ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING ORGANOMETALLIC COMPOUND, AND ELECTRONIC APPARATUS INCLUDING ORGANIC LIGHT-EMITTING DEVICE

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority under 35 U.S.C. § 119 to Korean Patent Application Nos. 10-2020-0045374, filed on Apr. 14, 2020, and 10-2021-0046891, filed on Apr. 12, 2021, in the Korean Intellectual Property Office, the contents of which are incorporated by reference herein in their entirety.

BACKGROUND
1. Field

The present disclosure relates to an organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic apparatus including the organic light-emitting device.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emissive devices which produce full-color images. In addition, OLEDs have wide viewing angles and exhibit excellent driving voltage and response speed characteristics.

OLEDs include an anode, a cathode, and an organic layer between the anode and the cathode and including an emission layer. A hole transport region may be between the anode and the emission layer, and an electron transport region may be between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. The excitons may transit from an excited state to a ground state, thus generating light.

SUMMARY

Provided are an organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic apparatus including the organic light-emitting device.

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.

According to an aspect of an embodiment, an organometallic compound represented by Formula 1-1 is provided.

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In Formula 1-1,

M is a transition metal,

X₁is O, S, or N(R″′),

a bond between X₁and M is a covalent bond,

X₂to X₄and Y₁are each independently C or N,

one bond of a bond between X₂and M, a bond between X₃and M, and a bond between X₄and M is a covalent bond, while the remaining bonds are each be a coordinate bond,

X₅₁is O, S, N-[(L₇)_b7-(R₇)_c7], C(R₇)(R₈), Si(R₇)(R₈), Ge(R₇)(R₈), or C(═O),

Z₁₁is N or C-[(L₁₁)_b11-(T₁₁)_c11], Z₁₂is N or C-[(L₁₂)_b12-(T₁₂)_c12], Z₁₃is N or C-[(L₁₃)_b13-(T₁₃)_c13], and Z₁₄is N or C-[(L₁₄)_b14-(T₁₄)_c14],

Z₂₁is N or C-[(L₂₁)_b21-(T₂₁)_c21], Z₂₂is N or C-[(L₂₂)_b22-(T₂₂)_c22], and Z₂₃is N or C-[(L₂₃)_b23-(T₂₃)_c23],

Z₃₁is N or C-[(L₃₁)_b31-(T₃₁)_c31], Z₃₂is N or C-[(L₃₂)_b32-(T₃₂)_c32], and Z₃₃is N or C-[(L₃₃)_b33-(T₃₃)_c33],

Z₄₁is N or C-[(L₄₁)_b41-(T₄₁)_c41], Z₄₂is N or C-[(L₄₂)_b42-(T₄₂)_c42], Z₄₃is N or C-[(L₄₃)_b43-(T₄₃)_c43], and Z₄₄is N or C-[(L₄₄)_b44-(T₄₄)_c44],

L₇, L₁₁to L₁₄, L₂₁to L₂₃, L₃₁to L₃₃and L₄₁to L₄₄are each independently a single bond, a C₁-C₁₀alkylene group unsubstituted or substituted with at least one R_10a, a C₅-C₃₀carbocyclic group unsubstituted or substituted with at least one R_10a, or a C₁-C₃₀heterocyclic group unsubstituted or substituted with at least one R_10a,

b7, b11 to b14, b21 to b23, b31 to b33 and b41 to b44 are each independently 1, 2, 3, 4, or 5,

R″′, R₇, R₈, T₁₁to T₁₄, T₂₁to T₂₃, T₃₁to T₃₃and T₄₁to T₄₄are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —Ge(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), —P(═O)(Q₈)(Q₉), or —P(Q₈)(Q₉),

c7, c11 to c14, c21 to c23, c31 to c33 and c41 to c44 are each independently 1, 2, 3, 4, or 5,

wherein, the organometallic compound represented by Formula 1-1 satisfies:

1) one of Condition 11, Condition 12 and Condition 13,

2) Condition 11 and Condition 13, or

3) Condition 12 and Condition 13,

Z₄₂in Formula 1-1 is C-[(L₄₂)_b42-(T₄₂)_c42], Condition 11

T₄₂is a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, or a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, and

c42 is 1,

Z₄₂in Formula 1-1 is C-[(L₄₂)_b42-(T₄₂)_c42], Condition 12

T₄₂is a group represented by Formula 41, and

c42 is 1,

*—C(Q₄₁)(Q₄₂)(Q₄₃) Formula 41

wherein in Formula 41,

Q₄₁to Q₄₃are each independently deuterium, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

at least one of Q₄₁to Q₄₃are each independently a substituted or unsubstituted C₂-C₆₀alkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, or a substituted or unsubstituted C₆-C₆₀aryl group, and

* indicates a binding site to an adjacent atom,

X₅₁in Formula 1-1 is N-[(L₇)_b7-(R₇)_c7], Condition 13

L₇is a benzene group, or a naphthalene group, each unsubstituted or substituted with at least one R_10a,

R₇is a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, or a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, and

c7 is 1,

each of i) at least two of T₁₁to T₁₄, ii) at least two of T₂₁to T₂₃, iii) at least two of T₃₁to T₃₃, iv) at least two of T₄₁to T₄₄and v) at least two of T₁₁to T₁₄, T₂₁to T₂₃, T₃₁to T₃₃, and T₄₁to T₄₄are optionally bound to each other to form a C₅-C₃₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₃₀heterocyclic group unsubstituted or substituted with at least one R_10a,

R_10amay be understood by referring to the description of T₁₁provided herein,

a substituent of the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is

deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, or a C₁-C₆₀alkoxy group,

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, or a C₁-C₆₀alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), —Ge(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉), —P(Q₁₈)(Q₁₉), or any combination thereof,

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —Ge(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), —P(Q₂₈)(Q₂₉), or any combination thereof,

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —Ge(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), —P(═O)(Q₃₈)(Q₃₉), or —P(Q₃₈)(Q₃₉), or

any combination thereof,

wherein Q₁to Q₉, Q₁₁to Q₁₉, Q₂₁to Q₂₉, and Q₃₁to Q₃₉are independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group unsubstituted or substituted with deuterium, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or any combination thereof, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group unsubstituted or substituted with deuterium, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or any combination thereof, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.

According to an aspect of another embodiment, an organic light-emitting device may include a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer and at least one of the organometallic compound.

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.

According to an aspect of another embodiment, an electronic apparatus may include the organic light-emitting device.

BRIEF DESCRIPTION OF THE DRAWING

The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which

The FIGURE is a schematic cross-sectional view of an organic light-emitting device according to an exemplary embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

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

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 sections, these elements, components, regions, layers and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section Thus, “a first element,” “component,” “region,” “layer” or “section” discussed below could be termed a second element, component, region, layer or section without departing from the teachings herein.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, “a,” “an,” “the,” and “at least one” do not denote a limitation of quantity, and are intended to cover both the singular and 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.

“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 “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.

Furthermore, relative terms, such as “lower” or “bottom” and “upper” or “top,” may be used herein to describe one element's relationship to another element as illustrated in the Figures. It will be understood that relative terms are intended to encompass different orientations of the device in addition to the orientation depicted in the Figures For example, if the device in one of the figures is turned over, elements described as being on the “lower” side of other elements would then be oriented on “upper” sides of the other elements. The exemplary term “lower,” can therefore, encompasses both an orientation of “lower” and “upper,” depending on the particular orientation of the figure Similarly, if the device in one of the figures is turned over, elements described as “below” or “beneath” other elements would then be oriented “above” the other elements. The exemplary terms “below” or “beneath” can, therefore, encompass both an orientation of above and below.

“About” or “approximately” as used herein 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, considering the measurement in question and the error associated with 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 ±30%, 20%, 10% or 5% of the stated value.

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 that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.

An organometallic compound may be represented by Formula 1-1:

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wherein Formula 1-1 may be understood by referring to the description.

In an embodiment, the organometallic compound may have ΔST in a range of about 0.1 eV to about 0.2 eV.

In an embodiment, the organometallic compound may have a horizontal orientation ratio of about 85% or greater.

ΔST indicates an energy gap (an absolute value) between a singlet (S₁) energy level and a triplet (T₁) energy level of the organometallic compound represented by Formula 1-1. The singlet (S₁) energy level and the triplet (T₁) energy level of the organometallic compound may be calculated using a density functional theory (DFT). A method of measuring the singlet (S₁) energy level and the triplet (T₁) energy level of the organometallic compound may be understood with reference to Evaluation Example 1.

In an embodiment, the organometallic compound may have ΔST in a range of about 0.13 eV to about 0.2 eV, about 0.15 eV to about 0.2 eV or about 0.176 eV to about 0.2 eV.

In one or more embodiments, the organometallic compound may have ΔST in a range of about 0.10 eV to about 0.17 eV, about 0.12 eV to about 0.17 eV, or about 0.125 eV to about 0.16 eV.

In one or more embodiments, the organometallic compound may have a horizontal orientation ratio in a range of about 85% to about 95% or about 87% to about 95%.

In one or more embodiments, the organometallic compound may have a horizontal orientation ratio in a range of about 85% to about 100%, about 87% to about 97%, or about 88% to about 95%.

The horizontal orientation ratio of the organometallic compound, as used herein, may be a horizontal orientation ratio of a transition dipole moment of the organometallic compound. The term “horizontal orientation ratio of a transition dipole moment”, as used herein, refers to, in a film including the organometallic compound, a ratio of the organometallic compound having a transition dipole moment which is horizontal with respect to the film, relative to the total organometallic compound included in the film. A horizontal orientation ratio may be measured by preparing a film including a predetermined matrix compound (e.g., mCP) and the organometallic compound and measuring a horizontal orientation ratio of the film. For example, a method of measuring a horizontal orientation ratio of the organometallic compound may be understood by referring to Evaluation Example 2.

Since the organometallic compound has a high horizontal orientation ratio of a transition dipole moment as such, namely, a greatly oriented transition dipole moment (i.e., a large optical orientation in a horizontal direction), when the film includes the organometallic compound, it may be possible for the organometallic compound to emit a large electric field in a vertical direction with respect to the film. Since light emitted by this mechanism may pass to the outside with high efficiency (i.e., efficiency of light emitted from the organometallic compound passing to the outside in a device (e.g., an organic light-emitting device) including a film (e.g., an emission layer described herein) including the organometallic compound), an electronic device, e.g., an organic light-emitting device, employing the organometallic compound, may have excellent luminous efficiency.

In one or more embodiments, the organometallic compound may have a sublimation temperature in a range of about 200° C. to about 350° C., about 200° C. to about 340° C., or about 200° C. to about 300° C. The organometallic compound may have a molecular weight of 1,200 or less or 1100 or less. As the organometallic compound has a sublimation temperature and/or a molecular weight as described above, when forming a thin film including the organometallic compound, decomposition of the organometallic compound may be substantially prevented, thus forming a thin film showing excellent performance.

wherein, in Formula 1-1, M may be a transition metal.

For example, M may be cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au).

In an embodiment, M may be Pt, Pd, or Au.

In Formula 1-1, X₁may be O, S, or N(R″′), and a bond between X₁and M may be a covalent bond. R″′ may be understood by referring to the description of R″′ provided herein.

In some embodiments, X₁may be O or S.

In an embodiment, X₁may be O.

In Formula 1-1, X₂to X₄and Y₁may each independently be C or N.

For example, X₂and X₄may each be N, and Y₁and X₃may each be C.

In Formula 1-1, one bond of a bond between X₂and M, a bond between X₃and M, and a bond between X₄and M may be a covalent bond, while the remaining bonds may each be a coordinate bond. The organometallic compound represented by Formula 1-1 may be electrically neutral.

In some embodiments, a bond between X₂and M and a bond between X₄and M may each be a coordinate bond, and a bond between X₃and M may be a covalent bond.

X₅₁in Formula 1-1 may be O, S, N-[(L₇)_b7-(R₇)_c7], C(R₇)(R₈), Si(R₇)(R₈), Ge(R₇)(R₈), or C(═O). Each of R₇, b7, R₈and b8 may be understood by referring to the description provided herein. R₇and R₈may optionally be bound to each other via a first linking group to form a C₅-C₃₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₃₀heterocyclic group unsubstituted or substituted with at least one R_10a.

In an embodiment, X₅₁in Formula 1-1 may be O, S, or N-[(L₇)_b7-(R₇)_c7].

In an embodiment, X₅₁in Formula 1-1 may be N-[(L₇)_b7-(R₇)_c7].

In Formula 1-1,

Z₁₁may be N or C-[(L₁₁)_b11-(T₁₁)_c11], Z₁₂may be N or C-[(L₁₂)_b12-(T₁₂)_c12], Z₁₃may be N or C-[(L₁₃)_b13-(T₁₃)_c13], and Z₁₄may be N or C-[(L₁₄)_b14-(T₁₄)_c14],

Z₂₁may be N or C-[(L₂₁)_b21-(T₂₁)_c21], Z₂₂may be N or C-[(L₂₂)_b22-(T₂₂)_c22], and Z₂₃may be N or C-[(L₂₃)_b23-(T₂₃)_c23],

Z₃₁may be N or C-[(L₃₁)_b31-(T₃₁)_c31], Z₃₂may be N or C-[(L₃₂)_b32-(T₃₂)_c32], and Z₃₃may be N or C-[(L₃₃)_b33-(T₃₃)_c33], and

Z₄₁may be N or C-[(L₄₁)_b41-(T₄₁)_c41], Z₄₂may be N or C-[(L₄₂)_b42-(T₄₂)_c42], Z₄₃may be N or C-[(L₄₃)_b43-(T₄₃)_c43], and Z₄₄may be N or C-[(L₄₄)_b44-(T₄₄)_c44].

In an embodiment, none of Z₁₁to Z₁₄, none of Z₂₁to Z₂₃, none of Z₃₁to Z₃₃and none of Z₄₁to Z₄₄may be N.

In Formula 1-1, L₇, L₁₁to L₁₄, L₂₁to L₂₃, L₃₁to L₃₃and L₄₁to L₄₄may each independently be a single bond, a C₁-C₁₀alkylene group unsubstituted or substituted with at least one R_10a, a C₅-C₃₀carbocyclic group unsubstituted or substituted with at least one R_10a, or a C₁-C₃₀heterocyclic group unsubstituted or substituted with at least one R_10a.

For example, in Formula 1-1, L₇, L₁₁to L₁₄, L₂₁to L₂₃, L₃₁to L₃₃and L₄₁to L₄₄may each independently be:

a single bond; or

a methylene group, an ethylene group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, an adamantane group, norbornane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole 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, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, or a benzothiadiazole group, each unsubstituted or substituted with at least one R_10a.

In some embodiments, in Formula 1-1, L₇, L₁₁to L₁₄, L₂₁to L₂₃, L₃₁to L₃₃and L₄₁to L₄₄may each independently be:

a single bond; or

a methylene group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, an adamantane group, a norbornane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a benzene group, or a naphthalene group, each unsubstituted or substituted with at least one R_10a.

In Formula 1-1, b7, b11 to b14, b21 to b23, b31 to b33 and b41 to b44 may respectively indicate the number of L₇, L₁₁to L₁₄, L₂₁to L₂₃, L₃₁to L₃₃and L₄₁to L₄₄, and b7, b11 to b14, b21 to b23, b31 to b33 and b41 to b44 may each independently be 1, 2, 3, 4, or 5. For example, in Formula 1-1, b7, b11 to b14, b21 to b23, b31 to b33 and b41 to b44 may each independently be 1, 2, or 3.

In Formula 1-1, R″′, R₇, R₈, T₁₁to T₁₄, T₂₁to T₂₃, T₃₁to T₃₃and T₄₁to T₄₄may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —Ge(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), —P(═O)(Q₈)(Q), or —P(Q₈)(Q). Q₁to Q₉may respectively be understood by referring to the descriptions of Q₁to Q₃provided herein.

For example, in Formula 1-1, R″′, R₇, R₈, T₁₁to T₁₄, T₂₁to T₂₃, T₃₁to T₃₃and T₄₁to T₄₄may each independently be:

a C₂-C₁₀alkyl group or a C₂-C₂₀alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C₁-C₂₀alkyl)cyclopentyl group, a (C₁-C₂₀alkyl)cyclohexyl group, a (C₁-C₂₀alkyl)cycloheptyl group, a (C₁-C₂₀alkyl)cyclooctyl group, a (C₁-C₂₀alkyl)adamantanyl group, a (C₁-C₂₀alkyl)norbornanyl group, a (C₁-C₂₀alkyl)norbornenyl group, a (C₁-C₂₀alkyl)cyclopentenyl group, a (C₁-C₂₀alkyl)cyclohexenyl group, a (C₁-C₂₀alkyl)cycloheptenyl group, a (C₁-C₂₀alkyl)bicyclo[1.1.1]pentyl group, a (C₁-C₂₀alkyl)bicyclo[2.1.1]hexyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof; or

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group or an azadibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C₁-C₂₀alkyl)cyclopentyl group, a (C₁-C₂₀alkyl)cyclohexyl group, a (C₁-C₂₀alkyl)cycloheptyl group, a (C₁-C₂₀alkyl)cyclooctyl group, a (C₁-C₂₀alkyl)adamantanyl group, a (C₁-C₂₀alkyl)norbornanyl group, a (C₁-C₂₀alkyl)norbornenyl group, a (C₁-C₂₀alkyl)cyclopentenyl group, a (C₁-C₂₀alkyl)cyclohexenyl group, a (C₁-C₂₀alkyl)cycloheptenyl group, a (C₁-C₂₀alkyl)bicyclo[1.1.1]pentyl group, a (C₁-C₂₀alkyl)bicyclo[2.1.1]hexyl group, a (C₁-C₂₀alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C₁-C₂₀alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or any combination thereof; or

—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —Ge(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), —P(═O)(Q₈)(Q₉), or —P(Q₈)(Q₈),

wherein Q₁to Q₉may each independently be:

—CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, or —CD₂CDH₂;

an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C₁-C₁₀alkyl group, a phenyl group, or any combination thereof.

In some embodiments, in Formula 1-1, R″′, R₇, R₈, T₁₁to T₁₄, T₂₁to T₂₃, T₃₁to T₃₃and T₄₁to T₄₄may each independently be:

hydrogen, deuterium, —F, or a cyano group; or

a C₁-C₂₀alkyl group, a C₃-C₁₀cycloalkyl group, a phenyl group, a biphenyl group or a naphtyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₂₀alkyl group, a deuterated C₁-C₂₀alkyl group, a fluorinated C₁-C₂₀alkyl group, a C₃-C₁₀cycloalkyl group, a (C₁-C₂₀alkyl)C₃-C₁₀cycloalkyl group, a deuterated C₃-C₁₀cycloalkyl group, a fluorinated C₃-C₁₀cycloalkyl group, or any combination thereof.

In Formula 1-1, c7, c11 to c14, c21 to c23, c31 to c33 and c41 to c44 may respectively indicate the number of R₇, T₁₁to T₁₄, T₂₁to T₂₃, T₃₁to T₃₃and T₄₁to T₄₄, and c7, c11 to c14, c21 to c23, c31 to c33 and c41 to c44 may each independently be 1, 2, 3, 4, or 5. For example, c7, c11 to c14, c21 to c23, c31 to c33 and c41 to c44 may each independently be 1 or 2.

The organometallic compound represented by Formula 1-1 may satisfy:

1) one of Condition 11, Condition 12 and Condition 13,

2) Condition 11 and Condition 13, or

3) Condition 12 and Condition 13.

Z₄₂in Formula 1-1 is C-[(L₄₂)_b42-(T₄₂)_c42], Condition 11

c42 is 1.

Z₄₂in Formula 1-1 is C-[(L₄₂)_b42-(T₄₂)_c42], Condition 12

T₄₂is a group represented by Formula 41, and

c42 is 1:

*—C(Q₄₁)(Q₄₂)(Q₄₃) Formula 41

wherein in Formula 41,

* indicates a binding site to an adjacent atom.

X₅₁in Formula 1-1 is N-[(L₇)_b7-(R₇)_c7], Condition 13

L₇is a benzene group, or a naphthalene group, each unsubstituted or substituted with at least one R_10a,

c7 is 1.

In some embodiments, the organometallic compound represented by Formula 1-1 may satisfy Condition 11 or Condition 12.

In some embodiments, the organometallic compound represented by Formula 1-1 may satisfy Condition 11 and L₄₂may be a benzene group, or a naphthalene group, each unsubstituted or substituted with at least one R_10a.

In some embodiments, the organometallic compound represented by Formula 1-1 may satisfy Condition 12 and L₄₂may be a benzene group, or a naphthalene group, each unsubstituted or substituted with at least one R_10a.

In some embodiments, the organometallic compound represented by Formula 1-1 may satisfy Condition 11 or Condition 13, and T₄₂and R₇may each independently be a C₃-C₁₀cycloalkyl group unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₂₀alkyl group, a deuterated C₁-C₂₀alkyl group, a fluorinated C₁-C₂₀alkyl group, a phenyl group, a (C₁-C₂₀alkyl) phenyl group, a deuterated phenyl group, or a fluorinated phenyl group.

In some embodiments, the organometallic compound represented by Formula 1-1 may satisfy Condition 12, and Q₄₁to Q₄₃in Formula 41 may each independently be: deuterium; or

a C₁-C₂₀alkyl group, a C₃-C₁₀cycloalkyl group, a phenyl group, a biphenyl group or a naphtyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₂₀alkyl group, a deuterated C₁-C₂₀alkyl group, a fluorinated C₁-C₂₀alkyl group, a C₃-C₁₀cycloalkyl group, a (C₁-C₂₀alkyl) C₃-C₁₀cycloalkyl group, a deuterated C₃-C₁₀cycloalkyl group, a fluorinated C₃-C₁₀cycloalkyl group, or any combination thereof.

In some embodiments, the organometallic compound represented by Formula 1-1 may satisfy Condition 12 and at least one of Q₄₁to Q₄₃in Formula 41 may each independently be a C₂-C₂₀alkyl group, a C₃-C₁₀cycloalkyl group, a phenyl group, a biphenyl group or a naphtyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₂₀alkyl group, a deuterated C₁-C₂₀alkyl group, a fluorinated C₁-C₂₀alkyl group, a C₃-C₁₀cycloalkyl group, a (C₁-C₂₀alkyl) C₃-C₁₀cycloalkyl group, a deuterated C₃-C₁₀cycloalkyl group, or a fluorinated C₃-C₁₀cycloalkyl group.

Each of i) at least two of T₁₁to T₁₄, ii) at least two of T₂₁to T₂₃, iii) at least two of T₃₁to T₃₃, iv) at least two of T₄₁to T₄₄and v) at least two of T₁₁to T₁₄, T₂₁to T₂₃, T₃₁to T₃₃, and T₄₁to T₄₄may optionally be bound to each other to form a C₅-C₃₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₃₀heterocyclic group unsubstituted or substituted with at least one R_10a.

R_10amay be understood by referring to the description of T₁₁provided herein, and

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₀aryl group, a C₆-C₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —Ge(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), —P(Q₂₈)(Q₂₉), or any combination thereof;

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —Ge(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), —P(═O)(Q₃₈)(Q₃₉), or —P(Q₃₈)(Q₃₉); or

any combination thereof,

wherein Q₁to Q₉, Q₁₁to Q₁₉, Q₂₁to Q₂₉, and Q₃₁to Q₃₉may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C₁-C₆₀alkyl group unsubstituted or substituted with deuterium, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or any combination thereof; a C₂-C₆₀alkenyl group; a C₂-C₆₀alkynyl group; a C₁-C₆₀alkoxy group; a C₃-C₁₀cycloalkyl group; a C₁-C₁₀heterocycloalkyl group; a C₃-C₁₀cycloalkenyl group; a C₁-C₁₀heterocycloalkenyl group; a C₆-C₀aryl group unsubstituted or substituted with deuterium, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or any combination thereof; a C₆-C₆₀aryloxy group; a C₆-C₆₀arylthio group; a C₁-C₆₀heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

In an embodiment, in Formula 1-1, X₅₁may be N-[(L₇)_b7-(R₇)_c7], and the group represented by *-[(L₇)_b7-(R₇)_c7] may be a group represented by Formula N51:

embedded image

wherein, in Formula N51, ring CY₅₁may be a C₅-C₃₀carbocyclic group or a C₁-C₃₀heterocyclic group. For example, ring CY₅₁may be a benzene group or a naphthalene group.

In Formula N51, L₅₁, b51, R₅₁, and c51 may respectively be understood by referring to the descriptions of L₇, b7, R₇, and c7 provided herein, and R₅₂and c52 may respectively be understood by referring to the descriptions of R₇and c7 provided herein.

In Formula N51, A₅₁may be a C₁-C₆₀alkyl group unsubstituted or substituted with a C₃-C₁₀cycloalkyl group. For example, A₅₁may be a C₁-C₂₀alkyl group unsubstituted or substituted with a C₃-C₁₀cycloalkyl group or a C₄-C₂₀alkyl group unsubstituted or substituted with a C₃-C₁₀cycloalkyl group.

In Formula N51, A₅₂may be a deuterated C₁-C₆₀alkyl group unsubstituted or substituted with a C₃-C₁₀cycloalkyl group. For example, A₅₂may be a deuterated C₁-C₂₀alkyl group unsubstituted or substituted with a C₃-C₁₀cycloalkyl group.

When X₅₁in Formula 1-1 is N-[(L₇)_b7-(R₇)_c7] and the group represented by *-[(L₇)_b7-(R₇)_c7] is a group represented by Formula N51, an angle between a plane including a transition dipole moment of the organometallic compound and a plane including four atoms of a tetradentate ligand bound to a metal (M) in Formula 1-1 may be 10° or less. In addition, a horizontal orientation ratio of a transition dipole moment of the organometallic compound represented by Formula 1-1 may be in a range of about 80% to about 100%.

For example, an angle between a plane including a transition dipole moment of the organometallic compound and a plane including four atoms of a tetradentate ligand bound to a metal (or platinum) in Formula 1-1 may be in a range of about 0° to about 10°, about 0° to about 9°, about 0° to about 8°, about 0° to about 7°, about 0° to about 6°, about 0° to about 5°, about 0° to about 4°, about 0° to about 3°, about 0° to about 2°, or about 0° to about 1°. As an angle between a plane including a transition dipole moment of the organometallic compound represented by Formula 1-1 and a plane including four atoms bound to a metal in Formula 1-1 is within any of these ranges, the organometallic compound may have excellent planar properties, and a thin film formed using the organometallic compound may have excellent electrical characteristics.

In an embodiment, A₅₁may be a linear or branched C₄-C₁₀alkyl group, and A₅₂may be a hydrogen-free deuterated C₁-C₁₀alkyl group.

In one or more embodiments, A₅₁may be an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, or a sec-isopentyl group.

In one or more embodiments, A₅₂may be a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, or a sec-isopentyl group, each substituted with at least one deuterium (or a hydrogen-free methyl group, a hydrogen-free ethyl group, a hydrogen-free n-propyl group, a hydrogen-free iso-propyl group, a hydrogen-free n-butyl group, a hydrogen-free sec-butyl group, a hydrogen-free isobutyl group, a hydrogen-free tert-butyl group, a hydrogen-free n-pentyl group, a hydrogen-free tert-pentyl group, a hydrogen-free neopentyl group, a hydrogen-free isopentyl group, a hydrogen-free sec-pentyl group, a hydrogen-free 3-pentyl group, or a hydrogen-free sec-isopentyl group, each substituted with at least one deuterium).

In one or more embodiments, in Formulae 1-1 and N51, R″′, R₇, R₈, T₁₁to T₁₄, T₂₁to T₂₃, T₃₁to T₃₃, T₄₁to T₄₄, R₅₁, and R₅₂may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, —SF₅, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-237, a group represented by one of 9-201 to 9-237 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-129, a group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-350, a group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium, —Si(Q₃)(Q₄)(Q₅), or —Ge(Q₃)(Q₄)(Q₅), wherein Q₃to Q₅may respectively be understood by referring to the descriptions of Q₃to Q₅provided herein.

In one or more embodiments, in Formula N51, A₅₁may be a group represented by one of Formulae 9-4 to 9-39.

In one or more embodiments, in Formula N51, A₅₂may be a group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium.

In one or more embodiments, in Formula N51, a group represented by

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may be a group represented by one of Formulae 10-12 to 10-129:

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In Formulae 9-1 to 9-39, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, * indicates a binding site to an adjacent atom, “Ph” represents a phenyl group, “TMS” represents a trimethylsilyl group, and “TMG” represents a trimethylgermyl group.

The “group represented by one of Formulae 9-1 to 9-39 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 9-201 to 9-237 in which at least one hydrogen is substituted with deuterium” may each be, for example, a group represented by one of Formulae 9-501 to 9-514 and 9-601 to 9-636:

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The “group represented by one of Formulae 10-1 to 10-129 in which at least one hydrogen is substituted with deuterium” and the “group represented by one of Formulae 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium” may each be, for example, a group represented by one of Formulae 10-501 to 553:

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In some embodiments, in Formula N51, A₅₂may be a group represented by one of Formulae 9-1 to 9-39 in which all hydrogens are substituted with deuterium atoms.

In one or more embodiments, in Formula 1-1, X₅₁may be N-[(L₇)_b7-(R₇)_c7], and a group represented by *-[(L₇)_b7-(R₇)_c7] may be a phenyl group substituted with both 1) at least one C₄-C₁₀alkyl group and 2) at least one phenyl group.

In Formula N51, a51 and a52 may respectively indicate the number of A₅₁(s) and A₅₂(s), and a51 and a52 may each independently be an integer from 0 to 10. When a51 is 2 or greater, at least two A₅₁(s) may be identical to or different from each other. When a52 is 2 or greater, at least two A₂(s) may be identical to or different from each other.

For example, in Formula N51, a51 and a52 may each independently be 0, 1, 2, 3, 4, 5, or 6.

In Formula N51, a sum of a51 and a52 may be 1 or greater. That is, in Formula N51, ring CY₅₁is substituted with the group represented by A₅₁, the group represented by A₅₂, or any combination thereof. While not wishing to be bound by theory, ring CY₅₁is substituted with at least one electron donating group, and thus, an electronic device, e.g., an organic light-emitting device, including the organometallic compound represented by Formula 1-1 including the group represented by Formula N51 may have improved luminescence efficiency and lifespan.

In some embodiments, a sum of a51 and a52 may be 1, 2, or 3. In an embodiment, a sum of a51 and a52 may be 1.

In Formula N51, a53 indicates the number of a group represented by (R₂)S₂,

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and a53 may be an integer from 1 to 10. That is, a53 in Formula N51 may not be 0, and thus ring CY₅₁in Formula N51 is substituted with at least one group represented by

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While not wishing to be bound by theory, due to resonance effects of the group represented by

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an electronic device, e.g., an organic light-emitting device, including the organometallic compound represented by Formula 1-1 including the group represented by Formula N51, may have improved luminescence efficiency and lifespan. While not wishing to be bound by theory, because a benzimidazole group in Formula 1-1 including the group represented by Formula N51 may be protected from electrons or heat by the group represented by

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an electronic device, e.g., an organic light-emitting device, including the organometallic compound represented by Formula 1-1 may have improved luminescence efficiency and lifespan.

In an embodiment, in Formula N51, a51 and a52 may each independently be 0, 1, or 2 (e.g., 0 or 1), and a sum of a51 and a52 may be 1 or 2 (e.g., 1), and a53 may be 1 or 2 (e.g., 1).

In Formula N51, * indicates a binding site to an adjacent atom.

In one or more embodiments, in Formula N51, the group represented by

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may be a group represented by one of Formulae 51-1 to 51-20:

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wherein, in Formulae 51-1 to 51-20, R₅₁, R₅₂, c51, c52, A₅₁, and A₅₂may respectively be understood by referring to the descriptions of R₅₁, R₅₂, c51, c52, A₅₁, and A₅₂provided herein, and * indicates a binding site to L₅₁.

In one or more embodiments, in Formula 1-1, each of Z₁₂and Z₁₄may be C(H).

In one or more embodiments, in Formula 1-1, each of Z₁₁may be C-[(L₁₁)_b11-(T₁₁)_c11] and T₁₁may not be hydrogen.

In one or more embodiments, in Formula 1-1, each of Z₁₃may be C-[(L₁₃)_b13-(T₁₃)_c13] and T₁₃may not be hydrogen.

In one or more embodiments, in Formula 1-1, each of Z₂₁to Z₂₂may be C(H).

In one or more embodiments, in Formula 1-1, each of Z₃₁and Z₃₃may be C(H).

In one or more embodiments, in Formula 1-1,

Z₃₂may be C-[(L₃₂)_b32-(T₃₂)_c32],

L₃₂may be a single bond, and

T₃₂may be a substituted or unsubstituted C₁-C₀alkyl group or a substituted or unsubstituted C₆-C₀aryl group.

In one or more embodiments, in Formula 1-1, each of Z₄₁, Z₄₃and Z₄₄may be C(H).

In one or more embodiments, in Formula 1-1, each of Z₄₂may be C-[(L₄₂)_b42-(T₄₂)_c42] and T₄₂may not be hydrogen.

In one or more embodiments, in Formula 1-1,

Z₁₁may be C-[(L₁₁)_b11-(T₁₁)_c11], Z₁₂may be C-[(L₁₂)_b12-(T₁₂)_c12], Z₁₃may be C-[(L₁₃)_b13-(T₁₃)_c13], Z₁₄may be C-[(L₁₄)_b14-(T₁₄)_c14], Z₃₁may be C-[(L₃₁)_b31-(T₃₁)_c31], Z₃₂may be C-[(L₃₂)_b32-(T₃₂)_c32], Z₃₃may be C-[(L₃₃)_b33-(T₃₃)_c33],

at least one of T₁₁to T₁₄, at least one of T₃₁to T₃₃, or any combination thereof may each independently be:

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, or a sec-isopentyl group, each unsubstituted or substituted with at least one deuterium, —F, a cyano group, or any combination thereof; or

a phenyl group, or naphtyl group, each unsubstituted or substituted with at least one deuterium, —F, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, or a sec-isopentyl group, or any combination thereof.

In one or more embodiments, in Formula 1-1, a group represented by

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may be represented by one of Formulae A1-1 to A1-9:

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wherein, in Formulae A1-1 to A1-9,

Y₁, Z₁₁to Z₁₄and R_10amay respectively be understood by referring to the descriptions of Y₁, Z₁₁to Z₁₄and R_10aprovided herein,

ring CY₁₁may be a C₅-C₃₀carbocyclic group or a C₁-C₃₀heterocyclic group (for example, a cyclohexane group, a norbornane group, a benzene group, or a naphthalene group),

X₁₁may be O, S, N(R₁₁), C(R₁₁)(R₁₂), or Si(R₁₁)(R₁₂),

R₁₁and R₁₂may each be understood by referring to the description of T₁₁provided herein,

aa may be an integer from 0 to 6,

*′ indicates a binding site to X₁in Formula 1-1, and

* indicates a binding site to an adjacent atom.

In one or more embodiments, in Formula 1-1, a group represented by

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may be represented by one of Formulae A3-1 to A3-6:

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wherein, in Formulae A3-1 to A3-1,

X₃, Z₃₁to Z₃₃and R_10amay respectively be understood by referring to the descriptions of X₃, Z₃₁to Z₃₃and R_10aprovided herein,

ring CY₃₁may be a C₅-C₃₀carbocyclic group or a C₁-C₃₀heterocyclic group (for example, a cyclohexane group, a norbornane group, a benzene group, or a naphthalene group),

X₃₁may be O, S, N(R₃₁), C(R₃₁)(R₃₂), or Si(R₃₁)(R₃₂),

R₃₁and R₃₂may each be understood by referring to the description of T₃₁provided herein,

aa may be an integer from 0 to 6,

each of *″ and * indicates a binding site to an adjacent atom,

*′ indicates a binding site to M in Formula 1-1.

In one or more embodiments, in Formula 1-1, a group represented by

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may be represented by one of Formulae A4-1 to A4-9:

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wherein, in Formulae A4-1 to A4-9,

X₄, Z₄₁to Z₄₄and R_10amay respectively be understood by referring to the descriptions of X₄, Z₄₁to Z₄₄and R_10aprovided herein,

ring CY₄₁may be a C₅-C₃₀carbocyclic group or a C₁-C₃₀heterocyclic group (for example, a cyclohexane group, a norbornane group, a benzene group, or a naphthalene group),

X₄₁may be O, S, N(R₄₁), C(R₄₁)(R₄₂), or Si(R₄₁)(R₄₂),

R₄₁and R₄₂may each be understood by referring to the description of T₄₁provided herein,

aa may be an integer from 0 to 6,

*′ indicates a binding site to M in Formula 1-1, and

* indicates a binding site to an adjacent atom in Formula 1-1.

In one or more embodiments, the organometallic compound represented by Formula 1-1 may include at least one deuterium.

The organometallic compound represented by Formula 1-1 may be one of the Compounds 1 to 420:

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The organometallic compound represented by Formula 1-1 may have excellent electrical characteristics and thermal stability. Thus, an organic light-emitting device having a high luminescence efficiency may be manufactured.

A method of synthesizing the organometallic compound may be apparent to one of ordinary skill in the art by referring to Synthesis Examples provided herein.

Accordingly, the organometallic compound may be suitable for use in an organic layer of an organic light-emitting device, e.g., as a dopant in the organic layer. Thus, according to another aspect, there is provided an organic light-emitting device that may include a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer may include at least one organometallic compound represented by Formula 1-1.

The organic light-emitting device may include an organic layer including the organometallic compound. Thus, the organic light-emitting device may have excellent driving voltage, excellent luminescence efficiency and external quantum efficiency characteristics.

The organometallic compound may be used in a pair of electrodes of an organic light-emitting device. In some embodiments, the organometallic compound may be included in an emission layer. In this embodiment, the organometallic compound may serve as a dopant, and the emission layer may further include a host (that is, an amount of the organometallic compound may be smaller than that of the host in the emission layer). The emission layer may emit red light or green light, e.g., red light or green light having a maximum emission wavelength of about 500 nanometers (nm) or longer, e.g., about 500 nm to about 650 nm.

In some embodiments, the emission layer may emit green light.

As used herein, the expression the “(organic layer) includes at least one organometallic compound” may be construed as meaning the “(organic layer) may include one organometallic compound of Formula 1-1 or two different organometallic compounds of Formula 1-1”.

For example, Compound 1 may only be included in the organic layer as an organometallic compound. In this embodiment, Compound 1 may be included in the emission layer of the organic light-emitting device. In some embodiments, Compounds 1 and 2 may be included in the organic layer as organometallic compounds. In this embodiment, Compounds 1 and 2 may both be included in the same layer (for example, both Compounds 1 and 2 may be included in the emission layer).

The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode. In some embodiments, the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.

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

The term “organic layer” as used herein refers to a single and/or a plurality of layers between the first electrode and the second electrode in an organic light-emitting device. The “organic layer” may include not only organic compounds but also organometallic complexes including metals.

The FIGURE illustrates a schematic cross-sectional view of an organic light-emitting device 10 according to an exemplary embodiment. Hereinafter, a structure of an organic light-emitting device according to one or more embodiments and a method of manufacturing the organic light-emitting device will be described with reference to the FIGURE. The organic light-emitting device 10 may include a first electrode 11, an organic layer 15, and a second electrode 19, which may be sequentially layered in this stated order.

A substrate may be additionally disposed under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in organic light-emitting devices, e.g., a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water repellency.

First Electrode 11 in Organic Light-Emitting Device 10

The first electrode 11 may be formed by depositing or sputtering, onto the substrate, a material for forming the first electrode 11. The first electrode 11 may be an anode. The material for forming the first electrode 11 may include a material with a high work function for easy 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 some 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).

The first electrode 11 may have a single-layered structure or a multi-layered structure including a plurality of layers. In some embodiments, the first electrode 11 may have a triple-layered structure of ITO/Ag/ITO.

The organic layer 15 may be on the first electrode 11.

Organic layer 15 in organic light-emitting device 10

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

Hole Transport Region in Organic Layer 15

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

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.

The hole transport region may include a hole injection layer only or a hole transport layer only. In some embodiments, the hole transport region may include a hole injection layer and a hole transport layer which are sequentially stacked on the first electrode 11. In some embodiments, the hole transport region may include a hole injection layer, a hole transport layer, and an electron blocking layer, which are sequentially stacked on the first electrode 11.

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

When a hole injection layer is formed by vacuum-deposition, for example, the vacuum deposition may be performed at a temperature in a range of about 100° C. to about 500° C., at a vacuum pressure in a range of about 10⁻⁸torr to about 10⁻³torr, and at a rate in a range of about 0.01 Angstroms per second (Å/sec) to about 100 Å/sec, though the conditions may vary depending on a compound used as a hole injection material and a structure and thermal properties of a desired hole injection layer.

When a hole injection layer is formed by spin coating, the spin coating may be performed at a rate in a range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and at a temperature in a range of about 80° C. to 200° C. to facilitate removal of a solvent after the spin coating, though the conditions may vary depending on a compound used as a hole injection material and a structure and thermal properties of a desired hole injection layer.

The conditions for forming a hole transport layer and an electron blocking layer may be inferred from the conditions for forming the hole injection layer.

The hole transport region may include m-MTDATA, TDATA, 2-TNATA, NPB, 3-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/camphor-sulfonic acid (PANI/CSA), polyaniline/poly(4-styrene sulfonate) (PANI/PSS), a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

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wherein, in Formula 201, Ar₁₀₁and Ar₁₀₂may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof.

In Formula 201, xa and xb may each independently be an integer from 0 to 5. In some embodiments, xa and xb may each independently be an integer from 0 to 2. In some embodiments, xa may be 1, and xb may be 0.

In Formulae 201 and 202, R₁₀₁to R₁₀₈, R₁₁₁to R₁₁₉, and R₁₂₁to R₁₂₄may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group (e.g., a methyl group, an ethyl group, a propyl group, a butyl group, pentyl group, or a hexyl group), or a C₁-C₁₀alkoxy group (e.g., a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group);

a C₁-C₁₀alkyl group or a C₁-C₁₀alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or any combination thereof; or

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, or any combination thereof.

In Formula 201, R₁₀₉may be a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or any combination thereof.

In some embodiments, the compound represented by Formula 201 may be represented by Formula 201A:

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wherein, in Formula 201A, R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉may respectively be understood by referring to the descriptions of R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉provided herein.

In some embodiments, the hole transport region may include one of Compounds HT1 to HT21 or any combination thereof:

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The thickness of the hole transport region may be in a range of about 100 Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 3,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, the thickness of the hole injection layer may be in a range of about 50 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, excellent hole transport characteristics may be obtained without a substantial increase in driving voltage.

The hole transport region may include a charge generating material as well as the aforementioned materials, to improve conductive properties of the hole transport region. The charge generating material may be substantially homogeneously or non-homogeneously dispersed in the hole transport region.

The charge generating material may include, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a compound containing a cyano group, or any combination thereof. In some embodiments, the p-dopant may be a quinone derivative, such as tetracyanoquinodimethane (TCNQ), a 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), or F6-TCNNQ; a metal oxide, such as a tungsten oxide or a molybdenum oxide; a compound containing a cyano group, such as Compound HT-D1; or any combination thereof:

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The hole transport region may further include a buffer layer.

The buffer layer may compensate for an optical resonance distance depending on a wavelength of light emitted from the emission layer to improve the efficiency of an organic light-emitting device.

When the hole transport region includes an electron blocking layer, a material for forming the electron blocking layer may include the material for forming a hole transport region, the host material described herein or any combination thereof. In some embodiments, when the hole transport region includes an electron blocking layer, mCP described herein, Compound H21, H-H1, or any combination thereof may be used for forming the electron blocking layer.

Emission Layer in Organic Layer 15

An emission layer may be formed on the hole transport region by using one or more suitable methods, such as vacuum deposition, spin coating, casting, or LB deposition. When the emission layer is formed by vacuum deposition or spin coating, vacuum deposition and coating conditions for forming the emission layer may be generally similar to those conditions for forming a hole injection layer, though the conditions may vary depending on a compound that is used.

The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1-1 described herein.

Host in Emission Layer

The host may include TPBi, TBADN, ADN (also known as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, Compound H52, or any combination thereof:

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The host may consist of one type of compound or a mixture of at least two different kinds of compounds.

In an embodiment, the host may include an electron transporting host including at least one electron transporting moiety, a hole transporting host not including an electron transporting moiety, or any combination thereof.

The electron transporting moiety may include a cyano group, a π electron-depleted nitrogen-containing cyclic group, a group represented by one of following Formulae, or any combination thereof:

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wherein, in the Formulae above, *, *′, and *″ may each indicate a binding site to an adjacent atom.

For example, the electron transporting host may include at least one π electron-rich cyclic group and at least one electron transporting moiety.

In some embodiments, the hole transporting host may include at least one π electron-rich cyclic group and not include an electron transporting moiety.

In one or more embodiments, the host may include an electron transporting host and a hole transporting host, and the electron transporting host may be different from the hole transporting host.

The term “π electron-depleted nitrogen-containing cyclic group” as used herein refers to a cyclic group having at least one *—N=*′ moiety. Examples thereof may include an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group.

The π electron-rich cyclic group refers to a cyclic group not including a *—N=*′ moiety. Examples thereof may include a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, and a triindolobenzene group.

According to another embodiment, the electron transporting host may include a compound represented by Formula E-1.

In one or more embodiments, the hole transporting host may include a compound represented by Formula H-1.

[Ar₃₀₁]_xb11-[(L₃₀₁)_xb1-R₃₀₁]_xb21 Formula E-1

wherein, in Formula E-1,

Ar₃₀₁may be a C₅-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

xb11 may be 1, 2, or 3,

L₃₀₁may each independently be a single bond, a group represented by one of the Formulae below, a C₅-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, wherein in Formulae, *, *′, and *″ each indicate a binding site to an adjacent atom,

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xb1 may be an integer from 1 to 5,

R₃₀₁may be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂), —B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), —S(═O)(Q₃₀₁), —P(═O)(Q₃₀₁)(Q₃₀₂), or —P(═S)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5,

wherein Q₃₀₁to Q₃₀₃may each independently be a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group,

R_10amay be understood by referring to the description of T₁₁provided herein, and at least one of Conditions 1 to 3 may be satisfied:

Condition 1

at least one of Ar₃₀₁, L₃₀₁, and R₃₀₁in Formula E-1 may each independently include a π electron-depleted nitrogen-containing cyclic group,

Condition 2

L₃₀₁in Formula E-1 may be a group represented by one of the following Formulae:

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Condition 3

R₃₀₁in Formula E-1 may be a cyano group, —S(═O)₂(Q₃₀₁), —S(═O)(Q₃₀₁), —P(═O)(Q₃₀₁)(Q₃₀₂), or —P(═S)(Q₃₀₁)(Q₃₀₂).

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wherein, in Formulae H-1, 11, and 12,

L₄₀₁may be:

a single bond; or

a π electron-rich cyclic group (e.g., a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or a triindolobenzene group) unsubstituted or substituted with deuterium, a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a π electron-rich cyclic group (e.g., a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triphenylenyl group, a biphenyl group, a terphenyl group, or a tetraphenyl group (or, quaterphenyl)), —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), or any combination thereof,

xd1 may be an integer from 1 to 10, and when xd1 is 2 or greater, at least two L₄₀₁(s) may be identical to or different from each other,

Ar₄₀₁may be a group represented by Formula 11 or a group represented by Formula 12,

Ar₄₀₂may be:

a group represented by Formula 11 or a group represented by Formula 12; or

a π electron-rich cyclic group (e.g., a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group) unsubstituted or substituted with deuterium, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a π electron-rich cyclic group (e.g., a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group), or any combination thereof,

xd11 may be an integer from 0 to 10 (for example, an integer from 1 to 10), and when xd11 is 2 or greater, at least two Ar₄₀₂(s) may be identical to or different from each other,

CY₄₀₁and CY₄₀₂may each independently be a π electron-rich cyclic group (e.g., a benzene group, a naphthalene group, a fluorene group, a carbazole group, a benzocarbazole group, an indolocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a benzonaphthofuran group, a benzonapthothiophene group, or a benzonaphthosilole group),

A₂₁may be a single bond, O, S, N(R₅₁), C(R₅₁)(R₅₂), or Si(R₅₁)(R₅₂),

A₂₂may be a single bond, O, S, N(R₅₃), C(R₅₃)(R₅₄), or Si(R₅₃)(R₅₄),

at least one of A₂₁and A₂₂in Formula 12 may not be a single bond,

R₅₁to R₅₄and R₄₀₁to R₄₀₂may each independently be:

hydrogen or deuterium;

a C₁-C₂₀alkyl group and a C₁-C₂₀alkoxy group, each unsubstituted or substituted with deuterium, a π electron-rich cyclic group (e.g., a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group), or any combination thereof;

—Si(Q₄₀₄)(Q₄₀₅)(Q₄₀₆),

e1 and e2 may each independently be an integer from 0 to 10,

wherein Q₄₀₁to Q₄₀₆may each independently be hydrogen, deuterium, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, or a π electron-rich cyclic group (e.g., a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a biphenyl group), and

* indicates a binding site to an adjacent atom.

In an embodiment, in Formula E-1, Ar₃₀₁may be a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof,

at least one of L₃₀₁(s) in the number of xb1 may each independently be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof, and

R₃₀₁may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁to Q₃₃may each independently be a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

In one or more embodiments, R₃₀₁may be represented by one of Formulae 7-1 to 7-9:

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The electron transporting host may be, for example, at least one of Compounds H-E1 to H-E84:

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In some embodiments, the hole transporting host may be at least one of Compounds H-H1 to H-H103:

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In some embodiments, the host may include an electron transporting host and a hole transporting host, the electron transporting host may include a triphenylene group and a triazine group, and the hole transporting host may include a carbazole group.

A weight ratio of the electron transporting host to the hole transporting host may be in a range of about 1:9 to about 9:1, for example, about 2:8 to about 8:2, or for example, about 4:6 to about 6:4. When a weight ratio of the electron transporting host to the hole transporting host is within any of these ranges, holes and electrons transport balance into the emission layer may be achieved.

When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In some embodiments, the emission layer may have a structure in which the red emission layer, the green emission layer, and/or the blue emission layer are layered to emit white light. In some embodiments, the structure of the emission layer may vary.

When the emission layer includes the host and the dopant, an amount of the dopant may be selected from a range of about 0.01 parts to about 15 parts by weight based on about 100 parts by weight of the host.

The thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, and in some embodiments, about 200 Å to about 600 Å. When the thickness of the emission layer is within any of these ranges, improved luminescence characteristics may be obtained without a substantial increase in driving voltage.

Electron Transport Region in Emission Layer

Next, an electron transport region may be formed on the emission layer.

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

In some embodiments, the electron transport region may have a hole blocking layer/an electron transport layer/an electron injection layer structure or an electron transport layer/an electron injection layer structure. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.

The conditions for forming a hole blocking layer, an electron transport layer, and an electron injection layer may be inferred based on the conditions for forming the hole injection layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, BAlq, or any combination thereof:

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In some embodiments, the hole blocking layer may include the host, the material for forming an electron transport layer described herein, the material for forming an electron injection layer described herein, or any combination thereof.

The thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 600 Å. When the thickness of the hole blocking layer is within any of these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.

The electron transport layer may include BCP, Bphen, TPBi, Alq₃, BAlq, TAZ, NTAZ, or any combination thereof:

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In some embodiments, the electron transport layer may include one of Compounds ET1 to ET25 or any combination thereof:

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The thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, and in some embodiments, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within any of these ranges, excellent electron transport characteristics may be obtained without a substantial increase in driving voltage.

The electron transport layer may further include a material containing metal, in addition to the materials described above.

The material containing metal may include a Li complex. The Li complex may include, e.g., Compound ET-D1 or Compound ET-D2:

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The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 19.

The electron injection layer may include LiF, NaCl, CsF, Li₂O, BaO, or any combination thereof.

The thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and in some embodiments, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within any of these ranges, excellent electron injection characteristics may be obtained without a substantial increase in driving voltage.

The second electrode 19 may be on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be a material with a relatively low work function, such as a metal, an alloy, an electrically conductive compound, or any combination thereof. Examples of the material for forming the second electrode 19 may include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag). In some embodiments, ITO or IZO may be used to form a transmissive second electrode 19 to manufacture a top emission light-emitting device. In some embodiments, the material for forming the second electrode 19 may vary.

Hereinbefore the organic light-emitting device 10 has been described with reference to the FIGURE, but embodiments are not limited thereto.

According to an aspect of another embodiment, an electronic apparatus may include the organic light-emitting device. Thus, an electronic apparatus including the organic light-emitting device may be provided. The electronic apparatus may include, for example, a display, lighting, a sensor, or the like.

According to an aspect of still another embodiment, a diagnostic composition may include at least one organometallic compound represented by Formula 1-1.

Since the organometallic compound represented by Formula 1-1 provides high luminescence efficiency, the diagnostic efficiency of the diagnostic composition that includes the organometallic compound represented by Formula 1-1 may be excellent.

The diagnostic composition may be applied in various ways, such as in a diagnostic kit, a diagnostic reagent, a biosensor, or a biomarker.

The term “C₁-C₆₀alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and the term “C₁-C₆₀alkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₆₀alkyl group.

Examples of the C₁-C₆₀alkyl group, the C₁-C₂₀alkyl group, and/or the C₁-C₁₀alkyl group as used herein may include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group or a tert-decyl group, each unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, or any combination thereof. In some embodiments, Formula 9-33 may be a branched C₆alkyl group. Formula 9-33 may be a tert-butyl group substituted with two methyl groups.

The term “C₁-C₆₀alkoxy group” as used herein refers to a monovalent group represented by —OA₁₀₁(wherein A₁₀₁is a C₁-C₆₀alkyl group).

Examples of the C₁-C₆₀alkoxy group, the C₁-C₂₀alkoxy group, or the C₁-C₁₀alkoxy group as used herein may include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group.

The term “C₂-C₆₀alkenyl group” as used herein refers to a group formed by placing at least one carbon-carbon double bond in the middle or at the terminus of the C₂-C₆₀alkyl group. Examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C₂-C₆₀alkenylene group” as used herein refers to a divalent group having the same structure as the C₂-C₆₀alkenyl group.

The term “C₂-C₆₀alkynyl group” as used herein refers to a group formed by placing at least one carbon-carbon triple bond in the middle or at the terminus of the C₂-C₆₀alkyl group. Examples thereof include an ethynyl group and a propynyl group. The term “C₂-C₆₀alkynylene group” as used herein refers to a divalent group having the same structure as the C₂-C₆₀alkynyl group.

The term “C₃-C₁₀cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms. The term “C₃-C₁₀cycloalkylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀cycloalkyl group.

Examples of the C₃-C₁₀cycloalkyl group as used herein may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, or a bicyclo[2.2.2]octyl group.

The term “C₁-C₁₀heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having 1 to 10 carbon atoms and at least one heteroatom of N, O, P, Si, S, Ge, Se and B as a ring-forming atom. The term “C₁-C₁₀heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₁₀heterocycloalkyl group.

Examples of the C₁-C₁₀heterocycloalkyl group as used herein may include a silolanyl group, a silinanyl group, a tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, or a tetrahydrothiophenyl group.

The term “C₃-C₁₀cycloalkenyl group” as used herein refers to a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, wherein the molecular structure as a whole is non-aromatic. Examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

The term “C₁-C₁₀heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group including at least one heteroatom of N, O, P, Si, S, Ge, Se and B as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Examples of the C₁-C₁₀heterocycloalkenyl group include a 2,3-dihydrofuranyl group and a 2,3-dihydrothiophenyl group. The term “C₁-C₁₀heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₁-C₁₀heterocycloalkenyl group.

The term “C₆-C₆₀aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. The term “C₆-C₆₀arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C₆-C₆₀aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀aryl group and the C₆-C₆₀arylene group each include a plurality of rings, the plurality of rings may be fused to each other.

The term “C₇-C₆₀alkyl aryl group” as used herein refers to a C₆-C₆₀aryl group substituted with at least one C₁-C₆₀alkyl group.

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom of N, O, P, Si, S, Ge, Se and B as a ring-forming atom and 1 to 1 carbon atoms. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom of N, O, P, Si, S, Ge, Se and B as a ring-forming atom and 1 to 60 carbon atoms. Examples of the C₁-C₆₀heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀heteroarylene group each include a plurality of rings, the plurality of rings may be fused to each other.

The term “C₂-C₆₀alkyl heteroaryl group” as used herein refers to a C₁-C₆₀heteroaryl group substituted with at least one C₁-C₆₀alkyl group.

The term “C₆-C₆₀aryloxy group” as used herein is represented by —OA₁₀₂(wherein A₁₀₂is the C₆-C₆₀aryl group). The term “C₆-C₆₀arylthio group” as used herein is represented by —SA₁O₃(wherein A₁₀₃is the C₆-C₆₀aryl group). The term “C₁-C₆₀alkylthio group” as used herein is represented by —SA₁O₄(wherein A₁₀₄is the C₁-C₆alkyl group).

The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group that has two or more condensed rings and only carbon atoms (e.g., the number of carbon atoms may be in a range of 8 to 60) as ring-forming atoms, wherein the molecular structure as a whole is non-aromatic. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group that has two or more condensed rings and a heteroatom selected from N, O, P, Si, S, Ge, Se and B and carbon atoms (e.g., the number of carbon atoms may be in a range of 1 to 60) as ring-forming atoms, wherein the molecular structure as a whole is non-aromatic. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

The term “C₅-C₃₀carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group including 5 to 30 carbon atoms only as ring-forming atoms. The C₅-C₃₀carbocyclic group may be a monocyclic group or a polycyclic group. Examples of the “C₅-C₃₀carbocyclic group (unsubstituted or substituted with at least one R_10a)” may include an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group (a norbornane group), a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, or a fluorene group, each unsubstituted or substituted with at least one R_10a.

The term “C₁-C₃₀heterocyclic group” as used herein refers to saturated or unsaturated cyclic group including 1 to 30 carbon atoms and at least one heteroatom selected from N, O, P, Si, Se, Ge, B, and S as ring-forming atoms. The C₁-C₃₀heterocyclic group may be a monocyclic group or a polycyclic group. Examples of the “C₁-C₃₀heterocyclic group (unsubstituted or substituted with at least one R_10a)” may include a thiophene group, a furan group, a pyrrole group, a silole group, a borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole 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 pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group, each unsubstituted or substituted with at least one R_10a.

Examples of the “C₅-C₃₀carbocyclic group” and the “C₁-C₃₀heterocyclic group” as used herein include i) a first ring, ii) a second ring, iii) a condensed ring in which at least two first rings are condensed, iv) a condensed ring in which at least two second rings are condensed, or v) a condensed ring in which at least one first ring and at least one second ring are condensed,

the first ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an isoxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, or a triazasilole group, and

the second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

The “fluorinated C₁-C₆₀alkyl group (or fluorinated C₁-C₂₀alkyl group or the like)”, “fluorinated C₃-C₁₀cycloalkyl group”, “fluorinated C₁-C₁₀heterocycloalkyl group”, and “fluorinated phenyl group” as used herein may respectively be a C₁-C₆₀alkyl group (or C₁-C₂₀alkyl group or the like), C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, and a phenyl group, each substituted with at least one fluoro group (—F). Examples of the “fluorinated C₁alkyl group (i.e., a fluorinated methyl group)” may include —CF₃, —CF₂H, and —CFH₂. The “fluorinated C₁-C₆₀alkyl group (or fluorinated C₁-C₂₀alkyl group or the like)”, “fluorinated C₃-C₁₀cycloalkyl group”, “fluorinated C₁-C₁₀heterocycloalkyl group”, or “fluorinated phenyl group” may respectively be: i) a fully fluorinated C₁-C₆₀alkyl group (or fully fluorinated C₁-C₂₀alkyl group or the like), fully fluorinated C₃-C₁₀cycloalkyl group, fully fluorinated C₁-C₁₀heterocycloalkyl group, or fully fluorinated phenyl group, in which all hydrogen atoms are substituted with fluoro groups; or ii) a partially fluorinated C₁-C₆₀alkyl group (or partially fluorinated C₁-C₂₀alkyl group or the like), partially fluorinated C₃-C₁₀cycloalkyl group, partially fluorinated C₁-C₁₀heterocycloalkyl group, or partially fluorinated phenyl group, in which some of hydrogen atoms are substituted with fluoro groups.

The “deuterated C₁-C₆₀alkyl group (or deuterated C₁-C₂₀alkyl group or the like)”, “deuterated C₃-C₁₀cycloalkyl group”, “deuterated C₁-C₁₀heterocycloalkyl group”, and “deuterated phenyl group” as used herein may respectively be a C₁-C₆₀alkyl group (or C₁-C₂₀alkyl group or the like), C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, and a phenyl group, each substituted with at least one deuterium. Examples of the “deuterated C₁alkyl group (i.e., a deuterated methyl group)” may include —CD₃, —CD₂H, and —CDH₂. Examples of the “deuterated C₃-C₁₀cycloalkyl group” may include Formula 10-501. The “deuterated C₁-C₆₀alkyl group (or deuterated C₁-C₂₀alkyl group or the like)”, “deuterated C₃-C₁₀cycloalkyl group”, “deuterated C₁-C₁₀heterocycloalkyl group”, or deuterated phenyl group may respectively be: i) a fully deuterated C₁-C₆₀alkyl group (or fully deuterated C₁-C₂₀alkyl group or the like), fully deuterated C₃-C₁₀cycloalkyl group, fully deuterated C₁-C₁₀heterocycloalkyl group, or fully deuterated phenyl group, in which all hydrogens are substituted with deuterium atoms; or ii) a partially deuterated C₁-C₆₀alkyl group (or partially deuterated C₁-C₂₀alkyl group or the like), partially deuterated C₃-C₁₀cycloalkyl group, partially deuterated C₁-C₁₀heterocycloalkyl group, or partially deuterated phenyl group, in which some of hydrogens are substituted with deuterium atoms.

The “(C₁-C₂₀alkyl)‘X’ group” refers to a ‘X’ group substituted with at least one C₁-C₂₀alkyl group. For example, The “(C₁-C₂₀alkyl)C₃-C₁₀cycloalkyl group” as used herein refers to a C₃-C₁₀cycloalkyl group substituted with at least one C₁-C₂₀alkyl group, and the “(C₁-C₂₀alkyl)phenyl group” as used herein refers to a phenyl group substituted with at least one C₁-C₂₀alkyl group. Examples of the (C₁alkyl)phenyl group may include a toluyl group.

In the present specification, “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, and an azadibenzothiophene 5,5-dioxide group” each refer to a hetero ring in which at least one ring-forming carbon atom is substituted with nitrogen atom and respectively having an identical backbone as “an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, and a dibenzothiophene 5,5-dioxide group”.

A substituent of the substituted C₅-C₃₀carbocyclic group, the substituted C₁-C₃₀heterocyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₁-C₆₀alkylthio group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₇-C₆₀alkyl aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted C₂-C₆₀alkyl heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may each independently be:

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, or a C₁-C₆₀alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₇-C₆₀alkyl aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉), —P(Q₁₈)(Q₁₉), or any combination thereof;

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₇-C₆₀alkyl aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₇-C₆₀alkyl aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), —P(Q₂₈)(Q₂₉), or any combination thereof;

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), —P(═O)(Q₃₈)(Q₃₉), or —P(Q₃₈)(Q₃₉); or

any combination thereof.

In the present specification, Q₁to Q₉, Q₁₁to Q₁₉, Q₂₁to Q₂₉, and Q₃₁to Q₃₉may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C₁-C₆₀alkyl group unsubstituted or substituted with deuterium, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or any combination thereof; a C₂-C₆₀alkenyl group; a C₂-C₆₀alkynyl group; a C₁-C₆₀alkoxy group; a C₃-C₁₀cycloalkyl group; a C₁-C₁₀heterocycloalkyl group; a C₃-C₁₀cycloalkenyl group; a C₁-C₁₀heterocycloalkenyl group; a C₆-C₆₀aryl group unsubstituted or substituted with deuterium, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or any combination thereof; a C₆-C₆₀aryloxy group; a C₆-C₆₀arylthio group; a C₁-C₆₀heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

Hereinafter, a compound and an organic light-emitting device according to an embodiment will be described in detail with reference to Synthesis Examples and Examples, however, the present disclosure is not limited thereto. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of B used was identical to an amount of A used based on molar equivalence.

EXAMPLES
Synthesis Example 1 (Compound 1)

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Synthesis of ligand C-1 (2-(1-([1,1′-biphenyl]-2-yl)-4-(3-(tert-butyl)-5-(4-(4-(2-phenylpropan-2-yl)phenyl)pyridin-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-4,6-di-tert-butylphenol)

5.7 grams (g) of Intermediate B-1 (0.011 mol, 0.9 equiv.), 6.6 g of Intermediate A-1 (0.012 mol, 1 equiv.), 0.96 g of tetrakis(triphenylphosphine)palladium(0) (0.001 mmol, 0.07 equiv.), and 4.9 g of potassium carbonate (0.036 mol, 3 equiv.) were dissolved in 80 milliliters (mL) of a solvent in which tetrahydrofuran (THF) and distilled water (H₂O) were mixed at a volume ratio of 3:1, followed by reflux for 12 hours. The resulting product was cooled to room temperature, and a precipitate was filtered to obtain a filtrate. The obtained filtrate was washed with EA (ethyl acetate) and H₂O, the organic layer was concentrated and purified by column chromatography with gradient elution (while increasing a rate of EA/hexane to between 8% and 15%), and recrystallization was performed using MC (methylene chloride)/MeOH to obtain 4.8 g of Ligand C-1 (having a purity of 99% or higher). The resulting compound was identified by using mass spectroscopy and HPLC analysis.

HRMS(MALDI) calcd for C₆₃H₆₃N₃O: m/z 877.4971, Found: 877.4975

Synthesis of Compound 1

4.9 g of ligand C-1 (5.55 mmol) and 2.76 g of K₂PtCl₄(6.65 mmol, 1.2 equiv.) were dissolved in 110 mL of a mixture of 100 mL of AcOH (acetic acid) and 10 mL of H₂O, followed by reflux for 16 hours. The resulting product was cooled to room temperature, and a precipitate was filtered to obtain a filtrate. The obtained filtrate was extracted with methylene chloride (MC) and washed with H₂O, the organic layer was concentrated, and the obtained residue was purified by column chromatography to obtain 2.2 g of Compound 1 (yield: 37%). The resulting compound was identified by using mass spectroscopy and HPLC analysis.

HRMS(MALDI) calcd for C₆₃H₆₁N₃OPt: m/z 1070.4462, Found: 1070.4464

Synthesis Example 2 (Compound 3)

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Synthesis of ligand C-3 (2,4-di-tert-butyl-6-(4-(3-(tert-butyl)-5-(4-(4-(4-phenylcyclohexyl-1,4-d2)phenyl)pyridin-2-yl)phenyl)-1-(5-(tert-butyl)-[1,1′-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)phenol)

3.4 grams (g) of Intermediate B-3 (0.006 mol, 0.9 equiv.), 4.0 g of Intermediate A-3 (0.006 mol, 1 equiv.), 0.53 g of tetrakis(triphenylphosphine)palladium(0) (0.001 mmol, 0.07 equiv.), and 2.7 g of potassium carbonate (0.020 mol, 3 equiv.) were dissolved in 80 milliliters (mL) of a solvent in which tetrahydrofuran (THF) and distilled water (H₂O) were mixed at a volume ratio of 3:1, followed by reflux for 12 hours. The resulting product was cooled to room temperature, and a precipitate was filtered to obtain a filtrate. The obtained filtrate was washed with EA and H₂O, the organic layer was concentrated, and the resulting residue was purified by column chromatography with gradient elution (while increasing a rate of EA/hexane to between 8% and 15%), and recrystallization was performed using MC/MeOH to obtain 4.5 g of Ligand C-3 (having a purity of 99% or higher). The resulting compound was identified by using mass spectroscopy and HPLC analysis.

HRMS(MALDI) calcd for C₇₀H₇₃D₂N₃O: m/z 975.6036, Found: 975.6039

Synthesis of Compound 3

4.5 g of ligand C-3 (5.25 mmol) and 2.61 g of K₂PtCl₄(6.30 mmol, 1.2 equiv.) were dissolved in 100 mL of a mixture of 100 mL of AcOH and 10 mL of H₂O, followed by reflux for 16 hours. The resulting product was cooled to room temperature, and a precipitate was filtered to obtain a filtrate. The obtained filtrate was extracted with MC and washed with H₂O, the organic layer was concentrated to obtain a residue, and the obtained residue was purified by column chromatography (MC 40%, Hexane 60%) to obtain 1.84 g of Compound 3 (yield: 30%). The resulting compound was identified by using mass spectroscopy and HPLC analysis.

HRMS(MALDI) calcd for C₇₀H₇₁D₂N₃OPt: m/z 1168.5527, Found: 1168.5528

Synthesis Example 3 (Compound 177)

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Synthesis of Ligand C-177

3.0 g of ligand C-177 (having a purity of 98% or higher) was obtained in substantially the same manner as in Synthesis of ligand C-3 in Synthesis Example 2, except that Intermediate A-177 and Intermediate B-177 were used instead of Intermediate A-3 and Intermediate B-3, respectively. The resulting compound was identified by using mass spectroscopy and HPLC analysis.

HRMS(MALDI) calcd for C₆₆H₆₅D₂N₃₀: m/z 919.5410, Found: 919.5412

Synthesis of Compound 177

1.2 g of Compound 177 (yield: 34%) was obtained in substantially the same manner as in Synthesis of Compound 3 in Synthesis Example 2, except that ligand C-177 was used instead of ligand C-3. The resulting compound was identified by using mass spectroscopy and HPLC analysis.

HRMS(MALDI) calcd for C₆₆H₆₃D₂N₃OPt: m/z 1112.4901, Found: 1112.4903

Synthesis Example 4 (Compound 187)

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Synthesis of Ligand C-187

3.2 g of ligand C-187 (having a purity of 98% or higher) was obtained in substantially the same manner as in Synthesis of ligand C-3 in Synthesis Example 2, except that Intermediate B-187 was used instead of Intermediate B-3. The resulting compound was identified by using mass spectroscopy and HPLC analysis.

HRMS(MALDI) calcd for C₆₄H₇₃N₃O: m/z 899.5754, Found: 899.5757

Synthesis of Compound 187

1.67 g of Compound 187 (yield: 43%) was obtained in substantially the same manner as in Synthesis of Compound 3 in Synthesis Example 2, except that ligand C-187 was used instead of ligand C-3. The resulting compound was identified by using mass spectroscopy and HPLC analysis.

HRMS(MALDI) calcd for C₆₄H₇₁N₃OPt: m/z 1092.5245, Found: 1092.5243 Synthesis Example 5 (Compound 218)

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Synthesis of Ligand C-218

2.8 g of ligand C-218 (having a purity of 97% or higher) was obtained in substantially the same manner as in Synthesis of ligand C-3 in Synthesis Example 2, except that Intermediate B-1 was used instead of Intermediate B-3. The resulting compound was identified by using mass spectroscopy and HPLC analysis.

HRMS(MALDI) calcd for C₆₇H₇₁N₃O: m/z 933.5597, Found: 933.5599

Synthesis of Compound 218

1.39 g of Compound 218 (yield: 41%) was obtained in substantially the same manner as in Synthesis of Compound 3 in Synthesis Example 2, except that ligand C-218 was used instead of ligand C-3. The resulting compound was identified by using mass spectroscopy and HPLC analysis.

HRMS(MALDI) calcd for C₆₇H₆₉N₃OPt: m/z 1126.5088, Found: 1126.5087

Synthesis Example 6 (Compound 246)

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Synthesis of Ligand C-246

3.0 g of ligand C-246 (having a purity of 97% or higher) was obtained in substantially the same manner as in Synthesis of ligand C-3 in Synthesis Example 2, except that Intermediate B-246 was used instead of Intermediate B-3. The resulting compound was identified by using mass spectroscopy and HPLC analysis.

HRMS(MALDI) calcd for C₆₄H₇₁N₃O: m/z 897.5597, Found: 897.5599

Synthesis of Compound 246

1.42 g of Compound 246 (yield: 39%) was obtained in substantially the same manner as in Synthesis of Compound 3 in Synthesis Example 2, except that ligand C-246 was used instead of ligand C-3. The resulting compound was identified by using mass spectroscopy and HPLC analysis.

HRMS(MALDI) calcd for C₆₄H₆₉N₃OPt: m/z 1090.5088, Found: 1090.5087

Evaluation Example 1: Evaluation on Singlet (S1) Energy Level and Triplet (T1) Energy Level

The singlet (S₁) energy level and the triplet (T₁) energy level of the organometallic Compounds 1, 3, 177, 187, 218 and 246 and Compounds A, B, and C were evaluated by using a Gaussian program according to a density functional theory (DFT) method (structure optimization was performed at a degree of B3LYP, and 6-31 G(d,p)). The results thereof are shown in Table 1.

TABLE 1

Compound No.
S₁(eV)
T₁(eV)
ΔST (eV)

1
2.515
2.371
0.144

3
2.527
2.369
0.158

177
2.510
2.347
0.163

187
2.512
2.352
0.160

218
2.485
2.342
0.143

246
2.512
2.353
0.159

A
2.521
2.215
0.306

B
2.741
2.244
0.497

C
2.751
2.517
0.234

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As shown in Table 1, Compounds 1, 3, 177, 187, 218 and 246 were found to have ΔST in a range of 0.1 eV to 0.2 eV.

Evaluation Example 2: Evaluation of Horizontal Orientation Ratio

mCP and Compound 1 were co-deposited on a quartz substrate at a weight ratio of 92:8 in a vacuum pressure of 10-7 torr to form a film having a thickness of 40 nm. Then, a glass substrate for encapsulation was attached on the film to encapsulate the film.

The photoluminescence (PL) intensity according to angle of the film was measured by using a Luxol-OLED/analyzer LOA-100 (available from CoCoLink) from −150° to +150°. Then, the horizontal orientation ratio of Compound 1 was calculated by using a fitting program of the analyzer. The results thereof are shown in Table 2. The same process was performed on the compounds shown in Table 2. The results thereof are also shown in Table 2.

TABLE 2

Horizontal orientation

Sample No.
Co-deposition material
ratio (%)

1
mCP:Compound 1 (8 wt %)
89

3
mCP:Compound 3 (8 wt %)
94

177
mCP:Compound 177 (8 wt %)
91

187
mCP:Compound 187 (8 wt %)
90

218
mCP:Compound 218 (8 wt %)
92

246
mCP:Compound 246 (8 wt %)
92

A
mCP:Compound A (8 wt %)
75

B
mCP:Compound B (8 wt %)
75

C
mCP:Compound C (8 wt %)
71

Referring to the results of Table 2, the horizontal orientation ratios of Compounds 1, 3, 177, 187, 218 and 246 were found to be higher than the horizontal orientation ratios of Compounds A, B, and C.

Evaluation Example 3: Thermal Characteristics Evaluation

Thermal analysis (N₂atmosphere, a temperature range: from room temperature to 800° C. (10° C./min)-TGA, from room temperature to 400° C.-DSC, Pan Type: Pt Pan in disposable Al Pan (TGA) and disposable Al pan (DSC)) was performed on Compounds 1, 3, 177, 187, 218 and 246 by using thermo gravimetric analysis (TGA) and differential scanning calorimetry (DSC). The evaluation results are shown in Table 3.

TABLE 3

Compound No.
Ts_10% (° C.)

1
291

177
325

187
285

218
299

246
300

Referring to the results of Table 3, Compounds 1, 177, 187, 218 and 246 were each found to have a relatively low sublimation temperature. Thus, a thin film having excellent performance may be prepared by using above compounds.

Example 1

A glass substrate, on which ITO is patterned as an anode, was cut to a size of 50 millimeters (mm)×50 mm×0.5 mm, sonicated in isopropyl alcohol and water for 5 minutes each, and cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Subsequently, the glass substrate was mounted on a vacuum-deposition device.

HT3 and F6-TCNNQ were vacuum-co-deposited at a weight ratio of 98:2 on the anode to form a hole injection layer having a thickness of 100 Å. HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,350 Å. Then, H-H1 was vacuum-deposited on the hole transport layer to form an electron blocking layer having a thickness of 300 Å.

Subsequently, H-H1 and H-E43 (as hosts) and Compound 1 (as a dopant) were co-deposited on the electron blocking layer at a weight ratio of 47.5:47.5:5 to form an emission layer having a thickness of 400 Å.

ET3 and ET-D1 were co-deposited at a volume ratio of 50:50 on the emission layer to form an electron transport layer having a thickness of 350 Å, ET-D1 was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 1,000 Å, thereby completing the manufacture of an organic light-emitting device.

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Examples 2 to 6 and Comparative Examples a, B, and C

Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that the compounds listed in Table 4 were used instead of Compound 1 as a dopant in the formation of an emission layer.

Evaluation Example 4: Evaluation of Characteristics of Organic Light-Emitting Device

A current voltmeter (Keithley 2400) and a luminescence meter (Minolta Cs-1000A) were used on the organic light-emitting devices of Examples 1 to 6 and Comparative Examples A, B, and C to measure the driving voltage, luminescence efficiency (cd/A), and a quantum emission yield (%). The results thereof are shown in Table 4. The luminescence efficiency is shown in a relative value.

TABLE 4

Luminescence
Maximum

Dopant
Driving
efficiency
quantum

Compound
voltage
(relative
emmision yield

No.
(V)
value, %)
(%)

Example 1
1
4.01
104
108

Example 2
3
4.02
110
112

Example 3
177
4.05
106
107

Example 4
187
4.04
109
108

Example 5
218
4.01
104
104

Example 6
246
4.02
105
107

Comparative
A
4.30
87
84

Example A

Comparative
B
4.40
77
75

Example B

Comparative
C
4.57
74
97

Example C

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Referring to the results of Table 4, the organic light-emitting devices of Examples 1 to 6 were found to have excellent driving voltage, excellent luminescence efficiency, and improved quantum emission yield, as compared with the organic light-emitting devices of Comparative Examples A, B, and C.

As apparent from the foregoing description, the organometallic compound has excellent electrical characteristics and thermal stability. Accordingly, an organic light-emitting device including the organometallic compound may have an improved driving voltage, improved luminescence efficiency, and improved external quantum emission yield. Therefore, a high-quality electronic apparatus may be realized by using the organic light-emitting device.

It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.

Number	Date	Country	Kind
10-2021-0046891	Apr 2020	KR	national
10-2020-0045374	Apr 2020	KR	national

ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING ORGANOMETALLIC COMPOUND, AND ELECTRONIC APPARATUS INCLUDING ORGANIC LIGHT-EMITTING DEVICE

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