting regions (PXA-R, PXA-G, PXA-B) may refer to the area when viewed on a plane defined by the first directional axis (DR1) and the second directional axis (DR2).

[0120] Meanwhile, the arrangement of the light-emitting regions (PXA-R, PXA-G, PXA-B) is not limited to that shown in FIG. 1, and the order in which the red light-emitting region (PXA-R), the green light-emitting region (PXA-G), and the blue light-emitting region (PXA-B) are arranged can be provided in various combinations according to the characteristics of the display quality required by the display device (DD). For example, the arrangement of the light-emitting regions (PXA-R, PXA-G, PXA-B) may be a pentile arrangement or a diamond arrangement.

[0121] Additionally, the areas of the light-emitting regions (PXA-R, PXA-G, PXA-B) may differ from each other. For example, in one embodiment, the area of ​​the green light-emitting region (PXA-G) may be smaller than the area of ​​the blue light-emitting region (PXA-B), but the embodiment is not limited thereto.

[0122] Hereinafter, FIGS. 3 to 6 are cross-sectional views schematically illustrating a light-emitting element according to one embodiment. A light-emitting element (ED) according to one embodiment may include a first electrode (EL1), a hole transport region (HTR), a light-emitting layer (EML), an electron transport region (ETR), and a second electrode (EL2) that are sequentially stacked.

[0123] FIG. 4 shows a cross-sectional view of a light-emitting device (ED) of an embodiment in which, compared with FIG. 3, 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). FIG. 5 also shows a cross-sectional view of a light-emitting device (ED) of an embodiment in which, compared with FIG. 3, 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). FIG. 6 shows a cross-sectional view of a light-emitting device (ED) of an embodiment in which, compared with FIG. 4, a capping layer (CPL) disposed on a second electrode (EL2).

[0124] The first electrode (EL1) has conductivity. The first electrode (EL1) may be formed of a metal material, a metal alloy, or a conductive compound. The first electrode (EL1) may be an anode or a cathode. However, the embodiments are not limited thereto. Additionally, the first electrode (EL1) may be a pixel electrode. The first electrode (EL1) may be a transmissive electrode, a transmissive electrode, or a reflective electrode. The first electrode (EL1) may be a transmissive electrode, a transmissive electrode, or a reflective electrode. The first electrode (EL1) may comprise 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, at least two compounds selected from these, at least two mixtures selected from these, or oxides thereof.

[0125] If the first electrode (EL1) is a transparent electrode, the first electrode (EL1) may include a transparent metal oxide, for example, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. If the first electrode (EL1) is a semitransparent electrode or a reflective electrode, the first electrode (EL1) may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca (layered structure of LiF and Ca), LiF / Al (layered structure of LiF and Al), Mo, Ti, W, or a compound or mixture thereof (for example, a mixture of Ag and Mg). Alternatively, the first electrode (EL1) may have a plurality of layer structures including a reflective film or a semi-transparent film formed of the above material and a transparent conductive film formed of ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. For example, the first electrode (EL1) may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto. Furthermore, the embodiments are not limited thereto, and the first electrode (EL1) may include the metal material described above, a combination of two or more metal materials selected from the metal materials described above, or oxides of the metal materials described above. The thickness of the first electrode (EL1) may be about 700 Å to about 10000 Å. For example, the thickness of the first electrode (EL1) may be about 1000 Å to about 3000 Å.

[0126] A hole transport region (HTR) is provided on the first electrode (EL1). The hole transport region (HTR) may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer or a light-emitting auxiliary layer (not shown), and an electron blocking layer (EBL). The thickness of the hole transport region (HTR) may be, for example, about 50 Å to about 15,000 Å.

[0127] The hole transport region (HTR) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0128] 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 a single-layer structure composed of a hole injection material and a hole transport material. Additionally, the hole transport region (HTR) may have a single-layer structure composed of multiple different materials, or may have a structure of a hole injection layer (HIL) / hole transport layer (HTL), a hole injection layer (HIL) / hole transport layer (HTL) / buffer layer (not shown), a hole injection layer (HIL) / buffer layer (not shown), a hole transport layer (HTL) / buffer layer (not shown), or a hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) stacked sequentially from the first electrode (EL1), but the embodiments are not limited thereto.

[0129] Hole transport regions (HTRs) can be formed using various methods such as vacuum deposition, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0130] The hole transport region (HTR) may include a compound represented by the following chemical formula H-1.

[0131] [Chemical Formula H-1]

[0132]

[0133] In the above chemical formula H-1, L1 and L2 may each independently be a direct linkage, substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms. a and b may each independently be integers from 0 to 10. Meanwhile, if a or b is an integer of 2 or more, a plurality of L1 and L2 may each independently be a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.

[0134] In chemical formula H-1, Ar1 and Ar2 may each independently be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. Additionally, in chemical formula H-1, Ar3 may be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[0135] The compound represented by the above formula H-1 may be a monoamine compound. Alternatively, the compound represented by the above formula H-1 may be a diamine compound in which at least one of Ar-1 to Ar3 comprises an amine group as a substituent. Additionally, the compound represented by the above formula H-1 may be a carbazole compound comprising a carbazole group substituted or unsubstituted on at least one of Ar1 and Ar2, or a fluorene compound comprising a fluorene group substituted or unsubstituted on at least one of Ar1 and Ar2.

[0136] The compound represented by the chemical formula H-1 may be represented as any one of the compounds in the following compound group H. However, the compounds listed in the following compound group H are exemplary, and the compound represented by the chemical formula H-1 is not limited to those listed in the following compound group H.

[0137] [Compound Group H]

[0138]

[0139] The hole transport region (HTR) is phthalocyanine compounds such as copper phthalocyanine, DNTPD(N 1 ,N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4-di-m-tolylbenzene-1,4-diamine)), m-MTDATA(4,4',4"-[tris(3-methylphenyl)phenylamino] triphenylamine), TDATA(4,4'4"-Tris(N,N-diphenylamino)triphenylamine), 2-TNATA(4,4',4"-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine), PEDOT / PSS(Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), PANI / DBSA(Polyaniline / Dodecylbenzenesulfonic acid), PANI / CSA(Polyaniline / Camphor sulfonicacid), PANI / PSS(Polyaniline / Poly(4-styrenesulfonate)), NPB(N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), 트리페닐아민을 포함하는 폴리에테르케톤(TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium [Tetrakis(pentafluorophenyl)borate], HATCN(dipyrazino[2,3-f: 2',3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile) 등을 포함할 수 있다.

[0140] The hole transport region (HTR) may include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine) and TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB (N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), TAPC (4,4′-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD (4,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), mCP (1,3-Bis(N-carbazolyl)benzene), etc. there is.

[0141] Additionally, the hole transport region (HTR) may include CzSi (9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), CCP (9-phenyl-9H-3,9'-bicarbazole), or mDCP (1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene), etc.

[0142] The hole transport region (HTR) may include the compounds of the hole transport region described above in at least one of the hole injection layer (HIL), the hole transport layer (HTL), and the electron blocking layer (EBL). The thickness of the hole transport region (HTR) may be about 100 Å to about 10000 Å, for example, about 100 Å to about 5000 Å. If the hole transport region (HTR) includes the hole injection layer (HIL), the thickness of the hole injection layer (HIL) may be, for example, about 30 Å to about 1000 Å. If the hole transport region (HTR) includes the hole transport layer (HTL), the thickness of the hole transport layer (HTL) may be about 30 Å to about 1000 Å. For example, if the hole transport region (HTR) includes the electron blocking layer (EBL), the thickness of the electron blocking layer (EBL) may be about 10 Å to about 1000 Å. When the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) satisfy the ranges described above, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

[0143] In addition to the aforementioned materials, the hole transport region (HTR) may further include a charge-generating material to enhance conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within 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 metal halide compound, a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, p-dopants may include metal halide compounds such as CuI and RbI, quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-7,7'8,8-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide, and cyano group-containing compounds such as HATCN (dipyrazino[2,3-f: 2',3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile) and NDP9 (4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylidene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile), but the examples are not limited thereto.

[0144] As described above, the hole transport region (HTR) may further include at least one of a buffer layer (not shown) and an electron blocking layer (EBL) in addition to the hole injection layer (HIL) and the hole transport layer (HTL). The buffer layer (not shown) can increase light emission efficiency by compensating for the resonance distance according to the wavelength of light emitted from the light-emitting layer (EML). The material included in the buffer layer (not shown) may be a material that can be included in the hole transport region (HTR). The electron blocking layer (EBL) is a layer that serves to prevent electron injection from the electron transport region (ETR) into the hole transport region (HTR).

[0145] An emissive layer (EML) is provided on a hole transport region (HTR). The emissive layer (EML) may have a thickness of, for example, about 100 Å to about 1000 Å or about 100 Å to about 300 Å. The emissive layer (EML) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0146] In a light-emitting device (ED) of one embodiment, the light-emitting layer (EML) may comprise a first compound and may comprise at least one of second to fourth compounds. The first to fourth compounds may be different from each other. The first compound may be an organometallic compound represented by the following chemical formula 1.

[0147] [Chemical Formula 1]

[0149]

[0150] In Chemical Formula 1, M can be Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, or Os. A1 to A3, and A 41 To A 44Each may independently be a ring-forming hydrocarbon ring having 5 to 60 carbon atoms, or a heterocycle having 1 to 60 carbon atoms. A1 to A3 may all be identical, or at least one may be different from the others. A 41 To A 44 All of them may be the same, or at least one may be different from the rest.

[0151] R1 to R3, and R 41 to R 44 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 3 to 30 carbon atoms. Specifically, R1 to R3, and R 41 to R 44 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted phenyl group. R1 to R3 may all be the same, or at least one may be different from the others. R 41 to R 44 All of them may be the same, or at least one may be different from the rest.

[0152] b1 to b3 may each be an integer between 0 and 4 independently. If b1 is an integer of 2 or more, multiple R1s may all be the same, or at least one R1 may be different from the rest. If b2 and b3 are integers of 2 or more, the same content as the relationship between b1 and R1 may apply to the relationship between b2 and R2 and the relationship between b3 and R3.

[0153] b41 to b44 may each independently be an integer between 0 and 3. If b41 is an integer of 2 or more, multiple R 41All of them may be identical, or at least one may be different from the rest. If b42 to b44 are integers greater than or equal to 2, b42 and R 42 The relationship between b43 and R 43 The relationship of, and b44 and R 44 Each of the relationships is b 41 and R 41 The same content as described above may apply to the relationship with.

[0154] L1 to L4 are each independently, directly combined, *-O-*', *-S-*', *-C(R 11 )(R 12 )-*', *-C(R 13 )=*', *-C(R 14 )=C(R 15 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 16 )-*', *-N(R 17 )-*', *-P(R 18 )(R 19 )-*', *-Si(R 20 )(R 21 )-*', and *-Ge(R 22 )(R 23 It may be selected from )-*'. L1 to L4 may all be identical, or at least one may be different from the others.

[0155] R 11 to R 23 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms. 11 to R 23 All of them may be the same, or at least one may be different from the rest.

[0156] n1 and n3 can each be independently integers from 0 to 3. If n1 is 0, A1 and A2 may not be combined. If n1 is an integer of 2 or greater, multiple L1s may all be identical, or at least one may be different from the rest. If n3 is 0, A3 and It may be uncombined. If n3 is an integer greater than or equal to 2, multiple L3s may all be identical, or at least one may be different from the rest.

[0157] n2 and n4 may each be independently integers from 1 to 3. If n2 is an integer of 2 or more, multiple L2s may all be the same or at least one may be different from the rest. If n4 is an integer of 2 or more, multiple L4s may all be the same or at least one may be different from the rest.

[0158] In Chemical Formula 1 " " can be a single bond or a double bond. For example, " If " is a single bond, M and A1 are joined by a single bond, and " If 'a' is a double bond, then M and A2 may be bonded by a double bond.

[0159] Chemical formula 1 may be represented by the following chemical formula 2. Chemical formula 2 is M, A in chemical formula 1. 41 To A 44 It is a specification of , L2, and n2.

[0160] [Chemical Formula 2]

[0161]

[0162] In Chemical Formula 2, X1 and X2 may each independently be CRa or N. X1 and X2 may be the same or different from each other. Ra may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms.

[0163] In Chemical Formula 2, A1 to A3, n1 to n4, L1 to L4, b1 to b3, b41 to b44, R1 to R3, and R 41 to R 44 The same content as defined in Chemical Formula 1 can be applied.

[0164] Chemical formula 2 may be represented by the following chemical formula 3-1 or chemical formula 3-2. Chemical formula 3-1 is the case where X1 and X2 in chemical formula 2 are "CH". Chemical formula 3-2 is the case where X1 and X2 in chemical formula 2 are "N".

[0165] [Chemical Formula 3-1]

[0166]

[0167] [Chemical Formula 3-2]

[0168]

[0169] In Chemical Formula 3-1 and Chemical Formula 3-2, A1 to A3, n1, n3, n4, L1, L3, L4, b1 to b3, b41 to b44, R1 to R3, and R 41 to R 44 The same definition as that in Chemical Formula 1 above may be applied. Meanwhile, in Chemical Formula 3-2, R 43 and R 44 Each can be a hydrogen atom.

[0170] Chemical formula 3-1 can be represented by the following chemical formula 3A or chemical formula 3B. Chemical formula 3A is the case where n4 is 1 in chemical formula 3-1 and L4 is a direct bond. Chemical formula 3B is the case where n4 is 1 in chemical formula 3-1 and NR 17 This is the case.

[0171] [Chemical Formula 3A]

[0172]

[0173] [Chemical Formula 3B]

[0174]

[0175] In Chemical Formulas 3A and 3B, A1 to A3, n1, n3, L1, L3, b1 to b3, b41 to b44, R1 to R3, R 41 to R 44 , and R 17 The same provisions as defined in Chemical Formula 1 may apply to . Meanwhile, in Chemical Formula 3B, the above R 17 It may be a substituted or unsubstituted phenyl group.

[0176] Chemical formula 2 may be represented by the following chemical formula 4. Chemical formula 4 is a specification of A1 to A3 in chemical formula 2.

[0177] [Chemical Formula 4]

[0178]

[0179] In Chemical Formula 4, n4, L4, b2, b3, b41 to b44, R1 to R3, R 41 to R 44 X1 and X2 may be subject to the same definitions as those in Chemical Formula 2.

[0180] Chemical formula 1 may be represented by any one of the compounds of compound group 1 below.

[0181] [Compound Group 1]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0189]

[0190]

[0191] The organometallic compound of one embodiment has a structure in which four ligands are bound to a central metal, and one of the ligands is Spirobiacridine. The organometallic compound has a structure in which Spirobiacridine is bound to a central metal, and large 3 MLCT (Metal to Ligand Charge Transfer) value and large 3 It can have MC (3 Metal Centered state) values. A light-emitting device (ED) of one embodiment is 3 By including an organometallic compound with a large MLCT value in the emissive layer (EML), excellent color purity, high luminous efficiency, and long lifespan characteristics can be achieved.

[0192] The organometallic compound of one embodiment represented by Chemical Formula 1 can be used as a phosphorescent light-emitting material. For example, the organometallic compound of one embodiment can be used as a phosphorescent light-emitting dopant that emits blue light.

[0193] The organometallic compound of one embodiment has a central emission wavelength in the wavelength region of 490 nm or less ( maxIt may be a luminescent material having ). For example, the organometallic compound of one embodiment represented by Chemical Formula 1 may be a luminescent material having a central wavelength of emission in the wavelength range of 450 nm or more and 470 nm or less. That is, the organometallic compound of one embodiment may be a blue phosphorescent dopant. However, the embodiments are not limited thereto.

[0194] In the light-emitting device (ED) of one embodiment shown in FIGS. 3 to 6, the light-emitting layer (EML) may include a host and a dopant, and the light-emitting layer (EML) may include the organometallic compound of the above-described embodiment as a light-emitting dopant.

[0195] In a light-emitting device (ED) of one embodiment, the light-emitting layer (EML) may comprise different first to third compounds. The first compound may be represented by Formula 1. The first compound may be a phosphorescent dopant, the second compound may be a first host, and the third compound may be a second host. In one embodiment, the second compound may be a hole-transporting host, and the third compound may be an electron-transporting host.

[0196] A light-emitting device (ED) of one embodiment may include at least one compound of the following HT-1 to HT-4 as a hole-transporting host in the light-emitting layer (EML).

[0197]

[0198] In addition, the light-emitting element (ED) of one embodiment may include at least one compound of the following ET-1 to ET-3 as an electron transport host in the light-emitting layer (EML).

[0199]

[0200] An electron-transporting host and a hole-transporting host may combine to form an exciplex. The exciplex can transfer energy to a phosphorescent dopant through energy transfer, thereby causing luminescence.

[0201] The triplet energy of the exciplex formed by the hole-transporting host and the electron-transporting host may correspond to the difference between the LUMO (Lowest Unoccupied Molecular Orbital) energy level of the electron-transporting host and the HOMO (Highest Occupied Molecular Orbital) energy level of the hole-transporting host. For example, in a light-emitting device, the triplet energy of the exciplex formed by the hole-transporting host and the electron-transporting host may be 2.4 eV or greater and 3.0 eV or less. Additionally, the triplet energy of the exciplex may be a value smaller than the energy gap of each host material. The energy gap may be the difference between the LUMO energy level and the HOMO energy level. For example, the energy gap of each of the hole-transporting host and the electron-transporting host may be approximately 3.0 eV or greater, and the exciplex may have a triplet energy of 3.0 eV or less.

[0202] In one embodiment of the light-emitting device (ED), the light-emitting layer (EML) may include a fourth compound. For example, the fourth compound may be a delayed fluorescence dopant.

[0203] For example, the fourth compound may be a polycyclic compound comprising at least one electron-donor group having electron-donating properties and at least one electron-withdrawing group having electron-accepting properties, or a condensed ring compound comprising a boron (B) atom and two or more rings condensed. For example, the electron-donor group may be a cyclic heteroaryl group having 3 to 60 carbon atoms, substituted or unsubstituted, comprising a pyridine nitrogen atom. Additionally, the electron-withdrawing group may be a sulfoxide group, a cyano group, or a cyclic heteroaryl group having 1 to 60 carbon atoms, substituted or unsubstituted, comprising a pyrrole nitrogen atom.

[0204] Specifically, the fourth compound may include at least one of the following compounds DF1 to DF9 and DFD1.

[0205]

[0206]

[0207]

[0208] A light-emitting element (ED) of one embodiment may further comprise the following light-emitting layer material in addition to the organometallic compound of the above-described embodiment, the above-described first host and second host, and the delayed fluorescence dopant. In the light-emitting element (ED) of one embodiment, the light-emitting layer (EML) may comprise an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a chrysene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. Specifically, the light-emitting layer (EML) may comprise an anthracene derivative or a pyrene derivative.

[0209] In the light-emitting device (ED) of one embodiment illustrated in FIGS. 3 to 6, the light-emitting layer (EML) may include a host and a dopant, and the light-emitting layer (EML) may include a compound represented by the following chemical formula E-1. The compound represented by the following chemical formula E-1 may be used as a fluorescent host material.

[0210] [Chemical Formula E-1]

[0211]

[0212] In chemical formula E-1, R 31 to R 40Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio 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 1 to 10 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or may form a ring by bonding to an adjacent group. Meanwhile, R 31 to R 40 It can combine with adjacent groups to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring, or an unsaturated heterocyclic ring.

[0213] In chemical formula E-1, c and d can each independently be integers from 0 to 5.

[0214] Chemical formula E-1 may be represented by any one of the following compounds E1 to E19.

[0215]

[0216]

[0217]

[0218]

[0219] In one embodiment, the light-emitting layer (EML) may 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.

[0220] [Chemical Formula E-2a]

[0221]

[0222] In chemical formula E-2a, a is an integer between 0 and 10 inclusive, and La may be a directly bonded, substituted, or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms. Meanwhile, if a is an integer of 2 or more, multiple L a Each may be an independently substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.

[0223] In addition, in chemical formula E-2a, A1 to A5 are each independently N or CR i It could be. 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 thio 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 ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or may form a ring by bonding with an adjacent group. a to R i It can combine with adjacent groups to form a hydrocarbon ring or a heteroring containing N, O, S, etc. as ring-forming atoms.

[0224] Meanwhile, in chemical formula E-2a, two or three selected from A1 to A5 are N and the remainder are CR i It could be.

[0225] [Chemical Formula E-2b]

[0226]

[0227] In chemical formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazole group, or a carbazole group substituted with a ring-forming aryl group having 6 to 30 carbon atoms. b may be a directly bonded, substituted, or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic arylene group having 2 to 30 carbon atoms. b is an integer from 0 to 10, and if b is an integer of 2 or more, multiple L b Each may be an independently substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.

[0228] A compound represented by chemical formula E-2a or chemical formula E-2b may be represented as any one of the compounds in compound group E-2 below. However, the compounds listed in compound group E-2 below are exemplary, and a compound represented by chemical formula E-2a or chemical formula E-2b is not limited to those listed in compound group E-2 below.

[0229] [Compound Group E-2]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235] The emissive layer (EML) may further include common materials known in the art as host materials. For example, the emissive layer (EML) comprises at least one of BCPDS (bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane), POPCPA ((4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide), DPEPO (Bis[2-(diphenylphosphino)phenyl]ether oxide), CBP (4,4'-bis(N-carbazolyl)-1,1'-biphenyl), mCP (1,3-Bis(carbazol-9-yl)benzene), PPF (2,8-Bis(diphenylphosphoryl)dibenzo[b,d]furan), TCTA (4,4',4''-Tris(carbazol-9-yl)-triphenylamine), and TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene) as a host material. It could be.However, this is not limited thereto, and for example, Alq3 (tris(8-hydroxyquinolino)aluminum), ADN (9,10-di(naphthalene-2-yl)anthracene), TBADN (2-tert-butyl-9,10-di(naphth-2-yl)anthracene), DSA (distyrylarylene), CDBP (4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl), MADN (2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), CP1 (Hexaphenyl cyclotriphosphazene), UGH2 (1,4-Bis(triphenylsilyl)benzene), DPSiO3 (Hexaphenylcyclotrisiloxane), DPSiO4 (Octaphenylcyclotetrasiloxane), etc. can be used as host materials.

[0236] The emissive layer (EML) may further include a compound represented by the following chemical formula Ma. The compound represented by the following chemical formula Ma can be used as a phosphorescent dopant material.

[0237] [Chemical Formula Ma]

[0238]

[0239] In the above formula Ma, Y1 to Y4 and Z1 to Z4 are each independently CR1 or N, and R1 to R4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio 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 ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or may form a ring by bonding with an adjacent group. In the formula Ma, m is 0 or 1, and n is 2 or 3. In the formula Ma, when m is 0, n is 3, and when m is 1, n is 2.

[0240] The compound represented by the chemical formula Ma may be represented by any one of the following compounds M-a1 to M-a21. However, the following compounds M-a1 to M-a21 are exemplary, and the compound represented by the chemical formula Ma is not limited to those represented by the following compounds M-a1 to M-a21.

[0242]

[0243]

[0244]

[0246]

[0247]

[0248] The emissive layer (EML) may include a compound represented by any one of the following chemical formulas Fa to Fc. Compounds represented by the following chemical formulas Fa to Fc may be used as fluorescent dopant materials.

[0249] [Chemical Formula Fa]

[0250]

[0251] In the above chemical formula Fa, R a to R j The two selected from among them are each independently It could be replaced by R a to R j middle The remaining elements not substituted may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. In this, Ar1 and Ar2 may each independently be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. For example, at least one of Ar1 and Ar2 may be a heteroaryl group containing O or S as a ring-forming atom.

[0252] [Chemical Formula Fb]

[0253]

[0254] In the above chemical formula Fb, R a and R bEach 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 ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or may form a ring by bonding to an adjacent group. Ar1 to Ar4 may each independently be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.

[0255] In the chemical formula Fb, U and V may each be independently a substituted or unsubstituted ring-forming hydrocarbon ring with 5 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic ring with 2 to 30 carbon atoms.

[0256] In the chemical formula Fb, the number of rings represented by U and V can each be independently 0 or 1. For example, if the number of U or V in the chemical formula Fb is 1, it means that one ring constitutes a condensed ring in the part labeled U or V, and if the number of U or V is 0, it means that there is no ring labeled U or V. Specifically, if the number of U is 0 and the number of V is 1, or if the number of U is 1 and the number of V is 0, the condensed ring having a fluorene core of the chemical formula Fb may be a tetracyclic compound. Furthermore, if the number of both U and V is 0, the condensed ring of the chemical formula Fb may be a tricyclic compound. Additionally, if the number of both U and V is 1, the condensed ring having a fluorene core of the chemical formula Fb may be a pentacyclic compound. [Chemical Formula Fc]

[0257]

[0258] In the chemical formula Fc, A1 and A2 are each 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 cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms. R1 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 thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or forms a ring by bonding with an adjacent group.

[0259] In the chemical formula Fc, A1 and A2 can each independently bond with substituents of adjacent rings to form condensation rings. For example, A1 and A2 each independently NR m In this case, A1 may combine with R4 or R5 to form a ring. Additionally, A2 may combine with R7 or R8 to form a ring.

[0260] In one embodiment, the light-emitting layer (EML) is a known dopant material, styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine (N-BDAVBi)), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and its derivatives (e.g., 2,5,8,11-Tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g., It may include 1,1-dipyrene, 1,4-dipyrenylbenzene, 1,4-Bis(N,N-Diphenylamino)pyrene), etc. The emissive layer (EML) may further include a known phosphorescent dopant material. For example, the phosphorescent dopant may be 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). Specifically, FIrpic(iridium(III) bis(4,6-difluorophenylpyridinato-N,C2 ), Fir6 (Bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III)), or PtOEP (platinum octaethyl porphyrin) can be used as phosphorescent dopants. However, the examples are not limited thereto.

[0261] The emissive layer (EML) may contain a quantum dot material. The core of the quantum dot may be selected from group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group I-IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

[0262] Group II-VI compounds are diatomic compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; ternary compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, and mixtures thereof; and may be selected from the group consisting of four-element compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and mixtures thereof.

[0263] Group III-VI compounds may include binary compounds such as In2S3 and In2Se3, ternary compounds such as InGaS3 and InGaSe3, or any combination thereof.

[0264] Group I-III-VI compounds are ternary compounds selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2CuGaO2, AgGaO2, AgAlO2, and mixtures thereof, or AgInGaS2, It can be selected from four-element compounds such as CuInGaS2.

[0265] III-V group compounds may be selected from the group consisting of diatomic compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. Meanwhile, III-V group compounds may further include a group II metal. For example, InZnP, etc., can be selected as a Group III-II-V compound.

[0266] Group IV-VI compounds may be selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds may be ternary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0267] In this case, the binary, ternary, or quaternary compounds may exist within the particle at a uniform concentration, or they may exist within the same particle with their concentration distributions partially divided into different states. Additionally, they may have a core / shell structure in which one quantum dot surrounds another. In a core / shell structure, there may be a concentration gradient in which the concentration of the element in the shell decreases as it moves toward the core.

[0268] In some embodiments, the quantum dot may have a core-shell structure comprising a core containing the aforementioned nanocrystal and a shell surrounding the core. The shell of the quantum dot may serve as a protective layer to maintain semiconductor properties by preventing chemical degradation of the core and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be a single layer or a multilayer. Examples of the shell of the quantum dot include oxides of metals or non-metals, semiconductor compounds, or combinations thereof.

[0269] For example, the oxide of the metal or nonmetal mentioned above may be exemplified as a binary compound such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, or a ternary compound such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, but the present invention is not limited thereto.

[0270] In addition, the above semiconductor compounds may be examples of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but the present invention is not limited thereto.

[0271] Quantum dots can have a full width of half maximum (FWHM) of the emission wavelength spectrum of about 45 nm or less, preferably about 40 nm or less, and more preferably about 30 nm or less, and color purity or color reproducibility can be improved in this range. In addition, since the light emitted through these quantum dots is emitted in all directions, the viewing angle can be improved.

[0272] In addition, the shape of the quantum dots is not specifically limited to shapes commonly used in the field, but more specifically, shapes such as spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, and nanoplate particles may be used.

[0273] Quantum dots can control the color of the light they emit depending on their particle size, and accordingly, they can have various emission colors such as blue, red, and green.

[0274] In the light-emitting device (ED) of one embodiment illustrated in FIGS. 3 to 6, an electron transport region (ETR) is provided on the light-emitting layer (EML). The electron transport region (ETR) may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL), but the embodiment is not limited thereto.

[0275] The electron transport region (ETR) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0276] For example, the electron transport region (ETR) may have a single-layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or a single-layer structure composed of an electron injection material and an electron transport material. Additionally, the electron transport region (ETR) may have a single-layer structure composed of multiple different materials, or may have an electron transport layer (ETL) / electron injection layer (EIL) or hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) structure stacked sequentially from the emitting layer (EML), but is not limited thereto. The thickness of the electron transport region (ETR) may be, for example, about 1000 Å to about 1500 Å.

[0277] The electron transport region (ETR) can be formed using various methods such as vacuum deposition, spin coating, casting, the Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0278] The electron transport domain (ETR) may include a compound represented by the following chemical formula ET-1.

[0279] [Chemical Formula ET-1]

[0280]

[0281] In the chemical formula ET-1, at least one of X1 to X3 is N and the rest are CR a is. R amay be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. Ar1 to Ar3 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.

[0282] In the formula ET-1, a to c may each be an integer from 0 to 10 or less, independently. In the formula ET-1, L1 to L3 may each be a direct linkage, a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms. Meanwhile, when a to c is an integer of 2 or more, L1 to L3 may each be a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.

[0283] The electron transport domain (ETR) may include anthracene compounds. However, it is not limited thereto, and the electron transport domain (ETR) may include, for example, Alq3(Tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, TPBi(1,3,5-Tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), BCP(2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline), It may include TAZ(3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ(4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olato)aluminum), Bebq2(berylliumbis(benzoquinolin-10-olate)), ADN(9,10-di(naphthalene-2-yl)anthracene), BmPyPhB(1,3-Bis[3,5-di(pyridin-3-yl)phenyl]benzene) and mixtures thereof.

[0284] The electron transport region (ETR) may include at least one of the following compounds ET1 to ET36.

[0285]

[0287] Additionally, the electron transport region (ETR) may include metal halides such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI, lanthanide metals such as Yb, and co-deposited materials of the above 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. Meanwhile, metal oxides such as Li2O and BaO, or Liq(8-hydroxyl-Lithium quinolate), etc., may be used for the electron transport region (ETR), but the examples are not limited thereto. The electron transport region (ETR) may also be composed of a material in which an electron transport material and an insulating organometal salt are mixed. The organometal salt may be a material having an energy band gap of approximately 4 eV or more. Specifically, for example, organometallic salts may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.

[0288] The electron transport region (ETR) may further include at least one of BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), TSPO1 (diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide) and Bphen (4,7-diphenyl-1,10-phenanthroline) in addition to the aforementioned materials, but the examples are not limited thereto.

[0289] The electron transport region (ETR) may include compounds of the electron transport region described above in at least one of the electron injection layer (EIL), electron transport layer (ETL), and hole blocking layer (HBL).

[0290] If the electron transport region (ETR) includes an electron transport layer (ETL), the thickness of the electron transport layer (ETL) may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. If the thickness of the electron transport layer (ETL) satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage. If the electron transport region (ETR) includes an electron injection layer (EIL), the thickness of the electron injection layer (EIL) may be about 1 Å to about 100 Å, or about 3 Å to about 90 Å. If the thickness of the electron injection layer (EIL) satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0291] 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 are not limited thereto. For example, if the first electrode (EL1) is an anode, the second electrode (EL2) may be a cathode, and if the first electrode (EL1) is a cathode, the second electrode (EL2) may be an anode. The second electrode may comprise 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, two or more compounds selected from these, two or more mixtures selected from these, or oxides thereof.

[0292] The second electrode (EL2) may be a transmissive electrode, a semitransmissive electrode, or a reflective electrode. If the second electrode (EL2) is a transmissive electrode, the second electrode (EL2) may be made of a transparent metal oxide, for example, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc.

[0293] When the second electrode (EL2) is a semi-transparent electrode or a reflective electrode, the second electrode (EL2) may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, Yb, W, or a compound or mixture containing these (e.g., AgMg, AgYb, or MgAg). Alternatively, the second electrode (EL2) may have a plurality of layer structures including a reflective film or semi-transparent film formed of the above material and a transparent conductive film formed of ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. For example, the second electrode (EL2) may include the metal material described above, a combination of two or more metal materials selected from the metal materials described above, or oxides of the metal materials described above.

[0294] Although not illustrated, the second electrode (EL2) can be connected to an auxiliary electrode. When the second electrode (EL2) is connected to an auxiliary electrode, the resistance of the second electrode (EL2) can be reduced.

[0295] Meanwhile, a capping layer (CPL) may be further disposed on the second electrode (EL2) of the light-emitting element (ED) of one embodiment. The capping layer (CPL) may include a multilayer or a single layer.

[0296] In one embodiment, the capping layer (CPL) may be an organic layer or an inorganic layer. For example, if the capping layer (CPL) includes an inorganic material, the inorganic material may be an alkali metal compound such as LiF, an alkaline earth metal compound such as MgF2, SiON, or SiN X It may include SiOy, etc.

[0297] For example, when the capping layer (CPL) contains an organic material, the organic material may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, TPD15 (N4,N4,N4',N4'-tetra (biphenyl-4-yl) biphenyl-4,4'-diamine), TCTA (4,4',4"- Tris (carbazol sol-9-yl) triphenylamine), etc., or may include an epoxy resin or an acrylate such as methacrylate. However, the examples are not limited thereto, and the capping layer (CPL) may include at least one of the following compounds P1 to P5.

[0298]

[0299]

[0300] Meanwhile, the refractive index of the capping layer (CPL) may be 1.6 or higher. Specifically, for light in a wavelength range of 550 nm or more and 660 nm or less, the refractive index of the capping layer (CPL) may be 1.6 or higher.

[0301] FIGS. 7 and FIGS. 8 are cross-sectional views of a display device according to one embodiment. In the following description of the display device according to one embodiment with reference to FIGS. 7 and FIGS. 8, details that overlap with those described in FIGS. 1 to 6 above will not be explained again, and the differences will be explained primarily.

[0302] Referring to FIG. 7, a display device (DD) according to one embodiment 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).

[0303] In one embodiment illustrated in FIG. 7, the display panel (DP) includes a base layer (BS), a circuit layer (DP-CL) provided on the base layer (BS), and a display element layer (DP-ED), and the display element layer (DP-ED) may include a light-emitting element (ED).

[0304] The light-emitting element (ED) may include a first electrode (EL1), a hole transport region (HTR) disposed on the first electrode (EL1), a light-emitting layer (EML) disposed on the hole transport region (HTR), an electron transport region (ETR) disposed on the light-emitting layer (EML), and a second electrode (EL2) disposed on the electron transport region (ETR). Meanwhile, the structure of the light-emitting element (ED) shown in FIG. 7 may be identical to the structure of the light-emitting element of FIG. 3 to FIG. 6 described above.

[0305] Referring to FIG. 7, the light-emitting layer (EML) may be disposed within an opening (OH) defined in the pixel defining film (PDL). For example, the light-emitting layer (EML) provided corresponding to each light-emitting region (PXA-R, PXA-G, PXA-B) separated by the pixel defining film (PDL) may emit light of the same wavelength range. In a display device (DD) of one embodiment, the light-emitting layer (EML) may emit blue light. Meanwhile, unlike illustrated, in one embodiment, the light-emitting layer (EML) may be provided as a common layer over the entire light-emitting regions (PXA-R, PXA-G, PXA-B).

[0306] A light control layer (CCL) may be placed on a display panel (DP). The light control layer (CCL) may include a light converter. The light converter may be a quantum dot or a phosphor. The light converter may emit light by converting the wavelength of the provided light. That is, the light control layer (CCL) may be a layer containing quantum dots or a layer containing a phosphor.

[0307] The optical control layer (CCL) may include a plurality of optical control units (CCP1, CCP2, CCP3). The optical control units (CCP1, CCP2, CCP3) may be spaced apart from each other.

[0308] Referring to FIG. 7, a split pattern (BMP) may be placed between spaced-apart light control units (CCP1, CCP2, CCP3), but the embodiment is not limited thereto. In FIG. 7, the split pattern (BMP) is shown as not overlapping with the light control units (CCP1, CCP2, CCP3), but the edges of the light control units (CCP1, CCP2, CCP3) may overlap with the split pattern (BMP) at least partially.

[0309] The light control layer (CCL) may include a first light control unit (CCP1) comprising a first quantum dot (QD1) that converts a first color light provided by a light-emitting element (ED) into a second color light, a second light control unit (CCP2) comprising a second quantum dot (QD2) that converts the first color light into a third color light, and a third light control unit (CCP3) that transmits the first color light.

[0310] In one embodiment, the first light control unit (CCP1) may provide red light, which is the second color light, and the second light control unit (CCP2) may provide green light, which is the third color light. The third light control unit (CCP3) may transmit and provide blue light, which is 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. The same as described above may apply to the quantum dots (QD1, QD2).

[0311] Additionally, the light control layer (CCL) may further include a scatterer (SP). The first light control unit (CCP1) may include a first quantum dot (QD1) and a scatterer (SP), the second light control unit (CCP2) may include a second quantum dot (QD2) and a scatterer (SP), and the third light control unit (CCP3) may not include a quantum dot and may include a scatterer (SP).

[0312] The scatterer (SP) may be an inorganic particle. For example, the scatterer (SP) may comprise at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer (SP) may comprise any one of TiO2, ZnO, Al2O3, SiO2, and hollow silica, or may be a mixture of two or more materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.

[0313] Each of the first light control unit (CCP1), the second light control unit (CCP2), and the third light control unit (CCP3) may include a base resin (BR1, BR2, BR3) that disperses quantum dots (QD1, QD2) and scatterers (SP). In one embodiment, the first light control unit (CCP1) may include a first quantum dot (QD1) and a scatterer (SP) dispersed within the first base resin (BR1), the second light control unit (CCP2) may include a second quantum dot (QD2) and a scatterer (SP) dispersed within the second base resin (BR2), and the third light control unit (CCP3) may include a scatterer (SP) dispersed within the third base resin (BR3). The base resin (BR1, BR2, BR3) is a medium in which quantum dots (QD1, QD2) and scatterers (SP) are dispersed, and can be composed of various resin compositions that can generally be referred to as binders. For example, the base resin (BR1, BR2, BR3) may be an acrylic resin, a urethane resin, a silicone resin, an epoxy resin, etc. The base resin (BR1, BR2, BR3) may be a transparent resin. In one embodiment, the first base resin (BR1), the second base resin (BR2), and the third base resin (BR3) may each be the same or different from one another.

[0314] The light control layer (CCL) may include a barrier layer (BFL1). The barrier layer (BFL1) may serve to prevent the penetration of moisture and / or oxygen (hereinafter referred to as 'moisture / oxygen'). The barrier layer (BFL1) may be placed on the light control units (CCP1, CCP2, CCP3) to block the light control units (CCP1, CCP2, CCP3) from being exposed to moisture / oxygen. Meanwhile, the barrier layer (BFL1) may cover the light control units (CCP1, CCP2, CCP3). Additionally, a barrier layer (BFL2) may be provided between the light control units (CCP1, CCP2, CCP3) and the color filter layer (CFL).

[0315] The barrier layer (BFL1, BFL2) may include at least one inorganic layer. That is, the barrier layer (BFL1, BFL2) may be formed by including an inorganic material. For example, the barrier layer (BFL1, BFL2) may be formed by including silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, or a metal thin film with secured light transmittance. Meanwhile, the barrier layer (BFL1, BFL2) may further include an organic film. The barrier layer (BFL1, BFL2) may be composed of a single layer or multiple layers.

[0316] In a display device (DD) of one embodiment, a color filter layer (CFL) may be placed on a light control layer (CCL). For example, the color filter layer (CFL) may be placed directly on the light control layer (CCL). In this case, the barrier layer (BFL2) may be omitted.

[0317] The color filter layer (CFL) may include a light-blocking portion (BM) and filters (CF1, CF2, CF3). The color filter layer (CFL) may include a first filter (CF1) that transmits a second color light, a second filter (CF2) that transmits a third color light, and a third filter (CF3) that transmits a 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. Each of the filters (CF1, CF2, CF3) may include a polymer photosensitive resin and a pigment or dye. The first filter (CF1) may include a red pigment or dye, the second filter (CF2) may include a green pigment or dye, and the third filter (CF3) may include a blue pigment or dye. Meanwhile, the embodiments are not limited thereto, and the third filter (CF3) may not contain pigment or dye. The third filter (CF3) may contain a polymer photosensitive resin and not contain pigment or dye. The third filter (CF3) may be transparent. The third filter (CF3) may be formed of a transparent photosensitive resin.

[0318] Additionally, in one embodiment, the first filter (CF1) and the second filter (CF2) may be yellow filters. The first filter (CF1) and the second filter (CF2) may also be provided as a single unit without being distinguished from each other.

[0319] The light-blocking portion (BM) may be a black matrix. The light-blocking portion (BM) may be formed by including an organic light-blocking material or an inorganic light-blocking material containing a black pigment or a black dye. The light-blocking portion (BM) may prevent light leakage and distinguish the boundaries between adjacent filters (CF1, CF2, CF3). Additionally, in one embodiment, the light-blocking portion (BM) may be formed of a blue filter.

[0320] Each of the first to third filters (CF1, CF2, CF3) can be positioned corresponding to the red light emission region (PXA-R), the green light emission region (PXA-G), and the blue light emission region (PXA-B), respectively.

[0321] A base substrate (BL) may be disposed on the color filter layer (CFL). The base substrate (BL) may be a component that provides a base surface on which the color filter layer (CFL) and the light control layer (CCL) are disposed. The base substrate (BL) may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited thereto, and the base substrate (BL) may be an inorganic layer, an organic layer, or a composite material layer. In addition, unlike what is illustrated, the base substrate (BL) may be omitted in one embodiment.

[0322] FIG. 8 is a cross-sectional view showing a part of a display device according to one embodiment. FIG. 8 shows a cross-sectional view of a part corresponding to the display panel (DP) of FIG. 7. In the display device (DD-TD) of one embodiment, the light-emitting element (ED-BT) may include a plurality of light-emitting structures (OL-B1, OL-B2, OL-B3). 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, OL-B3) provided by being sequentially stacked in the thickness direction between the first electrode (EL1) and the second electrode (EL2). Each of the light-emitting structures (OL-B1, OL-B2, OL-B3) may include a light-emitting layer (EML, FIG. 7), a hole transport region (HTR), and an electron transport region (ETR) arranged between the light-emitting layer (EML, FIG. 7).

[0323] That is, the light-emitting element (ED-BT) included in the display device (DD-TD) of one embodiment may be a light-emitting element with a tandem structure including a plurality of light-emitting layers.

[0324] In one embodiment illustrated in FIG. 8, the light emitted from each of the light-emitting structures (OL-B1, OL-B2, OL-B3) may all be blue light. However, the embodiment is not limited thereto, and the wavelength range of the light emitted from each of the light-emitting structures (OL-B1, OL-B2, OL-B3) may differ from one another. For example, a light-emitting device (ED-BT) comprising a plurality of light-emitting structures (OL-B1, OL-B2, OL-B3) that emit light in different wavelength ranges may emit white light.

[0325] A charge generation layer (CGL1, CGL2) may be disposed between adjacent light-emitting structures (OL-B1, OL-B2, OL-B3). The charge generation layer (CGL1, CGL2) may include a p-type charge generation layer and / or an n-type charge generation layer.

[0326] Referring to FIG. 9, a display device (DD-b) according to one embodiment may include light-emitting elements (ED-1, ED-2, ED-3) in which two light-emitting layers are stacked. Compared to the display device (DD) of one embodiment shown in FIG. 2, the first to third light-emitting elements (ED-1, ED-2, ED-3) in the embodiment shown in FIG. 9 differ in that they each include two light-emitting layers stacked in the thickness direction. In each of the first to third light-emitting elements (ED-1, ED-2, ED-3), the two light-emitting layers may emit light in the same wavelength range.

[0327] The first light-emitting element (ED-1) may include a first red light-emitting layer (EML-R1) and a second red light-emitting layer (EML-R2). The second light-emitting element (ED-2) may include a first green light-emitting layer (EML-G1) and a second green light-emitting layer (EML-G2). Additionally, the third light-emitting element (ED-3) may include a first blue light-emitting layer (EML-B1) and a second blue light-emitting layer (EML-B2). Light-emitting auxiliary members (OG) may be disposed between the first red light-emitting layer (EML-R1) and the second red light-emitting layer (EML-R2), between the first green light-emitting layer (EML-G1) and the second green light-emitting layer (EML-G2), and between the first blue light-emitting layer (EML-B1) and the second blue light-emitting layer (EML-B2).

[0328] The light-emitting auxiliary part (OG) may include a single layer or multiple layers. The light-emitting auxiliary part (OG) may include a charge generation layer. More specifically, the light-emitting auxiliary part (OG) may include sequentially stacked electron transport regions, charge generation layers, and hole transport regions. The light-emitting auxiliary part (OG) may be provided as a common layer across the entire first to third light-emitting elements (ED-1, ED-2, ED-3). However, the embodiments are not limited thereto, and the light-emitting auxiliary part (OG) may be provided by being patterned within an opening (OH) defined in a pixel defining film (PDL).

[0329] The first red emitting layer (EML-R1), the first green emitting layer (EML-G1), and the first blue emitting layer (EML-B1) may be disposed between the hole transport region (HTR) and the light-emitting auxiliary region (OG). The second red emitting layer (EML-R2), the second green emitting layer (EML-G2), and the second blue emitting layer (EML-B2) may be disposed between the light-emitting auxiliary region (OG) and the electron transport region (ETR).

[0330] That is, the first light-emitting element (ED-1) may include a first electrode (EL1), a hole transport region (HTR), a second red light-emitting layer (EML-R2), a light-emitting auxiliary part (OG), a first red light-emitting layer (EML-R1), an electron transport region (ETR), and a second electrode (EL2) that are sequentially stacked. The second light-emitting element (ED-2) may include a first electrode (EL1), a hole transport region (HTR), a second green light-emitting layer (EML-G2), a light-emitting auxiliary part (OG), a first green light-emitting layer (EML-G1), an electron transport region (ETR), and a second electrode (EL2) that are sequentially stacked. The third light-emitting element (ED-3) may include a first electrode (EL1), a hole transport region (HTR), a second blue light-emitting layer (EML-B2), a light-emitting auxiliary part (OG), a first blue light-emitting layer (EML-B1), an electron transport region (ETR), and a second electrode (EL2) that are sequentially stacked.

[0331] Meanwhile, an optical auxiliary layer (PL) may be disposed on the display element layer (DP-ED). The optical auxiliary layer (PL) may include a polarizing layer. The optical auxiliary layer (PL) is disposed on the display panel (DP) to control reflected light from the display panel (DP) caused by external light. Unlike what is illustrated, the optical auxiliary layer (PL) may be omitted in a display device according to one embodiment.

[0332] Unlike FIGS. 8 and 9, the display device (DD-c) of FIG. 10 is illustrated as including four light-emitting structures (OL-B1, OL-B2, OL-B3, OL-C1). The light-emitting element (ED-CT) may include a first electrode (EL1) and a second electrode (EL2) facing each other, and first to fourth light-emitting structures (OL-B1, OL-B2, OL-B3, OL-C1) sequentially stacked in the thickness direction between the first electrode (EL1) and the second electrode (EL2). Charge generating layers (CGL1, CGL2, CGL3) may be disposed between the first to fourth light-emitting structures (OL-B1, OL-B2, OL-B3, OL-C1). Among the four light-emitting structures, the first to third light-emitting structures (OL-B1, OL-B2, OL-B3) may emit blue light, and the fourth light-emitting structure (OL-C1) may emit green light. However, the embodiments are not limited thereto, and the first to fourth light-emitting structures (OL-B1, OL-B2, OL-B3, OL-C1) may emit light in different wavelength regions.

[0333] The charge generation layer (CGL1, CGL2, CGL3) disposed between adjacent light-emitting structures (OL-B1, OL-B2, OL-B3, OL-C1) may include a p-type charge generation layer and / or an n-type charge generation layer.

[0334] Hereinafter, an organometallic compound according to one embodiment of the present invention and a light-emitting element of one embodiment will be described in detail with reference to examples and comparative examples. Furthermore, the examples described below are illustrative examples to aid in understanding the present invention, and the scope of the present invention is not limited thereto.

[0335] [Example]

[0336] 1. Synthesis of organometallic compounds

[0337] First, regarding the synthesis method of an organometallic compound according to the present embodiment, the synthesis method of Compound 1, Compound 36, Compound 60, and Compound 97 of Compound Group 1 will be specifically explained by example. Furthermore, the synthesis method of an organometallic compound described below is an example, and the synthesis method of an organometallic compound according to the embodiment of the present invention is not limited to the following example.

[0338] (1) Synthesis of Compound 1

[0339] Compound 1 according to one embodiment can be synthesized, for example, by the steps of Reaction Scheme 1-1 to Reaction Scheme 1-3 below.

[0340] [Reaction Equation 1-1]

[0341]

[0342] [Reaction Equation 1-2]

[0343]

[0344] [Reaction Equation 1-3]

[0345]

[0346] 1) Synthesis of intermediate compound 1-a

[0347] 2,6-Diphenylaniline (1.0 eq), 2-iodo-nitrobenzene (2.0 eq), Pd2(dba)3 (10 mol%), Sphos (15 mol%), and Sodium tert-butoxide (3.0 eq) were dissolved in Toluene (0.1 M) and stirred at 110 °C for 12 hours to obtain a reaction product. After cooling the reaction product to room temperature, the organic layer was obtained by extracting it three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize intermediate compound 1-a (yield 70%) using column chromatography (MC:Hexane = volume ratio 1:9).

[0348] 2) Synthesis of intermediate compound 1-b

[0349] Intermediate compound 1-a (1.0 eq), Sn (1.5 eq), and HCl (30 eq) were dissolved in ethanol and stirred at 80°C for 12 hours. The reaction mixture was cooled to room temperature and neutralized with NaOH solution. The organic layer was obtained by extraction with dichloromethane and water, and then filtered through a Celite / silica gel. The filtrate was dried with magnesium sulfate, concentrated, and then used to synthesize intermediate compound 1-b (yield 89%) by column chromatography (MC:Hexane = 1:3).

[0351] 3) Synthesis of intermediate compound 1-c

[0352] 2-Bromotriphenylamine (1.0 eq) was dissolved in anhydrous THF (0.3 M), and then 1.6 M n-BuLi (1.1 eq) was slowly added at -80 °C and stirred for 2 hours. To the above reaction mixture, a solution of 3-methoxy-10-((2-methoxyethoxy)methyl)acridin-9(10H)-one (1.0 eq) dissolved in anhydrous THF (0.2 M) was added and stirred at room temperature for 20 hours, after which a 1.0 M aqueous HCl solution (2.0 eq) was added and stirred again for 20 hours to obtain the reaction mixture. The above reaction mixture was neutralized with K2CO3 and filtered using a silica gel to synthesize the intermediate compound 1-c (yield 55%).

[0354] 4) Synthesis of intermediate compound 1-d

[0355] Intermediate compound 1-c (1.1 eq), 2-bromo-4-tert-butyl-pyridine (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 12 hours to obtain a reaction product. After cooling the reaction product to room temperature, the organic layer was obtained by extracting it three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize intermediate compound 1-d (yield 75%) using column chromatography (EA:Hexane = volume ratio 1:4).

[0357] 5) Synthesis of intermediate compound 1-e

[0358] Intermediate compound 1-d (1.0 eq), HBr, and acetic acid were stirred at 120 °C for 16 hours. After cooling the reaction mixture to room temperature, it was neutralized to pH 7 using an aqueous NaOH solution at 0 °C, and then extracted three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize the intermediate compound 1-e (yield 92%).

[0360] 6) Synthesis of intermediate compound 1-f

[0361] 1,3-Dibromobenzene (1.2 eq), intermediate compound 1-e (1.0 eq), CuI (10 mol%), BPPO ligand (10 mol%), and Potassium phosphate tribasic (2.0 eq) were dissolved in DMF (0.1 M) and stirred at 160 °C for 10 hours. After cooling the reaction mixture to room temperature, the DMF was removed under reduced pressure, and the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate, concentrated, and the intermediate compound 1-f (yield 57%) was synthesized using column chromatography (EA:Hexane = volume ratio 1:10).

[0363] 7) Synthesis of 1-g of intermediate compound

[0364] Intermediate compounds 1-f (1.0 eq), 1-b (1.2 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and Sodium tert-butoxide (2.0 eq) were dissolved in Toluene (0.1 M) and stirred at 110°C for 3 hours. After cooling the reaction mixture to room temperature, the Toluene was removed under reduced pressure, and the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate, concentrated, and 1 g of intermediate compound (yield 90%) was synthesized using column chromatography (EA:Hexane = volume ratio 1:4).

[0366] 8) Synthesis of intermediate compound 1-h

[0367] 1-g (1.0 eq) of the intermediate compound was dissolved in triethyl orthoformate (30 eq), and then 37% HCl (1.5 eq) was added and stirred at 80 °C for 12 hours. After cooling to room temperature, the triethyl orthoformate was concentrated and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate, concentrated, and the intermediate compound 1-h (yield 85%) was synthesized using column chromatography (MC, MC: 5 vol% Methanol).

[0369] 9) Synthesis of intermediate compound 1-i

[0370] Intermediate compound 1-h (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), distilled water was added, and the mixture was stirred at room temperature for 3 to 12 hours. The solid was obtained by washing with distilled water and filtering, and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize intermediate compound 1-i (yield 95%).

[0372] 10) Synthesis of Compound 1

[0373] Intermediate compound 1-i (1.0 eq), Dichloro(1,5-cyclooctadiene)platinum(II) (1.1 eq), and Sodium acetate (2.0 eq) were dissolved in Anhydrous 1,4-dioxane (0.05 M) and stirred at 120 °C for 4 days under nitrogen conditions. After cooling to room temperature, the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize compound 1 (30 vol% MC:Hexane) (yield 25%) using column chromatography.

[0374] (2) Synthesis of Compound 36

[0375] Compound 36 according to one embodiment can be synthesized, for example, by the steps of Reaction Scheme 2-1 and Reaction Scheme 2-2 below.

[0376] [Reaction Equation 2-1]

[0377]

[0378] [Reaction Equation 2-2]

[0379]

[0380]

[0381] 1) Synthesis of intermediate compound 36-a

[0382] (6-fluoro-4-methylpyridin-3-yl)boronic acid (1.0 eq), Bromobenzene-d5 (1.2 eq), Pd(PPh3)4 (5 mol%), and Sodium carbonate (3.0 eq) were dissolved in Dioxane:H2O (0.1 M, volume ratio = 4:1) and stirred at 100 °C for 18 hours to obtain a reaction product. After cooling the reaction product to room temperature, the organic layer was obtained by extracting it three times using an aqueous solution of ethyl acetate and sodium chloride. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize the intermediate compound 36-a (yield 90%) using column chromatography (EA:Hexane = volume ratio 1:20).

[0383] 2) Synthesis of intermediate compound 36-b

[0384] 2-bromo-N-(3-(tert-butyl)phenyl)-N-phenylaniline (1.0 eq) was dissolved in anhydrous THF (0.3 M). 1.6 M n-BuLi (1.1 eq) was slowly added at -80 °C and stirred for 2 hours. A solution of 3-methoxy-10-((2-methoxyethoxy)methyl)acridin-9(10H)-one (1.0 eq) dissolved in anhydrous THF (0.2 M) was added to the reaction mixture and stirred at room temperature for 20 hours. An aqueous solution of HCl (2.0 eq) was added to the reaction mixture and stirred again for 20 hours to obtain the reaction mixture. The reaction mixture was neutralized with K2CO3 and filtered using a silica gel to synthesize the intermediate compound 36-b (yield 57%).

[0386] 3) Synthesis of intermediate compound 36-c

[0387] Intermediate compounds 36-b (1.1 eq), 36-a (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and Sodium tert-butoxide (2.0 eq) were dissolved in Toluene (0.1 M) and stirred at 110 °C for 12 hours to obtain a reaction product. After cooling the reaction product to room temperature, the organic layer was obtained by extracting it three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize intermediate compound 36-c (yield 72%) using column chromatography (EA:Hexane = volume ratio 1:10).

[0389] 4) Synthesis of intermediate compound 36-d

[0390] Intermediate compound 36-c (1.0 eq), HBr, and acetic acid were stirred at 120 °C for 16 hours. After cooling the reaction mixture to room temperature, it was neutralized to pH 7 using an aqueous NaOH solution at 0 °C, and then extracted three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize the intermediate compound 36-d (yield 92%).

[0392] 5) Synthesis of intermediate compound 36-e

[0393] 1,3-Dibromobenzene (1.2 eq), intermediate compound 36-d (1.0 eq), CuI (10 mol%), BPPO ligand (10 mol%), and Potassium phosphate tribasic (2.0 eq) were dissolved in DMF (0.1 M) and stirred at 160 °C for 10 hours. After cooling the reaction mixture to room temperature, the DMF was removed under reduced pressure, and the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate, concentrated, and the intermediate compound 36-e (yield 60%) was synthesized using column chromatography (EA:Hexane = volume ratio 1:10).

[0395] 6) Synthesis of intermediate compound 36-f

[0396] Intermediate compounds 36-e (1.0 eq), 1-b (1.2 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and Sodium tert-butoxide (2.0 eq) were dissolved in Toluene (0.1 M) and stirred at 110°C for 3 hours. After cooling the reaction mixture to room temperature, the Toluene was removed under reduced pressure, and the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate, concentrated, and the intermediate compound 36-f (yield 86%) was synthesized using column chromatography (EA:Hexane = volume ratio 1:4).

[0398] 7) Synthesis of 36-g of intermediate compound

[0399] Intermediate compound 36-f (1.0 eq) was dissolved in triethyl orthoformate (30 eq), and then 37% HCl (1.5 eq) was added and stirred at 80 °C for 12 hours. After cooling to room temperature, the triethyl orthoformate was concentrated and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize intermediate compound 36-g (yield 89%) using column chromatography (MC, MC: 5 vol% Methanol).

[0401] 8) Synthesis of intermediate compound 36-h

[0402] 36-g (1.0 eq) of intermediate compound and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), distilled water was added, and the mixture was stirred at room temperature for 3 to 12 hours. The solid was obtained by washing with distilled water and filtering, and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize intermediate compound 36-h (yield 95%).

[0404] 9) Synthesis of Compound 36

[0405] Intermediate compound 36-h (1.0 eq), Dichloro(1,5-cyclooctadiene)platinum(II) (1.1 eq), and Sodium acetate (2.0 eq) were dissolved in Anhydrous 1,4-dioxane (0.05 M) and stirred at 120 °C for 4 days under nitrogen conditions. After cooling to room temperature, the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize compound 36 (30 vol% MC:Hexane) (yield 23%) using column chromatography.

[0407] (3) Synthesis of Compound 60

[0408] Compound 60 according to one embodiment can be synthesized, for example, by the step of Reaction Scheme 3 below.

[0409] [Reaction Equation 3]

[0410]

[0411] 1) Synthesis of intermediate compound 60-a

[0412] 2-bromo-4-(tert-butyl)-N-(4-(tert-butyl)phenyl)-N-phenylaniline (1.0 eq) was dissolved in anhydrous THF (0.3 M). 1.6 M n-BuLi (1.1 eq) was slowly added at -80 °C and stirred for 2 hours. A solution of 3-methoxy-10-((2-methoxyethoxy)methyl)acridin-9(10H)-one (1.0 eq) dissolved in anhydrous THF (0.2 M) was added to the reaction mixture and stirred at room temperature for 20 hours. An aqueous solution of HCl (2.0 eq) was added to the reaction mixture and stirred again for 20 hours to obtain the reaction mixture. The reaction mixture was neutralized with K2CO3 and filtered using a silica gel to synthesize the intermediate compound 60-a (yield 52%).

[0413] 2) Synthesis of intermediate compound 60-b

[0414] Intermediate compounds 60-a (1.1 eq), 36-a (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and Sodium tert-butoxide (2.0 eq) were dissolved in Toluene (0.1 M) and stirred at 110 °C for 12 hours to obtain a reaction product. After cooling the reaction product to room temperature, the organic layer was obtained by extracting it three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize intermediate compound 60-b (yield 71%) using column chromatography (EA:Hexane = volume ratio 1:10).

[0416] 3) Synthesis of intermediate compound 60-c

[0417] Intermediate compound 60-b (1.0 eq), HBr, and acetic acid were stirred at 120 °C for 16 hours. After cooling the reaction mixture to room temperature, it was neutralized to pH 7 using an aqueous NaOH solution at 0 °C, and then extracted three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize the intermediate compound 60-c (yield 92%).

[0419] 4) Synthesis of intermediate compound 60-d

[0420] 1,3-Dibromobenzene (1.2 eq), intermediate compound 60-c (1.0 eq), CuI (10 mol%), BPPO ligand (10 mol%), and Potassium phosphate tribasic (2.0 eq) were dissolved in DMF (0.1 M) and stirred at 160 °C for 10 hours. After cooling the reaction mixture to room temperature, the DMF was removed under reduced pressure, and the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate, concentrated, and the intermediate compound 60-d (yield 67%) was synthesized using column chromatography (EA:Hexane = volume ratio 1:10).

[0422] 5) Synthesis of intermediate compound 60-e

[0423] Intermediate compounds 60-d (1.0 eq), 1-b (1.2 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and Sodium tert-butoxide (2.0 eq) were dissolved in Toluene (0.1 M) and stirred at 110°C for 3 hours. After cooling the reaction mixture to room temperature, the Toluene was removed under reduced pressure, and the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate, concentrated, and the intermediate compound 60-e (yield 80%) was synthesized using column chromatography (EA:Hexane = volume ratio 1:4).

[0425] 6) Synthesis of the intermediate compound 60-f

[0426] Intermediate compound 60-e (1.0 eq) was dissolved in triethyl orthoformate (30 eq), and then 37% HCl (1.5 eq) was added and stirred at 80 °C for 12 hours. After cooling to room temperature, the triethyl orthoformate was concentrated and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate, concentrated, and then the intermediate compound 60-f (yield 88%) was synthesized using column chromatography (MC, MC: 5 vol% Methanol).

[0428] 7) Synthesis of 60-g of intermediate compound

[0429] Intermediate compound 60-f (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), distilled water was added, and the mixture was stirred at room temperature for 3 to 12 hours. The solid was obtained by washing with distilled water and filtering, and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize intermediate compound 60-g (yield 93%).

[0431] 8) Synthesis of Compound 60

[0432] 60-g (1.0 eq) of intermediate compound, Dichloro(1,5-cyclooctadiene)platinum(II) (1.1 eq), and Sodium acetate (2.0 eq) were dissolved in Anhydrous 1,4-dioxane (0.05 M) and stirred at 120 °C for 4 days under nitrogen conditions. After cooling to room temperature, the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize (30 vol% MC:Hexane) compound 60 (yield 25%) using column chromatography.

[0434] (4) Synthesis of Compound 97

[0435] Compound 97 according to one embodiment can be synthesized, for example, by the step of Reaction Scheme 4 below.

[0436] [Reaction Equation 4]

[0437]

[0438]

[0439] 1) Synthesis of intermediate compound 97-a

[0440] 2-iodo-4-methoxy-1,1'-Biphenyl (1.5 eq), 2'-bromo-[1,1'-biphenyl]-2-amine (1.0 eq), 2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene (0.4 eq), Pd(OAc)2 (10 mol%), and sodium tert-butoxide (1.5 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 18 hours to obtain a reaction product. After cooling the reaction product to room temperature, the toluene solvent was removed by vacuum distillation, and the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate, concentrated, and the intermediate compound 97-a (yield 60%) was synthesized using column chromatography (MC:Hexane = volume ratio 1:10).

[0441] 2) Synthesis of intermediate compound 97-b

[0442] Intermediate compound 97-a (1.0 eq) was dissolved in 1,2-Dichlorobenzene (0.025 M) solvent under nitrogen conditions. 1.0 M BBr3 solution in MC (1.2 eq) was added to the mixture, and the mixture was stirred at 190 °C for 18 hours to obtain a reaction product. The reaction product was cooled to room temperature, the solvent was removed under reduced pressure, and the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate, concentrated, and then intermediate compound 97-b (yield 60%) was synthesized using column chromatography (MC:Hexane = volume ratio 1:4).

[0444] 3) Synthesis of intermediate compound 97-c

[0445] Intermediate compound 97-b (1.0 eq), Pd(PPh3)4 (5 mol%), and K2CO3 (2.0 eq) were dissolved in Dimethoxyethane (DME) : Water (volume ratio = 3:1, 0.1 M) and stirred at 120 °C for 18 hours under nitrogen conditions to obtain the reaction product. After cooling the reaction product to room temperature, the organic layer was obtained by extracting it three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize intermediate compound 97-c (yield 36%) using column chromatography (MC:Hexane = volume ratio 1:20).

[0447] 4) Synthesis of intermediate compound 97-d

[0448] Intermediate compound 97-c (1.1 eq), 2-bromo-4-tert-butyl-pyridine (1.0 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110 °C for 12 hours to obtain a reaction product. After cooling the reaction product to room temperature, the organic layer was obtained by extracting it three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize the intermediate compound 97-d (yield 71%) using column chromatography (EA:Hexane = volume ratio 1:4).

[0450] 5) Synthesis of intermediate compound 97-e

[0451] Intermediate compound 97-d (1.0 eq), HBr, and acetic acid were stirred at 120 °C for 16 hours. After cooling the reaction mixture to room temperature, it was neutralized to pH 7 using an aqueous NaOH solution at 0 °C, and then extracted three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize the intermediate compound 97-e (yield 91%).

[0453] 6) Synthesis of intermediate compound 97-f

[0454] 1,3-Dibromobenzene (1.2 eq), intermediate compound 97-e (1.0 eq), CuI (10 mol%), BPPO ligand (10 mol%), and Potassium phosphate tribasic (2.0 eq) were dissolved in DMF (0.1 M) and stirred at 160 °C for 10 hours. After cooling the reaction mixture to room temperature, the DMF was removed under reduced pressure, and the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate, concentrated, and the intermediate compound 97-f (yield 54%) was synthesized using column chromatography (EA:Hexane = volume ratio 1:10).

[0456] 7) Synthesis of intermediate compound 97-g

[0457] Intermediate compounds 97-f (1.0 eq), [1-b] (1.2 eq), Pd2(dba)3 (5 mol%), Sphos (7 mol%), and Sodium tert-butoxide (2.0 eq) were dissolved in Toluene (0.1 M) and stirred at 110°C for 3 hours. After cooling the reaction mixture to room temperature, the Toluene was removed under reduced pressure, and the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate, concentrated, and synthesized 97 g of intermediate compound (yield 90%) using column chromatography (EA:Hexane = volume ratio 1:4).

[0459] 8) Synthesis of intermediate compound 97-h

[0460] 97-g (1.0 eq) of the intermediate compound was dissolved in triethyl orthoformate (30 eq), and then 37% HCl (1.5 eq) was added and stirred at 80 °C for 12 hours. After cooling to room temperature, the triethyl orthoformate was concentrated and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate, concentrated, and the intermediate compound 97-h (yield 83%) was synthesized using column chromatography (MC, MC: 5 vol% Methanol).

[0462] 9) Synthesis of intermediate compound 97-i

[0463] Intermediate compound 97-h (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), distilled water was added, and the mixture was stirred at room temperature for 3 to 12 hours. The solid was obtained by washing with distilled water and filtering, and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize intermediate compound 97-i (yield 97%).

[0465] 10) Synthesis of Compound 97

[0466] Intermediate compound 97-I (1.0 eq), Dichloro(1,5-cyclooctadiene)platinum(II) (1.1 eq), and Sodium acetate (2.0 eq) were dissolved in Anhydrous 1,4-dioxane (0.05 M) and stirred at 120 °C for 4 days under nitrogen conditions. After cooling to room temperature, the organic layer was obtained by extracting three times with dichloromethane and water. The obtained organic layer was dried with magnesium sulfate and concentrated to synthesize compound 97 (30 vol% MC:Hexane) (yield 25%) using column chromatography.

[0468] 2. Fabrication and Evaluation of Light-Emitting Devices

[0469] (Fabrication of light-emitting devices)

[0470] A light-emitting device of one embodiment containing an organometallic compound of one embodiment in a light-emitting layer was manufactured by the following method. Light-emitting devices of Examples 1 to 4 were fabricated using the above-described compounds 1, 36, 60, and 97 as phosphorescent dopants in the light-emitting layer.

[0471] A light-emitting device of the comparative example was fabricated using the following comparative example compound X1 as a material for the light-emitting dopant of the light-emitting layer.

[0472] Comparative example compounds used in device fabrication are shown below.

[0473] (Comparative example compound)

[0474]

[0475] (Other compounds used in device fabrication)

[0476]

[0477]

[0479] An organic electroluminescent device of one example containing the organometallic compound of the example in the light-emitting layer was manufactured by the following method. As shown in Table 1, the compounds of the above-described example and comparative example were used as dopant materials for the light-emitting layer to fabricate an organic electroluminescent device.

[0480] Specifically, as a substrate and a first electrode, Corning's 15Ω / cm 2 A glass substrate with (1200 Å) ITO formed on it was cut into pieces measuring 50 mm x 50 mm x 0.7 mm, ultrasonically cleaned for 5 minutes each using isopropyl alcohol and pure water, then cleaned by irradiating with ultraviolet light for 30 minutes and exposing to ozone, and then installed in a vacuum deposition apparatus.

[0481] A hole injection layer with a thickness of 600 Å was formed by vacuum depositing 2-TNATA on top of the ITO formed on the organic substrate, and a hole transport layer with a thickness of 300 Å was formed by vacuum depositing NPB on top of the hole injection layer.

[0482] A 400 Å thick light-emitting layer was formed on the upper surface of the hole transport layer by co-depositing ETH66 (the second compound) and HTH29 (the third compound) (weight ratio 3:7), which are co-hosts, and the compounds of the example or comparative examples, which are dopants, such that the weight ratio of the co-host to the dopant is 90:10.

[0483] An organic electroluminescent device was fabricated by depositing ETH2 on the light-emitting layer to form a hole blocking layer with a thickness of 50 Å, depositing Alq3 on the hole blocking layer to form an electron transport layer with a thickness of 300 Å, depositing LiF on the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then vacuum depositing Al on the electron injection layer to form a second electrode with a thickness of 3000 Å.

[0484] In addition, a light-emitting device of Example 5 was fabricated using the same method as in Example 1, except that when forming the light-emitting layer, instead of vacuum depositing Compound 1 (First Compound), Compound ETH66 (Second Compound), and Compound HTH29 (Third Compound) on the hole transport layer, Compound 1 (First Compound), Compound ETH66 (Second Compound), and Compound HTH29 (Third Compound) were vacuum deposited. Here, the content of Compound 1 was 10 wt% per total weight (100 wt%) of the light-emitting layer, the content of Compound DFD1 was 0.5 wt% per total weight (100 wt%) of the light-emitting layer, and the weight ratio of Compound ETH66 to Compound HTH29 was adjusted to 3:7.

[0486] (Evaluation of light-emitting device characteristics)

[0487] Table 1 shows the evaluation results of the light-emitting devices for Example 1, Example 2, and the Comparative Example. Table 1 shows the fabricated light-emitting devices. 3 MLCT, 3 MC, the predicted value of the maximum emission wavelength (λmax), and the measured value of the maximum emission wavelength were presented. 3 MLCT (Metal to Ligand Charge Transfer) and 3 The results are presented by quantum simulating the MC (3 Metal Centered State) energy according to the B3LYP DFT calculation method.

[0488] device Dopant 3 MLCT max predicted value max measurement value 3 MC (%) (nm) (nm) (kcal / mol) Comparative example X1 8.8 468 471 0.21 Example 1 1 12.2 463 458 0.42 Example 2 36 12.3 464 457 0.41 Example 3 60 12.2 463 457 0.42 Example 4 97 12.6 444 456 0.45

[0489] Referring to the results in Table 1, the light-emitting devices of Examples 1 and 2 have higher light-emitting devices compared to the light-emitting device of the Comparative Example. 3 MLCT value, high 3 It can be confirmed that the maximum emission wavelength is short wavelength, based on the MC value.

[0490] The light-emitting elements of the examples are higher compared to the light-emitting elements of the comparative examples. 3 MLCT value, and 3 By having MC, it can have high luminous efficiency. In addition, the light-emitting elements of the example have a shorter maximum emission wavelength compared to the light-emitting elements of the comparative example, and can emit blue light of high purity.

[0492] 1000 cd / m of the light-emitting elements fabricated in Examples 1 to 5 above 2 Driving voltage (V), luminous efficiency (cd / A), color conversion efficiency (cd / A / y), maximum emission wavelength (nm), and lifetime (T 90 ) were measured using the Keithley MU 236 and PR650 luminance meter, respectively, and the results are shown in Tables 2 and 3, respectively. In Table 3, lifetime (T 90 ) is the time (hr) taken to reach 90% of the initial brightness.

[0493] No. dopant Host Delayed fluorescent dopant Luminance (cd / ㎡) Driving voltage (V) Luminous efficiency (cd / A) Compound 1 second compound Third compound Fourth compound Example 1 1 ETH66 HTH29 - 1000 4.8 54 Example 2 36 ETH66 HTH29 - 1000 4.8 51 Example 3 60 ETH66 HTH29 - 1000 4.9 53 Example 4 97 ETH66 HTH29 - 1000 4.9 54 Example 5 1 ETH66 HTH29 DFD1 1000 4.8 60 Comparative Example 1 X1 ETH66 HTH29 - 1000 5.0 22

[0494] Referring to Table 2, it can be seen that the light-emitting devices of Examples 1 to 5 have lower driving voltage and higher luminous efficiency compared to Comparative Example 1. Through this, it can be seen that when the first compound of the examples is included in the light-emitting layer, the driving voltage and luminous efficiency of the light-emitting device are improved. Specifically, it can be seen that the driving voltage and luminous efficiency are improved in both cases where the second and third compounds are included along with the first compound in the light-emitting layer, as in Examples 1 to 4, and in both cases where the second to fourth compounds are included along with the first compound in the light-emitting layer, as in Example 5.

[0495] No. dopant Host Delayed fluorescence dopant Color conversion efficiency (cd / A / y) Maximum emission wavelength (nm) Lifespan (T 90 )(hr) Compound 1 second compound Third compound Fourth compound Example 1 1 ETH66 HTH29 - 380 458 70 Example 2 36 ETH66 HTH29 - 360 457 71 Example 3 60 ETH66 HTH29 - 375 457 68 Example 4 97 ETH66 HTH29 - 380 456 63 Example 5 1 ETH66 HTH29 DFD1 498 457 97 Comparative Example 1 X1 ETH66 HTH29 - 160 471 53

[0496] Referring to Table 3, it can be seen that the light-emitting devices of Examples 1 to 5 exhibit higher color conversion efficiency, lower maximum emission wavelength, and longer lifespan characteristics compared to Comparative Example 1. Through this, it can be seen that when the first compound of the examples is included in the light-emitting layer, the color conversion efficiency, the color purity of blue light, and the lifespan of the device are improved. Specifically, it can be seen that the color conversion efficiency, the color purity of blue light, and the lifespan of the device are improved in both cases where the second and third compounds are included in the light-emitting layer along with the first compound, as in Examples 1 to 4, and where the second to fourth compounds are included in the light-emitting layer along with the first compound, as in Example 5.

[0497] The organometallic compound of one embodiment includes spirobiacridine, high 3 MLCT value, and high 3 It can have an MC value and a low maximum emission wavelength. A light-emitting device of one embodiment may include an organometallic compound of one embodiment in the light-emitting layer, and may have high luminous efficiency, high color purity, and long lifespan characteristics.

[0498] Although embodiments of the present invention have been described above, those skilled in the art will understand that the present invention may be implemented in other specific forms without changing its technical concept or essential features. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive. Explanation of the symbols

[0507] DD, DD-TD: Display device ED: Organic electroluminescent device EL1: First electrode EL2: Second electrode HTR: Hole transport region EML: Emissive layer ETR: Electron transport region

Claims

Claim 1 A light-emitting element comprising: a first electrode; a second electrode disposed on the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode and comprising a first compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, M is Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, or Os, and A1 to A3, and A 41 To A 44 are each independently a ring-forming hydrocarbon ring with 5 to 60 carbon atoms, or a heterocycle with 1 to 60 carbon atoms, b1 to b3 are each independently integers from 0 to 4, b41 to b44 are each independently integers from 0 to 3, and L1 to L3 are each independently direct linkage, *-O-*', *-S-*', *-C(R 11 )(R 12 )-*', *-C(R 13 )=*', *-C(R 14 )=C(R 15 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 16 )-*', *-N(R 17 )-*', *-P(R 18 )(R 19 )-*', *-Si(R 20 )(R 21 )-*', and *-Ge(R 22 )(R 23 Selected from )-*', and L4 is *-O-*', *-S-*', *-C(R 11 )(R 12 )-*', *-C(R 13 )=*', *-C(R 14 )=C(R 15 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 16 )-*', *-N(R 17 )-*', *-P(R 18 )(R 19 )-*', *-Si(R 20 )(R 21 )-*', and *-Ge(R 22 )(R 23 Selected from )-*', n1 and n3 are each independently integers from 0 to 3, n2 and n4 are each independently integers from 1 to 3, R1 to R3, and R 41 to R 44 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group with 3 to 30 carbon atoms, and R 11 to R 23 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms," " is a single bond or a double bond. Claim 2 In claim 1, the above chemical formula 1 is a light-emitting element represented by the following chemical formula 2: [Chemical Formula 2] In the above chemical formula 2, X1 and X2 are each independently CRa or N, and Ra is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, and A1 to A3, n1, n3, n4, L1, L 3, L4, b1 to b3, b41 to b44, R1 to R3, and R 41 to R 44 It is the same as defined in Chemical Formula 1 above. Claim 3 In paragraph 2, the above chemical formula 2 is a light-emitting element represented by the following chemical formula 3-1 or chemical formula 3-2: [Chemical formula 3-1] [Chemical Formula 3-2] In the above chemical formula 3-1 and the above chemical formula 3-2, A1 to A3, n1, n3, n4, L1, L3, L4, b1 to b3, b41 to b44, R1 to R3, and R 41 to R 44 It is the same as defined in Chemical Formula 1 above. Claim 4 In paragraph 3, the above chemical formula 3-1 is a light-emitting element represented by the following chemical formula 3A or chemical formula 3B: [Chemical formula 3A] [Chemical Formula 3B] In the above chemical formulas 3A and 3B, A1 to A3, n1, n3, L1, L3, b1 to b3, b41 to b44, R1 to R3, R 41 to R 44 , and R 17 It is the same as defined in Chemical Formula 1. Claim 5 In claim 4, R in the above chemical formula 3B 17 A light-emitting element having a substituted or unsubstituted phenyl group. Claim 6 In paragraph 3, R in the above chemical formula 3-2 43 and R 44 Each is a light-emitting device consisting of hydrogen atoms. Claim 7 In paragraph 2, the above chemical formula 2 is a light-emitting element represented by the following chemical formula 4: [Chemical Formula 4] In the above chemical formula 4, n4, L4, b2, b3, b41 to b44, R1 to R3, R 41 to R 44 , X1, and X2 are the same as defined in Chemical Formula 2. Claim 8 In paragraph 1, R1 to R3, and R 41 to R 44 A light-emitting element in which each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted t-butyl group, and a substituted or unsubstituted phenyl group. Claim 9 A light-emitting device according to claim 1, wherein the light-emitting layer further comprises a second compound and a third compound different from the first compound, and the first compound is a phosphorescent dopant, the second compound is a hole-transporting host, and the third compound is an electron-transporting host. Claim 10 In claim 9, the light-emitting layer further comprises the fourth compound, which is different from the first to third compounds, and the light-emitting element is a delayed fluorescence dopant. Claim 11 In claim 1, the light-emitting layer is a light-emitting element that emits blue light. Claim 12 In claim 1, the light-emitting layer comprises at least one of the compounds listed in the following compound group 1, a light-emitting element: [Compound group 1] . Claim 13 Organometallic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, M is Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, or Os, and A1 to A3, and A 41 To A 44 are each independently a ring-forming hydrocarbon ring having 5 to 60 carbon atoms, or a heterocycle having 1 to 60 carbon atoms, b1 to b3 are each independently integers from 0 to 4, b41 to b44 are each independently integers from 0 to 3, and L1 to L3 are each independently direct bonds, *-O-*', *-S-*', *-C(R 11 )(R 12 )-*', *-C(R 13 )=*', *-C(R 14 )=C(R 15 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 16 )-*', *-N(R 17 )-*', *-P(R 18 )(R 19 )-*', *-Si(R 20 )(R 21 )-*', and *-Ge(R 22 )(R 23 Selected from )-*', and L4 is *-O-*', *-S-*', *-C(R 11 )(R 12 )-*', *-C(R 13 )=*', *-C(R 14 )=C(R 15 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 16 )-*', *-N(R 17 )-*', *-P(R 18 )(R 19 )-*', *-Si(R 20 )(R 21 )-*', and *-Ge(R 22 )(R 23 Selected from )-*', n1 and n3 are each independently integers from 0 to 3, n2 and n4 are each independently integers from 1 to 3, R1 to R3, and R 41 to R 44 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group with 3 to 30 carbon atoms, and R 11 to R 23 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms," " is a single bond or a double bond. Claim 14 In claim 13, the above Chemical Formula 1 is an organometallic compound represented by the following Chemical Formula 2: [Chemical Formula 2] In the above chemical formula 2, X1 and X2 are each independently CRa or N, and Ra is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, and A1 to A3, n1, n3, n4, L1, L 3, L4, b1 to b3, b41 to b44, R1 to R3, and R 41 to R 44 It is the same as defined in Chemical Formula 1 above. Claim 15 In claim 14, the above Chemical Formula 2 is an organometallic compound represented by the following Chemical Formula 3-1 or Chemical Formula 3-2: [Chemical Formula 3-1] [Chemical Formula 3-2] In the above chemical formula 3-1 and the above chemical formula 3-2, A1 to A3, n1, n3, n4, L1, L3, L4, b1 to b3, b41 to b44, R1 to R3, and R 41 to R 44 It is the same as defined in Chemical Formula 1. Claim 16 In claim 15, the above formula 3-1 is an organometallic compound represented by the following formula 3A or formula 3B: [Formula 3A] [Chemical Formula 3B] In the above chemical formulas 3A and 3B, A1 to A3, n1, n3, L1, L3, b1 to b3, b41 to b44, R1 to R3, R 41 to R 44 , and R 17 It is the same as defined in Chemical Formula 1. Claim 17 In claim 16, R in the above chemical formula 3B 17 Organometallic compounds that are substituted or unsubstituted phenyl groups. Claim 18 In claim 15, R in the above chemical formula 3-2 43 and R 44 are organometallic compounds, each consisting of a hydrogen atom. Claim 19 In claim 14, the above chemical formula 2 is an organometallic compound represented by the following chemical formula 4: [Chemical Formula 4] In the above chemical formula 4, n4, L4, b2, b3, b41 to b44, R 2, R3, R 41 to R 44 , X1, and X2 are the same as defined in Chemical Formula 2. Claim 20 In claim 13, the above chemical formula 1 is an organometallic compound represented by any one of the compounds of compound group 1 below: [Compound group 1] .

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