Organometallic compound, organic light-emitting device including same, and electronic device including organic light-emitting device

Abstract

Disclosed are an organometallic compound, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device. The organometallic compound is represented by Formula 1, where M1 is a transition metal, L1 is a ligand represented by Formula 1A, L2 is a ligand represented by Formula 1B, and n1 and n2 are each independently 1 or 2, where X43 is C (R43), N, or C bonded to Y3; x44 is C (R44), N, or C bonded to Y2 or Y3; x45 is C (R45), N, or C bonded to Y2 or Y3; and X46 is C (R46), N, or C bonded to Y2, where i) X43 is C bonded to Y3 and X44 is C bonded to Y2; ii) X44 is C bonded to Y3, and X45 is C bonded to Y2; or iii) X45 is C bonded to Y3, and X46 is C bonded to Y2, and the remaining groups and variables are as described herein. Formula 1M1 (L1) n1 (L2) n2 # imgabs 0 # and formula 2 # imgabs 1 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefits of Korean Patent Application No. 10-2023-0094657 filed in the Korean Intellectual Property Office on July 20, 2023, and all rights arising therefrom, the entire contents of which are incorporated herein 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 including the organic light-emitting device. Background Art

[0004] An organic light emitting device (OLED) is a self-emitting device having improved characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed. In addition, an OLED can produce a full-color image.

[0005] OLED 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. Excitons may transition from an excited state to a ground state, thereby generating light. Summary of the invention

[0006] Provided are an organic metal 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 detailed description which follows and, in part, will be apparent from the detailed description, or may be learned by practice of the exemplary embodiments presented herein.

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

[0009] Formula 1

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

[0011] Among them, in formula 1,

[0012] M 1 For transition metals,

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

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

[0015] n1 and n2 are each independently 1 or 2,

[0016] Formula 1A

[0017]

[0018] Formula 1B

[0019]

[0020] Formula 2

[0021]

[0022] Wherein, in Formulas 1A, 1B, and 2,

[0023] X 1 C or N, X 2 C or N, X 3 C or N, X 4 is C or N,

[0024] Cyclo 1 CY 2 , and ring CY 5 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0025] Cyclo 3 is (i) a 6-membered carbocyclic group, (ii) a 6-membered heterocyclic group, (iii) 5 -C 30 A 6-membered carbocyclic group fused to a carbocyclic group, or a 1 -C 30 A 6-membered carbocyclic group fused to a heterocyclic group, or (iv) a 6-membered carbocyclic group fused to a heterocyclic group 5 -C 30 A 6-membered heterocyclic group fused to a carbocyclic group, or a 1 -C 30 a 6-membered heterocyclic group fused to a heterocyclic group,

[0026] Z 1 and Z 2 Each is independently -Si(Q 1 )(Q 2 )(Q 3 ) or -Ge(Q 1 )(Q 2 )(Q3 ),

[0027] a1 and a2 are each independently an integer of 0-10,

[0028] The sum of a1 and a2 is 1 or greater,

[0029] X 41 C(R 41 ) or N, X 42 C(R 42 ) or N,

[0030] X 43 C(R 43 ), N, or with Y in formula 2 3 Bonded C;X 44 C(R 44 ), N, or with Y in formula 2 2 or Y 3 Bonded C;X 45 C(R 45 ), N, or with Y in formula 2 2 or Y 3 bonded C; and X 46 C(R 46 ), N, or with Y in formula 2 2 Bonded C,

[0031] The condition is, i) X 43 is the same as Y in Eq. 2 3 Bonded C, and X 44 is the same as Y in Eq. 2 2 Bonded C, ii) X 44 is the same as Y in Eq. 2 3 Bonded C, and X 45 is the same as Y in Eq. 2 2 Bonded C, or iii) X 45 is the same as Y in Eq. 2 3 Bonded C, and X 46 is the same as Y in Eq. 2 2 Bonded C,

[0032] Y 1 for O, S, Se, B(R 61 )、N(R 61 ), or C(R 61 )(R 62 ),

[0033] Y 2 For single bonds, O, S, Se, B (R 63 )、N(R 63 )、C(R 63 )(R64 )、Si(R 63 )(R 64 ), or Ge(R 63 )(R 64 ),

[0034] Y 3 For single bonds, O, S, Se, B (R 65 )、N(R 65 )、C(R 65 )(R 66 )、Si(R 65 )(R 66 ), or Ge(R 65 )(R 66 ),

[0035] At least one of conditions 1 and 2 must be met:

[0036] Condition 1

[0037] Y 2 Si(R 63 )(R 64 ) or Ge(R 63 )(R 64 ),

[0038] Condition 2

[0039] Y 3 Si(R 65 )(R 66 ) or Ge(R 65 )(R 66 ),

[0040] R 1 -R 3 , R 5 , R 41 -R 46 , and R 61 -R 66 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 -C60 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 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 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 ),

[0041] Two or more adjacent R 1 are optionally bonded together to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C30 Heterocyclic groups,

[0042] Two or more adjacent R 2 are optionally bonded 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,

[0043] b1-b3 and b5 are each independently an integer of 1-10,

[0044] In Formulae 1A and 1B, * and *' each represent 1 The binding site

[0045] In Formula 2, * and *' each represent a binding site with an adjacent atom,

[0046] 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 60Alkyl heteroaryl, substituted C 2 -C 60 Heteroarylalkyl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 Substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are:

[0047] Deuterium, -F, -Cl, -Br, -I, -SF 5 、-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, or C 1 -C 60 Alkylthio,

[0048] 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, -SF 5 、-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 -C10 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 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,

[0049] 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,

[0050] 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, 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, 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, C6 -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 )(Q 22 )(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

[0051] -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

[0052] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q29 , 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 -C 10 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.

[0053] According to another aspect, an organic light emitting device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes at least one of the organometallic compounds described above.

[0054] At least one of the organometallic compounds described herein may be included in the emission layer of the organic layer, and the organometallic compound included in the emission layer may serve as a dopant.

[0055] According to another aspect, an electronic device includes the organic light emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0056] The above and other aspects, features, and advantages of certain exemplary embodiments will become more apparent from the following detailed description considered in conjunction with the accompanying drawings, in which:

[0057] Figure 1 is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments. DETAILED DESCRIPTION

[0058] Exemplary embodiments will now be described in further detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the exemplary embodiments may have different forms and should not be construed as being limited to the detailed description set forth herein. Therefore, exemplary embodiments are only described in further detail below with reference to the accompanying drawings to illustrate some aspects and features. As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. Statements such as "at least one (kind) of" when before or after a list of elements modify the entire list of elements without modifying the individual elements of the list.

[0059] The terms used herein are only used for the purpose of describing one or more exemplary embodiments and are not intended to be limiting. 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.

[0060] 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 other elements, components, regions, layers or parts. 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.

[0061] 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 shown 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.

[0062] It will be understood that when an element is referred to as being “on” another element, it can be in direct 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.

[0063] 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 this 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 this disclosure and the relevant art, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0064] 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 within one or more standard deviations, or within ±10% or 5% relative to the stated value.

[0065] As used herein, an "energy level" (e.g., a singlet state (S 1 ) energy level or triplet state (T 1) energy level) is expressed as an absolute value from the vacuum energy level. In addition, when the energy level is referred to as "deep", "high" or "large", the energy level has a large absolute value based on the vacuum energy level of "0 electron volt (eV)", and when the energy level is referred to as "shallow", "low" or "small", the energy level has a small absolute value based on the vacuum energy level of "0 eV".

[0066] As used herein, when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g., phenyl, naphthyl, etc.) or as if it were an entire molecule (e.g., benzene, naphthalene, etc.). It will be understood that the nomenclature may be used interchangeably herein.

[0067] One aspect provides an organometallic compound represented by Formula 1:

[0068] Formula 1

[0069] M 1 (L 1 ) n1 (L 2 ) n2

[0070] Among them, in formula 1, M 1 For transition metals.

[0071] For example, M 1 It may be a first row transition metal of the periodic table, a second row transition metal of the periodic table, or a third row transition metal of the periodic table.

[0072] In one or more embodiments, M 1 It may be iridium (Ir), platinum (Pt), osmium (Os), palladium (Pd), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0073] In one or more embodiments, M 1 It may be iridium, platinum, osmium, or rhodium.

[0074] In one or more embodiments, M 1 It may be iridium.

[0075] In Formula 1, n1 is 1 or 2, and n2 is 1 or 2.

[0076] In one or more embodiments, the sum of n1 and n2 may be 2 or 3.

[0077] In one or more embodiments, M 1 It can be iridium, and the sum of n1 and n2 can be 3.

[0078] In one or more embodiments, M 1 It may be platinum, and the sum of n1 and n2 may be 2.

[0079] L in Formula 1 1 is a ligand represented by Formula 1A:

[0080] Formula 1A

[0081]

[0082] Wherein, in Formula 1A, X 1 is C or N, and X 2 It is C or N.

[0083] In one or more embodiments, X 1 Can be N, and X 2 Can be C.

[0084] In Formula 1A, ring CY 1 and CY 2 Can be independently C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.

[0085] In one or more embodiments, CY 1 and CY 2 may each independently be: i) a first ring, ii) a second ring, iii) a fused ring system in which at least two first rings are fused to each other, iv) a fused ring system in which at least two second rings are fused to each other, or v) a fused ring system in which at least one first ring is fused to at least one second ring,

[0086] The first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a thiorrole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzothiorrole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothitriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiorrole group, a diazathiorrole group, or a triazathiorrole group, and

[0087] The second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0088] In one or more embodiments, CY 1 and CY 2Each of the above groups may independently be a benzene group, a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

[0089] In one or more embodiments,

[0090] Cyclo 1 may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group, and

[0091] Cyclo 2 It may be a benzene group or a naphthyl group.

[0092] In one or more embodiments, in Formula 1A, The moiety represented by may be a group represented by one of the formulae CY(1)-1 to CY(1)-32:

[0093]

[0094]

[0095]

[0096] Wherein, in formulas CY(1)-1 to CY(1)-32,

[0097] R 11 -R 14 Each independently as described herein for R 1 As described, the condition is R 11 -R 14 Not hydrogen, Z 1 As described in this article,

[0098] *Indicates the same as M 1 The binding site, and

[0099] *” indicates the binding site with the adjacent atoms.

[0100] For example, R 11 -R 14 may be each independently C substituted with at least one deuterium 1 -C 10 Alkyl (e.g., -CD 3 、-CD 2 H.-CDH 2 wait).

[0101] In one or more embodiments, in Formula 1A, The moiety represented by may be a group represented by one of the formulae CY(2)-1 to CY(2)-32:

[0102]

[0103]

[0104] Wherein, in formulas CY(2)-1 to CY(2)-32,

[0105] R 21 -R 24 Each independently as described herein for R 2 As described, the condition is R 21 -R 24 Not hydrogen, Z 2 As described in this article,

[0106] *Indicates the same as M 1 The binding site, and

[0107] *” indicates the binding site with the adjacent atoms.

[0108] In one or more embodiments, in Formula 1A, The moiety represented by may be a group represented by one of the formulae CY(2A)-1 to CY(2A)-16:

[0109]

[0110] Wherein, in formulae CY(2A)-1 to CY(2A)-16,

[0111] R 21 -R 24 Each independently as described herein for R 2 As described, the condition is R 21 -R 24 Not hydrogen,

[0112] *' indicates that the 1 The binding site, and

[0113] *” indicates the binding site with the adjacent atoms.

[0114] In Formula 1A, Z 1 and Z 2 Each is independently -Si(Q 1 )(Q 2 )(Q 3 ) or -Ge(Q 1 )(Q 2)(Q 3 ), where Q 1 -Q 3 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 -C 10 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.

[0115] In one or more embodiments, Q 1 -Q3 Can be independently:

[0116] Deuterium, -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, or -CD 2 CDH 2 ;

[0117] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0118] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of: deuterium, C 1 -C 10 Alkyl, phenyl, or a combination thereof.

[0119] For example, Z 1 Q 1 -Q 3 Can be independently -CH 3 、-CD 3 、-CD 2 H, or -CDH 2 .

[0120] For example, Z 2 Q 1 -Q 3 Can be independently -CH 3 、-CD 3 、-CD 2 H, or -CDH 2 .

[0121] In Formula 1A, a1 and a2 are each independently an integer of 0 to 10, and

[0122] The sum of a1 and a2 in Formula 1A is 1 or more.

[0123] In one or more embodiments, the sum of a1 and a2 may be 1.

[0124] For example, i) a1 may be 1 and a2 may be 0, or ii) a1 may be 0 and a2 may be 1.

[0125] In one or more embodiments, L 1 It may be a ligand represented by Formula 1A-1:

[0126]

[0127] Wherein, in Formula 1A-1

[0128] X 1 Can be C or N, and X 2 Can be C or N,

[0129] 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,

[0130] 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,

[0131] R 11 -R 14 Each independently as described herein for R 1 As described,

[0132] R 21 -R 24 Each independently as described herein for R 2 As described,

[0133] R 11 -R 14 and R 21 -R 24 At least one of them may be independently -Si(Q 1 )(Q 2 )(Q3 ) or -Ge(Q 1 )(Q 2 )(Q 3 ), where Q 1 -Q 3 each as described herein, and

[0134] * and *' respectively represent 1 binding site.

[0135] L in Formula 1 2 is a ligand represented by Formula 1B:

[0136] Formula 1B

[0137]

[0138] Wherein, in Formula 1B, X 3 is C or N, and X 4 It is C or N.

[0139] In one or more embodiments, X 3 Can be N, and X 4 Can be C.

[0140] In Formula 1B, ring CY 3 is: (i) a 6-membered carbocyclic group; (ii) a 6-membered heterocyclic group; (iii) 5 -C 30 A 6-membered carbocyclic group fused to a carbocyclic group, or a 1 -C 30 A 6-membered carbocyclic group fused to a heterocyclic group; or (iv) 5 -C 30 A 6-membered heterocyclic group fused to a carbocyclic group, or a 1 -C 30 The heterocyclic group is a condensed 6-membered heterocyclic group.

[0141] In one or more embodiments, CY 3 may be: i) a first ring, ii) a second ring, iii) a fused ring group in which two or more first rings are fused to each other, iv) a fused ring group in which two or more second rings are fused to each other, or v) a fused ring group in which at least one first ring is fused to at least one second ring, provided that ring CY 3 Connected to M via a 6-membered carbocyclic group or a 6-membered heterocyclic group contained therein 1 and containing X 4 , X 41 and X 42 The ring,

[0142] The first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a thiorrole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzothiorrole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothitriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiorrole group, a diazathiorrole group, or a triazathiorrole group, and

[0143] The second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0144] In one or more embodiments, CY 3 It may be a benzene group, a naphthyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0145] In one or more embodiments, in Formula 1B, The moiety represented by may be a group represented by one of the formulae CY(3)-1 to CY(3)-16:

[0146]

[0147] Wherein, in formulas CY(3)-1 to CY(3)-16,

[0148] R 31 -R 34 Each independently as described herein for R 3 As described, the condition is R 31 -R 34 Each is not hydrogen,

[0149] *Indicates the same as M 1 The binding site, and

[0150] *” indicates the binding site with the adjacent atoms.

[0151] For example, R 31 -R 34 may be each independently C substituted with at least one deuterium 1 -C 10 Alkyl (e.g., -CD 3 、-CD 2 H.-CDH 2 wait).

[0152] In Formula 1B, X 41 C(R 41 ) or N, and X42 C(R 42 ) or N.

[0153] In Formula 1B, X 43 C(R 43 ), N, or with Y in formula 2 3 Bonded C;X 44 C(R 44 ), N, or with Y in formula 2 2 or Y 3 Bonded C;X 45 C(R 45 ), N, or with Y in formula 2 2 or Y 3 bonded C; and X 46 C(R 46 ), N, or with Y in formula 2 2 Bonded C,

[0154] The condition is, i) X 43 is the same as Y in Eq. 2 3 Bonded C, and X 44 is the same as Y in Eq. 2 2 Bonded C; ii) X 44 is the same as Y in Eq. 2 3 Bonded C, and X 45 is the same as Y in Eq. 2 2 bonded C; or iii) X 45 is the same as Y in Eq. 2 3 Bonded C, and X 46 is the same as Y in Eq. 2 2 Bonded C:

[0155] Formula 2

[0156]

[0157] The detailed description of Formula 2 is as described herein.

[0158] In Formula 1B, Y 1 for O, S, Se, B(R 61 )、N(R 61 ), or C(R 61 )(R 62 ).

[0159] In formula 2, Y 2 For single bonds, O, S, Se, B (R 63 )、N(R 63 )、C(R 63 )(R 64 )、Si(R 63 )(R64 ), or Ge(R 63 )(R 64 ).

[0160] In formula 2, Y 3 For single bonds, O, S, Se, B (R 65 )、N(R 65 )、C(R 65 )(R 66 )、Si(R 65 )(R 66 ), or Ge(R 65 )(R 66 ).

[0161] In Formula 2, at least one of Condition 1 and Condition 2 is satisfied:

[0162] Condition 1

[0163] Y 2 Si(R 63 )(R 64 ) or Ge(R 63 )(R 64 ),

[0164] Condition 2

[0165] Y 3 Si(R 65 )(R 66 ) or Ge(R 65 )(R 66 ).

[0166] In one or more embodiments, Y 2 or Y 3 One of them may be a single bond.

[0167] For example, Y 2 can be a single bond, and Y 3 Can be Si(R 65 )(R 66 ) or Ge(R 65 )(R 66 ).

[0168] For example, Y 2 Can be Si(R 63 )(R 64 ) or Ge(R 63 )(R 64 ), and Y 3 Can be a single bond.

[0169] In Formula 2, ring CY 5 C 5 -C 30 Carbocyclic group or C1 -C 30 Heterocyclic group.

[0170] In one or more embodiments, CY 5 It may be a benzene group, a naphthyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0171] In one or more embodiments, L 2 It may be a ligand represented by one of Formulas 1B-1 to 1B-3:

[0172]

[0173] Wherein, in Formulas 1B-1 to 1B-3,

[0174] Cyclo 3 CY 5 , X 41 -X 46 , Y 1 -Y 3 , R 3 , b3, R 5 , and b5 are each as described herein, and

[0175] * and *' respectively represent 1 binding site.

[0176] In one or more embodiments, L 2 It may be a ligand represented by one of Formulas 1B(1)-1 to 1B(1)-6:

[0177]

[0178]

[0179] Wherein, in Formulas 1B(1)-1 to 1B(1)-6,

[0180] Cyclo 3 , X 41 -X 46 , Y 1 -Y 3 , R 3 , and b3 are each as described herein,

[0181] X 51 Can be C(R 51 ) or N, X 52 Can be C(R 52 ) or N, X 53 Can be C(R 53 ) or N, X 54 Can be C(R 54) or N,

[0182] R 51 -R 54 Each independently as described herein for R 5 described, and

[0183] * and *' respectively represent 1 binding site.

[0184] In Formulas 1A, 1B, and 2, R 1 -R 3 , R 5 , R 41 -R 46 , and R 61 -R 66 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 -C 10 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 -C60 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 ).

[0185] In one or more embodiments, R 1 -R 3 , R 5 , R 41 -R 46 , and R 61 -R 66 Can be independently:

[0186] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 、-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, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio;

[0187] Each of the following C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or C1 -C 20 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, 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, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, or a combination thereof;

[0188] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl;

[0189] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -SF5 、-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, C 1 -C 20 Alkoxy, C 1 -C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or a combination thereof; or

[0190] -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

[0191] Q 1 -Q 9 Can be independently:

[0192] -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, or -CD 2 CDH 2 ;

[0193] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0194] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of: deuterium, C 1 -C 10 Alkyl, phenyl, or a combination thereof.

[0195] In one or more embodiments, R 1 -R 3 , R 5 , R 41 -R 46 , and R 61 -R 66 Can be independently:

[0196] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 、-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;

[0197] A group represented by one of formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, or 10-201 to 10-350; or

[0198] -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 ), or -N(Q 4 )(Q 5 ),and

[0199] Q 1 -Q 5 As described in this article:

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] In formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, 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.

[0211] In Formula 1A, two or more adjacent R 1 may be optionally bonded 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.

[0212] In Formula 1A, two or more adjacent R 2 may be optionally bonded 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.

[0213] In Formulae 1A, 1B, and 2, b1-b3 and b5 are each independently an integer of 1-10.

[0214] In Formulae 1A, 1B, and 2, * and *' each represent 1 binding site.

[0215] In one or more embodiments, the organometallic compound may be represented by one of Formulas 5-1 to 5-6:

[0216]

[0217]

[0218]

[0219] Among them, in formulas 5-1 to 5-6,

[0220] M 1 、n1、n2、X 41 -X 46 , and Y 1 -Y 3 Each as described herein,

[0221] 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,

[0222] 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,

[0223] X 31Can be C(R 31 ) or N, X 32 Can be C(R 32 ) or N, X 33 Can be C(R 33 ) or N, and X 34 Can be C(R 34 ) or N,

[0224] X 51 Can be C(R 51 ) or N, X 52 Can be C(R 52 ) or N, X 53 Can be C(R 53 ) or N, and X 54 Can be C(R 54 ) or N,

[0225] R 11 -R 14 Each independently as described herein for R 1 As described,

[0226] R 21 -R 24 Each independently as described herein for R 2 As described,

[0227] R 11 -R 14 and R 21 -R 24 At least one of each is independently -Si(Q 1 )(Q 2 )(Q 3 ) or -Ge(Q 1 )(Q 2 )(Q 3 ), where Q 1 -Q 3 Each as described herein,

[0228] R 31 -R 34 Each independently as described herein for R 3 described, and

[0229] R 51 -R 54 Each independently as described herein for R 5 as described.

[0230] In one or more embodiments, in Formulas 5-1 to 5-6, R 11 -R 14 At least one of them may be independently -Si(Q 1 )(Q2 )(Q 3 ) or -Ge(Q 1 )(Q 2 )(Q 3 ).

[0231] In one or more embodiments, in Formulas 5-1 to 5-6, R 21 -R 24 At least one of them may be independently -Si(Q 1 )(Q 2 )(Q 3 ) or -Ge(Q 1 )(Q 2 )(Q 3 ).

[0232] In one or more embodiments, the organometallic compound may be represented by one of Compounds 1 to 128:

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244] In one or more embodiments, the organometallic compound may be electrically neutral.

[0245] The organometallic compound represented by Formula 1 satisfies the structure of Formula 1 described above and includes ligands having structures represented by Formulas 1A and 1B, wherein the ligand represented by Formula 1A includes at least one -Si(Q 1 )(Q 2 )(Q 3 ) or -Ge(Q 1 )(Q 2 )(Q3 ), and the ligand represented by Formula 1B satisfies Condition 1 (Y 2 Si(R 63 )(R 64 ) or Ge(R 63 )(R 64 )) and condition 2 (Y 3 Si(R 65 )(R 66 ) or Ge(R 65 )(R 66 Due to this structure, the organic metal compound represented by Formula 1 has excellent light emitting characteristics and has characteristics suitable for use as a light emitting material having high color purity by controlling the emission wavelength range.

[0246] In addition, the organic metal compound represented by Formula 1 has excellent electrical mobility, and therefore, an electronic device including at least one of the organic metal compounds represented by Formula 1, for example, an organic light-emitting device including the organic metal compound represented by Formula 1, may have a low driving voltage, high efficiency, and / or a long lifespan.

[0247] The density functional theory (DFT) method of Gaussian 09 program was used to calculate the highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, the singlet state (S) energy level and the molecular structure of the selected organometallic compound represented by Formula 1 under the condition of optimizing the molecular structure at the B3LYP level. 1 ) energy level, and triplet state (T 1 ) energy levels, and the results are shown in Table 1. The energy levels are expressed in electron volts (eV).

[0248] Table 1

[0249]

[0250]

[0251] As confirmed by Table 1, the organometallic compound represented by Formula 1 has such electrical characteristics as to be suitable for use as a dopant for electronic devices such as organic light emitting devices.

[0252] In one or more embodiments, the maximum emission wavelength (maximum emission peak wavelength, or peak emission wavelength, λ) of the emission peak of the emission spectrum or electroluminescence (EL) spectrum of the organometallic compound is max ) may be from about 490 nm to about 550 nm. For example, max It may be about 500 nm to about 550 nm, about 490 nm to about 540 nm, about 500 nm to about 540 nm, about 510 nm to about 540 nm, or about 490 nm to about 530 nm.

[0253] The synthesis method of the organometallic compound represented by Formula 1 may be recognized by one of ordinary skill in the art by referring to the synthesis examples provided below.

[0254] The organometallic compound represented by Formula 1 is suitable for use in an organic layer of an organic light-emitting device, for example, as a dopant in an emission layer of the organic layer. Therefore, another aspect provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer located 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 of the organometallic compounds represented by Formula 1.

[0255] By having an organic layer including at least one of the organometallic compounds represented by Formula 1 as described above, the organic light emitting device may have excellent driving voltage, high maximum external quantum efficiency, and / or high lifespan characteristics.

[0256] The organic metal compound of Formula 1 may be used between an electrode pair of an organic light-emitting device. For example, at least one of the organic metal compounds 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. When the emission layer further includes a host, the content of the host may be greater than the content of the organic metal compound based on weight.

[0257] In one or more embodiments, the emitting layer may emit green light. For example, the emitting layer may emit green light having a maximum emission wavelength of about 490 nm to about 550 nm. For example, the maximum emission wavelength may be about 500 nm to about 550 nm, about 490 nm to about 540 nm, about 500 nm to about 540 nm, about 510 nm to about 540 nm, or about 490 nm to about 530 nm.

[0258] The expressions “(the organic layer) includes at least one of the organometallic compounds represented by Formula 1” and “(the organic layer) includes at least one organometallic compound represented by Formula 1” may be used interchangeably herein and may include the case where “(the organic layer) includes the same organometallic compound represented by Formula 1” and the case where “(the organic layer) includes two or more different organometallic compounds represented by Formula 1”.

[0259] For example, the organic layer may include only Compound 1 as the at least one organic metal compound represented by Formula 1. In this embodiment, 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 at least one organic metal compound represented by Formula 1. In this embodiment, Compound 1 and Compound 2 may be present in the same layer (for example, both Compound 1 and Compound 2 may be located in the emission layer).

[0260] 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.

[0261] In one or more embodiments, in the organic light-emitting device, the first electrode is an anode, and the second electrode is a cathode, and the organic layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, and 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.

[0262] 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 the organic light emitting device. In addition to organic compounds, the "organic layer" may further include an organic metal complex including a metal.

[0263] 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 are described in further detail. The organic light emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked in the stated order.

[0264] A substrate may be additionally provided under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in an organic light-emitting device, 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 waterproofness.

[0265] The first electrode 11 can be formed by, for example, depositing or sputtering a material for forming the first electrode 11 onto the substrate. The first electrode 11 can be an anode. The material for forming the first electrode 11 can be selected from materials having a high work function to facilitate hole injection. The first electrode 11 can be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 can 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).

[0266] The first electrode 11 may have a single-layer structure or a multi-layer structure including a plurality of 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.

[0267] The organic layer 15 is located on the first electrode 11 .

[0268] The organic layer 15 may include an emission layer, and may further include a hole transport region, an electron transport region, or a combination thereof.

[0269] The hole transport region may be located between the first electrode 11 and the emission layer.

[0270] 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.

[0271] The hole transport region may include only a hole injection layer or a hole transport layer. In one or more embodiments, 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 for each structure, the corresponding layers are sequentially stacked in the order stated starting from the first electrode 11.

[0272] 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.

[0273] 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 of about 100° C. to about 500° C., a ... -8 Torr - about 10 -3 Torr vacuum pressure, and about 0.01 angstroms / second -about However, the deposition conditions are not limited thereto.

[0274] When the hole injection layer is formed using 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 speed may be about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and the temperature of heat treatment after coating to remove the solvent may be about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

[0275] Conditions for forming the hole transport layer and the electron blocking layer may be similar to or the same as conditions for forming the hole injection layer.

[0276] 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(1-naphthyl)-N,N′-diphenylbenzidine (NPB), β-NPB, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4′-diamine. '-Cyclohexylidenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-methylphenyl)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, but the embodiment is not limited thereto:

[0277]

[0278]

[0279] Formula 201

[0280]

[0281] Formula 202

[0282]

[0283] Ar in Formula 201 101 and Ar 102 Can be independently:

[0284] 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

[0285] 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 ... 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, C1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.

[0286] Xa and xb in Formula 201 may each independently be an integer of 0 to 5, or 0, 1, or 2. For example, Xa may be 1 and Xb may be 0, but Xa and Xb are not limited thereto.

[0287] R in formula 201 and 202 101 -R 108 , R 111 -R 119 and R 121 -R 124 Can be independently:

[0288] 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, or hexyl), C 1 -C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, or pentoxy), or C 1 -C 10 Alkylthio;

[0289] 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, phosphoric acid group or its salt, or a combination thereof;

[0290] Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl; or

[0291] 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, C1 -C 10 Alkoxy, C 1 -C 10 An alkylthio group, or a combination thereof, but the embodiment is not limited thereto.

[0292] R in Formula 201 109 Can be:

[0293] phenyl, naphthyl, anthracenyl, or pyridyl; or

[0294] Phenyl, naphthyl, anthracenyl, or pyridyl, 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 20 Alkyl, C 1 -C 20 Alkoxy, C 1 -C 20 alkylthio, phenyl, naphthyl, anthracenyl, pyridyl, or a combination thereof.

[0295] According to one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A, but the embodiment is not limited thereto:

[0296] Formula 201A

[0297]

[0298] R in Formula 201A 101 , R 111 , R 112 , and R 109 Each is as described herein.

[0299] 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 shown below, but the embodiment is not limited thereto:

[0300]

[0301]

[0302] 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 hole injection layer may have a thickness of about -about For example, about -about And the thickness of the hole transport layer may be about -about For example, about -about Without wishing to be bound by theory, 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.

[0303] In addition to these materials, the hole transport region may further include a charge generating material for improving the conductive property. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0304] The charge generating material may be, for example, a p-dopant. The p-dopant may be one of the following: a quinone derivative, a metal oxide, or a compound containing a cyano group, but the embodiment is not limited thereto. For example, non-limiting examples of the p-dopant include quinone derivatives such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), 1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (F6-TCNNQ), etc.; metal oxides such as tungsten oxide, molybdenum oxide, etc.; or a compound containing a cyano group, such as one of compounds HT-D1 or F12, but the embodiment is not limited thereto:

[0305]

[0306] The hole transport region may include a buffer layer.

[0307] 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 the light emitting device may be improved.

[0308] Meanwhile, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be selected from the materials for the hole transport region described above and the materials for the host to be described later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be mCP, which will be described later.

[0309] Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emission layer is formed by vacuum deposition or spin coating, deposition or coating conditions may be similar to those applied when forming the hole injection layer, although deposition or coating conditions may vary depending on the material used to form the emission layer.

[0310] The emission layer may include a host and a dopant, and the dopant may include at least one of the organic metal compounds represented by Formula 1.

[0311] The host may include at least one of the following: 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'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 1,3,5-tri(carbazolyl-9-yl)benzene (TCP), 1,3-bis(N-carbazolyl)benzene (mCP), compound H50, or compound H51, but embodiments are not limited thereto:

[0312]

[0313] In one or more embodiments, the host may include a compound represented by Formula 301, but the embodiments are not limited thereto:

[0314] Formula 301

[0315]

[0316] Ar in Formula 301 111 and Ar 112 Can be independently:

[0317] Phenylene, naphthylene, phenanthrenyl, or pyrenylene; or

[0318] Phenylene, naphthylene, phenanthrenylene, or pyrenylene, each substituted with at least one of phenyl, naphthyl, anthracenyl, or a combination thereof.

[0319] Ar in Formula 301 113 -Ar 116 Can be independently:

[0320] C is unsubstituted or substituted with at least one of the following 1 -C 10 Alkyl: phenyl, naphthyl, anthracenyl, or a combination thereof;

[0321] Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl;

[0322] Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl, each substituted with 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, fluorenyl, or a combination thereof; or

[0323] A group represented by the formula:

[0324]

[0325] However, the embodiments are not limited thereto.

[0326] Ar in Formula 301 113 -Ar 116 Can be independently:

[0327] C 1 -C 10 alkyl, phenyl, naphthyl, phenanthrenyl, or pyrenyl; or

[0328] Phenyl, naphthyl, phenanthrenyl, or pyrenyl, each substituted with at least one of phenyl, naphthyl, anthracenyl, or a combination thereof.

[0329] In Formula 301, g, h, i, and j may each independently be an integer of 0-4, and g, h, i, and j may each independently be, for example, 0, 1, or 2.

[0330] In one or more embodiments, the host may include a compound represented by Formula 302, but the embodiments are not limited thereto:

[0331] Formula 302

[0332]

[0333] Ar in formula 302 122 -Ar 125 For example, regarding Ar in Formula 301 113 Described in detail.

[0334] Ar in formula 302 126 and Ar 127 Can be independently C 1 -C 10 Alkyl (eg, methyl, ethyl, or propyl).

[0335] 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.

[0336] When the organic light emitting device 10 is a full-color organic light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer. In one or more embodiments, due to the stacked structure including the red emission layer, the green emission layer, and / or the blue emission layer, the emission layer may emit white light.

[0337] When the emission layer includes a host and a dopant, an amount of the dopant may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but the embodiment is not limited thereto.

[0338] The thickness of the emission layer may be about -about For example, about -about Without wishing to be bound by theory, when the thickness of the emission layer 15 is within these ranges, excellent light emitting characteristics may be obtained without a significant increase in driving voltage.

[0339] An electron transport region may be located on the emission layer.

[0340] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0341] 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, and 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.

[0342] The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region may be understood by referring to the conditions for forming the hole injection layer.

[0343] 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:

[0344]

[0345] The thickness of the hole blocking layer may be about -about For example, about -about Without wishing to be bound by theory, 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.

[0346] The electron transport layer may 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-hydroxy-quinoline)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), but the embodiments are not limited thereto:

[0347]

[0348] In one or more embodiments, the electron transport layer may include at least one of ET1 to ET25, but the embodiments are not limited thereto:

[0349]

[0350]

[0351] The thickness of the electron transport layer may be about -about For example, about -about Without wishing to be bound by theory, 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.

[0352] The electron transport layer may further include a material containing a metal in addition to the materials as described above.

[0353] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (8-hydroxyquinoline lithium, LiQ) or ET-D2:

[0354]

[0355] The electron transport region may include an electron injection layer that facilitates the flow of electrons from the second electrode 19 thereinto.

[0356] The electron injection layer may include compounds ET-D1, LiF, NaCl, CsF, Li 2 O, BaO, or a combination thereof.

[0357] The thickness of the electron injection layer may be about -about and for example about -about Without wishing to be bound by theory, when the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a significant increase in driving voltage.

[0358] The second electrode 19 is located 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, lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as the material for forming the second electrode 19. In one or more embodiments, in order to manufacture a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0359] In the above, reference has been made to Figure 1 The organic light emitting device is described, but the embodiment is not limited thereto.

[0360] On the other hand, an electronic device including the organic light-emitting device is provided. In addition to the organic light-emitting device as described herein, the electronic device may further include a thin film transistor (TFT). The thin film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the organic light-emitting device, but the embodiment is not limited thereto.

[0361] Another aspect provides a diagnostic composition comprising at least one organometallic compound represented by Formula 1.

[0362] The organometallic compound represented by Formula 1 provides high luminescence efficiency. Therefore, a diagnostic composition including at least one of the organometallic compounds represented by Formula 1 may have high diagnostic efficiency.

[0363] The diagnostic composition may be used in various applications including diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc., but the embodiments are not limited thereto.

[0364] 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 non-limiting examples thereof include 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.

[0365] As used herein, the term "C 1 -C 60 "Alkoxy" refers to a 101 (A 101 C 1 -C 60 The term "C alkyl" as used herein is a monovalent group represented by an alkyl group, and non-limiting examples thereof include methoxy, ethoxy, isopropoxy, and the like. 1 -C 60 "Alkylthio" refers to -SA 101 (A 101 C 1 -C 60 A monovalent group represented by an alkyl group.

[0366] 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 non-limiting examples thereof include vinyl, propenyl, butenyl, etc. 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0367] 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 non-limiting examples thereof include 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.

[0368] As used herein, the term "C 3 -C10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms as ring atoms, and non-limiting examples thereof include 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 as ring atoms, and non-limiting examples thereof include 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.

[0369] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent saturated ring group having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring-forming atom and 1 to 10 carbon atoms as ring-forming atoms, and non-limiting examples thereof include 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.

[0370] As used herein, the term "C 3 -C 10 The term "cycloalkenyl" as used herein refers to a monovalent cyclic group which includes 3 to 10 carbon atoms as ring atoms and at least one carbon-carbon double bond in its ring and does not have aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like. 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0371] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl" refers to a monovalent cyclic group having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring atom, 1 to 10 carbon atoms as ring atoms and at least one double bond in its ring and having no aromaticity. 1 -C 10 Non-limiting examples of heterocycloalkenyl include 2,3-dihydrofuranyl, 2,3-dihydrothienyl, and the like. As used herein, the term “C 2 -C 10 "Heterocycloalkenylene" refers to a 2 -C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0372] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic ring 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 ring system having 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include 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 rings may be fused to each other.

[0373] As used herein, the term "C 7 -C 60 "Alkylaryl" refers to a 1 -C 54 Alkyl substituted C 6 -C 59 Aryl. As used herein, the term "C 7 -C 60 "Arylalkyl" refers to a 6 -C 59 Aryl substituted C 1 -C 54 alkyl.

[0374] As used herein, the term "C 1 -C 60 The term "heteroaryl" refers to a monovalent group having a heterocyclic aromatic ring system having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring atom and 1 to 60 carbon atoms as ring atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic ring system having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring atom and 1 to 60 carbon atoms as ring atoms. 1 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, and the like. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.

[0375] As used herein, the term "C 2 -C 60 "Alkylheteroaryl" refers to a 1 -C 59 Alkyl substituted C 1 -C 59 As used herein, the term "C 2 -C 60 "Heteroarylalkyl" refers to a 1 -C 59 Heteroaryl-substituted C 1 -C 59 alkyl.

[0376] 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).

[0377] As used herein, the term "C 1 -C 60 "Heteroaryloxy" refers to -OA 104 (A 104 C 1 -C 60 heteroaryl), and as used herein, the term "C 1 -C 60 "Heteroarylthio" refers to -SA 105 (A 105 C 1 -C 60 heteroaryl).

[0378] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8-60 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. Non-limiting examples of monovalent non-aromatic fused polycyclic groups include 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.

[0379] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 1-60 carbon atoms) having two or more rings fused to each other, having a heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring-forming atom in addition to carbon atoms, and having no aromaticity in terms of its entire molecular structure. Non-limiting examples of monovalent non-aromatic fused heteropolycyclic groups include 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.

[0380] As used herein, the term "C 5 -C 30 The term "carbocyclic group" refers to a saturated or unsaturated ring 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.

[0381] As used herein, the term "C 1 -C 30 The term "heterocyclic group" refers to a saturated or unsaturated ring group including 1 to 30 carbon atoms and at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as ring atoms. 1 -C 30 The heterocyclic group may be a monocyclic group or a polycyclic group.

[0382] 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 C7 -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:

[0383] Deuterium, -F, -Cl, -Br, -I, -SF 5 、-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, or C 1 -C 60 Alkylthio;

[0384] 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, -SF 5 、-CD 3 、-CD2 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 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q 16 )(Q 17 )、-P(Q 18 )(Q 19 )、-P(=O)(Q 18 )(Q 19 ), or a combination thereof;

[0385] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60Aryl, 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;

[0386] 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, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group, and 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, 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 -C60 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 )(Q 22 )(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

[0387] -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q36 )(Q 37 )、-P(Q 38 )(Q 39 ), or -P(=O)(Q 38 )(Q 39 ),and

[0388] 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, 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 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.

[0389] For example, Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 Can be independently:

[0390] 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, or C each of which is unsubstituted or substituted by at least one of the following 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, C1 -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, C 3 -C 10 Cycloalkyl, C 6 -C 60 aryl, or a combination thereof.

[0391] Hereinafter, the organic metal compound represented by Formula 1 and the organic light-emitting device including the organic metal compound represented by Formula 1 according to the exemplary embodiment are further described in detail with reference to the Synthesis Examples and Examples. However, the organic metal 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 the amount of A used is the same as the amount of B used on a molar equivalent basis.

[0392] Example

[0393] Synthesis Example 1: Synthesis of Compound 13

[0394]

[0395] Synthesis of compound 13A

[0396] 2-Phenyl-5-(trimethylgermyl)pyridine (3.0 g, 11.03 mmol) and iridium chloride trihydrate (IrCl 3 (H 2 O) n , n=3, the same below) (1.87 g, 5.3 mmol) was mixed with 90 milliliters (mL) of 2-ethoxyethanol and 30 mL of deionized (DI) water, and the mixed solution was stirred and heated under reflux for 24 hours. Then, the temperature of the product was lowered to room temperature. The resulting solid was separated by filtration, washed thoroughly with water, methanol, and hexane in the order stated, and then dried in a vacuum oven to obtain 3.1 g (76% yield) of compound 13A.

[0397] Synthesis of compound 13B

[0398] Compound 13A (3.1g, 2.01mmol) is mixed with 120mL dichloromethane (DCM), and then a mixture of silver trifluoromethanesulfonate (AgOTf) (1.09g, 4.23mmol) in 40mL methanol (MeOH) is added thereto. Afterwards, the resulting reaction mixture is stirred at room temperature for 18 hours while blocking light with aluminum foil. The product is then filtered through diatomite to remove solids. The filtrate is then subjected to decompression to obtain a solid (compound 13B), which is used in the following reaction without additional purification processes.

[0399] Synthesis of compound 13

[0400] Compound 13B (2.8 g, 2.96 mmol) and 2-(12,12-dimethyl-12H-benzo[b]benzo[4,5]thiorrolo[3,2-g]benzofuran-10-yl)-4-(methyl-d3)pyridine (1.28 g, 3.24 mmol) were mixed with 30 mL of 2-ethoxyethanol and 30 mL of dimethylformamide (DMF), and the mixed solution was stirred at 120 ° C for 24 hours. Then, the temperature of the solution was lowered to room temperature. The solvent was removed under reduced pressure, and the resulting solid was purified by column chromatography (eluent: hexane and ethyl acetate) to obtain 0.95 g of compound 13 (28% yield). The obtained compound was confirmed by high resolution mass spectrometry (HRMS (MALDI)) using matrix-assisted laser desorption ionization and high performance liquid chromatography (HPLC) analysis.

[0401] HRMS (MALDI): For C 54 H 49 D 3 Ge 2 Ir 3 Calculated value for OSi: m / z 1130.2121; found: 1130.2124.

[0402] 2-(12,12-Dimethyl-12H-benzo[b]benzo[4,5]thiorrolo[3,2-g]benzofuran-10-yl)-4-(methyl-d3)pyridine was synthesized according to the following reaction scheme. The yield of the compound is as described in the scheme.

[0403]

[0404] Synthesis Example 2: Synthesis of Compound 19

[0405]

[0406] Synthesis of compound 19

[0407] 0.84 g of compound 19 (yield of 28%) was obtained in a similar manner to that used to synthesize compound 13 in Synthesis Example 1, except that 2-(11,11-dimethyl-11H-benzo[b]benzo[4,5]thiorrolo[2,3-f]benzofuran-4-yl)-4-(methyl-d3)pyridine was used instead of 2-(12,12-dimethyl-12H-benzo[b]benzo[4,5]thiorrolo[3,2-g]benzofuran-10-yl)-4-(methyl-d3)pyridine. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0408] HRMS (MALDI): For C 54 H 49 D 3 Ge 2 Ir 3 Calculated value for OSi: m / z 1130.2121; found: 1130.2123.

[0409] 2-(11,11-Dimethyl-11H-benzo[b]benzo[4,5]thiorrolo[2,3-f]benzofuran-4-yl)-4-(methyl-d3)pyridine was synthesized according to the following reaction scheme. The yield of the compound is as described in the scheme.

[0410]

[0411] Synthesis Example 3: Synthesis of Compound 25

[0412]

[0413] Synthesis of compound 25

[0414] Compound 25B was obtained in a similar manner to that used to synthesize Compound 13B in Synthesis Example 1, except that 2-phenyl-5-(trimethylsilyl)pyridine was used instead of 2-phenyl-5-(trimethylgermyl)pyridine. Then, 0.75 g of Compound 25 (25% yield) was obtained in a similar manner to that used to synthesize Compound 13 in Synthesis Example 1, except that Compound 25B was used instead of Compound 13B, and 2-(12,12-dimethyl-12H-benzo[b]benzo[4,5]thiorrolo[3,2-g]benzofuran-10-yl)-4,5-bis(methyl-d3)pyridine was used instead of 2-(12,12-dimethyl-12H-benzo[b]benzo[4,5]thiorrolo[3,2-g]benzofuran-10-yl)-4-(methyl-d3)pyridine. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0415] HRMS (MALDI): For C 55 H 48 D 6 Ir 3 OSi 3 Calculated for: m / z 1055.3581; found: 1055.3578.

[0416] 2-(12,12-Dimethyl-12H-benzo[b]benzo[4,5]thiorrolo[3,2-g]benzofuran-10-yl)-4,5-bis(methyl-d3)pyridine was synthesized according to the following reaction scheme. The yield of the compound is as described in the scheme.

[0417]

[0418] Synthesis Example 4: Synthesis of Compound 31

[0419]

[0420] Synthesis of compound 31

[0421] Compound 31B was obtained in a similar manner to that used to synthesize Compound 13B in Synthesis Example 1, except that 2-phenyl-5-(trimethylsilyl)pyridine was used instead of 2-phenyl-5-(trimethylgermyl)pyridine. Then, 0.68 g of Compound 31 (24% yield) was obtained in a similar manner to that used to synthesize Compound 13 in Synthesis Example 1, except that Compound 31B was used instead of Compound 13B, and 2-(11,11-dimethyl-11H-benzo[b]benzo[4,5]thiorrolo[2,3-f]benzofuran-4-yl)-4,5-bis(methyl-d3)pyridine was used instead of 2-(12,12-dimethyl-12H-benzo[b]benzo[4,5]thiorrolo[3,2-g]benzofuran-10-yl)-4-(methyl-d3)pyridine. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0422] HRMS (MALDI): For C 55 H 48 D 6 Ir 3 OSi 3 Calculated for: m / z 1055.3581; found: 1055.3578.

[0423] 2-(11,11-Dimethyl-11H-benzo[b]benzo[4,5]thiorrolo[2,3-f]benzofuran-4-yl)-4,5-bis(methyl-d3)pyridine was synthesized according to the following reaction scheme. The yield of the compound is as described in the scheme.

[0424]

[0425] Example 1

[0426] 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.

[0427] Compound HT3 and F12-P-dopant were co-deposited on the anode in a weight ratio of 98:2 by vacuum 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 .

[0428] Then, compound GH3 (host) and compound 13 (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.

[0429] Afterwards, compound ET3 and Liq-N-dopant were co-deposited on the emission layer in a volume ratio of 50:50 by vacuum deposition to form a An electron transport layer having a thickness of , and a Liq-N-dopant 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 provided, thereby completing the manufacture of the organic light-emitting device.

[0430]

[0431] Examples 2-4 and Comparative Examples 1-9

[0432] Organic light-emitting devices were manufactured in a similar manner to that in Example 1, except that the compounds shown in Table 2 were each used instead of Compound 13 when forming the emission layer.

[0433] Evaluation Example 1: Characterization of organic light-emitting devices

[0434] The driving voltage (volt, V), maximum external quantum efficiency (Max EQE, %), maximum emission wavelength (nm), and lifetime (LT) of the organic light-emitting devices of Examples 1-4 and Comparative Examples 1-9 were evaluated. 97 , %), 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 6000 candela / m2 (cd / m 2 ) was evaluated as the time taken for the luminance to decrease to 97% of the initial luminance (100%), and the life value is shown as a relative value (relative %) relative to Comparative Example 1.

[0435] Table 2

[0436]

[0437]

[0438]

[0439]

[0440] As can be confirmed from Table 2, the organic light emitting devices of Examples 1 to 4 have low driving voltage, high maximum external quantum efficiency, and long lifetime.

[0441] It can also be confirmed from Table 2 that, compared with the organic light-emitting devices of Comparative Examples 1-9, the organic light-emitting devices of Examples 1-4 have lower driving voltage, higher maximum external quantum efficiency, and significantly improved lifespan.

[0442] Since the organometallic compound represented by Formula 1 has excellent electrical properties, an electronic device such as an organic light-emitting device using at least one of the organometallic compounds represented by Formula 1 may have a low driving voltage, excellent external quantum efficiency, and a long life. Therefore, by using at least one of the organometallic compounds represented by Formula 1, a high-quality organic light-emitting device may be realized.

[0443] It should be understood that the exemplary embodiments described herein should be considered in a descriptive sense 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 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 Formula 1: <h2 style=";text-align:left;direction:ltr">M1(L1)<h2 style=";text-align:left;direction:ltr"> n1 <h2 style=";text-align:left;direction:ltr"> (L2)<h2 style=";text-align:left;direction:ltr"> n2 in, In formula 1, M1 is a transition metal, L1 is a ligand represented by Formula 1A, L2 is a ligand represented by Formula 1B, and n1 and n2 are each independently 1 or 2, Formula 1A Formula 1B Formula 2 Wherein, in Formulas 1A, 1B, and 2, X1 is C or N, X2 is C or N, X3 is C or N, X4 is C or N, Ring CY1, ring CY2, and ring CY5 are each independently C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, Ring CY3 is (i) a 6-membered carbocyclic group, (ii) a 6-membered heterocyclic group, (iii) 30 A 6-membered carbocyclic group fused to a carbocyclic group, or a C1-C 30 a 6-membered carbocyclic group fused to a heterocyclic group, or (iv) a C5-C 30 A 6-membered heterocyclic group fused to a carbocyclic group, or a C1-C 30 a 6-membered heterocyclic group fused to a heterocyclic group, Z1 and Z2 are each independently -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3), a1 and a2 are each independently an integer of 0-10, The sum of a1 and a2 is 1 or greater, X 41 C(R 41 ) or N, X 42 C(R 42 ) or N, X 43 C(R 43 ), N, or C bonded to Y3 in Formula 2; X 44 C(R 44 ), N, or C bonded to Y2 or Y3 in Formula 2; X 45 C(R 45 ), N, or C bonded to Y2 or Y3 in Formula 2; and X 46 C(R 46 ), N, or C bonded to Y2 in Formula 2, The condition is, i) X 43 is C bonded to Y3 in Formula 2, and X 44 is C bonded to Y2 in Formula 2; ii) X 44 is C bonded to Y3 in Formula 2, and X 45 is C bonded to Y2 in Formula 2; or iii) X 45 is C bonded to Y3 in Formula 2, and X 46 is C bonded to Y2 in Formula 2, Y1 is O, S, Se, B (R 61 )、N(R 61 ), or C(R 61 )(R 62 ), Y2 is a single bond, O, S, Se, B (R 63 )、N(R 63 )、C(R 63 )(R 64 )、Si(R 63 )(R 64 ), or Ge(R 63 )(R 64 ), Y3 is a single bond, O, S, Se, B (R 65 )、N(R 65 )、C(R 65 )(R 66 )、Si(R 65 )(R 66 ), or Ge(R 65 )(R 66 ), At least one of conditions 1 and 2 must be met: Condition 1 Y2 is Si(R 63 )(R 64 ) or Ge(R 63 )(R 64 ), Condition 2 Y3 is Si(R 65 )(R 66 ) or Ge(R 65 )(R 66 ), R1-R3, R5, R 41 -R 46 , and R 61 -R 66 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, 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 C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 heteroarylthio, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(═O)(Q8)(Q9), Two or more adjacent R1 groups are optionally bonded together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups, Two or more adjacent R2 groups are optionally bonded together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups, b1-b3 and b5 are each independently an integer of 1-10, In Formulas 1A and 1B, * and *' each represent a binding site with M1, In Formula 2, * and *' each represent a binding site with an adjacent atom, Substituted C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 Substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, 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, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio; C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, 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, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 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; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, 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, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(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 -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 Q1-Q9, Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, 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 C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-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.

2. The organometallic compound of claim 1, wherein M1 is iridium, platinum, osmium, palladium, gold, titanium, zirconium, hafnium, europium, terbium, thulium, or rhodium.

3. The organometallic compound according to claim 1, wherein M1 is Ir, and The sum of n1 and n2 is 3.

4. The organometallic compound of claim 1 , wherein ring CY1 and ring CY2 are each independently a benzene group, a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

5. The organometallic compound according to claim 1, wherein ring CY3 and ring CY5 are each independently a benzene group, a naphthyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

6. The organometallic compound according to claim 1, wherein in Formula 1A The moiety represented by is a group represented by one of the formulae CY(1)-1 to CY(1)-32: in, In formulae CY(1)-1 to CY(1)-32, R 11 -R 14 Each independently as described in claim 1 with respect to R1, provided that R 11 -R 14 Not hydrogen, Z1 as described in claim 1, * indicates the binding site with M1, and *” indicates the binding site with the adjacent atoms.

7. The organometallic compound according to claim 1, wherein in Formula 1A The moiety represented by is a group represented by one of the formulae CY(2A)-1 to CY(2A)-16: in, In formulae CY(2A)-1 to CY(2A)-16, R 21 -R 24 Each independently as described in claim 1 with respect to R2, provided that R 21 -R 24 Not hydrogen, *' indicates the binding site with M1, and *” indicates the binding site with the adjacent atoms.

8. The organometallic compound as claimed in claim 1, wherein in Formula 1B The moiety represented by is a group represented by one of the formulae CY(3)-1 to CY(3)-16: in, In formulae CY(3)-1 to CY(3)-16, R 31 -R 34 Each independently as described in claim 1 with respect to R3, provided that R 31 -R 34 Not hydrogen, * indicates the binding site with M1, and *” indicates the binding site with the adjacent atoms.

9. The organometallic compound of claim 1, wherein one of Y2 or Y3 is a single bond.

10. The organometallic compound of claim 1, wherein L1 is a ligand represented by Formula 1A-1: in, In Formula 1A-1, X1 is C or N, X2 is C or N, X 11 C(R 11 ) or N, X 12 C(R 12 ) or N, X 13 C(R 13 ) or N, X 14 C(R 14 ) or N, X 21 C(R 21 ) or N, X 22 C(R 22 ) or N, X 23 C(R 23 ) or N, X 24 C(R 24 ) or N, R 11 -R 14 Each independently as described in claim 1 regarding R1, R 21 -R 24 Each independently as described in claim 1 regarding R2, R 11 -R 14 and R 21 -R 24 At least one of each is independently -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3), wherein Q1-Q3 are each as described in claim 1, and * and *' each indicate a binding site to M1.

11. The organometallic compound of claim 1, wherein L2 is a ligand represented by one of Formulas 1B-1 to 1B-3: in, In Formulae 1B-1 to 1B-3, CycloCY3, CycloCY5, X 41 -X 46 , Y1-Y3, R3, b3, R5, and b5 are each as described in claim 1, and * and *' each indicate a binding site to M1.

12. The organometallic compound according to claim 1, wherein L2 is a ligand represented by one of formulas 1B(1)-1 to 1B(1)-6: in, In Formulae 1B(1)-1 to 1B(1)-6, CycloCY3,X 41 -X 46 , Y1-Y3, R3, and b3 are each as described in claim 1, X 51 C(R 51 ) or N, X 52 C(R 52 ) or N, X 53 C(R 53 ) or N, X 54 C(R 54 ) or N, R 51 -R 54 Each independently as described in claim 1 regarding R5, and * and *' each indicate a binding site to M1.

13. The organometallic compound according to claim 1, wherein R1-R3, R5, R 41 -R 46 , and R 61 -R 66 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, 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, C1-C 20 Alkyl, C1-C 20 Alkoxy, or C1-C 20 Alkylthio; C1-C 20 Alkyl, C1-C 20 Alkoxy, or C1-C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, 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, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, or a combination thereof; Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl; cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl , oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, or imidazopyrimidyl: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, 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, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or a combination thereof; or -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=O)(Q8)(Q9), and Q1-Q9 are each independently: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of: deuterium, C1-C 10 Alkyl, phenyl, or a combination thereof.

14. The organometallic compound according to claim 1, wherein the organometallic compound is represented by one of Formulas 5-1 to 5-6: in, In formulas 5-1 to 5-6, M1, n1, n2, X 41 -X 46 , and Y1-Y3 are each as described in claim 1, X 11 C(R 11 ) or N, X 12 C(R 12 ) or N, X 13 C(R 13 ) or N, X 14 C(R 14 ) or N, X 21 C(R 21 ) or N, X 22 C(R 22 ) or N, X 23 C(R 23 ) or N, X 24 C(R 24 ) or N, X 31 C(R 31 ) or N, X 32 C(R 32 ) or N, X 33 C(R 33 ) or N, X 34 C(R 34 ) or N, X 51 C(R 51 ) or N, X 52 C(R 52 ) or N, X 53 C(R 53 ) or N, X 54 C(R 54 ) or N, R 11 -R 14 Each independently as described in claim 1 regarding R1, R 21 -R 24 Each independently as described in claim 1 regarding R2, R 11 -R 14 and R 21 -R 24 At least one of each is independently -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3), wherein Q1-Q3 are each the same as described in claim 1, R 31 -R 34 Each independently as described in claim 1 with respect to R3, and R 51 -R 54 Each independently as described in claim 1 regarding R5.

15. The organometallic compound of claim 1, wherein the organometallic compound is represented by one of Compounds 1 to 128:

16. 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 of the organometallic compounds according to any one of claims 1 to 15.

17. The organic light emitting device of claim 16, wherein the emissive layer comprises the at least one of the organometallic compounds. 18 . The organic light emitting device of claim 16 , wherein the emission layer emits green light having a maximum emission wavelength of 490 nm to 550 nm.

19. The organic light emitting device according to claim 16, wherein The first electrode is an anode, The second electrode is a cathode, The organic layer further comprises: 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.

20. An electronic device comprising the organic light emitting device according to any one of claims 16 to 19.

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