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

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to Korean Patent Application No. 10-2017-0063625, filed on May 23, 2017, in the Korean Intellectual Property Office, and all the benefits accruing therefrom under 35 U.S.C. § 119, the content of which is incorporated herein in its entirety by reference.

BACKGROUND
1. Field

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

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emission devices, which have superior characteristics in terms of a viewing angle, a response time, a brightness, a driving voltage, and a response speed, and which produce full-color images.

In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode. Holes provided from the 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. These excitons transit from an excited state to a ground state, thereby generating light.

Meanwhile, luminescent compounds may be used to monitor, sense, or detect a variety of biological materials including cells and proteins. An example of the luminescent compounds includes a phosphorescent luminescent compound.

Various types of organic light emitting devices are known. However, there still remains a need in OLEDs having low driving voltage, high efficiency, high brightness, and long lifespan.

SUMMARY

Aspects of the present disclosure provide an organometallic compound, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound.

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.

An aspect of the present disclosure provides an organometallic compound represented by Formula 1:

embedded image

M in Formula 1 may be beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au), in Formula 1, two bonds selected from a bond between A₁and M, a bond between A₂and M, a bond A₃and M, and a bond between A₄and M may each be a covalent bond, and the others thereof may each be a coordinate bond,

A₂in Formula 1 may be ring CY₂represented by one of Formulae A2-1 to A2-3, and in Formulae A2-1 to A2-3, * indicates a binding site to M in Formula 1, *′ indicates a binding site to T₁in Formula 1, and *″ indicates a binding site to T₂in Formula 1,

A₃in Formula 1 may be ring CY₃represented by one of Formulae A3-1 to A3-3, and in Formulae A3-1 to A3-3, * indicates a binding site to M in Formula 1, *″ indicates a binding site to T₂in Formula 1, and *′ indicates a binding site to T₃in Formula 1,

A₄in Formula 1 may be a first atom linked to M, or a non-cyclic moiety including the first atom linked to M,

the first atom may be B, P, Si, O, or S,

X₁to X₃and Y₁to Y₆in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3 may each independently be C or N,

rings CY₁to CY₃in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3 may each independently be a C₅-C₃₀carbocyclic group or a C₁-C₃₀heterocyclic group,

R₇and R₈may optionally be linked via a single bond, a double bond, or a first linking group to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

R₁to R₃, R₇, and R₈may each independently be selected from 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), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q₉),

a1 to a3 in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3 may each independently be an integer from 0 to 20,

two of a plurality of neighboring groups R₁may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

two of a plurality of neighboring groups R₂may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

two of a plurality of neighboring groups R₃may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

two or more groups selected from R₁to R₃may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

A₁and A₄in Formula 1 are not linked to each other, Formula 1 satisfies at least one of a “First Condition” to a “Third Condition”:

“First Condition”

A₁in Formula 1 is represented by Formula A1-2,

“Second Condition”

A₂in Formula 1 is represented by Formula A2-2 or A2-3, and

“Third Condition”

A3 in Formula 1 is represented by Formula A3-2 or A3-3,

at least one 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 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 may be selected from:

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, and a C₁-C₆₀alkoxy group;

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₆₀alkoxy group, each substituted with at least one selected from 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), —B(Q₁₆)(Q₁₇), and —P(═O)(Q₁₈)(Q₁₉);

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, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from 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 heterocycloalkenyl 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), —B(Q₂₆)(Q₂₇), and —P(═O)(Q₂₈)(Q₂₉); and

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

Q₁to Q₉, Q₁₁to Q₁₉, Q₂₁to Q₂₉, and Q₃₁to Q₃₉may each independently be selected from 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, a C₁-C₆₀alkyl group substituted with at least one elected from deuterium, a C₁-C₆₀alkyl group, and a C₆-C₆₀aryl 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-C₆₀aryl group substituted with at least one deuterium, a C₁-C₆₀akyl group, and a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

Another aspect of the present disclosure provides an organic light-emitting device including:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode

wherein the organic layer includes an emission layer and at least one of the above organometallic compounds.

The organometallic compounds may act as a dopant in the organic layer.

Another aspect of the present disclosure provides a diagnostic composition including at least one organometallic compound represented by Formula 1.

BRIEF DESCRIPTION OF THE DRAWING

These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the FIGURE which is a schematic view of an organic light-emitting device according to an 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 of the present description. 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 in contact with 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 of the present embodiments.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.

The term “or” means “and/or.” 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.

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

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.

“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%, 5% of the stated value.

An organometallic compound according to an embodiment is represented by Formula 1 below:

embedded image

In an embodiment, M may be Pd or Pt, but embodiments of the present disclosure are not limited thereto.

In Formula 1, two bonds selected from a bond between A₁and M, a bond between A₂and M, a bond between A₃and M, and a bond between A₄and M may each be a covalent bond, and the other bonds may each be a coordinate bond. Therefore, the organometallic compound represented by Formula 1 may be electrically neutral.

In an embodiment, a bond between A₁and M and a bond between A₄and M may each be a covalent bond, and a bond between A₂and M and a bond between A₃and M may each be a coordinate bond.

A₁in Formula 1 may be ring CY₁represented by Formula A1-1 or A1-2, and in Formulae A1-1 and A1-2, * indicates a binding site to M in Formula 1, and *′ indicates a binding site to T₁in Formula 1; A₂in Formula 1 may be ring CY₂represented by one of Formulae A2-1 to A2-3, and in Formulae A2-1 to A2-3, * indicates a binding site to M in Formula 1, *′ indicates a binding site to T₁in Formula 1, and *″ indicates a binding site to T₂in Formula 1; A₃in Formula 1 may be ring CY₃represented by one of Formulae A3-1 to A3-3, and in Formulae A3-1 to A3-3, * indicates a binding site M in Formula 1, *″ indicates a binding site to T₂in Formula 1, and *′ indicates a binding site to T₃in Formula 1; and A₄in Formula 1 may be a first atom linked to M, or a non-cyclic moiety including the first atom linked to M:

embedded image

The first atom may be, for example, B, P, Si, O, or S, but embodiments of the present disclosure are not limited thereto.

In an embodiment, the first atom may be O, but embodiments of the present disclosure are not limited thereto.

X₁to X₃and Y₁to Y₆in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3 may each independently be C or N.

For example, X₁to X₃in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3 may each be N, but embodiments of the present disclosure are not limited thereto.

Rings CY₁to CY₃in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3 may each independently be a C₅-C₃₀carbocyclic group or a C₁-C₃₀heterocyclic group.

For example, rings CY₁to CY₃may each independently be selected from 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 1,2,3,4-tetrahydronaphthalene 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 isoxazole 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, a 5,6,7,8-tetrahydroquinoline group, and a benzocarbazole group.

In one or more embodiments, rings CY₁to CY₃may each independently be i) a 5-membered ring, ii) a 6-membered ring, iii) a condensed ring with two or more 6-membered rings, or iv) a condensed ring with at least one 5-membered ring and at least one 6-membered ring; the 5-membered ring may be selected from a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, and a triazasilole group; and the 6-membered ring may be selected from a cyclohexane group, a cyclohexene group, an admantane group, a norbornane group, a norbornene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group.

In an embodiment, at least one of rings CY₁to CY₃may be a condensed ring with two or more 6-membered rings or a condensed ring with at least one 5-membered ring and at least one 6-membered ring. The 5-membered ring and the 6-membered ring are the same as described above.

In an embodiment, when A₁is the condensed ring with at least one 5-membered ring and at least one 6-membered ring, the 5-membered ring in the condensed ring may be linked to T₁in Formula 1.

In one or more embodiments, when A₁is the condensed ring with at least one 5-membered ring and at least one 6-membered ring, the 6-membered ring in the condensed ring may be linked to T₁in Formula 1.

In one or more embodiments, when A2 is the condensed ring with at least one 5-membered ring and at least one 6-membered ring, the 5-membered ring in the condensed ring may be linked to T₁in Formula 1.

In one or more embodiments, when A2 is the condensed ring with at least one 5-membered ring and at least one 6-membered ring, the 6-membered ring in the condensed ring may be linked to T₁in Formula 1.

The non-cyclic moiety including the first atom linked to M may be *—B(R₄₁)—*′, P(R₄₁)—*′, *—Si(R₄₁)(R₄₂)—*′, *—B(R₄₁)—C(═O)—*′, *—P(R₄₁)—C(═O)—*′, *—Si(R₄₁)(R₄₂)—C(═O)—*′, *—O—C(═O)—*′, or *—S—C(═O)—*′ (wherein R₄₁and R₄₂are the same as described in connection with R₄, * indicates a binding site to M in Formula 1, and *′ indicates a binding site to T₃in Formula 1), but embodiments of the present disclosure are not limited thereto.

T₁to T₃in Formula 1 may each independently be selected from a single bond, a double bond, *—N(R₇)—*′, *—B(R₇)—*′, *—P(R₇)—*′, *—C(R₇)(R₈)—*′, *—Si(R₇)(R₈)—*′, *—Ge(R₇)(R₈)—*—S—*′, *—Se—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*′, *—C(R₇)═*′, *═C(R₇)—*′, *—C(R₇)═C(R₈)—*′, *—C(═S)—*′, and *—C≡C—*′. * and *′ each indicate a binding site to a neighboring atom. R₇and R₈are the same as described above, and R₇and R₈may optionally be linked via a single bond, a double bond, or a first linking group to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group.

The first linking group may be selected from *—N(R₉)—*′, *—B(R₉)—*′, *—P(R₉)—*′, *—C(R₉)(R₁₀)—*′, *—Si(R₉)(R₁₀)—*′, *—Ge(R₉)(R₁₀)—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*′, *—C(R₉)═*′, *═C(R₉)—*′, *—C(R₉)═C(R₁₀)—*′, *—C(═S)—*′, and *—C≡C—*′, R₉and R₁₀are the same as described in connection with R₇, and * and *′ each indicate a binding site to a neighboring atom.

In an embodiment, T₁and T₂may each be a single bond.

R₁to R₃, R₇, and R₈may each independently be selected from 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), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q₉).

For example, R₁to R₃, R₇, and R₈may each independently be selected from:

a C₁-C₂₀alkyl group and a C₁-C₂₀alkoxy group, each substituted with at least one selected from 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-C₁₀alkyl 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 phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl 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 phenyl 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, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from 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 phenyl 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, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅); and

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

Q₁to Q₉and Q₃₃to Q₃₅may each independently be selected from:

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

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, a C₁-C₁₀alkyl group, and a phenyl group.

In an embodiment, R₁to R₃, R₇, and R₈may each independently be selected from hydrogen, deuterium, —F, a cyano group, a nitro group, —SF₅, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, groups represented by Formulae 9-1 to 9-19, groups represented by Formulae 10-1 to 10-156, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q₉) (wherein Q1 to Q9 are the same as described herein), but embodiments of the present disclosure are not limited thereto:

embedded image

In Formulae 9-1 to 9-19 and 10-1 to 10-156, “Ph” indicates a phenyl group, “TMS” indicates a trimethylsilyl group, and “*” indicates a binding site to a neighboring atom.

a1, a2, and a3 in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3 respectively indicate the number of groups R₁, the number of groups R₂, and the number of groups R₃, and may each independently be an integer from 0 to 20 (for example, 0, 1, 2, 3, or 4). When a1 is two or more, two or more groups R₁may be identical to or different from each other, when a2 is two or more, two or more groups R₂may be identical to or different from each other, and when a3 is two or more, two or more groups R₃may be identical to or different from each other.

i) Two of a plurality of neighboring groups R₁in Formulae A1-1 and A1-2 may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, ii) two of a plurality of neighboring groups R₂in Formulae A2-1 to A2-3 may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, iii) two of a plurality of neighboring groups R₃in Formulae A3-1 to A3-3 may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, and iv) two or more groups selected from R₁to R₃in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3 may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group.

For example, i) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two of a plurality of neighboring groups R₁in Formulae A1-1 and A1-2, ii) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two of a plurality of neighboring groups R₂in Formulae A2-1 to A2-3, iii) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two of a plurality of neighboring groups R₃in Formulae A3-1 to A3-3, and iv) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two neighboring groups selected from R₁to R₃in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3 may each independently be selected from:

a pentadiene group, a cyclohexane group, a cycloheptane group, an adamantane group, a bicycloheptane group, a bicyclo-octane group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a naphthalene group, an anthracene group, a tetracene group, a phenanthrene group, a dihydronaphthalene group, a phenalene group, a benzothiophene group, a benzofuran group, an indene group, an indole group, a benzosilole group, an azabenzothiophene group, an azabenzofuran group, an azaindene group, an azaindole group, and an azabenzosilole group;

but embodiments of the present disclosure are not limited thereto.

R_10ais the same as described in connection with R₁.

“An azabenzothiophene group, an azabenzofuran group, an azaindene group, an azaindole group, an azabenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, an azafluorene group, an azacarbazole group, and an azadibenzosilole group” as used herein mean heteroatom-containing rings that respectively have the same structure as “a benzothiophene group, a benzofuran group, an indene group, an indole group, an benzosilole group, a dibenzothiophene group, a dibenzofuran group, a fluorene group, a carbazole group, and a dibenzosilole group”, except that at least one of carbons forming the rings thereof is substituted with nitrogen.

A₁and A₄in Formula 1 are not linked to each other. That is, the organometallic compound represented by Formula 1 may have three cyclometallated rings sharing M with one another.

Formula 1 satisfies at least one of a “First Condition” to a “Third Condition” below:

“First Condition”

A₁in Formula 1 is represented by Formula A1-2,

“Second Condition”

A₂in Formula 1 is represented by Formula A2-2 or A2-3, and

“Third Condition”

A₃in Formula 1 is represented by Formula A3-2 or A3-3.

For example, Formula 1 may satisfy the “First Condition” and the “Second Condition”.

In an embodiment, Formula 1 may satisfy all of the “First Condition” to the “Third Condition”.

In an embodiment, A₁in Formula 1 may be represented by one of Formulae A1-1(1) to A1-1(26) and A1-2(1) to A1-2(74):

embedded image

In Formulae A1-1(1) to A1-1(26) and A1-2(1) to A1-2(74),

X₁and R₁are each independently the same as described herein,

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

X₁₃may be N or C(R₁₃),

X₁₄may be N or C(R₁₄),

R₁₁to R₁₈are each independently the same as described in connection with R₁,

a17 may be an integer from 0 to 7,

a16 may be an integer from 0 to 6,

a15 may be an integer from 0 to 5,

a14 may be an integer from 0 to 4,

a13 may be an integer from 0 to 3,

a12 may be an integer from 0 to 2,

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

*′ indicates a binding site to T₁in Formula 1.

In one or more embodiments, A₂in Formula 1 may be represented by one of Formulae A2-1(1) to A2-1(17), A2-2(1) to A2-2(58), and A2-3(1) to A2-3(58):

embedded image

In Formulae A2-1(1) to A2-1(17), A2-2(1) to A2-2(58), and A2-3(1) to A2-3(58),

X₂and R₂are each independently the same as described herein,

X₂₁may be O, S, N(R₂₁), C(R₂₁)(R₂₂), or Si(R₂₁)(R₂₂),

X₂₃may be N or C(R₂₃),

X₂₄may be N or C(R₂₄),

R₂₁to R₂₈are each independently the same as described in connection with R₂,

a26 may be an integer from 0 to 6,

a25 may be an integer from 0 to 5,

a24 may be an integer from 0 to 4,

a23 may be an integer from 0 to 3,

a22 may be an integer from 0 to 2,

* indicates a binding site to M in Formula 1,

*′ indicates a binding site to T₁in Formula 1, and

*″ indicates a binding site to T₂in Formula 1.

In one or more embodiments, A₃in Formula 1 may be represented by one of Formulae A3-1(1) to A3-1(21), A3-2(1) to A3-2(58), and A3-3(1) to A3-3(58):

embedded image

In Formulae A3-1(1) to A3-1(21), A3-2(1) to A3-2(58), and A3-3(1) to A3-3(58),

X₃and R₃are each independently the same as described herein,

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

X₃₃may be N or C(R₃₃),

X₃₄may be N or C(R₃₄),

R₃₁to R₃₈are each independently the same as described in connection with R₃,

a36 may be an integer from 0 to 6,

a35 may be an integer from 0 to 5,

a34 may be an integer from 0 to 4,

a33 may be an integer from 0 to 3,

a32 may be an integer from 0 to 2,

* indicates a binding site to M in Formula 1,

*′ indicates a binding site to T₂in Formula 1, and

*″ indicates a binding site to T₃in Formula 1.

In one or more embodiments,

i) A₄may be *—O—*′ or *—S—*′, and T₃may be *—N(R₇)—*′, *—B(R₇)—*′, *—C(R₇)(R₈)—*′, *—Si(R₇)(R₈)—*′, *—Ge(R₇)(R₈)—*′, or *—C(═O)—*′;

ii) A₄may be represented by one of Formulae 4(1) to 4(5), and T₃may be a single bond, or

iii) A₄may be *—O—*′, or *—S—*′, and T₃may be a single bond, but embodiments of the present disclosure are not limited thereto:

embedded image

In Formulae A4(1) to A4(5),

R₄₁and R₄₂are each independently the same as described in connection with R₁,

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

*′ indicates a binding site to T₃in Formula 1.

In one or more embodiments,

A₁in Formula 1 may be represented by one of Formulae CY1-1 to CY1-11, and/or

A₂in Formula 1 may be represented by one of Formulae CY2-1 to CY2-5, and/or

A₃in Formula 1 may be represented by one of Formulae CY3-1 to CY3-10:

embedded image

In Formulae CY1-1 to CY1-11, CY2-1 to CY2-5, and CY3-1 to CY3-10,

X₂, X₃, and R₁to R₃are each independently the same as described herein,

R_1aand R_1bare each independently the same as described in connection with R₁,

X₂₁may be O, S, N(R₂₁), C(R₂₁)(R₂₂), or Si(R₂₁)(R₂₂),

R_2a, R_2b, R₂₁, and R₂₂are each independently the same as described in connection with R₂,

R_3aand R_3bare each independently the same as described in connection with R₃,

in Formulae CY1-1 to CY1-5, * indicates a binding site to M in Formula 1, and *′ indicates a binding site to T₁in Formula 1,

in Formulae CY2-1 to CY2-5, * indicates a binding site to M in Formula 1, *′ indicates a binding site to T₁in Formula 1, and *″ indicates a binding site to T₂in Formula 1, and

in Formulae CY3-1 to CY3-6, * indicates a binding site to M in Formula 1, *′ indicates a binding site to T₂in Formula 1, and *″ indicates a binding site to T₃in Formula 1.

In one or more embodiments, in Formula 1, A₁may be represented by Formula A1-2, and A₂may be represented by Formula A2-2.

In one or more embodiments, in Formula 1,

i) A₃may be represented by Formula A3-1, A₄may be *—O—*′ or *—S—*′, and T₃may be *—N(R₇)—*′, *—B(R₇)—*′, *—P(R₇)—*′, *—C(R₇)(R₈)—*′, *—Si(R₇)(R₈)—*′, *—Ge(R₇)(R₈)—*′, or

ii) A₃may be represented by Formula A3-1, A₄may be represented by one of Formulae 4(1) to 4(5), and T₃may be a single bond, or

iii) A₃may be represented by Formula A3-2, A₄may be *—O—*′, or *—S—*′, and T₃may be a single bond, but embodiments of the present disclosure are not limited thereto.

For example, the organometallic compound represented by Formula 1 may be one of Compounds 1 to 125:

embedded image

embedded image

A₄in Formula 1 may be a first atom linked to M, or a non-cyclic moiety including the first atom linked to M, provided that the first atom is B, P, Si, O, or S. Since a moiety contributing to the lowest unoccupied molecular orbital (LUMO) energy level in Formula 1 is non-aromatic, it is possible to improve electron transport characteristics of a moiety contributing to the highest occupied molecular orbital (HOMO) energy level in Formula 1. Thus, electron donating capability of the organometallic compound may be improved. Therefore, luminescent efficiency of an electronic device, for example, an organic light-emitting device, which includes the organometallic compound, may be improved, and an emission wavelength thereof may be easily controlled (for example, an emission wavelength of red light or green light may be obtained).

Also, as described above, Formula 1 satisfies at least one of the “First Condition” to the “Third Condition”, and thus, thermal stability and electron donating capability of the organometallic compound may be improved by introducing a bicyclic group having a robust structure into the moiety contributing to the HOMO energy level in Formula 1. Therefore, the lifespan of an electronic device, for example, an organic light-emitting device, which includes the organometallic compound, may be improved, and an emission wavelength thereof may be easily controlled (for example, an emission wavelength of red light or green light may be obtained).

For example, HOMO, LUMO, energy band gap (E_g), singlet (S₁), and triplet (T₁) energy levels of some of Compounds illustrated above and Compound A were evaluated by using a DFT method of Gaussian program (structurally optimized at a level of B3LYP, 6-31 G(d,p)).

TABLE 1

Compound
HOMO

Eg energy
S₁energy
T₁energy

No.
(eV)
LUMO (eV)
level (eV)
level (eV)
level (eV)

1
−4.743
−2.238
2.505
2.155
1.748

16
−4.661
−2.245
2.416
2.081
1.703

31
−.4.739
−2.188
2.547
2.193
1.745

46
−4.735
−2.139
2.596
2.231
1.743

121
−4.504
−2.156
2.348
2.004
1.621

A
−4.482
−2.342
2.140
2.214
1.598

embedded image

From Table 1, it is confirmed that the organometallic compound represented by Formula 1 has such electrical characteristics that are suitable for use in an electronic device, for example, for use as a dopant for an organic light-emitting device.

Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples provided below.

The organometallic compound represented by Formula 1 is suitable for use in an organic layer of an organic light-emitting device, for example, for use as a dopant in an emission layer of the organic layer. Thus, another aspect of the present disclosure provides an organic light-emitting device that includes:

a first electrode;

a second electrode; and

an organic layer that is disposed between the first electrode and the second electrode,

wherein the organic layer includes an emission layer and at least one organometallic compound represented by Formula 1.

The organic light-emitting device may have, due to the inclusion of an organic layer including the organometallic compound represented by Formula 1, a low driving voltage, high efficiency, high power, high quantum efficiency, a long lifespan, a low roll-off ratio, and excellent color purity.

The organometallic compound of Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1 is smaller than an amount of the host).

The expression “(an organic layer) includes at least one of organometallic compounds” as used herein may include an embodiment in which “(an organic layer) includes identical organometallic compounds represented by Formula 1” and an embodiment in which “(an organic layer) includes two or more different organometallic compounds represented by Formula 1.”

For example, the organic layer may include, as the organometallic compound, only Compound 1. In this regard, Compound 1 may be included in an emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be included in an identical layer (for example, Compound 1 and Compound 2 all may be included in an 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; or 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.

In an embodiment, in the organic light-emitting device, the first electrode is an anode, the second electrode is a cathode, and the organic layer further includes a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode, wherein the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and wherein the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

The term “organic layer” as used herein refers to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of the organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.

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

A substrate may be additionally disposed under the first electrode 11 or above the second electrode 19. As the substrate, any substrate that is used in general organic light-emitting devices may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials with a high work function to facilitate 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 may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), and zinc oxide (ZnO). In one or more embodiments, magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the first electrode.

The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.

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

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

The hole transport region may be disposed 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 any combination thereof.

The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, which are sequentially stacked in this stated order from the first electrode 11.

A hole injection layer may be formed on the first electrode 11 by using one or more suitable methods selected from vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) deposition.

When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on a compound that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10⁻⁸torr to about 10⁻³torr, and a deposition rate of about 0.01 Angstroms per second (Å/sec) to about 100 Å/sec. However, the deposition conditions are not limited thereto.

When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

Conditions for forming a hole transport layer and an electron blocking layer may be understood by referring to conditions for forming the hole injection layer.

The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzene sulfonic acid (PAN I/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PAN I/CSA), polyaniline/poly(4-styrene sulfonate) (PANI/PSS), a compound represented by Formula 201 below, and a compound represented by Formula 202 below:

embedded image

Ar₁₀₁and Ar₁₀₂in Formula 201 may each independently be selected from:

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, and a pentacenylene group, each substituted with at least one selected from 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, and a monovalent non-aromatic condensed heteropolycyclic group.

xa and xb in Formula 201 may each independently be an integer from 0 to 5, or may each independently be 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.

R₁₀₁to R₁₀₈, R₁₁₁to R₁₁₉, and R₁₂₁to R₁₂₄in Formulae 201 and 202 may each independently be selected from:

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 (for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and so on), and a C₁-C₁₀alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and so on);

a C₁-C₁₀alkyl group and a C₁-C₁₀alkoxy group, each substituted with at least one selected from 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, and a phosphoric acid group or a salt thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group, each substituted with at least one selected from 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, and a C₁-C₁₀alkoxy group,

but embodiments of the present disclosure are not limited thereto.

R₁₀₉in Formula 201 may be selected from:

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group, each substituted with at least one selected from 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 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group.

In an embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments of the present disclosure are not limited thereto:

embedded image

R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉in Formula 201A may be understood by referring to the description provided herein.

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

embedded image

A 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 1,000 Å. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and 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. While not wishing to be bound by theory, it is understood that when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.

The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.

The charge-generation material may be, for example, a p-dopant. The p-dopant may be one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenium oxide; and a cyano group-containing compound, such as Compound HT-D1 below, but are not limited thereto.

embedded image

The hole transport region may include a buffer layer.

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

Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer although the deposition or coating conditions may vary according to a compound that is used to form the emission layer.

Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be selected from materials for the hole transport region described above and materials for a host to be explained later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be mCP, which will be explained later.

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

The host may include at least one selected from TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, and Compound H51:

embedded image

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

embedded image

Ar₁₁₁and Ar₁₁₂in Formula 301 may each independently be selected from:

a phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group; and

a phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group, each substituted with at least one selected from a phenyl group, a naphthyl group, and an anthracenyl group.

Ar₁₁₃to Ar₁₁₆in Formula 301 may each independently be selected from:

a C₁-C₁₀alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenyl group; and

a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenyl group, each substituted with at least one selected from a phenyl group, a naphthyl group, and an anthracenyl group.

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

Ar₁₁₃to Ar₁₁₆in Formula 301 may each independently be selected from:

a C₁-C₁₀alkyl group substituted with at least one selected from a phenyl group, a naphthyl group, and an anthracenyl group;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group, each substituted with at least one selected from 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 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group; and

embedded image

but embodiments of the present disclosure are not limited thereto.

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

embedded image

Ar₁₂₂to Ar₁₂₅in Formula 302 are the same as described in detail in connection with Ar₁₁₃in Formula 301.

Ar₁₂₆and Ar₁₂₇in Formula 302 may each independently be a C₁-C₁₀alkyl group (for example, a methyl group, an ethyl group, or a propyl group).

k and l in Formula 302 may each independently be an integer from 0 to 4. For example, k and l may be 0, 1, or 2.

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

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

A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. While not wishing to be bound by theory, it is understood that when the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.

Then, an electron transport region may be disposed on the emission layer.

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

For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to 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, and BAlq but embodiments of the present disclosure are not limited thereto.

embedded image

A 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 300 Å. While not wishing to be bound by theory, it is understood that when the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have improved hole blocking ability without a substantial increase in driving voltage.

The electron transport layer may further include at least one selected from BCP, Bphen, Alq₃, BAlq, TAZ, and NTAZ.

embedded image

In one or more embodiments, the electron transport layer may include at least one of ET1 and ET25, but are not limited thereto:

embedded image

A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.

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

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

embedded image

The electron transport region may include an electron injection layer that promotes flow of electrons from the second electrode 19 thereinto.

The electron injection layer may include at least one selected from LiF, NaCl, CsF, Li₂O, and BaO.

A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.

The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be selected from metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as a material for forming the second electrode 19. In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

Hereinbefore, the organic light-emitting device has been described with reference to FIG. 1, but embodiments of the present disclosure are not limited thereto.

Another aspect of the present disclosure provides a diagnostic composition including at least one organometallic compound represented by Formula 1.

The organometallic compound represented by Formula 1 provides high luminescent efficiency. Accordingly, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.

The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and 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 non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. The term “C₁-C₆₀alkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₆₀alkyl group.

The term “C₁-C₆₀alkoxy group” as used herein refers to a monovalent group represented by —OA₁₀₁(wherein A₁₀₁is the C₁-C₆₀alkyl group), and non-limiting examples thereof include a methoxy group, an ethoxy group, and an iso-propyloxy group.

The term “C₂-C₆₀alkenyl group” as used herein refers to a hydrocarbon group formed by including at least one carbon-carbon double bond in the middle or at the terminus of the C₂-C₆₀alkyl group, and 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 hydrocarbon group formed by including at least one carbon-carbon triple bond in the middle or at the terminus of the C₂-C₆₀alkyl group, and 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 monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C₃-C₁₀cycloalkylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀cycloalkyl group.

The term “C₁-C₁₀heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C₁-C₁₀heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and that has no aromaticity, and non-limiting 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 that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C₁-C₁₀heterocycloalkenyl group are 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, and the term “C₆-C₆₀arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting 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 two or more rings, the rings may be fused to each other.

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and 1 to 60 carbon atoms. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, P, and S as a ring-forming atom, and 1 to 60 carbon atoms. Non-limiting 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 two or more rings, the rings may be fused to each other.

The term “C₆-C₆₀aryloxy group” as used herein indicates —OA₁₀₂(wherein A₁₀₂is the C₆-C₆₀aryl group), and a C₆-C₆₀arylthio group as used herein indicates —SA₁₀₃(wherein A103 is the C₆-C₆₀aryl group).

The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. 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 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 (for example, having 2 to 60 carbon atoms) having two or more rings condensed to each other, a heteroatom selected from N, O, P, Si, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Non-limiting 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 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 having, as a ring-forming atom, 5 to 30 carbon atoms only. The C₅-C₃₀carbocyclic group may be a monocyclic group or a polycyclic group.

The term “C₁-C₃₀heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S other than 1 to 30 carbon atoms. The C₁-C₃₀heterocyclic group may be a monocyclic group or a polycyclic group.

At least one substituent of the substituted C₅-C₃₀carbocyclic group, the substituted C₂-C₃₀heterocyclic group, the substituted C₅-C₃₀alkyl 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 may be selected from:

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-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group;

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group, each substituted with at least one selected from 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 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), —B(Q₁₆)(Q₁₇), and —P(═O)(Q₁₈)(Q₁₉);

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, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from 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-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), —B(Q₂₆)(Q₂₇), and —P(═O)(Q₂₈)(Q₂₉); and

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

Q₁to Q₉, Q₁₁to Q₁₉, Q₂₁to Q₂₉, and Q₃₁to Q₃₉may each independently be selected from 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-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-C₆₀aryl group substituted with at least one selected from a C₁-C₆₀alkyl group and a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

When a group containing a specified number of carbon atoms is substituted with any of the groups listed in the preceding paragraph, the number of carbon atoms in the resulting “substituted” group is defined as the sum of the carbon atoms contained in the original (unsubstituted) group and the carbon atoms (if any) contained in the substituent. For example, when the term “substituted C₁-C₃₀alkyl” refers to a C₁-C₃₀alkyl group substituted with C₆-C₃₀aryl group, the total number of carbon atoms in the resulting aryl substituted alkyl group is C₇-C₆₀.

Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Example and Examples. However, the organic light-emitting device is not limited thereto. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of A used was identical to an amount of B used, in terms of a molar equivalent.

EXAMPLES
Synthesis Example 1
Synthesis of Compound 1

embedded image

Synthesis of Intermediate 1-1

10.00 grams (g) (18.20 millimoles, mmol) of the starting material 1a (1-(4-bromo-1-phenyl-1H-benzo[d]imidazole-2-yl)-3,6-di-tert-butyl-9H-carbazole), 8.00 g (36.30 mmol) of di-tert-butyl dicarbonate, 4.40 g (36.30 mmol) of 4-dimethylaminopyridine, and 50 milliliters (mL) of triethylamine were added to a 500-mL round-bottom flask with a stirrer in a nitrogen atmosphere, and heated under reflux for 24 hours. After the reaction was completed, the organic layer was extracted with 400 mL of dichloromethane, washed with a NaCl aqueous solution (100 mL×2), dried with MgSO₄, and filtered. The solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (ethyl acetate/hexane=1:10) to obtain 11.5 g (yield: 99%) of Intermediate 1-1. The obtained compound was identified by LC-MS.

LC-MS m/z=651.65 (M+H)⁺.

Synthesis of Intermediate 1-2

14.0 g (21.5 mmol) of Intermediate 1-1 (tert-butyl 1-(4-bromo-1-phenyl-1H-benzo[d]imidazole-2-yl)-3,6-di-tert-butyl-9H-carbazole-9-carboxylate) and 8.2 g (32.3 mmol) of bis(pinacolato)diboron were added to a flask, and 500 mL of toluene was added thereto in a nitrogen atmosphere. Then, 1.0 g (1.2 mmol) of PdCl₂(dppf) and 6.3 g (64.6 mmol) of KOAc were sequentially added thereto, and the reaction mixture was stirred at a temperature of 110° C. for 24 hours. After the reaction was completed, the reaction product was cooled to room temperature, and toluene was distilled off under reduced pressure. Then, 500 mL of ethyl acetate was added to the residue. The organic layer obtained therefrom was washed with a saturated NaHCO₃aqueous solution (150 mL×2) and a saturated NaCl aqueous solution (100 mL×2), dried with MgSO₄, and filtered. The solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (ethyl acetate/hexane=1:20) to obtain 5.0 g (yield: 33%) of Intermediate 1-2. The obtained compound was identified by LC-MS.

LC-MS m/z=698.71 (M+H)⁺.

Synthesis of Intermediate 1-3

5.3 g (7.64 mmol) of Intermediate 1-2 (tert-butyl 3,6-di-tert-butyl-1-(1-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-benzo[d]imidazole-2-yl)-9H-carbazole-9-carboxylate) and 1.5 g (6.94 mmol) of methyl 6-bromopicolinate were added to a flask, and 150 ml of a mixed solvent of tetrahydrofuran/distilled water (4:1) was added thereto in a nitrogen atmosphere. Then, 0.4 g (0.35 mmol) of tetrakis(triphenylphospine)palladium(0) and 2.21 g (20.83 mmol) of potassium carbonate were sequentially added thereto, and the reaction mixture was stirred at a temperature of 110° C. for 24 hours. After the reaction was completed, the reaction product was cooled to room temperature and 500 mL of ethyl acetate was added thereto. The organic layer obtained therefrom was washed with a saturated NaHCO₃aqueous solution (150 mL×2) and a saturated NaCl aqueous solution (100 mL×2), dried with MgSO₄, and filtered. The solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (ethyl acetate/hexane=1:20) to obtain 2.3 g (yield: 47%) of Intermediate 1-3. The obtained compound was identified by LC-MS.

LC-MS m/z=707.87 (M+H)⁺.

Synthesis of Intermediate 1-4

3.5 g of Intermediate 1-3 (tert-butyl 3,6-di-tert-butyl-1-(4-(6-(methoxycarbonyl)pyridine-2-yl)-1-phenyl-1H-benzo[d]imidazole-2-yl)-9H-carbazole-9-carboxylate) was mixed with 20 mL of tetrahydrofuran at room temperature, and 0.2 g of lithium hydroxide mixed with 2 mL of distilled water were added thereto. The resulting mixture was stirred at room temperature for 5 hours. After the reaction was completed, 500 mL of ethyl acetate was added to the reaction product. The organic layer obtained therefrom was washed with a saturated NaHCO₃aqueous solution (150 mL×2) and a saturated NaCl aqueous solution (100 mL×2), dried with MgSO₄, and filtered. The solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (ethyl acetate/hexane=1:5) to obtain 3.3 g (yield: 99%) of Intermediate 1-4. The obtained compound was identified by LC-MS.

LC-MS m/z=693.84 (M+H)⁺.

Synthesis of Intermediate 1-5

3.0 g (23.3 mmol) of Intermediate 1-4 (6-(2-(9-(tert-butoxycarbonyl)-3,6-di-tert-butyl-9H-carbazole-1-yl)-1-phenyl-1H-benzo[d]imidazole-4-yl)picolinic acid) was mixed with 50 mL of dichloromethane, and 1.0 mL of trifluoroacetic acid was slowly added dropwise thereto. The resulting mixture was stirred at a temperature of 100° C. for 12 hours. After the reaction was completed, a distillation process was performed on the reaction product under reduced pressure to remove dichloromethane and trifluoroacetic acid therefrom, and 300 mL of ethyl acetate was added thereto. Then, a saturated NaHCO₃aqueous solution was added to an organic layer obtained therefrom until neutralized (pH=7 to 8), and the organic layer was separated therefrom. The obtained organic layer was washed with a saturated NaCl aqueous solution (100 mL×2), dried with MgSO₄, and filtered. The solvent was distilled off under reduced pressure to obtain 2.3 g (yield: 78%) of Intermediate 1-5. The obtained compound was identified by LC-MS.

LC-MS m/z=593.73 (M+H)⁺.

Synthesis of Compound 1

2.0 g (5.06 mmol) of Intermediate 1-5 (6-(2-(3,6-di-tert-butyl-9H-carbazole-1-yl)-1-phenyl-1H-benzo[d]imidazole-4-yl)picolinic acid) and 2.52 g (6.07 mmol) of K₂PtCl₄were mixed with 70 mL of a mixed solvent including 60 mL of AcOH and 10 mL of H₂O, and the resulting mixture was refluxed for 16 hours. The resulting mixture was cooled to room temperature, and a precipitate was filtered therefrom. The precipitate was dissolved again in methylene chloride (MC) and washed with H₂O. The crude product was purified by column chromatography (MC 30%, Hex 70%) to obtain 1.50 g (yield: 38%) of Compound 1. The obtained compound was identified by LC-MS.

LC-MS m/z=786.80 (M+H)⁺.

Synthesis Example 2
Synthesis of Compound 16

embedded image

1.1 g (yield: 41%) of Compound 16 was synthesized in the same manner as in Synthesis Example 1, except that the starting material 16a was used instead of the starting material 1a (1-(4-bromo-1-phenyl-1H-benzo[d]imidazole-2-yl)-3,6-di-tert-butyl-9H-carbazole) in synthesizing Intermediate 1-1. The obtained compound was identified by LC-MS.

LC-MS m/z=674.58 (M+H)⁺.

Synthesis Example 3
Synthesis of Compound 31

0.8 g (yield: 32%) of Compound 31 was synthesized in the same manner as in Synthesis Example 1, except that 2-bromoquinoline-8-ol was used instead of methyl 6-bromopicolinate in synthesizing Intermediate 1-3. The obtained compound was identified by LC-MS.

LC-MS m/z=808.85 (M+H)⁺.

Synthesis Example 4
Synthesis of Compound 46

1.0 g (yield: 35%) of Compound 46 was synthesized in the same manner as in Synthesis Example 1, except that the starting material 16a was used instead of the starting material 1a (1-(4-bromo-1-phenyl-1H-benzo[d]imidazole-2-yl)-3,6-di-tert-butyl-9H-carbazole) in synthesizing Intermediate 1-1, and 2-bromoquinoline-8-ol was used instead of methyl 6-bromopicolinate in synthesizing Intermediate 1-3. The obtained compound was identified by LC-MS.

LC-MS m/z=696.63 (M+H)⁺.

Synthesis Example 5
Synthesis of Compound 61

embedded image

0.7 g (yield: 30%) of Compound 61 was synthesized in the same manner as in Synthesis Example 1, except that the starting material 61a (4-bromo-2-(5-(tert-butyl)-1H-indole-7-yl)-1-phenyl-1H-benzo[d]imidazole) was used instead of the starting material 1a (1-(4-bromo-1-phenyl-1H-benzo[d]imidazole-2-yl)-3,6-di-tert-butyl-9H-carbazole) in synthesizing Intermediate 1-1. The obtained compound was identified by LC-MS.

LC-MS m/z=680.63 (M+H)⁺.

Synthesis Example 6
Synthesis of Compound 91

0.9 g (yield: 31%) of Compound 91 was synthesized in the same manner as in Synthesis Example 1, except that the starting material 61a (4-bromo-2-(5-(tert-butyl)-1H-indole-7-yl)-1-phenyl-1H-benzo[d]imidazole) was used instead of the starting material 1a (1-(4-bromo-1-phenyl-1H-benzo[d]imidazole-2-yl)-3,6-di-tert-butyl-9H-carbazole) in synthesizing Intermediate 1-1, and 2-bromoquinoline-8-ol was used instead of methyl 6-bromopicolinate in synthesizing Intermediate 1-3. The obtained compound was identified by LC-MS.

LC-MS m/z=702.68 (M+H)⁺.

Evaluation Example 1
Evaluation of Photoluminescence Quantum Yield (PLQY)

A CH₂Cl₂solution of polymethyl methacrylate (PMMA) and a mixture of 8 percent by weight (wt %) of CBP and Compound 1 (an amount of Compound 1 was 10 parts by weight based on 100 parts by weight of the mixture) were mixed. The resulting mixture was coated on a quartz substrate by using a spin coater, thermally treated at a temperature of 80° C. in an oven, and then coated to room temperature, thereby completing the manufacture of film 1.

The luminescence quantum yield of film 1 was evaluated by using a Hamamatsu Photonics absolute photoluminescence (PL) quantum yield measurement system equipped with a xenon light source, a monochromator, a photonic multichannel analyzer, and an integrating sphere, and photoluminescence quantum yield (PLQY) measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). It was confirmed from the evaluation result that the PLQY in film of Compound 1 was 0.998. Therefore, it is confirmed that Compound 1 has high PLQY in film.

Example 1

As an anode, a glass substrate, on which ITO/Ag/ITO were respectively deposited to thicknesses of 70 Angstroms (Å)/1,000 Å/70 Å, was cut to a size 50 mm×50 mm×0.5 mm (mm=millimeter), sonicated with iso-propyl alcohol and pure water each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the resulting glass substrate was provided to a vacuum deposition apparatus.

2-TNATA was deposited on the anode to form a hole injection layer having a thickness of 600 Å, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was deposited on the hole injection layer to form a hole transport layer having a thickness of 1,350 Å.

CBP (host) and Compound 1 (dopant) were co-deposited on the hole transport layer at a weight ratio of 94:6 to form an emission layer having a thickness of 400 Å, and BCP was deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å. Then, Alq₃was deposited on the hole blocking layer to form an electron transport layer having a thickness of 350 Å, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and MgAg was deposited on the electron injection layer at a weight ratio of 90:10 to form a cathode having a thickness of 120 Å, thereby completing the manufacture of an organic light-emitting device (emitting red light) having a structure of ITO/Ag/ITO/2-TNATA (600 Å)/NPB (1,350 Å)/CBP+Compound 1 (6 wt %) (400 Å)/BCP (50 Å)/Alq₃(350 Å)/LiF (10 Å)/MgAg (120 Å).

embedded image

Examples 2 to 5 and Comparative Example A

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

Evaluation Example 2
Evaluation of Characteristics of Organic Light-Emitting Devices

The driving voltage, luminescent efficiency, and PLQY of the organic light-emitting devices manufactured according to Examples 1 to 5 and Comparative Example A were evaluated, and evaluation results thereof are shown in Table 2. This evaluation was performed using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1,000A).

TABLE 2

Driving
Luminescent

voltage
efficiency

Dopant
(V)
(cd/A)
PLQY (%)

Example 1
Compound
4.892
17.34
14.85

1

Example 2
Compound
4.883
18.15
15.32

16

Example 3
Compound
5.001
19.88
17.24

46

Example 4
Compound
4.913
18.33
15.20

61

Example 5
Compound
5.000
18.92
15.92

91

Comparative
Compound
5.421
14.35
12.22

Example A
A

embedded image

Referring to Table 2, it is confirmed that the organic light-emitting devices of Examples 1 to 5 have excellent or equivalent driving voltage, luminescent efficiency, and PLQY characteristics, as compared with those of the organic light-emitting device of Comparative Example A.

As described above, the organometallic compounds according to the embodiments of the present disclosure have excellent electrical characteristics and thermal stability, and accordingly, organic light-emitting devices including such organometallic compounds may have excellent driving voltage, efficiency, power, color purity, and lifespan characteristics. Also, due to excellent phosphorescent luminescence characteristics, such organometallic compounds may provide a diagnostic composition having high diagnostic efficiency.

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 of the present disclosure as defined by the following claims.

Number	Name	Date	Kind
10147893	Lee	Dec 2018	B2
20100176380	Jung	Jul 2010	A1
20110028730	Könemann et al.	Feb 2011	A1
20120223634	Xia	Sep 2012	A1
20130274473	Che	Oct 2013	A1
20140135498	Fukuzaki	May 2014	A1
20150274762	Li et al.	Oct 2015	A1
20150349279	Li et al.	Dec 2015	A1
20160240800	Ma	Aug 2016	A1
20160301019	Lee	Oct 2016	A1
20180013078	Lee et al.	Jan 2018	A1
20180208615	Lin	Jul 2018	A1

Number	Date	Country
2010185068	Aug 2010	JP
03084960	Oct 2003	WO

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

Information

Patent Number

Date Filed

Date Issued

Inventors

Original Assignees

Examiners

Agents

CPC

Field of Search

CPC

International Classifications

Term Extension

Abstract

Description

Claims

Priority Claims (1)

US Referenced Citations (12)

Foreign Referenced Citations (2)

Related Publications (1)