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

Abstract

Disclosed are an organometallic compound, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device. The organometallic compound is represented by Formula 1, where M1 is a transition metal, L1 is a ligand represented by Formula 1A, L2 is a ligand represented by Formula 1B, and n1 and n2 are each independently 1 or 2, where X1 is C or N, X2 is C or N, X3 is C or N, and X4 is C or N; x31 is C (R31) or N, and X34 is C (R34) or N; y1 is O, S or Se; r32 and R33 are each independently deuterium, a substituted C1-C60 alkyl group comprising deuterium, a substituted C3-C10 cycloalkyl group comprising deuterium, a substituted C6-C60 aryl group comprising deuterium, or a substituted C1-C60 heteroaryl group comprising deuterium; and the remaining descriptions of Formulae 1A and 1B are as provided herein. Formula 1M1 (L1) n1 (L2) n2 # imgabs0 #

Description

[0001] Cross-reference to related applications

[0002] This application claims the priority and benefits of Korean Patent Application No. 10-2023-0197632, filed with the Korean Intellectual Property Office on December 29, 2023, and all benefits arising therefrom, the entire content of which is incorporated herein by reference. Technical Field

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

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

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

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

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

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

[0009] Formula 1

[0010] M1(L1) n1 (L2) n2

[0011] Wherein, in Formula 1,

[0012] M1 is a transition metal,

[0013] L1 is a ligand represented by Formula 1A,

[0014] L2 is a ligand represented by Formula 1B, and

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

[0016] Formula 1A

[0017]

[0018] Formula 1B

[0019]

[0020] wherein, in Formulas 1A and 1B,

[0021] Ring CY1 is a 5-membered heterocyclic group, a 5-membered heterocyclic group fused to a C5-C 30 carbocyclic group, or a 5-membered heterocyclic group fused to a C1-C 30 heterocyclic group,

[0022] Ring CY2 and Ring CY4 are each independently a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group,

[0023] X1 is C or N, X2 is C or N, X3 is C or N, and X4 is C or N,

[0024] X 31 is C(R 31 ) or N, and X 34 is C(R 34 ) or N,

[0025] 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,

[0026] Y1 is O, S or Se,

[0027] R1, R2, R4, R 31 、R 34 、and R 41 to R 44 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60Alkynyl, 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, 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),

[0028] R 32 and R 33 each independently is deuterium, substituted C1-C including deuterium 60 alkyl, substituted C3-C including deuterium 10 cycloalkyl, substituted C6-C including deuterium 60 aryl, or substituted C1-C including deuterium 60 heteroaryl,

[0029] Two or more adjacent ones of a plurality of R1s optionally bond to each other to form a substituted or unsubstituted C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group,

[0030] Two or more adjacent ones of a plurality of R2s optionally bond together to form a substituted or unsubstituted C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group,

[0031] Two or more adjacent ones of a plurality of R4s may optionally be bonded together to form a substituted or unsubstituted C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group,

[0032] R1, R2, R4, R 31 , R 34 , and R 41 to R 44 Two or more adjacent ones may optionally be bonded together to form a substituted or unsubstituted C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group,

[0033] b1, b2 and b4 can each independently be an integer from 0 to 10,

[0034] * and *' each represent a binding site to M1,

[0035] 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 The substituents of substituted monovalent non-aromatic fused polycyclic groups and substituted monovalent non-aromatic fused heteropolycyclic groups are each independently:

[0036] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, or C1-C 60 alkylthio;

[0037] C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, or C1-C 60 alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 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, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 ), -Ge(Q 11 )(Q 12 )(Q 13 ), -N(Q 14 )(Q 15 ), -B(Q 16 )(Q 17 ), -P(Q 18 )(Q 19 ), -P(=O)(Q 18 )(Q 19 ), or a combination thereof;

[0038] 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;

[0039] C3-C each substituted with at least one of the following 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: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C1-C 60 alkylthio, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C7-C 60 arylalkyl, C6-C 60 aryloxy, C6-C60 Arylthio group, C1-C 60 Heteroaryl group, C2-C 60 Alkyl heteroaryl group, C2-C 60 Heteroarylalkyl group, C1-C 60 Heteroaryloxy group, C1-C 60 Heteroarylthio group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(Q 28 )(Q 29 )、-P(=O)(Q 28 )(Q 29 )、or a combination thereof; or

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

[0041] Q1 to Q9, Q 11 to Q 19 、Q 21 to Q 29 、and Q 31 to Q 39 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 alkyl group, substituted or unsubstituted C2-C 60 alkenyl group, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C1-C60 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.

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

[0043] The at least one organic metal compound represented by Formula 1 may be included in the emission layer of the organic layer, and the at least one organic metal compound represented by Formula 1 included in the emission layer may act as a dopant. BRIEF DESCRIPTION OF THE DRAWINGS

[0044] By the following detailed description taken in conjunction Figure 1 with the accompanying drawings, the above and other aspects, features, and advantages of some exemplary embodiments will become more apparent, Figure 1 which is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments. DETAILED DESCRIPTION

[0045] Exemplary embodiments will now be described in further detail, with examples illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout the specification. In this regard, the present exemplary embodiments may have different forms and should not be construed as limited to the detailed description set forth herein. Accordingly, the exemplary embodiments are described below only by referring to the accompanying drawings to illustrate some aspects and features. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. The phrase "at least one (kind of)" when preceding or following a list of elements modifies the entire list of elements and not individual elements of the list.

[0046] The terms used herein are for the purpose of describing one or more exemplary embodiments only and are not intended to be limiting. As used herein, the singular forms "a", "an" and "the" are also intended to include the plural forms unless the context clearly dictates otherwise. The term "or" means "and / or". It will be further understood that the terms "comprises" or "comprising", when used in this specification, specify the presence of stated features, regions, wholes, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, regions, wholes, steps, operations, elements, components, and / or groups thereof.

[0047] 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 parts, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or part from another. Thus, without departing from the teachings of the present embodiment, the first element, component, region, layer, or part discussed below may be referred to as the second element, component, region, layer, or part.

[0048] Exemplary embodiments are described herein with reference to cross-sectional views that are schematic illustrations of idealized embodiments. As such, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are to be expected. Accordingly, the embodiments described herein should not be construed as limited to the specific shapes of the regions as illustrated herein, but include deviations in shapes resulting from, for example, manufacturing. For example, regions illustrated or described as flat may typically have rough and / or non-linear features. Also, sharp corners illustrated may be rounded. Thus, the regions shown in the figures are schematic in nature and their shapes are not intended to illustrate the exact shape of the regions and are not intended to limit the scope of the claims.

[0049] It will be understood that when an element is referred to as being “on” another element, it can be in direct contact with the other element or there can be intervening elements therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements.

[0050] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the present disclosure and the relevant art, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

[0051] As used herein, “about” or “approximately” includes the stated value and means within an acceptable deviation range for the particular value as determined by one of ordinary skill in the art in view of the measurements discussed and the error associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations of the stated value, or within ±10% or 5%.

[0052] One aspect provides an organometallic compound represented by Formula 1:

[0053] Formula 1

[0054] M1(L1) n1 (L2) n2

[0055] Wherein M1 in Formula 1 is a transition metal.

[0056] For example, M1 can be a first-row transition metal of the periodic table, a second-row transition metal of the periodic table, or a third-row transition metal of the periodic table.

[0057] In one or more embodiments, M1 can be iridium, platinum, palladium, gold, osmium, titanium, zirconium, hafnium, europium, terbium, thulium, or rhodium.

[0058] In one or more embodiments, M1 can be iridium, platinum, osmium, or rhodium.

[0059] In one or more embodiments, M1 can be iridium.

[0060] In Formula 1, n1 is 1 or 2, and n2 is 1 or 2.

[0061] In one or more embodiments, the sum of n1 and n2 can be 2 or 3.

[0062] In one or more embodiments, M1 can be iridium, and the sum of n1 and n2 can be 3.

[0063] In one or more embodiments, M1 can be platinum, and the sum of n1 and n2 can be 2.

[0064] In Formula 1, L1 is a ligand represented by Formula 1A:

[0065] Formula 1A

[0066]

[0067] Wherein, in Formula 1A, X1 is C or N, and X2 is C or N.

[0068] In one or more embodiments, X1 can be N, and X2 can be C.

[0069] In Formula 1A, ring CY1 is a 5-membered heterocyclic group; a 5-membered heterocyclic group fused to a C5-C 30 carbocyclic group; or a 5-membered heterocyclic group fused to a C1-C 30 heterocyclic group.

[0070] In one or more embodiments, ring CY1 can be a pyrrole group, an imidazole group, a pyrazole group, an oxazole group, an indole group, an azaindole group, a benzopyrazole group, a benzimidazole group, or a benzoxazole group.

[0071] In Formula 1A, ring CY2 is a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group.

[0072] In one or more embodiments, ring CY2 can be a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

[0073] In one or more embodiments, in Formula 1A, ring CY1 can be an imidazole group or a benzimidazole group, and ring CY2 can be a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0074] In one or more embodiments, the moiety represented by in Formula 1A can be a group represented by one of Formulas CY(1)-1 to CY(1)-3:

[0075]

[0076] Among them, in Formulas CY(1)-1 to CY(1)-3,

[0077] X 11 may be C(R 11a ), C(R 11a )(R 11b ), N, or N(R 11a ),

[0078] X 12 may be C(R 12a ), C(R 12a )(R 12b ), N, or N(R 12a ),

[0079] X 13 may be C(R 13a ), C(R 13a )(R 13b ), N, or N(R 13a ),

[0080] Ring CY 10 may be a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group,

[0081] R 10 、R 11a 、R 11b 、R 12a 、R 12b 、R 13a and R 13b may each independently be as defined herein for R1,

[0082] b10 may be an integer from 1 to 10,

[0083] represents a single bond or a double bond,

[0084] * represents the binding site to M1, and

[0085] *” represents the binding site to an adjacent atom.

[0086] In one or more embodiments, in Formulas CY(1)-2 and CY(1)-3, ring CY 10 may be a benzene group, a naphthalene group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0087] In one or more embodiments, the portion represented by in Formula 1A may be a group represented by one of Formulas CY(2)-1 to CY(2)-16:

[0088]

[0089] Among them, in Formulas CY(2)-1 to CY(2)-16,

[0090] R 21 to R 24 can each independently be the same as described for R2, provided that R 21 to R 24 is not hydrogen,

[0091] *' represents the binding site to M1, and

[0092] *” represents the binding site to an adjacent atom.

[0093] In one or more embodiments, L1 can be a ligand represented by Formula 1A-1 or 1A-2:

[0094]

[0095] Among them, in Formulas 1A-1 and 1A-2,

[0096] R 10 to R 13 can each independently be as defined for R1,

[0097] R 20 can be as defined herein for R2,

[0098] b10 and b20 can each independently be an integer from 1 to 4, and

[0099] * and *' each represent the binding site to M1.

[0100] In one or more embodiments, R 11 can be a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C3-C 10 cycloalkenyl, or a substituted or unsubstituted C6-C 60 aryl. For example, R 11 can be a substituted C6-C 60 aryl, for example, a phenyl, naphthyl, or biphenyl substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, nitro, C1-C 20 alkyl (for example, C1-C 10 linear alkyl or C3-C 10 branched alkyl), C1-C 20 alkoxy, C1-C 20 alkylthio, or a combination thereof.

[0101] In Formula 1, L2 is a ligand represented by Formula 1B.

[0102] Formula 1B

[0103]

[0104] Wherein, in Formula 1B, X3 is C or N, and X4 is C or N.

[0105] In one or more embodiments, X3 can be N, and X4 can be C.

[0106] In Formula 1B, ring CY4 is a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group.

[0107] In one or more embodiments, ring CY4 can be a phenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a phenanthrolinyl group, a benzofuranyl group, a benzothiophenyl group, a fluorene group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, an azafluorene group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or an azadibenzosilolyl group.

[0108] In Formula 1B, 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 are each as defined herein.

[0109] In Formula 1B, Y1 is O, S or Se.

[0110] In one or more embodiments, L2 can be a ligand represented by one of Formulas 1B-1 to 1B-4:

[0111]

[0112] Wherein, in Formulas 1B-1 to 1B-4,

[0113] X3, X4, X 31 , X 34 , X 41 to X 44 , Y1, R32 and R 33 may each be as defined herein,

[0114] E1 may be C(Z1) or N, E2 may be C(Z2) or N, E3 may be C(Z3) or N, and E4 may be C(Z4) or N,

[0115] E5 may be C(Z5) or N, E6 may be C(Z6) or N, E7 may be C(Z7) or N, and E8 may be C(Z8) or N,

[0116] Z1 to Z8 may each independently be as defined herein for R4, and

[0117] * and *' each represent a binding site to M1.

[0118] In one or more embodiments, L2 may be a ligand represented by one of Formulas 1B(1)-1 to 1B(1)-4:

[0119]

[0120] wherein, in Formulas 1B(1)-1 to 1B(1)-4,

[0121] X3, X4, X 41 to X 44 , Y1, R 31 , R 32 , R 33 and R 34 may each be as defined herein,

[0122] R 40 may be as defined herein for R4,

[0123] b40 may be an integer from 1 to 4,

[0124] b41 may be an integer from 1 to 6, and

[0125] * and *' each represent a binding site to M1.

[0126] In Formulas 1A and 1B, R1, R2, R4, R 31 , R 34 , and R 41 to R 44 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a substituted or unsubstituted C1-C 60 alkyl, a substituted or unsubstituted C2-C 60 alkenyl, a substituted or unsubstituted C2-C 60Alkynyl, 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, 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), where Q1 to Q9 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkylaryl, substituted or unsubstituted C7-C 60Arylalkyl, 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.

[0127] In one or more embodiments, R1, R2, R4, R 31 , R 34 , and R 41 to R 44 may each independently be:

[0128] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 alkyl, C1-C 20 alkoxy, or C1-C 20 alkylthio;

[0129] C1-C 20 alkyl, C1-C 20 alkoxy, or C1-C 20 alkylthio, each substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or a combination thereof;

[0130] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, a radical, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, or imidazopyrimidinyl;

[0131] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, each substituted with at least one of the following a radical, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, C1-C 20 alkyl, C1-C 20 alkoxy, C1-C 20 alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, a radical, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or a combination thereof; or

[0132] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=O)(Q8)(Q9), and

[0133] Q1 to Q9 may each independently be:

[0134] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0135] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0136] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of the following: deuterium, C1-C 10 alkyl, phenyl, or a combination thereof.

[0137] In one or more embodiments, R1, R2, R4, R 31 、R 34 、and R 41 to R 44 may each independently be:

[0138] hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, or C1-C 60 alkylthio;

[0139] 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

[0140] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), or -N(Q4)(Q5):

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149] Wherein, 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, * represents the binding site to an adjacent atom, "Ph" represents a phenyl group, "TMS" represents a trimethylsilyl group, and "TMG" represents a trimethylgermyl group.

[0150] In one or more embodiments, in Formula 1B, at least one of R4 and R 41 to R 44 may be deuterium, a substituted C1-C 60 alkyl group including deuterium, a substituted C3-C 10 cycloalkyl group including deuterium, a substituted C6-C 60 aryl group, or a substituted C1-C 60 heteroaryl group including deuterium.

[0151] In one or more embodiments, at least one of R4 and R 41 to R 44 may be

[0152] deuterium; or a C1-C 10alkyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl; or

[0153] each independently is deuterium, and at least one C1-C 10 alkyl-substituted cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl.

[0154] In Formulas 1A and 1B, R 32 and R 33 are each independently deuterium, a substituted C1-C 60 alkyl containing deuterium, a substituted C3-C 10 cycloalkyl containing deuterium, a substituted C6-C 60 aryl, or a substituted C1-C 60 heteroaryl containing deuterium.

[0155] In one or more embodiments, R 32 and R 33 can each independently be:

[0156] -CD3, -CD2H, or -CDH2;

[0157] C1-C 20 alkyl substituted with: i) at least one substituent in Group RA, or ii) at least one substituent in Group RA and at least one substituent in Group RB;

[0158] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, phenyl, naphthyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, each independently substituted with a group selected from the group consisting of a radical, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, or imidazopyrimidinyl: i) at least one substituent in group RA, or ii) at least one substituent in group RA and at least one substituent in group RB:

[0159] group RA

[0160] deuterium; -CD3; -CD2H; -CDH2; or a C1-C alkyl group, each substituted with at least one deuterium 10 alkyl, C1-C 10 alkoxy, C1-C 10 alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, a group selected from the group consisting of a radical, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, or imidazopyrimidinyl; or a combination thereof;

[0161] group RB

[0162] -F, -Cl, -Br, -I, -SF5, -CF3, -CF2H, -CFH2, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, a radical, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, or a combination thereof.

[0163] In one or more embodiments, R 32 and R 33 may each independently be -CD3, -CD2H, -CDH2, or a group represented by one of Formulas 8-1 to 8-15:

[0164]

[0165] wherein, in Formulas 8-1 to 8-15, * represents a binding site to an adjacent atom. In one or more embodiments, R 32 and R 33 may each independently be -CD3, -CD2H, -CDH2, or a group represented by one of Formulas 8-1 to 8-14.

[0166] Two or more of the plurality of R1s in Formula 1A are optionally 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.

[0167] In Formula 1A, two or more of the plurality of R2s are optionally bonded together to form a substituted or unsubstituted C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group.

[0168] In Formula 1B, two or more of the plurality of R4s are optionally bonded together to form a substituted or unsubstituted C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group.

[0169] In Formulas 1A and 1B, two or more of R1, R2, R4, R 31 , R 34 , and R 41 to R 44 are optionally bonded together to form a substituted or unsubstituted C5-C 30A carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group.

[0170] In Formulas 1A and 1B, b1, b2, and b4 are each independently an integer from 0 to 10, such as an integer from 1 to 10, an integer from 1 to 6, or an integer from 1 to 4.

[0171] In Formulas 1A and 1B, * and *' each represent a binding site to M1.

[0172] In one or more embodiments, the organometallic compound represented by Formula 1 can be represented by one of Formulas 1-1 to 1-4:

[0173]

[0174]

[0175] wherein, in Formulas 1-1 to 1-4,

[0176] M1, n1, n2, Y1, R 31 to R 34 , and R 41 to R 44 can each be as defined herein,

[0177] R 10 and R 11 can each independently be as defined herein for R1,

[0178] R 20 can be as defined herein for R2,

[0179] R 51 and R 52 can each independently be as defined herein for R4,

[0180] b10, b20, b50, and b52 can each independently be an integer from 1 to 4, and

[0181] b51 can be 1 or 2.

[0182] In one or more embodiments, in Formulas 1-1 to 1-4, R 31 and R 34 can each be hydrogen, and R 32 and R 33 can each independently be -CD3, -CD2H, -CDH2, or a group represented by one of Formulas 8-1 to 8-15. In one or more embodiments, in Formulas 1-1 to 1-4, R 31 and R 34 can each be hydrogen, and R 32 and R 33Each may independently be -CD3, -CD2H, -CDH2, or a group represented by one of Formulas 8-1 to 8-14.

[0183] In one or more embodiments, the organometallic compound represented by Formula 1 may be one of Compounds 1 to 72:

[0184]

[0185]

[0186]

[0187]

[0188]

[0189] In one or more embodiments, the organometallic compound represented by Formula 1 may be electrically neutral.

[0190] The organometallic compound represented by Formula 1 satisfies the structure represented by Formula 1 described herein and includes ligands having the structures of Formulas 1A and 1B, wherein Formula 1B includes R 32 and R 33 , R 32 and R 33 are groups including deuterium. Due to this structure, the organometallic compound of Formula 1 has excellent luminescent properties and thus may have properties suitable for use as a luminescent material with high color purity by controlling the emission wavelength range.

[0191] In addition, the organometallic compound of Formula 1 has excellent electron mobility, and thus an electronic device including at least one of the organometallic compounds represented by Formula 1, such as an organic light-emitting device, may have a low driving voltage, a high external quantum efficiency, and / or a long lifespan.

[0192] In one or more embodiments, the maximum emission wavelength (emission peak wavelength or peak emission wavelength, λ max ) in the emission spectrum or electroluminescence spectrum of the organometallic compound represented by Formula 1 may be about 490 nanometers (nm) to about 550 nm, about 500 nm to about 540 nm, about 510 nm to about 535 nm, or about 510 nm to about 530 nm.

[0193] The method for synthesizing the organometallic compound represented by Formula 1 may be recognized by those of ordinary skill in the art by referring to the synthesis examples provided herein.

[0194] Therefore, the organometallic compound represented by Formula 1 can be suitable for use in the organic layer of an organic light-emitting device, for example, as a dopant in the emission layer of the organic layer. Accordingly, on the other hand, an organic light-emitting device is provided, which includes a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer; and wherein the organic layer includes at least one of the organometallic compounds represented by Formula 1.

[0195] When the organic light-emitting device includes an organic layer containing at least one of the aforementioned organometallic compounds represented by Formula 1, characteristics such as excellent driving voltage, excellent maximum external quantum efficiency, and / or long lifespan can be presented.

[0196] The organometallic compound represented by Formula 1 can be used between the electrode pair of the organic light-emitting device. For example, at least one of the organometallic compounds represented by Formula 1 can be included in the emission layer. Here, the organometallic compound can be used as a dopant, and the emission layer can further include a host. When the emission layer further includes a host, based on weight, the amount of the host in the emission layer can be greater than the amount of the at least one organometallic compound represented by Formula 1 in the emission layer.

[0197] In one or more embodiments, the emission layer can emit green light. For example, the emission layer can emit green light having a maximum emission wavelength of about 490 nm to about 550 nm, about 500 nm to about 540 nm, or about 510 nm to about 535 nm.

[0198] The expressions “(the organic layer) includes at least one of the organometallic compounds represented by Formula 1” and “(the organic layer) includes at least one organometallic compound represented by Formula 1” can be used interchangeably herein and can include cases where “(the organic layer) includes the same organometallic compound represented by Formula 1” and cases where “(the organic layer) includes two or more different types of organometallic compounds represented by Formula 1”.

[0199] For example, the organic layer can include only Compound 1 as the at least one of the organometallic compounds represented by Formula 1. In this regard, Compound 1 can be included in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer can include Compound 1 and Compound 2 as the at least one of the organometallic compounds represented by Formula 1. In this embodiment, Compound 1 and Compound 2 can be present in the same layer (for example, both Compound 1 and Compound 2 can be present in the emission layer).

[0200] The first electrode can be an anode as a hole injection electrode, and the second electrode can be a cathode as an electron injection electrode, or the first electrode can be a cathode as an electron injection electrode, and the second electrode can be an anode as a hole injection electrode.

[0201] In one or more embodiments, in an organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode, where 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.

[0202] As used herein, the term "organic layer" refers to a single layer or multiple layers disposed between the first electrode and the second electrode of an organic light-emitting device. In addition to organic compounds, the "organic layer" may further include organometallic complexes containing metals.

[0203] Figure 1 FIG. is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Hereinafter, regarding Figure 1 The structure and manufacturing method of an organic light-emitting device 10 according to one or more embodiments of the present disclosure will be described. The organic light-emitting device 10 has a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are sequentially stacked in the stated order.

[0204] A substrate may be additionally disposed under the first electrode 11 or on the second electrode 19. For use as a substrate, substrates commonly used in organic light-emitting devices may be used, such as glass substrates or transparent plastic substrates having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or waterproofness.

[0205] The first electrode 11 may be formed by, for example, depositing or sputtering a material for forming the first electrode 11 onto a substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive semi-reflective electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0206] The first electrode 11 may have a single-layer structure or a multi-layer structure including multiple layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the embodiments are not limited thereto.

[0207] The organic layer 15 is disposed on the first electrode 11.

[0208] The organic layer 15 may include an emission layer, and may further include a hole transport region and an electron transport region.

[0209] The hole transport region may be disposed between the first electrode 11 and the emission layer.

[0210] 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.

[0211] The hole transport region may include only a hole injection layer or a hole transport layer. The hole transport region may have a hole injection layer / hole transport layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, where the constituent layers are stacked in the stated order starting from the first electrode 11.

[0212] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using various methods such as vacuum deposition, spin coating, casting, and / or Langmuir-Blodgett (LB) deposition, but the embodiments are not limited thereto.

[0213] When the hole injection layer is formed by a vacuum deposition method, the deposition conditions may vary depending on the compound used as the material for forming the hole injection layer, the desired structure and thermal properties of the hole injection layer, etc. For example, the deposition temperature may be about 100 °C to about 500 °C, the vacuum pressure may be about 10 -8 torr to about 10 -3 torr, and the deposition rate may be about 0.01 Å / second ( / second) to about / second, but the embodiments are not limited thereto.

[0214] When the hole injection layer is formed by a spin coating method, the coating conditions may vary depending on the compound used as the material for forming the hole injection layer, the desired structure and thermal properties of the hole injection layer, etc. For example, the coating rate may be about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and the temperature for heat treatment to remove the solvent after coating may be about 80 °C to about 200 °C, but the embodiments are not limited thereto.

[0215] In this regard, the conditions for forming the hole transport layer and the electron blocking layer can be understood by referring to the conditions for forming the hole injection layer.

[0216] The hole transport region may include at least one of, for example, the following: 4,4',4”-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), β-NPB, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4'-cyclohexylidenebis[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-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, or a compound represented by Formula 202, but the embodiments are not limited thereto:

[0217]

[0218] Formula 201

[0219]

[0220] Formula 202

[0221]

[0222] Wherein, in Formula 201, Ar 101 and Ar 102 may each independently be:

[0223] phenylene, annulenylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthylene, fluorenylene, phenalenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrenylene, or annulene; or

[0224] phenylene, annulenylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthylene, fluorenylene, phenalenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrenylene, A base, a naphthacene diyl, a picene diyl, a perylene diyl, or a pentacene diyl: deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a C1-C 60 alkylthio group, a C3-C 10 cycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C7-C 60 alkylaryl group, a C7-C 60 arylalkyl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, a C2-C 60 alkylheteroaryl group, a C2-C 60 heteroarylalkyl group, a C1-C 60 heteroaryloxy group, a C1-C 60 heteroarylthio group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or a combination thereof.

[0225] In Formula 201, xa and xb can each independently be an integer from 0 to 5, or xa and xb can each independently be 0, 1, or 2. For example, xa can be 1 and xb can be 0, but the embodiments are not limited thereto.

[0226] In Formulas 201 and 202, R 101 to R 108 , R 111 to R 119 , and R 121 to R 124 can each independently be:

[0227] hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 10 alkyl group (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), a C1-C 10 alkoxy group (e.g., methoxy, ethoxy, propoxy, butoxy, pentyloxy, etc.), or a C1-C 10 alkylthio group;

[0228] each is C1-C substituted by at least one of the following 10 alkyl, C1-C 10 alkoxy, or C1-C 10 alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, or a combination thereof;

[0229] phenyl, naphthyl, anthryl, fluorenyl, or pyrenyl; or

[0230] each of phenyl, naphthyl, anthryl, fluorenyl, or pyrenyl substituted by at least one of the following: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, C1-C 10 alkyl, C1-C 10 alkoxy, C1-C 10 alkylthio, or a combination thereof, but the embodiments are not limited thereto.

[0231] In Formula 201, R 109 may be:

[0232] phenyl, naphthyl, anthryl, or pyridyl; or

[0233] each of phenyl, naphthyl, anthryl, or pyridyl substituted by at least one of the following: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, C1-C 20 alkyl, C1-C 20 alkoxy, C1-C 20 alkylthio, phenyl, naphthyl, anthryl, pyridyl, or a combination thereof.

[0234] In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but the embodiments are not limited thereto:

[0235] Formula 201A

[0236]

[0237] wherein, in Formula 201A, R 101 , R 111 , R 112 and R 109 may each be as defined herein.

[0238] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include at least one of Compounds HT1 to HT20, but the embodiments are not limited thereto:

[0239]

[0240]

[0241]

[0242] The thickness of the hole transport region may be about to about For example, about to about When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about to about For example, about to about And the thickness of the hole transport layer may be about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in the driving voltage.

[0243] In addition to the above materials, the hole transport region may further include a charge generation material for improving the conduction performance. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region.

[0244] The charge generation material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, or a cyanide-containing compound, but the embodiments are not limited thereto. Non-limiting examples of the p-dopant include quinone derivatives such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (F6-TCNNQ), etc.; metal oxides such as tungsten oxide, molybdenum oxide, etc.; or cyanide-containing compounds such as Compound HT-D1 or F12, but the embodiments are not limited thereto:

[0245]

[0246] The hole transport region may further include a buffer layer.

[0247] The buffer layer may compensate for the optical resonance distance according to the wavelength of the light emitted from the emission layer, and thus, the efficiency of the formed organic light-emitting device may be improved.

[0248] Meanwhile, when the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may be selected from the materials used for the aforementioned hole transport region and the host material to be described later, but the embodiments are not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may be mCP to be described herein.

[0249] Then, the emission layer can be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied when forming the hole injection layer, although the deposition or coating conditions may vary depending on the material to be used.

[0250] The emission layer may include a host and a dopant, and the dopant may include at least one of the organometallic compounds represented by Formula 1.

[0251] The host may include at least one of 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphthalen-2-yl)anthracene (TBADN), 9,10-di(naphthalen-2-yl)anthracene (ADN) (also referred to as "DNA"), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 1,3,5-tris(carbazol-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:

[0252]

[0253] In one or more embodiments, the host may include a compound represented by Formula 301, but the embodiments are not limited thereto:

[0254] Formula 301

[0255]

[0256] Wherein, in Formula 301, Ar 111 and Ar 112 may each independently be:

[0257] phenylene, naphthylene, phenanthrylene, or pyrenylene; or

[0258] phenylene, naphthylene, phenanthrylene, or pyrenylene each substituted with at least one of the following: phenyl, naphthyl, anthracenyl, or a combination thereof.

[0259] In Formula 301, Ar 113 to Ar 116Each may independently be:

[0260] C1-C 10 alkyl, phenyl, naphthyl, phenanthryl, or pyrenyl; or

[0261] phenyl, naphthyl, phenanthryl, or pyrenyl, each substituted with at least one of: phenyl, naphthyl, anthracenyl, or a combination thereof.

[0262] In Formula 301, g, h, i, and j may each independently be an integer from 0 to 4, and g, h, i, and j may each independently be, for example, 0, 1, or 2.

[0263] In Formula 301, Ar 113 to Ar 116 may each independently be:

[0264] C1-C substituted with at least one of: 10 alkyl: phenyl, naphthyl, anthracenyl, or a combination thereof;

[0265] phenyl, naphthyl, anthracenyl, pyrenyl, phenanthryl, or fluorenyl;

[0266] phenyl, naphthyl, anthracenyl, pyrenyl, phenanthryl, or fluorenyl, each substituted with at least one of: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C1-C 60 alkylthio, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthryl, fluorenyl, or a combination thereof; or

[0267] a group represented by the following formula:

[0268]

[0269] However, the embodiments are not limited thereto.

[0270] In one or more embodiments, the host may include a compound represented by Formula 302, however, the embodiments are not limited thereto:

[0271] Formula 302

[0272]

[0273] Wherein, in Formula 302, Ar 122 to Ar 125 may each be as defined for Ar in Formula 301 113 as defined.

[0274] In Formula 302, Ar 126 and Ar 127 can each independently be C1-C 10 alkyl (e.g., methyl, ethyl, or propyl).

[0275] In Formula 302, k and l can each independently be an integer from 0 to 4. For example, k and l can each independently be 0, 1, or 2.

[0276] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer, and / or a blue emission layer. Due to the structure in which the red emission layer, the green emission layer, and / or the blue emission layer are stacked therein, the emission layer can emit white light.

[0277] When the emission layer includes a host and a dopant, based on 100 parts by weight of the host of the emission layer, the amount of the dopant in the emission layer can be about 0.01 part by weight to about 15 parts by weight, but the embodiments are not limited thereto.

[0278] The thickness of the emission layer can be about to about For example, about to about When the thickness of the emission layer is within these ranges, excellent light-emitting characteristics can be obtained without a significant increase in the driving voltage.

[0279] The electron transport region can be disposed on the emission layer.

[0280] The electron transport region can include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0281] For example, the electron transport region can have a hole blocking layer / electron transport layer / electron injection layer structure, or an electron transport layer / electron injection layer structure, but the embodiments are not limited thereto. The electron transport layer can have a multi-layer structure including multiple layers or a single-layer structure.

[0282] The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region can be understood by referring to the conditions for forming the hole injection layer.

[0283] When the electron transport region includes a hole blocking layer, the hole blocking layer can 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-hydroxyquinolinato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum (BAlq), but the embodiments are not limited thereto:

[0284]

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

[0286] 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-hydroxyquinolinato-N1,O8)-(1,1'-biphenyl-4-olato) aluminum (BAlq), 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), or 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), but the embodiments are not limited thereto:

[0287]

[0288] The electron transport layer may include at least one of compounds ET1 to ET25, but the embodiments are not limited thereto:

[0289]

[0290]

[0291] The thickness of the electron transport layer may be about to about For example, about to about When the thickness of the electron transport layer is within these ranges, satisfactory electron transport characteristics can be obtained without a significant increase in the driving voltage.

[0292] In addition to the foregoing materials, the electron transport layer may further include a metal-containing material.

[0293] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium 8-hydroxyquinoline, Liq) or ET-D2, but the embodiments are not limited thereto:

[0294]

[0295] The electron transport region may further include an electron injection layer that promotes the injection of electrons from the second electrode 19.

[0296] The electron injection layer may include Liq, LiF, NaCl, CsF, Li2O, BaO, or a combination thereof.

[0297] The thickness of the electron injection layer may be about to about For example, about to about When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.

[0298] The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. The material for forming the second electrode 19 may be a metal, an alloy, a conductive compound, or a combination thereof, each having a relatively low work function. For example, the material for forming the second electrode 19 may include lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. For manufacturing a top-emission type light-emitting device, a transmissive electrode formed of ITO or IZO can be used as the second electrode 19.

[0299] In the above, an organic light-emitting device has been described with reference to Figure 1 However, the embodiments are not limited thereto.

[0300] On the other hand, a diagnostic composition is provided, which includes at least one of the foregoing organometallic compounds represented by Formula 1.

[0301] The organometallic compound represented by Formula 1 may be capable of providing high luminous efficiency, and thus a diagnostic composition including at least one of the organometallic compounds represented by Formula 1 may have high diagnostic efficiency.

[0302] The diagnostic composition can be used in various applications including diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc., but the embodiments are not limited thereto.

[0303] As used herein, the term "C1-C 60 alkyl" refers to a straight-chain or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. C1-C 60 alkyl may be C1-C 20 alkyl, C1-C 10 alkyl, C1-C6 alkyl, or C1-C3 alkyl. Each of the alkyls may be straight-chain or branched. In the case of a branched alkyl, the lower limit of the carbon number range of each of the above alkyls is 3. C1-C 60Non-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, the term "C1-C 60 alkylene" refers to a divalent group having the same structure as a C1-C 60 alkyl group.

[0304] As used herein, the term "C1-C 60 alkoxy" refers to a monovalent group represented by -OA 101 (where A 101 is a C1-C 60 alkyl group), and non-limiting examples thereof include methoxy, ethoxy, isopropoxy, etc. As used herein, the term "C1-C 60 alkylthio" refers to a monovalent group represented by -SA 101 (where A 101 is a C1-C 60 alkyl group).

[0305] As used herein, the term "C2-C 60 alkenyl" refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond at the middle or end of a C2-C 60 alkyl group, and non-limiting examples thereof include vinyl, propenyl, butenyl, etc. As used herein, the term "C2-C 60 alkenylene" refers to a divalent group having the same structure as a C2-C 60 alkenyl group.

[0306] As used herein, the term "C2-C 60 alkynyl" refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond at the middle or end of a C2-C 60 alkyl group, and non-limiting examples thereof include ethynyl, propynyl, etc. As used herein, the term "C2-C 60 alkynylene" refers to a divalent group having the same structure as a C2-C 60 alkynyl group.

[0307] As used herein, the term "C3-C 10 cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms as ring-forming atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc. As used herein, the term "C3-C 10 cycloalkylene" refers to a divalent group having the same structure as a C3-C 10 cycloalkyl group.

[0308] As used herein, the term "C1-C10 "Heterocycloalkyl" refers to a monovalent saturated cyclic group having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as ring-forming atoms and 1 to 10 carbon atoms as ring-forming atoms, and non-limiting examples thereof include tetrahydrofuranyl, tetrahydrothienyl, etc. As used herein, the term "C1-C 10 "Subheterocycloalkyl" refers to a divalent group having the same structure as C1-C 10 heterocycloalkyl.

[0309] As used herein, the term "C3-C 10 "Cycloalkenyl" refers to a monovalent hydrocarbon ring group that includes 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and does not have aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, or cycloheptenyl. As used herein, the term "C3-C 10 "Subcycloalkenyl" refers to a divalent group having the same structure as C3-C 10 cycloalkenyl.

[0310] As used herein, the term "C1-C 10 "Heterocycloalkenyl" refers to a monovalent ring group that has at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as ring-forming atoms, 1 to 10 carbon atoms as ring-forming atoms, and at least one double bond and does not have aromaticity. C1-C 10 Non-limiting examples of heterocycloalkenyl include 2,3-dihydrofuranyl, 2,3-dihydrothienyl, etc. As used herein, the term "C1-C 10 "Subheterocycloalkenyl" refers to a divalent group having the same structure as C1-C 10 heterocycloalkenyl.

[0311] As used herein, the term "C6-C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic ring system with 6 to 60 carbon atoms as ring-forming atoms, and as used herein, the term "C6-C 60 "Subaryl" refers to a divalent group having a carbocyclic aromatic ring system with 6 to 60 carbon atoms as ring-forming atoms. C6-C 60 Non-limiting examples of aryl include phenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, yl, etc. When C6-C 60 aryl and C6-C 60 subaryl each include two or more rings, the rings may be fused to each other.

[0312] As used herein, the term "C7-C 60 "Alkylaryl" refers to a C6-C group substituted with at least one C1-C 54 alkyl59 Aryl. As used herein, the term "C7-C 60 arylalkyl" refers to a C1-C 59 alkyl that is substituted with at least one C6-C 54 aryl.

[0313] As used herein, the term "C1-C 60 heteroaryl" refers to a monovalent group having a heteroaromatic ring system having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring-forming atom and 1 to 60 carbon atoms as ring-forming atoms, and as used herein, the term "C1-C 60 heteroarylene" refers to a divalent group having a heteroaromatic ring system having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring-forming atom and 1 to 60 carbon atoms as ring-forming atoms. Non-limiting examples of C1-C 60 heteroaryl include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, etc. When C1-C 60 heteroaryl and C1-C 60 heteroarylene each include two or more rings, the rings may be fused to each other.

[0314] As used herein, the term "C2-C 60 alkylheteroaryl" refers to a C1-C 59 heteroaryl that is substituted with at least one C1-C 59 alkyl. As used herein, the term "C2-C 60 heteroarylalkyl" refers to a C1-C 59 alkyl that is substituted with at least one C1-C 59 heteroaryl.

[0315] As used herein, the term "C6-C 60 aryloxy" refers to -OA 102 (where A 102 is C6-C 60 aryl), and as used herein, the term "C6-C 60 arylthio" refers to -SA 103 (where A 103 is C6-C 60 aryl).

[0316] As used herein, the term "C1-C 60 heteroaryloxy" means -OA 104 (where A 104 is C1-C 60 heteroaryl), and as used herein, the term "C1-C 60"Heteroarylthio" means -SA 105 (wherein A 105 is C1-C 60 heteroaryl).

[0317] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) that has two or more rings fused to each other, has only carbon atoms as ring-forming atoms, and is not aromatic in its entire structure. Non-limiting examples of monovalent non-aromatic fused polycyclic groups include fluorenyl and the like. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group described above.

[0318] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms) that has two or more rings fused to each other, has heteroatoms selected from B, N, O, P, Si, S, Se, and Ge in addition to carbon atoms as ring-forming atoms, and is not aromatic in its entire structure. Non-limiting examples of monovalent non-aromatic fused heteropolycyclic groups include carbazolyl and the like. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.

[0319] As used herein, the term "C5-C 30 carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring-forming atoms. The C5-C 30 carbocyclic group can be a monocyclic group or a polycyclic group.

[0320] As used herein, the term "C1-C 30 heterocyclic group" refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge in addition to 1 to 30 carbon atoms as ring-forming atoms. The C1-C 30 heterocyclic group can be a monocyclic group or a polycyclic group.

[0321] 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 10Heterocycloalkyl, 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, substituted monovalent non-aromatic fused polycyclic group, and at least one of the substituents of the substituted monovalent non-aromatic fused heteropolycyclic group may be:

[0322] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio;

[0323] Each C1-C substituted by at least one of the following 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkylaryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-Ge(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(Q 18 )(Q 19 )、-P(=O)(Q 18 )(Q 19 )、or a combination thereof;

[0324] 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 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group;

[0325] Each of 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 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60Heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C1-C 60 alkylthio, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C7-C 60 arylalkyl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C2-C 60 heteroarylalkyl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(Q 28 )(Q 29 )、-P(=O)(Q 28 )(Q 29 )、or a combination thereof; or

[0326] -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q37 ) or -P(Q 38 )(Q 39 ) or -P(=O)(Q 38 )(Q 39 ), and

[0327] Q1 to Q9, Q 11 to Q 19 、Q 21 to Q 29 、and Q 31 to Q 39 may each independently be: hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a substituted or unsubstituted C1-C 60 alkyl, a substituted or unsubstituted C2-C 60 alkenyl, a substituted or unsubstituted C2-C 60 alkynyl, a substituted or unsubstituted C1-C 60 alkoxy, a substituted or unsubstituted C1-C 60 alkylthio, a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C1-C 10 heterocycloalkyl, a substituted or unsubstituted C3-C 10 cycloalkenyl, a substituted or unsubstituted C1-C 10 heterocycloalkenyl, a substituted or unsubstituted C6-C 60 aryl, a substituted or unsubstituted C7-C 60 alkylaryl, a substituted or unsubstituted C7-C 60 arylalkyl, a substituted or unsubstituted C6-C 60 aryloxy, a substituted or unsubstituted C6-C 60 arylthio, a substituted or unsubstituted C1-C 60 heteroaryl, a substituted or unsubstituted C2-C 60 alkylheteroaryl, a substituted or unsubstituted C2-C 60 heteroarylalkyl, a substituted or unsubstituted C1-C 60 heteroaryloxy, a substituted or unsubstituted C1-C 60 heteroarylthio, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0328] For example, Q1 to Q9, Q 11 to Q 19 、Q 21 to Q 29 、and Q 31 to Q 39Each may independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or a C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C1-C 60 alkylthio group, C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 60 heterocycloalkenyl group, C6-C 60 aryl group, C7-C 60 alkylaryl group, C7-C 60 arylalkyl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, C2-C 60 alkylheteroaryl group, C2-C 60 heteroarylalkyl group, C1-C 60 heteroaryloxy group, C1-C 60 heteroarylthio group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group: deuterium, C1-C 60 alkyl group, C3-C 10 cycloalkyl group, C6-C 60 aryl group, or a combination thereof.

[0329] Hereinafter, the organometallic compound represented by Formula 1 and the organic light-emitting device including the same according to one or more embodiments will be described in further detail with reference to synthetic examples and examples. However, the following examples are not intended to limit the scope of the present disclosure. The phrase "using B instead of A" used in describing the synthetic examples means that, in terms of molar equivalents, the amount of A used is the same as the amount of B used.

[0330] Examples

[0331] Synthetic Example 1: Synthesis of Compound 1

[0332]

[0333] Synthesis of Compound 1A

[0334] 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-benzo[d]imidazole (3.0 grams (g), 8.46 millimoles (mmol)) and iridium(III) chloride trihydrate (IrCl3(H2O)n , n = 3) (1.42 g, 4.03 mmol) was mixed with 90 milliliters (mL) of 2-ethoxyethanol and 30 mL of deionized (DI) water, and the mixed solution was stirred under reflux for 24 hours. Then, the reaction temperature was lowered to room temperature. The resulting solid was separated by filtration and washed thoroughly with water / methanol / hexane in the stated order, and then the obtained solid was dried in a vacuum oven to obtain 3.1 g (82% yield) of Compound 1A.

[0335] Synthesis of Compound 1B

[0336] Compound 1A (3.1 g, 1.66 mmol) was mixed with 120 mL of dichloromethane (DCM) to form a first solution. A second solution was prepared by combining silver trifluoromethanesulfonate (AgOTf) (0.89 g, 3.47 mmol) and 40 mL of methanol (MeOH). Then the second solution was combined with the first solution to form a reaction solution. The reaction solution was stirred at room temperature for 18 hours under conditions where light was blocked with aluminum foil. The resulting solid was removed by filtration through diatomaceous earth, and a solid (Compound 1B) was obtained by removing the solvent from the filtrate. The solid was then used in the next reaction without further purification.

[0337] Synthesis of Compound 1

[0338] Compound 1B (2.7 g, 2.43 mmol) and 4,5-bis(methyl-d3)-2-(naphtho[2,3-b]benzofuran-4-yl)pyridine (0.80 g, 2.43 mmol) were mixed with 25 mL of 2-ethoxyethanol and 25 mL of dimethylformamide (DMF), and the mixed solution was stirred at 120 °C for 24 hours. Then, the reaction temperature was lowered to room temperature. The solid obtained by removing the solvent under reduced pressure was purified by column chromatography (eluent: hexane and ethyl acetate) to obtain 0.84 g (28% yield) of Compound 1. This compound was confirmed by high-resolution mass spectrometry (HRMS(MALDI)) using matrix-assisted laser desorption ionization and high-performance liquid chromatography (HPLC) analysis.

[0339] HRMS(MALDI): For C 73 H 60 Calculated value for D6IrN5O: m / z 1227.5273; Measured value: 1227.5276.

[0340] Synthesis Example 2: Synthesis of Compound 7

[0341]

[0342] Compound 7 (0.88 g, 28% yield) was obtained in a similar manner to Synthesis Example 1, except that 4,5-bis(methyl-d3)-2-(phenanthro[3,2-b]benzofuran-11-yl)pyridine was used instead of 4,5-bis(methyl-d3)-2-(naphtho[2,3-b]benzofuran-4-yl)pyridine. The compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0343] HRMS (MALDI): For C 77 H 62 Calculated for D6IrN5O: m / z 1277.5430; Found: 1277.5433.

[0344] Synthesis Example 3: Synthesis of Compound 13

[0345]

[0346] Compound 13 (0.85 g, 27% yield) was obtained in a similar manner to Synthesis Example 1, except that 4,5-bis(methyl-d3)-2-(phenanthro[2,3-b]benzofuran-9-yl)pyridine was used instead of 4,5-bis(methyl-d3)-2-(naphtho[2,3-b]benzofuran-4-yl)pyridine. The compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0347] HRMS (MALDI): For C 77 H 62 Calculated for D6IrN5O: m / z 1277.5430; Found: 1277.5427.

[0348] Synthesis Example 4: Synthesis of Compound 28

[0349]

[0350] Synthesis of Compound 28

[0351] Compound 28 (0.89 g, 27% yield) was obtained in a similar manner to Synthesis Example 1, except that Compound 28B was used instead of Compound 1B, and 4-(2,2-dimethylpropyl-1,1-d2)-5-(methyl-d3)-2-(phenanthro[3,2-b]benzofuran-11-yl)pyridine was used instead of 4,5-bis(methyl-d3)-2-(naphtho[2,3-b]benzofuran-4-yl)pyridine. The compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0352] HRMS (MALDI): For C 83 H75 Calculated value of D5IrN5O: m / z 1360.6306; measured value: 1360.6309.

[0353] Example 1

[0354] The ITO (as the anode)-patterned glass substrate was cut into a size of 50 millimeters (mm) × 50 mm × 0.5 mm, ultrasonically treated with isopropyl alcohol and DI water for 5 minutes each, and then cleaned by UV irradiation and exposure to ozone for 30 minutes. The obtained glass substrate was loaded onto a vacuum deposition apparatus.

[0355] The compounds HT3 and F12-P-dopant were co-deposited in vacuum on the anode at a weight ratio of 98:2 to form a hole injection layer with a thickness, and the compound HT3 was deposited in vacuum on the hole injection layer to form a hole transport layer with a thickness.

[0356] Subsequently, the compounds GH3 (host) and compound 1 (dopant) were co-deposited in vacuum on the hole transport layer at a weight ratio of 92:8 to form an emission layer with a thickness.

[0357] Then, the compounds ET3 and Liq-N-dopant were co-deposited in vacuum on the emission layer at a volume ratio of 50:50 to form an electron transport layer with a thickness, the Liq-N-dopant was deposited in vacuum on the electron transport layer to form an electron injection layer with a thickness, and Al was deposited in vacuum on the electron injection layer to form a cathode with a thickness, thus completing the fabrication of the organic light-emitting device.

[0358]

[0359] Examples 2 to 4 and Comparative Examples 1 to 3

[0360] Organic light-emitting devices were fabricated in a manner similar to that in Example 1, except that: when forming the emission layer, the compounds shown in Table 2 were used instead of compound 1, respectively.

[0361] Evaluation of Example 1: Characterization of the organic light-emitting device

[0362] For the organic light-emitting devices of Examples 1 to 4 and Comparative Examples 1 to 3, the driving voltage (volt, V), maximum external quantum efficiency (Max EQE, %), maximum emission wavelength (λ max , nm), and lifetime (LT 97, relative %) and the results are shown in Table 2. As an evaluation device, a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used. Lifetime (LT 97 )(at 6,000 nits) was evaluated as the time required to reach 97% of the luminance compared to the initial luminance (100%), and the lifetime value was expressed as a relative value with respect to Comparative Example 1.

[0363] Table 2

[0364]

[0365]

[0366]

[0367] Referring to Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 4 had the characteristics of low driving voltage, high maximum EQE, and long lifetime.

[0368] Referring to Table 2, 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 had similar driving voltages, similar or higher maximum EQEs, and significantly improved lifetimes.

[0369] According to one or more of the described embodiments, the organometallic compound represented by Formula 1 has excellent electrical characteristics, and thus an electronic device including at least one of the organometallic compounds represented by Formula 1, such as an organic light-emitting device, can have the characteristics of low driving voltage, high maximum external quantum efficiency, and long lifetime. Therefore, due to the use of at least one of the organometallic compounds represented by Formula 1, a high-quality organic light-emitting device can be realized.

[0370] It should be understood that the exemplary embodiments described herein should be considered only in a descriptive sense and not for purposes of limitation. The description of features or aspects in each exemplary embodiment should typically be considered applicable to other similar features or aspects in other embodiments. Although one or more exemplary embodiments have been described with reference to the accompanying drawings, those of ordinary skill in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope as defined by the appended claims.

Claims

1. An organic metal compound represented by Formula 1: Formula 1 <h2 style=";text-align:left;direction:ltr">M1(L1)<h2 style=";text-align:left;direction:ltr"> n1 <h2 style=";text-align:left;direction:ltr"> (L2)<h2 style=";text-align:left;direction:ltr"> n2 in, In formula 1, M1 is a transition metal, L1 is a ligand represented by Formula 1A, L2 is a ligand represented by Formula 1B, and n1 and n2 are each independently 1 or 2, Formula 1A Formula 1B Wherein, in Formula 1A and 1B, Ring CY1 is a 5-membered heterocyclic group, and C5-C 30 A 5-membered heterocyclic group fused to a carbocyclic group, or a C1-C 30 a 5-membered heterocyclic group fused to a heterocyclic group, Ring CY2 and ring CY4 are each independently C5-C 30 Carbocyclic group or C1-C 30 a heterocyclic group, X1 is C or N, X2 is C or N, X3 is C or N, and X4 is C or N, X 31 C(R 31 ) or N, and X 34 C(R 34 ) or N, X 41 C(R 41 ) or N, X 42 C(R 42 ) or N, X 43 C(R 43 ) or N, and X 44 C(R 44 ) or N, Y1 is O, S or Se, R1, R2, R4, R 31 , R 34 , and R 41 To R 44 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 heteroarylthio, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(═O)(Q8)(Q9), R 32 and R 33 are each independently deuterium, including deuterium-substituted C1-C 60 Alkyl, including deuterated substituted C3-C 10 Cycloalkyl, including deuterated substituted C6-C 60 Aryl, or a deuterated C1-C 60 Heteroaryl, Two or more adjacent R1 groups are optionally bonded to each other to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups, Two or more adjacent R2 groups are optionally bonded together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups, Two or more adjacent R4 groups are optionally bonded together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups, R1, R2, R4, R 31 , R 34 , and R 41 To R 44 Two or more adjacent groups are optionally bonded together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups, b1, b2 and b4 are each independently an integer from 0 to 10, * and *' each represent the binding site with M1, Substituted C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 The substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are each independently: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio; C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-Ge(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(Q 18 )(Q 19 )、-P(=O)(Q 18 )(Q 19 ), or a combination thereof; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(Q 28 )(Q 29 )、-P(=O)(Q 28 )(Q 29 ), or a combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(Q 38 )(Q 39 )、 or -P(=O)(Q 38 )(Q 39 ), and Q1 to Q9, Q 11 To Q 19 , Q 21 To Q 29 , and Q 31 To Q 39 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

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

3. The organometallic compound according to claim 1, wherein the ring CY1 is a pyrrole group, an imidazole group, a pyrazole group, an oxazole group, an indole group, an azaindole group, a benzopyrazole group, a benzimidazole group, or a benzoxazole group.

4. The organometallic compound according to claim 1, wherein ring CY2 and ring CY4 are each independently a benzene group, a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

5. The organometallic compound according to claim 1, wherein Ring CY1 is an imidazole group or a benzimidazole group, and Ring CY2 is a benzene group, a naphthyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group.

6. The organometallic compound according to claim 1, wherein in Formula 1A The moiety represented by is a group represented by one of the formulae CY(1)-1 to CY(1)-3: in, In formulae CY(1)-1 to CY(1)-3, X 11 C(R 11a )、C(R 11a )(R 11b ), N, or N(R 11a ), X 12 C(R 12a )、C(R 12a )(R 12b ), N, or N(R 12a ), X 13 C(R 13a )、C(R 13a )(R 13b ), N, or N(R 13a ), Cyclo 10 C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, R 10 , R 11a , R 11b , R 12a , R 12b , R 13a and R 13b each independently as defined for R1, b10 is an integer from 1 to 10, represents a single bond or a double bond, * indicates the binding site with M1, and *” indicates the binding site with the adjacent atoms.

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

8. The organometallic compound according to claim 1, wherein L1 is a ligand represented by Formula 1A-1 or 1A-2: in, In Formulas 1A-1 and 1A-2, R 10 To R 13 each independently as defined for R1, R 20 As defined for R2, b10 and b20 are each independently an integer from 1 to 4, and * and *' each indicate a binding site to M1.

9. The organometallic compound according to claim 1, wherein L2 is a ligand represented by one of Formulas 1B-1 to 1B-4: in, In Formulas 1B-1 to 1B-4, X3, X4, X 31 , X 34 , X 41 To X 44 ,Y1,R 32 , and R 33 Each as defined in claim 1, E1 is C(Z1) or N, E2 is C(Z2) or N, E3 is C(Z3) or N, and E4 is C(Z4) or N, E5 is C(Z5) or N, E6 is C(Z6) or N, E7 is C(Z7) or N, and E8 is C(Z8) or N, Z1 to Z8 are each independently as defined for R4, and * and *' each indicate a binding site to M1.

10. The organometallic compound according to claim 1, wherein L2 is a ligand represented by one of formulas 1B(1)-1 to 1B(1)-4: in, In Formulae 1B(1)-1 to 1B(1)-4, X3, X4, X 41 To X 44 ,Y1,R 31 , R 32 , R 33 , and R 34 Each as defined in claim 1, R 40 As defined for R4, b40 is an integer from 1 to 4, b41 is an integer from 1 to 6, and * and *' each indicate a binding site to M1.

11. The organometallic compound according to claim 1, wherein R 32 and R 33 Each is independently -CD3, -CD2H, -CDH2, or a group represented by one of formulae 8-1 to 8-15: in, In Formulae 8-1 to 8-15, * represents a bonding site with an adjacent atom.

12. The organometallic compound according to claim 1, wherein R1, R2, R4, R 31 , R 34 , and R 41 To R 44 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, or C1-C 20 Alkylthio; C1-C 20 Alkyl, C1-C 20 Alkoxy, or C1-C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, or a combination thereof; Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl; cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl , oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, or imidazopyrimidyl: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or a combination thereof; or -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=O)(Q8)(Q9), and Q1 to Q9 are each independently: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of: deuterium, C1-C 10 Alkyl, phenyl, or a combination thereof.

13. The organometallic compound according to claim 1, wherein R1, R2, R4, R 31 , R 34 , and R 41 To R 44 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio; A group represented by one of formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, or 10-201 to 10-350; or -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), or -N(Q4)(Q5), Q1 to Q5 are as defined in claim 1: in, In Formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, and 10-201 to 10-350, * represents a bonding site to an adjacent atom, "Ph" represents a phenyl group, "TMS" represents a trimethylsilyl group, and "TMG" represents a trimethylgermyl group.

14. The organometallic compound according to claim 1, wherein the organometallic compound is represented by one of Formulas 1-1 to 1-4: in, In formulas 1-1 to 1-4, M1, n1, n2, Y1, R 31 To R 34 , and R 41 To R 44 Each as defined in claim 1, R 10 and R 11 each independently as defined for R1, R 20 As defined for R2, R 51 and R 52 each independently as defined for R4, b10, b20, b50 and b52 are each independently an integer from 1 to 4, and b51 is 1 or 2.

15. The organometallic compound according to claim 1, wherein the organometallic compound is represented by one of Compounds 1 to 72:

16. Organic light-emitting device, comprising: a first electrode; a second electrode; as well as an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and The organic layer comprises at least one of the organometallic compounds according to any one of claims 1 to 15.

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

19. The organic light emitting device according to claim 16, wherein: The first electrode is an anode, The second electrode is a cathode, and The organic layer further includes a hole transport region disposed between the first electrode and the emission layer; and an electron transport region disposed between the emission layer and the second electrode, in The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

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

Images