Organometallic compound, organic light-emitting device comprising the same, and diagnostic composition comprising the organometallic compound

Abstract

Provided are an organometallic compound, an organic light-emitting device comprising the same, and a diagnostic composition comprising the organometallic compound. The organometallic compound is represented by Formula 1. In Formula 1, Ln1 is a ligand represented by Formula 1-1, Ln2 is a ligand represented by Formula 1-2, and other substituents and parameters are as described in the detailed description. Formula 1M1(Ln1) n1 (Ln2) n2 #imgabs0#

Description

[0001] Cross-reference to related applications

[0002] This application claims the benefit of Korean Patent Application No. 10-2020-0139747 filed on October 26, 2020, in the Korean Intellectual Property Office, the contents of which are incorporated herein by reference in their entirety. Technical Field

[0003] One or more embodiments relate to an organometallic compound, an organic light-emitting device including the same, and a diagnostic composition including the same. Background Art

[0004] Organic light emitting devices are self-emitting devices that have improved characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed and produce full-color images.

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

[0006] One or more embodiments relate to an organometallic compound, an organic light-emitting device including the same, and a diagnostic composition including the same.

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

[0008] Provided is an organometallic compound represented by Formula 1

[0009] Formula 1

[0010] M1(Ln1) n1 (Ln2) n2 ,

[0011] In formula 1,

[0012] M1 is a transition metal,

[0013] Ln1 is a ligand represented by formula 1-1,

[0014] Ln2 is a ligand represented by formula 1-2,

[0015] n1 is 0, 1, or 2,

[0016] n2 is 1, 2, or 3,

[0017]

[0018] In formulas 1-1 and 1-2,

[0019] X1 is C or N, and X2 is C or N,

[0020] Y1 is C(R 41 ) or N, Y2 is C(R 42 ) or N, Y3 is C(R 43 ) or N, Y4 is C(R 44 ) or N, Y5 is C(R 45 ) or N, Y6 is C(R 46 ) or N, Y7 is C(R 47 ) or N, Y8 is C(R 48 ) or N, Y9 is C(R 49 ) or N, and Y 10 C(R 50 ) or N,

[0021] CY1 and CY2 are each independently C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups,

[0022] CY3 is C1-C containing N 30 Heterocyclic groups,

[0023] R 10 、R 20 、R 30 and R 41 -R 50 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), or -P(═O)(Q8)(Q9),

[0024] At least one of the ligand represented by Formula 1-1, the ligand represented by Formula 1-2, or a combination thereof includes one or more -Ge(Q1)(Q2)(Q3),

[0025] Multiple R 10 Two or more of are optionally combined (bonded) together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups,

[0026] Multiple R 20 Two or more of are optionally combined together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups,

[0027] Multiple R 30 Two or more of are optionally combined together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups,

[0028] R 10 、R 20 、R 30 , and R 41 -R 50 Two or more adjacent groups of optionally combine with each other to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups,

[0029] b10, b20, and b30 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10,

[0030] Substituted C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C2-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is:

[0031] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, or C1-C 60 Alkoxy,

[0032] C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60Heteroarylthio group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 ),-Ge(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 ),-P(=O)(Q 18 )(Q 19 ), or a combination thereof,

[0033] C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 a heteroarylthio group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group,

[0034] Each of C3-C substituted 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, 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, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 ),-Ge(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ),-P(=O)(Q 28 )(Q 29 ), or a combination thereof, or

[0035] -Si(Q 31 )(Q 32 )(Q 33 ),-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 ), or -P(=O)(Q 38 )(Q 39 ),

[0036] Among them, Q1-Q9, Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 Each of them can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0037] Another aspect provides an organic light emitting device including a first electrode, a second electrode, and an organic layer including an emission layer located between the first electrode and the second electrode, wherein the organic layer includes at least one of the organometallic compounds.

[0038] The organometallic compound may be included in the emission layer of the organic layer, and the organometallic compound included in the emission layer may serve as a dopant.

[0039] Another aspect provides a diagnostic composition comprising at least one organometallic compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] By combining Figure 1 The above and other aspects, features and advantages of certain embodiments of the present disclosure will become more apparent upon consideration of the following description. Figure 1 A schematic cross-sectional view of an organic light emitting device according to an exemplary embodiment is shown. DETAILED DESCRIPTION

[0041] Embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the specification. In this regard, the present embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the following description of the embodiments is to illustrate aspects only by reference to the accompanying drawings. As used herein, the term "and / or" includes any and all combinations of one or more of the relevant enumerated items. Expressions such as "at least one (kind)" when before or after a list of elements modify the entire list of elements and do not modify the individual elements of the list.

[0042] 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 may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.

[0043] It will be understood that although the terms "first," "second," "third," etc., may be used herein to describe various elements, components, regions, layers, and / or portions, these elements, components, regions, layers, and / or portions should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer, or portion from another element, component, region, layer, or portion. Thus, without departing from the teachings herein, a "first element," "component," "region," "layer," or "portion" discussed below may be referred to as a second element, component, region, layer, or portion.

[0044] The terms used herein are for the purpose of describing specific embodiments only and are not intended to be limiting. As used herein, “a,” “an,” “the,” and “at least one” do not indicate a limitation of quantity and are intended to cover both the singular and the plural, unless the context clearly indicates otherwise. For example, “an element” has the same meaning as “at least one element,” unless the context clearly indicates otherwise.

[0045] "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. It will be further understood that the terms "comprise" or "include" when used in this specification indicate the presence of the stated features, regions, integers, steps, operations, elements and / or components, but do not preclude the presence or addition of one or more additional features, regions, integers, steps, operations, elements, components, and / or combinations thereof.

[0046] In addition, relative terms such as "lower" or "bottom" and "upper" or "top" may be used herein to describe the relationship of one element to another element as shown in the figures. It will be understood that relative terms are intended to include different orientations of the device in addition to the orientations shown in the figures. For example, if the device in one of the figures is turned over, the element described as being on the "lower" side of the other element will be oriented on the "upper" side of the other element. Therefore, depending on the specific orientation of the figure, the exemplary term "lower" may include both "lower" and "upper" orientations. Similarly, if the device in one of the figures is turned over, the element described as being "below" or "beneath" the other element will be oriented "above" the other element. Therefore, the exemplary terms "below" or "beneath" may include both "above" and "below" orientations.

[0047] As used herein, "about" or "approximately" is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, taking into account the measurements in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±10% or 5% relative to the stated value.

[0048] 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 disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and this disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly defined as such herein.

[0049] Exemplary embodiments are described herein with reference to cross-sectional views that are schematic representations of idealized embodiments. As such, deviations from the shapes of the figures are to be expected as a result of, for example, manufacturing techniques and / or tolerances. Therefore, the embodiments described herein should not be construed as limited to the specific shapes of the regions as illustrated herein, but rather include deviations in shape resulting from, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. Furthermore, illustrated sharp corners may be rounded. Therefore, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of the regions and are not intended to limit the scope of the claims.

[0050] One aspect of the present disclosure provides an organometallic compound represented by the following Formula 1:

[0051] Formula 1

[0052] M1(Ln1) n1 (Ln2) n2

[0053] M1 in Formula 1 may be a transition metal.

[0054] For example, M1 may be a period 1 transition metal, a period 2 transition metal, or a period 3 transition metal of the periodic table.

[0055] In an embodiment, M1 may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0056] In an embodiment, M1 may be Ir, Pt, Os, or Rh.

[0057] In an embodiment, M1 may be Ir.

[0058] In Formula 1, n1 may be 1 or 2, and n2 may be 1, 2, or 3.

[0059] In an embodiment, the sum of n1 and n2 may be 2 or 3.

[0060] In an embodiment, M1 may be Ir, and the sum of n1 and n2 may be 3.

[0061] In an embodiment, M1 may be Pt, and the sum of n1 and n2 may be 2.

[0062] Ln1 in Formula 1 may be a ligand represented by Formula 1-1.

[0063] Formula 1-1

[0064]

[0065] Ln2 in Formula 1 may be a ligand represented by Formula 1-2.

[0066] Formula 1-2

[0067]

[0068] In Formula 1-1, X1 may be C or N, and X2 may be C or N.

[0069] In formula 1-2, Y1 can be C(R 41 ) or N, Y2 may be C(R 42 ) or N, Y3 may be C(R 43 ) or N, Y4 may be C(R 44 ) or N, Y5 may be C(R 45 ) or N, Y6 can be C(R 46 ) or N, Y7 may be C(R 47 ) or N, Y8 may be C(R 48 ) or N, Y9 may be C(R 49 ) or N, and Y 10 Can be C(R 50 ) or N.

[0070] CY1 and CY2 in Formula 1-1 can each independently be C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic group.

[0071] CY3 in Formula 1-2 can be a C1-C 30 Heterocyclic group.

[0072] In an embodiment, rings CY1 and CY2 may be i) a first ring, ii) a second ring, iii) a fused ring group in which two or more first rings are fused to each other, iv) a fused ring group in which two or more second rings are fused to each other, or v) a fused ring group in which at least one first ring is fused to at least one second ring,

[0073] The first ring can be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, Azole group, iso Azole group, Oxadiazole group, iso oxadiazole group, Triazole group, isothiocyanate a triazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiole group, a diazathiole group, or a triazathiole group, and

[0074] The second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0075] In an embodiment, CY1 and CY2 may each independently be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, cyclopentadiene group, 1,2,3,4-tetrahydronaphthalene group, thiophene group, selenophene group, boropentadiene group, phosphole group, thiole group, germanium heterocyclopentadiene group, furan group, indole group, benzoborole group, benzophosphole group, indene group, benzothiole group, benzogermanium heterocyclopentadiene group, benzothiophene group, benzoselenophene group, benzofuran group , carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzosilole group, dibenzogermanol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzene group azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermanol group, azadibenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermanol group, azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, Azole group, iso azole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo Azole group, benzothiazole group, benzo an oxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

[0076] In an embodiment, CY1 and CY2 may each independently be a phenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

[0077] In an embodiment, CY1 may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group.

[0078] In an embodiment, CY2 may be a phenyl group, a naphthyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group.

[0079] In an embodiment, CY3 may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group.

[0080] R in Formula 1 10 、R 20 、R 30 , and R 41 -R 50 Each of them can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 heteroarylthio 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), or -P(═O)(Q8)(Q9).

[0081] Multiple R 10Two or more of may optionally be combined together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic group.

[0082] Multiple R 20 Two or more of may optionally be combined together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic group.

[0083] Multiple R 30 Two or more of may optionally be combined together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic group.

[0084] R 10 、R 20 、R 30 , and R 41 -R 50 Two or more adjacent groups of may optionally be combined together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 In this case, multiple R 10 Two or more, multiple R 20 Two or more, or multiple R 30 The case where two or more are optionally combined together.

[0085] b10, b20, and b30 in Formula 1 may each independently be 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0086] In an embodiment, b10, b20, and b30 may each independently be 1, 2, 3, 4, 5, 6, 7, or 8.

[0087] In an embodiment, b10, b20, and b30 may each independently be 1, 2, 3, or 4.

[0088] In an embodiment, b10, b20, and b30 may each independently be 1 or 2.

[0089] In an embodiment, b10, b20, and b30 may each independently be 1.

[0090] Formula 1-1 or Formula 1-2 may include one or more -Ge(Q1)(Q2)(Q3).

[0091] In an embodiment, the ligand Ln1 represented by Formula 1-1 may include one or more -Ge(Q1)(Q2)(Q3). In an embodiment, the ligand Ln2 represented by Formula 1-2 may include one or more -Ge(Q1)(Q2)(Q3).

[0092] In an embodiment, R 10 、R 20 、R 30 and R 41 -R 50 Each of them can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF5, C1-C 20 Alkyl, or C1-C 20 alkoxy;

[0093] C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, or pyrimidinyl;

[0094] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl;

[0095] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or a combination thereof; or

[0096] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9).

[0097] In an embodiment, R 10 、R 20 、R 30 , and R 41 -R 50 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5); or

[0098] A group represented by one of formulae 9-1 to 9-61, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350:

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106] In formulae 9-1 to 9-61, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, * represents a bonding site with an adjacent atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group.

[0107] In an embodiment, Q1-Q9, Q 11 -Q 19 , Q 21 -Q 29 and Q 31 -Q 39 Can be independently:

[0108] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0109] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0110] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with deuterium, C1-C 10 alkyl, phenyl, or a combination thereof.

[0111] In an embodiment, CY1 in Formula 1-1 may be represented by one of Formulas 1-1 to 1-16:

[0112]

[0113] Among them, in formulas 1-1 to 1-16,

[0114] R 11 -R 14 each independently represents deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, naphthyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3),

[0115] Q1-Q3 can each independently be:

[0116] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

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

[0118] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with deuterium, C1-C 10 Alkyl, phenyl, or a combination thereof, and

[0119] * and *' each represent a binding site with an adjacent atom.

[0120] In an embodiment, CY2 in Formula 1-1 may be represented by one of Formulas 2-1 to 2-16:

[0121]

[0122] Among them, in formulas 2-1 to 2-16,

[0123] R 21 -R 24 each independently represents deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, naphthyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3),

[0124] Q1-Q3 can each independently be:

[0125] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0126] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0127] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with deuterium, C1-C 10 Alkyl, phenyl, or a combination thereof, and

[0128] * and *' each represent a binding site with an adjacent atom.

[0129] In an embodiment, CY3 in Formula 1-2 may be represented by one of Formulas 3-1 to 3-40:

[0130]

[0131]

[0132] Among them, in formulas 3-1 to 3-40,

[0133] R 31 -R 34 each independently represents deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, naphthyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3),

[0134] Q1-Q3 can each independently be:

[0135] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0136] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0137] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with deuterium, C1-C 10 Alkyl, phenyl, or a combination thereof, and

[0138] * and *' each represent a binding site with an adjacent atom.

[0139] In an embodiment, the organometallic compound may be a compound represented by the following Formula 11-1:

[0140] <Formula 11-1>

[0141]

[0142] M1, n1, n2, and Y1-Y 10 Each is the same as described in this specification,

[0143] X 11 Can be C(R 11 ) or N, X12 Can be C(R 12 ) or N, X 13 Can be C(R 13 ) or N, X 14 Can be C(R 14 ) or N,

[0144] X 21 Can be C(R 21 ) or N, X 22 Can be C(R 22 ) or N, X 23 Can be C(R 23 ) or N, X 24 Can be C(R 24 ) or N,

[0145] X 31 Can be C(R 31 ) or N, X 32 Can be C(R 32 ) or N, X 33 Can be C(R 33 ) or N, X 34 Can be C(R 34 ) or N,

[0146] R 11 -R 14 Each independently and with respect to R 10 Same as described,

[0147] R 21 -R 24 Each independently and with respect to R 20 Same as described,

[0148] R 31 -R 34 Each independently and with respect to R 30 Same as described,

[0149] R 11 -R 14 Two or more of may be optionally linked to each other to form an unsubstituted or substituted group consisting of at least one R 10a Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups,

[0150] R 21 -R 24 Two or more of may be optionally linked to each other to form an unsubstituted or substituted group consisting of at least one R 10a Substituted C5-C 30The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups,

[0151] R 31 -R 34 Two or more of may be optionally linked to each other to form an unsubstituted or substituted group consisting of at least one R 10a Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 heterocyclic groups, and

[0152] R 10a About R 10 Same as described.

[0153] In an embodiment, R in Formula 11-1 11 -R 14 、R 21 -R 24 、R 31 -R 34 and R 41 -R 50 At least one of may be -Ge(Q1)(Q2)(Q3).

[0154] For example, R in Formula 11-1 31 -R 34 and R 41 -R 50 At least one of may be -Ge(Q1)(Q2)(Q3).

[0155] In an embodiment, R in Formula 11-1 11 -R 14 and R 21 -R 24 At least one of may be -Ge(Q1)(Q2)(Q3).

[0156] In an embodiment, "is not substituted or is replaced by at least one R 10a Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Examples of "heterocyclic group" include each of which is unsubstituted or substituted with at least one R 10a A substituted phenyl group, a naphthalene group, a cyclopentane group, a cyclopentadiene group, a cyclohexane group, a cycloheptane group, a bicyclo[2.2.1]heptane group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, or a benzosilole group. 10a About R10 Same as described. C5-C 30 Carbocyclic groups and C1-C 30 The heterocyclic groups are each the same as described in the present specification.

[0157] In an embodiment, the organometallic compound may be a compound represented by one of Formulas 12-1 to 12-7:

[0158] Formula 12-1

[0159]

[0160] Formula 12-2

[0161]

[0162] Formula 12-3

[0163]

[0164] Formula 12-4

[0165]

[0166] Formula 12-5

[0167]

[0168] Formula 12-6

[0169]

[0170] Formula 12-7

[0171]

[0172] Among them, in formulas 12-1 to 12-7,

[0173] M1, n1, n2, and R 41 -R 50 Same as described in this manual,

[0174] Y 21 Can be O, S, N (R 29A )、C(R 29A )(R 29B ), or Si(R 29A )(R 29B ),

[0175] R 11 -R 14 Each independently and with respect to R 10 Same as described,

[0176] R21 -R 28 、R 29A , and R 29B Each independently and with respect to R 20 Same as described, and

[0177] R 31 -R 34 Each independently and with respect to R 30 Same as described.

[0178] In an embodiment, in Formulas 12-1 to 12-7,

[0179] R 11 -R 14 Two or more of may be optionally linked to each other to form an unsubstituted or substituted group consisting of at least one R 10a Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups,

[0180] R 21 -R 28 、R 29A , and R 29B Two or more of may be optionally linked to each other to form an unsubstituted or substituted group consisting of at least one R 10a Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic groups, and

[0181] R 31 -R 34 Two or more of may be optionally linked to each other to form an unsubstituted or substituted group consisting of at least one R 10a Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 Heterocyclic group.

[0182] R 10a Same as described in this manual.

[0183] R 11 -R 14 、R 21 -R 28 、R 29A 、R 29B , and R 31 -R 34 Two or more adjacent groups therein may optionally be linked together to form a phenyl group or a naphthyl group.

[0184] In an embodiment, the number of R is b30 30 At least one of may be -Ge(Q1)(Q2)(Q3).

[0185] In an embodiment, R 41 -R 50 At least one of may be -Ge(Q1)(Q2)(Q3).

[0186] In an embodiment, the number of R is b10 10 , the number of R is b20 20 , and the number b30 of R 30 , and R 41 -R 50 At least one of which may be a substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3).

[0187] In an embodiment, the number of R is b10 10 , the number of R is b20 20 , and the number b30 of R 30 , and R 41 -R 50 At least one of the alkyl radicals may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, biphenyl, C1-C 20 Alkylphenyl, naphthyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3).

[0188] In an embodiment, R in Formula 11-1 or Formulas 12-1 to 12-7 31 -R 34 and R 41 -R 50 At least one of which may be a substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3).

[0189] In an embodiment, R in Formula 11-1 or Formulas 12-1 to 12-7 31 -R 34 and R 41 -R50 At least one of the alkyl radicals may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, biphenyl, C1-C 20 Alkylphenyl, naphthyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3).

[0190] In an embodiment, R in Formulas 3-1 to 3-40 31 -R 34 At least one of which may be a substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3).

[0191] In an embodiment, R in Formulas 3-1 to 3-40 31 -R 34 At least one of the alkyl radicals may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 Alkylphenyl, naphthyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3).

[0192] In an embodiment, the organometallic compound may include one germanyl group or two, three, or four germanyl groups. In other words, the organometallic compound may include one to four -Ge(Q1)(Q2)(Q3).

[0193] For example, the organometallic compound may include one or two germyl groups. In other words, the organometallic compound may include one or two -Ge(Q1)(Q2)(Q3).

[0194] In an embodiment, the organometallic compound may be one of Compounds 1 to 36:

[0195]

[0196]

[0197]

[0198] In an embodiment, the organometallic compound may be electrically neutral.

[0199] The organometallic compound represented by Formula 1 satisfies the structure of Formula 1, and Formula 1 includes at least one germyl group substituted into a bidentate ligand including, for example, a benzo[9,10]phenanthrene moiety. Due to this structure, the organometallic compound represented by Formula 1 has excellent luminescent properties and, by controlling the emission wavelength range, is suitable for use as a light-emitting material having high color purity.

[0200] In addition, the organometallic compound represented by Formula 1 has excellent electron mobility, and thus, an electronic device including the organometallic compound, for example, an organic light-emitting device including the organometallic compound, may exhibit low driving voltage, high efficiency, long lifespan, and reduced roll-off phenomenon.

[0201] In addition, the organometallic compound represented by Formula 1 has improved photochemical stability, and thus, an electronic device including the organometallic compound, for example, an organic light-emitting device including the organometallic compound, may exhibit high luminous efficiency, long lifetime, and high color purity.

[0202] The highest occupied molecular orbital (HOMO) energy level, lowest unoccupied molecular orbital (LUMO) energy level, energy gap, S1 energy level, and T1 energy level of some compounds of the organometallic compound represented by Formula 1 were evaluated using the Gaussian09 program with molecular structure optimization obtained by density functional theory (DFT) based on B3LYP, and the results are shown in Table 1.

[0203] Table 1

[0204]

[0205]

[0206] As confirmed in Table 1, the organometallic compound represented by Formula 1 has electrical characteristics suitable for use as a dopant for electronic devices such as organic light-emitting devices.

[0207] In an embodiment, the full width at half maximum (FWHM) of the emission peak of the emission spectrum or electroluminescence spectrum of the organometallic compound may be about 70 nm or less. For example, the FWHM of the emission peak of the emission spectrum or electroluminescence spectrum of the organometallic compound may be about 30 nm to about 65 nm, about 40 nm to about 63 nm, or about 45 nm to about 62 nm.

[0208] In an embodiment, the maximum emission wavelength (emission peak wavelength, λ) of the emission spectrum or the emission peak of the electroluminescence spectrum of the organometallic compound is 最大 ) may be from about 500 nm to about 600 nm.

[0209] The synthesis method of the organometallic compound represented by Formula 1 may be recognized by those of ordinary skill in the art by referring to the synthesis examples provided below.

[0210] The organometallic compound represented by Formula 1 is suitable for use in an organic layer of an organic light-emitting device, for example, as a dopant in an emissive layer of the organic layer. Therefore, another aspect provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer disposed between the first and second electrodes and comprising the emissive layer, wherein the organic layer comprises at least one organometallic compound represented by Formula 1.

[0211] As described above, the organic light-emitting device may have excellent characteristics in terms of driving voltage, current efficiency, power efficiency, external quantum efficiency, lifespan, and / or color purity due to the inclusion of an organic layer containing an organometallic compound represented by Formula 1. In addition, such an organic light-emitting device may have reduced roll-off and a relatively narrow electroluminescence (EL) spectrum emission peak FWHM.

[0212] The organometallic compound of Formula 1 can be used 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 emissive layer. In this regard, the organometallic compound can act as a dopant, and the emissive layer can further include a host (i.e., the amount of the organometallic compound represented by Formula 1 in the emissive layer is less than the amount of the host).

[0213] In an embodiment, the emission layer may emit green light. For example, the emission layer may emit green light having a maximum emission wavelength of about 500 nm to about 600 nm.

[0214] The expression “(the organic layer) includes at least one organometallic compound represented by Formula 1” used herein may include the case where “(the organic layer) includes the same organometallic compound represented by Formula 1” and the case where “(the organic layer) includes two or more different organometallic compounds represented by Formula 1”.

[0215] For example, the organic layer may include only Compound 1 as the organometallic compound. In this embodiment, Compound 1 may be included in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include Compound 1 and Compound 2 as the organometallic compound. In this regard, Compound 1 and Compound 2 may be present in the same layer (for example, Compound 1 and Compound 2 may all be present in the emission layer).

[0216] The first electrode may be an anode as a hole injection electrode, and the second electrode may be a cathode as an electron injection electrode; or the first electrode may be a cathode as an electron injection electrode, and the second electrode may be an anode as a hole injection electrode.

[0217] In an embodiment, in the organic light-emitting device, the first electrode is an anode, and the second electrode is a cathode, and the organic layer may further include a hole transport region located between the first electrode and the emission layer and an electron transport region located between the emission layer and the second electrode, and the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0218] The term "organic layer" used herein refers to a single layer or multiple layers located between the first electrode and the second electrode of the organic light-emitting device. In addition to organic compounds, the "organic layer" may also include an organic metal complex containing a metal.

[0219] Figure 1 FIG is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment. Figure 1 The structure of an organic light emitting device according to an embodiment of the present disclosure and a method of manufacturing the organic light emitting device according to an embodiment of the present disclosure are described. The organic light emitting device 10 includes a first electrode 11 , an organic layer 15 , and a second electrode 19 that are sequentially stacked.

[0220] A substrate may be further disposed below the first electrode 11 or above the second electrode 19. Any substrate used in organic light-emitting devices available in the art may be used as the substrate, and the substrate may 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.

[0221] 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 may be an anode. The material for forming the first electrode 11 may be selected from a material having a high work function to promote hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0222] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 11 is not limited thereto.

[0223] The organic layer 15 is located on the first electrode 11 .

[0224] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0225] The hole transport region may be between the first electrode 11 and the emission layer.

[0226] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.

[0227] The hole transport region may include only a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, wherein for each structure, the layers are sequentially stacked in the order stated starting from the first electrode 11.

[0228] When the hole transport region includes a hole injection layer (HIL), the HIL may be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, casting, and / or Langmuir-Blodgett (LB) deposition.

[0229] When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a ... -8 Torr - about 10 -3 Torr vacuum pressure, and about However, the deposition conditions are not limited thereto.

[0230] When the hole injection layer is formed using spin coating, the coating conditions may vary depending on the material used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer. For example, the coating speed may be about 2,000 rpm to about 5,000 rpm, and the temperature for heat treatment after coating to remove the solvent may be about 80°C to about 200°C. However, the coating conditions are not limited thereto.

[0231] 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.

[0232] The hole transport region may include at least one of 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-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by the following Formula 201, or a compound represented by the following Formula 202:

[0233]

[0234] Formula 201

[0235]

[0236] Formula 202

[0237]

[0238] Ar in Formula 201 101 and Ar 102 Can be independently:

[0239] Phenylene, pentalene, indenylene, naphthylene, phenylene, heptalene, acenaphthene, fluorenylene, phenanthrenyl, anthracenyl, fluoranthenylene, benzo[9,10]phenanthrenyl, pyrenylene, phenanthrenyl phenylene, tetraphenylene, Base, Asia phenylene, or pentacene; or

[0240] Phenylene, pentalenylene, indenylene, naphthylene, phenylene, phenylene, heptalene, acenaphthene, fluorenylene, phenanthrenyl, anthracenyl, fluoranthenylene, benzo[9,10]phenanthrenyl, pyrenylene, phenanthrenyl phenylene, tetraphenylene, Base, Asia phenylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10Cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or a combination thereof.

[0241] In Formula 201, xa and xb may each independently be an integer of 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.

[0242] R in Equations 201 and 202 101 -R 108 、R 111 -R 119 and R 121 -R 124 Can be independently:

[0243] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.) or C1-C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);

[0244] C1-C 10 Alkyl or C1-C 10 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, or a combination thereof;

[0245] phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl; or

[0246] Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl, each substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C1-C 10 Alkyl, C1-C 10 alkoxy, or a combination thereof, but the embodiments of the present disclosure are not limited thereto.

[0247] R in Formula 201 109 Can be:

[0248] phenyl, naphthyl, anthracenyl, or pyridyl; or

[0249] Phenyl, naphthyl, anthracenyl, or pyridyl, each substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, naphthyl, anthracenyl, pyridyl, or a combination thereof.

[0250] According to an embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A, but embodiments of the present disclosure are not limited thereto:

[0251] Formula 201A

[0252]

[0253] R in Formula 201A 101 、R 111 、R 112 , and R 109 This can be understood by reference to the description provided herein.

[0254] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include compounds HT1 to HT20 shown below, but are not limited thereto:

[0255]

[0256]

[0257] The thickness of the hole transport region may be about For example, about When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about For example, about and the thickness of the hole transport layer may be in the range of about For example, about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics may be obtained without a significant increase in driving voltage.

[0258] In addition to these materials, the hole transport region may further include a charge generating material for improving conductive properties. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region.

[0259] The charge generating material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a compound containing a cyano group, or a combination thereof, but embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant include quinone derivatives such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; and compounds containing a cyano group such as compounds HT-D1 or F12, but are not limited thereto.

[0260]

[0261] The hole transport region may include a buffer layer.

[0262] Furthermore, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of the formed organic light emitting device may be improved.

[0263] Meanwhile, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer can be selected from the materials for the hole transport region described above and the materials for the host described below. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer can be mCP described below.

[0264] Then, an emission layer (EML) may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied when forming the hole injection layer, although the deposition or coating conditions may vary depending on the material used to form the emission layer.

[0265] The emission layer may include a host and a dopant, and the dopant may include at least one organometallic compound represented by Formula 1.

[0266] The host may include TPBi, TBADN, ADN (also known as "DNA"), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, or a combination thereof:

[0267]

[0268] In one or more embodiments, the host may further include a compound represented by Formula 301:

[0269] Formula 301

[0270]

[0271] Ar in formula 301 111 and Ar 112 Can be independently:

[0272] Phenylene, naphthylene, phenanthrenyl, or pyrenylene; or

[0273] Phenylene, naphthylene, phenanthrenylene, or pyrenylene, each substituted with phenyl, naphthyl, anthracenyl, or a combination thereof.

[0274] Ar in formula 301 113 -Ar 116 Can be independently:

[0275] C1-C 10 alkyl, phenyl, naphthyl, phenanthrenyl, or pyrenyl; or

[0276] Phenyl, naphthyl, phenanthrenyl, or pyrenyl, each substituted with phenyl, naphthyl, anthracenyl, or a combination thereof.

[0277] g, h, i, and j in Formula 301 may each independently be an integer from 0 to 4, and may be, for example, 0, 1, or 2.

[0278] Ar in formula 301 113 and Ar 116 Can be independently:

[0279] C1-C1 substituted by phenyl, naphthyl, anthracenyl, or a combination thereof 10 alkyl;

[0280] phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl;

[0281] Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl, each substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, 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, C1-C 60 Alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, fluorenyl, or a combination thereof; or

[0282]

[0283] In one or more embodiments, the host may include a compound represented by Formula 302 below:

[0284] <Formula 302>

[0285]

[0286] Ar in formula 302 122 -Ar 125 Regarding Ar in Formula 301 113 Same as described in detail.

[0287] Ar in formula 302 126 and Ar 127 Can be independently C1-C 10 Alkyl (eg, methyl, ethyl, or propyl).

[0288] In formula 302, k and l can each independently be an integer from 0 to 4. For example, k and l can be 0, 1, or 2.

[0289] When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, the emission layer may emit white light due to the stacked structure including the red emission layer, the green emission layer, and / or the blue emission layer.

[0290] When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.

[0291] The thickness of the emission layer may be about For example, about When the thickness of the emission layer is within these ranges, excellent light emitting characteristics can be obtained without a significant increase in driving voltage.

[0292] An electron transport region may then be located on the emissive layer.

[0293] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0294] For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure, and the structure of the electron transport region is not limited thereto. The electron transport layer may have a multilayer structure or a single layer structure including two or more different materials.

[0295] By referring to the conditions for forming the hole injection layer, the conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region can be understood.

[0296] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, or BAlq, but embodiments of the present disclosure are not limited thereto.

[0297]

[0298] The thickness of the hole blocking layer may be about For example, about When the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking properties without a significant increase in driving voltage.

[0299] The electron transport layer may include at least one of BCP, Bphen, Alq3, BAlq, TAZ, or NTAZ.

[0300]

[0301] In one or more embodiments, the electron transport layer may include at least one of ET1 to ET25, but is not limited thereto:

[0302]

[0303]

[0304]

[0305] The thickness of the electron transport layer can be about For example, about When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a significant increase in driving voltage.

[0306] In addition, the electron transport layer may further include a material including a metal in addition to the materials described above.

[0307] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium quinolate, LiQ) or ET-D2:

[0308]

[0309] The electron transport region may include an electron injection layer (EIL) that facilitates the flow of electrons from the second electrode 19 thereinto.

[0310] The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or a combination thereof.

[0311] The thickness of the electron injection layer can be about For example, about When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a significant increase in driving voltage.

[0312] The second electrode 19 is located on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a metal, an alloy, a conductive compound, or a combination thereof having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as the material for forming the second electrode 19. In one or more embodiments, in order to manufacture a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0313] In the previous article, reference has been made to Figure 1 The organic light emitting device is described, but embodiments of the present disclosure are not limited thereto.

[0314] Another aspect provides a diagnostic composition comprising at least one organometallic compound represented by Formula 1.

[0315] The organometallic compound represented by Formula 1 provides high luminescence efficiency. Therefore, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.

[0316] The diagnostic compositions can be used in a variety of applications including diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0317] As used herein, the term "C1-C 60 "Alkyl" refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl. As used herein, the term "C1-C 60 "Alkylene" refers to a group having a C1-C 60 Alkyl is a divalent group of the same structure.

[0318] The term "C1-C 60 "Alkoxy" refers to a group consisting of -OA 101 (where A 101 C1-C 60 It is a monovalent group represented by an alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropoxy group.

[0319] As used herein, the term "C2-C 60"Alkenyl" refers to a C2-C 60 The term "C2-C4" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon double bond into the middle or terminal of an alkyl group, and examples thereof include vinyl, propenyl, and butenyl. 60 "Alkenylene" refers to a group having a C2-C 60 Alkenyl is a divalent group of the same structure.

[0320] As used herein, the term "C2-C 60 "Alkynyl" refers to a C2-C 60 The term "C1-C2" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon triple bond into the middle or terminal of an alkyl group, and examples thereof include ethynyl and propynyl. 60 "Alkynylidene" refers to a group having a C1-C 60 Alkynyl is a divalent group of the same structure.

[0321] As used herein, the term "C3-C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C 10 "Cycloalkylene" refers to a group having a C3-C 10 Cycloalkyl is a divalent group of the same structure.

[0322] As used herein, the term "C1-C 10 "Heterocycloalkyl" refers to a monovalent saturated cyclic group having at least one heteroatom selected from N, O, P, Si, S, Se, B, Te, or Ge as a ring atom and 1 to 10 carbon atoms, and non-limiting examples thereof include tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C1-C 10 "Heterocycloalkylene" refers to a 10 Heterocycloalkyl is a divalent group of the same structure.

[0323] As used herein, the term "C3-C 10 "Cycloalkenyl" refers to a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C 10 "Cycloalkenylene" refers to a group having a C3-C 10 Cycloalkenyl is a divalent group of the same structure.

[0324] As used herein, the term "C2-C 10"Heterocycloalkenyl" refers to a monovalent cyclic group having at least one heteroatom selected from N, O, P, Si, S, Se, B, Te, or Ge as a ring atom, 2 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. 10 Examples of heterocycloalkenyl are 2,3-dihydrofuryl and 2,3-dihydrothienyl. As used herein, the term "C2-C 10 "Heterocycloalkenylene" refers to a C2-C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0325] As used herein, the term "C6-C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term "C6-C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 60 Examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C6-C 60 Aryl and C6-C 60 When the arylene groups each include two or more rings, the rings may be fused to each other. 60 Alkaryl refers to a group consisting of at least one C1-C 60 Alkyl-substituted C6-C 60 Aryl.

[0326] As used herein, the term "C1-C 60 "Heteroaryl" refers to a monovalent group having a cyclic aromatic system having at least one heteroatom selected from N, O, P, Si, S, Se, B, Te, or Ge as a ring atom and 1 to 60 carbon atoms. As used herein, the term "C1-C 60 "Heteroarylene" refers to a divalent group having a cyclic aromatic system having at least one heteroatom selected from N, O, P, S, Se, B, Te, or Ge as a ring atom and 1 to 60 carbon atoms. 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 60 Heteroaryl and C6-C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other. 60 Alkylheteroaryl refers to a group consisting of at least one C1-C 60 Alkyl-substituted C1-C 60 Heteroaryl.

[0327] As used herein, the term "C6-C 60 "Aryloxy" means -OA 102 (where A 102 C6-C 60 aryl), and as used herein, the term "C6-C 60 "Arylthio" means -SA 103 (where A 103 C6-C 60 aryl).

[0328] The C1-C 60 Heteroaryloxy represents -OA 104 (where A 104 C1-C 60 heteroaryl), and C1-C 60 Heteroarylthio represents -SA 105 (where A 105 C1-C 60 heteroaryl).

[0329] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other, having only carbon atoms as ring atoms, and not having aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic fused polycyclic group include fluorenyl. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.

[0330] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" refers to a monovalent group (e.g., having 2 to 60 carbon atoms) having two or more rings fused to each other, having, in addition to carbon atoms, a heteroatom selected from N, O, P, Si, S, Se, B, Te, Ge, or a combination thereof as a ring-forming atom, and not having aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic fused heteropolycyclic group include carbazolyl. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.

[0331] As used herein, the term "C5-C 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring atoms. 30 The carbocyclic group may be a monocyclic group or a polycyclic group.

[0332] As used herein, the term "C1-C 30A "heterocyclic group" refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, Si, P, S, Se, B, Te, or Ge as a ring atom in addition to 1 to 30 carbon atoms. 30 The heterocyclic group may be a monocyclic group or a polycyclic group.

[0333] In this specification, TMS represents *-Si(CH 3 ) 3 , and TMG represents *-Ge(CH 3 ) 3 .

[0334] Substituted C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C2-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be:

[0335] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or a combination thereof;

[0336] C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60Alkoxy, or a combination thereof: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 ),-Ge(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 ),-P(=O)(Q 18 )(Q 19 ), or a combination thereof;

[0337] C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 a heteroarylthio group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or a combination thereof;

[0338] C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, or a combination thereof: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, 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, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 ),-Ge(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ),-P(=O)(Q 28 )(Q 29 ), or a combination thereof; or

[0339] -Si(Q 31 )(Q 32 )(Q 33 ),-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 ), or -P(=O)(Q 38 )(Q 39 ), or a combination thereof,

[0340] Among them, Q1-Q9, Q 11 -Q19 , Q 21 -Q 29 , and Q 31 -Q 39 Each of them can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0341] Hereinafter, compounds and organic light-emitting devices according to embodiments are described in detail with reference to Synthesis Examples and Examples. However, the organic light-emitting device is not limited thereto. The phrase "using 'B' instead of 'A'" used in describing Synthesis Examples means that the amount of 'A' used is the same as the amount of 'B' used in terms of molar equivalents.

[0342] Example

[0343] Synthesis Example 1: Synthesis of Compound 1

[0344]

[0345] (1) Synthesis of Compound 1A

[0346] 2-Phenyl-pyridine (5.0 g, 31.9 mmol) and iridium chloride trihydrate (IrCl3(H2O) n, n=3) (4.9 g, 14.2 mmol) was mixed with 120 mL of ethoxyethanol and 40 mL of deionized (DI) water, and then stirred for 24 hours while refluxing. The resulting mixture was cooled to room temperature. The resulting solid was isolated by filtration, washed thoroughly with water, methanol (MeOH), and hexane in the order stated, and then dried in a vacuum oven to obtain 7.9 g (89% yield) of compound 1A. The obtained compound 1A was used in the next reaction without additional purification.

[0347] (2) Synthesis of Compound 1B

[0348] Compound 1A (1.6g, 1.5mmol) is mixed with the methylene chloride (MC) of 45mL, then, silver trifluoromethanesulfonate (AgOTf) (0.8g, 3.1mmol) is added thereto after mixing with the methanol of 15mL.Afterwards, while blocking light with aluminium foil, mixture is at room temperature stirred 18 hours, then filtered through diatomite to remove gained solid, and filtrate is under reduced pressure concentrated to obtain solid (compound 1B).Compound 1B is used in next reaction when there is no other purification process.

[0349] (3) Synthesis of Compound 2A

[0350] Under nitrogen atmosphere, 4,4,5,5-tetramethyl-2-(benzo[9,10]phenanthrene-2-yl)-1,3,2-dioxaborolane (3.0 g, 8.4 mmol) and 2-chloro-4-isobutyl-5-(trimethylgermyl)pyridine (2.0 g, 7.0 mmol) were dissolved in 140 ml of tetrahydrofuran. Potassium carbonate (K2CO3) (2.2 g, 21.0 mmol) was then dissolved in 35 mL of DI water, and the resulting solution was added to the reaction mixture, and palladium catalyst (Pd(PPh3)4) (0.81 g, 0.70 mmol) was added thereto. The reaction mixture was then stirred while being refluxed at 100°C. After extraction, the obtained solid was subjected to column chromatography (eluent: MC (dichloromethane) and hexane) to obtain 4.0 g (91% yield) of 4-isobutyl-5-(trimethylgermyl)-2-(benzo[9,10]phenanthrene-2-yl)pyridine. The obtained compound was confirmed by HRMS (high resolution mass spectrometry) and HPLC (high performance liquid chromatography) analysis.

[0351] HRMS (MALDI): For C 30 H 31 Calculated value for GeN: m / z: 479.17, found: 480.21

[0352] (4) Synthesis of Compound 1

[0353] Compound 1B (1.5g, 2.1mmol) and compound 2A (1.1g, 2.3mmol) are mixed with 100mL of 2-ethoxyethanol and stirred for 24 hours while refluxing, and then the resultant is cooled. An extraction process is carried out on it with dichloromethane and water, and then the water layer is removed therefrom. The gained organic layer is treated with anhydrous magnesium sulfate, subsequently filtered and concentrated under reduced pressure. The obtained solid is subjected to column chromatography (eluent: dichloromethane (MC) and hexane) to obtain 0.7g (35% yield) of compound 1. The obtained compound is confirmed by HRMS and HPLC analysis.

[0354] HRMS (MALDI): For C 52 H 46 Calculated value of GeIrN3: m / z: 979.25, found: 980.81

[0355] Synthesis Example 2: Synthesis of Compound 2

[0356]

[0357] (1) Synthesis of compound 1C

[0358] 2.3 g (93% yield) of compound 1C (4-isopropyl-2-(7-isopropyldibenzo[b,d]furan-4-yl)pyridine) was obtained in the same manner as for the synthesis of compound 2A, except that (7-isopropyldibenzo[b,d]furan-4-yl)boronic acid (2.3 g, 9.0 mmol) was used instead of 4,4,5,5-tetramethyl-2-(benzo[9,10]phenanthrene-2-yl)-1,3,2-dioxaborolane, and 2-bromo-4-isopropylpyridine (1.5 g, 7.5 mmol) was used instead of 2-chloro-4-isobutyl-5-(trimethylgermyl)pyridine. The obtained compound was confirmed by HRMS and HPLC analysis.

[0359] HRMS (MALDI): For C 23 H 23 Calculated value of NO: m / z: 329.18, found: 330.44

[0360] (2) Synthesis of Compound 1D

[0361] 2.2 g (84% yield) of compound 1D was obtained in the same manner as for the synthesis of compound 1A, except that compound 1C (4-isopropyl-2-(7-isopropyldibenzo[b,d]furan-4-yl)pyridine) (2.0 g, 6.0 mmol) was used instead of 2-phenyl-pyridine. The obtained compound 1D was used in the next reaction without additional purification.

[0362] (3) Synthesis of Compound 1E

[0363] Compound 1E was obtained in the same manner as for the synthesis of Compound 1B, except that Compound 1D (1.4 g, 0.8 mmol) was used instead of Compound 1A. Compound 1E was used in the next reaction without additional purification.

[0364] (4) Synthesis of Compound 2

[0365] 0.73 g (35% yield) of compound 2 was obtained in the same manner as for the synthesis of compound 1, except that compound 1E (1.5 g, 1.4 mmol) was used instead of compound 1B, and compound 2A was used in an amount of 0.8 g (1.6 mmol). The obtained compound was confirmed by HRMS and HPLC analysis.

[0366] HRMS (MALDI): For C 76 H 74 Calculated value of GeIrN3O2: m / z: 1327.46, found: 1327.35

[0367] Synthesis Example 3: Synthesis of Compound 3

[0368]

[0369] (1) Synthesis of compound 3A

[0370] 1.1 g (91% yield) of compound 3A (2-isopropyl-11-(5-(trimethylgermyl)pyridin-2-yl)dibenzo[f,h]quinoline) was obtained in the same manner as for the synthesis of compound 2A, except that 2-isopropyl-11-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)dibenzo[f,h]quinoline (1.1 g, 2.9 mmol) and 2-chloro-5-(trimethylgermyl)pyridine (0.6 g, 2.6 mmol) were used instead of 4,4,5,5-tetramethyl-2-(benzo[9,10]phenanthrene-2-yl)-1,3,2-dioxaborolane and 2-chloro-4-isobutyl-5-(trimethylgermyl)pyridine, respectively. The obtained compound was confirmed by HRMS and HPLC analysis.

[0371] HRMS (MALDI): For C 28 H 28 Calculated value of GeN2: m / z: 466.15, measured value: 467.28

[0372] (2) Synthesis of compound 3

[0373] 0.70 g (39% yield) of compound 3 was obtained in the same manner as for the synthesis of compound 1, except that compound 3A (0.9 g, 1.9 mmol) was used instead of compound 2A, and compound 1B was used in an amount of 1.2 g (1.7 mmol). The obtained compound was confirmed by HRMS and HPLC analysis.

[0374] HRMS (MALDI): For C 50 H 43 Calculated value of GeIrN4: m / z: 964.77, found: 965.31

[0375] Example 1

[0376] An ITO (anode) patterned glass substrate was cut into a size of 50 mm×50 mm×0.5 mm, ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The resulting glass substrate was loaded onto a vacuum deposition apparatus.

[0377] Compounds HT3 and F12 (p-dopant) were vacuum co-deposited on the anode at a weight ratio of 98:2 to form a A hole injection layer having a thickness of 1000 nm was formed, and compound HT3 was vacuum-deposited on the hole injection layer to form a hole injection layer having a thickness of 1000 nm. The hole transport layer has a thickness of .

[0378] Then, GH3 (host) and compound 1 (dopant) were co-deposited on the hole transport layer at a weight ratio of 92:8 to form a The thickness of the emission layer.

[0379] Then, compound ET3 and LiQ (n-dopant) were co-deposited on the emission layer in a volume ratio of 50:50 to form a An electron transport layer having a thickness of , LiQ is vacuum deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Al is vacuum deposited on the electron injection layer to form A cathode with a thickness of , thereby completing the manufacture of the organic light-emitting device.

[0380]

[0381] Examples 2-3 and Comparative Examples 1-3

[0382] Organic light-emitting devices were manufactured in the same manner as in Example 1, except that the compounds shown in Table 2 were each used as a dopant instead of Compound 1 when forming the emission layer.

[0383] The driving voltage, external quantum efficiency, maximum emission wavelength (λ) of the organic light emitting devices manufactured according to Examples 1-3 and Comparative Examples 1-3 were evaluated. 最大 ), FWHM, and lifespan (T 97 The results are shown in Table 2. A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1,000A) were used as devices for evaluation, and the lifespan (T 97 ) (at 18,000 nits), and the results are expressed as relative values.

[0384] Table 2

[0385]

[0386]

[0387] Referring to Table 2, it can be seen that the organic light-emitting devices of Examples 1-3 have low driving voltages, narrow FWHMs, and excellent characteristics in terms of external quantum efficiency and lifetime. Furthermore, it can be seen that, compared with the organic light-emitting devices of Comparative Examples 1-3, the organic light-emitting devices of Examples 1-3 have lower driving voltages, similar or narrower FWHMs, higher external quantum efficiency, and longer lifetimes.

[0388] The organometallic compound has excellent electrical properties and thermal stability. The organometallic compound has a high glass transition temperature, which prevents crystallization and improves electron mobility. Therefore, electronic devices using the organometallic compound, such as organic light-emitting devices using the organometallic compound, have low driving voltage, high efficiency, long life, reduced roll-off ratio, and a relatively narrow EL spectrum emission peak FWHM.

[0389] Therefore, due to the use of the organometallic compound, a high-quality organic light-emitting device can be realized. Such an organometallic compound has excellent phosphorescent emission characteristics and, therefore, when used, can provide a diagnostic composition with high diagnostic efficiency.

[0390] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects in each embodiment should typically be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the spirit and scope as defined by the appended claims.

Claims

1. An organometallic compound represented by Formula 12-1 or 12-2: Formula 12-1 Formula 12-2 in, In formulas 12-1 and 12-2, M1 is Ir, n1 is 1 or 2, n2 is 1 or 2, and The sum of n1 and n2 is 3, Y 21 is O or S, R 32 is -Ge(Q1)(Q2)(Q3), wherein Q1-Q3 are each independently: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, or tert-pentyl; or n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, or tert-pentyl, each substituted with deuterium, C1-C 10 Alkyl, or a combination thereof, R 33 for: C1-C 20 alkyl; or C1-C substituted as follows 20 Alkyl: deuterium, -CD3, -CD2H, -CDH2, C1-C 10 alkyl, or a combination thereof, and R 11 -R 14 、R 21 -R 28 、R 31 、R 34 , and R 41 -R 50 Each independently is: Hydrogen, deuterium, C1-C 20 Alkyl, or C1-C 20 alkoxy; or C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -CD3, -CD2H, -CDH2, C1-C 10 alkyl, or a combination thereof.

2. The organometallic compound according to claim 1, wherein R 11 -R 14 、R 21 -R 28 、R 31 、R 34 , and R 41 -R 50 Each independently is: Hydrogen, deuterium, C1-C 20 Alkyl, or C1-C 20 alkoxy; -CD3, -CD2H, or -CDH2; or C1-C 20 Alkyl or C1-C 20 Alkoxy: -CD3, -CD2H, -CDH2, C1-C 10 alkyl, or a combination thereof.

3. The organometallic compound according to claim 1, wherein R 32 is a group represented by one of formulae 9-41 and 9-43, R 33 is a group represented by one of formulae 9-1 to 9-39 and 9-44 to 9-61, and R 11 -R 14 、R 21 -R 28 、R 31 、R 34 , and R 41 -R 50 Each independently is: hydrogen, deuterium, -CD3, -CD2H, or -CDH2; or A group represented by one of formulae 9-1 to 9-39 and 9-44 to 9-61: * in Formulae 9-1 to 9-39, 9-41, and 9-43 to 9-61 represents a binding site with an adjacent atom.

4. The organometallic compound according to claim 1, wherein R 11 -R 14 Each is independently deuterium, -CD3, -CD2H, -CDH2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, or 3-methyl-2-butyl.

5. The organometallic compound according to claim 1, wherein R 21 -R 24 Each is independently deuterium, -CD3, -CD2H, -CDH2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, or 3-methyl-2-butyl.

6. The organometallic compound according to claim 1, wherein R 31 and R 34 are each independently deuterium, -CD3, -CD2H, -CDH2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, or 3-methyl-2-butyl, and R 33 is -CD3, -CD2H, -CDH2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, or 3-methyl-2-butyl.

7. The organometallic compound according to claim 1, wherein the organometallic compound is one of the following compounds: 。 8. Organic light-emitting devices, including: a first electrode; a second electrode; as well as an organic layer located between the first electrode and the second electrode and including an emission layer, The organic layer comprises the organometallic compound according to any one of claims 1 to 7. 9 . The organic light emitting device of claim 8 , wherein the organometallic compound is included in the emission layer. 10 . The organic light emitting device of claim 9 , wherein the emission layer further comprises a host, and an amount of the host is greater than an amount of the organometallic compound. 11 . The organic light emitting device of claim 9 , wherein the emission layer emits green light having a maximum emission wavelength of 500 nm to 600 nm.

12. The organic light emitting device according to claim 9, wherein The first electrode is an anode, The second electrode is a cathode, The organic layer further includes a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive layer and the second electrode, wherein The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

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