LIGHT-EMITTING DEVICE, ELECTRONIC APPARATUS INCLUDING THE SAME, AND ORGANOMETALLIC COMPOUND

CROSS-REFERENCE TO RELATED APPLICATION(S)

This application claims priority to and benefits of Korean Patent Application No. 10-2022-0002348 under 35 U.S.C. § 119, filed on Jan. 6, 2022 in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

BACKGROUND
1. Technical Field

Embodiments relate to a light-emitting device, an electronic apparatus including the same, and an organometallic compound.

2. Description of the Related Art

In comparison to devices of the related art, light-emitting devices are self-emissive devices that have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of luminance, driving voltage, and response speed, and produce full-color images.

In an example, a light-emitting device may have a structure in which a first electrode is arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state, thereby generating light.

It is to be understood that this background of the technology section is, in part, intended to provide useful background for understanding the technology. However, this background of the technology section may also include ideas, concepts, or recognitions that were not part of what was known or appreciated by those skilled in the pertinent art prior to a corresponding effective filing date of the subject matter disclosed herein.

SUMMARY

Embodiments include an organometallic compound that may provide low driving voltage and high luminescence efficiency, a light-emitting device having low driving voltage and high luminescence efficiency, and an electronic apparatus including the 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 embodiments of the disclosure.

According to embodiments, provided is a light-emitting device which may include a first electrode, a second electrode facing the first electrode, an interlayer between the first electrode and the second electrode and including an emission layer, and an organometallic compound represented by Formula 1:

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In Formula 1,

M may be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),

X₁may be C,

X₂to X₄may each independently be C or N,

a bond between X₁and M may be a coordinate bond; one of a bond between X₂and M, a bond between X₃and M, and a bond between X₄and M may be a coordinate bond; and the remainder of X₂to X₄may each be a covalent bond,

rings CY₁, CY₂, CY₃, and CY₄may each independently be a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group,

X₅may be C,

ring CY₅may be: an X₅-containing 5-membered ring; or an X₅-containing 5-membered ring condensed with at least one 6-membered ring,

the X₅-containing 5-membered ring may be a pyrrole group, a furan group, a thiophene group, a pyrazole group, an imidazole group, an oxazole group, an iso-oxazole group, a thiazole group, or an isothiazole group,

the 6-membered ring which may be optionally condensed to the X₅-containing 5-membered ring may be a benzene group, a pyridine group, or a pyrimidine group,

X₅₁may be *—N—*′, *—B—*′, *—P—*′, *—C(R₆)—*′, *—Si(R₆)—*′, or *—Ge(R₆)—*′,

X₅₂may be a single bond, *—N(R₇)—*′, *—B(R₇)—*′, *—P(R₇)—*′, *—C(R₇)(R₈)—*′, *—Si(R₇)(R₈)—*′, *—Ge(R₇)(R₈)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*, *—C(R₇)═*′, *═C(R₇)—*′, *—C(R₇)═C(R₈)—*′, *—C(═S)—*′, or *—C≡C—*′,

L₁may be a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

b1 may be an integer from 1 to 5,

R₁to R₈and T₁may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group that is unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group that is unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group that is unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group that is unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryloxy group that is unsubstituted or substituted with at least one R_10a, a C₆-C₆₀arylthio group that is unsubstituted or substituted with at least one R_10a, a C₇-C₆₀aryl alkyl group that is unsubstituted or substituted with at least one R_10a, a C₂-C₆₀heteroaryl alkyl group that is unsubstituted or substituted with at least one R_10a, —C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

a1 to a5, c1, and n1 may each independently be an integer from 0 to 20,

two or more R₁(s) in the number of a1 may optionally be bonded to each other to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

two or more R₂(s) in the number of a2 may optionally be bonded to each other to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

two or more R₃(s) in the number of a3 may optionally be bonded to each other to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

two or more R₄(s) in the number of a4 may optionally be bonded to each other to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

two or more R₅(s) in the number of a5 may optionally be bonded to each other to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

two or more of R₁to R₈may optionally be bonded to each other to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

* and *′ each indicate a binding site to a neighboring atom,

R_10amay be:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, or a C₁-C₆₀alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀arylalkyl group, a C₂-C₆₀heteroarylalkyl group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), or any combination thereof;

a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀aryl alkyl group, or a C₂-C₆₀heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀aryl alkyl group, a C₂-C₆₀heteroaryl alkyl group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or any combination thereof; or

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂), and

Q₁to Q₃, Q₁₁to Q₁₃, Q₂₁to Q₂₃, and Q₃₁to Q₃₃may each independently be: hydrogen; deuterium; —F; —C₁; —Br; —I; a hydroxyl group; a cyano group; a nitro group; or a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₆₀carbocyclic group, or a C₁-C₆₀heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

In an embodiment, the light-emitting device may further include a second compound comprising at least one π electron-deficient nitrogen-containing C₁-C₆₀cyclic group, a third compound comprising a group represented by Formula 3, a fourth compound that may be a delayed fluorescence compound, or any combination thereof, wherein the organometallic compound, the second compound, the third compound, and the fourth compound are different from each other, and Formula 3 is explained below.

In an embodiment, the second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.

In an embodiment, the fourth compound may be a compound comprising at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.

In an embodiment, the emission layer may include: a first compound which may be the organometallic compound represented by Formula 1; and the second compound, the third compound, the fourth compound, or any combination thereof, wherein the emission layer may emit blue light, and a maximum emission wavelength of the blue light may be in a range of about 430 nm to about 500 nm.

According to embodiments, provided is an electronic apparatus which may include the light-emitting device.

In an embodiment, the electronic apparatus may further include a thin-film transistor, wherein the thin-film transistor may include a source electrode and a drain electrode, and the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode.

In an embodiment, the electronic apparatus may further include a color filter, a quantum dot color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.

According to embodiments, provided is a consumer product which may include the light-emitting device.

In an embodiment, the consumer product may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality or augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater or stadium screen, a phototherapy device, or a signboard.

According to embodiments, provided is the organometallic compound which may be represented by Formula 1.

In an embodiment, ring CY₁may be: an X₁-containing 5-membered ring; an X₁-containing 5-membered ring condensed with at least one 6-membered ring; or an X₁-containing 6-membered ring, wherein the X₁-containing 5-membered ring may be a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole group, a thiazole group, an isothiazole group, an oxadiazole group, or a thiadiazole group, and the X₁-containing 6-membered ring and the 6-membered ring which is optionally condensed to the X₁-containing 5-membered ring may each independently be a benzene group, a pyridine group, or a pyrimidine group.

In an embodiment, rings CY₂, CY₃, and CY₄may each independently be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a benzofluorene group, a naphthobenzosilole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzocarbazole group, a dibenzofluorene group, a dinaphthosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadibenzocarbazole group, an azadibenzofluorene group, or an azadinaphthosilole group.

In an embodiment, ring CY₅may be an X₅-containing 5-membered ring, and the X₅-containing 5-membered ring may be a pyrrole group, a furan group, or a thiophene group.

In an embodiment, X₅₁may be ′*—N—*′ or *—C′R₆)—*′.

In an embodiment, R₁to R₈and T₁may each independently be: hydrogen, deuterium, —F, or a cyano group; a C₁-C₂₀alkyl group or a C₃-C₁₀cycloalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof; or a phenyl group, a naphthyl group, a dibenzofuranyl group, or a dibenzothiophenyl 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 phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C₁-C₂₀alkyl) phenyl group, or any combination thereof.

In an embodiment, in Formula 1, a group represented by *-(L₁)_b1-(T₁)_c1may be a group represented by Formula CY1A, which is explained below.

In an embodiment, the organometallic compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2, which are explained below.

In an embodiment, the organometallic compound may have a maximum emission wavelength less than or equal to about 500 nm.

In an embodiment, the organometallic compound may have an energy level of a triplet metal-centered (³MC) state greater than or equal to about 0.5 kcal/mol.

It is to be understood that the embodiments above are described in a generic and explanatory sense only and not for the purpose of limitation, and the disclosure is not limited to the embodiments described above.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other aspects and features of the disclosure will be more apparent by describing in detail embodiments thereof with reference to the accompanying drawings, in which:

FIG. 1 is a schematic cross-sectional view of a structure of a light-emitting device according to an embodiment; and

FIG. 2 is a schematic cross-sectional view of an electronic apparatus according to an embodiment; and

FIG. 3 is a schematic cross-sectional view of an electronic apparatus according to another embodiment.

DETAILED DESCRIPTION OF THE EMBODIMENTS

The disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. This disclosure may, however, be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the disclosure to those skilled in the art.

In the drawings, the sizes, thicknesses, ratios, and dimensions of the elements may be exaggerated for ease of description and for clarity. Like numbers refer to like elements throughout.

In the description, it will be understood that when an element (or region, layer, part, etc.) is referred to as being “on”, “connected to”, or “coupled to” another element, it can be directly on, connected to, or coupled to the other element, or one or more intervening elements may be present therebetween. In a similar sense, when an element (or region, layer, part, etc.) is described as “covering” another element, it can directly cover the other element, or one or more intervening elements may be present therebetween.

In the description, when an element is “directly on,” “directly connected to,” or “directly coupled to” another element, there are no intervening elements present. For example, “directly on” may mean that two layers or two elements are disposed without an additional element such as an adhesion element therebetween.

As used herein, the expressions used in the singular such as “a,” “an,” and “the,” are intended to include the plural forms as well, unless the context clearly indicates otherwise.

As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. For example, “A and/or B” may be understood to mean “A, B, or A and B.” The terms “and” and “or” may be used in the conjunctive or disjunctive sense and may be understood to be equivalent to “and/or”.

In the specification and the claims, the term “at least one of” is intended to include the meaning of “at least one selected from the group of” for the purpose of its meaning and interpretation. For example, “at least one of A and B” may be understood to mean “A, B, or A and B.” When preceding a list of elements, the term, “at least one of,” modifies the entire list of elements and does not modify the individual elements of the list.

It will be understood that, although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Thus, a first element could be termed a second element without departing from the teachings of the disclosure. Similarly, a second element could be termed a first element, without departing from the scope of the disclosure.

The spatially relative terms “below”, “beneath”, “lower”, “above”, “upper”, or the like, may be used herein for ease of description to describe the relations between one element or component and another element or component as illustrated in the drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation, in addition to the orientation depicted in the drawings. For example, in the case where a device illustrated in the drawing is turned over, the device positioned “below” or “beneath” another device may be placed “above” another device. Accordingly, the illustrative term “below” may include both the lower and upper positions. The device may also be oriented in other directions and thus the spatially relative terms may be interpreted differently depending on the orientations.

The terms “about” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the recited value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the recited quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the stated value.

It should be understood that the terms “comprises,” “comprising,” “includes,” “including,” “have,” “having,” “contains,” “containing,” and the like are intended to specify the presence of stated features, integers, steps, operations, elements, components, or combinations thereof in the disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as commonly understood by those skilled in the art to which this disclosure pertains. 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 should not be interpreted in an ideal or excessively formal sense unless clearly defined in the specification.

An organometallic compound according to an embodiment may be represented by Formula 1:

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In Formula 1, M may be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu).

In an embodiment, M may be platinum (Pt).

In Formula 1, X₁may be C, and X₂to X₄may each independently be C or N.

In an embodiment, X₁may be a carbon of a carbene moiety.

In an embodiment, X₂and X₃may each be C, and X₄may be N.

In Formula 1, a bond between X₁and M may be a coordinate bond; one of a bond between X₂and M, a bond between X₃and M, and a bond between X₄and M may be a coordinate bond; and the remainder of X₂to X₄may each be a covalent bond.

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

In an embodiment, X₄may be N, and a bond between X₄and M may be a coordinate bond.

In Formula 1, rings CY₁, CY₂, CY₃, and CY₄may each independently be a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group.

In an embodiment, for example, ring CY₁may be a C₁-C₆₀nitrogen-containing heterocyclic group.

In an embodiment, ring CY₁may be an X₁-containing 5-membered ring; an X₁-containing 5-membered ring condensed with at least one 6-membered ring; or an X₁-containing 6-membered ring.

For example, ring CY₁may include a 5-membered ring bonded to M in Formula 1 via X₁. In an embodiment, the X₁-containing 5-membered ring may be a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole group, a thiazole group, an isothiazole group, an oxadiazole group, or a thiadiazole group; and the X₁-containing 6-membered ring and the 6-membered ring which may be optionally condensed to the X₁-containing 5-membered ring may each independently be a benzene group, a pyridine group, or a pyrimidine group.

In an embodiment, ring CY₁may be an X₁-containing 5-membered ring, and the X₁-containing 5-membered ring may be an imidazole group or a triazole group.

In an embodiment, ring CY₁may be an X₁-containing 5-membered ring condensed with at least one 6-membered ring, and the X₁-containing 5-membered ring condensed with the at least one 6-membered ring may be a benzimidazole group or an imidazopyridine group.

In an embodiment, ring CY₁may be a benzimidazole group.

In an embodiment, ring CY₂to ring CY₄may each independently be a benzene group, a pyridine group, or a pyrimidine group.

In an embodiment, ring CY₂may be a benzene group.

In an embodiment, ring CY₃may be a benzene group.

In an embodiment, ring CY₄may be a pyridine group.

In Formula 1, X₅may be C.

In Formula 1, ring CY₅may be: an X₅-containing 5-membered ring; or an X₅-containing 5-membered ring condensed with at least one 6-membered ring.

For example, ring CY₅may include a 5-membered ring bonded to X₅₁in Formula 1 via X₅. In an embodiment, the X₅-containing 5-membered ring may be a pyrrole group, a furan group, a thiophene group, a pyrazole group, an imidazole group, an oxazole group, an iso-oxazole group, a thiazole group, or an isothiazole group; and a 6-membered ring which may optionally be condensed to the X₅-containing 5-membered ring may be a benzene group, a pyridine group, or a pyrimidine group.

In an embodiment, ring CY₅may be an X₅-containing 5-membered ring; and the X₅-containing 5-membered ring may be a pyrrole group, a furan group, or a thiophene group.

In an embodiment, ring CY₅may be a furan group or a thiophene group.

In Formula 1, X₅₁may be *—N—*′, *—B—*′, *—P—*′, *—C(R₆)—*′, *—Si(R₆)—*′, or *—Ge(R₆)—*′. In an embodiment, when X₅₁is *—C(R₆)—*′, *—Si(R₆)—*′, or *—Ge(R₆)—*′, R₆may be: hydrogen or deuterium; or a C₁-C₁₀alkyl group that is unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof, but is not limited thereto.

In an embodiment, X₅₁may be *—N—*′, *—B—*′, *—P—*′, *—C(R₆)—*′, or *—Si(R₆)—*′.

In an embodiment, X₅₁may be *—N—*′ or *—C(R₆)—*′.

In Formula 1, X₅₂may be a single bond, *—N(R₇)—*′, *—B(R₇)—*′, *—P(R₇)—*′, *—C(R₇)(R₈)—*′, *—Si(R₇)(R₈)—*′, *—Ge(R₇)(R₈)—*′ *—S—*′ *—Se—*′ *—O—*′ *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*′ *—C(R₇)═*′, *═C(R₇)—*′, *—C(R₇)═C(R⁸)—*′, *—C(═S)—*′, or *—C≡C—*′.

In an embodiment, X₅₂may be a single bond, *—N(R₇)—*′, *—B(R₇)—*′, *—P(R₇)—*′, *—C(R₇)(R₈)—*′, *—Si(R₇)(R₈)—*′, *—Ge(R₇)(R₈)—*′, *—S—*′ *—Se—*′, or *—O—*′.

In an embodiment, X₅₂may be a single bond, *—N(R₇)—*′, *—B(R₇)—*′, or *—P(R₇)—*′.

In an embodiment, in Formula 1,

X₅₂may be a single bond, and a group represented by

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in Formula 1 may be a group represented by Formula CY3A or CY3B, or

X₅₂may not be a single bond, and a group represented by

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in Formula 1 may be a group represented by Formula CY3C, or

X₅₂may be *—N(R₇)—*′, and R₇and R₃may be bonded together to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a:

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In Formulae CY3A to CY3C,

X₃and X₃₁to X₃₃may each independently be C or N,

rings CY₃₁, CY₃₂, and CY₃₃may each independently be the same as described in connection with ring CY₃,

a bond between X₃₁and X₃, a bond between X₃and X₃₂, and a bond between X₃₂and X₃₃may each be a chemical bond,

*″ indicates a binding site to X₅₁,

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

*′ indicates a binding site to X₅₂.

In an embodiment, X₃₁, X₃, and X₃₂in Formulae CY3A and CY3B may each be C, and X₃₃may be N.

In an embodiment, X₃₁, X₃, and X₃₂in Formula CY3C may each be C.

In Formula 1, L₁may be a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a.

In an embodiment, L₁may be a benzene group, a naphthalene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one R_10a.

In Formula 1, b1 indicates the number of L₁(s), and may be an integer from 1 to 5. When b1 is 2 or more, two or more L₁(s) may be identical to or different from each other. In an embodiment, b1 may be 1 or 2.

In Formula 1, R₁to R₈and T₁may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group that is unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group that is unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group that is unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group that is unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryloxy group that is unsubstituted or substituted with at least one R_10a, a C₆-C₆₀arylthio group that is unsubstituted or substituted with at least one R_10a, a C₇-C₆₀aryl alkyl group that is unsubstituted or substituted with at least one R_10a, a C₂-C₆₀heteroaryl alkyl group that is unsubstituted or substituted with at least one R_10a, —C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂).

In an embodiment, R₁to R₈and T₁may each independently be:

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

a C₁-C₂₀alkyl group or a C₃-C₁₀cycloalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof; or

a phenyl group, a naphthyl group, a dibenzofuranyl group, or a dibenzothiophenyl 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 phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C₁-C₂₀alkyl) phenyl group, or any combination thereof.

In an embodiment, in Formula 1, T₁may be: a C₁-C₂₀alkyl group or a C₃-C₁₀cycloalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof; or

In Formula 1, a1, a2, a3, a4, a5, c1, and n1 may respectively indicate the numbers of R₁, R₂, R₃, R₄, R₅, T₁, and a group represented by *-(L₁)_b1-(T₁)_c1, and may each independently be an integer from 0 to 20.

In an embodiment, a1, a2, a3, a4, and a5 may each independently be 0, 1, 2, 3, 4, or 5.

In an embodiment, c1 may be 1 or 2.

In an embodiment, n1 may be 0 or 1.

In an embodiment, c1 may be 2, and n1 may be 1.

In Formula 1, two or more R₁(s) in the number of a1 may be optionally bonded to each other to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a.

In Formula 1, two or more R₂(s) in the number of a2 may be optionally bonded to each other to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a.

In Formula 1, two or more R₃(s) in the number of a3 may be optionally bonded to each other to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a.

In Formula 1, two or more R₄(s) in the number of a4 may be optionally bonded to each other to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a.

In Formula 1, two or more R₅(s) in the number of a5 may be optionally bonded to each other to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a.

In Formula 1, two or more of R₁to R₈may be optionally bonded to each other to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a.

In Formula 1, * and *′ each indicate a binding site to a neighboring atom.

In Formula 1, R_10amay be the same as described herein.

In an embodiment, the organometallic compound may be represented by Formula 1-1 or Formula 1-2.

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In Formulae 1-1 and 1-2,

M, X₁to X₄, X₅₁, L₁, b1, T₁, and c1 may each independently be the same as described herein,

E₁may be O or S,

W₁is the same as described in connection with R₅,

d3 may be an integer from 0 to 3,

two or more W₁(s) in the number of d3 may optionally be bonded to each other to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

X₁₁may be C(R₁₁) or N, X₁₂may be C(R₁₂) or N, X₁₃may be C(R₁₃) or N, and X₁₄may be C(R₁₄) or N,

R₁₁to R₁₄may each independently be the same as described in connection with R₁, and two or more of R₁₁to R₁₄may optionally be bonded together to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

X₂₁may be C(R₂₁) or N, X₂₂may be C(R₂₂) or N, and X₂₃may be C(R₂₃) or N,

R₂₁to R₂₃may each independently be the same as described in connection with R₂, and two or more of R₂₁to R₂₃may optionally be bonded together to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

X₃₁may be C(R₃₁) or N, X₃₂may be C(R₃₂) or N, X₃₃may be C(R₃₃) or N, X₃₄may be C(R₃₄) or N, X₃₅may be C(R₃₅) or N, and X₃₆may be C(R₃₆) or N,

R₃₁to R₃₆may each independently be the same as described in connection with R₃, and two or more of R₃₁to R₃₆may optionally be bonded together to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

R₄₁to R₄₄may each independently be the same as described in connection with R₄, and two or more of R₄₁to R₄₄may optionally be bonded together to form a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a.

In an embodiment, in Formulae 1-1 and 1-2, R₄₂may neither be hydrogen nor deuterium.

In an embodiment, in Formulae 1-1 and 1-2, R₄₂may be a C₁-C₂₀alkyl group or a C₃-C₁₀cycloalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof.

In an embodiment, in Formulae 1-1 and 1-2, R₄₃may be: hydrogen, deuterium, —F, or a cyano group;

a C₁-C₂₀alkyl group or a C₃-C₁₀cycloalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof; or

In an embodiment, in Formulae 1-1 and 1-2, R₄₃may be: hydrogen, deuterium, —F, or a cyano group; or a phenyl group that is 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 deuterated phenyl group, a fluorinated phenyl group, a (C₁-C₂₀alkyl)phenyl group, or any combination thereof.

In an embodiment, in Formulae 1-1 and 1-2, R₄₁and R₄₄may each independently be hydrogen or deuterium.

In an embodiment, in Formula 1, a group represented by

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may be a group represented by one of Formulae CY1-1 to CY1-8:

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In Formulae CY1-1 to CY1-8,

X₁may be C,

Y₁may include O, S, N, C, or Si,

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

*′ indicates a binding site to a neighboring atom in Formula 1.

In an embodiment, in Formula 1, a group represented by

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may be a group represented by one of Formulae CY1(1) to CY1(8):

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In Formulae CY1(1) to CY1(8),

X₁may be C,

L₁, T₁, and c1 may each independently be the same as described herein,

R₁₁to R₁₄may each independently be the same as described in connection with R₁,

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

*′ indicates a binding site to ring CY₂in Formula 1.

In an embodiment, in Formula 1, a group represented by *-(L₁)_b1-(T₁)_c1may be a group represented by Formula CY1A:

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In Formula CY1A,

Z₂₀to Z₂₂may each independently be hydrogen, or may each independently be the same as described in connection with R_10a,

T₁₁and T₁₂may each independently be the same as described in connection with T₁, and

* indicates a binding site to ring CY₁.

In an embodiment, in Formula CY1A, T₁₁and T₁₂may each independently be: hydrogen;

a C₁-C₂₀alkyl group or a C₃-C₁₀cycloalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof; or

In an embodiment, in Formula 1, a group represented by *-(L₁)_b1-(T₁)_c1may be a group represented by Formula CY1(A) or Formula CY1(A2):

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In Formulae CY1(A) and CY1(A2),

Z₁₀to Z₂₂may each independently be hydrogen, or may each independently be the same as described in connection with R_10a, and

* indicates a binding site to ring CY₁.

In an embodiment, in Formulae CY1(A) and CY1(A2), Z₁₀to Z₂₂may each independently be hydrogen, deuterium, —F, a cyano group, a C₁-C₂₀alkyl group, a deuterated C₁-C₂₀alkyl group, a fluorinated C₁-C₂₀alkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, or a (C₁-C₂₀alkyl)phenyl group.

In an embodiment, in Formula 1, a group represented by

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may be a group represented by one of Formulae CY2-1 to CY2-11:

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In Formulae CY2-1 to CY2-11,

X₂is the same as described herein,

Y₂may include O, S, N, C, or Si,

* indicates a binding site to M in Formula 1,

*′ indicates a binding site to ring CY₁in Formula 1, and

*″ indicates a binding site to X₅₁in Formula 1.

In an embodiment, a group represented by

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in Formula 1 and a group represented by

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in Formulae 1-1 and 1-2 may each independently be a group represented by one of Formulae CY2(1) to CY2(26):

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In Formulae CY2(1) to CY2(26),

X₂is the same as described herein,

X₂₁may be O, S, N(R₂₀), C(R_20a)(R_20b), or Si(R_20a)(R_20b),

R₂₀, R_20a, R_20b, and R₂₁to R₂₃may each independently be the same as described in connection with R₂, and R₂₁to R₂₃may each not be hydrogen,

* indicates a binding site to M in Formula 1,

*′ indicates a binding site to ring CY₁in Formula 1, and

*″ indicates a binding site to X₅₁in Formula 1.

In an embodiment, in Formula 1, a group represented by

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may be a group represented by one of Formulae CY3(1) to CY3(20), and in Formulae 1-1 and 1-2 a group represented by

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may be a group represented by one of Formulae CY3(1) to CY3(12):

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In Formulae CY3(1) to CY3(20),

X₃is the same as described herein,

R₃₁to R₃₆may each independently be the same as described in connection with R₃, wherein R₃₁to R₃₆may each not be hydrogen,

* indicates a binding site to M in Formula 1,

*′ indicates a binding site to X₅₂in Formula 1, and

*″ indicates a binding site to X₅₁in Formula 1.

In an embodiment, a group represented by

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in Formula 1 and a group represented by

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in Formulae 1-1 and 1-2 may each independently be one of groups represented by Formulae CY5-1 to CY5-16:

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In Formulae CY5-1 to CY5-16,

E₁may be O or S,

W₁₁to W₁₄may each independently be the same as described in connection with R₅, wherein W₁₁to W₁₄may each not be hydrogen, and

* indicates a binding site to X₅₁in Formula 1.

In an embodiment, in Formulae CY5-1 to CY5-16, W₁₁to W₁₄may each independently be: deuterium, —F, or a cyano group;

a C₁-C₂₀alkyl group or a C₃-C₁₀cycloalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof; or

In an embodiment, in Formulae CY5-1 to CY5-16, W₁₁to W₁₄may each independently be: a C₁-C₂₀alkyl group or a C₃-C₁₀cycloalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof; or

In an embodiment, a group represented by

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in Formula 1 and a group represented by

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in Formulae 1-1 and 1-2 may each independently be one of groups represented by Formulae CY5-1 to CY5-8.

In an embodiment, the organometallic compound represented by Formula 1 may have a maximum emission wavelength (nm) less than or equal to about 500 nm.

In an embodiment, the organometallic compound represented by Formula 1 may have a maximum emission wavelength in a range of about 390 nm to about 500 nm. For example, the organometallic compound represented by Formula 1 may have a maximum emission wavelength in a range of about 410 nm to about 490 nm. For example, the organometallic compound represented by Formula 1 may have a maximum emission wavelength in a range of about 430 nm to about 480 nm. For example, the organometallic compound represented by Formula 1 may have a maximum emission wavelength in a range of about 440 nm to about 475 nm. For example, the organometallic compound represented by Formula 1 may have a maximum emission wavelength in a range of about 455 nm to about 470 nm.

A maximum emission wavelength of the organometallic compound represented by Formula 1 may indicate an actual maximum emission wavelength (λ_max^exp) evaluated by utilizing a density functional theory (DFT) method. The evaluation method may refer to the method described in Evaluation Example 1 herein.

In an embodiment, the organometallic compound represented by Formula 1 may have an energy level of a triplet metal-centered (³MC) state (hereinafter, also referred to as an energy level of a ³MC state) greater than or equal to about 0.5 kcal/mol.

In an embodiment, the organometallic compound represented by Formula 1 may have an energy level of a ³MC state less than or equal to about 1.2 kcal/mol.

In an embodiment, the organometallic compound represented by Formula 1 may have an energy level of a ³MC state in a range of about 0.5 kcal/mol to about 1.2 kcal/mol. For example, the organometallic compound represented by Formula 1 may have an energy level of a ³MC state in a range of about 0.6 kcal/mol to about 1.1 kcal/mol. For example, the organometallic compound represented by Formula 1 may have an energy level of a ³MC state in a range of about 0.7 kcal/mol to about 1.0 kcal/mol. For example, the organometallic compound represented by Formula 1 may have an energy level of a ³MC state in a range of about 0.75 kcal/mol to about 0.95 kcal/mol.

The energy level of the ³MC state of the organometallic compound may be evaluated by utilizing a DFT method. The evaluation method may refer to the method described in Evaluation Example 1 herein.

In an embodiment, the organometallic compound represented by Formula 1 may have a ratio of presence of a triplet metal-to-ligand charge transfer (³MLCT) state (hereinafter, also referred to as a ratio of presence of ³MLCT) of about 10% or more. In an embodiment, a ratio of presence of ³MLCT may be in a range of about 10% to about 20%. For example, a ratio of presence of ³MLCT may be in a range of about 11% to about 19%. For example, a ratio of presence of ³MLCT may be in a range of about 11% to about 17%. For example, a ratio of presence of ³MLCT may be in a range of about 11% to about 15%.

A ratio of presence of ³MLCT of the organometallic compound may be evaluated by utilizing a DFT method. The evaluation method may refer to the method described in Evaluation Example 1 herein.

In an embodiment, the organometallic compound represented by Formula 1 may be one of Compounds 1 to 120, but is not limited thereto:

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The organometallic compound represented by Formula 1 has, as a linker that links rings CY₂and CY₃together, a moiety that includes ring CY₅(including an X₅-containing 5-membered ring) linked to X₅₁via X₅, wherein the X₅-containing 5-membered ring of CY₅is a heterocyclic group (for example, a furan group, a thiophene group, etc.), and X₅that is bonded to X₅₁is carbon. Accordingly, the organometallic compound represented by Formula 1 may exhibit relatively excellent ³MLCT, ³MC, and triplet ligand-centered (³LC) state characteristics. The occurrence of a second peak outside a maximum peak wavelength range on an emission spectrum is suppressed, and thus, blue light with improved color purity may be emitted.

Accordingly, due to the use of the organometallic compound, an electronic device (for example, an organic light-emitting device) having low driving voltage and high luminescence efficiency may be implemented.

Methods of synthesizing the organometallic compound represented by Formula 1 may be readily understood to those of ordinary skill in the art by referring to Synthesis Examples and/or Examples described herein.

A light-emitting device according to an embodiment may include a first electrode, a second electrode facing the first electrode, an interlayer between the first electrode and the second electrode and including an emission layer, an organometallic compound represented by Formula 1, as described herein.

In an embodiment, the first electrode of the light-emitting device may be an anode; the second electrode of the light-emitting device may be a cathode; the interlayer 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 layer; the hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof; and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

In an embodiment, the interlayer of the light-emitting device may include the organometallic compound represented by Formula 1.

In an embodiment, the emission layer of the light-emitting device may include the organometallic compound represented by Formula 1.

In an embodiment, the emission layer may emit blue light. In an embodiment, the emission layer may emit blue light having a maximum emission wavelength in a range of about 410 nm to about 500 nm. For example, the emission layer may emit blue light having a maximum emission wavelength in a range of about 420 nm to about 490 nm. For example, the emission layer may emit blue light having a maximum emission wavelength in a range of about 430 nm to about 480 nm. For example, the emission layer may emit blue light having a maximum emission wavelength in a range of about 430 nm to about 470 nm.

In an embodiment, the emission layer in the light-emitting device may include a dopant and a host, and the dopant may include the organometallic compound represented by Formula 1. For example, the organometallic compound may serve as a dopant. The emission layer may emit, for example, blue light. The blue light may have a maximum emission wavelength, for example, in a range of about 430 nm to about 500 nm. For example, the blue light may have a maximum emission wavelength in a range of about 430 nm to about 470 nm.

In an embodiment, the electron transport region of the light-emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. In an embodiment, the hole blocking layer may directly contact the emission layer.

In an embodiment, the light-emitting device may further include at least one of a first capping layer arranged outside the first electrode and a second capping layer arranged outside the second electrode, and the at least one of the first capping layer and the second capping layer may include the organometallic compound represented by Formula 1. Further details on the first capping layer and/or second capping layer are as described in the specification.

In an embodiment, the light-emitting device may include a first capping layer arranged outside the first electrode and including the organometallic compound represented by Formula 1; a second capping layer arranged outside the second electrode and including the organometallic compound represented by Formula 1; or the first capping layer and the second capping layer.

The wording “(interlayer and/or capping layer) includes an organometallic compound” as used herein may be understood as “(interlayer and/or capping layer) may include one kind of organometallic compound represented by Formula 1 or two different kinds of organometallic compounds, each represented by Formula 1”.

In an embodiment, the interlayer and/or capping layer may include Compound 1 only as the organometallic compound. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In an embodiment, the interlayer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be present in a same layer (for example, all of Compound 1 and Compound 2 may be present in the emission layer), or may be present in different layers (for example, Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).

The term “interlayer” as used herein refers to a single layer and/or multiple layers located between the first electrode and the second electrode of the light-emitting device.

In an embodiment, the light-emitting device may include:

a first compound which is the organometallic compound represented by Formula 1; and

a second compound including at least one π electron-deficient nitrogen-containing C₁-C₆₀cyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence (for example, the fourth compound may be a delayed fluorescence compound), or any combination thereof,

wherein the first compound, the second compound, the third compound, and the fourth compound may be different from each other:

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In Formula 3, ring CY₇₁and ring CY₇₂may each independently be a π electron-rich C₃-C₆₀cyclic group or a pyridine group.

In Formula 3, X₇₁may be: a single bond; or a linking group including O, S, N, B, C, Si, or any combination thereof.

In Formula 3, * indicates a binding site to a neighboring atom in the third compound.

CBP and mCBP may be excluded from the third compound:

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In an embodiment, in the light-emitting device,

the emission layer may include: the first compound; and the second compound, the third compound, the fourth compound, or any combination thereof, and

the emission layer may emit phosphorescence or fluorescence emitted from the first compound. In an embodiment, blue light may be emitted from the first compound, and the blue light may have a maximum emission wavelength, for example, in a range of about 430 nm to about 500 nm. For example, the blue light may have a maximum emission wavelength in a range of about 430 nm to about 470 nm.

[Descriptions of Second Compound, Third Compound, and Fourth Compound]

In an embodiment, the second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.

In an embodiment, the light-emitting device may further include at least one of the second compound and the third compound, in addition to the first compound.

In an embodiment, the light-emitting device may further include the fourth compound, in addition to the first compound.

In an embodiment, the light-emitting device may include the first compound, the second compound, the third compound, and the fourth compound.

In an embodiment, the interlayer may include the second compound. The interlayer may further include, in addition to the first compound and the second compound, the third compound, the fourth compound, or any combination thereof.

In an embodiment, a difference between a triplet energy level (eV) of the fourth compound and a singlet energy level (eV) of the fourth compound may be in a range of about 0 eV to about 0.5 eV. For example, a difference between a triplet energy level (eV) of the fourth compound and a singlet energy level (eV) of the fourth compound may be in a range of about 0 eV or higher and about 0.3 eV or lower.

In an embodiment, the fourth compound may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.

In an embodiment, the fourth compound may be a C₈-C₆₀polycyclic group-containing compound including at least two condensed cyclic groups that share boron (B).

In an embodiment, the fourth compound may include a condensed ring in which at least one third ring may be condensed with at least one fourth ring,

wherein the third ring may be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norbornane 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 pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and

wherein the fourth ring may be a 1,2-azaborinine group, a 1,3-azaborinine group, a 1,4-azaborinine group, a 1,2-dihydro-1,2-azaborinine group, a 1,4-oxaborinine group, a 1,4-thiaborinine group, or a 1,4-dihydroborinine group.

In an embodiment, the interlayer may include the fourth compound. The interlayer may include, in addition to the first compound and the fourth compound, the second compound, the third compound, or any combination thereof.

In an embodiment, the interlayer may include the third compound. In an embodiment, the third compound may not include CBP as described herein nor mCBP as described herein.

The emission layer in the interlayer may include: the first compound; and the second compound, the third compound, the fourth compound, or any combination thereof.

The emission layer may emit phosphorescence or fluorescence emitted from the first compound. In an embodiment, phosphorescence or fluorescence emitted from the first compound may be blue light.

In an embodiment, the emission layer in the light-emitting device may include the first compound and the second compound, and the first compound and the second compound may form an exciplex.

In an embodiment, the emission layer in the light-emitting device may include the first compound, the second compound, and the third compound, and the first compound and the second compound may form an exciplex.

In an embodiment, the emission layer in the light-emitting device may include the first compound and the fourth compound, and the fourth compound may serve to improve color purity, luminescence efficiency, and lifespan characteristics of the light-emitting device.

In an embodiment, the second compound may include a compound represented by Formula 2:

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In Formula 2,

L₆₁to L₆₃may each independently be a single bond, a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, or a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

b61 to b63 may each independently be an integer from 1 to 5,

X₆₄may be N or C(R₆₄), X₆₅may be N or C(R₆₅), X₆₆may be N or C(R₆₆), and at least one of X₆₄to X₆₆may be N,

R₆₁to R₆₆may each be the same as described herein, and

R_10amay be the same as described herein.

In an embodiment, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:

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In Formulae 3-1 to 3-5,

ring CY₇₁to ring CY₇₄may each independently be a π electron-rich C₃-C₆₀cyclic group or a pyridine group,

X₈₂may be a single bond, O, S, N—[(L₈₂)_b82-R₈₂], C(R_82a)(R_82b), or Si(R_82a)(R_82b),

X₈₃may be a single bond, O, S, N—[(L₈₃)_b83-R₈₃], C(R_83a)(R_83b), or Si(R_83a)(R_83b),

X₈₄may be O, S, N—[(L₈₄)_b84-R₈₄], C(R_84a)(R_84b), or Si(R_84a)(R_84b),

X₈₅may be C or Si,

L₈₁to L₈₅may each independently be a single bond, *—C(Q₄)(Q₅)-*′, *—Si(Q₄)(Q₅)-*′, a π electron-rich C₃-C₆₀cyclic group that is unsubstituted or substituted with at least one R_10a, or a pyridine group that is unsubstituted or substituted with at least one R_10a, wherein Q₄and Q₅may each independently be the same as described in connection with Q₁as provided herein,

b81 to b85 may each independently be an integer from 1 to 5,

R₇₁to R₇₄, R₈₁to R₈₅, R_82a, R_82b, R_83a, R_83b, R_84a, and R_84bmay each be the same as described herein,

a71 to a74 may each independently be an integer from 0 to 20, and

R_10amay be the same as described herein.

In an embodiment, the fourth compound may be a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:

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In Formulae 502 and 503,

ring A501 to ring A504 may each independently be a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group,

Y₅₀₅may be O, S, N(R₅₀₅), B(R₅₀₅), C(R_505a)(R_505b), or Si(R_505a)(R_505b),

Y₅₀₆may be O, S, N(R₅₀₆), B(R₅₀₆), C(R_506a)(R_506b), or Si(R_506a)(R_506b),

Y₅₀₇may be O, S, N(R₅₀₇), B(R₅₀₇), C(R_507a)(R_507b), or Si(R_507a)(R_507b),

Y₅₀₈may be O, S, N(R₅₀₈), B(R₅₀₈), C(R_508a)(R_508b), or Si(R_508a)(R_508b),

Y₅₁and Y₅₂may each independently be B, P(═O), or S(═O),

R_500a, R_500b, R₅₀₁to R₅₀₈, R_505a, R_505b, R_506a, R_506b, R_507a, R_507b, R_508a, and R_508bmay each be the same as described herein,

a501 to a504 may each independently be an integer from 0 to 20, and

R_10amay be the same as described herein.

[Description of Formulae 2, 3, 3-1 to 3-5, 502, and 503]

In Formula 2, b61 to b63 may respectively indicate the numbers of L₆₁(s) to L₆₃(s), and b61 to b63 may each independently be an integer from 1 to 5. When b61 is 2 or greater, at least two L₆₁(s) may be identical to or different from each other, when b62 is 2 or greater, at least two L₆₂(s) may be identical to or different from each other, and when b63 is 2 or greater, at least two L₆₃(s) may be identical to or different from each other. In an embodiment, b61 to b63 may each independently be 1 or 2.

In embodiments, in Formula 2, L₆₁to L₆₃may each independently be:

a single bond; or

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, a benzothiadiazole group, a dibenzooxacilline group, a dibenzothiacilline group, a dibenzodihydroazacilline group, a dibenzodihydrodicilline group, a dibenzodihydrocilline group, a dibenzodioxane group, a dibenzooxathiene group, a dibenzooxazine group, a dibenzopyran group, a dibenzodithiine group, a dibenzothiazine group, a dibenzothiopyran group, a dibenzocyclohexadiene group, a dibenzodihydropyridine group, or a dibenzodihydropyrazine group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a dimethyldibenzosilolyl group, a diphenyldibenzosilolyl group, —O(Q₃₁), —S(Q₃₁), —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —P(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof,

wherein Q₃₁to Q₃₃may each independently be hydrogen, deuterium, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group.

In an embodiment, in Formula 2, a bond between L₆₁and R₆₁, a bond between L₆₂and R₆₂, a bond between L₆₃and R₆₃, a bond between at least two L₆₁(s), a bond between at least two L₆₂(s), a bond between at least two L₆₃(s), a bond between L₆₁and a carbon atom between X₆₄and X₆₅in Formula 2, a bond between L₆₂and a carbon atom between X₆₄and X₆₆in Formula 2, and a bond between L₆₃and a carbon atom between X₆₅and X₆₆in Formula 2 may each be a carbon-carbon single bond.

In Formula 2, X₆₄may be N or C(R₆₄), X₆₅may be N or C(R₆₅), X₆₆may be N or C(R₆₆), and at least one of X₆₄to X₆₆may be N. R₆₄to R₆₆may each be the same as described herein. In an embodiment, two or three of X₆₄to X₆₆may each be N.

R₆₁to R₆₆, R₇₁to R₇₄, R₈₁to R₈₅, R_82a, R_82b, R_83a, R_83b, R_84aand R_84b, R_500a, R_500b, R₅₀₁to R₅₀₈, R_505a, R_505b, R_506a, R_506b, R_507a, R_507b, R_508a, and R_508bmay each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group that is unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group that is unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group that is unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group that is unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryloxy group that is unsubstituted or substituted with at least one R_10a, a C₆-C₆₀arylthio group that is unsubstituted or substituted with at least one R_10a, —C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂).

Q₁to Q₃may each be the same as described herein.

In an embodiment, R₆₁to R₆₆, R₇₁to R₇₄, R₈₁to R₈₅, R_82a, R_82b, R_83a, R_83b, R_84a, R_84b, R_500a, R_500b, R₅₀₁to R₅₀₈, R_505a, R_505b, R_506a, R_506b, R_507a, R_507b, R_508a, and R_508bin Formulae 2, 3-1 to 3-5, 502, and 503; and R_10amay each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, or a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group or a C₁-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, 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 biphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;

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 biphenyl group, a C₁-C₁₀alkylphenyl 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 benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilolyl group, or a group represented by Formula 91, 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, 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 biphenyl group, a C₁-C₁₀alkylphenyl 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 benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —O(Q₃₁), —S(Q₃₁), —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —P(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof; or

—C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂), and

Q₁to Q₃and Q₃₁to Q₃₃may each independently be:

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

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each unsubstituted or substituted with deuterium, a C₁-C₁₀alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof:

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wherein in Formula 91,

ring CY₉₁and ring CY₉₂may each independently be a C₅-C₃₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₃₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

X₉₁may be a single bond, O, S, N(R₉₁), B(R₉₁), C(R_91a)(R_11b), or Si(R_91a)(R_11b),

R₉₁, R_91a, and R_91bmay respectively be the same as described in connection with R₈₂, R_82a, and R_82bas provided herein,

R_10amay be the same as described herein, and

* indicates a binding site to a neighboring atom.

In an embodiment, in Formula 91,

ring CY₉₁and ring CY₉₂may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group, each unsubstituted or substituted with at least one R_10a, and

R₁₁, R_11a, and R_91bmay each independently be:

hydrogen or a C₁-C₁₀alkyl group; or

a phenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each unsubstituted or substituted with deuterium, a C₁-C₁₀alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof.

hydrogen, deuterium, —F, a cyano group, a nitro group, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a group represented by one of Formulae 9-1 to 9-19, a group represented by one of Formulae 10-1 to 10-249, —C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), or —P(═O)(Q₁)(Q₂), wherein Q₁to Q₃may each be the same as described herein:

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In Formulae 9-1 to 9-19 and 10-1 to 10-249, * indicates a binding site to a neighboring atom, Ph represents a phenyl group, and TMS represents a trimethylsilyl group.

In Formulae 3-1 to 3-5, 502, and 503, a71 to a74 and a501 to a504 may respectively indicate the number of R₇₁(s) to R₇₄(s) and R₅₀₁(s) to R₅₀₄(s), and a71 to a74 and a501 to a504 may each independently be an integer from 0 to 20. When a71 is 2 or greater, at least two R₇₁(S) may be identical to or different from each other, when a72 is 2 or greater, at least two R₇₂(s) may be identical to or different from each other, when a73 is 2 or greater, at least two R₇₃(s) may be identical to or different from each other, when a74 is 2 or greater, at least two R₇₄(s) may be identical to or different from each other, when a501 is 2 or greater, at least two R₅₀₁(s) may be identical to or different from each other, when a502 is 2 or greater, at least two R₅₀₂(s) may be identical to or different from each other, when a503 is 2 or greater, at least two R₅₀₃(s) may be identical to or different from each other, and when a504 is 2 or greater, at least two R₅₀₄(s) may be identical to or different from each other. In embodiments, a71 to a74 and a501 to a504 may each independently be an integer from 0 to 8.

In an embodiment, in Formula 2, the group represented by *-(L₆₁)_b61-R₆₁and the group represented by *-(L₆₂)_b62-R₆₂may not be a phenyl group.

In an embodiment, in Formula 2, the group represented by *-(L₆₁)_b61-R₆₁may be identical to the group represented by *-(L₆₂)_b62-R₆₂.

In an embodiment, in Formula 2, the group represented by *-(L₆₁)_b61-R₆₁and the group represented by *-(L₆₂)_b62-R₆₂may be different from each other.

In an embodiment, in Formula 2, b61 and b62 may each independently be 1, 2, or 3; and L₆₁and L₆₂may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group that is unsubstituted or substituted with at least one R_10a.

In an embodiment, in Formula 2, R₆₁and R₆₂may each independently be a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryloxy group that is unsubstituted or substituted with at least one R_10a, a C₆-C₆₀arylthio group that is unsubstituted or substituted with at least one R_10a, —C(Q₁)(Q₂)(Q₃), or —Si(Q₁)(Q₂)(Q₃),

wherein Q₁to Q₃may each independently be a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

In an embodiment, in Formula 2,

the group represented by *-(L₆₁)_b61-R₆₁may be a group represented by one of Formulae CY51-1 to CY51-26, and/or

the group represented by *-(L₆₂)_b62-R₆₂may be a group represented by one of Formulae CY52-1 to CY52-26, and/or

the group represented by *-(L₆₃)_b63-R₆₃may be a group represented by one of Formulae CY53-1 to CY53-27, —C(Q₁)(Q₂)(Q₃), or —Si(Q₁)(Q₂)(Q₃):

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In Formulae CY51-1 to CY51-26, CY52-1 to CY52-26, and CY53-1 to CY53-27,

Y₆₃may be a single bond, O, S, N(R₆₃), B(R₆₃), C(R_63a)(R_63b), or Si(R_63a)(R_63b),

Y₆₄may be a single bond, O, S, N(R₆₄), B(R₆₄), C(R_64a)(R_64b), or Si(R_64a)(R_64b),

Y₆₇may be a single bond, O, S, N(R₆₇), B(R₆₇), C(R_67a)(R_67b), or Si(R_67a)(R_67b),

Y₆₈may be a single bond, O, S, N(R₆₈), B(R₆₈), C(R_68a)(R_68b), or Si(R_68a)(R_68b),

Y₆₃and Y₆₄in Formulae CY51-16 and CY51-17 may not each be a single bond at the same time,

Y₆₇and Y₆₈in Formulae CY52-16 and CY52-17 may not each be a single bond at the same time,

R_51ato R_51e, R₆₁to R₆₄, R_63a, R_63b, R_64a, and R_64bmay each independently be the same as described in connection with R₆₁, wherein R_51ato R_51emay not each be hydrogen,

R_52ato R_52e, R₆₅to R₆₈, R_67a, R_67b, R_68a, and R_68bmay each independently be the same as described in connection with R₆₂, wherein R_52ato R_52emay not each be hydrogen,

R_53ato R_53e, R_69a, and R_69bmay each independently be the same as described in connection with R₆₃, wherein R_53ato R_53emay not each be hydrogen, and

* indicates a binding site to a neighboring atom.

In an embodiment,

R_51ato R_51eand R_52ato R_52ein Formulae CY51-1 to CY51-26 and Formulae CY52-1 to 52-26 may each independently be:

—C(Q₁)(Q₂)(Q₃) or —Si(Q₁)(Q₂)(Q₃),

wherein Q₁to Q₃may each independently be a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each unsubstituted or substituted with deuterium, a C₁-C₁₀alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof,

in Formulae CY51-16 and CY51-17, Y₆₃may be O or S and Y₆₄may be Si(R_64a)(R_64b); or Y₆₃may be Si(R_63a)(R_63b) and Y₆₄may be O or S, and

in Formulae CY52-16 and CY52-17, Y₆₇may be O or S and Y₆₈may be Si(R_68a)(R_68b); or Y₆₇may be Si(R_67a)(R_67b) and Y₆₈may be O or S.

In an embodiment, in Formulae 3-1 to 3-5, L₈₁to L₈₅may each independently be:

a single bond; or

*—C(Q₄)(Q₅)-*′ or *—Si(Q₄)(Q₅)-*′; or

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 deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a dimethyldibenzosilolyl group, a diphenyldibenzosilolyl group, —O(Q₃₁), —S(Q₃₁), —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —P(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof,

wherein Q₄, Q₅, and Q₃₁to Q₃₃may each independently be hydrogen, deuterium, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group.

In an embodiment, a group represented by

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in Formulae 3-1 and 3-2 may be a group represented by one of Formulae CY71-1(1) to CY71-1(8), and/or

a group represented by

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in Formulae 3-1 and 3-3 may be a group represented by one of Formulae CY71-2(1) to CY71-2(8), and/or

a group represented by

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in Formulae 3-2 and 3-4 may be a group represented by one of Formulae CY71-3(1) to CY71-3(32), and/or

a group represented by

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in Formulae 3-3 to 3-5 may be a group represented by one of Formulae CY71-4(1) to CY71-4(32), and/or

a group represented by

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in Formula 3-5 may be a group represented by one of Formulae CY71-5(1) to CY71-5(8):

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In Formulae CY71-1(1) to CY71-1(8), CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), CY71-4(1) to CY71-4(32), and CY71-5(1) to CY71-5(8),

X₈₁to X₈₅, L₈₁, b81, R₈₁, and R₈₅may each be the same as described herein,

X₈₆may be a single bond, O, S, N(R₈₆), B(R₈₅), C(R_86a)(R_8b), or Si(R_86a)(R_8b),

X₈₇may be a single bond, O, S, N(R₈₇), B(R₈₇), C(R_8a)(R_87b), or Si(R_87a)(R_87b),

in Formulae CY71-1(1) to CY71-1(8) and CY71-4(1) to CY71-4(32), X₈₆and X₈₇may not each be a single bond at the same time,

X₈₈may be a single bond, O, S, N(R₈₈), B(R₈₈), C(R_88a)(R_88b), or Si(R_88a)(R_88b),

X₈₉may be a single bond, O, S, N(R₈₉), B(R₈₉), C(R_89a)(R_89b), or Si(R_89a)(R_89b),

in Formulae CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), and CY71-5(1) to CY71-5(8), X₈₈and X₈₉may not each be a single bond at the same time, and

R₈₆to R₈₉, R_86a, R_86b, R_87a, R_87b, R_88a, R_88b, R_89a, and R_89bmay each independently be the same as described in connection with R₈₁.

[Examples of Second Compound, Third Compound, and Fourth Compound]

In an embodiment, the second compound may include at least one of Compounds ETH1 to ETH85:

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In an embodiment, the third compound may include at least one of Compounds HTH1 to HTH52:

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In an embodiment, the fourth compound may include at least one of Compounds DFD1 to DFD12:

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In Compounds ETH1 to ETH84, HTH1 to HTH52, and DFD1 to DFD12, “Ph” represents a phenyl group, “D₅” represents substitution with five deuterium atoms, and “D₄” represents substitution with four deuterium atoms. For example, a group represented by

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may be identical to a group represented by

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In an embodiment, the light-emitting device may satisfy at least one of Conditions 1 to 4:

[Condition 1]

LUMO energy level (eV) of the third compound > LUMO energy level (eV) of the first compound;

[Condition 2]

LUMO energy level (eV) of the first compound > LUMO energy level (eV) of the second compound;

[Condition 3]

HOMO energy level (eV) of the first compound > HOMO energy level (eV) of the third compound;

[Condition 4]

HOMO energy level (eV) of the third compound > HOMO energy level (eV) of the second compound.

A highest occupied molecular orbital (HOMO) energy level and a lowest unoccupied molecular orbital (LUMO) energy level of each of the first compound, the second compound, and the third compound may each be a negative value, and may be measured according to any suitable method in the related art.

In an embodiment, an absolute value of a difference between the LUMO energy level of the first compound and the LUMO energy level of the second compound may be in a range of about 0.1 eV to about 1.0 eV, an absolute value of a difference between the LUMO energy level of the first compound and the LUMO energy level of the third compound may be in a range of about 0.1 eV to about 1.0 eV, an absolute value of a difference between the HOMO energy level of the first compound and the HOMO energy level of the second compound may be equal to or less than about 1.25 eV (e.g., in a range of about 0.2 eV to about 1.25 eV), and an absolute value of a difference between the HOMO energy level of the first compound and the HOMO energy level of the third compound may be equal to or less than about 1.25 eV (e.g., in a range of about 0.2 eV to about 1.25 eV).

When the relationships between the LUMO energy level and the HOMO energy level satisfy the conditions described above, a balance between holes and electrons injected into the emission layer may be obtained.

The light-emitting device may have a structure described in a first embodiment or a second embodiment.

Descriptions of First Embodiment

According to a first embodiment, the first compound may be included in an emission layer in an interlayer of a light-emitting device, wherein the emission layer may further include a host, the first compound may be different from the host, and the emission layer may emit phosphorescence or fluorescence from the first compound. For example, according to the first embodiment, the first compound may be a dopant or an emitter. In an embodiment, the first compound may be a phosphorescent dopant or a phosphorescence emitter.

Phosphorescence or fluorescence emitted from the first compound may be blue light.

The emission layer may further include an auxiliary dopant. The auxiliary dopant may serve to improve luminescence efficiency from the first compound by effectively transferring energy to a dopant or to the first compound as an emitter.

The auxiliary dopant may be different from the first compound and the host.

In an embodiment, the auxiliary dopant may be a delayed fluorescence-emitting compound.

In an embodiment, the auxiliary dopant may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.

Description of Second Embodiment

According to a second embodiment, the first compound may be included in an emission layer in an interlayer of a light-emitting device, wherein the emission layer may further include a host and a dopant, the first compound may be different from the host and the dopant, and the emission layer may emit phosphorescence or fluorescence (e.g., delayed fluorescence) from the dopant.

In an embodiment, the first compound in the second embodiment may serve as an auxiliary dopant that transfers energy to a dopant (or an emitter), and may not serve as a dopant.

In an embodiment, the first compound in the second embodiment may serve as an emitter and as an auxiliary dopant that transfers energy to a dopant (or to an emitter).

In an embodiment, phosphorescence or fluorescence emitted from the dopant (or the emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (e.g., blue delayed fluorescence).

The dopant (or the emitter) in the second embodiment may be a phosphorescent dopant material (e.g., the organometallic compound represented by Formula 1, the organometallic compound represented by Formula 401, or any combination thereof) or any fluorescent dopant material (e.g., the compound represented by Formula 501, the compound represented by Formula 502, the compound represented by Formula 503, or any combination thereof).

The blue light of the first embodiment and of the second embodiment may be blue light having a maximum emission wavelength in a range of about 430 nm to about 480 nm. For example, the blue light may have a maximum emission wavelength in a range of about 430 nm to about 475 nm. For example, the blue light may have a maximum emission wavelength in a range of about 440 nm to about 475 nm. For example, the blue light may have a maximum emission wavelength in a range of about 455 nm to about 470 nm.

The auxiliary dopant in the first embodiment may include, for example, the fourth compound represented by Formula 502 or 503.

The host in the first embodiment and in the second embodiment may be any host material (e.g., a compound represented by Formula 301, a compound represented by 301-1, a compound represented by Formula 301-2, or any combination thereof).

In an embodiment, the host in the first embodiment and in the second embodiment may be the second compound, the third compound, or any combination thereof, as described herein.

According to embodiments, provided is an electronic apparatus which may include the light-emitting device. The electronic apparatus may further include a thin-film transistor. In an embodiment, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, wherein the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode.

In an embodiment, the electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.

In an embodiment, the electronic apparatus may further include a color filter, a quantum dot color conversion layer, a touchscreen layer, a polarizing layer, or any combination thereof. The quantum dot color conversion layer may be a quantum dot-containing color conversion layer including quantum dots.

Further details on the electronic apparatus are as described in the specification.

According to embodiments, provided is a consumer product which may include the light-emitting device.

In an embodiment, the consumer product may be one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a light for signal, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality or augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a signboard.

According to embodiments, provided is the organometallic compound represented by Formula 1. Formula 1 is the same as described herein.

[Description of FIG. 1]

FIG. 1 is a schematic cross-sectional view of a light-emitting device 10 according to an embodiment. The light-emitting device 10 includes a first electrode 110, an interlayer 130, and a second electrode 150.

Hereinafter, a structure of the light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10 will be described in connection with FIG. 1.

[First Electrode 110]

In FIG. 1, a substrate may be further included under the first electrode 110 or above the second electrode 150. The substrate may be a glass substrate or a plastic substrate. In an embodiment, the substrate may be a flexible substrate, and may include plastics with excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high work function material that facilitates injection of holes.

The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), or any combination thereof. In an embodiment, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof.

The first electrode 110 may have a structure consisting of a single layer or a structure including multiple layers. In an embodiment, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.

[Interlayer 130]

The interlayer 130 may be located on the first electrode 110. The interlayer 130 may include an emission layer.

The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150.

The interlayer 130 may further include metal-containing compounds such as organometallic compounds, inorganic materials such as quantum dots, or the like, in addition to various organic materials.

In an embodiment, the interlayer 130 may include two or more emitting units stacked between the first electrode 110 and the second electrode 150, and at least one charge generation layer located between the two or more emitting units. When the interlayer 130 includes the two or more emitting units and the at least one charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.

[Hole Transport Region in Interlayer 130]

The hole transport region may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer consisting of different materials, or a structure including multiple layers including different materials.

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

For example, the hole transport region may have a multi-layered structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein the layers of each structure may be stacked from the first electrode 110 in its respective stated order, but the structure of the hole transport region is not limited thereto.

The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

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In Formulae 201 and 202,

L₂₀₁to L₂₀₄may each independently be a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

L₂₀₅may be *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a C₁-C₂₀alkylene group that is unsubstituted or substituted with at least one R_10a, a C₂-C₂₀alkenylene group that is unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, or a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

xa1 to xa4 may each independently be an integer from 0 to 5,

xa5 may be an integer from 1 to 10,

R₂₀₁to R₂₀₄and Q₂₀₁may each independently be a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, or a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

R₂₀₁and R₂₀₂may optionally be linked to each other, via a single bond, a C₁-C₅alkylene group that is unsubstituted or substituted with at least one R_10a, or a C₂-C₅alkenylene group that is unsubstituted or substituted with at least one R_10a, to form a C₈-C₆₀polycyclic group (for example, a carbazole group or the like) unsubstituted or substituted with at least one R_10a(for example, Compound HT16),

R₂₀₃and R₂₀₄may optionally be linked to each other via a single bond, a C₁-C₅alkylene group that is unsubstituted or substituted with at least one R_10a, or a C₂-C₅alkenylene group that is unsubstituted or substituted with at least one R_10a, to form a C₈-C₆₀polycyclic group that is unsubstituted or substituted with at least one R_10a, and

na1 may be an integer from 1 to 4.

In an embodiment, each of Formulae 201 and 202 may include at least one of groups represented by Formulae CY201 to CY217:

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In Formulae CY201 to CY217, R_10band R_10cmay each independently be the same as described with respect to R_10a, ring CY₂₀₁to ring CY₂₀₄may each independently be a C₃-C₂₀carbocyclic group or a C₁-C₂₀heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R_10aas described herein.

In an embodiment, in Formulae CY201 to CY217, ring CY₂₀₁to ring CY₂₀₄may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.

In an embodiment, each of Formulae 201 and 202 may include at least one of groups represented by Formulae CY201 to CY203.

In an embodiment, Formula 201 may include at least one of groups represented by Formulae CY201 to CY203 and at least one of groups represented by Formulae CY204 to CY217.

In an embodiment, in Formula 201, xa1 may be 1, R₂₀₁may be a group represented by one of Formulae CY201 to CY203, xa2 may be 0, and R₂₀₂may be a group represented by one of Formulae CY204 to CY207.

In an embodiment, each of Formulae 201 and 202 may not include groups represented by Formulae CY201 to CY203.

In an embodiment, each of Formulae 201 and 202 may not include groups represented by Formulae CY201 to CY203, and may include at least one of groups represented by Formulae CY204 to CY217.

In an embodiment, each of Formulae 201 and 202 may not include groups represented by Formulae CY201 to CY217.

In an embodiment, the hole transport region may include one of Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), p-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzene sulfonic acid (PANI/DBSA), poly(3,4-ethylene dioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrene sulfonate) (PANI/PSS), or any combination thereof:

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A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å. For example, the thickness of the hole transport region may be in a range of about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å. For example, the thickness of the hole injection layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the hole transport layer may be in a range of 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 these ranges, satisfactory hole-transporting characteristics may be obtained without a substantial increase in driving voltage.

The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance of a wavelength of light emitted by an emission layer, and the electron blocking layer may block the leakage of electrons from an emission layer to a hole transport region. Materials that may be included in the hole transport region may be included in the emission auxiliary layer and the electron blocking layer.

[p-Dopant]

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 uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer consisting of a charge-generation material).

The charge-generation material may be, for example, a p-dopant.

In an embodiment, a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be equal to or less than about −3.5 eV.

In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound containing an element EL1 and an element EL2, or any combination thereof.

Examples of the quinone derivative may include TCNQ, F4-TCNQ, and the like.

Examples of the cyano group-containing compound may include HAT-CN, a compound represented by Formula 221, and the like.

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In Formula 221,

R₂₂₁to R₂₂₃may each independently be a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a, and

at least one of R₂₂₁to R₂₂₃may each independently be a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group, each substituted with: a cyano group; —F; —Cl; —Br; —I; a C₁-C₂₀alkyl group substituted with a cyano group, —F, —Cl, —Br, —I, or any combination thereof; or any combination thereof.

In the compound containing the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or a combination thereof, and the element EL2 may be a non-metal, a metalloid, or a combination thereof.

Examples of the metal may include: an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (for example, titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); a post-transition metal (for example, zinc (Zn), indium (In), tin (Sn), etc.); and a lanthanide metal (for example, lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).

Examples of the metalloid may include silicon (Si), antimony (Sb), and tellurium (Te).

Examples of the non-metal may include oxygen (O) and a halogen (for example, F, Cl, Br, I, etc.).

In an embodiment, examples of the compound containing element EL1 and element EL2 may include a metal oxide, a metal halide (for example, a metal fluoride, a metal chloride, a metal bromide, or a metal iodide), a metalloid halide (for example, a metalloid fluoride, a metalloid chloride, a metalloid bromide, or a metalloid iodide), a metal telluride, or any combination thereof.

Examples of the metal oxide may include tungsten oxide (for example, WO, W₂O₃, WO₂, WO₃, W₂O₅, etc.), vanadium oxide (for example, VO, V₂O₃, VO₂, V₂O₅, etc.), molybdenum oxide (MoO, Mo₂O₃, MoO₂, MoO₃, Mo₂O₅, etc.), and rhenium oxide (for example, ReO₃, etc.).

Examples of the metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, and a lanthanide metal halide.

Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.

Examples of the alkaline earth metal halide may include BeF₂, MgF₂, CaF₂, SrF₂, BaF₂, BeCl₂, MgCl₂, CaCl₂), SrCl₂, BaCl₂, BeBr₂, MgBr₂, CaBr₂, SrBr₂, BaBr₂, BeI₂, Mg₁₂, CaI₂, SrI₂, and BaI₂.

Examples of the transition metal halide may include a titanium halide (for example, TiF₄, TiCl₄, TiBr₄, TiI₄, etc.), a zirconium halide (for example, ZrF₄, ZrCl₄, ZrBr₄, ZrI₄, etc.), a hafnium halide (for example, HfF₄, HfCl₄, HfBr₄, HfI₄, etc.), a vanadium halide (for example, VF₃, VCl₃, VBr₃, VI₃, etc.), a niobium halide (for example, NbF₃, NbCl₃, NbBr₃, NbI₃, etc.), a tantalum halide (for example, TaF₃, TaCl₃, TaBr₃, TaI₃, etc.), a chromium halide (for example, CrF₃, CrCl₃, CrBr₃, CrI₃, etc.), a molybdenum halide (for example, MoF₃, MoCl₃, MoBr₃, MoI₃, etc.), a tungsten halide (for example, WF₃, WCl₃, WBr₃, WI₃, etc.), a manganese halide (for example, MnF₂, MnCl₂, MnBr₂, MnI₂, etc.), a technetium halide (for example, TcF₂, TcCl₂, TcBr₂, TcI₂, etc.), a rhenium halide (for example, ReF₂, ReCl₂, ReBr₂, ReI₂, etc.), an iron halide (for example, FeF₂, FeCl₂, FeBr₂, FeI₂, etc.), a ruthenium halide (for example, RuF₂, RuCl₂, RuBr₂, RuI₂, etc.), an osmium halide (for example, OsF₂, OSCl₂, OsBr₂, OSI₂, etc.), a cobalt halide (for example, CoF₂, COCl₂, CoBr₂, CoI₂, etc.), a rhodium halide (for example, RhF₂, RhCl₂, RhBr₂, RhI₂, etc.), an iridium halide (for example, IrF₂, IrCl₂, IrBr₂, IrI₂, etc.), a nickel halide (for example, NiF₂, NiCl₂, NiBr₂, NiI₂, etc.), a palladium halide (for example, PdF₂, PdCl₂, PdBr₂, PdI₂, etc.), a platinum halide (for example, PtF₂, PtCl₂, PtBr₂, PtI₂, etc.), a copper halide (for example, CuF, CuCl, CuBr, CuI, etc.), a silver halide (for example, AgF, AgCl, AgBr, AgI, etc.), and a gold halide (for example, AuF, AuCl, AuBr, AuI, etc.).

Examples of the post-transition metal halide may include a zinc halide (for example, ZnF₂, ZnCl₂, ZnBr₂, ZnI₂, etc.), an indium halide (for example, InI₃, etc.), and a tin halide (for example, SnI₂, etc.).

Examples of the lanthanide metal halide may include YbF, YbF₂, YbF₃, SmF₃, YbCl, YbCl₂, YbCl₃, SmCl₃, YbBr, YbBr₂, YbBr₃, SmBr₃, YbI, YbI₂, YbI₃, and SmI₃.

Examples of the metalloid halide may include an antimony halide (for example, SbCl₅, etc.).

Examples of the metal telluride may include an alkali metal telluride (for example, Li₂Te, Na₂Te, K₂Te, Rb₂Te, Cs₂Te, etc.), an alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a transition metal telluride (for example, TiTe₂, ZrTe₂, HfTe₂, V₂Te₃, Nb₂Te₃, Ta₂Te₃, Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu₂Te, CuTe, Ag₂Te, AgTe, Au₂Te, etc.), a post-transition metal telluride (for example, ZnTe, etc.), and a lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).

[Emission Layer in Interlayer 130]

When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a subpixel. In an embodiment, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers may contact each other or may be separated from each other. In an embodiment, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.

The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

An amount of the dopant in the emission layer may be about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the host.

In an embodiment, the emission layer may include a quantum dot.

In an embodiment, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may serve as a host or as a dopant in the emission layer.

A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the emission layer may be in a range of about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.

[Host]

The host in the emission layer may include the second compound or the third compound as described in the specification, or any combination thereof.

In an embodiment, the host may include a compound represented by Formula 301:

[Ar₃₀₁]_xb11-[(L₃₀₁)_xb1-R₃₀₁]_xb21 [Formula 301]

In Formula 301,

Ar₃₀₁and L₃₀₁may each independently be a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

xb11 may be 1, 2, or 3,

xb1 may be an integer from 0 to 5,

R₃₀₁may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group that is unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group that is unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group that is unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group that is unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂), —B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), or —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5, and

Q₃₀₁to Q₃₀₃may each independently be the same as described in connection with Q₁.

In an embodiment, in Formula 301, when xb11 is 2 or more, two or more Ar₃₀₁(s) may be linked to each other via a single bond.

In an embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:

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In Formulae 301-1 and 301-2,

ring A301 to ring A304 may each independently be a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

X₃₀₁may be O, S, N—[(L₃₀₄)_xb4-R₃₀₄], C(R₃₀₄)(R₃₀₅), or Si(R₃₀₄)(R₃₀₅),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, and R₃₀₁may each be the same as described herein,

L₃₀₂to L₃₀₄may each independently be the same as described in connection with L₃₀₁,

xb2 to xb4 may each independently be the same as described in connection with xb1, and

R₃₀₂to R₃₀₅and R₃₁₁to R₃₁₄may each independently be the same as described in connection with R₃₀₁.

In an embodiment, the host may include an alkali earth metal complex, a post-transition metal complex, or a combination thereof. In an embodiment, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or a combination thereof.

In an embodiment, the host may include one of Compounds H1 to H124, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof:

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In an embodiment, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.

The host may have various modifications. In an embodiment, the host may include only one kind of compound, or may include two or more kinds of different compounds.

[Phosphorescent Dopant]

The emission layer may include the first compound as described in the specification, as a phosphorescent dopant.

In an embodiment, when the emission layer includes the first compound as described herein and the first compound serves as an auxiliary dopant, the emission layer may include a phosphorescent dopant.

The phosphorescent dopant may include at least one transition metal as a central metal.

The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.

The phosphorescent dopant may be electrically neutral.

In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:

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In Formulae 401 and 402,

M may be a transition metal (for example, iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),

L₄₀₁may be a ligand represented by Formula 402, and xc1 may be 1, 2, or 3, wherein when xc1 is two or more, two or more L₄₀₁(s) may be identical to or different from each other,

L₄₀₂may be an organic ligand, and xc2 may be 0, 1, 2, 3, or 4, wherein when xc2 is 2 or more, two or more L₄₀₂(s) may be identical to or different from each other,

X₄₀₁and X₄₀₂may each independently be nitrogen or carbon,

ring A₄₀₁and ring A₄₀₂may each independently be a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group,

T₄₀₁may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)-*′, *—C(Q₄₁₁)(Q₄₁₂)-*′, *—C(Q₄₁₁)=C(Q₄₁₂)-*′, *—C(Q₄₁₁)=*′, or *═C═*′,

X₄₀₃and X₄₀₄may each independently be a chemical bond (for example, a covalent bond or a coordinate bond), O, S, N(Q₄₁₃), B(Q₄₁₃), P(Q₄₁₃), C(Q₄₁₃)(Q₄₁₄), or Si(Q₄₁₃)(Q₄₁₄),

Q₄₁₁to Q₄₁₄may each independently be the same as described in connection with Q₁,

R₄₀₁and R₄₀₂may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group that is unsubstituted or substituted with at least one R_10a, a C₁-C₂₀alkoxy group that is unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), or —P(═O)(Q₄₀₁)(Q₄₀₂),

Q₄₀₁to Q₄₀₃may each independently be the same as described in connection with Q₁,

xc11 and xc12 may each independently be an integer from 0 to 10, and

* and *′ in Formula 402 each indicate a binding site to M in Formula 401.

In an embodiment, in Formula 402, X₄₀₁may be nitrogen and X₄₀₂may be carbon, or each of X₄₀₁and X₄₀₂may be nitrogen.

In an embodiment, in Formula 401, when xc1 is 2 or more, two ring A401 in two or more L₄₀₁(s) may be optionally linked to each other via T₄₀₂, which is a linking group, and two ring A₄₀₂may optionally be linked to each other via T₄₀₃, which is a linking group (see Compounds PD1 to PD4 and PD7). T₄₀₂and T₄₀₃may each independently be the same as described in connection with T₄₀₁.

In Formula 401, L₄₀₂may be an organic ligand. In an embodiment, L₄₀₂may include a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, etc.), or any combination thereof.

The phosphorescent dopant may include, for example, one of Compounds PD1 to PD39, or any combination thereof:

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[Fluorescent Dopant]

When the emission layer includes the first compound as described in the specification and the first compound serves as an auxiliary dopant, the emission layer may further include a fluorescent dopant.

In an embodiment, when the emission layer includes the first compound as described in the specification and the first compound serves as a phosphorescent dopant, the emission layer may further include an auxiliary dopant.

The fluorescent dopant and the auxiliary dopant may each independently include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.

In an embodiment, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by Formula 501:

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In Formula 501,

Ar₅₀₁, L₅₀₁to L₅₀₃, R₅₀₁, and R₅₀₂may each independently be a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

xd1 to xd3 may each independently be 0, 1, 2, or 3, and

xd4 may be 1, 2, 3, 4, 5, or 6.

In an embodiment, in Formula 501, Ar₅₀₁may be a condensed cyclic group (for example, an anthracene group, a chrysene group, or a pyrene group) in which three or more monocyclic groups are condensed together.

In an embodiment, in Formula 501, xd4 may be 2.

In an embodiment, the fluorescent dopant and the auxiliary dopant may each independently include one of Compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:

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In an embodiment, the fluorescent dopant and the auxiliary dopant may each independently include the fourth compound represented by Formula 502 or 503 as described herein.

[Delayed Fluorescence Material]

The emission layer may include, as a delayed fluorescence material, the fourth compound as described herein.

In an embodiment, the emission layer may include the fourth compound, and may further include a delayed fluorescence material.

In the specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.

The delayed fluorescence material included in the emission layer may serve as a host or as a dopant, depending on the type of other materials included in the emission layer.

In an embodiment, a difference between the triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be greater than or equal to 0 eV and less than or equal to 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material satisfies the above-described range, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials may effectively occur, and thus, the luminescence efficiency of the light-emitting device 10 may be improved.

In an embodiment, the delayed fluorescence material may include: a material including at least one electron donor (for example, a π electron-rich C₃-C₆₀cyclic group, such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, or a π electron-deficient nitrogen-containing C₁-C₆₀cyclic group); or a material including a C₈-C₆₀polycyclic group in which two or more cyclic groups are condensed while sharing boron (B).

Examples of the delayed fluorescence material may include at least one of Compounds DF1 to DF9:

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[Quantum Dot]

The emission layer may include a quantum dot.

In the specification, a quantum dot may be a crystal of a semiconductor compound, and may include any material capable of emitting light of various emission wavelengths according to a size of the crystal.

A diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.

The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.

According to the wet chemical process, a precursor material is mixed with an organic solvent to grow a quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles may be controlled through a process which may be more readily performed than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE), and which requires low costs.

The quantum dot may include a Group II-VI semiconductor compound, a Group III-V semiconductor compound, a Group III-VI semiconductor compound, a Group I-III-VI semiconductor compound, a Group IV-VI semiconductor compound, a Group IV element or compound, or any combination thereof.

Examples of the Group II-VI semiconductor compound may include: a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; or any combination thereof.

Examples of the Group III-V semiconductor compound may include: a binary compound, such as GaN, GaP, GaAs, GaSbAlN, AlP, AlAs, AlSbInN, InP, InAs, or InSb; a ternary compound, such as GaNP, GaNAs, GaNSbGaPAs, GaPSbAlNP, AlNAs, AlNSbAlPAs, AlPSbInGaP, InNP, InAlP, InNAs, InNSbInPAs, or InPSb; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSbGaAlPAs, GaAlPSb GaInNP, GaInNAs, GalnNSbGaInPAs, GaInPSbInAlNP, InAlNAs, InAlNSbInAlPAs, or InAlPSb; or any combination thereof. In an embodiment, the Group III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including a Group II element may include InZnP, InGaZnP, InAlZnP, and the like.

Examples of the Group III-VI semiconductor compound may include: a binary compound, such as GaS, GaSe, Ga₂Se₃, GaTe, InS, InSe, In₂S₃, In₂Se₃, or InTe; a ternary compound, such as InGaS₃, or InGaSe₃; or any combination thereof.

Examples of the Group I-III-VI semiconductor compound may include: a ternary compound, such as AgInS, AgInS₂, CuInS, CuInS₂, CuGaO₂, AgGaO₂, or AgAlO₂; or any combination thereof.

Examples of the Group IV-VI semiconductor compound may include: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, or the like; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, or the like; a quaternary compound, such as SnPbSSe, SnPbSeTe, SnPbSTe, or the like; or any combination thereof.

Examples of the Group IV element or compound may include: a single element material, such as Si or Ge; a binary compound, such as SiC or SiGe; or any combination thereof.

Each element included in a multi-element compound such as a binary compound, a ternary compound, or a quaternary compound, may exist in a particle at a uniform concentration or at a non-uniform concentration.

In an embodiment, the quantum dot may have a single structure or a core-shell structure. In the case of the quantum dot having a single structure, the concentration of each element included in the quantum dot may be uniform. In the case of the quantum dot having a core-shell structure, a material included in the core and a material included in the shell may be different from each other.

The shell of the quantum dot may serve as a protective layer to prevent chemical degeneration of the core to maintain semiconductor characteristics and/or may serve as a charging layer to impart electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. An interface between the core and the shell of the quantum dot may have a concentration gradient in which the concentration of a material that is present in the shell decreases toward the core.

Examples of the shell of the quantum dot may include a metal oxide, a metalloid oxide, a non-metal oxide, a semiconductor compound, and any combination thereof. Examples of the metal oxide, the metalloid oxide, or the non-metal oxide may include: a binary compound, such as SiO₂, Al₂O₃, TiO₂, ZnO, MnO, Mn₂O₃, Mn₃O₄, CuO, FeO, Fe₂O₃, Fe₃O₄, CoO, Co₃O₄, or NiO; a ternary compound, such as MgAl₂O₄, CoFe₂O₄, NiFe₂O₄, or CoMn₂O₄; or any combination thereof. Examples of the semiconductor compound may include, as described herein, a Group II-VI semiconductor compound, a Group III-V semiconductor compound, a Group III-VI semiconductor compound, a Group I-III-VI semiconductor compound, a Group IV-VI semiconductor compound, or any combination thereof. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSbHgS, HgSe, HgTe, InAs, InP, InGaP, InSbAlAs, AlP, AlSb or any combination thereof.

A full width at half maximum (FWHM) of an emission wavelength spectrum of the quantum dot may be equal to or less than about 45 nm. For example, a FWHM of an emission wavelength spectrum of the quantum dot may be equal to or less than about 40 nm. For example, a FWHM of an emission wavelength spectrum of the quantum dot may be equal to or less than about 30 nm. Within these ranges, color purity or color reproducibility may be increased. Light emitted through the quantum dot may be emitted in all directions, so that a wide viewing angle can be improved.

The quantum dot may be a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, or a nanoplate particle.

Since the energy band gap can be adjusted by controlling the size of the quantum dot, light having various wavelength bands can be obtained from the quantum dot emission layer. Therefore, by utilizing quantum dots of different sizes, a light-emitting device that emits light of various wavelengths may be implemented. In an embodiment, the size of the quantum dot may be selected to emit red, green, and/or blue light. For examples, the size of the quantum dot may be configured to emit white light by combining light of various colors.

[Electron Transport Region in Interlayer 130]

The electron transport region may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer consisting of different materials, or a structure including multiple layers including different materials.

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

For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein the layers of each structure may be stacked from an emission layer in its respective stated order, but the structure of the electron transport region is not limited thereto.

In an embodiment, the electron transport region (for example, the buffer layer, the hole-blocking layer, the electron control layer, or the electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C₁-C₆₀cyclic group.

In an embodiment, the electron transport region may include a compound represented by Formula 601.

[Ar₆₀₁]_xe11-[(L₆₀₁)_xe1-R₆₀₁]_xe21 [Formula 601]

In Formula 601,

Ar₆₀₁and L₆₀₁may each independently be a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

xe11 may be 1, 2, or 3,

xe1 may be 0, 1, 2, 3, 4, or 5,

R₆₀₁may be a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃₎, —C(═O)(Q₆₀₁₎, —S(═O)₂(Q₆₀₁₎, or —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁to Q₆₀₃may each independently be the same as described in connection with Q₁,

xe21 may be 1, 2, 3, 4, or 5, and

at least one of Ar₆₀₁, L₆₀₁, and R₆₀₁may each independently be a π electron-deficient nitrogen-containing C₁-C₆₀cyclic group that is unsubstituted or substituted with at least one R_10a.

In an embodiment, in Formula 601, when xe11 is 2 or more, two or more Ar₆₀₁(s) may be linked to each other via a single bond.

In an embodiment, in Formula 601, Ar₆₀₁may be a substituted or unsubstituted anthracene group.

In an embodiment, the electron transport region may include a compound represented by Formula 601-1:

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In Formula 601-1,

X₆₁₄may be N or C(R₆₁₄), X₆₁₅may be N or C(R₆₁₅), X₆₁₆may be N or C(R₆₁₆), and at least one of X₆₁₄to X₆₁₆may be N,

L₆₁₁to L₆₁₃may each independently be the same as described in connection with L₆₀₁,

xe611 to xe613 may each independently be the same as described in connection with xe1,

R₆₁₁to R₆₁₃may each independently be the same as described in connection with R₆₀₁, and

R₆₁₄to R₆₁₆may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₃-C₆₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, or a C₁-C₆₀heterocyclic group that is unsubstituted or substituted with at least one R_10a.

In an embodiment, in Formulae 601 and 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.

The electron transport region may include one of Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq, TAZ, NTAZ, or any combination thereof:

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A thickness of the electron transport region may be in a range of about 100 Å to about 5,000 Å. For example, the thickness of the electron transport region may be in a range of about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, a thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, and a thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 30 Å to about 300 Å. For example, the thickness of the electron transport layer may be in a range of about 150 Å to about 500 Å. When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.

The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.

The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or with the metal ion of the alkaline earth-metal complex may each independently include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.

In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or Compound ET-D2:

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The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.

The electron injection layer may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer consisting of different materials, or a structure including multiple layers including different materials.

The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may include oxides, halides (for example, fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.

The alkali metal-containing compound may include: alkali metal oxides, such as Li₂O, Cs₂O, or K₂O; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI; or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, Ba_xSr_1-xO (x is a real number satisfying the condition of 0<x<1), Ba_xCa_1-xO (x is a real number satisfying the condition of 0<x<1), or the like. The rare earth metal-containing compound may include YbF₃, ScF₃, Sc₂O₃, Y₂O₃, Ce₂O₃, GdF₃, TbF₃, YbI₃, ScI₃, TbI₃, or any combination thereof. In an embodiment, the rare earth metal-containing compound may include a lanthanide metal telluride. Examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La₂Te₃, Ce₂Te₃, Pr₂Te₃, Nd₂Te₃, Pm₂Te₃, Sm₂Te₃, Eu₂Te₃, Gd₂Te₃, Tb₂Te₃, Dy₂Te₃, Ho₂Te₃, Er₂Te₃, Tm₂Te₃, Yb₂Te₃, and Lu₂Te₃.

The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include one of ions of the alkali metal, ions of the alkaline earth metal, and ions of the rare earth metal, and a ligand bonded to the metal ion (for example, a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenyl benzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof).

The electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In an embodiment, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).

In an embodiment, the electron injection layer may consist of an alkali metal-containing compound (for example, an alkali metal halide); or the electron injection layer may consist of an alkali metal-containing compound (for example, an alkali metal halide), and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, a RbI:Yb co-deposited layer, a LiF:Yb co-deposited, or the like.

When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.

A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å. For example, the thickness of the electron injection layer may be in a range of about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.

[Second Electrode 150]

The second electrode 150 may be located on the interlayer 130 having such a structure. The second electrode 150 may be a cathode, which is an electron injection electrode. The second electrode 150 may include a material having a low-work function, for example, a metal, an alloy, an electrically conductive compound, or any combination thereof.

In an embodiment, the second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, or a combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 150 may have a single-layered structure or a multi-layered structure.

[Capping Layer]

The light-emitting device 10 may include a first capping layer located outside the first electrode 110, and/or a second capping layer located outside the second electrode 150. For example, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked in this stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in this stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in this stated order.

Light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110, which may be a semi-transmissive electrode or a transmissive electrode, and through the first capping layer. Light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150, which may be a semi-transmissive electrode or a transmissive electrode, and through the second capping layer.

The first capping layer and the second capping layer may each increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 may be increased, so that the emission efficiency of the light-emitting device 10 may be improved.

The first capping layer and the second capping layer may each include a material having a refractive index equal to or greater than about 1.6 (with respect to a wavelength of about 589 nm).

The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.

At least one of the first capping layer and the second capping layer may each independently include carbocyclic compounds, heterocyclic compounds, amine group-containing compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may be optionally substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.

In an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amine group-containing compound.

In an embodiment, at least one of the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

In an embodiment, at least one of the first capping layer and the second capping layer may each independently include one of Compounds HT28 to HT33, one of Compounds CP1 to CP6, β-NPB, or any combination thereof:

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[Film]

The organometallic compound represented by Formula 1 may be included in various films. According to embodiments, a film including an organometallic compound represented by Formula 1 may be provided. The film may be, for example, an optical member (or a light control means) (for example, a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, or like), a light-blocking member (for example, a light reflective layer, a light absorbing layer, or the like), a protective member (for example, an insulating layer, a dielectric layer, or the like).

[Electronic Apparatus]

The light-emitting device may be included in various electronic apparatuses. In an embodiment, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, or the like.

The electronic apparatus (for example, a light-emitting apparatus) may further include, in addition to the light-emitting device, a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and/or the color conversion layer may be located in at least one traveling direction of light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be the same as described herein.

In an embodiment, the color conversion layer may include quantum dots. The quantum dot may be, for example, a quantum dot as described herein.

The electronic apparatus may include a first substrate. The first substrate may include subpixels, the color filter may include color filter areas respectively corresponding to the subpixels, and the color conversion layer may include color conversion areas respectively corresponding to the subpixels.

A pixel-defining layer may be located between the subpixels to define each subpixel.

The color filter may further include color filter areas and light-shielding patterns located between the color filter areas, and the color conversion layer may include color conversion areas and light-shielding patterns located between the color conversion areas.

The color filter areas (or the color conversion areas) may include a first area emitting first color light, a second area emitting second color light, and/or a third area emitting third color light, and the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths from one another. In an embodiment, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the color filter areas (or the color conversion areas) may include quantum dots. For example, the first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include a quantum dot. The quantum dot may be the same as described herein. The first area, the second area, and/or the third area may each further include a scatterer.

In an embodiment, the light-emitting device may emit first light, the first area may absorb the first light to emit first-first color light, the second area may absorb the first light to emit second-first color light, and the third area may absorb the first light to emit third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths.

For example, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.

The electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device as described herein. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light-emitting device.

The thin-film transistor may further include a gate electrode, a gate insulating film, etc.

The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.

The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be located between the color filter and/or the color conversion layer, and the light-emitting device. The sealing portion may allow light from the light-emitting device to be extracted to the outside, and may simultaneously prevent ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including an organic layer and/or an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic apparatus may be flexible.

Various functional layers may be further included on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the use of the electronic apparatus. Examples of the functional layers may include a touch screen layer, a polarizing layer, an authentication apparatus, and the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by utilizing biometric information of a living body (for example, fingertips, pupils, etc.).

The authentication apparatus may further include, in addition to the light-emitting device, a biometric information collector.

The electronic apparatus may be applied to various displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic diaries, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and the like.

[Description of FIGS. 2 and 3]

FIG. 2 is a schematic cross-sectional view of an electronic apparatus according to an embodiment.

The electronic apparatus of FIG. 2 includes a substrate 100, a thin-film transistor (TFT), a light-emitting device, and an encapsulation portion 300 that seals the light-emitting device.

The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be formed on the substrate 100. The buffer layer 210 may prevent penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.

A TFT may be located on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.

A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be located on the active layer 220, and the gate electrode 240 may be located on the gate insulating film 230.

An interlayer insulating film 250 is located on the gate electrode 240. The interlayer insulating film 250 may be placed between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.

The source electrode 260 and the drain electrode 270 may be located on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may respectively contact the exposed portions of the source region and the drain region of the active layer 220.

The TFT is electrically connected to a light-emitting device to drive the light-emitting device, and is covered by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light-emitting device is provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.

The first electrode 110 may be formed on the passivation layer 280. The passivation layer 280 does not completely cover the drain electrode 270 and may expose a portion of the drain electrode 270, and the first electrode 110 is electrically connected to the exposed portion of the drain electrode 270.

A pixel-defining layer 290 containing an insulating material may be located on the first electrode 110. The pixel-defining layer 290 may expose a region of the first electrode 110, and an interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel-defining layer 290 may be a polyimide or polyacrylic organic film. Although not shown in FIG. 2, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel-defining layer 290 to be provided in the form of a common layer.

The second electrode 150 may be located on the interlayer 130, and a capping layer 170 may be further included on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

The encapsulation portion 300 may be located on the capping layer 170. The encapsulation portion 300 may be located on a light-emitting device to protect the light-emitting device from moisture and/or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), or the like), or a combination thereof; or a combination of the inorganic film and the organic film.

FIG. 3 is a schematic cross-sectional view of an electronic apparatus according to another embodiment.

The electronic apparatus of FIG. 3 may differ from the electronic apparatus of FIG. 2, at least in that a light-shielding pattern 500 and a functional region 400 are further included on the encapsulation portion 300. The functional region 400 may be a color filter area, a color conversion area, or a combination of the color filter area and the color conversion area. In an embodiment, the light-emitting device included in the electronic apparatus of FIG. 3 may be a tandem light-emitting device.

[Manufacturing Method]

Respective layers included in the hole transport region, the emission layer, and respective layers included in the electron transport region may be formed in a certain region by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging.

When layers constituting the hole transport region, an emission layer, and layers constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10⁻⁸torr to about 10⁻³torr, and a deposition speed of about 0.01 Å/sec to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed.

Definitions of Terms

The term “C₃-C₆₀carbocyclic group” as used herein may be a cyclic group consisting of carbon as the only ring-forming atoms and having three to sixty carbon atoms, and the term “C₁-C₆₀heterocyclic group” as used herein may be a cyclic group that has one to sixty carbon atoms and further has, in addition to carbon, at least one heteroatom as a ring-forming atom. The C₃-C₆₀carbocyclic group and the C₁-C₆₀heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. In an embodiment, the C₁-C₆₀heterocyclic group may have 3 to 61 ring-forming atoms.

The term “cyclic group” as used herein may include the C₃-C₆₀carbocyclic group or the C₁-C₆₀heterocyclic group.

The term “π electron-rich C₃-C₆₀cyclic group” as used herein may be a cyclic group that has three to sixty carbon atoms and may not include *—N═*′ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C₁-C₆₀cyclic group” as used herein may be a heterocyclic group that has one to sixty carbon atoms and may include *—N═*′ as a ring-forming moiety.

In embodiments,

the C₃-C₆₀carbocyclic group may be a T1 group or a cyclic group in which two or more T1 groups are condensed with each other (for example, a cyclopentadiene group, an adamantane group, a norbornane group, a benzene group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a pentaphene group, a heptalene group, a naphthacene group, a picene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indenophenanthrene group, or an indenoanthracene group),

the C₁-C₆₀heterocyclic group may be a T2 group, a cyclic group in which two or more T2 groups are condensed with each other, or a cyclic group in which at least one T2 group and at least one T1 group are condensed with each other (for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.),

the π electron-rich C₃-C₆₀cyclic group may be a T1 group, a cyclic group in which two or more T1 groups are condensed with each other, a T3 group, a cyclic group in which two or more T3 groups are condensed with each other, or a cyclic group in which at least one T3 group and at least one T1 group are condensed with each other (for example, the C₃-C₆₀carbocyclic group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, etc.),

the π electron-deficient nitrogen-containing C₁-C₆₀cyclic group may be a T4 group, a cyclic group in which two or more T4 groups are condensed with each other, a cyclic group in which at least one T4 group and at least one T1 group are condensed with each other, a cyclic group in which at least one T4 group and at least one T3 group are condensed with each other, or a cyclic group in which at least one T4 group, at least one T1 group, and at least one T3 group are condensed with one another (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.),

wherein the T1 group may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or a bicyclo[2.2.1]heptane) 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, or a benzene group,

the T2 group may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidine group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group, or a dihydropyridazine group,

the T3 group may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group, and

the T4 group may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.

The terms “cyclic group”, “C₃-C₆₀carbocyclic group”, “C₁-C₆₀heterocyclic group”, “π electron-rich C₃-C₆₀cyclic group”, or “π electron-deficient nitrogen-containing C₁-C₆₀cyclic group” as used herein may each be a group condensed to any cyclic group, a monovalent group, or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, etc.), depending on the structure of a formula in connection with which the terms are used. For example, a “benzene group” may be a benzo group, a phenyl group, a phenylene group, or the like, which may be readily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”

Examples of the monovalent C₃-C₆₀carbocyclic group and the monovalent C₁-C₆₀heterocyclic group may include a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and examples of the divalent C₃-C₆₀carbocyclic group and the divalent C₁-C₆₀heterocyclic group may include a C₃-C₁₀cycloalkylene group, a C₁-C₁₀heterocycloalkylene group, a C₃-C₁₀cycloalkenylene group, a C₁-C₁₀heterocycloalkenylene group, a C₆-C₆₀arylene group, a C₁-C₆₀heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

The term “C₁-C₆₀alkyl group” as used herein may be a linear or branched aliphatic hydrocarbon monovalent group that has one to sixty carbon atoms, and examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl 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 isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. The term “C₁-C₆₀alkylene group” as used herein may be a divalent group having a same structure as the C₁-C₆₀alkyl group.

The term “C₂-C₆₀alkenyl group” as used herein may be a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at a terminus of the C₂-C₆₀alkyl group, and examples thereof may include an ethenyl group, a propenyl group, and a butenyl group. The term “C₂-C₆₀alkenylene group” as used herein may be a divalent group having a same structure as the C₂-C₆₀alkenyl group.

The term “C₂-C₆₀alkynyl group” as used herein may be a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at a terminus of the C₂-C₆₀alkyl group, and examples thereof may include an ethynyl group and a propynyl group. The term “C₂-C₆₀alkynylene group” as used herein may be a divalent group having a same structure as the C₂-C₆₀alkynyl group.

The term “C₁-C₆₀alkoxy group” as used herein may be a monovalent group represented by —O(A₁₀₁) (wherein A₁₀₁may be a C₁-C₆₀alkyl group), and examples thereof may include a methoxy group, an ethoxy group, and an isopropyloxy group.

The term “C₃-C₁₀cycloalkyl group” as used herein may be a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof 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 (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. The term “C₃-C₁₀cycloalkylene group” as used herein may be a divalent group having a same structure as the C₃-C₁₀cycloalkyl group.

The term “C₁-C₁₀heterocycloalkyl group” as used herein may be a monovalent cyclic group that further includes, in addition to a carbon atom, at least one heteroatom as a ring-forming atom and has 1 to 10 carbon atoms, and examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C₁-C₁₀heterocycloalkylene group” as used herein may be a divalent group having a same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀cycloalkenyl group” as used herein may be a monovalent cyclic group that has three to ten carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof may include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁cycloalkenylene group” as used herein may be a divalent group having a same structure as the C₃-C₁₀cycloalkenyl group.

The term “C₁-C₁₀heterocycloalkenyl group” as used herein may be a monovalent cyclic group that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in the cyclic structure thereof. Examples of the C₁-C₁₀heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C₁-C₁₀heterocycloalkenylene group” as used herein may be a divalent group having a same structure as the C₁-C₁₀heterocycloalkenyl group.

The term “C₆-C₆₀aryl group” as used herein may be a monovalent group having a carbocyclic aromatic system having six to sixty carbon atoms, and the term “C₆-C₆₀arylene group” as used herein may be a divalent group having a carbocyclic aromatic system having six to sixty carbon atoms. Examples of the C₆-C₆₀aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group. When the C₆-C₆₀aryl group and the C₆-C₆₀arylene group each include two or more rings, the respective rings may be condensed with each other.

The term “C₁-C₆₀heteroaryl group” as used herein may be a monovalent group having a heterocyclic aromatic system that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, and 1 to 60 carbon atoms. The term “C₁-C₆₀heteroarylene group” as used herein may be a divalent group having a heterocyclic aromatic system that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, and 1 to 60 carbon atoms. Examples of the C₁-C₆₀heteroaryl group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀heteroarylene group each include two or more rings, the respective rings may be condensed with each other.

The term “monovalent non-aromatic condensed polycyclic group” as used herein may be a monovalent group having two or more rings condensed to each other, only carbon atoms (for example, having 8 to 60 carbon atoms) as ring-forming atoms, and non-aromaticity in its molecular structure when considered as a whole. Examples of the monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and an indeno anthracenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein may be a divalent group having a same structure as a monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein may be a monovalent group having two or more rings condensed to each other, at least one heteroatom other than carbon atoms (for example, having 1 to 60 carbon atoms), as a ring-forming atom, and non-aromaticity in its molecular structure when considered as a whole. Examples of the monovalent non-aromatic condensed heteropolycyclic group may include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphtho indolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein may be a divalent group having a same structure as a monovalent non-aromatic condensed heteropolycyclic group.

The term “C₆-C₆₀aryloxy group” as used herein may be a group represented by —O(A₁₀₂) (wherein A₁₀₂may be a C₆-C₆₀aryl group), and the term “C₆-C₆₀arylthio group” as used herein may be a group represented by —S(A₁₀₃) (wherein A₁₀₃may be a C₆-C₆₀aryl group).

The term “C₇-C₆₀aryl alkyl group” as used herein may be a group represented by -(A₁₀₄)(A₁₀₅) (wherein A₁₀₄may be a C₁-C₅₄alkylene group, and A₁₀₅may be a C₆-C₅₉aryl group), and the term “C₂-C₆₀heteroaryl alkyl group” as used herein may be a group represented by -(A₁₀₆)(A₁₀₇) (wherein A₁₀₆may be a C₁-C₅₉alkylene group, and A₁₀₇may be a C₁-C₅₉heteroaryl group).

The group R_10aas used herein may be:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂).

The groups Q₁to Q₃, Q₁₁to Q₁₃, Q₂₁to Q₂₃, and Q₃₁to Q₃₃as used herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C₁-C₆₀alkyl group; a C₂-C₆₀alkenyl group; a C₂-C₆₀alkynyl group; a C₁-C₆₀alkoxy group; a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C₇-C₆₀aryl alkyl group; or a C₂-C₆₀heteroaryl alkyl group.

The term “heteroatom” as used herein may be any atom other than a carbon atom or a hydrogen atom. Examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

The term “third-row transition metal” as used herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), or the like.

The term “Ph” as used herein refers to a phenyl group, the term “Me” as used herein refers to a methyl group, the term “Et” as used herein refers to an ethyl group, the terms “tert-Bu” or “Bu^t” as used herein each refer to a tert-butyl group, and the term “OMe” as used herein refers to a methoxy group.

The term “biphenyl group” as used herein may be a “phenyl group substituted with a phenyl group.” For example, the “biphenyl group” may be a substituted phenyl group having a C₆-C₆₀aryl group as a substituent.

The term “terphenyl group” as used herein may be a “phenyl group substituted with a biphenyl group”. For example, the “terphenyl group” may be a substituted phenyl group having, as a substituent, a C₆-C₆₀aryl group substituted with a C₆-C₆₀aryl group.

The symbols * and *′ as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.

Hereinafter, compounds according to embodiments and light-emitting devices according to embodiments will be described in detail with reference to the Synthesis Examples and the Examples. The wording “B was used instead of A” used in describing Synthesis Examples means that an identical molar equivalent of B was used in place of A.

EXAMPLES
Synthesis Example
Synthesis Example 1: Synthesis of Compound 1

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(1) Synthesis of Intermediate Compound 1-a

[1,1′:3′,1″-terphenyl]-2′-amine (1.0 eq), 1-iodo-2-nitrobenzene (2.0 eq), Pd₂(dba)₃(5 mol %), Sphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110° C. for 12 hours. The reaction mixture was cooled at room temperature, and subjected to an extraction process three times by utilizing dichloromethane and water to obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of methylene chloride (MC):hexane=1:10) was used to synthesize Intermediate Compound 1-a (yield: 85%).

(2) Synthesis of Intermediate Compound 1-b

Intermediate Compound 1-a (1.0 eq), Sn (2.5 eq), and HCl (45 eq) were dissolved in ethanol and stirred at 80° C. for 12 hours, to thereby obtain a reactant. The reactant was cooled at room temperature and neutralized by utilizing a NaOH solution. The neutralized product was subjected to an extraction process by utilizing dichloromethane and water to obtain an organic layer, followed by filtration through celite/silica gel. The filtrate was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of MC:hexane=1:3) was used to synthesize Intermediate Compound 1-b (yield: 97%).

(3) Synthesis of Intermediate Compound 1-c

9-(4-(tert-butyl)pyridin-2-yl)-2-iodo-9H-carbazole (1.2 eq) was dissolved in anhydrous THF (0.025 M) under the nitrogen condition, and cooled at −30° C. Isopropylmagnesium chloride (2.0 M solution in THF, 1.2 eq) was slowly added to the reaction mixture, followed by addition of a solution in which 3-bromobenzaldehyde (1.0 eq) was dissolved in anhydrous THF (0.1 M). The reaction mixture was cooled at room temperature and stirred for 12 hours. An extraction process was performed three times by utilizing ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of ethyl acetate (EA):hexane 1:7) was used to synthesize Intermediate Compound 1-c (yield: 91%).

(4) Synthesis of Intermediate Compound 1-d

Pentafluorobenzoic acid (1.0 eq), Intermediate Compound 1-c (1.0 eq), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC·HCl) (1.1 eq), and 4-dimethylaminopyridine (DMAP) (0.25 eq) were dissolved in MC (0.1 M) and stirred at room temperature for 18 hours. The reaction mixture was subjected to an extraction process three times by utilizing dichloromethane and water to obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of EA:hexane=1:20) was used to synthesize Intermediate Compound 1-d (yield: 40%).

(5) Synthesis of Intermediate Compound 1-e

Intermediate Compound 1-d (1.0 eq), 2-furylboronic acid (1.5 eq), (η³-1-^tBu-indenyl)Pd(IPr)(Cl) (1 mol %), and K₂CO₃(2.0 eq) were dissolved in toluene and ethanol (0.1 M, a volume ratio of 4:1) and stirred at 40° C. for 4 hours. The reaction mixture was subjected an extraction process three times by utilizing ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of EA:hexane=1:20) was used to synthesize Intermediate Compound 1-e (yield: 95%).

(6) Synthesis of Intermediate Compound 1-f

Intermediate Compound 1-b (1.5 eq), Intermediate Compound 1-e (1.0 eq), Pd₂(dba)₃(10 mol %), Sphos (15 mol %), and Sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110° C. for 3 hours. The reaction mixture was cooled at room temperature, and the solvent was removed under reduced pressure. An extraction process was performed thereon three times by utilizing dichloromethane and water to obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of EA:hexane=1:10) was used to synthesize Intermediate Compound 1-f (yield: 89%).

(7) Synthesis of Intermediate Compound 1-g

Intermediate Compound 1-f (1.0 eq) was dissolved in triethyl orthoformate (30 eq), and 37% HCl (1.5 eq) was added thereto, followed by stirring for 12 hours at 80° C., to thereby obtain a reactant. The reactant was cooled at room temperature, and triethyl orthoformate in the reactant was concentrated, followed by an extraction process three times by utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of MC:methanol=95:5) was used to synthesize Intermediate Compound 1-g (yield: 85%).

(8) Synthesis of Intermediate Compound 1-h

Intermediate Compound 1-g (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), and distilled water was added thereto, followed by stirring for 3 hours at room temperature, to thereby obtain a reactant. The reactant was washed by utilizing distilled water and subjected to filtration to thereby obtain a solid, and the solid was subjected to an extraction process three times by utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, to thereby synthesize Intermediate Compound 1-h (yield: 90%).

(9) Synthesis of Compound 1

Intermediate Compound 1-h, dichloro(1,5-cyclooctadiene)platinum (II) (1.1 eq), and sodium acetate (2.0 eq) were dissolved in anhydrous 1,4-dioxane (0.05 M), and stirred for 4 days at 120° C. in the nitrogen condition, to thereby obtain a reactant. The reactant was cooled at room temperature and subjected to an extraction process three times by utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of MC:hexane=3:7) was used to synthesize Compound 1 (yield: 19%).

Synthesis Example 2: Synthesis of Compound 13

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(1) Synthesis of Intermediate Compound 13-a

Intermediate Compound 1-d (1.0 eq), (3-(tert-butyl)furan-2-yl)boronic acid (1.5 eq), (η³-1-^tBu-indenyl)Pd(IPr)(Cl) (1 mol %), and K₂CO₃(2.0 eq) were dissolved in toluene and ethanol (0.1 M, a volume ratio of 4:1) and stirred at 40° C. for 4 hours. The reaction mixture was subjected to an extraction process three times by utilizing ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of EA:hexane=1:20) was used to synthesize Intermediate Compound 13-a (yield: 92%).

(2) Synthesis of Intermediate Compound 13-b

Intermediate Compound 1-b (1.5 eq), 13-a (1.0 eq), Pd₂(dba)₃(10 mol %), Sphos (15 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110° C. for 3 hours. The reaction mixture was cooled at room temperature, and the solvent was removed under reduced pressure. An extraction process was performed thereon three times by utilizing dichloromethane and water to obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of EA:hexane=1:10) was used to synthesize Intermediate Compound 13-b (yield: 78%).

(3) Synthesis of Intermediate Compound 13-c

Intermediate Compound 13-b (1.0 eq) was dissolved in triethyl orthoformate (30 eq), and 37% HCl (1.5 eq) was added thereto, followed by stirring for 12 hours at 80° C., to thereby obtain a reactant. The reactant was cooled at room temperature, and triethyl orthoformate in the reactant was concentrated, followed by an extraction process three times by utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of MC:methanol=95:5) was used to synthesize Intermediate Compound 13-c (yield: 93%).

(4) Synthesis of Intermediate Compound 13-d

Intermediate Compound 13-c (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), and distilled water was added thereto, followed by stirring for 3 hours at room temperature, to thereby obtain a reactant. The reactant was washed by utilizing distilled water and subjected to filtration to thereby obtain a solid, and the solid was subjected to an extraction process three times by utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, to thereby synthesize Intermediate Compound 13-d (yield: 92%).

(5) Synthesis of Compound 13

Intermediate Compound 13-d, dichloro(1,5-cyclooctadiene)platinum (II) (1.1 eq), and sodium acetate (2.0 eq) were dissolved in anhydrous 1,4-dioxane (0.05 M), and stirred for 4 days at 120° C. in the nitrogen condition, to thereby obtain a reactant. The reactant was cooled at room temperature and subjected to an extraction process three times by utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of MC:hexane=3:7) was used to synthesize Compound 13 (yield: 21%).

Synthesis Example 3: Synthesis of Compound 85

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(1) Synthesis of Intermediate Compound 85-a

2-bromo-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.1 eq), 3-Bromoaniline (1.0 eq), Pd₂(dba)₃(0.05 eq), SPhos (0.075 eq), and NaOtBu (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110° C. for 12 hours. The reaction mixture was cooled at room temperature and subjected to an extraction process three times by utilizing dichloromethane and water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of MC:hexane=1:10) was used to synthesize Intermediate Compound 85-a (yield: 53%).

(2) Synthesis of Intermediate Compound 85-b

Intermediate Compound 85-a (1.1 eq), 2-bromofuran (1.0 eq), PtBu₃(5 mol %), Pd₂(dba)₃(0.05 eq), and NaOtBu (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 100° C. for 16 hours. The reaction mixture was cooled at room temperature, and toluene was removed under reduced pressure. An extraction process was performed thereon three times by utilizing dichloromethane and water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of MC:hexane=1:10) was used to synthesize Intermediate Compound 85-b (yield: 75%).

(3) Synthesis of Intermediate Compound 85-c

Intermediate Compound 1-b (1.5 eq), Intermediate Compound 85-b (1.0 eq), Pd₂(dba)₃(5 mol %), Sphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110° C. for 3 hours. The reaction mixture was cooled at room temperature, and the solvent was removed under reduced pressure. An extraction process was performed thereon three times by utilizing dichloromethane and water to obtain an organic layer. The organic layer thus obtained was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of EA:hexane=1:10) was used to synthesize Intermediate Compound 85-c (yield: 85%).

(4) Synthesis of Intermediate Compound 85-d

Intermediate Compound 85-c (1.0 eq) was dissolved in triethyl orthoformate (30 eq), and 37% HCl (1.5 eq) was added thereto, followed by stirring for 12 hours at 80° C., to thereby obtain a reactant. The reactant was cooled at room temperature, and triethyl orthoformate in the reactant was concentrated, followed by an extraction process three times by utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of MC:methanol=95:5) was used to synthesize Intermediate Compound 85-d (yield: 91%).

(5) Synthesis of Intermediate Compound 85-e

Intermediate Compound 85-d (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), and distilled water was added thereto, followed by stirring for 3 hours at room temperature, to thereby obtain a reactant. The reactant was washed by utilizing distilled water and subjected to filtration to thereby obtain a solid, and the solid was subjected to an extraction process three times by utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate, and concentrated to synthesize Intermediate compound 85-e (yield: 96%).

(6) Synthesis of Compound 85

Intermediate Compound 85-e, dichloro(1,5-cyclooctadiene)platinum (II) (1.1 eq), and sodium acetate (2.0 eq) were dissolved in anhydrous 1,4-dioxane (0.05 M), and stirred for 4 days at 120° C. in the nitrogen condition, to thereby obtain a reactant. The reactant was cooled at room temperature and subjected to an extraction process three times by utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of MC:hexane=3:7) was used to synthesize Compound 85 (yield: 21%).

Synthesis Example 4: Synthesis of Compound 90

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(1) Synthesis of Intermediate Compound 90-a

Benzimidazole (1.5 eq), Intermediate Compound 85-b (1.0 eq), CuI (20 mol %), 2-picolinic acid (0.2 eq), and K₃PO₄(2.0 eq) were dissolved in DMF (0.15 M) and stirred at 160° C. for 12 hours. The reaction mixture was cooled at room temperature, and the solvent was removed under reduced pressure. An extraction process was performed thereon three times by utilizing ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of EA:hexane=1:4) was used to synthesize Intermediate Compound 90-a (yield: 56%).

(2) Synthesis of Intermediate Compound 90-b

Intermediate Compound 90-a (1.0 eq), (3,5-di-tert-butylphenyl)(mesityl)iodonium trifluoromethanesulfonate (1.3 eq), and Cu(OAc)₂(20 mol %) were dissolved in DMF (0.25 M) and stirred at 100° C. for 4 hours, to thereby obtain a reactant. The reactant was cooled at room temperature, DMF in the reactant was concentrated, followed by an extraction process three times by utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of MC:methanol=95:5) was used to synthesize Intermediate Compound 90-b (yield: 90%).

(3) Synthesis of Compound 90

Intermediate Compound 90-b, dichloro (1,5-cyclooctadiene)platinum (II) (1.1 eq), and sodium acetate (2.0 eq) were dissolved in DMF (0.05 M) and stirred at 140° C. for 12 hours under the nitrogen condition, to thereby obtain a reactant. The reactant was cooled at room temperature and subjected to filtration through celite/silica and concentration, followed by an extraction process three times by utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of MC:hexane=3:7) was used to synthesize Compound 90 (yield: 25%).

Comparative Synthesis Example 1: Synthesis of Comparative Compound 1

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(1) Synthesis of Intermediate Compound D-1

2-methoxy-9H-carbazole (1.0 eq), 2-bromo-4-(tert-butyl)pyridine (1.1 eq), Pd₂(dba)₃(5 mol %), Sphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 110° C. for 12 hours. The reaction mixture was cooled at room temperature, and the solvent was removed under reduced pressure. An extraction process was performed thereon three times by utilizing dichloromethane and water to obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of EA:hexane=1:10) was used to synthesize Intermediate Compound D-1 (yield: 72%).

(2) Synthesis of Intermediate Compound D-2

Intermediate Compound D-1 (1.0 eq), HBr (0.5 M), and acetic acid (0.5 M) were stirred at 120° C. for 16 hours. The reaction mixture was cooled at room temperature and neutralized to pH 7 by utilizing a NaOH aqueous solution, followed by an extraction process three times by utilizing ethyl acetate and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and subjected to filtration through silica gel, to thereby synthesize Intermediate Compound D-2 (yield: 85%).

(3) Synthesis of Intermediate Compound D-3

1,3-dibromo-5-tert-butylbenzene (1.2 eq), Intermediate Compound D-2 (1.0 eq), CuI (10 mol %), BPPO ligand (10 mol %), and potassium phosphate tribasic (2.0 eq) were dissolved in DMF (0.1 M) and stirred at 160° C. for 10 hours. The reaction mixture was cooled at room temperature, and DMF was removed under reduced pressure. An extraction process was performed thereon three times by utilizing dichloromethane and water to obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of EA:hexane=1:10) was used to synthesize Intermediate Compound D-3 (yield: 60%).

(4) Synthesis of Intermediate Compound D-4

Benzimidazole (1.5 eq), Intermediate Compound D-3 (1.0 eq), CuI (30 mol %), L-proline (0.3 eq), and K₃PO₄(2.0 eq) were dissolved in DMF (0.15 M) and stirred at 160° C. for 12 hours. The reaction mixture was cooled at room temperature, and the solvent was removed under reduced pressure. An extraction process was performed thereon three times by utilizing ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of EA:hexane=1:4) was used to synthesize Intermediate Compound D-4 (yield: 55%).

(5) Synthesis of Intermediate Compound D-5

Intermediate Compound D-4 (1.0 eq) and Iodomethane (2.0 eq) were dissolved in toluene (0.1 M) and stirred at 120° C. for 12 hours, to thereby obtain a reactant. The reactant was cooled at room temperature and subjected to filtration, to synthesize Intermediate Compound D-5 (yield: 85%).

(6) Synthesis of Intermediate Compound D-6

Intermediate Compound D-5 (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), and distilled water was added thereto, followed by stirring for 3 hours at room temperature, to thereby obtain a reactant. The reactant was washed by utilizing distilled water and subjected to filtration to thereby obtain a solid, and the solid was subjected to an extraction process three times by utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate, and concentrated to synthesize Intermediate Compound D-6 (yield of 93%).

(7) Synthesis of Comparative Compound 1

Intermediate Compound D-6, dichloro(1,5-cyclooctadiene)platinum (II) (1.1 eq), and sodium acetate (2.0 eq) were dissolved in anhydrous 1,4-dioxane (0.05 M), and stirred for 4 days at 120° C. in the nitrogen condition, to thereby obtain a reactant. The reactant was cooled at room temperature and subjected to an extraction process three times by utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (a volume ratio of MC:hexane=3:7) was used to synthesize Comparative Compound 1 (yield: 18%).

¹H NMR and HR-MS of the compounds synthesized according to Synthesis Examples above are shown in Table 1. Synthesis methods for other compounds than the compounds shown in Table 1 may be readily recognized by those skilled in the technical field by referring to the synthesis paths and source material materials described above.

TABLE 1

HR-MS

Com-

Found

pound

¹H-NMR (CDCl₃, 500 MHz)
calc.
[M + 1]

Com-
8.74 (1H, dd), 8.42 (1H, dd), 8.20 (2H,
994.07
994.11

pound
dd), 8.19 (1H, s), 7.58 (1H, s), 7.49-

1
7.50 (2H, m), 7.43-7.41 (7H, m), 7.40

(1H, s), 7.39 (1H, dd), 7.31 (1H, s),

7.20 (1H, s), 7.19 (1H, dd), 7.14 (2H,

dd), 7.08 (5H, m), 6.95 (2H, dd), 6.84

(1H, s), 6.33 (1H, s), 6.11 (1H, dd),

5.57 (1H, s), 1.32 (9H, s)

Com-
8.75 (1H, dd), 8.41 (1H, dd), 8.20 (2H,
1050.18
1050.17

pound
dd), 8.19 (1H, s), 7.58 (1 H, s),

13
7.50 (1H, s), 7.43-7.41 (7H, m), 7.40

(1H, s), 7.39 (1H, dd), 7.31 (1H, s),

7.20 (1H, s), 7.19 (1H, dd), 7.14 (2H,

dd), 7.08 (5H, m), 6.95 (2H, dd),

6.84 (1H, s), 6.33 (1H, s), 6.11 (1H,

dd), 5.57 (1H, s), 1.35 (9H, s), 1.32

(9H, s)

Com-
8.74 (1H, dd), 8.42 (1H, dd), 8.20 (2H,
995.06
995.01

pound
dd), 8.19 (1H, s), 7.58 (1H, s), 7.49

85
(1H, dd), 7.50 (1H, s), 7.43 (4H, m),

7.41-7.40 (5H, m), 7.39 (1H, dd),

7.31 (1H, s), 7.20 (1H, s), 7.19 (1H,

dd), 7.14 (2H, dd), 7.08 (5H, m),

6.95 (2H, dd), 6.84 (1H, s), 6.33

(1H, s), 6.11 (1H, dd), 1.32 (9H, s)

Com-
8.74 (1H, dd), 8.39 (1H, dd), 8.19 (1H,
955.08
955.01

pound
dd), 7.88 (1H, s), 7.58 (1H, s), 7.50

90
(1H, s), 7.40 (2H, m), 7.20 (4H, m),

7.14 (3H, m), 7.11 (1H, s), 7.00

(1H, s), 6.84 (2H, d) 6.68 (1H, s), 6.40

(1H, s), 1.41 (18H, s), 1.32 (9H, s)

Com-
8.70 (1H, s), 8.39 (1H, dd), 8.19 (1H,
771.83
771.77

parative
dd), 7.58 (1H, s), 7.50 (1H, s), 7.43

Com-
(2H, m), 7.41 (1H, s), 7.40 (1H,

pound
dd), 7.20 (1H, s), 7.12 (1H, dd), 7.08

1
(1H, s), 6.71 (2H, m), 6.69 (1H, s),

3.36 (3H, s), 1.32 (18H, s)

Evaluation Example 1

A simulation maximum emission wavelength (λ_max^sim), an actual maximum emission wavelength (λ_max^exp), a ratio of presence of a ³MLCT state, and an energy level of a ³MC state of each of Compounds 1, 13, 85, and 90, Compounds A to C, and Comparative Compound 1 were evaluated by utilizing the DFT method of the Gaussian program, which is structure-optimized at the B3LYP/6-31 G(d,p) level, and results thereof are shown in Table 2.

TABLE 2

λ_max^sim
λ_max^exp

³MC

³MLCT

Compound
(nm)
(nm)
(kcal/mol)
(%)

A
520
515
0.41
8.8

B
550
550
0.41
9.5

C
620
620
0.21
8.4

Comparative
468
471
0.21
8.8

Compound 1

Compound 1
451
453
0.82
13.11

Compound 13
451
453
0.85
13.08

Compound 85
453
457
0.82
12.68

Compound 90
453
453
0.81
13.10

According to Table 2, as compared to Compounds A to C and Comparative Compound 1, Compounds 1, 13, 85, and 90 each emitted blue light having high color purity, and each had a high ratio of presence of the ³MLCT state and a high energy of the ³MC state.

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Example 1

As an anode, a glass substrate with a 15 Ω/cm²(1,200 Å) ITO formed thereon (available from Corning Co., Ltd) was cut to a size of 50 mm×50 mm×0.7 mm, sonicated by utilizing isopropyl alcohol and pure water for 5 minutes in each solvent, washed by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes, and was mounted on a vacuum deposition apparatus.

2-TNATA was vacuum-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 (hereinafter, referred as “NPB”) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.

Compound 1 (organometallic compound), Compound ETH85 (second compound), and Compound HTH29 (third compound) were vacuum-deposited on the hole transport layer to form an emission layer having a thickness of 400 Å. Here, an amount of Compound 1 was 10 wt % based on a total weight (100 wt %) of the emission layer, and a weight ratio of Compound ETH85 to Compound HTH29 was adjusted to 3:7.

Compound ETH2 was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å, Alq₃was vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, LiF was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited thereon to form a cathode having a thickness of 3,000 Å, thereby completing the manufacture of an organic light-emitting device.

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Examples 2 to 6 and Comparative Examples 1 and 2

Organic light-emitting devices were manufactured in the same manner as used in Example 1, except that, in forming the emission layer, compounds shown in Table 4 were used.

Evaluation Example 2

For the organic light-emitting devices manufactured in Examples 1 to 6 and Comparative Examples 1 and 2, driving voltage (V) at 1,000 cd/n²and luminescence efficiency (cd/A) were each measured by utilizing a Keithley MU 236 and a luminance meter PR650, and results thereof are shown in Table 3.

TABLE 3

Weight ratio

of second

compound

Driving
Luminescence

Organometallic
Second
Third
Fourth
to third
Luminance
voltage
efficiency

No.
compound
compound
compound
compound
compound
(cd/m²)
(V)
(cd/A)

Example 1
Compound 1
ETH85
HTH29
—
3:7
1,000
4.8
47

(10 wt %)

Example 2
Compound 13
ETH85
HTH29
—
3:7
1,000
4.8
45

(10 wt %)

Example 3
Compound 85
ETH85
HTH41
—
3:7
1,000
4.9
39

(10 wt %)

Example 4
Compound 90
ETH85
HTH29
—
3:7
1,000
4.8
46

(10 wt %)

Example 5
Compound 1
ETH85
HTH29
DFD1
3:7
1,000
4.9
60

(10 wt %)

(0.5 wt %)

Example 6
Compound 90
ETH85
HTH29
DFD1
3:7
1,000
4.9
60

(10 wt %)

(0.5 wt %)

Comparative
Comparative
ETH85
HTH29
—
3:7
1,000
5.0
22

Example 1
Compound 1

(10 wt %)

Comparative
Comparative
ETH85
HTH29
DFD1
3:7
1,000
5.0
29

Example 2
Compound 1

(0.5 wt %)

(10 wt %)

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From Tables 2 and 3, it was confirmed that the organic light-emitting devices of Examples 1 to 6 emitted deep blue light and had excellent driving voltage and excellent luminescence efficiency characteristics, as compared to the organic light-emitting devices of Comparative Examples 1 and 2.

According to embodiments, an organometallic compound may have excellent electrical characteristics, and a light-emitting device including the organometallic compound may have low driving voltage and high luminescence efficiency.

Embodiments have been disclosed herein, and although terms are employed, they are used and are to be interpreted in a generic and descriptive sense only and not for purpose of limitation. In some instances, as would be apparent by one of ordinary skill in the art, features, characteristics, and/or elements described in connection with an embodiment may be used singly or in combination with features, characteristics, and/or elements described in connection with other embodiments unless otherwise specifically indicated. Accordingly, it will be understood by those of ordinary skill in the art that various changes in form and details may be made without departing from the spirit and scope of the disclosure as set forth in the claims.

LIGHT-EMITTING DEVICE, ELECTRONIC APPARATUS INCLUDING THE SAME, AND ORGANOMETALLIC COMPOUND

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