Organic electroluminescent device and organic metal compound for organic electroluminescent device

Abstract

An organic electroluminescent device and an organic metal compound of the organic electroluminescent device are disclosed. The organic electroluminescent device of the embodiment includes a first electrode, a second electrode, and an emission layer between the first electrode and the second electrode, wherein the emission layer includes an organic metal compound represented by Formula 1, and the emission layer can exhibit high emission efficiency performance. Formula 1#imgabs0# wherein M, Y, Q 1 To Q 4 , L 1 To L 4 , b1 to b3, X 1 To X 3 , A 1 To A 4 , R 1 To R 8 And a1 to a8 are the same as defined in the specification.

Description

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0152479, filed on November 25, 2019, which is hereby incorporated by reference in its entirety. Technical Field

[0002] Embodiments of the present disclosure relate to an organic electroluminescent device and an organometallic compound used therein. Background Art

[0003] Recently, development of organic electroluminescent displays as image displays is being actively carried out. Unlike liquid crystal displays, organic electroluminescent displays are so-called self-luminescent displays in which holes and electrons injected from a first electrode and a second electrode, respectively, are recombined in an emission layer and a light-emitting material including an organic compound in the emission layer emits light to provide a display.

[0004] When organic electroluminescent devices are applied to displays, it is desired to reduce driving voltage and to improve emission efficiency and lifetime of the organic electroluminescent devices, and research is continuously being conducted on the development of materials for organic electroluminescent devices that stably achieve these characteristics.

[0005] In addition, in developing materials for an emission layer, organic metal compounds used as dopant materials have been continuously developed, but development of a dopant material showing high efficiency in a blue emission region is still desired. Summary of the invention

[0006] Embodiments of the present disclosure provide an organic metal compound exhibiting excellent emission efficiency and long life characteristics.

[0007] In addition, embodiments of the present disclosure also provide an organic electroluminescent device including an organic metal compound in an emission layer and having improved device characteristics.

[0008] An embodiment of the present disclosure provides an organometallic compound represented by the following Formula 1:

[0009] Formula 1

[0010]

[0011] In Formula 1, M is a transition metal, and Y is a direct bond, O, S, Se, SO 2 NR a , BR b , CR c R d or SiR e R f , Q 1 To Q4 are independently C or N. 1 To L 4 are independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms. At least one selected from b1 to b3 is 1, and the others are 0, wherein if b1 to b3 are all 1, then X 1 To X 3 Both are B. A 1 To A 4 R is independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms. 1 To R 8 and R a To R f are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and optionally, R 1 To R 8 and R a To R f Combines with an adjacent group to form a ring, and a1 to a8 are each independently an integer of 0 to 3.

[0012] In an embodiment, M may be Pt, Pd, Cu or Os.

[0013] In an embodiment, Formula 1 may be represented by any one selected from the following Formulas 1-1 to 1-3:

[0014] Formula 1-1

[0015]

[0016] Formula 1-2

[0017]

[0018] Formula 1-3

[0019]

[0020] In formula 1-1 to formula 1-3, M, Y, Q 1 To Q 4 , L 1 To L4 , A 1 To A 4 , R 1 To R 8 and a1 to a8 are the same as defined with respect to Formula 1.

[0021] In an embodiment, Formula 1 may be represented by the following Formula 2-A:

[0022] Formula 2-A

[0023]

[0024] In formula 2-A, Y, L 1 , Q 1 To Q 4 , b1 to b3, X 1 To X 3 , A 1 To A 4 , R 1 To R 8 and a1 to a8 are the same as defined with respect to Formula 1.

[0025] In the embodiment, L 1 It can be represented by the following formula La or formula Lb:

[0026] Formula La

[0027]

[0028] Formula Lb

[0029]

[0030] In formula La and formula Lb, Z 1 To Z 8 are each independently N, O, S, NR or CR, R is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and optionally, R combines with an adjacent group to form a ring, and Q 1 The same as defined with respect to Formula 1.

[0031] According to an embodiment of the present disclosure, there is provided an organometallic compound represented by the following formula A:

[0032] Formula A

[0033]

[0034] In formula A, M is a transition metal, Q 1 To Q 4 are independently C or N, L 1 To L 4 are independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms. 11 To Y 13 Any one of the above is NR a1 , BR b1 , CR c1 R d1 or SiR e1 R f1 , and the rest are independently direct bonds, O, S, Se, SO 2 NR a , BR b , CR c R d or SiR e R f , R a1 , R b1 , R c1 and R e1 is a substituted or unsubstituted condensed ring having three or more rings and containing at least one B as a ring-forming atom. 1 To R 4 , R a To R f , R d1 and R f1 are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and optionally, R 1 To R 4 , R a To R f , R d1 and R f1 Combines with an adjacent group to form a ring, and a1 to a4 are each independently an integer of 0 to 3.

[0035] In an embodiment, from R a1 , Rb1 , R c1 and R e1 At least one selected therefrom may be a substituted or unsubstituted condensed ring including an azaborane moiety.

[0036] In an embodiment, Formula A can be represented by any one selected from the following Formula A-1 to Formula A-3:

[0037] Formula A-1

[0038]

[0039] Formula A-2

[0040]

[0041] Formula A-3

[0042]

[0043] In Formula A-1 to Formula A-3, A 1 To A 4 R is independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms. 5 To R 8 are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and optionally, R 5 To R 8 Combined with adjacent groups to form a ring, a5 to a8 are independently integers of 0 to 3, and M, Y 11 , Y 13 , Q 1 To Q 4 , L 1 To L 4 , R 1 To R 4 and a1 to a4 are the same as defined with respect to formula A.

[0044] According to an embodiment of the present disclosure, an organic electroluminescent device is provided, which includes: a first electrode; a second electrode located on the first electrode; and an emission layer between the first electrode and the second electrode, wherein the emission layer includes any one of the above-mentioned organic metal compounds according to the embodiment.

[0045] In an embodiment, the emissive layer may emit phosphorescence.

[0046] In an embodiment, the emission layer may include a host and a dopant, and the dopant may include the above-described organic metal compound according to an embodiment. BRIEF DESCRIPTION OF THE DRAWINGS

[0047] The accompanying drawings are included to provide a further understanding of the subject matter of the present disclosure and are incorporated into and constitute a part of this specification. The accompanying drawings illustrate exemplary embodiments of the present disclosure and together with the description serve to explain the principles of the subject matter of the present disclosure. In the drawings:

[0048] Figure 1 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present disclosure;

[0049] Figure 2 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present disclosure;

[0050] Figure 3 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present disclosure; and

[0051] Figure 4 is a cross-sectional view schematically showing an organic electroluminescent device according to an embodiment of the present disclosure. DETAILED DESCRIPTION

[0052] The subject matter of the present disclosure may have various modifications and may be implemented in different forms, and the exemplary embodiments will be described in more detail with reference to the accompanying drawings. However, the subject matter of the present disclosure may be implemented in different forms and should not be interpreted as being limited to the embodiments set forth herein. On the contrary, the present disclosure encompasses all modifications, equivalents, and substitutions included within the spirit and technical scope of the appended claims and their equivalents.

[0053] It will be understood that when an element (or region, layer, portion, etc.) is referred to as being “on,” “connected to” or “coupled to” another element, it can be directly on, directly connected to or directly coupled to the other element, or a third intervening element may be present.

[0054] The same reference numerals always represent the same elements. In addition, in the drawings, in order to effectively explain the technical contents, the thickness, ratio and size of the constituent elements are exaggerated.

[0055] The term "and / or" includes one or more combinations that can be defined by the relevant elements.

[0056] It will be understood that, although the terms first, second, etc. can be used to describe various elements herein, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Therefore, without departing from the spirit and scope of the present disclosure, the first element can be referred to as the second element. Similarly, the second element can be referred to as the first element. As used herein, unless the context clearly indicates otherwise, the singular form is also intended to include the plural form.

[0057] In addition, the terms “below,” “under,” “on,” and “over” are used to explain the relationship of elements shown in the drawings. These terms are relative concepts and are explained based on the directions shown in the drawings.

[0058] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by those of ordinary skill in the art to which the present disclosure belongs. It will also be understood that terms (such as those defined in common dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant art, and will not be interpreted in an idealized or overly formal sense, unless explicitly defined as such herein.

[0059] It will also be understood that when the term "comprises" and / or its variations are used in this specification, it indicates the presence of the stated features, numbers, steps, operations, elements, parts or combinations thereof, but does not exclude the presence or addition of one or more other features, numbers, steps, operations, elements, parts or combinations thereof.

[0060] Hereinafter, an organic electroluminescent device according to an embodiment of the present disclosure and a compound of the embodiment included therein will be described with reference to the accompanying drawings.

[0061] Figures 1 to 4 is a cross-sectional view schematically showing an organic electroluminescent device according to an exemplary embodiment of the present disclosure. Figures 1 to 4 , in the organic electroluminescent device 10 of the embodiment, the first electrode EL1 and the second electrode EL2 face each other, and the emission layer EML may be located between the first electrode EL1 and the second electrode EL2.

[0062] In addition, in addition to the emission layer EML, the organic electroluminescent device 10 of the embodiment further includes a plurality of functional layers between the first electrode EL1 and the second electrode EL2. The plurality of functional layers may include a hole transport region HTR and an electron transport region ETR. For example, the organic electroluminescent device 10 according to the embodiment may include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 stacked in sequence. In addition, the organic electroluminescent device 10 of the embodiment may include a cap layer CPL on the second electrode EL2.

[0063] The organic electroluminescent device 10 of the embodiment may include an organic metal compound of the embodiment, which will be further described below, in the emission layer EML between the first electrode EL1 and the second electrode EL2 .

[0064] When with Figure 1 When compared, Figure 2 1 shows a cross-sectional view of an organic electroluminescent device 10 of an embodiment, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 1 When compared, Figure 3 The cross-sectional view of the organic electroluminescent device 10 of the embodiment is shown, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL and a hole blocking layer HBL. Figure 2 When compared, Figure 4 A cross-sectional view of an organic electroluminescent device 10 including an embodiment of a cap layer CPL on the second electrode EL2 is shown.

[0065] The first electrode EL1 has conductivity (e.g., electrical conductivity). The first electrode EL1 may be formed using a metal alloy and / or a conductive compound. The first electrode EL1 may be an anode. In addition, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. If the first electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide (such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and indium tin zinc oxide (ITZO)). If the first electrode EL1 is a transflective 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, LiF / Al, Mo, Ti, a compound thereof, or a mixture thereof (e.g., a mixture of Ag and Mg). In addition, the first electrode EL1 may have a structure including a plurality of layers, the plurality of layers including a reflective layer or a transflective layer formed using the above-mentioned materials and a transparent conductive layer formed using ITO, IZO, ZnO, or ITZO. For example, the first electrode EL1 may include a three-layer structure of ITO / Ag / ITO. However, the embodiments of the present disclosure are not limited thereto. The thickness of the first electrode EL1 may be from about 100 to about 500 mm. To about For example, from about To about

[0066] The hole transport region HTR is disposed 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 hole buffer layer, and an electron blocking layer EBL. The thickness of the hole transport region HTR may be from about 100 to about 500 Å. To about

[0067] The hole transport region HTR may have a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multi-layer structure including a plurality of layers formed using a plurality of different materials.

[0068] For example, the hole transport region HTR may have a structure of a single layer of the hole injection layer HIL or the hole transport layer HTL, or may have a structure of a single layer formed using a hole injection material and a hole transport material. In some embodiments, the hole transport region HTR may have a structure of a single layer formed using a plurality of different materials, or a structure of a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / hole buffer layer, a hole injection layer HIL / hole buffer layer, a hole transport layer HTL / hole buffer layer, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL stacked from the first electrode EL1 without limitation.

[0069] The hole transport region HTR may be formed using various suitable methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and / or a laser induced thermal imaging (LITI) method.

[0070] The hole injection layer HIL may include, for example, a phthalocyanine compound (such as copper phthalocyanine), N,N'-diphenyl-N,N'-bis[4-(di-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), 4,4',4"-[tri(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tri(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tri{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) The results showed that the polyaniline / poly(4-styrene sulfonate) (PANI / PSS) was prepared by mixing polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate], and dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

[0071] The hole transport layer HTL may include, for example, carbazole derivatives (such as N-phenylcarbazole and polyvinylcarbazole), fluorene derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives (such as 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA)), N,N'-di(1-naphthyl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), and the like.

[0072] The thickness of the hole transport region HTR may be from about To about For example, from about To about The thickness of the hole injection layer HIL may be, for example, from about To about The thickness of the hole transport layer HTL may be from about To about For example, the thickness of the electron blocking layer EBL may be from about To about If the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above ranges, appropriate or satisfactory hole transport properties may be achieved without significantly increasing driving voltage.

[0073] In addition to the above materials, the hole transport region HTR may also include a charge generating material to improve conductivity (e.g., electrical conductivity). The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano-containing compound without limitation. For example, non-limiting examples of p-dopants may include quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), metal oxides such as tungsten oxide and molybdenum oxide, and inorganic metal compounds such as CuI and RbI, without limitation.

[0074] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a hole buffer layer and an electron blocking layer EBL. The hole buffer layer may compensate for the optical resonance distance according to the wavelength of light emitted from the emission layer EML, thereby improving the luminous efficiency. The material that may be included in the hole transport region HTR may be used as the material included in the hole buffer layer. The electron blocking layer EBL is a layer that prevents or reduces electrons from being injected from the electron transport region ETR to the hole transport region HTR.

[0075] The emission layer EML is disposed on the hole transport region HTR. The emission layer EML may have, for example, approximately To about or approximately To about The emission layer EML may have a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multilayer structure having a plurality of layers formed using a plurality of different materials.

[0076] In the organic electroluminescent device 10 of the embodiment, the emission layer EML may include the organic metal compound of the embodiment, which will be further described below.

[0077] In addition, in the specification, the term "substituted or unsubstituted" corresponds to being unsubstituted or substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group (or referred to as "oxy-containing group"), a sulfenyl group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, an alkyloxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. In addition, each exemplary substituent may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or a phenyl group substituted with a phenyl group.

[0078] In the specification, the term "forming a ring by combining with an adjacent group" may mean forming a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by combining with an adjacent group. The hydrocarbon ring includes an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring. The heterocycle includes an aliphatic heterocycle and an aromatic heterocycle. The ring formed by combining with an adjacent group may be a monocyclic ring or a polycyclic ring. In addition, the ring formed by combining with an adjacent group may be combined with another ring to form a spiro structure.

[0079] In the specification, the term "adjacent group" may refer to a substituent that replaces an atom directly bonded to an atom substituted by a corresponding substituent, another substituent that replaces an atom substituted by a corresponding substituent, or a substituent that is spatially located closest to the corresponding substituent. For example, in 1,2-xylene, two methyl groups may be interpreted as "adjacent groups" to each other, and in 1,1-diethylcyclopentane, two ethyl groups may be interpreted as "adjacent groups" to each other.

[0080] In the specification, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0081] In the specification, the alkyl group may be a linear type, a branched type, or a cyclic type (for example, a linear alkyl group, a branched alkyl group, or a cyclic alkyl group). The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-Hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl and the like without limitation.

[0082] In the specification, alkenyl refers to a hydrocarbon group including one or more carbon double bonds in the middle or at the end of an alkyl group of 2 or more carbon atoms. The alkenyl group can be straight chain or branched. The carbon number is not particularly limited, but can be 2 to 30, 2 to 20 or 2 to 10. Examples of alkenyl groups can include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, styrylvinyl, etc., without limitation.

[0083] In the specification, alkynyl refers to a hydrocarbon group including one or more carbon triple bonds in the middle or at the end of an alkyl group of 2 or more carbon atoms. The alkynyl group can be straight chain or branched. The carbon number is not particularly limited, but can be 2 to 30, 2 to 20 or 2 to 10. Examples of alkynyl groups can include ethynyl, propynyl, etc., without limitation.

[0084] In the specification, the hydrocarbon ring group can be an optional (optional, or optional) functional group or substituent derived from an aliphatic hydrocarbon ring or an optional functional group or substituent derived from an aromatic hydrocarbon ring. The carbon number of the hydrocarbon ring group for forming a ring can be 5 to 60, 5 to 30 or 5 to 20.

[0085] In the specification, aryl refers to an optional 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 carbon atoms in the aryl group used to form the ring may be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Base, etc., without restriction.

[0086] In the specification, heterocyclic group refers to an optional functional group or substituent derived from a ring including one or more heteroatoms selected from B, O, N, P, Si and S. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups can be heteroaryl groups. Aliphatic heterocyclic groups and aromatic heterocyclic groups can be monocyclic groups or polycyclic groups.

[0087] In the specification, the heterocyclic group may include one or more selected from B, O, N, P, Si and S as a heteroatom. If the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and has the concept of including a heteroaryl group. The carbon number of the heterocyclic group for forming a ring may be 2 to 30, 2 to 20 or 2 to 10.

[0088] In the specification, the aliphatic heterocyclic group may include one or more selected from B, O, N, P, Si and S as a hetero atom. The carbon number of the aliphatic heterocyclic group for forming a ring may be 2 to 30, 2 to 20 or 2 to 10. Examples of the aliphatic heterocyclic group include oxirane group, thiirane group, pyrrolidinyl group, piperidinyl group, tetrahydrofuranyl group, tetrahydrothienyl group, thianyl group, tetrahydropyranyl group, 1,4-dioxanyl group and the like without limitation.

[0089] In the specification, the heteroaryl group may include one or more selected from B, O, N, P, Si and S as a heteroatom. If the heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The carbon number of the heteroaryl group for forming a ring may be 2 to 30, 2 to 20 or 2 to 10. Examples of heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuranyl, and the like without limitation.

[0090] In the specification, silyl includes alkylsilyl and arylsilyl. Examples of silyl may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., without limitation.

[0091] In the specification, the carbon number of the amine group (or amino group) is not particularly limited, but can be 1 to 30. The amine group can include an alkylamine group, an arylamine group or a heteroarylamine group. Examples of the amine group include methylamine group, dimethylamine group, phenylamine group, diphenylamine group, naphthylamine group, 9-methyl-anthrylamine group, etc., without limitation.

[0092] In the specification, the thio group may include an alkylthio group and an arylthio group.

[0093] In the specification, the oxy group may include an alkyloxy group and an aryloxy group. The alkyloxy group may be a straight chain, a branched chain or a cyclic chain. The carbon number of the alkyloxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of oxy groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc. However, embodiments of the present disclosure are not limited thereto.

[0094] In the specification, the alkyl group in the alkylthio group, the alkylsulfonyl group, the alkylaryl group, the alkylamino group, the alkylboryl group and the alkylsilyl group is the same as the above-mentioned examples of the alkyl group.

[0095] In the specification, the aryl group in the aryloxy group, the arylthio group, the arylsulfonyl group, the arylamino group, the arylboryl group, the arylsilyl group, the arylselenyl group, and the arylalkyl group is the same as the above-mentioned examples of the aryl group.

[0096] In the specification, a direct key may refer to a single key.

[0097] In addition, in the manual, or Indicates the location of the connection.

[0098] In addition, in the manual, Indicates selective bonding to adjacent atoms or substituents. For example, It may be connected to the adjacent part via a single bond, or may be a part that does not form a bond.

[0099] The organic metal compound according to the embodiment may be represented by the following Formula 1:

[0100] Formula 1

[0101]

[0102] In Formula 1, M is a central metal atom, and M is a transition metal. In Formula 1, Y is a direct bond, O, S, Se, SO 2 NR a , BR b , CR c R d or SiR e R f .

[0103] In formula 1, Q 1 To Q 4 are independently C or N. In addition, L 1 To L 4 Each is independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms.

[0104] In Formula 1, at least one selected from b1 to b3 is 1 (for example, b1 to b3 are independently 0 or 1, and at least one selected from b1 to b3 is 1), and the rest are 0, wherein if b1 to b3 are all 1, then X 1 To X 3 For example, when any of b1 to b3 is 1, X 1 To X 3 The corresponding one in is B.

[0105] A 1 To A 4Each is independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms.

[0106] R 1 To R 8 and R a To R f are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and optionally, R 1 To R 8 and R a To R f Combines with adjacent groups to form a ring.

[0107] In Formula 1, a1 to a8 are each independently an integer of 0 to 3. In addition, if a1 to a8 are integers of 2 or more, then the plurality of R 1 To R 8 can be independently the same, or at least one of them can be different. For example, if a1 is an integer of 2 or greater, then multiple R 1 The groups may be the same, or at least one R 1 Can be combined with other R 1 If a1 is an integer of 2 or more, then the multiple R 1 The groups may be combined with each other to form a ring. 1 The description of the groups can be applied in the same way to R 2 To R 8 .

[0108] Furthermore, if a1 to a8 are all independently 0, then L 1 To L 4 and A 1 To A 4 Each may independently be an unsubstituted aryl group or an unsubstituted heteroaryl group.

[0109] R 1 To R 8 and R a To R f Each of R may be combined with an adjacent hydrocarbon ring or an adjacent heterocyclic ring to form a condensed ring. 1 To R 8 and R a To Rf Each may independently combine with an adjacent substituent to form a ring.

[0110] For example, the ring formed by combining with the adjacent group and the ring formed by combining with the adjacent substituent may be a hydrocarbon ring of 5 to 30 ring carbon atoms or a heterocyclic ring of 2 to 30 ring carbon atoms.

[0111] The organometallic compound of the embodiment represented by Formula 1 may have a bonding structure of a metal complex part including a central metal atom M and a condensed ring group containing boron (B).

[0112] In Formula 1, the metal complex moiety may be represented by the following Formula 1A, and the condensed ring group containing boron (B) may be represented by the following Formula 1B. In addition, the condensed ring group represented by Formula 1B may include at least one B atom as a ring-forming atom. For example, the condensed ring group represented by Formula 1B includes a B atom and may be a condensed ring group obtained by condensing three or more rings.

[0113]

[0114] The organometallic compound of the embodiment has a combination structure of a metal complex and a condensed ring group containing B, and can exhibit a high metal-ligand charge transfer (MLCT) ratio in one compound. Therefore, the organometallic compound of the embodiment exhibits a high MLCT ratio, and if used as a material for an emission layer, it can help improve the efficiency of an organic electroluminescent device. In addition, the MLCT ratio described in the specification refers to the triplet metal-ligand charge transfer ( 3 The MLCT) ratio is a relative ratio based on the case where 100% charge transfer occurs from the metal atom to the ligand.

[0115] The organic metal compound represented by Formula 1 has a bonding structure of a metal complex and a condensed ring group including B, and exhibits improved efficiency properties if used as a material of an emission layer. In addition, due to the structure of Formula 1B, blue-shifted light may be emitted.

[0116] In Formula 1, M may be a tetracoordinate metal atom that can bind to a ligand. M may be a metal atom such as platinum (Pt), palladium (Pd), copper (Cu), and osmium (Os), for example, M may be Pt.

[0117] In Formula 1, at least one selected from b1 to b3 may be 1, and the rest may be 0. For example, any one selected from b1 to b3 may be 1, and the rest may be 0. If any one selected from b1 to b3 is 1, then 1 To X 3 Any corresponding one selected from among them can correspond to B.

[0118] Formula 1 can be represented by any one selected from the following Formulas 1-1 to 1-3. Formula 1-1 corresponds to Formula 1 in which b1 is 1 and b2 and b3 are both 0, Formula 1-2 corresponds to Formula 1 in which b2 is 1 and b1 and b3 are both 0, and Formula 1-3 corresponds to Formula 1 in which b3 is 1 and b1 and b2 are both 0.

[0119] Formula 1-1

[0120]

[0121] Formula 1-2

[0122]

[0123] Formula 1-3

[0124]

[0125] In Formula 1-1 to Formula 1-3, the organometallic compound according to an embodiment may include an azaborane moiety.

[0126] In addition, in Formula 1-1 to Formula 1-3, the following formulas can be used to refer to Formula 1 for M, Y, and Q: 1 To Q 4 , L 1 To L 4 , A 1 To A 4 , R 1 To R 8 And the same explanation for a1 to a8.

[0127] In formula 1, Q 1 To Q 4 are independently C or N. In addition, L 1 To L 4 and A 1 To A 4 Each is independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms.

[0128] For example, L 1 To L 4 and A 1 To A 4 and L may be independently a substituted or unsubstituted aromatic ring of 5 to 10 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 10 ring carbon atoms including N, O or S as a heteroatom. 2 To L 4Each may independently be a substituted or unsubstituted benzene ring or a substituted or unsubstituted pyridine ring.

[0129] In formula 1, L 1 It can be represented by the following formula La or formula Lb:

[0130] Formula La

[0131]

[0132] Formula Lb

[0133]

[0134] In formula La and formula Lb, Q 1 is C or N. In addition, in formula La and formula Lb, It is the part that is bonded to M which is a metal atom. Yes and L 2 Combined parts.

[0135] In formula La and formula Lb, Z 1 To Z 8 Each is independently N, O, S, NR or CR, R is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and optionally, R may combine with an adjacent group to form a ring.

[0136] L 1 It may be represented by any one of the groups selected from the following group L:

[0137] Group L

[0138]

[0139]

[0140]

[0141] In the groups described in group group L, the same explanations on R with reference to formula La and formula Lb can be applied.

[0142] In addition, Formula 1 may be represented by the following Formula 2. Formula 2 corresponds to an organic metal compound in which the central metal atom M is Pt.

[0143] Formula 2

[0144]

[0145] In addition, the organometallic compound of the embodiment can be represented by the following formula 2-A:

[0146] Formula 2-A

[0147]

[0148] In Formula 2 and Formula 2-A, the formula for Y and L in Formula 1 can be applied. 1 To L 4 , Q 1 To Q 4 、b 1 To b 3 , X 1 To X 3 , A 1 To A 4 , R 1 To R 8 And the same explanation for a1 to a8.

[0149] In addition, the organometallic compound of the embodiment can be represented by the following formula A:

[0150] Formula A

[0151]

[0152] In formula A, M is a transition metal, Q 1 To Q 4 are independently C or N, L 1 To L 4 Each is independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms.

[0153] In addition, from Y 11 To Y 13 At least one of the selected a1 , BR b1 , CR c1 R d1 or SiR e1 R f1 , and the rest are independently direct bonds, O, S, Se, SO 2 NR a , BR b , CR c R d or SiR e R f , Ra1 , R b1 , R c1 and R e1 is a substituted or unsubstituted condensed ring having three or more rings and containing at least one B as a ring-forming atom. a1 , R b1 , R c1 and R e1 An azaborane moiety may be included.

[0154] R 1 To R 4 , R a To R f , R d1 and R f1 are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and optionally, R 1 To R 4 , R a To R f , R d1 and R f1 Combines with an adjacent group to form a ring, and a1 to a4 are each independently an integer of 0 to 3.

[0155] In the organometallic compound of the embodiment represented by formula A, with respect to M, Q 1 To Q 4 , R 1 To R 4 As well as a1 to a4, the same explanation as for the organometallic compound represented by Formula 1 can be applied.

[0156] In the organometallic compound according to the embodiment represented by Formula A, Y of the ligand compound bonded to M which is a metal atom 11 To Y 13 Corresponds to a linking group that connects adjacent rings to each other. In the organometallic compound of the embodiment, Y 11 To Y 13 At least one selected therefrom may be substituted with a condensed ring group including boron (B) as a ring atom. 11 To Y 13At least one bonded condensed ring group in the linking group includes at least one B as a ring-constituting atom, and may be a condensed ring group obtained by condensing three or more rings.

[0157] For example, in Formula A, Y 11 and Y 13 Can be directly connected, O, S, Se, SO 2 NR a , BR b , CR c R d or SiR e R f In addition, Y 12 Can be NR a1 , BR b1 , CR c1 R d1 or SiR e1 R f1 In some embodiments, Y 12 may be a portion substituted by a condensed ring group containing B. However, embodiments of the present disclosure are not limited thereto, and in Formula A, the portion substituted by a condensed ring group containing B may be Y 11 or Y 13 In addition, in formula A, the part substituted by the condensed ring group containing B may be selected from Y 11 , Y 12 and Y 13 Two of them.

[0158] In some embodiments, in Formula A, Y 11 Can be O or NR a , Y 13 Can be a direct key, Y 12 Can be NR a1 . R a It may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. a Can be connected with adjacent L 2 Substituent R 2 Combined to form a substituted or unsubstituted heterocyclic ring of 2 to 20 ring carbon atoms.

[0159] In addition, in formula A, R a1It may be a condensed ring group of three or more rings including B as a ring-constituting atom.

[0160] Formula A can be represented by any one selected from the following Formula A-1 to Formula A-3:

[0161] Formula A-1

[0162]

[0163] Formula A-2

[0164]

[0165] Formula A-3

[0166]

[0167] In Formula A-1 to Formula A-3, A 1 To A 4 are independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms, R 5 To R 8 are independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and optionally, R 5 To R 8 Combines with the adjacent group to form a ring. In addition, a5 to a8 are each independently an integer of 0 to 3.

[0168] In addition, regarding A 1 To A 4 , R 5 To R 8 and a5 to a8, the same explanation with reference to the embodiment of the organometallic compound represented by Formula 1 can be applied.

[0169] In Formula A-1 to Formula A-3, M and Y 11 , Y 13 , Q 1 To Q 4 , L 1 To L 4 , R 1 To R 4 and a1 to a4, the same explanations with reference to Formula A can be applied.

[0170] The organometallic compound of the embodiment represented by Formula 1 or Formula A may be a light-emitting dopant that emits blue light. In addition, the organometallic compound of the embodiment represented by Formula 1 or Formula A may be a phosphorescent dopant.

[0171] In an embodiment, the organic metal compound represented by Formula 1 or Formula A may be represented by any one selected from among the compounds represented in the following Compound Group 1. The emission layer EML may include at least one selected from among the compounds represented in the following Compound Group 1.

[0172] Compound Group 1

[0173]

[0174] In the specific compounds shown in Compound Group 1, "D" corresponds to a deuterium atom.

[0175] In the organic electroluminescent device 10 of the embodiment, the emission layer EML includes the organic metal compound according to the embodiment having a metal complex and a condensed ring group containing boron (B) as a ring-forming atom, and can exhibit improved emission efficiency properties. The organic metal compound according to the embodiment has a hybrid structure in which the metal complex is combined with the condensed ring group containing B, and the organic metal compound according to the embodiment can exhibit higher emission efficiency than that not including the condensed ring group containing B. 3 MLCT ratio.

[0176] In addition, in Figures 1 to 4 In the organic electroluminescent device 10 of the embodiment shown in , the emission layer EML may include a host and a dopant, and the emission layer EML may include an organic metal compound represented by Formula 1 or Formula A as a dopant material.

[0177] In an embodiment, the emission layer EML may emit phosphorescence. For example, the organic metal compound according to an embodiment represented by Formula 1 or Formula A may be a phosphorescent dopant.

[0178] In addition, in addition to the organic metal compound of the embodiment, the emission layer EML may also include a host material. In the organic electroluminescent device 10 of the embodiment, the emission layer EML may include any suitable material commonly used in the art as the host material without limitation. For example, it may include at least one selected from bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 1,3-bis(carbazole-9-yl)benzene (mCP), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF), 4,4',4"-tri(carbazole-9-yl)-triphenylamine (TCTA) and 1,3,5-tri(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene (TPBi). However, the embodiments of the present disclosure are not limited thereto. For example, tris(8-hydroxyquinoline)aluminum (Alq 3 )、4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4"-tri(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tri(N-phenylbenzimidazol-2-yl)benzene (TPBi), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyrylarylene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH 2 ), hexaphenylcyclotrisiloxane (DPSiO 3 ), octaphenylcyclotetrasiloxane (DPSiO 4 ), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF), bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide (POPCPA), etc. can be used as the main materials.

[0179] In addition, the emission layer EML of the organic electroluminescent device 10 of the embodiment may include any suitable dopant material generally available in the art in addition to the organometallic compound. For example, the emission layer EML may also include any suitable fluorescent dopant material generally available in the art, any suitable delayed fluorescent dopant material generally available in the art, and / or any suitable phosphorescent dopant material generally available in the art.

[0180] In some embodiments, the organic electroluminescent device 10 of the embodiment may include multiple emission layers. Multiple emission layers may be provided by stacking layers in sequence. For example, the organic electroluminescent device 10 including multiple emission layers may emit white light. The organic electroluminescent device 10 including multiple emission layers may be an organic electroluminescent device of a tandem structure. In the case where the organic electroluminescent device 10 includes multiple emission layers, at least one emission layer may include the organic metal compound of the above-mentioned embodiment.

[0181] exist Figures 1 to 4 In the organic electroluminescent device 10 of the embodiment shown in FIG, the electron transport region ETR is disposed on the emission layer EML. The electron transport region ETR may include at least one selected from the hole blocking layer HBL, the electron transport layer ETL, and the electron injection layer EIL. However, the embodiments of the present disclosure are not limited thereto.

[0182] The electron transport region ETR may have a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multilayer structure having a plurality of layers formed using a plurality of different materials.

[0183] 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 formed using an electron injection material and an electron transport material. In addition, the electron transport region ETR may have a single-layer structure including a plurality of different materials, or may have a structure of an electron transport layer ETL / electron injection layer EIL or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL stacked from an emission layer EML without limitation. The thickness of the electron transport region ETR may be, for example, from about 1000 Å to about 5000 Å. To about

[0184] The electron transport region ETR may be formed using various methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and / or a laser induced thermal imaging (LITI) method.

[0185] If the electron transport region ETR includes an electron transport layer ETL, the electron transport region ETR may include an anthracene-based compound. The electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq 3), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bp hen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), or a mixture thereof without limitation. The thickness of the electron transport layer ETL may be from about To about and can be, for example, from about To about If the thickness of the electron transport layer ETL satisfies the above range, appropriate or satisfactory electron transport properties may be obtained without significantly increasing driving voltage.

[0186] If the electron transport region ETR includes an electron injection layer EIL, the electron transport region ETR may include a metal halide (such as LiF, NaCl, CsF, RbCl, RbI, and / or CuI), a lanthanide metal (such as Yb), a metal oxide (such as Li 2 O and / or BaO) and / or lithium hydroxyquinoline (LiQ). However, the embodiments of the present disclosure are not limited thereto. The electron injection layer EIL can also be formed using a mixed material of an electron transport material and an insulating organic metal salt. The organic metal salt can be a material having an energy band gap of about 4 eV or more. For example, the organic metal salt can include, for example, metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate and / or metal stearate. The thickness of the electron injection layer EIL can be from about 100 to about 200 Å. To about And from about To about If the thickness of the electron injection layer EIL satisfies the above range, appropriate or satisfactory electron injection properties may be obtained without causing a significant increase in driving voltage.

[0187] As described above, the electron transport region ETR may include a hole blocking layer HBL. The hole blocking layer HBL may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl-1,10-phenanthroline (Bphen). However, embodiments of the present disclosure are not limited thereto.

[0188] The second electrode EL2 is disposed on the electron transport region ETR. The second electrode EL2 may be a common electrode or a cathode. The second electrode EL2 may be a transmissive electrode, a transflective electrode or a reflective electrode. If the second electrode EL2 is a transmissive electrode, the second electrode EL2 may include a transparent metal oxide, for example, ITO, IZO, ZnO, ITZO, etc.

[0189] If the second electrode EL2 is a transflective 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, a compound thereof, or a mixture thereof (e.g., a mixture of Ag and Mg). The second electrode EL2 may have a multilayer structure including a reflective layer or a transflective layer formed using the above materials and a transparent conductive layer formed using ITO, IZO, ZnO, ITZO, or the like.

[0190] In some embodiments, the second electrode EL2 may be connected to the auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0191] Reference Figure 4 On the second electrode EL2 of the organic electroluminescent device 10 of the embodiment, a capping layer CPL may be further included. The capping layer CPL may include, for example, α-NPD, NPB, TPD, m-MTDATA, Alq 3 , CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), etc.

[0192] As described above, the organic electroluminescent device 10 according to an embodiment of the present disclosure includes an organic metal compound substituted with a condensed ring group including boron (B) as a ring-forming atom in the emission layer EML and may exhibit excellent emission efficiency properties.

[0193] Hereinafter, the compounds according to the embodiments of the present disclosure and the organic electroluminescent devices of the embodiments will be specifically described with reference to Examples and Comparative Examples. The following examples are merely illustrative to help understand the subject matter of the present disclosure, and the scope of the present disclosure is not limited thereto.

[0194] Example

[0195] 1. Synthesis of organometallic compounds

[0196] The organometallic compound according to an embodiment of the present disclosure may be prepared, for example, as follows. However, the synthesis method of the organometallic compound according to an embodiment of the present disclosure is not limited thereto.

[0197] (1) Synthesis of organometallic compound 1

[0198] The organometallic compound 1 according to the embodiment can be synthesized by the steps set forth in the following reaction 1:

[0199] Reaction 1

[0200]

[0201]

[0202] Synthesis of Intermediate 1-A

[0203] 1,3,5-tribromobenzene (1 eq), diphenylamine (2.5 eq), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 ) (0.02eq) and NaOt-Bu (3eq) were suspended in dioxane (0.1M), and the temperature was then raised to about 100°C and stirred for about 12 hours to form a reaction mixture. The reaction mixture was extracted with dichloromethane and distilled water. The organic layer was washed 3 times with distilled water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to form a concentrated solution. The concentrated solution was separated by column chromatography to obtain Intermediate 1-A with a yield of 70%.

[0204] Synthesis of intermediate 1-B

[0205] Intermediate 1-A (1 eq), 2-aminopyridine (1.2 eq), tris(dibenzylideneacetone)dipalladium (0.02 eq) and NaOt-Bu (1.5 eq) were suspended in dioxane (0.1 M), and the temperature was then raised to about 100° C. and stirred for about 12 hours to form a reaction mixture. The reaction mixture was extracted with dichloromethane and distilled water. The organic layer was washed 3 times with distilled water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to form a concentrated solution. The concentrated solution was separated by column chromatography to obtain intermediate 1-B with a yield of 80%.

[0206] Synthesis of intermediate 1-C

[0207] Intermediate 1-B (1 eq), 1-bromo-3-methoxybenzene (1.2 eq), tris(dibenzylideneacetone)dipalladium (0.02 eq) and NaOt-Bu (1.5 eq) were suspended in dioxane (0.1 M), and the temperature was then raised to about 100° C. and stirred for about 12 hours to form a reaction mixture. The reaction mixture was extracted with dichloromethane and distilled water. The organic layer was washed 3 times with distilled water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to form a concentrated solution. The concentrated solution was separated by column chromatography to obtain intermediate 1-C with a yield of 75%.

[0208] Synthesis of intermediate 1-D

[0209] Intermediate 1-C was suspended using HBr (0.5M) and acetic acid (0.5M), and the temperature was then raised to about 120°C and stirred for about 12 hours to form a reaction mixture. The reaction mixture was neutralized with an aqueous solution of 0.3M NaOH, and the resulting solid was filtered. The filtered solid was extracted with dichloromethane and distilled water. The organic layer was washed 3 times with distilled water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to form a concentrated solution. The concentrated solution was separated by column chromatography to obtain an intermediate 1-D with a yield of 75%.

[0210] Synthesis of intermediate 1-E

[0211] Intermediate 1-D (1.0 eq), 1-(3-bromophenyl)-1H-imidazole (1.0 eq), copper iodide (0.1 eq), potassium phosphate (2.0 eq) and L-proline (0.1 eq) were suspended in 100 mL of dimethylformamide, and the temperature was then raised to about 120° C. and stirred for about 12 hours to form a reaction mixture. The reaction mixture was extracted with dichloromethane and distilled water. The organic layer was washed 3 times with distilled water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to form a concentrated solution. The concentrated solution was separated by column chromatography to obtain Intermediate 1-E with a yield of 70%.

[0212] Synthesis of Intermediate 1-F

[0213] Intermediate 1-E was dissolved in acetone, and iodomethane (2 eq) was added thereto, followed by stirring at room temperature for about 24 hours. After the reaction was completed, the solvent was removed under reduced pressure to form a concentrated solution, and the concentrated solution was separated by column chromatography to obtain Intermediate 1-F with a yield of 80%.

[0214] Synthesis of intermediate 1-G

[0215] Intermediate 1-F was dissolved in a mixed solvent of methanol and distilled water in a volume ratio of 4:1, and ammonium hexafluorophosphate (2 eq) was added thereto. The resulting solid was stirred at room temperature for about 12 hours. The solid was filtered and washed with distilled water and diethyl ether to obtain intermediate 1-G with a yield of 90%.

[0216] Synthesis of intermediate 1-H

[0217] Intermediate 1-G (1.0 eq), sodium acetate (3.0 eq) and dichloro(1,5-cyclooctadiene)platinum (II) (1.1 eq) were suspended in 1,4-dioxane solvent. The temperature of the reaction mixture was raised to about 120° C. and stirred for about 12 hours. After the reaction was completed, the solvent was removed under reduced pressure to form a concentrated solution. The concentrated solution was separated by column chromatography to obtain an intermediate 1-H with a yield of 40%.

[0218] Synthesis of organometallic compound 1

[0219] Intermediate 1-H (1.0 eq) was dissolved in o-dichlorobenzene and then cooled to 0°C under nitrogen atmosphere. BBr was slowly injected 3 (16eq), the temperature was raised to about 150°C, and stirred for about 24 hours to form a reaction product. After cooling, triethylamine was slowly added dropwise to the reaction product to terminate the activity, and then the reaction product was added dropwise to ethanol for precipitation, and the precipitated solid was obtained by filtration. The solid thus obtained was filtered through silica gel using toluene, and then separated by recrystallization using toluene again to obtain an organometallic compound 1 with a yield of 20%.

[0220] (2) Synthesis of organometallic compound 2

[0221] Organometallic compound 2 was obtained by using substantially the same method as that of Synthesis Example of Organometallic Compound 1, except that 4-(tert-butyl)pyridin-2-amine was used instead of 2-aminopyridine during the synthesis process of Intermediate 1-B in Synthesis Example of Organometallic Compound 1.

[0222] (3) Synthesis of organometallic compound 3

[0223] Organometallic compound 3 is obtained by using a method substantially the same as the method of the synthesis example of organometallic compound 1, except that 4-(tert-butyl)pyridine-2-amine is used instead of 2-aminopyridine during the synthesis process of intermediate 1-B in the synthesis example of organometallic compound 1, and 1-(3-bromo-5-(tert-butyl)phenyl)-1H-imidazole is used instead of 1-(3-bromophenyl)-1H-imidazole during the synthesis process of intermediate 1-E.

[0224] (4) Synthesis of organometallic compound 4

[0225] The organometallic compound 4 was obtained by using substantially the same method as the method of the synthesis example of the organometallic compound 1, except that 2,4,6-trimethyl-N-phenylaniline was used instead of the reactant diphenylamine.

[0226] (5) Synthesis of organometallic compound 5

[0227] The organometallic compound 5 was obtained by using substantially the same method as the method of the synthesis example of the organometallic compound 1, except that carbazole was used instead of the reactant diphenylamine.

[0228] (6) Synthesis of organometallic compound 6

[0229] Organometallic compound 6 was obtained by using substantially the same method as in Synthesis Example of Organometallic Compound 1, except that 1-(3-bromophenyl)-1H-benzo[d]imidazole was used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of Intermediate 1-E.

[0230] (7) Synthesis of organometallic compound 7

[0231] Organometallic compound 7 was obtained by using substantially the same method as that of the synthesis example of organometallic compound 1, except that 1-(3-bromophenyl)-3,5-dimethyl-2,3-dihydro-1H-pyrazole was used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of intermediate 1-E.

[0232] (8) Synthesis of organometallic compound 8

[0233] Organometallic compound 8 was obtained by using substantially the same method as in Synthesis Example of Organometallic Compound 1, except that 2-(3-methyl-2,3-dihydro-1H-imidazol-1-yl)-9H-carbazole was used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of Intermediate 1-E.

[0234] (9) Synthesis of organometallic compound 9

[0235] Organometallic compound 9 was obtained by using substantially the same method as in the synthesis example of organometallic compound 1, except that 9,9-dimethyl-3-(3-methyl-2,3-dihydro-1H-imidazol-1-yl)-9,10-dihydroacridine was used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of intermediate 1-E.

[0236] (10) Synthesis of organometallic compound 10

[0237] Intermediate 1-H (1.0 eq) was dissolved in o-dichlorobenzene and then cooled to 0°C under nitrogen atmosphere. BBr was slowly injected 3 (16eq), the temperature was raised to about 190°C, and stirred for about 24 hours to form a reaction product. After cooling, triethylamine was slowly added dropwise to the reaction product to terminate the activity, and then the reaction product was added dropwise to ethanol for precipitation, and filtered to obtain a precipitated reaction product. The solid thus obtained was filtered through silica gel using toluene, and then separated by recrystallization using toluene again to obtain an organometallic compound 10 with a yield of 20%.

[0238] (11) Synthesis of organometallic compound 11

[0239] Organometallic compound 11 is obtained by using a method substantially the same as the method of the synthesis example of organometallic compound 1, except that 1-(3-bromophenyl)-1H-benzo[d]imidazole is used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of intermediate 1-E, and iodomethane-d3 is used instead of iodomethane in the synthesis step of intermediate 1-F.

[0240] (12) Synthesis of organometallic compound 12

[0241] The organometallic compound 12 was obtained by using substantially the same method as the method of the synthesis example of the organometallic compound 1, except that iodobenzene was used instead of methyl iodide in the synthesis step of the intermediate 1-F.

[0242] (13) Synthesis of organometallic compound 13

[0243] Organometallic compound 13 was obtained by using a method substantially the same as the method of the synthesis example of organometallic compound 1, except that 1-(3-bromophenyl)-1H-benzo[d]imidazole was used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of intermediate 1-E, and iodobenzene was used instead of iodomethane in the synthesis step of intermediate 1-F.

[0244] (14) Synthesis of organometallic compound 14

[0245] Organometallic compound 14 was obtained by using a method substantially the same as the method of the synthesis example of organometallic compound 1, except that 1-(3-bromophenyl)-1H-benzo[d]imidazole was used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of intermediate 1-E, and 1-iodo-4-methylbenzene was used instead of methyl iodide in the synthesis step of intermediate 1-F.

[0246] (15) Synthesis of organometallic compound 15

[0247] Organometallic compound 15 is obtained by using a method substantially the same as the method of the synthesis example of organometallic compound 1, except that 1-(3-bromophenyl)-1H-benzo[d]imidazole is used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of intermediate 1-E, and 1-iodo-4-methylbenzene-d7 is used instead of iodomethane in the synthesis step of intermediate 1-F.

[0248] (16) Synthesis of organometallic compound 16

[0249] Organometallic compound 16 was obtained by using a method substantially the same as the method of the synthesis example of organometallic compound 1, except that 1-(3-bromophenyl)-1H-benzo[d]imidazole was used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of intermediate 1-E, and 1-(tert-butyl)-4-iodobenzene was used instead of methyl iodide in the synthesis step of intermediate 1-F.

[0250] (17) Synthesis of organometallic compound 17

[0251] Organometallic compound 17 was obtained by using a method substantially the same as the method of the synthesis example of organometallic compound 1, except that 1-(3-bromophenyl)-1H-benzo[d]imidazole was used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of intermediate 1-E, and 2,4,6-trimethyliodobenzene was used instead of methyl iodide in the synthesis step of intermediate 1-F.

[0252] (18) Synthesis of organometallic compound 18

[0253] Organometallic compound 18 was obtained by using a method substantially the same as the method of the synthesis example of organometallic compound 1, except that 1-(3-bromophenyl)-1H-benzo[d]imidazole was used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of intermediate 1-E, and 2'-iodo-1,1':3',1"-terphenyl was used instead of methyl iodide in the synthesis step of intermediate 1-F.

[0254] (19) Synthesis of organometallic compound 19

[0255] Organometallic compound 19 was obtained by using a method substantially the same as the method of the synthesis example of organometallic compound 1, except that 1-(3-bromophenyl)-1H-benzo[d]imidazole was used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of intermediate 1-E, and 2'-iodo-1,1':3',1"-terphenyl-d10 was used instead of methyl iodide in the synthesis step of intermediate 1-F.

[0256] (20) Synthesis of organometallic compound 20

[0257] Organometallic compound 20 was obtained by using substantially the same method as the method of the synthesis example of organometallic compound 1, except that 1-(3-bromophenyl)-1H-benzo[d]imidazole was used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of intermediate 1-E, and 2-iodo-1,1'-biphenyl-d5 was used instead of methyl iodide in the synthesis step of intermediate 1-F.

[0258] (21) Synthesis of organometallic compound 21

[0259] The organometallic compound 21 was obtained by using substantially the same method as the method of the synthesis example of the organometallic compound 1, except that di([1,1′-biphenyl]-4-yl)amine was used instead of the reactant diphenylamine.

[0260] (22) Synthesis of organometallic compound 22

[0261] Organometallic compound 22 was obtained by using substantially the same method as the synthesis example of organometallic compound 1, except that di([1,1'-biphenyl]-4-yl)amine was used instead of the reactant diphenylamine, and 1-(3-bromophenyl)-1H-benzo[d]imidazole was used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of intermediate 1-E.

[0262] (23) Synthesis of organometallic compound 23

[0263] Organometallic compound 23 is obtained by using a method substantially the same as the method of the synthesis example of organometallic compound 1, except that di([1,1'-biphenyl]-4-yl)amine is used instead of the reactant diphenylamine, 1-(3-bromophenyl)-1H-benzo[d]imidazole is used instead of 1-(3-bromophenyl)-1H-imidazole in the synthesis step of intermediate 1-E, and iodomethane-d3 is used instead of iodomethane in the synthesis step of intermediate 1-F.

[0264] 2. Performance evaluation of organometallic compounds

[0265] The light emitting properties of the organometallic compounds of Example Compound 1, Example Compound 3, Example Compound 6, Example Compound 10, Example Compound 15, and Example Compound 20, and the organometallic compound of Comparative Compound C1 were evaluated and are shown in Table 1 below.

[0266] Exemplary compounds and comparative compound C1 are as follows.

[0267] Example compounds

[0268]

[0269] Comparative Compound C1

[0270]

[0271] Table 1

[0272]

[0273] As can be seen from Table 1, the organometallic compound 1, organometallic compound 3, organometallic compound 6, organometallic compound 10, organometallic compound 15 and organometallic compound 20 as exemplary compounds exhibited similar degrees of increased metal-ligand charge transfer when compared to the comparative compound C1 ( 3 In addition, it can be seen that the organometallic compounds of the examples exhibit an increased triplet metal neutral state ( 3 Therefore, when compared with the case of a display device including comparative compound C1, if the exemplary organometallic compound is included in a display device, improved device lifespan and emission efficiency performance may be exhibited.

[0274] When compared with the emission center wavelength of the comparative compound C1, the emission center wavelengths λ of the organometallic compounds 1, 3, 6, 10, 15, and 20 as examples are λ . max exp Corresponding to the shorter wavelength region. For example, it can be seen from the results of Table 1 that the example compound emits deep blue light as blue light in the shorter wavelength region when compared with the comparative compound C1.

[0275] 3. Manufacturing and evaluation of organic electroluminescent devices

[0276] Fabrication of organic electroluminescent devices

[0277] The organic electroluminescent device of the example including the organometallic compound of the example was manufactured as follows.

[0278] Manufacturing of Example 1

[0279] Corning's 15Ω / cm 2 The ITO glass substrate was cut into a size of 50 mm × 50 mm × 0.7 mm as a substrate and a first electrode (anode), respectively, washed by ultrasonic wave with isopropyl alcohol and pure water for 5 minutes, exposed to ultraviolet rays and ozone for about 30 minutes for washing, and the glass substrate was mounted in a vacuum deposition equipment.

[0280] On an ITO anode formed on a glass substrate, 2-TNATA was vacuum deposited to form a A hole injection layer having a thickness of about 1000 mm was formed, and NPB was vacuum deposited on the hole injection layer to form a The hole transport layer has a thickness of .

[0281] On the hole transport layer, BCPDS and POPCPA as co-hosts (the weight ratio of BCPDS and POPCPA is 1:1) and an organometallic compound 1 as a dopant are co-deposited so that the weight ratio of the co-host and the dopant becomes 90:10 to form a hole transport layer having a thickness of about 100 nm. The thickness of the emission layer.

[0282] On the emitter layer, TSPO1 is deposited to form a A hole blocking layer with a thickness of 1000 nm is formed. On the hole blocking layer, Alq 3 To form a On the electron transport layer, LiF is deposited to form an electron transport layer having a thickness of about Then, Al is deposited on the electron injection layer to form a layer having a thickness of about A second electrode (cathode) with a thickness of is formed to manufacture an organic electroluminescent device.

[0283] The compounds used in the fabrication of the organic electroluminescent device are shown below.

[0284]

[0285] Preparation of Examples 2 to 4 and Comparative Example 1

[0286] An organic electroluminescent device was manufactured by using substantially the same manufacturing method as that of Example 1, except that the organometallic compounds 3, 6, 10 and the comparative compound C1 were respectively used as dopants instead of the organometallic compound 1 during the formation of the emission layer.

[0287] Performance evaluation of organic electroluminescent devices

[0288] The driving voltage, current density, brightness, emission efficiency and emission wavelength of the organic electroluminescent devices manufactured in Examples 1 to 4 and Comparative Example 1 were measured using Keithley SMU 236 and a brightness photometer PR650, and the time (half-life) required for the initial brightness to decrease to 95% was measured. The results are shown in Table 2.

[0289] Table 2

[0290]

[0291]

[0292] In Table 2, the evaluation results of the organic electroluminescent devices of Examples 1 to 4 and Comparative Example 1 are shown. In Table 2, the driving voltage, brightness, emission efficiency, emission wavelength and life of the organic electroluminescent devices thus manufactured are compared and shown. The emission efficiency is expressed relative to 50 mA / cm 2 The current efficiency value of the current density.

[0293] Referring to the results of Table 2, it can be seen that the organic electroluminescent devices of Examples 1 to 4 exhibited similar degrees of brightness and emission efficiency when compared with the organic electroluminescent device of Comparative Example 1. However, when compared with the organic electroluminescent device of Comparative Example 1, the organic electroluminescent devices of Examples 1 to 4 exhibited reduced driving voltage and increased lifespan.

[0294] The organic metal compound of the embodiment includes a metal complex and a condensed ring group containing boron (B) as a ring-forming atom, and has a high MLCT ratio, and thus can exhibit high quantum efficiency. In addition, the organic electroluminescent device of the embodiment includes an organic metal compound having a metal complex and a condensed ring group containing boron (B) as a ring-forming atom in the emission layer, and can exhibit excellent emission efficiency performance and improved life characteristics.

[0295] The organic electroluminescent device of the embodiment includes an organic metal compound having a substituent having a boron-containing condensed ring, and can exhibit improved device performance of high efficiency and long lifespan.

[0296] The organometallic compound of the embodiment includes a boron-containing condensed ring group and can help improve the efficiency and lifetime of an organic electroluminescent device.

[0297] Although exemplary embodiments of the present disclosure have been described, it should be understood that the present disclosure should not be limited to these exemplary embodiments. On the contrary, the present disclosure is intended to cover various changes and modifications that may be made by one of ordinary skill in the art within the spirit and scope of the appended claims and their equivalents.

Claims

1. An organic metal compound, the organic metal compound is represented by the following formula 1: In formula 1, M is Pt, Y is O, S or Se, Q1 to Q4 are independently C or N, L1 is represented by any one of the groups selected from the following group L: Group L In the group L, R is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, L4 is a pyridyl group, Any one selected from b1 to b3 is 1, and the rest are 0, where The corresponding one of X1 to X3 is B, L2, L3 and A1 to A4 are all independently phenyl, R1 to R8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, a1 to a8 are each independently an integer from 0 to 3, and Substitution means substitution with at least one of a deuterium atom and an alkyl group having 1 to 10 carbon atoms.

2. The organometallic compound according to claim 1, wherein Formula 1 is represented by any one selected from the following Formulas 1-1 to 1-3: Formula 1-1 Formula 1-2 Formula 1-3 In Formulae 1-1 to 1-3, M, Y, Q1 to Q4, L1 to L4, A1 to A4, R1 to R8, and a1 to a8 are the same as defined with respect to Formula 1.

3. The organometallic compound according to claim 1, wherein Formula 1 is represented by the following formula 2-A: Formula 2-A In Formula 2-A, Y, L1, b1 to b3, X1 to X3, A1 to A4, R1 to R8 and a1 to a8 are the same as those defined with respect to Formula 1, Q1 to Q3 are C, and Q4 is N.

4. The organometallic compound according to claim 1, wherein L1 is represented by L-7 or L-100.

5. An organometallic compound, comprising any one of the compounds in the following compound group 1: Compound Group 1 6. An organic electroluminescent device, comprising: a first electrode; a second electrode, located on the first electrode; as well as an emission layer, located between the first electrode and the second electrode, Wherein, the emission layer comprises the organic metal compound according to any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, wherein: The emitting layer emits phosphorescence.

8. The organic electroluminescent device according to claim 6, wherein: The emission layer includes a host and a dopant, and The dopant is represented by Formula 1 or includes the compound of claim 5.

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