Organometal compound, organic light emitting device including organometal compound, and electronic

Abstract

Disclosed are an organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic device including the organic light-emitting device. The organometallic compound is represented by Formula 1: wherein, in Formula 1, M1 is a transition metal, Ln1 is a ligand represented by Formula 1A, Ln2 is a ligand represented by Formula 1B, and n1 and n2 are each independently 1 or 2, where, in Formulae 1A and 1B, Ar1 and Ar2 are each independently a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, L1 is O, S, Se, N (R54), or C (R55) (R56), and n is an integer of 1 or more. And the remaining groups and variables are as defined herein.

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefits to Korean Patent Application No. 10-2024-0120955, filed on September 5, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This disclosure relates to organometallic compounds, organic light-emitting devices including said organometallic compounds, and electronic devices including said organic light-emitting devices. Background Technology

[0004] Organic light-emitting devices (OLEDs) are self-emitting devices with excellent characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed. In addition, OLEDs can produce full-color images.

[0005] A typical organic light-emitting device includes an anode, a cathode, and an organic layer comprising an emission layer disposed between the anode and cathode. 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 supplied from the anode can move towards the emission layer through the hole transport region, and electrons supplied from the cathode can move towards the emission layer through the electron transport region. Holes and electrons recombine in the emission layer to generate excitons. When an exciton transitions from an excited state to the ground state, light is emitted. Summary of the Invention

[0006] The invention provides an organometallic compound, an organic light-emitting device comprising the organometallic compound, and an electronic device comprising the organic light-emitting device.

[0007] Additional aspects will be set forth in part in the following detailed description, and will be apparent in part from that detailed description, or may be learned through practice of the exemplary embodiments presented herein.

[0008] According to one aspect, organometallic compounds represented by Formula 1 are provided:

[0009] Formula 1

[0010] M1(L n1 ) n1 (L n2 ) n2

[0011] In Equation 1,

[0012] M1 is a transition metal.

[0013] L n1 For the ligand represented by Equation 1A,

[0014] L n2 For the ligand represented by Equation 1B, and

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

[0016] Formula 1A

[0017]

[0018] Formula 1B

[0019]

[0020] Among them, in equations 1A and 1B,

[0021] X1 is C or N, X2 is C or N, X3 is C or N, and X4 is C or N.

[0022] Cycle CY1 and Cycle CY2 are each independently C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups,

[0023] Cyclic CY4 is a 6-membered carbon ring group or a 6-membered heterocyclic group.

[0024] Y1 represents O, S, Se, N(R) 51 ), or C(R) 52 (R) 53 ),

[0025] Ar1 and Ar2 are independently substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,

[0026] a1 and a2 are each independent integers from 1 to 3.

[0027] L1 is O, S, Se, N (R 54 ), or C(R) 55 (R) 56 ),

[0028] m1 is an integer from 1 to 3.

[0029] R1 to R4, R 40 and R 51 To R 56 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, 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 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, 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 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=O)(Q8)(Q9),

[0030] Two or more adjacent R1s are optionally bonded to each other to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,

[0031] Two or more adjacent R2 molecules are optionally bonded to each other to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,

[0032] Two or more adjacent R3s are optionally bonded to each other to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,

[0033] Multiple R 40Two or more adjacent C5-C molecules are optionally bonded to each other to form substituted or unsubstituted C5-C molecules. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,

[0034] b1 and b2 are each independent integers from 1 to 10.

[0035] b3 is an integer from 1 to 3.

[0036] b4 is either 1 or 2.

[0037] b40 is an integer from 1 to 4.

[0038] * and *' each represent the binding site with M1.

[0039] Replacement 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 Alkyne group, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, 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 Heteroaryl groups, substituted C1-C 60 The heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of the substituted monovalent non-aromatic fused heterocyclic group are each independently:

[0040] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio,

[0041] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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,

[0042] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups,

[0043] Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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

[0044] -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

[0045] Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, 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 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10Heterocyclic alkenyl, 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 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

[0046] On the other hand, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emitting layer, and wherein the organic layer comprises at least one organometallic compound represented by Formula 1.

[0047] On the other hand, it provides electronic devices that include the organic light-emitting device. Attached Figure Description

[0048] By combination Figure 1 The above and other aspects, features and advantages of some exemplary embodiments will become clearer from the following detailed description. Figure 1 This is a schematic diagram of an organic light-emitting device according to one or more embodiments. Detailed Implementation

[0049] Exemplary embodiments will now be described in further detail, examples of which are shown in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the specification. In this respect, the embodiments may take different forms and should not be construed as limited to the detailed description set forth herein. Therefore, embodiments are described in further detail below, and with reference to the accompanying drawings, only to illustrate certain aspects and features. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. Expressions such as “at least one of” modify the entire list of elements when preceding or following it, without modifying any individual element of the list.

[0050] The terminology used herein is for the purpose of describing one or more exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms “a” and “the” are also intended to include the plural forms unless the context clearly indicates otherwise. The term “or” means “and / or”. It will be further understood that the terms “comprising” or “including” as used in this specification indicate the presence of the stated features, regions, integrals, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more additional features, regions, integrals, steps, operations, elements, components, and / or sets thereof.

[0051] It will be understood that although the terms first, second, third, etc., may be used herein to describe various elements, components, regions, layers, and / or portions, these elements, components, regions, layers, and / or portions should not be limited by these terms. These terms are used only to distinguish one element, component, region, layer, or portion from another. Therefore, without departing from the teachings of this embodiment, the first element, component, region, layer, or portion discussed below may be referred to as the second element, component, region, layer, or portion.

[0052] Exemplary embodiments are described herein with reference to cross-sectional views, which are schematic diagrams of idealized embodiments. Thus, deviations from the shapes shown in the figures will be anticipated as a result of, for example, manufacturing techniques and / or tolerances. Therefore, the embodiments described herein should not be construed as limited to the specific shapes of the regions illustrated herein, but rather include deviations in shape caused, for example, by manufacturing processes. For example, regions illustrated or described as flat may typically have rough and / or non-linear characteristics. Furthermore, sharp corners in the figures 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.

[0053] It will be understood that when an element is referred to as being "on" another element, it may be in direct contact with the other element or there may be an intermediate element between them. Conversely, when an element is referred to as being "directly on" another element, there is no intermediate element.

[0054] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having meanings consistent with their meanings in the context of this disclosure and the relevant field, and will not be interpreted in an idealized or overly formal sense unless expressly defined herein.

[0055] As used herein, “about” or “approximately” includes the stated value and means within an acceptable range of deviations from the specific 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 specific quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations relative to the stated value, or within ±10% or 5%.

[0056] According to one aspect, organometallic compounds are represented by Formula 1:

[0057] Formula 1

[0058] M1(L n1 ) n1 (L n2 ) n2

[0059] In Equation 1, M1 is a transition metal.

[0060] For example, M1 can be a transition metal in the first row of the periodic table, a transition metal in the second row of the periodic table, or a transition metal in the third row of the periodic table.

[0061] In one or more embodiments, M1 may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0062] In one or more embodiments, M1 may be Ir, Pt, Os, or Rh.

[0063] In one or more embodiments, M1 may be Ir.

[0064] In Equation 1, n1 is 1 or 2, and n2 is 1 or 2.

[0065] In one or more embodiments, the sum of n1 and n2 can be 2 or 3.

[0066] In one or more embodiments, M1 may be Ir, and the sum of n1 and n2 may be 3.

[0067] In one or more embodiments, M1 may be Pt, and the sum of n1 and n2 may be 2.

[0068] L in Formula 1 n1 For the ligand represented by Equation 1A:

[0069] Formula 1A

[0070] .

[0071] In Equation 1A, X1 is C or N, and X2 is C or N.

[0072] In one or more embodiments, X1 may be N, and X2 may be C.

[0073] In Equation 1A, rings CY1 and CY2 are each independently C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups.

[0074] In one or more embodiments, ring CY1 and ring CY2 may each independently be i) a first ring, ii) a second ring, iii) a fused ring group in which at least two first rings are fused together, iv) a fused ring group in which at least two second rings are fused together, or v) a fused ring group in which at least one first ring is fused with at least one second ring.

[0075] The first ring can be a cyclopentyl group, a cyclopentadienyl group, a furan group, a thiophene group, a pyrrole group, a thiophene group, an indole group, a benzofuran group, a benzothiophene group, an indole group, or a benzothiophene group. azole group, iso- azole group, diazole group, isodiazole group diazole group, Triazole group, isotriazole group Triazole group, thiazole group, isothiazole group, thiadiazole group, isothiazole group, thiatriazole group, isothiazole group, pyrazole group, imidazole group, triazole group, tetraazole group, azathiophene group, diazathiophene group, or triazathiophene group, and

[0076] The second ring can be an adamantyl group, norbornel group, norbornene group, cyclohexyl group, cyclohexene group, phenyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group.

[0077] In one or more embodiments, ring CY1 and ring CY2 may each independently be a phenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenanthrene group, a pyridine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthrene group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene group, an azirfluorene group, an azircarbazole group, an azirdibenzofuran group, an azirdibenzothiophene group, or an azirdibenzothiophene group.

[0078] In one or more embodiments, cycloCY1 may be a pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, or quinazoline group.

[0079] In one or more embodiments, cycloCY2 may be a phenyl group or a naphthalene group.

[0080] In one or more embodiments, the formula 1A is derived from... The represented part can be a group represented by one of the formulas CY(1)-1 to CY(1)-16:

[0081]

[0082] .

[0083] In equations CY(1)-1 to CY(1)-16,

[0084] R 11 To R 14 Each independently as described with respect to R1, the condition being R 11 To R 14 It cannot be hydrogen.

[0085] * indicates the binding site with M1, and

[0086] * indicates a binding site with an adjacent atom.

[0087] For example, R in equations CY(1)-1 to CY(1)-16 11 To R 14 Each can be independently classified as deuterium, C1-C. 10 Alkyl groups (e.g., -CH3, -CH2CH3, etc.), C1-C substituted with at least one deuterium 10 Alkyl groups (e.g., -CD3, -CD2H, -CDH2, etc.), -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3). In -Si(Q1)(Q2)(Q3) and -Ge(Q1)(Q2)(Q3), Q1 to Q3 can each be independently:

[0088] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0089] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0090] Each of the following is replaced by n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10Alkyl, phenyl, or combinations thereof.

[0091] In one or more embodiments, the formula 1A is derived from... The represented part can be a group represented by one of the formulas CY(2)-1 to CY(2)-16:

[0092]

[0093] .

[0094] In equations CY(2)-1 to CY(2)-16,

[0095] R 21 To R 24 Each independently as described with respect to R2, the condition being R 21 To R 24 None of them could be hydrogen.

[0096] *' indicates the binding site with M1, and

[0097] * indicates a binding site with an adjacent atom.

[0098] For example, R in equations CY(2)-1 to CY(2)-16 21 To R 24 They can be independently deuterium or C1-C 10 Alkyl groups (e.g., -CH3, -CH2CH3, etc.).

[0099] In one or more embodiments, L n1 It can be a ligand represented by Equation 1A-1:

[0100] Formula 1A-1

[0101] .

[0102] In Equation 1A-1,

[0103] X 11 It can be C(R) 11 ) or N, X 12 It can be C(R) 12 ) or N, X 13 It can be C(R) 13 ) or N, and X 14 It can be C(R) 14 ) or N,

[0104] X 21 It can be C(R) 21 ) or N, X 22 It can be C(R) 22 ) or N, X 23 It can be C(R)23 ) or N, and X 24 It can be C(R) 24 ) or N,

[0105] R 11 To R 14 Each independently, as described regarding R1,

[0106] R 21 To R 24 Each independently as described regarding R2, and

[0107] * and *' each represent the binding site with M1.

[0108] L in Formula 1 n2 For the ligand represented by Equation 1B:

[0109] Formula 1B

[0110] .

[0111] In Equation 1B, X3 is C or N, and X4 is C or N.

[0112] In one or more embodiments, X3 may be N, and X4 may be C.

[0113] In Formula 1B, the ring CY4 is a 6-membered carbon ring group or a 6-membered heterocyclic group.

[0114] In one or more embodiments, cycloCY4 may be a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0115] In Equation 1B, Y1 represents O, S, Se, and N(R). 51 ), or C(R) 52 (R) 53 ).

[0116] In Equation 1B, Ar1 and Ar2 are each independently substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0117] In one or more embodiments, Ar1 and Ar2 may each be independently substituted or unsubstituted C5-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C5-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60Hypoaryl, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, or substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0118] In Equation 1B, a1 and a2 are each an independent integer from 1 to 3.

[0119] In Equation 1B, when a1 is 2 or greater, Ar1 in quantity a1 can be the same or different from each other, and when a2 is 2 or greater, Ar2 in quantity a2 can be the same or different from each other.

[0120] In one or more embodiments, Ar1 and Ar2 may each be independently substituted or unsubstituted C5-C. 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, or substituted or unsubstituted C1-C 60 Hybrid aryl.

[0121] In some implementations, a1 and a2 can each be 1.

[0122] In Equation 1B, L1 represents O, S, Se, and N(R). 54 ), or C(R) 55 (R) 56 ).

[0123] In Equation 1B, m1 is an integer from 1 to 3.

[0124] When m1 in Equation 1B is 2 or greater, the number of L1s of m1 can be the same or different from each other.

[0125] In one or more embodiments, L1 may be O, S or Se, and m1 may be 1.

[0126] In one or more embodiments, the ring comprising Ar1, L1 and Ar2 in Formula 1B may be an octagonal ring.

[0127] In one or more embodiments, L n2 It can be a ligand represented by one of the formulas 1B(1)-1 to 1B(1)-3:

[0128] .

[0129] In equations 1B(1)-1 to 1B(1)-3,

[0130] X3, X4, ring CY4, Y1, Ar1, Ar2, a1, a2, L1, m1, R3, b3, R4, b4, R 40 b40 and b40 are as described in this article, and

[0131] R5 and R6 can each independently be deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;

[0132] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 combinations thereof;

[0133] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups;

[0134] Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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

[0135] -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 ),

[0136] Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 As described in this article,

[0137] b5 and b6 can each be an integer from 1 to 4 independently, and

[0138] * and *' each represent the binding site with M1.

[0139] In one or more embodiments, L n2 It can be a ligand represented by one of the formulas 1B(2)-1 to 1B(2)-6:

[0140]

[0141]

[0142] .

[0143] In equations 1B(1)-1 to 1B(2)-6,

[0144] X3, X4, Y1, Ar1, Ar2, a1, a2, L1, m1, R3, b3, R4, and b4 are each as described in this document.

[0145] X 41 It can be C(R) 41 ) or N, X 42 It can be C(R) 42 ) or N, X 43 It can be C(R) 43 ) or N, and X 44 It can be C(R) 44 ) or N,

[0146] R 41 To R 44 Each independently, such as regarding R 40 As described, and

[0147] * and *' each represent the binding site with M1.

[0148] In one or more embodiments, L n2 It can be a ligand represented by one of formulas 1B-1 to 1B-12:

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] .

[0155] In equations 1B-1 to 1B-12,

[0156] X3, X4, Y1, Ar1, Ar2, a1, a2, L1, R3, b3, R4, b4, and R 40 Each as described in this article,

[0157] R5 and R6 can each independently be deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;

[0158] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 combinations thereof;

[0159] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups;

[0160] Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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

[0161] -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

[0162] Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each as described in this article,

[0163] b5 and b6 can each be an integer from 1 to 4 independently.

[0164] b40 can be an integer from 1 to 4, and

[0165] * and *' each represent the binding site of M1.

[0166] R1 to R4 and R in equations 1A and 1B 40 and R 51 To R56 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, 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 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, 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 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=O)(Q8)(Q9).

[0167] In one or more embodiments, R1 to R4, R 40 and R 51 To R 56 Each can be independently:

[0168] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C20 alkoxy, or C1-C 20 Alkylthio;

[0169] Each of the following C1-C is replaced: 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof;

[0170] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl;

[0171] Each of the following substituted groups is replaced by: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, or combinations thereof; or

[0172] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=O)(Q8)(Q9), and

[0173] Q1 to Q9 can be independently defined as follows:

[0174] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0175] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0176] Each of the following is replaced by n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof.

[0177] In one or more embodiments, R1 to R4, R 40 and R 51 To R 56 Each can be independently:

[0178] Hydrogen, Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, Cl-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;

[0179] A group represented by one of formulas 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

[0180] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), or -N(Q4)(Q5).

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] In formulas 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, * indicates a binding site with an adjacent atom, "Ph" is phenyl, "TMS" is trimethylsilyl, and "TMG" is trimethylgermanyl.

[0202] In one or more embodiments, R1 and R2 can each be independently:

[0203] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, or C1-C 20 alkyl;

[0204] C1-C replaced as follows 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof;

[0205] Cyclopentyl, cyclohexyl, phenyl, naphthyl, fluorenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cenolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl or triazineyl;

[0206] Each of the following groups is substituted: cyclopentyl, cyclohexyl, phenyl, naphthyl, fluorenyl, pyrroleyl, thiopheneyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl. azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cenolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl or triazine: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof; or

[0207] -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3), and

[0208] Q1 to Q9 can be independently defined as follows:

[0209] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0210] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0211] Each of the following is replaced by n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof; and

[0212] R3, R4, R 40 and R 51 To R 56 Each can be independently:

[0213] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, or C1-C 20 alkyl;

[0214] C1-C replaced as follows 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof;

[0215] Cyclopentyl, cyclohexyl, phenyl, naphthyl, fluorenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cenolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, diazolyl or triazineyl; or

[0216] Each of the following groups is substituted: cyclopentyl, cyclohexyl, phenyl, naphthyl, fluorenyl, pyrroleyl, thiopheneyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl. azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cenolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl or triazine: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof.

[0217] Two or more adjacent R1s in Formula 1A are optionally bonded to each other to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0218] Two or more adjacent R2s in Formula 1A are optionally bonded to each other to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0219] Two or more adjacent R3s in Formula 1B are optionally bonded to each other to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0220] Multiple Rs in Equation 1B 40 Two or more adjacent C5-C molecules are optionally bonded to each other to form substituted or unsubstituted C5-C molecules. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0221] In Equation 1A, b1 and b2 are each an integer from 1 to 10, for example, an integer from 1 to 4.

[0222] In Equation 1B, b3 is an integer from 1 to 3.

[0223] In Equation 1B, b4 is either 1 or 2.

[0224] In Equation 1B, b40 is an integer from 1 to 4.

[0225] In Equations 1A and 1B, * and *' represent the binding sites with M1, respectively.

[0226] In one or more embodiments, the organometallic compound represented by Formula 1 may be one of compounds 1 to 77:

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239] .

[0240] In one or more embodiments, the organometallic compound represented by Formula 1 may be electrically neutral.

[0241] The organometallic compound represented by Formula 1 satisfies the structure of Formula 1 and includes a ligand having the structure represented by Formula 1B. Due to this structure, the organometallic compound represented by Formula 1 exhibits excellent luminescent properties and, by controlling the emission wavelength range, is suitable for use as a luminescent material with high color purity.

[0242] Furthermore, organometallic compounds represented by Formula 1 have excellent electromobility, and therefore electronic devices, such as organic light-emitting devices, that include at least one organometallic compound represented by Formula 1 can exhibit low driving voltage, high efficiency, low roll-off ratio, and / or long lifetime.

[0243] In one or more embodiments, the maximum emission wavelength (peak emission wavelength, λ) of the emission spectrum or electroluminescence spectrum of the organometallic compound represented by Formula 1. max The size can range from approximately 490 nanometers (nm) to approximately 550 nm.

[0244] The method for synthesizing the organometallic compounds represented by Formula 1 is as can be recognized by those skilled in the art by referring to the synthesis examples provided below.

[0245] Organometallic compounds represented by Formula 1 are suitable for use in the organic layer of an organic light-emitting device, for example, suitable as dopants in the emitting layer of the organic layer. Therefore, according to one or more embodiments, an organic light-emitting device includes: a first electrode; a second electrode; and an organic layer disposed or arranged between the first electrode and the second electrode, wherein the organic layer includes an emitting layer, and wherein the organic layer includes at least one organometallic compound represented by Formula 1.

[0246] By including an organic layer comprising at least one organometallic compound represented by Formula 1 as described herein, the organic light-emitting device may have excellent driving voltage, excellent maximum external quantum efficiency, and / or excellent lifetime characteristics.

[0247] Organometallic compounds represented by Formula 1 can be used between electrode pairs in organic light-emitting devices. For example, an organometallic compound represented by Formula 1 can be included in the emitter layer. In this respect, the organometallic compound can be used as a dopant, and the emitter layer can further include a host. When the emitter layer further includes a host, the amount of the host in the emitter layer can be greater than the amount of the at least one organometallic compound represented by Formula 1, based on weight.

[0248] 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.

[0249] The statements “(organic layer) comprises at least one organometallic compound represented by Formula 1” and “(organic layer) comprises at least one organometallic compound represented by Formula 1” are used interchangeably herein and can be interpreted as “(organic layer) may comprise one organometallic compound of Formula 1 or at least two different organometallic compounds of Formula 1”.

[0250] For example, the organic layer may include only compound 1 as one of the at least one organometallic compounds represented by formula 1. In this respect, compound 1 may be included in the emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may include both compound 1 and compound 2 as one of the at least one organometallic compounds represented by formula 1. In this respect, compound 1 and compound 2 may be present in the same layer (e.g., both compound 1 and compound 2 may be present in the emitting layer).

[0251] The first electrode can be the anode of the hole injection electrode and the second electrode can be the cathode of the electron injection electrode, or the first electrode can be the cathode of the electron injection electrode and the second electrode can be the anode of the hole injection electrode.

[0252] For example, in the organic light-emitting device, the first electrode may be an anode and the second electrode may be a cathode, and the organic layer may further include a hole transport region disposed between the first electrode and the emitting layer; and an electron transport region disposed between the emitting layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0253] As used herein, the term "organic layer" refers to one or more layers located between the first and second electrodes of an organic light-emitting device. In addition to organic compounds, "organic layer" may also include organometallic complexes containing metals.

[0254] Figure 1This is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Referring below, reference will be made to... Figure 1 The structure and manufacturing method of an organic light-emitting device 10 according to one or more embodiments are described, but the embodiments are not limited thereto. The organic light-emitting device 10 may have a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are stacked sequentially in the stated order.

[0255] A substrate may be further disposed below the first electrode 11 or on the second electrode 19. The substrate may be a substrate commonly used in organic light-emitting devices, such as a glass substrate or a transparent plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling (processing), and / or water resistance.

[0256] The first electrode 11 can be formed, for example, by depositing or sputtering a material for forming the first electrode 11 onto a substrate. The first electrode 11 can be an anode. The material used to form the first electrode 11 can be a material with a high work function to facilitate hole implantation. The first electrode 11 can be a reflective electrode, a semi-transparent semi-reflective electrode, or a transmissive electrode. The material used to form the first electrode 11 can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material used to form the first electrode 11 can 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).

[0257] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 11 is not limited to this.

[0258] The organic layer 15 can be disposed on the first electrode 11.

[0259] The organic layer 15 may include an emission layer and may further include a hole transport region and an electron transport region.

[0260] The hole transport region can be located between the first electrode 11 and the emitter layer.

[0261] 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.

[0262] The hole transport region may include a hole injection layer only 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 the corresponding layers of each structure are stacked sequentially from the first electrode 11 in the stated order.

[0263] When the hole transport region includes a hole injection layer, the hole injection layer can be formed on the first electrode 11 by using various methods such as vacuum deposition, spin coating, tape casting, and / or Langmuir-Broguet (LB) deposition, but the implementation is not limited to these methods.

[0264] When a hole injection layer is formed by vacuum deposition, the deposition conditions can vary depending on the compound used to form the hole injection layer, the desired structure of the hole injection layer, and its thermal properties. For example, the deposition temperature can be from about 100°C to about 500°C, and the vacuum level can be about 10. -8 To about 10 -3 The deposition rate can be from about 0.01 Å / s to about 100 Å / s, but the implementation is not limited thereto.

[0265] When a hole injection layer is formed by spin coating, the coating conditions can vary depending on the compound used to form the hole injection layer, the desired structure of the hole injection layer, and its thermal properties. For example, the coating rate can be from about 2,000 rpm to about 5,000 rpm, and the temperature at which the heat treatment is performed after coating to remove the solvent can be from about 80°C to about 200°C, but the implementation is not limited to these.

[0266] The conditions for forming the hole transport layer and the electron blocking layer can be found in the description provided for the conditions for forming the hole injection layer.

[0267] The hole transport region may include, for example, at least one of the following: 4,4',4''-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4''-tri{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'-cyclohexylidene bis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-sulfonylstyrene) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-sulfonylstyrene) (PANI / PSS), compounds represented by formula 201, or compounds represented by formula 202, but the embodiments are not limited thereto:

[0268]

[0269]

[0270] Formula 201

[0271]

[0272] Formula 202

[0273]

[0274] Ar in Equation 201 101 and Ar 102 Each can be independently:

[0275] Phenylidene, Pentaphenylene, Indene, Naphthylene, Phenylidene Alkyl, heptadeneyl, acenaphthene, fluoreneyl, phenentheneyl, anthraceneyl, fluoreneyl, benzo[9,10]phenentheneyl, pyreneyl, phenentheneyl alkyl, tetraphenyl, phenyl Base, Asia Benzyl, or pentanediphenyl; or

[0276] Each of the following substituted groups is phenylene, cyclopentadienylene, indenylene, naphthylene, and phenylene oxide. Alkyl, heptadeneyl, acenaphthene, fluoreneyl, phenentheneyl, anthraceneyl, fluoreneyl, benzo[9,10]phenentheneyl, pyreneyl, phenentheneyl alkyl, tetraphenyl, phenylene Base, Asia alkyl, or pentanephenyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thio groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, or combinations thereof.

[0277] In Equation 201, xa and xb can each be an integer from 0 to 5, or 0, 1, or 2. For example, xa can be 1 and xb can be 0, but xa and xb are not limited to these values.

[0278] R in equations 201 and 202 101 To R 108 R 111 To R 119 and R 121 To R 124 Each can be independently:

[0279] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), C1-C 10Alkyl groups (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.) or C1-C 10 Alkylthio;

[0280] Each of the following C1-C is replaced: 10 Alkyl, C1-C 10 alkoxy, or C1-C 10 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, or combinations thereof;

[0281] Phenyl, naphthyl, anthraceneyl, fluorenyl, or pyrene; or

[0282] Each of the following substituted groups is phenyl, naphthyl, anthraceneyl, fluorenyl, or pyrene: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio groups, or combinations thereof, but the implementation methods are not limited thereto.

[0283] R in Equation 201 109 Possible forms:

[0284] phenyl, naphthyl, anthraceneyl, or pyridyl; or

[0285] Each of the following substituted groups is phenyl, naphthyl, anthracene, or pyridyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, naphthyl, anthraceneyl, pyridyl, or combinations thereof.

[0286] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A, but the embodiments are not limited thereto:

[0287] Formula 201A

[0288]

[0289] In equation 201A, R 101 R 111 R 112 and R 109 Each can be as described in this article.

[0290] For example, compounds represented by formula 201 and compounds represented by formula 202 may include, but are not limited to, compounds HT1 to HT20:

[0291]

[0292]

[0293]

[0294] .

[0295] The thickness of the hole transport region can be from about 100 Å to about 10,000 Å, for example, from about 100 Å to about 1,000 Å. When the hole transport region includes at least one hole injection layer and a hole transport layer, the thickness of the hole injection layer can be from about 50 Å to about 10,000 Å, for example, from about 100 Å to about 1,000 Å, and the thickness of the hole transport layer can be from about 50 Å to about 2,000 Å, for example, from about 100 Å to about 1,500 Å. 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 can be obtained without a significant increase in driving voltage.

[0296] In addition to these materials, the hole transport region may further include charge-generating materials for improving conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed in the hole transport region.

[0297] The charge-generating material can be, for example, a p-doper. The p-doper can be, but is not limited to, a quinone derivative, a metal oxide, or a cyano-containing compound. For example, non-limiting examples of p-dopers include quinone derivatives such as tetracyanoquinone dimethyl ether (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl ether (F4-TCNQ), 1,3,4,5,7,8-hexafluorotetracyanonaphthoquinone dimethyl ether (F6-TCNNQ), etc.; metal oxides such as tungsten oxide, molybdenum oxide, etc.; or cyano-containing compounds such as compounds HT-D1 or F12, but the embodiments are not limited to these.

[0298]

[0299] .

[0300] Hole transport regions may include buffer layers.

[0301] The buffer layer can compensate for the optical resonant distance according to the wavelength of the light emitted from the emitting layer, thereby improving efficiency.

[0302] In some embodiments, when the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may be selected from, but is not limited to, the materials described above that can be used in the hole transport region and the body materials described below. For example, when the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may be mCP, which will be described below.

[0303] The emitter layer can be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emitter layer is formed by vacuum deposition or spin coating, the deposition or coating conditions can be generally similar to those used when forming the hole injection layer, although the deposition or coating conditions can vary depending on the material used to form the emitter layer.

[0304] The emitter layer may include a host and a dopant, and the dopant may include at least one organometallic compound represented by Formula 1.

[0305] The main body may include at least one of the following: 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TBADN), 9,10-bis(naphthyl-2-yl)anthracene (ADN) (also known as "DNA"), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP), 1,3-bis(N-carbazolyl)benzene (mCP), compound H50, compound H51, or compound GH3, but the embodiments are not limited thereto:

[0306]

[0307]

[0308] .

[0309] In one or more embodiments, the body may include a compound represented by the formula 301:

[0310] Formula 301

[0311]

[0312] Ar in Equation 301 111 and Ar 112 Each can be independently:

[0313] Phenylidene, naphthylene, phenanthrene, or pyrene; or

[0314] Phenylidene, naphthyl, phenanthrene, or pyrene, each substituted with phenyl, naphthyl, anthracene, or a combination thereof.

[0315] Ar in Formula 301 113 To Ar 116 Each can be independently:

[0316] C1-C substituted with phenyl, naphthyl, anthracene, or a combination thereof 10 alkyl;

[0317] Phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, or fluoreneyl;

[0318] Each of the following substituted groups is phenyl, naphthyl, anthraceneyl, pyrene, phenanthrene, or fluorenyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, fluorenyl, or combinations thereof; or

[0319] ,

[0320] However, the implementation methods are not limited to this.

[0321] Ar in Formula 301 113 To Ar 116 Each can be independently:

[0322] C1-C 10 Alkyl, phenyl, naphthyl, phenanthrene, or pyrene; or

[0323] Each of the following is replaced by phenyl, naphthyl, phenanthryl, or pyrene: phenyl, naphthyl, anthracene, or a combination thereof.

[0324] In Equation 301, g, h, i, and j can each be an integer from 0 to 4, and g, h, i, and j can each be, for example, 0, 1, or 2.

[0325] In one or more embodiments, the body may include a compound represented by formula 302:

[0326] Formula 302

[0327]

[0328] Ar in Equation 302 122 To Ar 125Ar in Equation 301 113 Defined in the same way.

[0329] Ar in Equation 302 126 and Ar 127 Each can be independently C1-C 10 Alkyl groups (e.g., methyl, ethyl, propyl, etc.).

[0330] In Equation 302, k and l can each be an integer from 0 to 4 independently. For example, k and l can each be 0, 1, or 2 independently.

[0331] When the organic light-emitting device is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, and / or a blue emitting layer. In one or more embodiments, the emitting layer may have a structure in which red emitting layers, green emitting layers, and / or blue emitting layers are stacked, but the embodiments are not limited thereto, and therefore, various variations such as the emission of white light are possible.

[0332] When the emitter layer comprises a host and a dopant, the amount of dopant is typically from about 0.01 parts by weight to about 15 parts by weight relative to 100 parts by weight of the host, but the implementation is not limited thereto.

[0333] The thickness of the emitting layer can be from about 100 Å to about 1,000 Å, for example from about 200 Å to about 600 Å. When the thickness of the emitting layer is within the range described above, excellent light emission characteristics can be obtained without a significant increase in driving voltage.

[0334] Next, the electron transmission region can be located or set on the emission layer.

[0335] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0336] 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 to these. The electron transport layer may have a multilayer structure or a single-layer structure comprising two or more different materials.

[0337] The conditions for forming the hole blocking layer, electron transport layer, and electron injection layer that constitute the electron transport region can be found in the description provided for the conditions for forming the hole injection layer.

[0338] 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,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), but the embodiments are not limited thereto:

[0339] .

[0340] The thickness of the hole blocking layer can be from about 20 Å to about 1,000 Å, for example from about 30 Å to about 300 Å. When the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics can be obtained without a significant increase in driving voltage.

[0341] The electron transport layer may include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinoline)aluminum (Alq3), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), or 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), but the embodiments are not limited thereto.

[0342] .

[0343] In one or more embodiments, the electronic transport layer may include at least one of ET1 to ET25, but the embodiments are not limited thereto:

[0344]

[0345]

[0346] .

[0347] The thickness of the electron transport layer can be from about 100 Å to about 1,000 Å, for example from about 150 Å to about 500 Å. When the thickness of the electron transport layer is within these ranges, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage.

[0348] In addition to the materials described above, the electron transport layer may further include a metallic material.

[0349] Metal-containing materials may include Li complexes. Li complexes may include, for example, compounds ET-D1 (lithium 8-hydroxyquinoline, Liq) or ET-D2, but the embodiments are not limited thereto:

[0350] .

[0351] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 19.

[0352] The electron-injected layer may include Liq, LiF, NaCl, CsF, Li2O, BaO, or combinations thereof.

[0353] The thickness of the electron injection layer can be from about 1 Å to about 100 Å, for example from about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.

[0354] The second electrode 19 may be disposed 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, alloy, conductive compound, or 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 materials for forming the second electrode 19. In one or more embodiments, various modifications, such as using ITO or IZO to form a transmissive second electrode, are possible for fabricating a top-emitting light-emitting device.

[0355] Already referenced Figure 1 Organic light-emitting devices have been described, but implementation methods are not limited thereto.

[0356] According to one or more embodiments, the diagnostic composition includes at least one organometallic compound represented by Formula 1.

[0357] Organometallic compounds represented by Formula 1 can provide high luminescence efficiency, and therefore, diagnostic compositions comprising at least one organometallic compound represented by Formula 1 can have high diagnostic efficiency.

[0358] Diagnostic compositions can be used in a variety of applications, including diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc., but implementation methods are not limited thereto.

[0359] As used in this article, the term "C1-C" 60 "Alkyl" refers to a monovalent group of a straight-chain or branched saturated aliphatic hydrocarbon having 1 to 60 carbon atoms. In this article, C1-C 60 Alkyl groups can be C1-C 20 Alkyl groups, such as C1-C10 Alkyl, C1-C6 alkyl, or C1-C3 alkyl. Each alkyl group may be straight-chain or branched. In the case of branched alkyl groups, the lower limit of the carbon number range for each of the above alkyl groups becomes 3. C1-C 60 Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, etc., as used herein. 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Divalent groups with the same structure as alkyl groups.

[0360] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and non-limiting examples include methoxy, ethoxy, isopropoxy, etc.

[0361] As used in this article, the term "C1-C" 60 "Alkylthio" refers to the group consisting of -SA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups.

[0362] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C... 60 The alkyl group contains at least one carbon-carbon double bond at its middle or end, and non-limiting examples include vinyl, propenyl, butenyl, etc. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to a group that has a C2-C bond structure. 60 Divalent groups with the same structure as alkenyl groups.

[0363] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60 The alkyl group contains at least one carbon-carbon triple bond at its middle or end, and non-limiting examples include ethynyl, propynyl, etc. As used herein, the term "C2-C" is used... 60 "Immyneyl" refers to a group that has a similar structure to C2-C2. 60 Divalent groups with the same structure as alkynyl groups.

[0364] As used in this article, the term "C3-C" 10"Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms as cyclic atoms, and non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, etc. The term "C3-C" is used herein. 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Divalent groups with the same structure as cycloalkyl groups.

[0365] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated cyclic group having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a cyclic atom and 1 to 10 carbon atoms as cyclic atoms, and non-limiting examples include tetrahydrofuranyl, tetrahydrothiophenyl, etc. The term "C1-C" as used herein is also relevant. 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with the same structure as heterocyclic alkyl groups.

[0366] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent hydrocarbon cyclic group having 3 to 10 carbon atoms as cyclic atoms and at least one carbon-carbon double bond in its ring and not being aromatic, and examples include cyclopentenyl, cyclohexenyl, cycloheptenyl, or norbornenyl. As used herein, the term "C3-C" is also used. 10 "Cycloalkylene" refers to a group that has a C3-C6 bond structure. 10 A divalent group with the same structure as a cycloalkenyl group.

[0367] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent cyclic group that has at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a cyclic atom, 1 to 10 carbon atoms as cyclic atoms, and at least one double bond, and is not aromatic. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 2,3-dihydrofuranyl, 2,3-dihydrothiophenyl, etc., as used herein with the term "C1-C". 10 "Heterocyclic alkenyl" refers to a group that has a similar structure to C1-C1. 10 Divalent groups with the same structure as heterocyclic alkenyl groups.

[0368] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic ring system with 6 to 60 carbon atoms as cyclic atoms, and as used herein in the term "C6-C". 60 "Arylene" refers to a divalent group in a carbocyclic aromatic ring system with 6 to 60 carbon atoms as cyclic atoms. (C6-C) 60Non-limiting examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, Base, etc. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the rings may be fused together.

[0369] As used in this article, the term "C7-C" 60 "alkylaryl" refers to an alkyl group formed by at least one C1-C2 group. 54 Alkyl-substituted C6-C 59 Aryl. As used in this text, the term "C7-C" 60 "Arylalkyl" refers to an alkyl group consisting of at least one C6-C bond. 59 aryl-substituted C1-C 54 alkyl.

[0370] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having the following heterocyclic aromatic ring system: it has at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a cyclic atom and 1 to 60 carbon atoms as cyclic atoms. As used herein, the term "C1-C" is also relevant. 60 "Hypo-heteroaryl" refers to a divalent group having the following heterocyclic aromatic ring system: it contains at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a cyclic atom, and has 1 to 60 carbon atoms as cyclic atoms. C1-C 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, etc. When C1-C... 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the rings can fused together.

[0371] As used in this article, the term "C2-C" 60 "alkyl heteroaryl" refers to an alkyl group formed by at least one C1-C2 group. 59 Alkyl-substituted C1-C 59 heteroaryl. As used in this text, the term "C2-C" is used in conjunction with... 60 "Heteroarylalkyl" refers to an alkyl group consisting of at least one C1-C2 group. 59 heteroaryl-substituted C1-C 59 alkyl.

[0372] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60 Aryl), and as used herein, the term "C6-C" 60 "Arylthio" refers to -SA103 (where A) 103 For C6-C 60 Aryl).

[0373] As used in this article, the term "C1-C" 60 "Heteroaryloxy" indicates -OA 104 (where A) 104 For C1-C 60 (Heteroaryl), and as used herein, the term "C1-C 60 "Heteroarylsulfonyl" indicates -SA 105 (where A) 105 For C1-C 60 (Miscellaneous aromatic compounds).

[0374] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) that has two or more rings fused together, has only carbon atoms as cyclic atoms, and is not aromatic in its entirety. Non-limiting examples of monovalent nonaromatic fused polycyclic groups include fluorene groups, etc. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.

[0375] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms) that has two or more fused rings, has heteroatoms selected from B, N, O, P, Si, S, Se, and Ge as cyclic atoms in addition to carbon atoms, and is not aromatic in its overall structure. Non-limiting examples of monovalent nonaromatic fused heterocyclic groups include carbazole groups, etc. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused heterocyclic group.

[0376] As used in this article, the term "C5-C" 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as cyclic atoms. (C5-C) 30 The carbon ring group can be a monocyclic group or a polycyclic group.

[0377] As used in this article, the term "C1-C" 30 A "heterocyclic group" refers to a saturated or unsaturated cyclic group that, in addition to 1 to 30 carbon atoms as cyclic atoms, has at least one heteroatom selected from B, N, O, Si, P, S, Se, and Ge as a cyclic atom. C1-C 30 Heterocyclic groups can be monocyclic or polycyclic.

[0378] Replacement C5-C 30Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, 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 Heteroaryl groups, substituted C1-C 60 At least one substituent of the heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group may be:

[0379] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;

[0380] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 combinations thereof;

[0381] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups;

[0382] Each of the following C3-C is replaced: 10cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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

[0383] -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

[0384] Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, 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 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, 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 C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C60 heteroaryl thiols, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

[0385] For example, Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each of these groups can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, or each can be unsubstituted or substituted with deuterium, C1-C 60 Alkyl, C3-C 10 cycloalkyl, C6-C 60 aryl, or combined substituted C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups.

[0386] Hereinafter, organometallic compounds represented by Formula 1 and organic light-emitting devices comprising them, according to one or more embodiments, will be described in further detail with reference to synthetic examples and embodiments. However, the following examples are not intended to limit the scope of this disclosure. The phrase "using B instead of A" used in describing synthetic examples means that, in molar equivalents, the amount of A used is the same as the amount of B used.

[0387] Example

[0388] Synthesis Example 1: Synthesis of Compound 1

[0389]

[0390] Synthesis of compound 1A(1)

[0391] 2-Phenyridine (1.75 g, 11.28 mmol) and iridium chloride trihydrate (IrCl3(H2O)) were prepared. n (n=3) (1.89 g, 5.37 mmol) was mixed with 60 mL of 2-ethoxyethanol and 20 mL of deionized (DI) water and heated under reflux for 24 hours with stirring, then cooled to room temperature. The resulting solid was filtered and separated, thoroughly washed with water, methanol and n-hexane in the order stated, and the obtained solid was dried in a vacuum oven to obtain 2.33 g of compound 1A(1) (yield: 81%).

[0392] Synthesis of Compound 1A

[0393] Compound 1A(1) (2.33 g, 2.17 mmol) was mixed with 75 mL of dichloromethane (DCM), and then silver trifluoromethanesulfonate (AgOTf) (1.17 g, 4.56 mmol) mixed with 25 mL of methanol (MeOH) was added. The resulting reaction solution was then stirred at room temperature for 18 hours while blocking light with aluminum foil, and then filtered through diatomaceous earth to remove the solids produced. The solvent was removed from the filtrate under reduced pressure to obtain the solid (compound 1A), which was used in the next reaction without further purification.

[0394] Synthesis of Compound 1B

[0395] Under a nitrogen atmosphere, 2-bromo-7-oxa-1,2a-diazadibenzo[4,5:7,8]cyclooctano[1,2,3-cd]indene (2.5 g, 6.88 mmol) and dibenzo[b,d]furan-4-ylboronic acid (1.75 g, 8.26 mmol) were dissolved in 120 mL of 1,4-dioxane. Potassium carbonate (K₂CO₃) (2.85 g, 20.65 mmol) dissolved in 40 mL of DI water was added to the reaction mixture, along with a palladium catalyst (tetra(triphenylphosphine)palladium(0), Pd(PPh₃)₄) (0.56 g, 0.48 mmol). The reaction mixture was then stirred and heated at 100°C under reflux. The reaction mixture was then allowed to cool to room temperature. Following extraction, the obtained solid was purified by column chromatography (eluent: n-hexane and ethyl acetate) to obtain 1.92 g of compound 1B (yield: 62%). The obtained compound was confirmed by high-resolution mass spectrometry (HRMS) using matrix-assisted laser desorption / ionization (MALDI) and HPLC.

[0396] HRMS (MALDI): For C 31 H 18 Calculated value of N2O2: m / z 450.1368; measured value: 450.1361.

[0397] Synthesis of Compound 1

[0398] Compound 1A (2.29 g, 3.21 mmol) and compound 1B (1.45 g, 3.21 mmol) were mixed with 32 mL of 2-ethoxyethanol and 32 mL of N,N-dimethylformamide, and heated under reflux at 120°C for 24 hours with stirring, followed by cooling. The solid obtained by concentrating the resulting mixture under reduced pressure was purified by column chromatography (eluent: n-hexane and dichloromethane) to obtain 0.98 g of compound 1 (yield: 32%). The obtained compounds were confirmed by HRMS (MALDI) and HPLC analysis.

[0399] HRMS (MALDI): For C 53 H 33 Calculated value of IrN4O2: m / z 950.2233; measured value: 950.2239.

[0400] Synthesis Example 2: Synthesis of Compound 18

[0401]

[0402] Synthesis of compound 18A(1)

[0403] 5-(methyl-d3)-2-phenylpyridine (2.1 g, 12.19 mmol) and iridium chloride trihydrate (2.04 g, 5.81 mmol) were mixed with 60 mL of 2-ethoxyethanol and 20 mL of DI water and heated under reflux for 24 hours with stirring, then cooled to room temperature. The resulting solid was filtered and separated, washed thoroughly with water, methanol and n-hexane in sequence, and dried in a vacuum oven to obtain 2.58 g of compound 18A(1) (yield: 78%).

[0404] Synthesis of Compound 18A

[0405] Compound 18A(1) (2.58 g, 2.26 mmol) was mixed with 75 mL of dichloromethane, and then AgOTf (1.22 g, 4.75 mmol) mixed with 25 mL of methanol was added. The resulting reaction solution was then stirred at room temperature for 18 hours while blocking light with aluminum foil, and then filtered through diatomaceous earth to remove the solids produced. The solvent was removed from the filtrate under reduced pressure to obtain the solid (compound 18A), which was used in the next reaction without additional purification.

[0406] Synthesis of Compound 18B

[0407] Under a nitrogen atmosphere, 2-bromo-7-oxa-1,2a-diazadibenzo[4,5:7,8]cyclooctano[1,2,3-cd]indene (2.49 g, 6.86 mmol) and (7-(methyl-d3)dibenzo[b,d]furan-4-yl)boronic acid (1.88 g, 8.23 ​​mmol) were dissolved in 120 mL of 1,4-dioxane. Potassium carbonate (K₂CO₃) (2.84 g, 20.57 mmol) dissolved in 40 mL of DI water was added to the reaction mixture, along with a palladium catalyst (Pd(PPh₃)₄) (0.56 g, 0.48 mmol). The reaction mixture was then heated and stirred at 100°C under reflux. The reaction mixture was then allowed to cool to room temperature. Following extraction, the obtained solid was purified by column chromatography (eluent: n-hexane and ethyl acetate) to obtain 1.96 g of compound 18B (yield: 61%). The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0408] HRMS (MALDI): For C 32 H 17 Calculated value of D3N2O2: m / z 467.1713; measured value: 467.1719.

[0409] Synthesis of Compound 18

[0410] 1.03 g of compound 18 (yield: 31%) was synthesized using a method similar to that used for compound 1 in Synthetic Example 1, except that compound 18A (2.5 g, 3.34 mmol) was used instead of compound 1A, and compound 18B (1.56 g, 3.34 mmol) was used instead of compound 1B. The obtained compounds were confirmed by HRMS (MALDI) and HPLC analysis.

[0411] HRMS (MALDI): For C 56 H 30 Calculated value of D9IrN4O2: m / z 1001.3267; Measured value: 1001.3261.

[0412] Synthesis Example 3: Synthesis of Compound 40

[0413]

[0414] Synthesis of compound 40A(1)

[0415] 2-Phenyl-5-(trimethylsilyl)pyridine (2.1 g, 9.24 mmol) and iridium chloride trihydrate (1.55 g, 4.40 mmol) were mixed with 60 mL of 2-ethoxyethanol and 20 mL of deionized water. The mixture was heated under reflux with stirring for 24 hours, and then cooled to room temperature. The resulting solid was filtered and separated, thoroughly washed with water, methanol, and n-hexane in the order stated, and dried in a vacuum oven to obtain 2.18 g of compound 40A(1) (yield: 73%).

[0416] Synthesis of Compound 40A

[0417] Compound 40A(1) (2.18 g, 1.60 mmol) was mixed with 75 mL of dichloromethane, and then AgOTf (0.86 g, 3.36 mmol) mixed with 25 mL of methanol was added. The resulting reaction solution was then stirred at room temperature for 18 hours while blocking light with aluminum foil, and filtered through diatomaceous earth to remove the solids produced. The solvent was removed from the filtrate under reduced pressure to obtain the solid (compound 40A), which was used in the next reaction without further purification.

[0418] Synthesis of Compound 40B

[0419] Under a nitrogen atmosphere, 2-bromo-7-oxa-1,2a-diazadibenzo[4,5:7,8]cyclooctano[1,2,3-cd]indene (2.49 g, 6.86 mmol) and 4,4,5,5-tetramethyl-2-(7-phenyldibenzo[b,d]furan-4-yl)-1,3,2-dioxacyclopentaborane (3.05 g, 8.23 ​​mmol) were dissolved in 120 mL of 1,4-dioxane. Potassium carbonate (K₂CO₃) (2.84 g, 20.57 mmol) dissolved in 40 mL of DI water was added to the reaction mixture, along with a palladium catalyst (Pd(PPh₃)₄) (0.56 g, 0.48 mmol). The reaction mixture was then stirred and heated at 100°C under reflux. Following extraction, the obtained solid was purified by column chromatography (eluent: n-hexane and ethyl acetate) to obtain 2.31 g of compound 40B (yield: 64%). The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0420] HRMS (MALDI): For C 37 H 22 Calculated value of N2O2: m / z 526.1681; measured value: 526.1688.

[0421] Synthesis of Compound 40

[0422] Compound 40 (yield: 35%) was synthesized using a method similar to that used in the synthesis of compound 1 in Synthetic Example 1, except that compound 1A was replaced with compound 40A (1.87 g, 2.18 mmol) and compound 1B was replaced with compound 40B (1.15 g, 2.18 mmol). The obtained compounds were confirmed by HRMS (MALDI) and HPLC analysis.

[0423] HRMS (MALDI): For C 65 H 53 Calculated value of IrN4O2Si2: m / z 1170.3336; measured value: 1170.3331.

[0424] Synthesis Example 4: Synthesis of Compound 63

[0425]

[0426] Synthesis of compound 63A(1)

[0427] 2-Phenyl-5-(trimethylgermanyl)pyridine (2.1 g, 7.72 mmol) and iridium chloride trihydrate (1.30 g, 3.68 mmol) were mixed with 60 mL of 2-ethoxyethanol and 20 mL of DI water and heated under reflux for 24 hours with stirring, then cooled to room temperature. The resulting solid was filtered and separated, thoroughly washed with water, methanol, and n-hexane in the order stated, and dried in a vacuum oven to obtain 2.18 g of compound 63A(1) (yield: 77%).

[0428] Synthesis of Compound 63A

[0429] Compound 63A(1) (2.18 g, 1.42 mmol) was mixed with 75 mL of dichloromethane, and then AgOTf (0.76 g, 2.97 mmol) mixed with 25 mL of methanol was added. The resulting reaction solution was then stirred at room temperature for 18 hours while blocking light with aluminum foil, and filtered through diatomaceous earth to remove the solids produced. The solvent was removed from the filtrate under reduced pressure to obtain the solid (compound 63A), which was used in the next reaction without further purification.

[0430] Synthesis of Compound 63B

[0431] Under a nitrogen atmosphere, 2-bromo-5-phenyl-7-oxa-1,2a-diazadibenzo[4,5:7,8]cyclooctano[1,2,3-cd]indene (2.53 g, 5.76 mmol) and 4,4,5,5-tetramethyl-2-(7-phenyldibenzo[b,d]furan-4-yl)-1,3,2-dioxacyclopentaborane (2.56 g, 6.91 mmol) were dissolved in 120 mL of 1,4-dioxane. Potassium carbonate (K₂CO₃) (2.39 g, 17.28 mmol) dissolved in 40 mL of DI water was added to the reaction mixture, along with a palladium catalyst (Pd(PPh₃)₄) (0.47 g, 0.40 mmol). The reaction mixture was then stirred and heated at 100°C under reflux. Following extraction, the obtained solid was purified by column chromatography (eluent: n-hexane and ethyl acetate) to obtain 2.11 g of compound 63B (yield: 61%). The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0432] HRMS (MALDI): For C 43 H 26 Calculated value of N2O2: m / z 602.1994; measured value: 602.1999.

[0433] Synthesis of Compound 63

[0434] Compound 63 (yield: 32%) was synthesized using a method similar to that used for compound 1 in Synthetic Example 1, except that compound 1A was replaced with compound 63A (1.82 g, 1.92 mmol) and compound 1B was replaced with compound 63B (1.16 g, 1.92 mmol). The obtained compounds were confirmed by HRMS (MALDI) and HPLC analysis.

[0435] HRMS (MALDI): For C 71 H 57 Calculated value of Ge2IrN4O2: m / z 1338.2534; measured value: 1338.2539.

[0436] Example 1

[0437] The patterned indium tin oxide (ITO) glass substrate, which serves as the anode, is cut to a size of 50 mm x 50 mm x 0.5 mm, ultrasonically cleaned with isopropanol and DI water for 5 minutes each, cleaned by ultraviolet (UV) irradiation and ozone exposure for 30 minutes, and then loaded onto a vacuum deposition apparatus.

[0438] On the anode, compound HT3 and F12-P-dopant are vacuum co-deposited in a weight ratio of 98:2 to form a hole injection layer with a thickness of 100 Å, and on the hole injection layer, compound HT3 is vacuum deposited to form a hole transport layer with a thickness of 1650 Å.

[0439] On the hole transport layer, compound GH3 (host) and compound 1 (dopant) were vacuum co-deposited in a weight ratio of 92:8 to form an emitter layer with a thickness of 400 Å.

[0440] On the emitter layer, compound ET3 and Liq-N-dopant are vacuum co-deposited in a 50:50 volume ratio to form an electron transport layer with a thickness of 350 Å. On the electron transport layer, Liq-N-dopant is vacuum deposited to form an electron injection layer with a thickness of 10 Å. On the electron injection layer, Al is vacuum deposited to form a cathode with a thickness of 1000 Å, thereby completing the fabrication of the organic light-emitting device.

[0441]

[0442] Examples 2 to 4 and Comparative Examples 1 to 3

[0443] The organic light-emitting device was fabricated using a method similar to that of Example 1, except that, during the formation of the emitting layer, the compounds shown in Table 1 below were used instead of compound 1.

[0444] Evaluation Example 1: Characterization of Organic Light-Emitting Devices

[0445] For the organic light-emitting devices of Examples 1 to 4 and Comparative Examples 1 to 3, the driving voltage (V), maximum external quantum efficiency (Max EQE, %), maximum emission wavelength (nm), roll-off ratio (%), and lifetime (LT) were evaluated. 97 The relative percentages are shown in Table 1 below. As evaluation equipment, a current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used. The roll-off ratio was calculated according to Equation 1 below and is the lifetime (LT) measured at 6000 nits as the time required for the luminance to reach 97% of the initial luminance of 100%. 97 (As shown in Comparative Example 1)

[0446] Equation 1

[0447] Roll-off ratio = {1 - (emission efficiency (at 6000 nits) / maximum emission efficiency)} x 100%

[0448] Table 1

[0449]

[0450]

[0451]

[0452] As confirmed by Table 1, the organic light-emitting devices of Examples 1 to 4 have the following characteristics: low driving voltage, high maximum external quantum efficiency, low roll-off ratio, and long lifetime.

[0453] Furthermore, it was confirmed that compared with the organic light-emitting devices of Comparative Examples 1 to 3, the organic light-emitting devices of Examples 1 to 4 exhibited lower driving voltage, higher maximum external quantum efficiency, smaller roll-off ratio, and longer lifetime.

[0454] Because organometallic compounds represented by Formula 1 possess excellent electrical properties, electronic devices using at least one of these compounds, such as organic light-emitting devices using at least one of these compounds, can exhibit characteristics such as low driving voltage, high maximum external quantum efficiency, low roll-off ratio, and long lifetime. Therefore, high-quality organic light-emitting devices can be realized using at least one of these organometallic compounds.

[0455] It should be understood that the exemplary embodiments described herein are to be considered in a descriptive sense only and are not intended for limiting purposes. The descriptions of features or aspects in the various embodiments should be typically considered applicable to other similar features or aspects in other embodiments. While one or more exemplary embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims.

Claims

1. An organometallic compound represented by Formula 1: Formula 1 In Formula 1, M1(L n1 ) n1 (L n2 ) n2 wherein, M1 is a transition metal, n1 and n2 are each independently 1 or 2, L n1 is a ligand represented by Formula 1A, L n2 is a ligand represented by Formula 1B, and Formula 1A Formula 1B wherein, in Formulas 1A and 1B, X1 is C or N, X2 is C or N, X3 is C or N, and X4 is C or N, ring CY4 is a 6-membered carbocyclic group or a 6-membered heterocyclic group, each of ring CY1and ring CY2is independently C5-C 30 carbocyclic group or C1-C 30 heterocyclic group, a1 and a2 are each independently an integer of 1 to 3, Y1is O, S, Se, N(R 51 ), or C(R 52 )(R 53 ), Ar1and Ar2are each independently a substituted or unsubstituted C5-C 30 a carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group, m1 is an integer of 1 to 3, L1is O, S, Se, N(R 54 ), or C(R 55 )(R 56 ), b1 and b2 are each independently an integer of 1 to 10, R1to R4, R 40 , and R 51 to R 56 are each independently hydrogen, deuterium, -F, -CI, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylate group or a salt thereof, sulfonate group or a salt thereof, phosphate group or a salt thereof, 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 C6-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 alkylaryl, 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 alkylheteroaryl, substituted or unsubstituted C2-C 60 heteroarylalkyl, substituted or unsubstituted C1-C 60 heteroaryloxy, substituted or unsubstituted C1-C 60 heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused 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 R1groups optionally are bonded to each other to form a substituted or unsubstituted C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group, two or more adjacent R2groups together form a substituted or unsubstituted C5-C10 30 carbocyclic group or a substituted or unsubstituted C1-C6 30 heterocyclic group, two or more adjacent R3groups optionally are bonded to each other to form a substituted or unsubstituted C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group, R 40 two or more of which adjacent R 30 carbon ring group or a substituted or unsubstituted C1-C 30 heterocyclic group, b3 is an integer of 1 to 3, b4 is 1 or 2, b40 is an integer of 1 to 4, * and *' each represent a binding site to M1, 2. The organometallic compound according to claim 1, wherein substituted C5-C 30 carbocyclic group, substituted C1-C 30 heterocyclic group, 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 alkylaryl, substituted C7-C 60 arylalkyl, substituted C6-C 60 aryloxy, substituted C6-C 60 arylthio, substituted C1-C 60 heteroaryl, substituted C2-C 60 alkylheteroaryl, substituted C2-C 60 heteroarylalkyl, substituted C1-C 60 heteroaryloxy, substituted C1-C 60 heteroarylthio, each of the at least one substituents of the substituted monovalent non-aromatic fused polycyclic group and the substituted monovalent non-aromatic fused heteropolycyclic group is independently: deuterium, -F, -CI, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, or C1-C 60 alkylthio; Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 combinations thereof; C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group; Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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(=O)(Q 28 ), -P(=O)(Q 29 ), -P(=O)(Q 28 ), -P(=O)(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 Q1to Q9, Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 are each independently hydrogen, deuterium, -F, -CI, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylate group or salt thereof, sulfonate group or salt thereof, phosphate group or salt thereof, 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 alkylaryl, 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 alkylheteroaryl, substituted or unsubstituted C2-C 60 heteroarylalkyl, substituted or unsubstituted C1-C 60 heteroaryloxy, substituted or unsubstituted C1-C 60 heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group. M1 is Ir, and n1 and n2 are each independently 1 or 2.

3. The organometallic compound according to claim 1, wherein ring CY1 and ring CY2 are each independently a phenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalyl group, a quinazolyl group, a phenanthrolinyl group, a benzofuranyl group, a benzothiophenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, an azaf luorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or an azadibenzosilolyl group. In Formulas CY(1)-1 to CY(1)-16, 4. The organometallic compound according to claim 1, wherein the compound in formula 1A is composed of... The part represented is a group represented by one of the formulas CY(1)-1 to CY(1)-16: wherein, * represents a binding site to M1, and R 11 to R 14 each independently as described in claim 1 for R1, with the proviso that R 11 to R 14 is not hydrogen, *" represents a binding site to an adjacent atom. In Formulas CY(2)-1 to CY(2)-16, 5. The organometallic compound according to claim 1, wherein the compound in formula 1A is composed of... The part represented is a group represented by one of the formulas CY(2)-1 to CY(2)-16: wherein, *' represents a binding site to M1, and R 21 to R 24 each independently as described in claim 1 for R2, with the proviso that R 21 to R 24 is not hydrogen, *" represents a binding site to an adjacent atom. Formula 1A-1 6. The organometallic compound of claim 1, wherein L n1 is a ligand represented by formula 1A-1: In Formula 1A-1, wherein * and *' each represent a binding site to M1. X 11 is C(R 11 ) or N, X 12 is C(R 12 ) or N, X 13 is C(R 13 ) or N, and X 14 is C(R 14 ) or N, X 21 is C(R 21 ) or N, X 22 is C(R 22 ) or N, X 23 is C(R 23 ) or N, and X 24 is C(R 24 ) or N, R 11 to R 14 each independently as described in claim 1 for R1, R 21 to R 24 each independently are as described in Claim 1 for R2, and 8. The organometallic compound according to claim 1, wherein 7. The organometallic compound of claim 1, wherein Ar1and Ar2are each independently a substituted or unsubstituted C5-C 10 substituted or unsubstituted C1-C 10 substituted or unsubstituted C1-C 10 substituted or unsubstituted C1-C 10 substituted or unsubstituted C1-C 60 substituted or unsubstituted C1-C 60 substituted or unsubstituted C1-C a1 and a2 are each 1. Ar1and Ar2are each independently substituted or unsubstituted C5-C 10 cycloalkenylene, substituted or unsubstituted C1-C 10 heterocycloalkenylene, substituted or unsubstituted C6-C 60 aryl, or substituted or unsubstituted C1-C 60 heteroaryl, and 9. The organometallic compound according to claim 1, wherein L1 is O, S, or Se, and m1 is 1.

10. The organometallic compound according to claim 1, wherein the ring including Ar1, L1, and Ar2 in Formula 1B is an octagonal ring. In Formulas 1B(1)-1 to 1B(1)-3, 11. The organometallic compound of claim 1, wherein L n2 is a ligand represented by one of Formulae 1B(1)-1 to 1B(1)-3: wherein R5 and R6 are each independently: X3, X4, ring CY4, Y1, Ar1, Ar2, a1, a2, L1, m1, R3, b3, R4, b4, R 40 and b40 are each as described in claim 1, or deuterium, -F, -CI, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, or C1-C 60 alkylthio; Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 combinations thereof; C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group; Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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(=O)(Q 28 )(Q 29 ), -P(=O)(Q 28 )(Q 29 ), or a combination thereof; b5 and b6 are each independently an integer of 1 to 4, and -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 ), Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 As described in claim 1, * and *' each represent a binding site to M1. In Formulas 1B(1)-1 to 1B(2)-6, 12. The organometallic compound of claim 1, wherein L n2 is a ligand represented by one of Formulae IB(2)-1 to IB(2)-6: wherein X3, X4, Y1, Ar1, Ar2, a1, a2, L1, m1, R3, b3, R4, and b4 are each as described in claim 1, * and *' each represent a binding site to M1. X 41 is C(R 41 ) or N, X 42 is C(R 42 ) or N, X 43 is C(R 43 ) or N, and X 44 is C(R 44 ) or N, R 41 to R 44 each independently are as described in claim 1 for R 40 and In Formulas 1B-1 to 1B-12, 13. The organometallic compound of claim 1, wherein L n2 is a ligand represented by one of Formulae 1B-1 to 1B-12: wherein, R5 and R6 are each independently: X3, X4, Y1, Ar1, Ar2, a1, a2, L1, R3, b3, R4, b4, and R 40 each as described in claim 1, or deuterium, -F, -CI, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, or C1-C 60 alkylthio; Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 combinations thereof; C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group; Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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(=O)(Q 28 )(Q 29 ), -P(=O)(Q 28 )(Q 29 ), or a combination thereof; b5 and b6 are each independently an integer of 1 to 4, -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 ), Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 as described in claim 1, b40 is an integer of 1 to 4, and * and *' each represent a binding site to M1. ​ 14. The organometallic compound of claim 1, wherein R1through R4, R 40 , and R 51 through R 56 are each independently: hydrogen, deuterium, -F, -CI, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C1-C 20 alkyl, C1-C 20 alkoxy, or C1-C 20 alkylthio; Each of the following C1-C is replaced: 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof; cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzoisothiazolyl, benzoxazolyl, benzothiazolyl, benzothiadiazolyl, benzodioxolyl, benzodioxanyl, benzodioxinyl, benzotriazolyl, benzotetrazolyl, benzodiazinyl, benzotriazinyl, dibenzofuranyl, dibenzothiophenyl, benzcabazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl;​​​​​ Each of the following substituted groups is replaced by: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, or combinations thereof; or -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=0)(Q8)(Q9), and each of Q1to Q9is independently: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, i-pentyl, s-pentyl, t-pentyl, phenyl, or naphthyl; or n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, t-butyl, n-pentyl, iso-pentyl, sec-pentyl, t-pentyl, phenyl, or naphthyl, each substituted with deuterium, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, halogen, C3-C6cycloalkyl, phenyl, or a combination thereof; 10 alkyl, phenyl, or a combination thereof.

15. An organic light-emitting device, comprising: a first electrode; a second electrode; and an organic layer arranged between the first electrode and the second electrode, wherein the organic layer comprises an emissive layer, and wherein the organic layer comprises at least one organometallic compound according to any one of claims 1 to 14.

16. The organic light-emitting device according to claim 15, wherein the emissive layer comprises the at least one organometallic compound.

17. The organic light-emitting device according to claim 16, wherein the emissive layer further comprises a host.

18. The organic light-emitting device according to claim 16, wherein the emissive layer emits green light having a maximum emission wavelength of 490 nm to 550 nm.

19. The organic light-emitting device according to claim 15, wherein the first electrode is an anode, the second electrode is a cathode, the organic layer further comprises a hole transport region arranged between the first electrode and the emissive layer, and an electron transport region arranged between the emissive layer and the second electrode, wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and wherein the electron transport region comprises 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 15 to 19.

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