Organic metal compound, organic light-emitting device including the same, and electronic device including the organic light-emitting device

Abstract

Disclosed are an organic metal compound, an organic light-emitting device including the organic light-emitting device, and an electronic device including the organic light-emitting device. The organic metal compound is represented by Formula 1, wherein in Formula 1, M 1 For transition metals, Ln 1 is a ligand represented by Formula 1A, Ln 2 is a ligand represented by Formula 1B, n1 is 1 or 2, and n2 is 1 or 2, wherein the groups and parameters of Formulas 1A and 1B are as provided herein in the detailed description. 1 (Ln 1 ) n1 (Ln 2 ) n2 #imgabs0#.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application is based on and claims the benefit of priority and all rights arising from Korean Patent Application No. 10-2021-0096714 filed on July 22, 2021, and Korean Patent Application No. 10-2022-0057394 filed on May 10, 2022, in the Korean Intellectual Property Office, the contents of which are incorporated herein in their entirety by reference. Technical Field

[0003] The present disclosure relates to an organometallic compound, an organic light-emitting device including the same, and an electronic device (apparatus) including the organic light-emitting device. Background Art

[0004] An organic light emitting device (OLED) is a self-emitting device that has improved characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed and produces a full-color image.

[0005] In an example, an organic light emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode and including an emission layer. A hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. Holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. Summary of the invention

[0006] Provided are a novel organometallic compound, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device.

[0007] Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.

[0008] According to one aspect, an organometallic compound represented by Formula 1 is provided:

[0009] Formula 1

[0010] M 1 (Ln 1 ) n1 (Ln 2 ) n2

[0011] Among them, in formula 1,

[0012] M 1 For transition metals,

[0013] Ln 1 is a ligand represented by Formula 1A,

[0014] Ln 2 is a ligand represented by Formula 1B,

[0015] n1 is 1 or 2, and

[0016] n2 is 1 or 2,

[0017]

[0018] CY 1 and CY 2 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0019] CY 3 is a heterocyclic group including a 5-membered heterocyclic ring (a 5-membered ring containing a heteroatom),

[0020] CY 4 is a group represented by formula 40,

[0021] X 1 is C or N, and X 2 is C or N,

[0022] X 3 is C or N, and X 4 is C or N,

[0023] Y 1 for O, S, Se, C(R 3 )(R 4 )、N(R 3 ), or B(R 3 ),

[0024] Y 41 and Y 42 are each independently a single bond, -O-, -S-, -Se-, -C(R 5 )(R 6 )-、-N(R 5 )-, or-B(R 5 )-,

[0025] Y 41 and Y 42 Different from both being single keys,

[0026] R 10 and R 20are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

[0027] R 1 -R 6 , R 30 , and R 40are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ), or -P(=O)(Q 8 )(Q 9 ),

[0028] Multiple R 10 Two or more of are optionally linked together to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0029] Multiple R 20 Two or more of are optionally linked together to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0030] Multiple R 30 Two or more of are optionally linked together to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0031] Multiple R 40 Two or more of are optionally linked together to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0032] R 1 -R 6 , R 10 , R 20 , R 30 , and R 40 Two or more adjacent groups are optionally linked together to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0033] b10, b20, b30, and b40 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10,

[0034] * and *' respectively represent 1 The binding site

[0035] Substituted C 5 -C 30 Carbocyclic groups, substituted C 1 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 1 -C 60 Alkylthio, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Alkyl aryl, substituted C 7 -C 60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 2 -C 60 Heteroarylalkyl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:

[0036] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio;

[0037] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-Ge(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(Q 18 )(Q 19 )、-P(=O)(Q 18 )(Q 19 ), or a combination thereof;

[0038] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;

[0039] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6-C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(Q 28 )(Q 29 )、-P(=O)(Q 28 )(Q 29 ), or a combination thereof; or

[0040] -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(Q 38 )(Q 39 ), or -P(=O)(Q 38 )(Q 39 ),and

[0041] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0042] According to another aspect, an organic light emitting device is provided, comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and wherein the organic layer comprises at least one organic metal compound represented by Formula 1.

[0043] The at least one organometallic compound may be included in the emission layer of the organic layer, and in this regard, may serve as a dopant.

[0044] According to yet another aspect, an electronic device including the organic light emitting device is provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0045] The above and other aspects, features, and advantages of some embodiments of the present disclosure will be more apparent from the following description considered in conjunction with the accompanying drawings.

[0046] Figure 1 Schematic cross-sectional views showing organic light emitting devices according to one or more embodiments. DETAILED DESCRIPTION

[0047] Embodiments will now be described in detail, examples of which are shown in the accompanying drawings, wherein the same reference numerals throughout the specification refer to the same elements. In this regard, the present embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the following only describes the embodiments to illustrate aspects by reference to the accompanying drawings. As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. Expressions such as "at least one (kind)" when before or after a list of elements modify the entire list of elements and do not modify the individual elements of the list.

[0048] The terms used herein are only for the purpose of describing one or more exemplary embodiments and are not intended to be restrictive. As used herein, the singular forms "a (one) (indefinite article) (a, an)" and "the (the)" are also intended to include plural forms, unless the context clearly indicates otherwise. The term "or" means "and / or". It will be further understood that the term "comprising" or "including" when used in this specification indicates the presence of stated features, regions, wholes, steps, operations, elements and / or components, but does not exclude the presence or addition of one or more other features, regions, wholes, steps, operations, elements, components, and / or their collections.

[0049] It will be understood that although the terms first, second, third, etc. can be used to describe various elements, components, regions, layers and / or parts in this article, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish an element, component, region, layer or part from another element, component, region, layer or part. Therefore, without departing from the teaching of the present embodiment, the first element, component, region, layer or part discussed below can be referred to as the second element, component, region, layer or part.

[0050] Exemplary embodiments are described herein with reference to cross-sectional views as schematic diagrams of idealized embodiments. Thus, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are to be expected. Therefore, the embodiments described herein should not be construed as being limited to the specific shapes of the regions as illustrated herein, but rather include deviations in shape caused by, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. Moreover, the illustrated sharp corners may be rounded. Therefore, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shapes of the regions and are not intended to limit the scope of the claims.

[0051] It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with the other element or intervening elements may exist therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements.

[0052] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the present disclosure and the relevant art, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0053] As used herein, "about" or "approximately" includes the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean that the deviation from the stated value is within one or more standard deviations, or within ±10% or 5%.

[0054] One aspect provides an organometallic compound represented by Formula 1:

[0055] Formula 1

[0056] M 1 (Ln 1 ) n1 (Ln 2 ) n2 .

[0057] In formula 1, M 1 For transition metals.

[0058] In one or more embodiments, M in Formula 1 1 It may be a 4th period transition metal, a 5th period transition metal, or a 6th period transition metal of the periodic table.

[0059] In one or more embodiments, M in Formula 1 1 It may be iridium (Ir), platinum (Pt), palladium (Pd), gold (Au), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0060] In one or more embodiments, M in Formula 1 1 It may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0061] In one or more embodiments, M in Formula 1 1 It can be Ir, Os, Pt, Pd, or Au.

[0062] In one or more embodiments, M in Formula 1 1 It can be Ir.

[0063] In Formula 1, n1 is 1 or 2.

[0064] In Formula 1, n2 is 1 or 2.

[0065] In one or more embodiments, M in Formula 1 1 It can be Ir, and the sum of n1 and n2 can be equal to 3.

[0066] In formula 1, Ln 1 It may be a ligand represented by Formula 1A:

[0067]

[0068] In Formula 1A, CY 1 and CY 2 Each is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.

[0069] In Formula 1A, X 1 It is C or N.

[0070] In Formula 1A, X 2 It is C or N.

[0071] In Formula 1A, R 10 and R 20 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. 10 Two or more of are optionally linked together to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic group. Multiple R 20 Two or more of are optionally linked together to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic group. 10 and R 20 Two or more adjacent groups are optionally linked together to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic group.

[0072] In Formula 1A, b10 and b20 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0073] In Formula 1A, * and *' each represent 1 binding site.

[0074] In one or more embodiments, X in Formula 1A 1 and M in formula 1 1 The bond between X and X may be a covalent bond or a coordination bond. 1 and M in formula 1 1 The bond between them can be a coordination bond.

[0075] In one or more embodiments, X in Formula 1A 2 and M in formula 1 1 The bond between X and X may be a covalent bond or a coordination bond. 2 and M in formula 1 1 The bond between them can be a covalent bond.

[0076] In one or more embodiments, Ln 1 It can be represented by formula 1A-1:

[0077]

[0078] Wherein, in Formula 1A-1,

[0079] X 11 Can be C(R 11 ) or N, X 12 Can be C(R 12 ) or N, X 13 Can be C(R 13 ) or N, and X 14 Can be C(R 14 ) or N,

[0080] X 21 Can be C(R 21 ) or N, X 22 Can be C(R 22 ) or N, X 23 Can be C(R 23 ) or N, and X 24 Can be C(R 24 ) or N,

[0081] R 11 -R 14 can be independently determined as R 10 As described,

[0082] R21 -R 24 can be independently determined as R 20 described, and

[0083] * and *' respectively represent 1 binding site.

[0084] In one or more embodiments, Ln 1 It may be represented by one or more of Formulas 1A-11 to 1A-26:

[0085]

[0086] Wherein, in Formulas 1A-11 to 1A-26,

[0087] R 10 and R 20 may each be as described herein,

[0088] b51 and b54 can each independently be 1 or 2,

[0089] b53 and b55 can each independently be 1, 2, or 3,

[0090] b52 and b56 may each independently be 1, 2, 3, or 4, and

[0091] * and *' respectively represent 1 binding site.

[0092] In one or more embodiments, in Formula 1A, The part represented by can be represented by one of formulas 1-1 to 1-16:

[0093]

[0094] Among them, in formulas 1-1 to 1-16,

[0095] R 11 -R 14 can be independently determined as R 10 As described,

[0096] *Indicates the same as M 1 The binding site of , and *' indicates the binding site with the adjacent atom.

[0097] In one or more embodiments, R 11 -R 14 Each may not be hydrogen.

[0098] In one or more embodiments, R 11 -R 14can be independently deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, or naphthyl.

[0099] In one or more embodiments, in Formula 1A, The part represented can be represented by one of the formulas 2-1 to 2-16:

[0100]

[0101] Among them, in formulas 2-1 to 2-16,

[0102] R 21 -R 24 can be independently determined as R 20 described, and

[0103] *Indicates the same as M 1 The *" indicates the binding site with the adjacent atom.

[0104] In one or more embodiments, R 21 -R 24 Each may not be hydrogen.

[0105] In one or more embodiments, R 21 -R 24 can be independently deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, or naphthyl.

[0106] In formula 1, Ln 2 is a ligand represented by Formula 1B:

[0107]

[0108] Wherein, in Formula 1B, CY 4 It may be a group represented by Formula 40:

[0109]

[0110] Where, in formula 40, Y 41 and Y 42 Each independently represents a single bond, O, S, Se, C(R 5 )(R 6 )、N(R 5 ), or B(R 5 ).

[0111] In formula 40, Y 41 and Y 42 Not all are single bonds.

[0112] In Formula 1B, Y 1 for O, S, Se, C(R 3 )(R 4 )、N(R 3 ), or B(R 3 ).

[0113] In Formula 1B, X 3 is C or N, and X 4 It is C or N.

[0114] In Formula 1B, X 3 and M in formula 1 1 The bond between them is a coordination bond.

[0115] In Formula 1B, X 4 and M in formula 1 1 The bond between them is a covalent bond.

[0116] In one or more embodiments, Ln 2 It may be represented by one or more of Formulas 1B-1 to 1B-3:

[0117]

[0118]

[0119]

[0120] Wherein, in Formulas 1B-1 to 1B-3,

[0121] CY 3 , X 3 , Y 1 , Y 41 , Y 42 , R 1 , R2 , R 30 , and b30 may be as described herein, respectively,

[0122] R 41 -R 48 can be independently determined as R 40 described, and

[0123] * and *' respectively represent 1 binding site.

[0124] In one or more embodiments, Ln 2 It may be represented by one or more of formulas 1B-11 to 1B-16:

[0125]

[0126]

[0127] Wherein, in Formulas 1B-11 to 1B-16,

[0128] CY 3 , X 3 , Y 1 , Y 41 , Y 42 , R 1 , R 2 , R 30 , and b30 may be as described herein, respectively,

[0129] R 41 -R 48 can be independently determined as R 40 described, and

[0130] * and *' respectively represent 1 binding site.

[0131] In Formula 1B, CY 3 is a heterocyclic group including a 5-membered ring containing a heteroatom.

[0132] In one or more embodiments, CY 3 It can be represented by formula 3A or 3B:

[0133]

[0134] Wherein, in Formulas 3A and 3B,

[0135] X 31 Can be C(R 31 ) or N, X 32 Can be C(R 32 ) or N, X 33Can be C(R 33 ) or N, X 34 Can be C(R 34 ) or N, and X 35 Can be C(R 35 )(R 36 ) or N(R 35 ),

[0136] R 31 -R 36 Each can be as about R 30 described, and

[0137] *Indicates the same as M 1 The binding site of , and *' indicates the binding site with the adjacent atom.

[0138] In one or more embodiments, CY 3 It can be represented by one or more of formulas 3-1 to 3-12:

[0139]

[0140] Among them, in formulas 3-1 to 3-12,

[0141] R 31 -R 35 Each can be as about R 30 described, and

[0142] *Indicates the same as M 1 The binding site of , and *' indicates the binding site with the adjacent atom.

[0143] In Formula 1B, R 1 -R 6 , R 30 , and R 40 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ), or -P(=O)(Q 8 )(Q 9 ).

[0144] In one or more embodiments, in Formula 1A, R 10 and R 20 Can be independently:

[0145] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1 -C 20 Alkyl, C 2 -C 20 Alkenyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio;

[0146] Each of the following C 1 -C 20 Alkyl, C 2 -C 20 Alkenyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (bicyclo[2.2.1]heptyl), norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C 1 -C 20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C 1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C 20 Alkyl) norbornyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20alkyl)bicyclo[1.1.1]pentyl, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl)bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, or a combination thereof; or

[0147] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 1 -C 20alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C 1 -C 20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C 1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C 20 Alkyl) norbornyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl)bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or a combination thereof.

[0148] In one or more embodiments, R 1 -R 6 , R 30 , and R 40 Can be independently:

[0149] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 2 -C 20 Alkenyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio;

[0150] Each of C is substituted by 1 -C 20 Alkyl, C 2 -C 20 Alkenyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (bicyclo[2.2.1]heptyl), norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C 1 -C 20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C 1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C20 Alkyl) norbornyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl)bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, or a combination thereof;

[0151] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 1 -C 20 alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C 1 -C 20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C 1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C 20 Alkyl) norbornyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl)bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or a combination thereof; or

[0152] -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ), or -P(=O)(Q 8 )(Q 9 ),and

[0153] Q 1 -Q 9 Can be independently:

[0154] Deuterium, -F, -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H.-CD 2 CDH 2 , -CF 3, -CF 2 H, -CFH 2 、-CH 2 CF 3 、-CH 2 CF 2 H, -CH 2 CFH 2 、-CHFCH 3 , -CHFCF 2 H, -CHFCFH 2 , -CHFCF 3 , -CF 2 CF 3 , -CF 2 CF 2 H, or -CF 2 CFH 2 ;or

[0155] n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl, each unsubstituted or substituted with at least one of the following: deuterium, -F, C 1 -C 10 Alkyl, phenyl, or a combination thereof.

[0156] In one or more embodiments, R 10 and R 20 Can be independently:

[0157] Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 alkylthio; or

[0158] A group represented by one of the formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350, and

[0159] R 1 -R6 , R 30 , and R 40 Can be independently:

[0160] Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, -Si(Q 1 )(Q 2 )(Q 3 ), or -Ge(Q 1 )(Q 2 )(Q 3 );or

[0161] A group represented by one of the formulae 9-1 to 9-67, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350:

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172] Wherein, in Formulas 9-1 to 9-67, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350, * represents a bonding site with an adjacent atom, "Ph" is a phenyl group, "TMS" is a trimethylsilyl group, and "TMG" is a trimethylgermyl group.

[0173] In one or more embodiments, R 1 -R 6 , R 10 , R 20 , R 30 , and R 40 can each independently be hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C 1 -C 20 Alkylphenyl, or naphthyl.

[0174] When b10 is 2 or more, two or more R 10 may be the same as or different from each other, and when b20 is 2 or greater, two or more R 20 may be the same as or different from each other, and when b30 is 2 or greater, two or more R 30 may be the same as or different from each other, and when b40 is 2 or more, two or more R 40 Can be the same as or different from each other.

[0175] In Formula 1A, multiple R 10 Two or more of; multiple R 20 Two or more of; multiple R 30 Two or more of; multiple R 40 two or more of; or R 1 -R 6 , R 10 , R 20 , R 30 , and R 40 Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic group.

[0176] In one or more embodiments, multiple R 10 Two or more of; multiple R 20 Two or more of; multiple R 30 Two or more of; multiple R 40two or more of; or R 1 -R 6 , R 10 , R 20 , R 30 , and R 40 Two or more adjacent groups may be optionally linked together via a single bond, a double bond, or a first linking group to form a group that is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups (eg, each unsubstituted or substituted with at least one R 10a substituted fluorene group, xanthene group, acridine group, etc.). 10a As for R 10 as described.

[0177] The first linking group may be selected from *-N(R 8 )-*'、*-B(R 8 )-*'、*-P(R 8 )-*'、*-C(R 8 )(R 9 )-*'、*-Si(R 8 )(R 9 )-*'、*-Ge(R 8 )(R 9 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(R 8 )=*'、*=C(R 8 )-*'、*-C(R 8 )=C(R 9 )-*', *-C(=S)-*', and *-C≡C-*', where R 8 and R 9 Each can be as about R 10 As described, * and *' each represent a binding site with an adjacent atom.

[0178] In one or more embodiments, the organometallic compound may be represented by one of Formulas 30-1 to 30-12:

[0179]

[0180]

[0181]

[0182]

[0183]

[0184] Among them, in formulas 30-1 to 30-12,

[0185] X 31 Can be C(R 31 ) or N, X 32 Can be C(R 32 ) or N, X 33 Can be C(R 33 ) or N, X 34 Can be C(R 34 ) or N, and X 35 Can be C(R 35 )(R 36 ) or N(R 35 ),

[0186] M 1 、n1、n2、R 1 , and R 2 As described in this article,

[0187] R 11 -R 14 can be independently determined as R 10 As described,

[0188] R 21 -R 24 can be independently determined as R 20 As described,

[0189] R 31 -R 36 can be independently determined as R 30 described, and

[0190] R 41 -R 48 can be independently determined as R 40 as described.

[0191] In one or more embodiments, the organometallic compound may be electrically neutral.

[0192] In one or more embodiments, the organometallic compound may be one or more of compounds 1 to 40:

[0193]

[0194]

[0195]

[0196] The organometallic compound represented by Formula 1 may satisfy the structure of Formula 1 described above. In detail, the ligand represented by Formula 1B may include: 3 A heterocyclic group including a 5-membered ring containing a heteroatom represented by CY 4 The condensed ring represented by Formula 1 is a ring. Therefore, without wishing to be bound by theory, the organometallic compound represented by Formula 1 may have a long conjugated structure, thereby improving molecular stability and photoinduced orientation. Due to this structure, an electronic device such as an organic light-emitting device including the organometallic compound represented by Formula 1 may exhibit low driving voltage, high efficiency, and long life, and have a reduced emission peak half width (full width at half maximum) (FWHM).

[0197] The highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, the lowest triplet state (T 1 ) energy level, and the lowest singlet state (S 1 ) energy levels, and the results are shown in Table 1 in electron volts (eV).

[0198] Table 1

[0199]

[0200]

[0201] Referring to Table 1, it was confirmed that the organometallic compound represented by Formula 1 had suitable electrical characteristics for use as a dopant in an electronic device such as an organic light-emitting device.

[0202] In one or more embodiments, the FWHM of the emission peak of the emission spectrum or electroluminescence spectrum of the organometallic compound may be equal to or less than 75 nanometers (nm). In one or more embodiments, the FWHM of the emission peak of the emission spectrum or electroluminescence (EL) spectrum of the organometallic compound may be in the range of about 30 nm to about 75 nm, about 40 nm to about 70 nm, or about 45 nm to about 68 nm.

[0203] In one or more embodiments, the maximum emission wavelength (λ 最大 , nm) may be in the range of about 490 nm to about 550 nm.

[0204] The synthesis method of the organometallic compound represented by Formula 1 may be recognized by those skilled in the art by referring to the synthesis examples described below.

[0205] Therefore, the organometallic compound represented by Formula 1 can be suitable for use as a dopant in an organic layer, such as an emission layer, of an organic light-emitting device. Therefore, another aspect of the present disclosure provides an organic light-emitting device, comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer comprises at least one organometallic compound represented by Formula 1.

[0206] Since the organic light emitting device includes an organic layer including the organometallic compound represented by Formula 1 as described above, it can exhibit excellent characteristics in terms of driving voltage, current efficiency, external quantum efficiency, roll-off ratio, and lifespan, and a relatively narrow FWHM of an emission peak of an EL spectrum.

[0207] The organic metal compound represented by Formula 1 may be arranged or located between the electrode pair (i.e., the first electrode and the second electrode) of the organic light-emitting device. For example, the organic metal compound represented by Formula 1 may be included in the emission layer. In this regard, the organic metal compound may act as a dopant, and the emission layer may further include a host (i.e., the amount of the organic metal compound represented by Formula 1 in the emission layer is less than the amount of the host included in the emission layer).

[0208] According to another aspect, an organic light emitting device is provided, comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and wherein the organic layer comprises at least one organic metal compound represented by Formula 1.

[0209] In one or more embodiments, the emission layer may emit green light. For example, the emission layer may emit green light having a maximum emission wavelength in the range of about 490 nm to about 550 nm.

[0210] As used herein, the expression “(the organic layer) includes at least one organic metal compound represented by Formula 1” may include the case where “(the organic layer) includes the same organic metal compound represented by Formula 1” and the case where “(the organic layer) includes two or more different organic metal compounds represented by Formula 1”.

[0211] In one or more embodiments, the organic layer may include only Compound 1 as the organometallic compound. In this regard, Compound 1 may be included in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include Compound 1 and Compound 2 as the organometallic compound. In this embodiment, Compound 1 and Compound 2 may be present in the same layer (e.g., Compound 1 and Compound 2 may all be present in the emission layer).

[0212] The first electrode may be an anode as a hole injection electrode, and the second electrode may be a cathode as an electron injection electrode; or the first electrode may be a cathode as an electron injection electrode, and the second electrode may be an anode as a hole injection electrode.

[0213] In one or more embodiments, in the organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region arranged between the first electrode and the emission layer, and an electron transport region arranged between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0214] The term "organic layer" as used herein refers to a single layer or a plurality of layers located between a first electrode and a second electrode of an organic light emitting device. In addition to organic compounds, the "organic layer" may further include an organic metal complex including a metal.

[0215] Figure 1 FIG. 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Figure 1 The structure and manufacturing method of the organic light emitting device 10 according to one or more embodiments of the present disclosure are described. The organic light emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19 which are sequentially stacked.

[0216] A substrate may be additionally disposed below (or under) the first electrode 11 or above (or on) the second electrode 19. For use as the substrate, any suitable substrate used in an organic light-emitting device in the related art may be used, and for example, a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, easy handling (processing), and / or water resistance may be used.

[0217] The first electrode 11 may be formed, for example, by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, the material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), or zinc oxide (ZnO). In one or more embodiments, the material used to form the first electrode 11 may be a metal such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0218] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 11 is not limited thereto.

[0219] The organic layer 15 is disposed on the first electrode 11 .

[0220] In one or more embodiments, the organic layer 15 may include: the hole transport region; the emission layer; and the electron transport region.

[0221] The hole transport region may be disposed between the first electrode 11 and the emission layer.

[0222] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.

[0223] The hole transport region may include only a hole injection layer or a hole transport layer. The hole transport region may have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the constituent layers of each structure are sequentially stacked in the stated order starting from the first electrode 11.

[0224] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, casting, and / or Langmuir-Blodgett (LB) deposition.

[0225] When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature in the range of about 100° C. to about 500° C., a ... -8 Torr - about 10 -3The vacuum pressure is in the range of 1000 torr, and at about 0.01 angstrom / second. -about However, the deposition conditions are not limited thereto.

[0226] When the hole injection layer is formed by spin coating, the coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, the coating conditions may include a coating speed in the range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and a heat treatment temperature in the range of about 80° C. to about 200° C. for removing the solvent after coating. However, the coating conditions are not limited thereto.

[0227] Conditions for forming the hole transport layer and the electron blocking layer may be similar to the conditions for forming the hole injection layer, respectively.

[0228] The hole transport region may include, for example, at least one of 4,4′,4″-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N′-di(naphthalen-1-yl)-N,N′-diphenyl-benzidine (NPB), β-NPB, N,N′-di(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4′-cyclohexylidenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), 4,4′,4″-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, or a compound represented by Formula 202:

[0229]

[0230]

[0231] Wherein, in formula 201, Ar 101 and Ar 102 Can be independently:

[0232] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthenylene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyren ... phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene phenylene, tetraphenylene, perylene, perylene, or pentphenylene; or

[0233] each substituted with at least one of the following: phenylene, pentalene, indenylene, naphthylene, azulenylene, heptalene, acenaphthene, fluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, acenaphthene, fluor ... phenanthrenylene, phenanthrenylene, phen phenylene, tetraphenylene, perylene, or pentphenylene: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.

[0234] In Formula 201, xa and xb may each independently be an integer of 0 to 5, or may each independently be 0, 1, or 2. For example, xa may be 1, and xb may be 0, but xa and xb are not limited thereto.

[0235] In equations 201 and 202, R 101 -R 108 , R 111 -R 119 , and R 121 -R 124 Can be independently:

[0236] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), C 1 -C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentyloxy, etc.), or C 1 -C 10 Alkylthio;

[0237] Each of the following C 1- C 10 Alkyl, C 1 -C 10 Alkoxy, or C 1 -C 10 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, or phosphoric acid group or its salt;

[0238] Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl; or

[0239] Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl, each substituted with at least one of: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, or C 1 -C 10 Alkylthio,

[0240] However, the embodiment is not limited thereto.

[0241] In formula 201, R 109 Can be:

[0242] phenyl, naphthyl, anthracenyl, or pyridyl; and

[0243] phenyl, naphthyl, anthracenyl, or pyridyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 1 -C 20 alkylthio, phenyl, naphthyl, anthracenyl, or pyridyl.

[0244] In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but the embodiments are not limited thereto:

[0245]

[0246]

[0247] Wherein, in Formula 201A, R 101 , R 111 , R 112 , and R 109 May each independently be as described herein.

[0248] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include one or more of compounds HT1 to HT20, but the embodiment is not limited thereto:

[0249]

[0250]

[0251]

[0252] The thickness of the hole transport region may be about about For example, about about When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about about For example, about about In the range of, and the thickness of the hole transport layer may be about about For example, about about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics may be obtained without a significant increase in driving voltage.

[0253] In addition to these materials, the hole transport region may further include a charge generating material to improve the conductive property. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0254] The charge generating material may be, for example, a p-type dopant. The p-type dopant may be one of the following: a quinone derivative, a metal oxide, and a compound containing a cyano group, but the embodiments of the present disclosure are not limited thereto. For example, non-limiting examples of the p-type dopant are: a quinone derivative such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), and F6-TCNNQ; a metal oxide such as tungsten oxide or molybdenum oxide; or a compound containing a cyano group, such as one or more of compounds HT-D1 or F12, but the embodiments are not limited thereto:

[0255]

[0256] The hole transport region may further include a buffer layer.

[0257] The buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of a formed light emitting device may be improved.

[0258] Then, the emission layer can be formed on the hole transport region by using one or more suitable methods such as vacuum deposition, spin coating, casting, and / or LB deposition. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions can be similar to those applied when forming the hole injection layer, although the deposition or coating conditions can vary depending on the material used to form the emission layer.

[0259] Meanwhile, when the hole transport region includes an electron blocking layer, the material for forming the electron blocking layer may be selected from the materials for the hole transport region described above and the host material to be described later. However, the material for forming the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material for forming the electron blocking layer may be mCP to be described below.

[0260] The emission layer may include a host and a dopant, and the dopant may include an organic metal compound represented by Formula 1.

[0261] In one or more embodiments, the host may include at least one of 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), 9,10-di(naphthalene-2-yl)anthracene (ADN, also referred to as "DNA"), 4,4'-di(N-carbazolyl)-1,1'-biphenyl (CBP), 4,4'-di(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), TCP, mCP, compound H50, or compound H51:

[0262]

[0263] In one or more embodiments, the host may include a compound represented by Formula 301:

[0264]

[0265] Wherein, in Formula 301, Ar 111 and Ar 112 Can be independently:

[0266] Phenylene, naphthylene, phenanthrenyl, or pyrenylene; or

[0267] Phenylene, naphthylene, phenanthrenylene, or pyrenylene, each substituted with at least one of phenyl, naphthyl, or anthracenyl.

[0268] In formula 301, Ar 113 -Ar 116 Can be independently:

[0269] C 1 -C 10 alkyl, phenyl, naphthyl, phenanthrenyl, or pyrenyl; or

[0270] Phenyl, naphthyl, phenanthrenyl, or pyrenyl, each substituted with at least one of the following: phenyl, naphthyl, or anthracenyl.

[0271] In Formula 301, g, h, i, and j may each independently be an integer of 0-4, and for example, may each independently be 0, 1, or 2.

[0272] In formula 301, Ar 113 -Ar 116 Can be independently:

[0273] C substituted with at least one of the following 1 -C10 Alkyl: phenyl, naphthyl, or anthracenyl;

[0274] Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl;

[0275] Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl, each substituted with at least one of: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 alkylthio, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl; or

[0276]

[0277] However, the embodiment is not limited thereto.

[0278] In one or more embodiments, the host may include a compound represented by Formula 302:

[0279]

[0280] Wherein, in formula 302, Ar 122 -Ar 125 can be independently as for Ar in formula 301 113 As described.

[0281] In formula 302, Ar 126 and Ar 127 Can be independently C 1 -C 10 Alkyl (eg, methyl, ethyl, or propyl).

[0282] In formula 302, k and l may each independently be an integer of 0 to 4. For example, k and l may each independently be 0, 1, or 2.

[0283] When the organic light emitting device 10 is a full-color organic light emitting device, the emission layer can be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, based on a stacked structure including a red emission layer, a green emission layer, and / or a blue emission layer, the emission layer can emit white light, and various modifications are possible.

[0284] When the emission layer includes both a host and a dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.

[0285] The thickness of the emission layer may be about about For example, about about When the thickness of the emission layer is within these ranges, excellent light emitting characteristics can be obtained without a significant increase in driving voltage.

[0286] Next, the electron transport region is disposed on the emission layer.

[0287] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0288] For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a multilayer structure or a single layer structure including two or more different materials.

[0289] Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region may be similar to the conditions for forming the hole injection layer.

[0290] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), or bis(2-methyl-8-hydroxyquinoline-N1,08)-(1,1′-biphenyl-4-hydroxy)aluminum (BAlq), but embodiments are not limited thereto:

[0291]

[0292]

[0293] The thickness of the hole blocking layer may be about about For example, about about When the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics may be obtained without a significant increase in driving voltage.

[0294] The electron transport layer may further include at least one of the following: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinoline)aluminum (Alq 3 ), bis(2-methyl-8-hydroxyquinoline-N1,08)-(1,1′-biphenyl-4-hydroxy)aluminum (BAlq), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), or 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ):

[0295]

[0296] In one or more embodiments, the electron transport layer may include at least one of compounds ET1 to ET25, but embodiments of the present disclosure are not limited thereto:

[0297]

[0298]

[0299] The thickness of the electron transport layer may be about about For example, about about When the thickness of the electron transport layer is within these ranges, satisfactory electron transport characteristics may be obtained without a significant increase in driving voltage.

[0300] The electron transport layer may further include a material containing a metal in addition to the materials described above.

[0301] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium quinolate (LiQ)) or ET-D2:

[0302]

[0303] The electron transport region may further include an electron injection layer that facilitates the flow of electrons from the second electrode 19 therein.

[0304] The electron injection layer may include at least one of the following: LiF, NaCl, CsF, Li 2 O, or BaO.

[0305] The thickness of the electron injection layer can be about about and for example about about When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage.

[0306] A second electrode 19 is arranged on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a metal, an alloy, a conductive compound, or a combination thereof having a relatively low work function. For example, the material used to form the second electrode 19 may be lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag). In order to manufacture a top-emitting light-emitting device, various modifications are possible, and for example, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0307] In the previous article, reference has been made to Figure 1 The organic light emitting device is described, but embodiments of the present disclosure are not limited thereto.

[0308] Another aspect of the present disclosure provides a diagnostic composition comprising at least one organometallic compound represented by Formula 1.

[0309] The organometallic compound represented by Formula 1 provides high luminescence efficiency, and thus, a diagnostic composition including the at least one organometallic compound may have high diagnostic efficiency.

[0310] The diagnostic compositions can be used in a variety of applications including diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0311] As used herein, the term "C 1 -C 60 "Alkyl" refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof are methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, and the like. As used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 Alkyl is a divalent group of the same structure.

[0312] As used herein, the term "C 1 -C 60 "Alkoxy" refers to a 101 (A 101 C 1 -C 60 An alkyl group is a monovalent group represented by an alkyl group, and examples thereof are methoxy, ethoxy, isopropoxy and the like.

[0313] As used herein, the term "C 1 -C 60 "Alkylthio" refers to -SA 101’ (A 101’ C 1 -C 60 A monovalent group represented by an alkyl group.

[0314] As used herein, the term "C 2 -C 60 "Alkenyl" refers to a group consisting of 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon double bond in the middle or at the terminal of an alkyl group, and examples thereof are vinyl, propenyl, butenyl, and the like. 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0315] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon triple bond in the middle or at the terminal of an alkyl group, and examples thereof are ethynyl, propynyl, and the like. 2 -C 60 "Alkyne" refers to a group having a C 2 -C 60 Alkynyl is a divalent group of the same structure.

[0316] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc. 3 -C 10 "Cycloalkylene" refers to a cycloalkylene having a 3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0317] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si, Se, Ge, and S as a ring atom and having 1 to 10 carbon atoms, and examples thereof are tetrahydrofuranyl, tetrahydrothienyl, and the like. As used herein, the term "C 1 -C 10"Heterocycloalkylene" refers to a group having a C 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0318] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity, and examples thereof are cyclopentenyl, cyclohexenyl, cycloheptenyl, etc. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0319] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, P, Si, Se, Ge, and S as a ring atom in its ring, having 1 to 10 carbon atoms and at least one carbon-carbon double bond. 1 -C 10 Examples of heterocycloalkenyl are 2,3-dihydrofuranyl, 2,3-dihydrothienyl, and the like. 1 -C 10 "Heterocycloalkenylene" refers to a 1 -C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0320] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Examples of aryl groups are phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, Ji et al. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the two or more rings may be fused to each other.

[0321] As used herein, the term "C 1 -C 60"Heteroaryl" refers to a monovalent group having an aromatic system having at least one heteroatom selected from N, O, P, Si, Se, Ge, and S as a ring atom and having 1 to 60 carbon atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having an aromatic system having at least one heteroatom selected from N, O, P, Si, Se, Ge, and S as a ring atom and having 1 to 60 carbon atoms. 1 -C 60 Examples of heteroaryl are pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, and the like. 6 -C 60 Heteroaryl and C 6 -C 60 When the heteroarylene groups each include two or more rings, the two or more rings may be fused to each other.

[0322] As used herein, the term "C 6 -C 60 "Aryloxy" means -OA 102 (A 102 C 6 -C 60 aryl), and as used herein the term "C 6 -C 60 "Arylthio" means -SA 103 (A 103 C 6 -C 60 aryl).

[0323] As used herein, the term "C 1 -C 60 "Heteroaryloxy" means -OA 102’ (A 102’ C 1 -C 60 heteroaryl), and as used herein, the term "C 1 -C 60 "Heteroarylthio" means -SA 103’ (A 103’ C 1 -C 60 heteroaryl).

[0324] As used herein, the term "C 7 -C 60 "Alkylaryl" refers to a C 1 -C 30 Alkyl substituted C 6 -C 30 Aryl. As used herein, the term "C7 -C 60 "Arylalkyl" refers to a C 6 -C 30 Aryl substituted C 1-30 alkyl.

[0325] As used herein, the term "C 2 -C 60 "Alkylheteroaryl" refers to a C 1 -C 30 Alkyl substituted C 1 -C 30 As used herein, the term "C 2 -C 60 "Heteroarylalkyl" refers to a C 1 -C 30 Heteroaryl-substituted C 1 -C 30 alkyl.

[0326] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other, having only carbon atoms as ring-forming atoms, and not having aromaticity in terms of its entire molecular structure. Examples of monovalent non-aromatic fused polycyclic groups are fluorenyl and the like. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group described above.

[0327] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (for example, having 2 to 60 carbon atoms) having two or more rings fused to each other, having at least one heteroatom selected from N, O, P, Si, Se, Ge, and S as a ring-forming atom in addition to carbon atoms and not having aromaticity in terms of its entire molecular structure. Examples of monovalent non-aromatic fused heteropolycyclic groups are carbazolyl and the like. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group described above.

[0328] As used herein, the term "C 5 -C 30 The term "carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring atoms. 5 -C 30 The carbocyclic group may be a monocyclic group or a polycyclic group.

[0329] As used herein, the term "C 1 -C 30The term "heterocyclic group" refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, P, Si, Se, Ge, and S as a ring atom in addition to 1 to 30 carbon atoms. 1 -C 30 The heterocyclic group may be a monocyclic group or a polycyclic group.

[0330] Substituted C 5 -C 30 Carbocyclic groups, substituted C 1 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 1 -C 60 Alkylthio, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Alkyl aryl, substituted C 7 -C 60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 2 -C 60 Heteroarylalkyl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

[0331] Deuterium, -F, -Cl, -Br, -I, -SF5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1-60 Alkylthio;

[0332] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1-60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(Q 18 )(Q 19 ), or -P(=O)(Q 18 )(Q 19 );

[0333] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;

[0334] Each of the following is substituted by at least one C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(Q 28 )(Q 29 ), or -P(=O)(Q 28 )(Q 29 );or

[0335] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(Q 38 )(Q 39 ), or -P(=O)(Q 38 )(Q 39 ),and

[0336] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, each of which is unsubstituted or substituted by at least one of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, C 1 -C 60 Alkyl, or C 6 -C 60 Aryl.

[0337] Hereinafter, the compound and the organic light-emitting device according to one or more exemplary embodiments are further described in detail with reference to Synthesis Examples and Examples. However, the compound and the organic light-emitting device are not limited thereto. The phrase "using 'B' instead of 'A'" used in describing the Synthesis Examples means that, in terms of molar equivalents, the amount of 'A' used is the same as the amount of 'B' used.

[0338] Example

[0339] Synthesis Example 1: Synthesis of Compound 1

[0340]

[0341] (1) Synthesis of Compound 1A(1)

[0342] 2-Phenylpyridine (33.1 mmol) and iridium chloride hydrate (IrCl 3 ·(H 2 O) n, n=3)) (5.2 grams (g), 14.7 mmol) was mixed with 120 milliliters (mL) of ethoxyethanol and 40 mL of deionized (DI) water, and stirred under reflux for 24 hours. Then, the reaction temperature was lowered to room temperature. The solid produced therein was separated by filtration, washed thoroughly with water, methanol, and hexane in the order stated, and then dried in a vacuum oven to obtain 8.2 g (82% yield) of compound 1A (1).

[0343] (2) Synthesis of Compound 1A

[0344] Compound 1A (1) (1.6 g, 1.2 mmol) and 45 mL of dichloromethane (MC) were mixed to prepare a reaction mixture, and a mixed solution containing silver trifluoromethanesulfonate (AgOTf, 0.6 g, 2.3 mmol) and 15 mL of methanol (MeOH) was added thereto. Afterwards, while blocking light with aluminum foil, the resulting reaction solution was stirred at room temperature for 18 hours, and filtered through diatomaceous earth to remove the solid produced therein. The filtrate was then subjected to decompression to obtain a solid (Compound 1A), which was used in the next reaction without additional purification processes.

[0345] (3) Synthesis of Compound 1B

[0346] Under nitrogen atmosphere, 2-(Benzo[b]benzo[4,5]furo[2,3-f]benzofuran-10-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.8 g, 2.03 mmol) and 2-bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole (0.8 g, 1.85 mmol) were dissolved in 45 mL of 1,4-dioxane to prepare a reaction mixture. Then, potassium carbonate (KCO) dissolved in 15 mL of DI water was added. 2 CO 3 ) (0.59 g, 5.55 mmol) was added to the reaction mixture, and tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 , 0.11g, 0.09mmol) was added to the reaction mixture. Afterwards, the resulting reaction mixture was heated at 100°C under reflux. The reaction mixture was filtered, and the filtrate obtained was extracted and evaporated to obtain a solid. The solid obtained after extraction and evaporation was subjected to column chromatography (eluent: MC and hexane) to obtain 0.8g (73% yield) of compound 1B. The obtained compound was confirmed by high resolution mass spectrometry (HRMS) and high performance liquid chromatography (HPLC) analysis using matrix-assisted laser desorption ionization (MALDI).

[0347] HRMS (MALDI): For C 43 H 34 N 2 O 2 Calculated value: m / z: 610.76, found: 611.32.

[0348] (4) Synthesis of Compound 1

[0349] 10mL 2-ethoxyethanol and 10mL N, N-dimethylformamide were mixed with compound 1A (1.1g, 1.5mmol) and compound 1B (1.0g, 1.6mmol), stirred under reflux for 24 hours, and then the temperature was lowered. The extraction process was performed using dichloromethane and water, and the water layer was removed therefrom. The resulting product was treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained solid was subjected to column chromatography (eluent: dichloromethane (MC) and hexane) to obtain 0.27g (21% yield) of compound 1. The obtained compound was confirmed by HRMS and HPLC analysis.

[0350] HRMS (MALDI): For C 65 H 49 Ir 4 O 2 Calculated value: m / z: 1110.35, found value: 1111.13.

[0351] Synthesis Example 2: Synthesis of Compound 2

[0352]

[0353] 0.07 g (6% yield) of compound 2 was obtained in a similar manner to the synthesis of compound 1, except that (benzo[b]benzo[4,5]furo[3,2-g]benzofuran-10-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-(benzo[b]benzo[4,5]furo[2,3-f]benzofuran-10-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The obtained compound was confirmed by HRMS and HPLC analysis.

[0354] HRMS (MALDI): For C 65 H 49 Ir 4 O 2 Calculated value: m / z: 1110.35, found value: 1111.21.

[0355] Synthesis Example 3: Synthesis of Compound 6

[0356]

[0357] (1) Synthesis of Compound 6B

[0358] Under nitrogen atmosphere, 2-(12,12-dimethyl-12H-fluoren[1,2-b]benzofuran-10-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.04 g, 2.53 mmol) and 2-bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole (1.00 g, 2.31 mmol) were dissolved in 45 mL of 1,4-dioxane to prepare a reaction mixture. Then, potassium carbonate (KCO) dissolved in 15 mL of DI water was added. 2 CO 3 ) (0.73 g, 6.92 mmol) was added to the reaction mixture, and Pd(PPh 3 ) 4 (0.13 g, 0.12 mmol) was added to the reaction mixture. Afterwards, the resulting reaction mixture was stirred at 100 ° C under reflux. The solid obtained after extraction was subjected to column chromatography (eluent: MC and hexane) to obtain 1.28 g (87% yield) of compound 6B. The obtained compound was confirmed by high resolution mass spectrometry (HRMS) and high performance liquid chromatography (HPLC) analysis using matrix-assisted laser desorption ionization (MALDI).

[0359] HRMS (MALDI): For C 46 H 40 N 2 Calculated value for O: m / z: 636.84, found: 637.79.

[0360] (2) Synthesis of Compound 6

[0361] 0.74 g (35% yield) of Compound 6 was obtained in a similar manner to the synthesis of Compound 1, except that Compound 6B (1.18 g, 1.85 mmol) was used instead of Compound 1B (1.0 g, 1.6 mmol). The obtained compound was confirmed by HRMS and HPLC analysis.

[0362] HRMS (MALDI): For C 68 H 55 Ir 4 Calculated value for O: m / z: 1136.43, found: 1137.22.

[0363] Example 1

[0364] The ITO (as anode) patterned glass substrate was cut into a size of 50 millimeters (mm)×50 mm×0.5 mm, sonicated with isopropyl alcohol and DI water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The resulting glass substrate was loaded onto a vacuum deposition apparatus.

[0365] Compounds HT3 and F12 (p-type dopant) were vacuum co-deposited on the anode at a weight ratio of 98:2 to form a A hole injection layer having a thickness of , and compound HT3 is vacuum deposited on the hole injection layer to form a The hole transport layer has a thickness of .

[0366] Then, compound GH3 (host) and compound 1 (dopant) were co-deposited on the hole transport layer by vacuum at a weight ratio of 92:8 to form a The thickness of the emission layer.

[0367] Then, compound ET3 and LiQ (n-type dopant) were co-deposited on the emission layer in a volume ratio of 50:50 to form a An electron transport layer having a thickness of , LiQ is vacuum deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Al is vacuum deposited on the electron injection layer to form A cathode with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.

[0368]

[0369] Examples 2 and 3 and Comparative Examples 1-3

[0370] Organic light-emitting devices were manufactured in a similar manner to that in Example 1, except that in forming the emission layer, the compounds shown in Table 2 were used instead of Compound 1 as dopants, respectively.

[0371] The driving voltage, maximum external quantum efficiency (maximum EQE, %), maximum emission wavelength (λ) of the emission spectrum of the organic light-emitting devices manufactured according to Examples 1-3 and Comparative Examples 1-3 were evaluated. 最大 , nm), and lifetime (LT 97 , relative %), and the results are shown in Table 2. As evaluation equipment, a current-voltage meter (Keithley 2400) and a brightness meter (Minolta Cs-1000A) were used. Lifespan (LT 97 ) (at 6,000 candelas / square meter or nit) was evaluated by measuring the time for achieving 97% of the initial brightness (100%), and reported as a relative value based on Comparative Example 1 (which is 100%).

[0372] Table 2

[0373]

[0374]

[0375] Referring to Table 2, it is confirmed that the organic light-emitting devices of Examples 1-3 have excellent EQE, low driving voltage, and long life characteristics. In addition, it is confirmed that the organic light-emitting devices of Examples 1-3 have lower or equivalent driving voltage, higher or equivalent EQE, and longer life relative to the organic light-emitting devices of Comparative Examples 1-3.

[0376] According to one or more embodiments, the organometallic compound represented by Formula 1 may have excellent electrical characteristics and stability. Therefore, an electronic device including the organometallic compound, such as an organic light-emitting device, may have a low driving voltage, high efficiency, long life, reduced roll-off ratio, and a relatively narrow half width (FWHM) of an emission peak of an electroluminescence (EL) spectrum. Therefore, due to the use of the organometallic compound, a high-quality organic light-emitting device may be realized.

[0377] It should be understood that the exemplary embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each exemplary embodiment should typically be considered to be applicable to other similar features or aspects in other exemplary embodiments. Although one or more exemplary embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that various changes in form and detail may be made therein without departing from the spirit and scope as defined by the appended claims.

Claims

1. An organic metal compound represented by one of Formulas 30-7 and 30-10: Formula 30-7 Formula 30-10 in, In formulas 30-7 and 30-10, M1 is Ir, n1 is 1 or 2, n2 is 1 or 2, The sum of n1 and n2 is 3, Y1 is -O- or -S-, Y 41 is -O-, -S-, -C(R5)(R6)-, or -N(R5)-, Y 42 is -O- or -S-, Depend on The part represented by is expressed by formula 3-5: R 11 -R 14 , R 21 -R 24 , R 31 -R 34 , R 41 -R 46 , R 48 , R1-R2, and R5-R6 are each independently: hydrogen, deuterium, C1-C 20 Alkyl, or C1-C 20 alkoxy; or C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -CD3, -CD2H, -CDH2, or a combination thereof, R 35 is biphenyl, terphenyl, naphthyl, phenanthryl, or anthracenyl, each of which is unsubstituted or substituted with deuterium, -CD3, -CD2H, -CDH2, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, C1-C 20 Alkoxy, or a combination thereof, * indicates the binding site with M1, and *' indicates the binding site with the adjacent atom.

2. The organometallic compound according to claim 1, wherein R 11 -R 14 , R 21 -R 24 , R 31 -R 34 , R 41 -R 46 , R 48 , R1-R2, and R5-R6 are each independently hydrogen, deuterium, -CD3, -CD2H, -CDH2, or a group represented by one of formulae 9-1 to 9-39 and 9-44 to 9-61, and R 35 is a group represented by one of the formulae 10-59 to 10-62, 10-64, 10-65, 10-73 to 10-95, 10-115 to 10-129, 10-206, 10-207, 10-311 to 10-314, and 10-346: in, In the above formula, * represents a bonding site with an adjacent atom, and "Ph" is a phenyl group.

3. The organometallic compound according to claim 1, wherein the organometallic compound is electrically neutral.

4. The organometallic compound according to claim 1, wherein the organometallic compound is one or more of the following compounds:

5. An organic light emitting device comprising: a first electrode; a second electrode; as well as an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and The organic layer comprises at least one organic metal compound as claimed in any one of claims 1 to 4.

6. An organic light emitting device as claimed in claim 5, wherein the emissive layer comprises the at least one organometallic compound. 7 . The organic light emitting device of claim 6 , wherein the emission layer further comprises a host, and an amount of the host in the emission layer is greater than an amount of the at least one organometallic compound in the emission layer.

8. The organic light emitting device according to claim 5, wherein The first electrode is an anode, The second electrode is a cathode, The organic layer further includes a hole transport region disposed between the first electrode and the emission layer, and an electron transport region disposed between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

9. An electronic device comprising the organic light emitting device according to any one of claims 5 to 8.

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