Organometallic compound, organic light emitting device including the same, and electronic device including the 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, in which M is a transition metal; L1 is a ligand represented by Formula 2 as disclosed herein; L2 is a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand; n1 is 1, 2, or 3, wherein, when n1 is 2 or more, two or more ligands L1 are the same as or different from each other; n2 is 0, 1, 2, 3, or 4, wherein, when n2 is 2 or more, two or more ligands L2 are the same as or different from each other; and L1 and L2 are different from each other. Formula 1 M(L1) n1 (L2) n2 .

Description

[0001] Cross Reference to Related Applications

[0002] This application claims the benefit of and priority to Korean Patent Application No. 10-2020-0015840, filed on February 10, 2020, in the Korean Intellectual Property Office, and all the benefits accruing therefrom, the disclosure of which is incorporated by reference herein in its entirety. TECHNICAL FIELD

[0003] One or more embodiments relate to an organometallic compound, an organic light emitting device including the same, and an electronic device including the organic light emitting device. BACKGROUND

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

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

[0006] One or more embodiments relate to 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 description that follows, and in part will become apparent to those skilled in the art upon examination of the following description and the accompanying drawings or can be learned by practice of the presented embodiments of the disclosure.

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

[0009] Formula 1

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

[0011] In Formula 1,

[0012] M is a transition metal,

[0013] L1 is a ligand represented by Formula 2,

[0014] n1 is 1, 2, or 3, wherein, when n1 is 2 or greater, two or more of the ligands L1 can be the same or different from each other,

[0015] L2 is a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand,

[0016] n2 is 0, 1, 2, 3, or 4, wherein, when n2 is 2 or greater, two or more of the ligands L2 are the same or different from each other, and

[0017] L1 and L2 are different from each other,

[0018]

[0019] wherein, in formula 2,

[0020] X 11 is N, C(R 11 ), or C bonded to X1 in formula 3,

[0021] X 12 is N, C(R 12 ), or C bonded to X1 or X2 in formula 3,

[0022] X 13 is N, C(R 13 ), or C bonded to X1 or X2 in formula 3, and

[0023] X 14 is N, C(R 14 ), or C bonded to X2 in formula 3,

[0024] provided that X 11 is C bonded to X1 in formula 3, and X 12 is C bonded to X2 in formula 3; X 12 is C bonded to X1 in formula 3, and X 13 is C bonded to X2 in formula 3; or X 13 is C bonded to X1 in formula 3, and X 14 is C bonded to X2 in formula 3,

[0025] In formula 3, X1 is O, S, Se, B(R 31 ), N(R 31 ), C(R 31 )(R 32 ), or Si(R 31 )(R 32 ),

[0026] In formula 3, X2 is O, S, Se, B(R 33 ), N(R 33 ), C(R33 (R) 34 ), or Si(R) 33 (R) 34 Y1 is N, and Y2 is C or N.

[0027] Cycle CY1 and Cycle CY2 are each independently C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups,

[0028] R1, R2, R 11 -R 14 and R 31 -R 34 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroalkyl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), wherein R 31 and R 33 Not hydrogen,

[0029] a1 is an integer from 0 to 20, where when a1 is 2 or greater, two or more groups R1 are the same or different from each other.

[0030] a2 is an integer from 0 to 20, where when a2 is 2 or greater, two or more groups R2 are either the same or different from each other.

[0031] The condition is that the organometallic compound does not include n2 in formula 1 being 0, and X1 in formula 3 being C(R) 31 (R) 32 ), and X2 in Equation 3 is C(R) 33 (R) 34 ) compounds,

[0032] Two or more of the plurality of groups R1 are optionally linked together to form an unsubstituted or at least one R group. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0033] Two or more of the multiple groups R2 are optionally linked together to form an unsubstituted or at least one R group. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0034] R 10a As disclosed regarding R2,

[0035] In Equation 2, * and *' each represent the binding site with M in Equation 1.

[0036] In Equation 3, * and *' represent X in Equation 2. 11 -X 14 The two binding sites in

[0037] Replacement C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60alkyl, C1-C 60 aryloxy, substituted C6-C 60 arylthio, substituted C7-C 60 aralkyl, substituted C1-C 60 heteroaryl, substituted C1-C 60 heteroaryloxy, substituted C1-C 60 heteroarylthio, substituted C2-C 60 heteroaralkyl, substituted C2-C 60 alkylheteroaryl, substituted monovalent non-aromatic fused polycyclic radical, and substituted monovalent non-aromatic fused heteropolycyclic radical are each independently:

[0038] deuterium, -F, -CI, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 60 alkyl, C1-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy;

[0039] C1-C 60 alkyl, C1-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy: deuterium, -F, -CI, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C1-C 60 heteroaryl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, C2-C 60 heteroaralkyl, C2-C 60 alkylheteroaryl, monovalent non-aromatic fused polycyclic radical, monovalent non-aromatic fused heteropolycyclic radical, -N(Q 11 )(Q12 ), -Si(Q 13 (Q) 14 (Q) 15 -Ge(Q) 13 (Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 ), or -P(Q 18 (Q) 19 );

[0040] Each of the following C3-Cs is either not substituted or is substituted by at least one of the following: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroalkyl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -N(Q 21 (Q) 22), -Si(Q 23 (Q) 24 (Q) 25 -Ge(Q) 23 (Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 ), or -P(Q 28 (Q) 29 );

[0041] -N(Q 31 (Q) 32 ), -Si(Q 33 (Q) 34 (Q) 35 -Ge(Q) 33 (Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q) 38 (Q) 39 ), or -P(Q 38 (Q) 39 );or

[0042] Its combination, and

[0043] Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each of the following is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidine; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphate group or its salt; unsubstituted or deuterated, C1-C 60 Alkyl, or C6-C 60 At least one substituted C1-C of aryl 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkyl group; C3-C 10 cycloalkyl; C1-C 10 Heterocyclic alkyl; C3-C 10 Cycloalkenyl; C1-C 10 Heterocyclic alkenyl groups; unsubstituted or deuterated, C1-C 60 Alkyl, or C6-C 60 At least one substituted C6-C of aryl group60 aryl; C6-C 60 aryloxy; C6-C 60 arylthio; C7-C 60 aralkyl; C7-C 60 heteroaryl; C1-C 60 heteroaryloxy; C1-C 60 heteroarylthio; C2-C 60 heteroaralkyl; C2-C 60 alkylheteroaryl; a monovalent non-aromatic fused polycyclic group; or a monovalent non-aromatic fused heteropolycyclic group.

[0044] According to another aspect, there is provided an organic light emitting device including: a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one organic metal compound represented by Formula 1.

[0045] The organic metal compound can be included in the emission layer, and the organic metal compound included in the emission layer can act as a dopant.

[0046] According to another aspect, there is provided an electronic device including the organic light emitting device. BRIEF DESCRIPTION OF DRAWINGS

[0047] By incorporation Figure 1 The above and other aspects, features, and advantages of some embodiments of the present disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, wherein, Figure 1 A schematic cross-sectional view of an organic light emitting device according to one or more embodiments is shown. DETAILED DESCRIPTION

[0048] Embodiments will now be described in detail with reference to examples illustrated in the drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments can have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below by referring to the figures to explain aspects.

[0049] The terminology used herein is for the purpose of describing example embodiments only and is not intended to be limiting. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. The term "or" means "and / or". As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. Expressions such as "at least one of," when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

[0050] It will be further understood that the terms "comprises" and / or "comprising", when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and / or groups thereof.

[0051] It will be understood that when an element is referred to as being "on" another element, it can be directly on the other element or intervening elements can be present therebetween. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.

[0052] It will be understood that, although the terms first, second, third, etc. can be used herein to describe various elements, components, regions, layers and / or sections, these elements, components, regions, layers and / or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Thus, a first element, component, region, layer or section discussed below could be termed a second element, component, region, layer or section without departing from the teachings of the present embodiments.

[0053] 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 relevant art and the present disclosure and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

[0054] "About" or "approximately" as used herein includes the recited value and means within an acceptable range of deviation for the stated value as would be determined by one of ordinary skill in the art to be within the scope of the measurements and errors inherent in the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ± 10% or 5% of the stated value.

[0055] One aspect of the present disclosure provides an organometallic compound represented by Formula 1:

[0056] Formula 1

[0057] M(L1) n1 (L2) n2

[0058] M in Formula 1 is a transition metal.

[0059] For example, M 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.

[0060] In an embodiment, M can be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0061] In an embodiment, M can be Ir, Pt, Os, or Rh.

[0062] L1in Formula 1 is a ligand represented by Formula 2.

[0063] Formula 2

[0064]

[0065] The detailed description of Formula 2 is the same as described herein below for Formula 2.

[0066] n1in Formula 1 represents the number of ligands L1and can be 1, 2, or 3. When n1is 2 or greater, two or more ligands L1may be the same as or different from each other. For example, n1may be 1 or 2.

[0067] L2in Formula 1 can be a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand. L2is further described herein below.

[0068] n2in Formula 1 represents the number of ligands L2and can be 0, 1, 2, 3, or 4. When n2is 2 or greater, two or more ligands L2may be the same as or different from each other. For example, n2may be 1 or 2.

[0069] L1and L2in Formula 1 can be different from each other.

[0070] In an embodiment, in Formula 1, M can be Ir or Os, and the sum of n1and n2may be 3 or 4; or M can be Pt, and the sum of n1and n2may be 2.

[0071] In one or more embodiments, in Formula 1,

[0072] M can be Ir,

[0073] n1and n2may each independently be 1 or 2, and

[0074] the sum of n1and n2may be 3.

[0075] In Formula 2, X 11 may be N, C(R 11 ), or C bonded to X1in Formula 3 (via a single bond), X 12N, C(R 12 ), or C bonded to X1or X2in Formula 3 (via a single bond), X 13 may be N, C(R 13 ), or C bonded to X1or X2in Formula 3 (via a single bond), and X 14 may be N, C(R 14 ), or C bonded to X2in Formula 3 (via a single bond). Here, in Formula 2, i) X 11 may be C bonded to X1in Formula 3 (via a single bond), and X 12 may be C bonded to X2in Formula 3 (via a single bond), ii) X 12 may be C bonded to X1in Formula 3 (via a single bond), and X 13 may be C bonded to X2in Formula 3 (via a single bond), or iii) X 13 may be C bonded to X1in Formula 3 (via a single bond), and X 14 may be C bonded to X2in Formula 3 (via a single bond).

[0076] Formula 3

[0077]

[0078] In other words, the group represented by Formula 3 must (necessarily) be fused to the group represented by Formula 2. Thus, L1is in fact a ligand obtained by fusing the group represented by Formula 3 to the group represented by Formula 2.

[0079] In Formula 3, X1may be O, S, Se, B(R 31 ), N(R 31 ), C(R 31 )(R 32 ), or Si(R 31 )(R 32 ), and X2may be O, S, Se, B(R 33 ), N(R 33 ), C(R 33 )(R 34 ), or Si(R 33 )(R 34 ).

[0080] In one embodiment, at least one of X1and X2in Formula 3 can be O, S, or Se.

[0081] In one or more embodiments, X1and X2in Formula 3 can be the same as each other.

[0082] In one or more embodiments, X1and X2in Formula 3 can be different from each other.

[0083] In one or more embodiments, in Equation 3, X1 can be C(R) 31 (R) 32 X2 can be O, S, Se, B(R) 33 ), N(R 33 ), or Si(R) 33 (R) 34 ); or X1 can be O, S, Se, B(R) 31 ), N(R 31 ), or Si(R) 31 (R) 32 ), and X2 can be C(R) 33 (R) 34 ).

[0084] In Equation 2, Y1 can be N, and Y2 can be C or N. For example, Y2 in Equation 2 can be C.

[0085] In equations 2 and 3, rings CY1 and CY2 can each be independently C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups.

[0086] For example, rings CY1 and CY2 in equations 2 and 3 can each independently be a first ring, a second ring, a fused ring in which two or more first rings are fused together, a fused ring in which two or more second rings are fused together, or a fused ring in which one or more first rings are fused with one or more second rings.

[0087] The first ring may be a cyclopentyl group, a cyclopentadienyl group, a furan group, a thiophene group, a pyrrole group, a thiophene group, an indole group, a benzofuran group, a benzothiophene group, an indole group, or a benzothiophene group. azole group, iso- azole group, diazole group, isodiazole group diazole group, Triazole group, iso Triazole group, thiazole group, isothiazole group, thiadiazole group, isothiazole group, thiatriazole group, isothiazole group, pyrazole group, imidazole group, triazole group, tetraazole group, azathiophene group, diazathiophene group, or triazathiophene group, and

[0088] The second ring may be an adamantyl group, a norbornel group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a cyclohexyl group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0089] For example, in formulas 2 and 3, cyclo(CY1) and cyclo(CY2) can each independently be a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentene group, a cyclohexene group, a cycloheptene group, an adamantyl group, a norbornene group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, Groups, 1,2,3,4-tetrahydronaphthalene group, pyrrole group, borole group, phosphole group, cyclopentadiene group, thiorrole group, germanocyclopentadiene group, thiophene group, selenophene group, furan group, indole group, benzoborocyclopentadiene group, benzophosphole group, indene group, benzothiorrole group, benzogermanocyclopentadiene group, benzothiophene group, benzoselenophene group Groups, including benzofuran group, carbazole group, dibenzoborane heterocyclopentadienyl group, dibenzophosphacyclopentadienyl group, fluorene group, dibenzothiophene group, dibenzogermanium heterocyclopentadienyl group, dibenzothiophene group, dibenzoselenene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azidindole group, azibenzoborane heterocyclopentadienyl group, azibenzophosphacyclopentadienyl group, and azidindole group. Azabenzothiophene group, azabenzogermanium heterocyclopentadienyl group, azabenzothiophene group, azabenzoselenene group, azabenzofuran group, azacarbazole group, azadibenzoborone heterocyclopentadienyl group, azadibenzophosphonone heterocyclopentadienyl group, azafluorene group, azadibenzothiophene group, azadibenzogermanium heterocyclopentadienyl group, azadibenzothiophene group, azadibenzoselenene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H- Fluorene-9-one group, azirdibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzo[a]quinoline group, benzo[a]isoquinoline group, quinoxaline group, quinazoline group, phenanthrene group, pyrazole group, imidazole group, triazole group, aziborone-cyclopentadiene group, aziphosphonone-cyclopentadiene group, azithiophene group, azigerne-cyclopentadiene group, aziselenophene group azole group, iso- azole group, thiazole group, isothiazole group, Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo[] azole group, benzothiazole group, benzo[] The diazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, or 5,6,7,8-tetrahydroquinoline group.

[0090] In an embodiment, ring CY1in Formula 3 can be a phenyl group, a pyridyl group, or a pyrimidyl group.

[0091] In one or more embodiments, Y2in Formula 2 can be C, and ring CY2in Formula 2 can be a phenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, or a dibenzosilolyl group.

[0092] In Formulas 2 and 3, R1, R2, R 11 -R 14 , and R 31 -R 34 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone 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 substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C7-C 60 aralkyl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C7-C 60 aralkyl group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted C1-C 60 heteroaryloxy group, a substituted or unsubstituted C1-C 60 heteroarylthio group, a substituted or unsubstituted C2-C 60 heteroaralkyl group, a substituted or unsubstituted C2-C 60 alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), where R 31 and R 33may not be hydrogen. Q1-Q9 are the same as described in the specification.

[0093] For example, R1, R2, R 11 -R 14 , and R 31 -R 34 may each independently be:

[0094] hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, -SF5, C1-C 20 alkyl, or C1-C 20 alkoxy;

[0095] C1-C 20 alkyl or C1-C 20 alkoxy each independently substituted with at least one of: hydrogen, deuterium, -F, -CI, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, 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 20 alkyl, deuterated C1-C 20 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 alkyl)adamantyl, (C1-C 20 alkyl)norbornyl, (C1-C 20 alkyl)norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, or pyrimidyl;

[0096] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20 alkyl)norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, or azadibenzothiophenyl; or

[0097] -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0098] Q1-Q9 can be independently defined as follows:

[0099] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or

[0100] Each of the following is unsubstituted or substituted with at least one of the following: n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl: deuterium, C1-C 20 Alkyl or phenyl.

[0101] In one implementation, R1, R2, R 11 -R 14 and R 31 -R34 each independently hydrogen, deuterium, -F, cyano, nitro, -SF5, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by one of formulae 9-1 to 9-66, a group represented by one of formulae 9-1 to 9-66 in which at least one hydrogen is replaced with deuterium, a group represented by one of formulae 10-1 to 10-118, a group represented by one of formulae 10-1 to 10-118 in which at least one hydrogen is replaced with deuterium, a group represented by one of formulae 10-201 to 10-342, a group represented by one of formulae 10-201 to 10-342 in which at least one hydrogen is replaced with deuterium, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5) (wherein Q3to Q5are the same as described in this specification):

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] In formulae 9-1 to 9-66, 10-1 to 10-118, and 10-201 to 10-342, * indicates a bonding site to an adjacent atom, Ph is a phenyl group, and TMS is a trimethylsilyl group.

[0110] The “group represented by one of formulae 9-1 to 9-66 in which at least one hydrogen is replaced with deuterium” can be, for example, a group represented by one of formulae 9-501 to 9-514 and 9-601 to 9-638:

[0111]

[0112] The “group represented by one of formulae 10-1 to 10-118 in which at least one hydrogen is replaced with deuterium” can be, for example, a group represented by one of formulae 10-501 to 10-546.

[0113]

[0114] a1in formula 3 represents the number of groups R1and can be an integer from 0 to 10. When a1is 2 or greater, two or more groups R1may be the same as or different from each other. For example, a1may be 0, 1, or 2.

[0115] a2in formula 2 represents the number of groups R2and can be an integer from 0 to 20. When a2is 2 or greater, two or more groups R2may be the same as or different from each other. For example, a2may be an integer from 0 to 10.

[0116] In an embodiment, L1in formula 1 can be a ligand represented by formula 2-1, 2-2, or 2-3.

[0117]

[0118] In formula 2-1 to 2-3,

[0119] X 11 may be N or C(R 11 ), X 12 may be N or C(R 12 ), X 13 may be N or C(R 13 ), X 14 may be N or C(R 14 ), and

[0120] X1, X2, Y1, Y2, ring CY1, ring CY2, R1, R2, R 11 -R 14 , a1, a2, *, and *' are the same as described in this specification.

[0121] In an embodiment, L1in formula 1 can be a ligand represented by formula 2-3,

[0122] X 12 in formula 2-3 12 may be C(R 12 ), and

[0123] R 12 may be -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), where Q3-Q5are as provided herein.

[0124] In an embodiment, L1in formula 1 can be a ligand represented by formula 2-1(1), 2-2(1), or 2-3(1):

[0125]

[0126] In formula 2-1(1), 2-2(1), and 2-3(1), X1, X2, Y1, Y2, ring CY2, R1, R2, R 11 -R14 a1, a2, * and * are the same as described in the specification.

[0127] In one or more embodiments, the group represented by in Formula 2 can be a group represented by one of Formulas CY2-1 to CY2-31:

[0128]

[0129]

[0130] In Formulas CY2-1 to CY2-31,

[0131] Y2and R2are each the same as described above,

[0132] X 22 is C(R 22 )(R 23 ), N(R 22 ), O, S, or Si(R 22 )(R 23 ),

[0133] R 22 -R 29 is the same as described for R2,

[0134] a26is an integer from 0 to 6,

[0135] a25is an integer from 0 to 5,

[0136] a24is an integer from 0 to 4,

[0137] a23is an integer from 0 to 3,

[0138] a22is an integer from 0 to 2,

[0139] * represents a bonding site to an adjacent atom in Formula 2, and

[0140] * represents a bonding site to M in Formula 1.

[0141] Meanwhile, L2in Formula 1 can be a bidentate ligand to M in Formula 1 via two atoms selected from the group consisting of O, S, N, C, P, Si, and As. The two atoms can be the same or different. For example, both of the two atoms can be O, or one of them is O and the other one of them is S or C.

[0142] In one embodiment, L2in Formula 1 can be a bidentate ligand to M in Formula 1 via two atoms selected from the group consisting of N and C.

[0143] In one embodiment, L2in Formula 1 can be a group represented by one of Formulas 3A to 3F:

[0144] In Formulas 3A to 3F,

[0145] Y 13 is O, N, N(Z1), P(Z1)(Z2), or As(Z1)(Z2),

[0146] Y 14 is O, N, N(Z3), P(Z3)(Z4), or As(Z3)(Z4),

[0147] T 11 is a single bond, a double bond, *-C(Z 11 )(Z 12 )-*, 11 *-C(Z 12 )=C(Z 11 )-*, 11 *-C(Z 11 )=*, 12 * =C(Z 13 )-C(Z 11 )=C(Z 12 )-*, 13 *-N(Z 11 )-*, or a C5-C 11 carbocyclic group, which is unsubstituted or substituted with at least one Z 30 ,

[0148] a11is an integer from 0 to 10, wherein, when a11is 2 or greater, two or more groups T 11 are identical to or different from each other,

[0149] Y 11 and Y 12 are each independently C or N,

[0150] T 21 is a single bond, a double bond, O, S, C(Z 11 )(Z 12 ), Si(Z 11 )(Z 12 ), or N(Z 11 ),

[0151] ring CY 11 and ring CY 12 are each independently a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group,

[0152] A1is P or As,

[0153] Z1-Z4and Z 11 -Z 13 the same as described for R2,

[0154] d1-d2are each independently an integer from 0 to 10, and

[0155] *and *' each represent a binding site to M in Formula 1.

[0156] For example, the group represented by in Formula 3D can be a group represented by one of Formulas CY11-1 to CY11-34, and (or)

[0157] the group represented by in Formulas 3C and 3D can be a group represented by one of Formulas CY12-1 to CY12-34:

[0158]

[0159]

[0160]

[0161] In Formulas CY11-1 to CY11-34 and CY12-1 to CY12-34,

[0162] X 31 is O, S, N(Z 11 ), C(Z 11 )(Z 12 ), or Si(Z 11 )(Z 12 ),

[0163] X 41 is O, S, N(Z 21 ), C(Z 21 )(Z 22 ), or Si(Z 21 )(Z 22 ),

[0164] Y 11 , Y 12 , Z1, and Z2 are the same as described in this specification,

[0165] Z 11 -Z 18 and Z 21 -Z 28 the same as described for R1,

[0166] each of d12and d22is independently an integer from 0 to 2,

[0167] each of d13and d23is independently an integer from 0 to 3,

[0168] each of d14and d24is independently an integer from 0 to 4,

[0169] each of d15and d25is independently an integer from 0 to 5,

[0170] each of d16and d26is independently an integer from 0 to 6, and

[0171] In formulas CY11-1 to CY11-34 and CY12-1 to CY12-34, each of * and *' represents a binding site to M in Formula 1, and *" represents a binding site to an adjacent atom in Formula 3C or a binding site to T 21 in Formula 3D.

[0172] In an embodiment, L2in Formula 1 can be a ligand represented by Formula 3D, and at least one of Z1and Z2in Formula 3D can each independently be: deuterium; -Si(Q3)(Q4)(Q5); -Ge(Q3)(Q4)(Q5); or C1-C 60 alkyl substituted with at least one deuterium.

[0173] In an embodiment, L2may be a ligand represented by one of Formulas 3-1 and 3-101 to 3-112:

[0174] In Formulas 3-1 and 3-101 to 3-112,

[0175] Y 11 , Y 12 , ring CY 12 , Z1-Z4, Z 11 -Z 13 , and d2are the same as described in this specification,

[0176] Z 14 are the same as described with respect to Z 11 ,

[0177] e2is an integer from 0 to 2,

[0178] e3is an integer from 0 to 3,

[0179] e4is an integer from 0 to 4, and

[0180] each of * and *' represents a binding site to M in Formula 1.

[0181] In an embodiment, Z12 It can be: -Si(Q3)(Q4)(Q5); -Ge(Q3)(Q4)(Q5); or deuterated C1-C 60 alkyl.

[0182] In one implementation, in formula 3-1, Z 12 It can be -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), and Z 13 It may not be hydrogen or methyl.

[0183] In one or more embodiments, the formula 3-1 is derived from... The represented group may be a group represented by one of formulas 3-1-1 to 3-1-16, and / or

[0184] In Equation 3-1, the The group represented may be one of the groups represented by formulas 3-1(1) to 3-1(16):

[0185]

[0186] In equations 3-1-1 to 3-1-16 and 3-1(1) to 3-1(16),

[0187] Z 11 -Z 14 As described in this specification, Z 21 -Z 24 Regarding Z 11 The description is the same, where Z 11 -Z 14 and Z 21 -Z 24 Not hydrogen,

[0188] * and *' represent the binding sites with M in Equation 1, and

[0189] * indicates a binding site with an adjacent atom.

[0190] The organometallic compounds of Formula 1 do not include (i.e., exclude) compounds in which n2 in Formula 1 is 0 and X1 in Formula 3 is C(R) 31 (R) 32 ), and X2 in Equation 3 is C(R 33 (R) 34 ) compounds.

[0191] In Formula 1, two or more of the plurality of groups R1 may optionally be linked together to form an unsubstituted or at least one R group. 10a Replacement C5-C 30a carbocyclic group unsubstituted or substituted with at least one R 10a substituted C1-C 30 heterocyclic group; and two or more of the groups R2may optionally be linked together to form a carbocyclic or heterocyclic group unsubstituted or substituted with at least one R 10a substituted C5-C 30 a carbocyclic group unsubstituted or substituted with at least one R 10a substituted C1-C 30 heterocyclic group.

[0192] R 10a the same as described for R2.

[0193] * and *' in Formula 2 each represent a binding site to M in Formula 1.

[0194] * and *' in Formula 3 represent binding sites to X 11 -X 14 in Formula 2.

[0195] For example, the organometallic compound represented by Formula 1 can be one of Compounds 1 to 289:

[0196]

[0197] Compounds 10 to 289 are represented by Formula 1, wherein M is Ir, L2is a phenyl-pyridine ligand, and L1, n1, and n2are each as defined in Tables 1 to 8 below. In Tables 1 to 8, Ph is phenyl, Me is methyl, TMS is trimethylsilyl, and CY2-1(1) and CY2-1(2) have the following formulae:

[0198]

[0199] In Formulae CY2-1(1) and CY2-1(2), * represents a binding site to M in Formula 1, and *' represents a binding site to an adjacent atom.

[0200] Table 1

[0201]

[0202]

[0203] Table 2

[0204]

[0205]

[0206] Table 3

[0207]

[0208]

[0209] Table 4

[0210]

[0211]

[0212] Table 5

[0213]

[0214]

[0215] Table 6

[0216]

[0217]

[0218] Table 7

[0219]

[0220]

[0221] Table 8

[0222]

[0223]

[0224] In the organometallic compound represented by Formula 1, L1is a ligand represented by Formula 2, and n1 representing the number of ligands L1is 1, 2, or 3. That is, the organometallic compound must include at least one ligand represented by Formula 2 as a ligand connected to the metal M. An electronic device including the organometallic compound represented by Formula 1, for example, an organic light emitting device, can have improved driving voltage and improved external quantum efficiency.

[0225] For some of the organometallic compounds represented by Formula 1, the highest occupied molecular orbital (HOMO) energy level and the lowest unoccupied molecular orbital (LUMO) energy level, and the T1 energy level were evaluated using the Gaussian 09 program for molecular structure optimization based on B3LYP by density functional theory (DFT), and the results thereof are shown in Table 9.

[0226] Table 9

[0227] Compound No. HOMO (eV) LUMO (eV) [T1 (eV)] 1 -4.840 -1.238 2.573 2 -4.841 -1.304 2.556 3 -4.809 -1.166 2.632 4 -4.832 -1.208 2.616 5 -4.806 -1.200 2.609 6 -4.865 -1.228 2.592 7 -4.812 -1.246 2.561 8 -4.765 -1.236 2.553 9 -4.823 -1.247 2.583

[0228] From Table 9, it is confirmed that the organometallic compound represented by Formula 1 has electrical properties suitable for use as a material for an electronic device, for example, a dopant for an emission layer of an organic light-emitting device.

[0229] A person of ordinary skill in the art can understand the method of synthesizing the organometallic compound represented by Formula 1 by referring to the synthesis examples provided below.

[0230] Accordingly, the organometallic compound represented by Formula 1 is suitable for use as a material for an organic light-emitting device, for example, a dopant for an emission layer in an organic layer of an organic light-emitting device. Accordingly, another aspect provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode and comprising an emission layer, and the organic layer comprising at least one organometallic compound represented by Formula 1.

[0231] Due to the organic layer comprising the organometallic compound represented by Formula 1, the organic light-emitting device can have a low driving voltage, a high luminous efficiency, a high power efficiency, a high external quantum efficiency, a long lifespan, a low roll-off ratio, and excellent color purity.

[0232] The organometallic compound represented by Formula 1 can be disposed between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Formula 1 can be included in the emission layer. In this regard, the organometallic compound can act as a dopant, and the emission layer can further comprise a host (that is, the amount of the organometallic compound represented by Formula 1 is less than the amount of the host). The emission layer can emit red light or green light.

[0233] For example, the organometallic compound represented by Formula 1 can emit green light having a maximum emission wavelength in a range of about 500 nanometers (nm) to about 550 nm, for example, about 500 nm to about 540 nm.

[0234] The expression "(organic layer) comprises at least one organometallic compound" used herein can include a case where "(organic layer) comprises the same organometallic compound represented by Formula 1" and a case where "(organic layer) comprises two or more different organometallic compounds represented by Formula 1."

[0235] For example, the organic layer can comprise only Compound 1 as the organometallic compound. In this regard, Compound 1 can be present only in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer can comprise Compound 1 and Compound 2 as the organometallic compound. In this regard, 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).

[0236] The first electrode can be an anode functioning as a hole injection electrode, and the second electrode can be a cathode functioning as an electron injection electrode, or the first electrode can be a cathode functioning as an electron injection electrode, and the second electrode can be an anode functioning as a hole injection electrode.

[0237] For example, in the organic light emitting device, the first electrode is an anode, the second electrode is a cathode, and the organic layer can 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, the hole transport region can 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 can include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0238] The term "organic layer" used herein refers to a single layer and / or multiple layers between the first electrode and the second electrode of the organic light emitting device. The "organic layer" can include an organometallic complex including a metal in addition to an organic compound.

[0239] Figure 1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment. Hereinafter, the organic light emitting device 10 will be described with respect to Figure 1 The structure of the organic light emitting device according to an embodiment and a method of manufacturing the organic light emitting device according to an embodiment are described. The organic light emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.

[0240] A substrate can be additionally disposed under (i.e., below) the first electrode 11 or over the second electrode 19. For use as the substrate, any substrate used in an organic light emitting device can be used, and the substrate can be a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0241] In one or more embodiments, the first electrode 11 can be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 can be an anode. The material for forming the first electrode 11 can include a material having a high work function to facilitate hole injection. The first electrode 11 can be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 can include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or a combination thereof. In one or more embodiments, the material for forming the first electrode 11 can include a metal or a metal alloy, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or a combination thereof.

[0242] The first electrode 11 can have a single layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 can have a three-layer structure of ITO / Ag / ITO.

[0243] The organic layer 15 can be disposed on the first electrode 11.

[0244] The organic layer 15 can include a hole transport region, an emission layer, and an electron transport region.

[0245] The hole transport region can be disposed between the first electrode 11 and the emission layer.

[0246] The hole transport region can include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.

[0247] The hole transport region can include a hole injection layer, a hole transport layer, or a combination thereof. In one or more embodiments, the hole transport region can have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, where, for each structure, the layers are sequentially stacked in the order stated from the first electrode 11 toward the second electrode 19.

[0248] When the hole transport region includes a hole injection layer, the hole injection layer can be formed on the first electrode 11 by using one or more suitable methods, such as vacuum deposition, spin coating, casting, and / or Langmuir-Blodgett (LB) deposition.

[0249] When the hole injection layer is formed by vacuum deposition, the deposition conditions can vary depending on the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, the deposition conditions can include a deposition temperature of about 100°C to about 500°C, a vacuum pressure of about 10 -8 tor to about 10 -3 tor, and a deposition rate of about 0.01 angstroms / second to about 1 angstroms / second. - about 1 angstroms / second.

[0250] When the hole injection layer is formed using spin coating, the coating conditions can vary depending on the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, the coating speed can be about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and the temperature at which heat treatment is performed after coating to remove a solvent can be about 80°C to about 200°C.

[0251] 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.

[0252] The hole transport region may include m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-sulfonated styrene) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-sulfonated styrene) (PANI / PSS), compounds represented by formula 201, compounds represented by formula 202, or combinations thereof:

[0253]

[0254] Formula 201

[0255]

[0256] Formula 202

[0257]

[0258] Ar in Equation 201 101 and Ar 102 Each of these can be independently unsubstituted or substituted with at least one of the following: phenylene, cyclopentadienylene, indenylene, naphthylene, azuleylene, heptadienylene, acenaphtheylene, fluoreneylene, phenenylene, anthraceneylene, fluorenylene, benzo[9,10]phenenylene, pyreneylene, etc. alkyl, tetraphenylene, terephthalyl, perylene, or pentaphenylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C60 heteroaryl thiols, C2-C 60 Heteroalkyl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heterocyclic group.

[0259] In Equation 201, xa and xb can each be an integer from 0 to 5, or 0, 1, or 2. For example, xa can be 1, and xb can be 0.

[0260] In equations 201 and 202, R 101 -R 108 R 111 -R 119 and R 121 -R 124 Each can be independently:

[0261] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), or C1-C 10 Alkyl groups (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);

[0262] Each of the C1-C molecules is replaced by at least one of the following: 10 Alkyl or C1-C 10 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, or phosphate group or its salt; or

[0263] The phenyl, naphthyl, anthracene, fluorenyl, or pyrene group, respectively, is either unsubstituted or substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, or C1-C 10 Alkyl group.

[0264] In Equation 201, R 109 It may be a phenyl, naphthyl, anthracene, or pyridyl group, each unsubstituted or substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, anthraceneyl, or pyridyl.

[0265] In one embodiment, the compound represented by Formula 201 can be represented by Formula 201A:

[0266] Formula 201A

[0267]

[0268] In Formula 201A, R 101 , R 111 , R 112 , and R 109 may be understood by referring to the description provided herein.

[0269] For example, the hole transport region can include at least one of compounds HT1 to HT20:

[0270]

[0271]

[0272] The thickness of the hole transport region can be in the range of about - about For example, about - about When the hole transport region includes a hole injection layer, a hole transport layer, or a combination thereof, the thickness of the hole injection layer can be in the range of about - about For example, about - about and the thickness of the hole transport layer can be in the range of about about For example, about - about Without wishing to be bound by theory, when the thickness of the hole transport region, hole injection layer, and hole transport layer is in these ranges, satisfactory hole transport properties can be obtained without a significant increase in driving voltage.

[0273] In addition to these materials, the hole transport region can further include a charge generating material for improving the electrical conductivity properties. The charge generating material can be uniformly or non-uniformly dispersed in the hole transport region.

[0274] The charge generating material can be, for example, a p-dopant. The p-dopant can include a quinone derivative, a metal oxide, a compound including a cyano group, or a combination thereof. For example, non-limiting examples of the p-dopant can be: a quinone derivative such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4-TCNQ); a metal oxide such as tungsten oxide or molybdenum oxide; and a compound including a cyano group such as the following compound HT-D1.

[0275]

[0276] The hole transport region can further include a buffer layer.

[0277] Further, the buffer layer can compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, the light emitting efficiency of the organic light emitting device 10 can be improved.

[0278] Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer can include a material used in the hole transport region as described above, a host material described below, or a combination thereof. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer can be mCP described below.

[0279] Then, an emission layer can be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, although deposition or coating conditions can vary according to a material used to form the emission layer, the deposition or coating conditions can be similar to those applied when forming the hole injection layer.

[0280] The emission layer can include a host and a dopant, and the dopant can include an organometallic compound represented by Formula 1.

[0281] The host can include TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, or a combination thereof:

[0282]

[0283] When the organic light emitting device 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. In one or more embodiments, the emission layer can emit white light due to a stacked structure including a red emission layer, a green emission layer, and / or a blue emission layer.

[0284] When the emission layer includes a host and a dopant, the amount of the dopant can be in the range of about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the host.

[0285] The dopant can be an organometallic compound represented by Formula 1. For example, the dopant can be a green phosphorescent dopant.

[0286] The thickness of the emission layer can be in the range of about - about 100 nm For example, about 10 nm to about 100 nm - about Without being bound by theory, when the thickness of the electron transport region is within the range, the electron transport region can obtain excellent electron transport characteristics without a significant increase in driving voltage.

[0287] The electron transport region can then be located on the emission layer.

[0288] The electron transport region can include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0289] 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. The electron transport layer can have a multi-layer structure including two or more different materials or a single layer structure.

[0290] 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 conditions for forming the hole injection layer.

[0291] When the electron transport region includes a hole blocking layer, the hole blocking layer can include, for example, BCP, Bphen, BAlq, or a combination thereof.

[0292]

[0293] The thickness of the hole blocking layer can be within a range of about - about For example, the thickness of the hole blocking layer can be within a range of about - about Without being bound by theory, when the thickness of the hole blocking layer is within the range, the hole blocking layer can obtain excellent hole blocking characteristics without a significant increase in driving voltage.

[0294] The electron transport layer can include BCP, Bphen, Alq3, BAlq, TAZ, NTAZ, or a combination thereof.

[0295]

[0296] In one or more embodiments, the electron transport layer can include one of compounds ET1 to ET25 or a combination thereof.

[0297]

[0298]

[0299] The thickness of the electron transport layer can be within a range of about - about For example, the thickness of the electron transport layer can be within a range of about - about about 1 nm to about 10 nm. Without wishing to be bound by theory, when the thickness of the electron transport layer is within the range, the electron transport layer can obtain satisfactory electron transport characteristics without a significant increase in driving voltage.

[0300] In addition, the electron transport layer can further include a metal-containing material, in addition to the materials described above.

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

[0302]

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

[0304] The electron injection layer can include LiF, NaCl, CsF, Li2O, BaO, or a combination thereof.

[0305] The thickness of the electron injection layer can be in the range of about 0.1 nm to about 10 nm. Without wishing to be bound by theory, when the thickness of the electron injection layer is within the range, the electron injection layer can obtain satisfactory electron injection characteristics without a significant increase in driving voltage. about 0.1 nm to about 1 nm. for example, about 0.1 nm to about 0.5 nm. about 0.1 nm to about 1 nm. about 0.1 nm to about 1 nm. Without wishing to be bound by theory, when the thickness of the electron injection layer is within the range, the electron injection layer can obtain satisfactory electron injection characteristics without a significant increase in driving voltage.

[0306] The second electrode 19 can be located on the organic layer 15. The second electrode 19 can be a cathode. Materials used to form the second electrode 19 can include a metal, an alloy, a conductive compound, or a combination thereof, having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or a combination thereof can be used as the material used to form the second electrode 19. In one or more embodiments, in order to manufacture a top emission type light emitting device, a transmissive electrode formed using ITO, IZO, or a combination thereof can be used as the second electrode 19.

[0307] In the foregoing, an organic light emitting device has been described with reference to Figure 1 but exemplary embodiments of the present disclosure are not limited thereto.

[0308] According to another aspect, the organic light emitting device can be included in an electronic device. Accordingly, an electronic device including the organic light emitting device is provided. The electronic device can include, for example, a display, a lighting device, a sensor, etc.

[0309] According to another aspect, a diagnostic composition including at least one organometallic compound represented by Formula 1 is provided.

[0310] Organometallic compounds represented by Formula 1 provide high luminescence efficiency. Therefore, diagnostic compositions comprising said organometallic compounds can have high diagnostic efficiency.

[0311] The diagnostic composition can be used in a variety of applications, including diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0312] As used in this article, the term "C1-C" 60 "Alkyl" refers to a straight-chain or branched monovalent group of a saturated aliphatic hydrocarbon having 1-60 carbon atoms, and as used herein in the term "C1-C". 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Divalent groups with the same structure as alkyl groups.

[0313] C1-C 60 Alkyl, C1-C 20 Alkyl, and / or C1-C 10 Examples of alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl. Isodecyl, sec-decyl, or tert-decyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, or tert-decyl. For example, formula 9-33 is a branched C6 alkyl group, such as tert-butyl substituted with two methyl groups.

[0314] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups.

[0315] C1-C 60 Alkoxy, C1-C 20 alkoxy, or C1-C 10 Examples of alkoxy groups may include methoxy, ethoxy, propoxy, butoxy, or pentoxy.

[0316] As used in this article, the term "C2-C" 60 "Alkenyl" has the properties of C2-C 60 The alkyl group includes at least one carbon-carbon double bond at its middle or end, and examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to a group with a C2-C ratio. 60 Divalent groups with the same structure as alkenyl groups.

[0317] As used in this article, the term "C2-C" 60 "Alkyne group" has the characteristic of being in the C2-C 60 An alkyl group includes at least one carbon-carbon triple bond at its middle or end, and examples include ethynyl and propynyl groups. As used herein, the term "C2-C" is used... 60 "Alynyl group" refers to a group with a C2-C group. 60 Divalent groups with the same structure as alkynyl groups.

[0318] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3-10 carbon atoms, and the term "C3-C" is used in this context. 10 "Cycloalkylene" is a compound with C3-C66 atoms. 10 Divalent groups with the same structure as cycloalkyl groups.

[0319] As used in this article, the term "C3-C" 10 "Cycloalkyl" may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornel), bicyclo[2.2.2]octyl, etc.

[0320] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monocyclic group comprising at least one heteroatom selected from N, O, P, Si, S, Se, Ge, As, and B as a cyclic atom and 1-10 carbon atoms, and the term "C1-C" is used in this context. 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with the same structure as heterocyclic alkyl groups.

[0321] C1-C 10 Examples of heterocyclic alkyl groups may include silylcyclopentyl, silylcyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, tetrahydrothiophenyl, etc.

[0322] As used in this article, the term "C3-C" 10"Cycloalkenyl" refers to a monovalent monocyclic group having 3-10 carbon atoms and at least one carbon-carbon double bond in its ring and not being aromatic, and non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C3-C" is used as is herein. 10 "Cyclopentene" refers to a group with a C3-C6 bond structure. 10 A divalent group with the same structure as a cycloalkenyl group.

[0323] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, As, and B as the cyclic atom, 1-10 carbon atoms, and at least one carbon-carbon double bond in its ring. C1-C 10 Examples of heterocyclic alkenyl groups include 2,3-dihydrofuranyl and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to a group that has a C1-C2 bond structure. 10 Divalent groups with the same structure as heterocyclic alkenyl groups.

[0324] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system with 6-60 carbon atoms, and as used herein, "C6-C". 60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system with 6-60 carbon atoms. (C6-C) 60 Examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and... Base. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the rings may be fused together.

[0325] As used in this article, the term "C7-C" 60 "Alkyl" refers to an aryl group formed by at least one C1-C2 group. 54 Alkyl-substituted C6-C 59 Aryl. As used in this text, the term "C7-C" 60 "Aryl" refers to an alkyl group consisting of at least one C6-C2 group. 59 Aryl-substituted C1-C 54 alkyl.

[0326] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, As, and B as a cyclic atom and 1-60 carbon atoms in a cyclic aromatic system, and as used herein by the term "C1-C". 60"Heteroaryloxy" refers to -OA 60 Examples of heteroaryl groups include pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C 60 Examples of heteroaryl groups include pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C 60 When the heteroarylene groups each include two or more rings, the rings can be fused with one another.

[0327] The term "C2-Ci2alkenyl" as used herein denotes a straight or branched hydrocarbon chain radical, which contains at least one double bond and which has 2-12 carbon atoms. The term "C2-Ci2alkynyl" as used herein denotes a straight or branched hydrocarbon chain radical, which contains at least one triple bond and which has 2-12 carbon atoms. 60 "Alkylheteroaryl" refers to a C1-C 59 "Alkylheteroaryl" refers to a C1-C 59 heteroaryl group.

[0328] The term "C6-Ci2aryloxy" as used herein denotes an -OA 60 "Alkylheteroaryl" refers to a C1-C 102 (wherein A 102 represents a C6-C 60 aryl group), a C6-C 60 "Alkylheteroaryl" refers to a C1-C 103 (wherein A 103 represents a C6-C 60 aryl group), and a C1-C 60 "Alkylheteroaryl" refers to a C1-C 104 (wherein A 104 represents a C1-C 60 alkyl group).

[0329] The term "C1-Ci2alkyl" as used herein denotes a straight or branched, saturated, monovalent hydrocarbon chain radical, which has 1-12 carbon atoms. The term "C1-Ci2alkylene" as used herein denotes a straight or branched, saturated, divalent hydrocarbon chain radical, which has 1-12 carbon atoms. 60 "Heteroaryloxy" refers to -OA 106 (wherein A 106 is a C2-C 60 heteroaryl group), the term "C1-C 60 "Heteroaryloxy" refers to -OA 107 (wherein A 107 is a C1-C 60 heteroaryl group), and the term "C2-C 60 "Heteroaryloxy" refers to -OA 108 A 109 (A 109 is a C1-C 59 heteroaryl group, and A 108 is a C1-C 59 alkylene group).

[0330] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8-60 carbon atoms) that has two or more rings fused to each other, has only carbon atoms as ring-forming atoms, and has non-aromaticity in its entire molecular structure. Examples of monovalent non-aromatic fused polycyclic groups include fluorene groups. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.

[0331] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 1-60 carbon atoms) that has two or more rings fused to each other, has, in addition to carbon atoms, a heteroatom selected from N, O, P, Si, S, Se, Ge, As, and B as ring-forming atoms, and has non-aromaticity in its entire molecular structure. Examples of monovalent non-aromatic fused heteropolycyclic groups include carbazole groups. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as a monovalent non-aromatic fused heteropolycyclic group.

[0332] The term "C5-C 30 carbon ring group" refers to a saturated or unsaturated cyclic group having only 5-30 carbon atoms as ring-forming atoms. C5-C 30 A C5-C 10a carbon ring group can be a monocyclic group or a polycyclic group. A "(unsubstituted or substituted) C5-C 30 carbon ring group" can include (each unsubstituted or substituted with at least one R 10a adamantane group, norbornene group, bicyclo[l. l. l]pentane group, bicyclo[2. l. l]hexane group, bicyclo[2.2. l]heptane (norbornane) group, bicyclo[2.2.2]octane group, cyclopentane group, cyclohexane group, cyclohexene group, phenyl group, naphthyl group, anthryl group, phenanthryl group, benzo[9, 10]phenanthryl group, pyrene group, group, 1,2,3,4-tetrahydronaphthyl group, cyclopentadienyl group, and fluorene group.

[0333] The term "C1-C 30 heterocyclic group" refers to a saturated or unsaturated cyclic group having, in addition to 1-30 carbon atoms, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, As, and B as ring-forming atoms. C1-C 30 A C1-C 10a heterocyclic group can be a monocyclic group or a polycyclic group. A "(unsubstituted or substituted) C1-C 30The term "heteroaryl group" can include, for example, each of the groups mentioned above as "heteroaromatic group" which is unsubstituted or substituted by at least one R 10a substituted thiophene group, furan group, pyrrole group, silole group, borol group, phospholene group, selenophene group, germole group, benzothiophene group, benzofuran group, indole group, benzosilole group, benzo- borol group, benzo-phospholene group, benzo-selenophene group, benzo-germole group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzosilole group, dibenzoborol group, dibenzophospholene group, dibenzoselenophene group, dibenzogermole group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azacarbazole group, azabenzosilole group, azabenzoborol group, azabenzophospholene group, azabenzoselenophene group, azabenzogermole group, azadibenzothiophene group, azacarbazole group, azabenzosilole group, azabenzoborol group, azabenzophospholene group, azabenzoselenophene group, azabenzogermole group, azadibenzothiophene 5-oxide group, azacarbazole group, azabenzosilole group, azabenzoborol group, azabenzophospholene group, azabenzoselenophene group, azabenzogermole group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, dioxazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzisoxazole group, benzodioxazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, and 5,6,7,8-tetrahydroquinoline group. oxazole group, isoxazole group, thiazole group, isothiazole group, dioxazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzisoxazole group, benzodioxazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, and 5,6,7,8-tetrahydroquinoline group. dioxazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzisoxazole group, benzodioxazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, and 5,6,7,8-tetrahydroquinoline group. dioxazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzisoxazole group, benzodioxazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, and 5,6,7,8-tetrahydroquinoline group. dioxazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzisoxazole group, benzodioxazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, and 5,6,7,8-tetrahydroquinoline group.

[0334] The term "deuterated C1-C 60 alkyl (or C1-C 20 alkyl, etc.), C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, and "deuterated phenyl" each represent C1-C 60 alkyl (or C1-C 20 alkyl, etc.), C3-C 10 cycloalkyl, C1-C 10Heterocyclic alkyl groups and phenyl groups. For example, "deuterated C1 alkyl (i.e., deuterated methyl)" may include -CD3, -CD2H, and -CDH2, and "deuterated C3-C 10 Examples of "cycloalkyl" may refer to, for example, formula 10-501, etc. "Deuterated C1-C..." 60 Alkyl (or deuterated C1-C) 20 Alkyl groups, etc., and deuterated C3-C 10 "Cycloalkyl" or "deuterated C1-C" 10 "Heterocyclic alkyl" can be: i) fully deuterated C1-C 60 Alkyl (or fully deuterated C1-C) 20 Alkyl groups, etc., and fully deuterated C3-C 10 Cycloalkyl, or fully deuterated C1-C 10 Heterocyclic alkyl groups, wherein all hydrogen atoms in each group are replaced by deuterium, or ii) partially deuterated C1-C 60 Alkyl (or partially deuterated C1-C) 20 Alkyl groups, etc.), and partially deuterated C3-C 10 Cycloalkyl, or partially deuterated C1-C 10 Heterocyclic alkyl groups, wherein some hydrogen atoms in each group are replaced by deuterium, but not all hydrogen atoms included therein are replaced by deuterium.

[0335] As used in this article, the term "(C1-C" is similar to the term "(C1-C)" 20 "alkyl)'X' group" refers to a group consisting of at least one C1-C1 group. 20 Alkyl-substituted 'X' groups. For example, as used herein, the term "(C1-C1)" 20 Alkyl)C3-C 10 "Cycloalkyl" refers to a compound formed by at least one C1-C2 group. 20 Alkyl-substituted C3-C 10 cycloalkyl, and as used herein, the term "(C1-C1)" 20 "alkyl)phenyl" refers to a compound formed by at least one C1-C2 bond. 20 Alkyl-substituted phenyl groups. An example of (C1 alkyl)phenyl is tolyl.

[0336] The terms "azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzothiophene group, azabenzogermyl group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azaborenaphthindene group, azaborenaphthophosphole group, azafuorene group, azaborenzothiophene group, azaborenzogermyl group, azaborenzothiophene group, azaborenzoselenophene group, azaborenzofuran group, azabenzothiophene 5-oxide group, azo-9H-fluoren-9-one group, and azaborenzothiophene 5,5-dioxide group" each individually refer to a heterocyclic group having the same skeleton as "indole group, benzoborole group, benzophosphole group, indene group, benzothiophene group, benzogermyl group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, borenaphthindene group, borenaphthophosphole group, fuorene group, borenzothiophene group, borenzogermyl group, borenzothiophene group, borenzoselenophene group, borenzofuran group, borenzothiophene 5-oxide group, 9H-fluoren-9-one group, borenzothiophene group, and 5,5-dioxide group", wherein, in each group, at least one carbon selected from ring-forming carbons is replaced with nitrogen.

[0337] 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 C6-C 60 aryloxy, substituted C6-C 60 arylthio, substituted C7-C 60 aralkyl, substituted C1-C 60 heteroaryl, substituted C1-C 60 heteroaryloxy, substituted C1-C 60 heteroarylthio, substituted C2-C 60 heteroaralkyl, substituted C2-C60 substituents of substituted monovalent non-aromatic fused polycyclic groups, and substituted monovalent non-aromatic fused heteropolycyclic groups can each independently be:

[0338] deuterium, -F, -CI, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy;

[0339] C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy: deuterium, -F, -CI, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 alkylaryl, C1-C 60 heteroaryl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, C2-C 60 heteroalkyl, C2-C 60 alkylheteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), or -P(Q 18 )(Q 19 );

[0340] Each of the following C3-Cs is either not substituted or is substituted by at least one of the following: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroalkyl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -N(Q 21 (Q) 22 ), -Si(Q 23 (Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 ), or -P(Q 28 (Q) 29 );

[0341] -N(Q 31 (Q) 32 ), -Si(Q 33 (Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q) 38 (Q) 39 ), or -P(Q 38 (Q) 39 );or

[0342] Its combination.

[0343] As used in this article, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each of the following is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidine; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphate group or its salt; unsubstituted or deuterated, C1-C 60 Alkyl, or C6-C 60 At least one substituted C1-C of aryl 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkyl group; C3-C 10 cycloalkyl; C1-C 10 Heterocyclic alkyl; C3-C 10 Cycloalkenyl; C1-C 10 Heterocyclic alkenyl groups; unsubstituted or deuterated, C1-C 60 Alkyl, or C6-C 60 At least one substituted C6-C of aryl group 60 Aryl; C6-C 60 Aryloxy group; C6-C 60 Arylthio; C7-C 60 Aryl group; C1-C 60 heteroaryl; C1-C 60 Heteroaryloxy group; C1-C 60 heteroaryl thio; C2-C 60 Heteroalkyl; C2-C 60 Alkyl heteroaryl; monovalent non-aromatic fused polycyclic group; or monovalent non-aromatic fused heterocyclic group.

[0344] Hereinafter, the compounds and the organic light emitting device according to one or more exemplary embodiments will be described in further detail with reference to the synthetic examples and examples, but the present disclosure is not limited thereto. The phrase "use B instead of A" used in describing the synthetic examples means that the amount of A used is the same as the amount of B used in terms of molar equivalents.

[0345] EMBODIMENT

[0346] Synthetic Example 1 (Compound 1)

[0347] Scheme 1 shows the synthesis of Compound 1.

[0348] Scheme 1

[0349]

[0350] Synthesis of Compound 1-3

[0351] Compound 1-4 (33.1 millimoles (mmol)) and iridium chloride trihydrate (IrCl3(H2O)n, n=3) (5.2 grams (g), 14.7 mmol) were mixed with 120 milliliters (mL) of 2-ethoxyethanol and 40 mL of deionized water, and then the mixture was stirred under reflux for 24 hours and then cooled to room temperature. The solid material formed therefrom was separated by filtration and washed sufficiently with water, methanol, and hexane in the order stated to obtain a solid, which was then dried in a vacuum oven to obtain Compound 1-3 (85% yield).

[0352] Synthesis of Compound 1-2

[0353] Compound 1-3 (1.2 mmol) and 45 mL of dichloromethane (MC) were mixed, and silver trifluoromethanesulfonate (AgOTf) (0.6 g, 2.3 mmol) was mixed with 15 mL of methanol (MeOH) and then added thereto. Thereafter, the mixture was stirred at room temperature for 18 hours while being blocked from light by using aluminum foil, the solid formed therefrom was removed by filtration using diatomite, and the filtrate was evaporated under reduced pressure to obtain a solid (Compound 1-2), which was then used in the next reaction without further purification.

[0354] Synthesis of Compound 1

[0355] Compound 1-2 (2.3 mmol) and compound 1-1 (2.8 mmol) were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide, and the mixture was stirred under reflux for 48 hours, after which it was cooled. The mixture obtained therefrom was evaporated under reduced pressure to obtain a solid, which was then subjected to column chromatography (eluent: dichloromethane (MC) and hexane) to obtain compound 1 (45% yield). Compound 1 was confirmed by high resolution mass spectrometry (HRMS) and high performance liquid chromatography (HPLC) analysis.

[0356] HRMS (Matrix Assisted Laser Desorption Ionization, MALDI): for C 39 H 26 Calculated for IrN3O2: m / z 760.86, found: 761.30.

[0357] Synthesis Example 2 (Compound 2)

[0358] Scheme 2 shows the synthesis of compound 2.

[0359] Scheme 2

[0360]

[0361] Compound 2 was obtained in the same manner as used for the synthesis of compound 1 of Synthesis Example 1, except that compound 2-1 was used instead of compound 1-1 (55% yield). Compound 2 was confirmed by HRMS and HPLC analysis.

[0362] HRMS (MALDI): for C 45 H 30 Calculated for IrN3O2: m / z 836.96, found: 837.60.

[0363] Synthesis Example 3 (Compound 3)

[0364] Scheme 3 shows the synthesis of compound 3.

[0365] Scheme 3

[0366]

[0367] Compound 3 was obtained in the same manner as used for the synthesis of compound 1 of Synthesis Example 1, except that compound 3-1 was used instead of compound 1-1 (50% yield). Compound 3 was confirmed by HRMS and HPLC analysis.

[0368] HRMS (MALDI): for C 42 H 32Calculated for IrN3O2: m / z 787.22, found: 788.15.

[0369] Synthesis Example 4 (Compound 4)

[0370] Scheme 4 shows the synthesis of Compound 4.

[0371] Scheme 4

[0372]

[0373] Compound 4 was obtained in the same manner as used for the synthesis of Compound 1 of Synthesis Example 1, except that Compound 4-1 was used instead of Compound 1-1, except as follows. Compound 4 was confirmed by HRMS and HPLC analysis.

[0374] HRMS (MALDI): for C 39 H 26 Calculated for IrN3O2: m / z 760.86, found: 761.35.

[0375] Synthesis Example 5 (Compound 5)

[0376] Scheme 5 shows the synthesis of Compound 5.

[0377] Scheme 5

[0378]

[0379] Synthesis of Compound 5-3

[0380] Compound 5-3 was obtained in the same manner as used for the synthesis of Compound 1-3 of Synthesis Example 1, except that Compound 4-1 was used instead of Compound 1-4, except as follows (50% yield).

[0381] Synthesis of Compound 5-2

[0382] Compound 5-2 was obtained in the same manner as used for the synthesis of Compound 1-2 of Synthesis Example 1, except that Compound 5-3 was used instead of Compound 1-3, except as follows, which was then used in the next reaction without further purification.

[0383] Synthesis of Compound 5

[0384] Compound 5 was obtained in the same manner as used for the synthesis of Compound 1 of Synthesis Example 1, except that Compound 5-2 and Compound 1-4 were used instead of Compound 1-2 and Compound 1-1, respectively, except as follows (50% yield). Compound 5 was confirmed by HRMS and HPLC analysis.

[0385] HRMS (MALDI): for C45 H 28 Calculated value of IrN3O4: m / z 866.94, measured value: 867.23.

[0386] Synthesis Example 6 (Compound 6)

[0387] Scheme 6 shows the synthesis of compound 6.

[0388] Option 6

[0389]

[0390] Compound 6 (45% yield) was obtained in the same manner as compound 1 used in synthesis example 1, except that compound 6-1 was used instead of compound 1-1. Compound 6 was confirmed by HRMS and HPLC analysis.

[0391] HRMS (MALDI): For C 39 H 26 Calculated value of IrN3OS: m / z 776.93, measured value: 777.56.

[0392] Synthesis Example 7 (Compound 7)

[0393] Scheme 7 shows the synthesis of compound 7.

[0394] Option 7

[0395]

[0396] Compound 7 (50% yield) was obtained in the same manner as compound 1 used in synthesis Example 1, except that compound 7-1 was used instead of compound 1-1. Compound 7 was confirmed by HRMS and HPLC analysis.

[0397] HRMS (MALDI): For C 42 H 38 The calculated value of IrN3O2Si is 833.04, and the measured value is 833.97.

[0398] Synthesis Example 8 (Compound 8)

[0399] Scheme 8 shows the synthesis of compound 8.

[0400] Option 8

[0401]

[0402] Synthesis of compound 8-3

[0403] Compound 8-3 was obtained in the same manner as used for the synthesis of compound 1-3 of Synthetic Example 1, except that compound 8-4 was used instead of compound 1-4.

[0404] Synthesis of compound 8-2

[0405] Compound 8-2 was obtained in the same manner as used for the synthesis of compound 1-2 of Synthetic Example 1, except that compound 8-3 was used instead of compound 1-3, which was then used in the next reaction without further purification.

[0406] Synthesis of compound 8

[0407] Compound 8 was obtained in the same manner as used for the synthesis of compound 1 of Synthetic Example 1, except that compound 8-2 and compound 1-4 were used instead of compound 1-2 and compound 1-1, respectively. Compound 8 was confirmed by HRMS and HPLC analysis.

[0408] HRMS (MALDI): for C 51 H 44 IrN3O4Si2calcd: m / z 1011.33, found: 1012.25.

[0409] Synthetic Example 9 (compound 9)

[0410] Scheme 9 shows the synthesis of compound 9.

[0411] Scheme 9

[0412]

[0413] Compound 9 was obtained in the same manner as used for the synthesis of compound 1 of Synthetic Example 1, except that compound 9-1 was used instead of compound 1-1. Compound 9 was confirmed by HRMS and HPLC analysis.

[0414] HRMS (MALDI): for C 48 H 34 IrN3O2calcd: m / z 911.11, found: 912.30.

[0415] Example 1

[0416] ITO was deposited on a glass substrate to a thickness of 1500 A The glass substrate, with a thickness of 0.5 mm, was cut into 50 mm × 50 mm × 0.5 mm pieces and ultrasonically treated with isopropanol and pure water for 5 minutes each. It was then cleaned by irradiation with ultraviolet light and exposure to ozone for 30 minutes. The resulting glass substrate was then mounted onto a vacuum deposition apparatus.

[0417] 2-TNATA was vacuum deposited on the anode to form a structure with A hole injection layer of a certain thickness is formed, and 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) is vacuum-deposited onto the hole injection layer to form a layer with [missing information]. A hole transport layer of a certain thickness.

[0418] Subsequently, CBP (the host) and Compound 1 (the dopant) were co-deposited on the hole transport layer at a weight ratio of 90:10 to form a structure with... The thickness of the emission layer.

[0419] Subsequently, BCP is vacuum deposited on the emitter layer to form a structure with... A hole-blocking layer of a certain thickness is formed, and Alq3 is vacuum-deposited onto the hole-blocking layer to form a hole-blocking layer with a thickness of [missing information]. An electron transport layer of a certain thickness is formed by vacuum deposition of LiF onto the electron transport layer to create an electron transport layer with a thickness of [missing information]. An electron-injected layer of a certain thickness is formed, and Al is deposited on the electron-injected layer to form a layer with [missing information]. A cathode of a certain thickness is used to complete the fabrication of organic light-emitting devices.

[0420]

[0421] Examples 2 to 9 and Comparative Examples A to C

[0422] The organic light-emitting device was manufactured in the same manner as in Example 1, except that, when forming the emission layer, the corresponding compounds shown in Table 10 were used instead of compound 1 as dopants.

[0423] Evaluation Example 1: Characteristic Evaluation of Organic Light-Emitting Devices

[0424] For each organic light-emitting device fabricated in Examples 1 to 9 and Comparative Examples A to C, the driving voltage (V), maximum external quantum efficiency (maximum EQE, %), half-width at half maximum (FWHM) of the main peak in the electroluminescence (EL) spectrum, and maximum emission wavelength (nm) were evaluated, and the results are shown in Table 10. A voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation equipment.

[0425] Table 10

[0426]

[0427]

[0428]

[0429] Referring to Table 10, the organic light-emitting devices manufactured according to Examples 1 to 9 emit green light and at the same time have improved driving voltage, improved external quantum efficiency, and improved FWHM of the main peak in the EL spectrum compared to the organic light-emitting devices manufactured according to Comparative Examples A to C.

[0430] The organic metal compound has excellent electrical properties, and thus an electronic device including the organic metal compound, for example, an organic light-emitting device, can have improved properties in terms of driving voltage, luminous efficiency, and / or FWHM of the main peak in the EL spectrum.

[0431] It should be understood that the exemplary implementations described herein are considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each exemplary implementation should typically be considered as being applicable in, and Figure 1 One or more exemplary implementations are described herein, but those of ordinary skill in the art will readily devise variations without departing from the scope of the present disclosure as defined by the appended claims.

Claims

1. Organometallic compounds represented by Formula 1: Formula 1 M(L1) n1 (L2) n2 wherein, In Equation 1, M is Ir, L1 is a ligand represented by equation 2-1(1), 2-2(1), or 2-3(1). n1 is either 1 or 2, where when n1 is 2, the two ligands L1 are either the same or different from each other. L2 is the ligand represented by Equation 3-1. n2 is 1 or 2, where when n2 is 2, the two ligands L2 are either the same or different from each other, and L1 and L2 are different from each other. The sum of n1 and n2 is 3. Among them, in equations 2-1(1), 2-2(1), and 2-3(1), X1is O, S, Se, or C(R 31 )(R 32 ), X2is O, S, Se, or C(R 33 )(R 34 ), At least one of X1 and X2 is O, S, or Se. Y1 is N, Y2 is C. The CY2 ring can be a phenyl group, a dibenzofuran group, or a dibenzothiophene group. R1 is: hydrogen, deuterium, -F, -CI, -Br, -I, cyano, C1-C 20 alkyl, or C1-C 20 alkoxy; C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, or naphthyl groups, each unsubstituted or substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, or C1-C 20 Alkoxy R 12 is: hydrogen, deuterium, -F, -CI, -Br, -I, cyano, C1-C 20 alkyl, or C1-C 20 alkoxy; C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), Q3-Q5 are each independent of the following: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or Each was not replaced or replaced by deuterium or C1-C 20 At least one substituted alkyl group is n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, or sec-isopentyl. R2, R 11 , R 13 , R 14 , and R 31 - R 34 each independently is: hydrogen, deuterium, -F, -CI, -Br, -I, cyano, C1-C 20 alkyl, or C1-C 20 alkoxy; or C1-C4alkyl or C1-C4haloalkyl each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl each substituted by at least one substituent selected from the group consisting of: wherein R 31 and R 33 is not hydrogen, a1 is an integer from 0 to 4, where when a1 is 2 or greater, two or more groups R1 are either the same or different from each other. a2 is an integer from 0 to 10, where when a2 is 2 or greater, two or more groups R2 are either the same or different from each other. in formulae 2-1(1), 2-2(1), and 2-3(1) and each independently represents a binding site to M in formula 1, In Equation 3-1, Y 11 is N, Y 12 is C, Z 11 -Z 14 the same as described above for R2, and each represents a binding site to M in Formula 1, and In Equation 3-1, the The group represented is one of the groups represented by formulas 3-1(1) to 3-1(16): ， In equations 3-1(1) to 3-1(16), Z 21 -Z 24 The same as described above for Z 11 , wherein Z 21 -Z 24 is not hydrogen, represents the binding site to M in formula 1, and " represents a bonding site to an adjacent atom, The organometallic compounds mentioned above do not include the following compounds: 。 2. The organometallic compound of claim 1, wherein L1 is a ligand represented by formula 2-3(1), R 12 -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), and Wherein Q3-Q5 are the same as those described in claim 1.

3. The organometallic compound of claim 1, wherein the compounds of formulas 2-1(1), 2-2(1) and 2-3(1) are derived from... the group represented by formula CY2-1 and CY2-20 to CY2-25: wherein In formulas CY2-1 and CY2-20 to CY2-25, Y2 and R2 are each identical to those described in claim 1. X 22 is O or S, a26 is an integer between 0 and 6. a24 is an integer between 0 and 4. "denotes the binding site to the adjacent atom in formulae 2-1 (1), 2-2 (1) and 2-3 (1), and represents the binding site to M in Formula 1.

4. Organometallic compounds represented by Formula 1: Formula 1 M(L1) n1 (L2) n2 wherein In Equation 1, M is Ir, L1 is a ligand represented by equation 2-1(1), 2-2(1), or 2-3(1). n1 is either 1 or 2, where when n1 is 2, the two ligands L1 are either the same or different from each other. L2 is the ligand represented by Equation 3-1. n2 is 1 or 2, where when n2 is 2, the two ligands L2 are either the same or different from each other, and L1 and L2 are different from each other. The sum of n1 and n2 is 3. In equations 2-1(1) and 2-2(1), X1is O, S, Se, or C(R 31 )(R 32 ), X2is O, S, Se, or C(R 33 )(R 34 ), At least one of X1 and X2 is O, S, or Se. Y1 is N, Y2 is C. The CY2 ring can be a phenyl group, a dibenzofuran group, or a dibenzothiophene group. R1 is: hydrogen, deuterium, -F, -CI, -Br, -I, cyano, C1-C 20 alkyl, or C1-C 20 alkoxy; C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: 20 C1-C4alkyl or C1-C4haloalkyl, each substituted by at least one substituent selected from the group consisting of: Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, or naphthyl groups, each unsubstituted or substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, or C1-C 20 Alkoxy R2, R 11 , R 13 , R 14 , and R 31 - R 34 each independently is: hydrogen, deuterium, -F, -CI, -Br, -I, cyano, C1-C 20 alkyl, or C1-C 20 alkoxy; or Each of the C1-Cs is replaced by at least one of the following: 20 Alkyl or C1-C 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl or deuterated C1-C 20 alkyl, wherein R 31 and R 33 are not hydrogen, a1 is an integer from 0 to 4, where when a1 is 2 or greater, two or more groups R1 are either the same or different from each other. a2 is an integer from 0 to 10, wherein, when a2 is 2 or more, two or more groups R2 are the same as or different from each other, and in formulae 2-1 (1) and 2-2 (1) and each independently represents a binding site to M in formula 1, in formula 2-3(1), X1, X2, Y1, Y2, ring CY2, a1, a2, and each independently as described for formula 2-1 (1) and 2-2 (1), at least one of X1and X2is O, S, or Se, and R1, R2, R 11 and R 12 satisfy definition (1) or definition (2): Definition (1): R 12 -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), wherein Q3-Q5are each independently: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or each R1is independently H, C1-C6alkyl, C1-C6haloalkyl, C1-C6deuteroalkyl, C1-C6hydroxyalkyl, C1-C6aminoalkyl, or C3-C6cycloalkyl; 20 each R1is independently H, C1-C6alkyl, C1-C6haloalkyl, C1-C6deuteroalkyl, C1-C6hydroxyalkyl, C1-C6aminoalkyl, or C3-C6cycloalkyl; R1, R2and R 11 each independently as described for formula 2-1 (1) and 2-2 (1), Definition (2): R1, R2, R 11 and R 12 each is hydrogen, wherein, in formula 3-1, Y 11 is N, Y 12 is C, Z 11 -Z 14 the same as described above for R2, and each represents a binding site to M in Formula 1, and In Equation 3-1, the The group represented is one of the groups represented by formulas 3-1(1) to 3-1(16): ， wherein, in formula 3-1(1) to 3-1(16), Z 21 -Z 24 The same as described above for Z 11 , wherein Z 21 -Z 24 is not hydrogen, represents the binding site to M in formula 1, and "indicates the bonding site to the adjacent atom.

5. The organometallic compound of claim 1 or 4, wherein, in formula 2-1(1), 2-2(1), and 2-3(1), X1is C(R 31 )(R 32 ), and X2is O, S, or Se; or X1is O, S, or Se, and X2is C(R 33 )(R 34 ).

6. The organometallic compound of claim 1 or 4, wherein R1, R2, R... 11 R 13 R 14 and R 31 -R 34 The definition of deuterated C1-C 20 Each alkyl group is independently -CD3, -CD2H, or -CDH2.

7. The organometallic compound according to claim 1 or 4, wherein the compound in formula 3-1 is composed of... The group represented is one of the groups represented by formulas 3-1-1 to 3-1-16: wherein in formula 3-1-1 to 3-1-16, Y 11 and Z 11 -Z 14 is the same as described in claim 1, wherein Z 11 -Z 14 is not hydrogen, represents the binding site to M in Formula 1, and "indicates the bonding site to the adjacent atom.

8. The organometallic compound according to claim 1 or 4, wherein the organometallic compound is one of compounds 1 to 12, 14, 16 to 18, 20, 22 to 24, 28 to 30, 32, 34 to 36, 38, 40 to 42, 46 to 48, 50, 52 to 54, 56, 58 to 60, 64 to 66, 68, 70 to 72, 74, 76 to 78, 82, 83, 86 to 88, 90, 92 to 94, 98 to 100, 102, 104 to 106, 108, 110, 111, 115 to 117, 119, 121 to 123, 125, 127 to 129, 133 to 135, 137, 139 to 141, 143, 145 to 147, 151, 153, 155 to 157, 159, 161 to 163, 167 to 169, 171, 173 to 175, 177, 179 to 181, 185, 186, 188, 190 to 192, 194, 196 to 198, 202 to 204, 206, 208 to 210, 212, 214 to 216, 220, 221, 223, 225 to 227, 229, 231 to 233, 237 to 239, 241, 243 to 245, 247, 249 to 251, 255, 256, 258, 260 to 262, 264, 266 to 268, 272 to 274, 276, 278 to 280, 282, and 284 to 286: Compounds 10 to 12, 14, 16 to 18, 20, 22 to 24, 28 to 30, 32, 34 to 36, 38, 40 to 42, 46 to 48, 50, 52 to 54, 56, 58 to 60, 64 to 66, 68, 70 to 72, 74, 76 to 78, 82, 83, 86 to 88, 90, 92 to 94, 98 to 100, 102, 104 to 106, 108, 110, 111, 115 to 117, 119, 121 to 123, 125, 127 to 129, 133 to 135, 137, 139 to 141, 143, 145 to 147, 151, 153, 155 to 157, 159, 161 to 163, 167 to 169, 171, 173 to 175, 177, 179 to 181, 185, 186, 188, 190 to 192, 194, 196 to 198, 202 to 204, 206, 208 to 210, 212, 214 to 216, 220, 221, 223, 225 to 227, 229, 231 to 233, 237 to 239, 241, 243 to 245, 247, 249 to 251, 255, 256, 258, 260 to 262, 264, 266 to 268, 272 to 274, 276, 278 to 280, 282, and 284 to 286 are represented by Formula 1, wherein M is Ir, L2is a phenyl-pyridine ligand, and L1, n1, and n2are each as defined in Tables 1 to 8, In Tables 1 to 8, Me is methyl, TMS is trimethylsilyl, and Formulas 2-1(1), 2-2(1), and 2-3(1) are: In formulae 2-1(1), 2-2(1), and 2-3(1), and each represents a binding site to M in formula 1, and CY2-1(1) and CY2-1(2) have the following formulas: In formulae CY2-1 (1) and CY2-1 (2), represents the bonding site to M in formula 1, and represents the bonding site to the adjacent atom, Table 1 Table 2 Table 3 Table 4 Table 5 Table 6 Table 7 Table 8 。 9. The organometallic compound of claim 4, wherein the compounds in formulas 2-1(1) and 2-2(1) are derived from... The indicated group is a group represented by one of the formulas CY2-1 and CY2-20 to CY2-25: wherein, In Formulas CY2-1 and CY2-20 to CY2-25, Y2and R2are each the same as described in Claim 4, X 22 is O or S, a26is an integer from 0 to 6, a24is an integer from 0 to 4, "denotes the binding site to the adjacent atom in formulae 2-1 (1) and 2-2 (1), and represents the binding site to M in Formula 1.

10. The organometallic compound of claim 4, wherein the compound in formula 2-3(1) is composed of... The indicated group is a group represented by one of the formulas CY2-1 and CY2-20 to CY2-25. wherein, In Formulas CY2-1 and CY2-20 to CY2-25, Y2is the same as described in Claim 4, R2is the same as described in definition (1) or (2) in Claim 4, X 22 is O or S, a26is an integer from 0 to 6, a24is an integer from 0 to 4, "denotes the binding site to the adjacent atom in formula 2-3(1), and represents the binding site to M in Formula 1.

11. An organic light emitting device comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and comprising an emissive layer, wherein the organic layer comprises at least one organometallic compound as described in any one of Claims 1 to 10.

12. The organic light emitting device of Claim 11, wherein the first electrode is an anode, the second electrode is a cathode, the organic layer further comprises a hole transport region disposed between the first electrode and the emissive layer and an electron transport region disposed between the emissive layer and the second electrode, the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region comprises an electron injection layer, an electron transport layer, a hole blocking layer, a buffer layer, or a combination thereof. The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

13. The organic light emitting device of claim 11, wherein the emissive layer includes the at least one organometallic compound.

14. An electronic device comprising the organic light emitting device of any one of claims 11-13.

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