Organic light-emitting device

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority to and the benefits of Korean Patent Application No. 10-2015-0063220, filed on May 6, 2015, in the Korean Intellectual Property Office, and Korean Patent Application No. 10-2016-0029102, filed on Mar. 10, 2016, in the Korean Intellectual Property Office, the disclosures of both of which are incorporated herein in their entireties by reference.

BACKGROUND
1. Field

One or more embodiments of the present disclosure relate to an organic light-emitting device.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices that have wide viewing angles, high contrast ratios, short response times, and/or excellent luminance, driving voltage, and/or response speed characteristics, and may produce full color images.

For example, an organic light-emitting device of the present inventive concept may include a first electrode disposed on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode, which are sequentially disposed 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. When the excitons drop from an excited state to a ground state, light is emitted.

SUMMARY

An aspect according to one or more embodiments of the present disclosure is directed toward an organic light-emitting device.

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

According to one or more embodiments, an organic light-emitting device includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer,

wherein the organic layer may include a first compound represented by Formula 1 and a second compound represented by one selected from Formulae 2-1 to 2-4:

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wherein, in Formulae 1, A, and 2-1 to 2-4,

R₁to R₁₄may each independently be selected from a group represented by Formula A, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂).

at least one selected from R₁to R₅, R₇to R₁₂, and R₁₄may be the group represented by Formula A,

Ar₂₁₁and Ar₂₁₂may each independently be selected from a naphthalene group, an anthracene group, a triphenylene group, a pyrene group, a chrysene group, and a perylene group,

Ar₂₄₁may be selected from a benzene group, a biphenyl group, and a triphenylene group,

L₁₀₁, L₂₁₁to L₂₁₃, L₂₂₁, L₂₃₁to L₂₃₄, and L₂₄₁may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

a101 may be selected from 0, 1, 2, and 3,

a211 to a213, a221, a231 to a234, and a241 may each independently be selected from 0, 1, and 2,

R₁₀₁, R₁₀₂, R₂₃₁to R₂₃₄, and R₂₄₁may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

b231 to b234 and b241 may each independently be selected from 1, 2, and 3,

R₂₁₁, R₂₁₂, R₂₂₁, R₂₂₂, R₂₃₅to R₂₃₈, and R₂₄₂may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

b211, b212, b221, b222, b235 to b238, and b242 may each independently be selected from 1, 2, and 3,

n211, n212, and n221 may each independently be selected from 1, 2, and 3,

n231 to n234 may each independently be selected from 0, 1, and 2, wherein the sum of n231 to n234 may be selected from 1, 2, 3, 4, 5, and 6,

n241 may be selected from 3, 4, 5, 6, 7, and 8, and

Q₁to Q₃may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings in which:

FIG. 1 is a diagram schematically illustrating a cross-section of a structure of an organic light-emitting device according to an embodiment;

FIG. 2 is a diagram schematically illustrating a cross-section of a structure of an organic light-emitting device according to another embodiment;

FIG. 3 is a diagram schematically illustrating a cross-section of a structure of an organic light-emitting device according to another embodiment; and

FIG. 4 is a diagram schematically illustrating a cross-section of a structure of an organic light-emitting device according to another embodiment.

DETAILED DESCRIPTION

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

As the inventive concept allows for various changes and numerous embodiments, particular embodiments will be illustrated in the drawings and described in more detail in the written description. Effects, features, and a method of achieving the inventive concept will be obvious by referring to exemplary embodiments of the inventive concept with reference to the attached drawings. The inventive concept may, however, be embodied in many different forms and should not be construed as being limited to the embodiments set forth herein.

Hereinafter, the inventive concept will be described in more detail by explaining exemplary embodiments of the inventive concept with reference to the attached drawings. Like reference numerals in the drawings denote like elements, and thus their description will not be repeated.

In the embodiments described in the present specification, an expression used in the singular encompasses the expression of the plural, unless it has a clearly different meaning in the context.

In the present specification, it is to be understood that the terms such as “including,” “having,” and “comprising” are intended to indicate the existence of the features or components disclosed in the specification, and are not intended to preclude the possibility that one or more other features or components may exist or may be added.

It will be understood that when a layer, region, or component is referred to as being “on” or “onto” another layer, region, or component, it may be directly or indirectly formed on the other layer, region, or component. That is, for example, intervening layer(s), region(s), or component(s) may be present.

Sizes of components in the drawings may be exaggerated for convenience of explanation. In other words, since sizes and thicknesses of components in the drawings are arbitrarily illustrated for convenience of explanation, the following embodiments are not limited thereto.

As used herein, the expression “(an organic layer) includes at least one first compound” may be construed to refer to “(an organic layer) may include one first compound represented by Formula 1, or two or more different first compounds each represented by Formula 1”.

In an embodiment, a first electrode may be an anode, which is a hole injection electrode, and a second electrode may be a cathode, which is an electron injection electrode; or a first electrode may be a cathode, which is an electron injection electrode, and a second electrode may be an anode, which is a hole injection electrode.

For example, the first electrode may be an anode, the second electrode may be a cathode, and an organic layer between the first electrode and the second electrode may include i) a hole transport region disposed between the first electrode and an emission layer and including at least one selected from a hole injection layer, a hole transport layer, and an electron blocking layer; and/or ii) an electrode transport region disposed between an emission layer and the second electrode and including at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

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

Descriptions of FIG. 1

FIG. 1 is a diagram schematically illustrating a cross-section of a structure of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

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

First Electrode 110

In FIG. 1, a substrate may be additionally disposed under the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and/or water-resistance.

The first electrode 110 may be formed by depositing or sputtering a material for the first electrode 110 on the substrate. When the first electrode 110 is an anode, the material for the first electrode 110 may be selected from materials with a high work function to facilitate hole injection.

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, the material for the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and combinations thereof, but embodiments of the present disclosure are not limited thereto. In various embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material for the first electrode 110 may be selected from magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and combinations thereof, but embodiments of the present disclosure are not limited thereto.

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

Organic Layer 150

The organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emission layer.

The organic layer 150 may include a first compound represented by Formula 1 and a second compound represented by one selected from Formulae 2-1 to 2-4. The first compound represented by Formula 1 may include at least one group represented by Formula A:

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In Formula 1, R₁to R₁₄may each independently be selected from the group represented by Formula A, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

at least one selected from R₁to R₅, R₇to R₁₂, and R₁₄may be the group represented by Formula A, and

For example, R₁to R₁₄in Formula 1 may each independently be selected from the group consisting of:

the group represented by Formula A, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, and a cyclohexyl group;

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

wherein Q₁to Q₃may each independently be selected from a C₁-C₂₀alkyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but embodiments of the present disclosure are not limited thereto.

In various embodiments, R₁to R₁₄in Formula 1 may each independently be selected from the group consisting of:

the group represented by Formula A, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, and a cyclohexyl group;

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

Q₁to Q₃may each independently be selected from a C₁-C₂₀alkyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but embodiments of the present disclosure are not limited thereto.

In various embodiments, R₁to R₁₄in Formula 1 may each independently be selected from the group represented by Formula A, hydrogen, deuterium, —F, a hydroxyl group, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenyl group substituted with a methyl group, a fluorenyl group substituted with a methyl group, and —Si(CH₃)₃, but embodiments of the present disclosure are not limited thereto.

In various embodiments, in Formula 1, R₁, R₂, R₃, R₄, R₅, R₇, R₈, R₉, R₁₀, R₁₁, R₁₂, and/or R₁₄may be the group represented by Formula A, but embodiments of the present disclosure are not limited thereto.

In various embodiments, in Formula 1, R₁and R₇may each independently be the group represented by Formula A,

R₁and R₈may each independently be the group represented by Formula A,

R₁and R₉may each independently be the group represented by Formula A,

R₁and R₁₀may each independently be the group represented by Formula A,

R₂and R₇may each independently be the group represented by Formula A,

R₂and R₈may each independently be the group represented by Formula A,

R₂and R₉may each independently be the group represented by Formula A,

R₂and R₁₀may each independently be the group represented by Formula A,

R₃and R₇may each independently be the group represented by Formula A,

R₃and R₈may each independently be the group represented by Formula A,

R₃and R₉may each independently be the group represented by Formula A,

R₃and R₁₀may each independently be the group represented by Formula A,

R₄and R₇may each independently be the group represented by Formula A,

R₄and R₈may each independently be the group represented by Formula A,

R₄and R₉may each independently be the group represented by Formula A, or

R₄and R₁₀may each independently be the group represented by Formula A, but embodiments of the present disclosure are not limited thereto.

In various embodiments, R₂and R₈in Formula 1 may each independently be the group represented by Formula A, but embodiments of the present disclosure are not limited thereto.

In Formula A, L₁₀₁may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

For example, L₁₀₁in Formula A may be selected from the group consisting of:

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, a benzofuranylene group, a benzothiophenylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl 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 phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl 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, a thiadiazolyl group, and an imidazopyridinyl group, but embodiments of the present disclosure are not limited thereto.

In various embodiments, L₁₀₁in Formula A may be selected from the group consisting of:

a phenylene group, a naphthylene group, a fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, an indolylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, a benzimidazolylene group, a benzofuranylene group, a benzothiophenylene group, a triazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, but embodiments of the present disclosure are not limited thereto.

In various embodiments, L₁₀₁in Formula A may be represented by one selected from Formulae 3-1 to 3-31, but embodiments of the present disclosure are not limited thereto:

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In Formulae 3-1 to 3-31,

Y₃₁may be selected from C(R₃₃)(R₃₄), N(R₃₃), O, and S,

R₃₁to R₃₄may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group,

a31 may be selected from 1, 2, 3, and 4,

a32 may be selected from 1, 2, 3, 4, 5, and 6,

a33 may be selected from 1, 2, 3, 4, 5, 6, 7, and 8,

a34 may be selected from 1, 2, 3, 4, and 5,

a35 may be selected from 1, 2, and 3, and

* and *′ each independently indicate a binding site to a neighboring atom.

For example, in Formulae 3-1 to 3-31,

Y₃₁may be selected from C(R₃₃)(R₃₄), N(R₃₃), O, and S, and

R₃₁to R₃₄may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, a tert-butyl group, a methoxy group, an ethoxy group, a tert-butoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, but embodiments of the present disclosure are not limited thereto.

In various embodiments, L₁₀₁in Formula A may be represented by one selected from Formulae 4-1 to 4-56, but embodiments of the present disclosure are not limited thereto:

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In Formulae 4-1 to 4-56, * and *′ each independently indicate a binding site to a neighboring atom.

In various embodiments, L₁₀₁in Formula A may be represented by one selected from Formulae 4-1 to 4-12 and 4-39 to 4-56, but embodiments of the present disclosure are not limited thereto.

In Formula A, a101 indicates the number of L₁₀₁(s), and may be selected from 0, 1, 2, and 3. When a101 is 0, (L₁₀₁)_a101may be a single bond. When a101 is two or more, a plurality of L₁₀₁(s) may be identical to or different from each other. For example, a101 in Formula A may be selected from 0 and 1, but embodiments of the present disclosure are not limited thereto. In various embodiments, a101 in Formula A may be 0, but embodiments of the present disclosure are not limited thereto.

In Formula A, R₁₀₁and R₁₀₂may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, R₁₀₁and R₁₀₂in Formula A may each independently be selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl 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 carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl 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 carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and —B(Q₃₁)(Q₃₂); and

Q₃₁to Q₃₃may each independently be selected from a C₁-C₂₀alkyl group, a C₆-C₆₀aryl group, a biphenyl group, and a terphenyl group, but embodiments of the present disclosure are not limited thereto.

In various embodiments, R₁₀₁and R₁₀₂in Formula A may each independently be selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃); and

In various embodiments, R₁₀₁and R₁₀₂in Formula A may each independently be selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, —CD₃, —CF₃, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), and

Q₃₁to Q₃₃may each independently be selected from a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but embodiments of the present disclosure are not limited thereto.

In various embodiments, R₁₀₁and R₁₀₂in Formula A may each independently be selected from groups represented by Formulae 5-1 to 5-32, but embodiments of the present disclosure are not limited thereto:

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In Formulae 5-1 to 5-32,

Y₅₁may be selected from C(R₅₃)(R₅₄), Si(R₅₃)(R₅₄), N(R₅₃), O, and S,

R₅₁to R₅₄may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, —CD₃, —CF₃, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃),

Q₃₁to Q₃₃may each independently be selected from a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group,

a51 may be selected from 1, 2, 3, 4, and 5,

a52 may be selected from 1, 2, 3, 4, 5, 6, and 7,

a53 may be selected from 1, 2, 3, 4, 5, and 6,

a54 may be selected from 1, 2, and 3,

a55 may be selected from 1, 2, 3, and 4, and

* indicates a binding site to a neighboring atom.

In various embodiments, R₁₀₁and R₁₀₂in Formula A may each independently be selected from groups represented by Formulae 6-1 to 6-195, but embodiments of the present disclosure are not limited thereto:

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In Formulae 6-1 to 6-195,

t-Bu is a tert-butyl group,

Ph is a phenyl group, and

* indicates a binding site to a neighboring atom.

For example, the first compound represented by Formula 1 may be represented by Formula 1-1, but embodiments of the present disclosure are not limited thereto:

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In Formula 1-1,

R₂and R₈may each independently be the group represented by Formula A.

In various embodiments, the first compound represented by Formula 1 may be selected from Compounds 1 to 112, but embodiments of the present disclosure are not limited thereto:

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In Formula 2-1, Ar₂₁₁and Ar₂₁₂may each independently be selected from a naphthalene group, an anthracene group, a triphenylene group, a pyrene group, a chrysene group, and a perylene group.

For example, Ar₂₁₁in Formula 2-1 may be selected from an anthracene group, a triphenylene group, a pyrene group, a chrysene group, and a perylene group, and

Ar₂₁₂may be selected from a naphthalene group, an anthracene group, a triphenylene group, a pyrene group, a chrysene group, and a perylene group, but embodiments of the present disclosure are not limited thereto.

In various embodiments, Ar₂₁₁and Ar₂₁₂in Formula 2-1 may each independently be selected from an anthracene group, a triphenylene group, a pyrene group, a chrysene group, and a perylene group, but embodiments of the present disclosure are not limited thereto.

In various embodiments, Ar₂₁₁and Ar₂₁₂in Formula 2-1 may be identical to each other, but embodiments of the present disclosure are not limited thereto.

In various embodiments, Ar₂₁₁and Ar₂₁₂in Formula 2-1 may each independently be an anthracene group, but embodiments of the present disclosure are not limited thereto.

In Formula 2-4, Ar₂₄₁may be selected from a benzene group, a biphenyl group, and a triphenylene group.

In Formulae 2-1 to 2-4, L₂₁₁to L₂₁₃, L₂₂₁, L₂₃₁to L₂₃₄, and L₂₄₁may each independently be the same as described herein in connection with L₁₀₁.

In Formulae 2-1 to 2-4, a211 to a213, a221, a231 to a234, and a241 may each independently be selected from 0, 1, and 2. For example, in Formulae 2-1 to 2-4, a211 to a213, a221, a231 to a234, and a241 may each independently be selected from 0 and 1, but embodiments of the present disclosure are not limited thereto.

In Formulae 2-3 and 2-4, R₂₃₁to R₂₃₄and R₂₄₁may each independently be the same as described herein in connection with R₁₀₁.

For example, R₂₃₁to R₂₃₄and R₂₄₁in Formulae 2-3 and 2-4 may each independently be selected from the group consisting of:

In various embodiments, R₂₃₁to R₂₃₄and R₂₄₁in Formulae 2-3 and 2-4 may each independently be selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, and a naphthyl group, but embodiments of the present disclosure are not limited thereto.

In various embodiments, R₂₃₁to R₂₃₄and R₂₄₁in Formulae 2-3 and 2-4 may each independently be selected from groups represented by Formulae 7-1 to 7-16, but embodiments of the present disclosure are not limited thereto:

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In Formulae 7-1 to 7-16,

Y₇₁may be selected from C(R₇₃)(R₇₄), N(R₇₃), O, and S,

R₇₁to R₇₄may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, and a naphthyl group,

a71 may be selected from 1, 2, 3, 4, and 5,

a72 may be selected from 1, 2, 3, 4, 5, 6, and 7,

a73 may be selected from 1, 2, 3, 4, 5, and 6,

a74 may be selected from 1, 2, and 3,

a75 may be selected from 1, 2, 3, and 4, and

* indicates a binding site to a neighboring atom.

In various embodiments, R₂₃₁to R₂₃₄and R₂₄₁in Formulae 2-3 and 2-4 may each independently be selected from groups represented by Formulae 8-1 to 8-29, but embodiments of the present disclosure are not limited thereto:

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In Formulae 8-1 to 8-29,

t-Bu is a tert-butyl group,

Ph is a phenyl group, and

* indicates a binding site to a neighboring atom.

In Formulae 2-3 and 2-4, b231 to b234 and b241 may each independently be selected from 1, 2, and 3. For example, in Formulae 2-3 and 2-4, b231 to b234 and b241 may each independently be selected from 1 and 2, but embodiments of the present disclosure are not limited thereto.

In Formulae 2-1 to 2-4, R₂₁₁, R₂₁₂, R₂₂₁, R₂₂₂, R₂₃₅to R₂₃₈, and R₂₄₂may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), and

For example, in Formulae 2-1 to 2-4, R₂₁₁, R₂₁₂, R₂₂₁, R₂₂₂, R₂₃₅to R₂₃₈, and R₂₄₂may each independently be selected from the group consisting of:

hydrogen, deuterium, —F, —Cl, —Br, —I, a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, and a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, and a C₁-C₂₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₃₁)(Q₃₂), —Si(Q₃₁)(Q₃₂)(Q₃₃), and —B(Q₃₁)(Q₃₂);

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₃₁)(Q₃₂), —Si(Q₃₁)(Q₃₂)(Q₃₃), and —B(Q₃₁)(Q₃₂); and

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), and —B(Q₁)(Q₂), and

Q₁to Q₃and Q₃₁to Q₃₃may each independently be selected from a C₁-C₂₀alkyl group, a C₆-C₆₀aryl group, a biphenyl group, and a terphenyl group, but embodiments of the present disclosure are not limited thereto.

In various embodiments, in Formulae 2-1 to 2-4, R₂₁₁, R₂₁₂, R₂₂₁, R₂₂₂, R₂₃₅to R₂₃₈, and R₂₄₂may each independently be selected from the group consisting of:

hydrogen, deuterium, —F, —Cl, —Br, —I, a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, and a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, and a C₁-C₂₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a phenoxy group, a phenylthio group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —N(Q₃₁)(Q₃₂), —Si(Q₃₁)(Q₃₂)(Q₃₃), and —B(Q₃₁)(Q₃₂);

a phenoxy group, a phenylthio group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl 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 carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenoxy group, a phenylthio group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl 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 carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —N(Q₃₁)(Q₃₂), —Si(Q₃₁)(Q₃₂)(Q₃₃), and —B(Q₃₁)(Q₃₂); and

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), and —B(Q₁)(Q₂), and

Q₁to Q₃and Q₃₁to Q₃₃may each independently be selected from a C₁-C₂₀alkyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but embodiments of the present disclosure are not limited thereto.

In various embodiments, in Formulae 2-1 to 2-4, R₂₁₁, R₂₁₂, R₂₂₁, R₂₂₂, R₂₃₅to R₂₃₈, and R₂₄₂may each independently be selected from the group consisting of:

hydrogen, deuterium, —F, —Cl, —Br, —I, a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, and a C₁-C₂₀alkoxy group;

a phenoxy group, a phenylthio group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenoxy group, a phenylthio group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —N(Q₃₁)(Q₃₂), —Si(Q₃₁)(Q₃₂)(Q₃₃), and —B(Q₃₁)(Q₃₂); and

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), and —B(Q₁)(Q₂), and

In various embodiments, in Formulae 2-1 to 2-4, R₂₁₁, R₂₁₂, R₂₂₁, R₂₂₂, R₂₃₅to R₂₃₈, and R₂₄₂may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, an iso-propoxy group, an n-butoxy group, an iso-butoxy group, a sec-butoxy group, a tert-butoxy group, —Si(CH₃)₃, —Si(Ph)₃, —N(Ph₂)₂, —B(Ph)₂, and a group represented by any of Formulae 9-1 to 9-15, but embodiments of the present disclosure are not limited thereto:

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In Formulae 9-1 to 9-15,

Y₉₁may be selected from C(R₉₆)(R₉₇), N(R₉₆), O, and S,

R₉₁to R₉₃may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a phenoxy group, a phenylthio group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group,

R₉₄to R₉₇may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenoxy group, a phenylthio group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

a91 may be selected from 1, 2, 3, 4, and 5,

a92 may be selected from 1, 2, 3, 4, 5, 6, and 7,

a93 may be selected from 1, 2, 3, 4, 5, and 6,

a94 may be selected from 1, 2, and 3,

a95 may be selected from 1, 2, 3, and 4, and

* indicates a binding site to a neighboring atom.

In various embodiments, in Formulae 2-1 to 2-4, R₂₁₁, R₂₁₂, R₂₂₁, R₂₂₂, R₂₃₅to R₂₃₈, and R₂₄₂may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, an iso-propoxy group, an n-butoxy group, an iso-butoxy group, a sec-butoxy group, a tert-butoxy group, —Si(CH₃)₃, —Si(Ph)₃, —N(Ph₂)₂, —B(Ph)₂, and a group represented by any of Formulae 10-1 to 10-26, but embodiments of the present disclosure are not limited thereto:

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In Formulae 10-1 to 10-26,

* indicates a binding site to a neighboring atom.

In Formulae 2-1 to 2-4, b211, b212, b221, b222, b235 to b238, and b242 may each independently be selected from 1, 2, and 3. For example, in Formulae 2-1 to 2-4, b211, b212, b221, b222, b235 to b238, and b242 may each independently be selected from 1 and 2, but embodiments of the present disclosure are not limited thereto.

In Formulae 2-1 and 2-2, n211, n212, and n221 may each independently be selected from 1, 2, and 3.

In Formula 2-3, n231 to n234 may each independently be selected from 0, 1, and 2, wherein the sum of n231, n232, n233 and n234 may be selected from 1, 2, 3, 4, 5, and 6.

In Formula 2-4, n241 may be selected from 3, 4, 5, 6, 7, and 8.

For example, the second compound represented by one selected from Formulae 2-1 to 2-4 may be represented by one of Formulae 2-11 to 2-16, but embodiments of the present disclosure are not limited thereto:

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In Formulae 2-11 to 2-16,

Ar₂₄₁, L₂₁₁to L₂₁₃, L₂₂₁, L₂₃₁to L₂₃₄, L₂₄₁, a211 to a213, a221, a231 to a234, a241, R₂₃₁to R₂₃₄, R₂₄₁, b231 to b234, b241, R₂₁₁, R₂₁₂, R₂₂₁, R₂₂₂, R₂₃₅to R₂₃₈, R₂₄₂, b211, b212, b221, b222, b235 to b238, b242, n211, and n212 may each independently be the same as respectively defined in Formulae 2-1 to 2-4,

R₂₄₃to R₂₄₇may each independently be defined the same as R₂₄₁in Formula 2-3,

b243 to b247 may each independently be defined the same as b241 in Formula 2-4,

L₂₂₂may be defined the same as L₂₂₁in Formula 2-2,

a222 may be defined the same as a221 in Formula 2-2,

R₂₂₃may be defined the same as R₂₂₁in Formula 2-2,

b223 may be defined the same as b221 in Formula 2-2,

L₂₄₂to L₂₄₆may each independently be defined the same as L₂₄₁in Formula 2-4, and

a242 to a246 may each independently be defined the same as a241 in Formula 2-4.

In various embodiments, the second compound represented by one selected from Formulae 2-1 to 2-4 may be represented by one selected from Formulae 2-21 to 2-29, but embodiments of the present disclosure are not limited thereto:

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In Formulae 2-21 to 2-29,

R₂₂₄may be defined the same as R₂₂₂in Formula 2-2,

L₂₂₂may be defined the same as L₂₂₁in Formula 2-2,

a222 may be defined the same as a221 in Formula 2-2,

R₂₂₃may be defined the same as R₂₂₁in Formula 2-2,

b223 may be defined the same as b221 in Formula 2-2,

L₂₄₂to L₂₄₆may each independently be defined the same as L₂₄₁in Formula 2-4,

a242 to a246 may each independently be defined the same as a241 in Formula 2-4,

R₂₄₃to R₂₄₇may each independently be defined the same as R₂₄₁in Formula 2-4,

R₂₄₈and R₂₄₉may each independently be defined the same as R₂₄₂in Formula 2-4,

b243 to b247 may each independently be defined the same as b241 in Formula 2-4, and

b248 and b249 may each independently be defined the same as b242 in Formula 2-4.

In various embodiments, the second compound represented by one selected from Formulae 2-1 to 2-4 may be selected from Compounds H-1 to H-68, but embodiments of the present disclosure are not limited thereto:

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The first compound represented by Formula 1 may include a benzochrysene core. Accordingly, due to the inclusion of the benzochrysene core in the first compound represented by Formula 1, the organic light-emitting device including the first compound represented by Formula 1 may exhibit blue fluorescence with strong intensity.

It is generally known that an amine-based compound including a chrysene core can only be utilized to synthesize a symmetrically-structured amine derivative. However, since the first compound represented by Formula 1 includes the benzochrysene core, an asymmetrically-structured amine derivative can be synthesized.

Since the first compound represented by Formula 1 may have a variety of substituents, the organic light-emitting device including the first compound represented by Formula 1 may exhibit various electric characteristics and emission characteristics.

Therefore, the organic light-emitting device including the first compound represented by Formula 1 may have low driving voltage, high efficiency, high luminance, long lifespan, and/or high color purity.

Since the second compound represented by one selected from Formulae 2-1 to 2-4 and the first compound represented by Formula 1 may facilitate energy transfer therebetween, the organic light-emitting device including the first compound represented by Formula 1 and the second compound represented by one selected from Formulae 2-1 to 2-4 may have improved efficiency.

The first compound represented by Formula 1 and the second compound represented by one selected from Formulae 2-1 to 2-4 may be synthesized utilizing a suitable organic synthesis method.

For example, the emission layer may include the first compound represented by Formula 1 and the second compound represented by one selected from Formulae 2-1 to 2-4, but embodiments of the present disclosure are not limited thereto.

When the emission layer includes the first compound represented by Formula 1 and the second compound represented by one selected from Formulae 2-1 to 2-4, the first compound represented by Formula 1 may be a dopant and the second compound represented by one selected from Formulae 2-1 to 2-4 may be a host, but embodiments of the present disclosure are not limited thereto.

The organic layer 150 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 190.

Hole Transport Region in Organic Layer 150

The hole transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.

The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer, but embodiments of the present disclosure are not limited thereto

For example, the hole transport region may have a single-layered structure including a single layer including a plurality of different materials, or a multi-layered structure having a structure of hole injection layer/hole transport layer, a structure of hole injection layer/hole transport layer/emission auxiliary layer, a structure of hole injection layer/emission auxiliary layer, a structure of hole transport layer/emission auxiliary layer, or a structure of hole injection layer/hole transport layer/electron blocking layer, wherein, for each structure, constituting layers are sequentially stacked from the first electrode 110 in the stated order, but the structure of the hole transport region is not limited thereto.

When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 110 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 (LITI).

When the hole injection layer is formed by vacuum deposition, for example, the vacuum deposition may be performed at a deposition temperature of about 100 to about 500° C., at a vacuum degree of about 10⁻⁸to about 10⁻³torr, and at a deposition rate of about 0.01 to about 100 Å/sec by taking into account a material for a hole injection layer to be deposited and the structure of a hole injection layer to be formed.

When the hole injection layer is formed by spin coating, for example, the spin coating may be performed at a coating rate of about 2,000 rpm to about 5,000 rpm and at a temperature of about 80 to about 200° C. by taking into account a material for a hole injection layer to be deposited and the structure of a hole injection layer to be formed.

When the hole transport region includes a hole transport layer, the hole transport layer may be formed on the first electrode 110 or the hole injection layer by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, LB deposition, ink-jet printing, laser-printing, and LITI. When the hole transport layer is formed by vacuum deposition and/or spin coating, deposition and coating conditions for the hole transport layer may be the same as the deposition and coating conditions for the hole injection layer.

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

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In Formulae 201 and 202,

L₂₀₁to L₂₀₅may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be selected from 0, 1, 2, and 3,

xa5 may be selected from 1, 2, 3, 4, and 5, and

R₂₀₁to R₂₀₄may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formulae 201 and 202,

L₂₀₁to L₂₀₅may each independently be selected from the group consisting of:

Q₃₁to Q₃₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

In various embodiments, in Formulae 201 and 202,

xa1 to xa4 may each independently be 0, 1, or 2,

xa5 may be 1, 2, or 3,

R₂₀₁to R₂₀₄may each independently be selected from the group consisting of:

Q₃₁to Q₃₃may be each independently understood by referring to the descriptions thereof provided in the present specification.

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

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For example, the compound represented by Formula 201 may be represented by Formula 201A-1, but embodiments of the present disclosure are not limited thereto:

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The compound represented by Formula 202 may be represented by Formula 202A, but embodiments of the present disclosure are not limited thereto:

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In Formulae 201A, 201A-1, and 202A,

L₂₀₁to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂to R₂₀₄may each independently be understood by referring to the descriptions thereof provided in the present specification,

R₂₁₁and R₂₁₂may each independently be the same as described herein in connection with R₂₀₃, and

R₂₁₃to R₂₁₆may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group.

R₂₁₃and R₂₁₄in Formulae 201A and 201A-1 may optionally be linked to form a saturated or unsaturated ring.

The compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of Compounds HT1 to HT20, but embodiments of the present disclosure are not limited thereto:

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A thickness of the hole transport region may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, a thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within 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 according to the wavelength of the light emitted by the emission layer, and the electron blocking layer may block the flow of electrons from the electron transport region. The emission auxiliary layer and the electron blocking layer may include the materials described above.

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 homogeneously or non-homogeneously dispersed in the hole transport region.

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

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

The p-dopant may be one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto.

For example, the p-dopant may include at least one selected from the group consisting of:

a quinone derivative, such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

a metal oxide, such as tungsten oxide and a molybdenum oxide;

1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221, but embodiments of the present disclosure are not limited thereto:

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In Formula 221,

R₂₂₁to R₂₂₃may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein at least one selected from R₂₂₁to R₂₂₃has at least one substituent selected from a cyano group, —F, —Cl, —Br, —I, a C₁-C₂₀alkyl group substituted with —F, a C₁-C₂₀alkyl group substituted with —Cl, a C₁-C₂₀alkyl group substituted with —Br, and a C₁-C₂₀alkyl group substituted with —I.

Emission Layer in Organic Layer 150

The emission layer may be formed on the first electrode 110 or the hole transport region by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, LB deposition, ink-jet printing, laser-printing, and LITI. When the emission layer is formed by vacuum deposition and/or spin coating, deposition and coating conditions for the emission layer may be the same as the deposition and coating conditions for the hole injection layer.

When the organic light-emitting device 10 is a full color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer, according to an individual sub-pixel. In various embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other. In various embodiments, the emission layer may include two or more materials selected from a red-light emission material, a green-light emission material, and a blue-light emission material, in which the two or more materials are mixed with each other in a single layer to emit white light. In various embodiments, the emission layer may be a white-light emission layer, and may further include a color converting layer or a color filter to turn white light into light of a desired color.

The emission layer may include a host and a dopant.

The host may include the second compound represented by one selected from Formulae 2-1 to 2-4.

The dopant may include the first compound represented by Formula 1.

In the emission layer, a weight ratio of the first compound to the second compound may be in a range of about 1:99 to about 20:80, but embodiments of the present disclosure are not limited thereto. In various embodiments, a weight ratio of the first compound to the second compound may be in a range of about 1:99 to about 10:90, but embodiments of the present disclosure are not limited thereto. In various embodiments, a weight ratio of the first compound to the second compound may be in a range of about 3:97 to about 5:95, but embodiments of the present disclosure are not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. 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.

Electron Transport Region in Organic Layer 150

The electron transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.

The electron transport region may include at least one layer selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of the present disclosure are not limited thereto.

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

When the electron transport region includes a hole blocking layer, the hole blocking layer may be formed on the emission layer by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, LB deposition, ink-jet printing, laser-printing, and LITI. When the hole blocking layer is formed by vacuum deposition and/or spin coating, deposition and coating conditions for the hole blocking layer may be the same as the deposition and coating conditions for the hole injection layer.

The hole blocking layer may include, for example, at least one selected from BCP and Bphen, but embodiments of the present disclosure are not limited thereto:

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A thickness of a buffer layer, a hole blocking layer, or an electron control layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thickness of the buffer layer, the hole blocking layer, and/or the electron control layer is within these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.

The electron transport region may include an electron transport layer. The electron transport layer may be formed on the emission layer or the hole blocking layer by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, LB deposition, ink-jet printing, laser-printing, and LITI. When the electron transport layer is formed by vacuum deposition and/or spin coating, deposition and coating conditions for the electron transport layer may be the same as the deposition and coating conditions for the hole injection layer.

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

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In various embodiments, the electron transport layer may include at least one of compounds represented by Formula 601:

Ar₆₀₁-[(L₆₀₁)_xe1-E₆₀₁]_xe2. Formula 601

In Formula 601, Ar₆₀₁may be selected from the group consisting of:

a naphthalene group, a heptalene group, a fluorene group, a spiro-fluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, and an indenoanthracene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

L₆₀₁may be the same as described herein in connection with L₂₀₁,

E₆₀₁may be selected from the group consisting of:

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 phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl 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, and a dibenzocarbazolyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl 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 phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl 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, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

xe1 may be selected from 0, 1, 2, and 3,

xe2 may be selected from 1, 2, 3, and 4, and

Q₃₁to Q₃₃may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

In various embodiments, the electron transport layer may include at least one of compounds represented by Formula 602:

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In Formula 602,

X₆₁₁may be N or C-(L₆₁₁)_xe611-R₆₁₁, X₆₁₂may be N or C-(L₆₁₂)_xe612-R₆₁₂, X₆₁₃may be N or C-(L₆₁₃)_xe613-R₆₁₃, wherein at least one selected from X₆₁₁to X₆₁₃may be N,

L₆₁₁to L₆₁₆may each independently be the same as described herein in connection with L₂₀₁,

R₆₁₁to R₆₁₆may each independently be selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an azulenyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

xe611 to xe616 may each independently be selected from 0, 1, 2, and 3, and

The compound represented by Formula 601 and the compound represented by Formula 602 may each independently include at least one selected from Compounds ET1 to ET15:

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A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.

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

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

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The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may directly contact the second electrode 190.

The electron injection layer may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.

The electron injection layer may be formed on the electron transport layer by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, LB deposition, ink-jet printing, laser-printing, and LITI. When the electron injection layer is formed by vacuum deposition and/or spin coating, deposition and coating conditions for the electron injection layer may be the same as the deposition and coating conditions for the hole injection layer.

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

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

Second Electrode 190

The second electrode 190 may be disposed on the organic layer 150 having such a structure described above. The second electrode 190 may be a cathode which is an electron injection electrode, and in this regard, a material for the second electrode 190 may be selected from a metal, an alloy, an electrically conductive compound, and a combination thereof, which may have a relatively low work function.

The second electrode 190 may include at least one selected from Li, silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode.

The second electrode 190 may have a single-layered structure, or a multi-layered structure including two or more layers.

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

Descriptions of FIGS. 2 to 4

An organic light-emitting device 20 of FIG. 2 includes a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are sequentially stacked in the stated order; an organic light-emitting device 30 of FIG. 3 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are sequentially stacked in the stated order; and an organic light-emitting device 40 of FIG. 4 includes a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are sequentially stacked in the stated order.

In FIGS. 2 to 4, the first electrode 110, the organic layer 150, and the second electrode 190 may each independently be the same as respectively described herein in connection with FIG. 1.

In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in an emission layer may pass through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer 210 toward the outside; and/or in the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in an emission layer may pass through the second electrode 190, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer 220 toward the outside.

The first capping layer 210 and the second capping layer 220 may increase external luminescent efficiency according to the principle of constructive interference.

The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.

At least one selected from the first capping layer 210 and the second capping layer 220 may include at least one material selected from a carbocyclic compound, a heterocyclic compound, an amine-based compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkaline metal complex, and an alkaline earth-metal complex. The carbocyclic compound, the heterocyclic compound, and the amine-based compound may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In various embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may include the amine-based compound.

In various embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may include the compound represented by Formula 201 or the compound represented by Formula 202.

In various embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may include a compound selected from Compounds HT13 to HT20 and Compounds CP1 to CP5, but embodiments of the present disclosure are not limited thereto.

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Hereinabove, the organic light-emitting device has been described with reference to FIGS. 1 to 4, but embodiments of the present disclosure are not limited thereto.

Layers constituting the hole transport region, the emission layer, and layers constituting 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, LB deposition, ink-jet printing, laser-printing, and LITI.

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

When layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region are each formed by spin coating, for example, the spin coating may be performed at a coating rate of about 2,000 rpm to about 5,000 rpm and at a temperature of about 80° C. to about 200° C., by taking into account a material to be included in a layer to be formed and a structure of the layer to be formed.

General Definition of Substituents

The term “C₁-C₆₀alkyl group” as used herein refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a ter-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. The term “C₁-C₆₀alkylene group” as used herein refers to a divalent group having substantially the same structure as the C₁-C₆₀alkyl group.

The term “C₂-C₆₀alkenyl group” as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond at one or more positions along the hydrocarbon chain of the C₂-C₆₀alkyl group (e.g., in the middle or at either terminal end of the C₂-C₆₀alkyl group), and examples thereof include an ethenyl group, propenyl group, and a butenyl group. The term “C₂-C₆₀alkenylene group” as used herein refers to a divalent group having substantially the same structure as the C₂-C₆₀alkenyl group.

The term “C₂-C₆₀alkynyl group” as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond at one or more positions along the hydrocarbon chain of the C₂-C₆₀alkyl group (e.g., in the middle or at either terminal end of the C₂-C₆₀alkyl group), and examples thereof include an ethynyl group and a propynyl group. The term “C₂-C₆₀alkynylene group” as used herein refers to a divalent group having substantially the same structure as the C₂-C₆₀alkynyl group.

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

The term “C₃-C₁₀cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C₃-C₁₀cycloalkylene group” as used herein may refer to a divalent group having substantially the same structure as the C₃-C₁₀cycloalkyl group.

The term “C₁-C₁₀heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom in addition to 1 to 10 carbon atoms, and examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C₁-C₁₀heterocycloalkylene group” as used herein refers to a divalent group having substantially the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and does not have aromaticity, and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group having substantially the same structure as the C₃-C₁₀cycloalkenyl group.

The term “C₁-C₁₀heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom in addition to 1 to 10 carbon atoms, and at least one carbon-carbon double bond in the ring. Examples of the C₁-C₁₀heterocycloalkenyl group 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 refers to a divalent group having substantially the same structure as the C₁-C₁₀heterocycloalkenyl group.

The term “C₆-C₆₀aryl group” as used herein refers to a monovalent group having an aromatic system having 6 to 60 carbon atoms, and the term “C₆-C₆₀arylene group” as used herein refers to a divalent group having an aromatic system having 6 to 60 carbon atoms. Examples of the C₆-C₆₀aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀aryl group and the C₆-C₆₀arylene group each independently include two or more rings, the respective rings may be fused to each other or may be linked with each other via a single bond.

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom in addition to 1 to 60 carbon atoms. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom in addition to 1 to 60 carbon atoms. Examples of the C₁-C₆₀heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀heteroarylene group each independently include two or more rings, the respective rings may be fused to each other or may be linked with each other via a single bond.

The term “C₆-C₆₀aryloxy group” as used herein refers to a group represented by —OA₁₀₂(where A₁₀₂is the C₆-C₆₀aryl group), and the term “C₆-C₆₀arylthio group” as used herein refers to a group represented by —SA₁₀₃(where A₁₀₃is the C₆-C₆₀aryl group).

The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group that has two or more rings condensed to each other, has only carbon atoms as ring-forming atoms (for example, 8 to 60 carbon atoms), and has non-aromaticity in the entire molecular structure. An example of the monovalent non-aromatic condensed polycyclic group includes a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group that has two or more rings condensed to each other, has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom in addition to carbon atoms (for example, 1 to 60 carbon atoms), and has non-aromaticity in the entire molecular structure. An example of the monovalent non-aromatic condensed heteropolycyclic group includes a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

The term “C₅-C₆₀carbocyclic group” as used herein refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms in which the ring-forming atoms include only carbon atoms. The C₅-C₆₀carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C₅-C₆₀carbocyclic group may be a ring (such as a benzene group), a monovalent group (such as a phenyl group), or a divalent group (such as a phenylene group). In various embodiments, depending on the number of substituents connected to the C₅-C₆₀carbocyclic group, the C₅-C₆₀carbocyclic group may be a trivalent group or a quadrivalent group.

The term “C₁-C₆₀heterocyclic group” as used herein refers to a group having substantially the same structure as the C₅-C₆₀carbocyclic group except that as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S is used in addition to one or more carbon atoms (the number of carbon atoms in the C₁-C₆₀heterocyclic group may be in a range of 1 to 60).

In the present specification, at least one substituent of the substituted C₅-C₆₀carbocyclic group, the substituted C₁-C₆₀heterocyclic group, the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₁₀heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from the group consisting of:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group;

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and

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

Q₁₁to Q₁₃, Q₂₁to Q₂₃, and Q₃₁to Q₃₃may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

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 term “ter-Bu” or “But” as used herein refers to a tert-butyl group, the term “OMe” as used herein refers to a methoxy group, and the term “D” as used herein refers to deuterium.

The term “biphenyl group” as used herein refers to “a phenyl group substituted with a phenyl group”. The term “biphenyl group” as used herein belongs to “a substituted phenyl group” having “a C₆-C₆₀aryl group” as a substituent.

The term “terphenyl group” as used herein refers to “a phenyl group substituted with a biphenyl group”. The term “terphenyl group” as used herein belongs to “a substituted phenyl group” having “a C₆-C₆₀aryl group substituted with a C₆-C₆₀aryl group” as a substituent.

* and *′ as used herein, unless defined otherwise, each indicate a binding site to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to one or more embodiments and an organic light-emitting device according to one or more embodiments will be described in more detail with reference to the Synthesis Examples and Examples. The phrase “B was utilized instead of A” used in describing the Synthesis Examples refers to that an identical number of molar equivalents of B was utilized in place of molar equivalents of A.

EXAMPLES
Synthesis Example 1: Synthesis of Compound 2

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1) Synthesis of Intermediate A-1

6.34 g (20 mmol) of 2-bromo-4-chloro-1-iodobenzene, 0.190 g (1 mmol) of CuI, 1.155 g (1 mmol) of (Ph₃)₄Pd, and 1.96 g (20 mmol) of ethynyltrimethylsilane were dissolved in 200 ml of anhydrous THF under a nitrogen atmosphere, and then, 3.066 g (30 mmol) of triethylamine was slowly added dropwise to the mixed solution. After 3 hours, an extraction process was performed thereon once utilizing 100 ml of water and three times utilizing 10 ml of diethylether. An organic layer collected therefrom was dried utilizing magnesium sulfate, and a solvent was removed therefrom by evaporation. The residue obtained therefrom was purified by silica gel column chromatography, thereby completing the preparation of 5.113 g (18 mmol, yield: 90%) of Intermediate A-1.

2) Synthesis of Intermediate A-2

5.113 g (18 mmol) of Intermediate A-1, 2.44 g (20 mmol) of phenylboronic acid, 1.155 g (1 mmol) of Pd(PPh₃)₄, and 2.762 g (20 mmol) of K₂CO₃were dissolved in 200 ml of a tetrahydrofuran (THF)/H₂O solution (mixed at a volume ratio of 2/1) under a nitrogen atmosphere, and then, the mixed solution was stirred at a temperature of 80° C. for 12 hours. After the reaction solution was cooled to room temperature, an extraction process was performed thereon once utilizing 50 ml of water and three times utilizing 150 ml of ethylether. An organic solvent layer collected therefrom was dried utilizing magnesium sulfate, and a solvent was removed therefrom by evaporation. The residue obtained therefrom was purified by silica gel column chromatography, thereby completing the preparation of 4.26 g (15 mmol, yield: 83%) of Intermediate A-2.

3) Synthesis of Intermediate A-3

4.26 g (15 mmol) of Intermediate A-2 and 0.800 g (20 mmol) of sodium hydroxide were added to 100 ml of methanol. The mixed solution was stirred at a temperature of 60° C. for 1 hour. An extraction process was performed thereon once utilizing 50 ml of water and three times utilizing 50 ml of ethylether. An organic solvent layer collected therefrom was dried utilizing magnesium sulfate, and a solvent was removed therefrom by evaporation. The residue obtained therefrom was purified by silica gel column chromatography, thereby completing the preparation of 2.968 g (14 mmol, yield: 93%) of Intermediate A-3.

4) Synthesis of Intermediate A-4

3.678 g (10 mmol, yield: 71%) of Intermediate A-4 was prepared in substantially the same manner as in synthesizing Intermediate A-1 of Synthesis Example 1, except that 1-bromo-4-iodine-benzene and Intermediate A-3 were utilized instead of 2-bromo-4-chloro-1-iodobenzene and ethynyltrimethylsilane, respectively.

5) Synthesis of Intermediate A-5

3.678 g (10 mmol) of Intermediate A-4 was dissolved in 100 ml of dichloromethane, and 1.622 g of ICl was slowly added dropwise thereto. An extraction process was performed thereon once utilizing 50 ml of water and three times utilizing 10 ml of dichloromethane. An organic solvent layer collected therefrom was dried utilizing magnesium sulfate, and a solvent was removed therefrom by evaporation. The residue obtained therefrom was purified by silica gel column chromatography, thereby completing the preparation of 4.437 g (9 mmol, yield: 90%) of Intermediate A-5.

6) Synthesis of Intermediate A-6

3.756 g (8.1 mmol, yield: 90%) of Intermediate A-6 was prepared in substantially the same manner as in synthesizing Intermediate A-1 of Synthesis Example 1, except that Intermediate A-5 was utilized instead of 2-bromo-4-chloro-1-iodobenzene.

7) Synthesis of Intermediate A-7

2.741 g (7 mmol, yield: 87%) of Intermediate A-7 was prepared in substantially the same manner as in synthesizing Intermediate A-3 of Synthesis Example 1, except that Intermediate A-6 was utilized instead of Intermediate A-2.

8) Synthesis of Intermediate A

2.741 g (7 mmol) of Intermediate A-7 and 0.092 g (0.35 mmol) of PtCl₂were dissolved in 50 ml of toluene, and then, the mixed solution was stirred at a temperature of 100° C. for 12 hours. An extraction process was performed on the reaction solution once utilizing 50 ml of water and three times utilizing 50 ml of ethylether. An organic solvent layer collected therefrom was dried utilizing magnesium sulfate, and a solvent was removed therefrom by evaporation. The residue obtained therefrom was purified by silica gel column chromatography, thereby completing the preparation of 1.564 g (4 mmol, yield: 57%) of Intermediate A.

9) Synthesis of Compound 2

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0.391 g (1 mmol) of Intermediate A, 0.855 g (3 mmol) of 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine, 0.091 g (0.1 mmol) of tris(dibenzylidene acetone)dipalladium(0) (Pd₂(dba)₃), 0.020 g (0.1 mmol) of tris-tert-butylphosphine, and 0.28 g (3 mmol) of KOtBu were dissolved in 60 ml of toluene under a nitrogen atmosphere, and then, the mixed solution was stirred at a temperature of 90° C. for 4 hours. After the reaction solution was cooled to room temperature, an extraction process was performed thereon once utilizing 50 ml of water and three times utilizing 50 ml of diethylether. An organic solvent layer collected therefrom was dried utilizing magnesium sulfate, and a solvent was removed therefrom by evaporation. The residue obtained therefrom was purified by silica gel column chromatography, thereby completing the preparation of 0.720 g (0.85 mmol, yield: 86%) of Compound 2.

Synthesis Example 2: Synthesis of Compound 72

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1) Synthesis of Intermediate 72-1

0.500 g (0.87 mmol, yield: 87%) of Intermediate 72-1 was prepared in substantially the same manner as in synthesizing Compound 2 of Synthesis Example 1, except that N-phenyldibenzo[b,d]furan-4-amine was utilized instead of 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine.

2) Synthesis of Compound 72

0.492 g (0.6 mmol, 69%) of Compound 72 was prepared in substantially the same manner as in synthesizing Compound 2 of Synthesis Example 1, except that Intermediate 72-1 was utilized instead of Intermediate A.

Other additional compounds were synthesized by utilizing the same synthesis methods described above and appropriate intermediate materials. It should be apparent to one of ordinary skill in the art to synthesize other compounds, in addition to the compounds specifically described in the present specification, according to the synthesis methods and the raw materials described above.

Example 1

An anode was prepared by cutting a glass substrate (Corning), on which ITO having a thickness of 15 Ω/cm²(1,200 Å) was formed, to a size of 50 mm×50 mm×0.7 mm, ultrasonically cleaning the glass substrate by utilizing isopropyl alcohol and pure water for 5 minutes each, and then irradiating UV light for 10 minutes thereto and exposing the glass substrate to ozone to clean the glass substrate. Then, the anode was loaded into a vacuum deposition apparatus.

2-TNATA was deposited on the anode to form a hole injection layer having a thickness of 600 Å, and then, NPB was deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å. Compound H-4 and Compound 2 were co-deposited on the hole transport layer at a ratio of 98:2 to form an emission layer having a thickness of 300 Å.

Alq₃was deposited on the emission layer to form an electron transport layer having a thickness of 300 Å, and LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å. Then, Al was vacuum-deposited on the electron injection layer 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 12 and Comparative Examples 1 to 10

Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that compounds shown in Table 1 were utilized instead of Compound 2 and Compound H-4 in the formation of the emission layer.

TABLE 1

First
Second

compound
compound

Example 1
Compound 2
Compound

H-4

Example 2
Compound 38
Compound

H-4

Example 3
Compound 9
Compound

H-11

Example 4
Compound 55
Compound

H-11

Example 5
Compound 10
Compound

H-17

Example 6
Compound 57
Compound

H-17

Example 7
Compound 13
Compound

H-36

Example 8
Compound 72
Compound

H-36

Example 9
Compound 15
Compound

H-52

Example 10
Compound 88
Compound

H-52

Example 11
Compound 18
Compound

H-57

Example 12
Compound 90
Compound

H-57

Comparative
DPAVBi
ADN

Example 1

Comparative
TPD
ADN

Example 2

Comparative
Compound
Compound

Example 3
B-1
A-1

Comparative
Compound
Compound

Example 4
B-1
A-2

Comparative
Compound
Compound

Example 5
B-1
A-3

Comparative
Compound
Compound

Example 6
B-2
A-4

Comparative
Compound
Compound

Example 7
B-3
A-5

Comparative
Compound
Compound

Example 8
B-3
A-6

Comparative
Compound
Compound

Example 9
B-3
A-7

Comparative
Compound
Compound

Example 10
B-4
A-7

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Evaluation Example 1

The driving voltage, current density, luminance, efficiency, and half lifespan of the organic light-emitting devices manufactured in Examples 1 to 12 and Comparative Examples 1 to 10 were evaluated utilizing a Keithley 236 source-measure unit (SMU) and a PR650 luminance meter, and the results are shown in Table 2. Here, the half lifespan results were obtained by measuring the time at which the luminance of an organic light-emitting device was 50% of the initial luminance after being driven.

TABLE 2

Driving
Current

Half

First
Second
voltage
density
Luminance
Efficiency
Emission
lifespan (hr

compound
compound
(V)
(mA/cm²)
(cd/m²)
(cd/A)
color
@100 mA/cm²)

Example 1
Compound 2
Compound
5.82
50
3540
7.08
blue
348

H-4

Example 2
Compound 38
Compound
5.78
50
3560
7.12
blue
352

H-4

Example 3
Compound 9
Compound
5.82
50
3335
6.67
blue
374

H-11

Example 4
Compound 55
Compound
5.88
50
3360
6.72
blue
370

H-11

Example 5
Compound 10
Compound
5.84
50
3570
7.14
blue
382

H-17

Example 6
Compound 57
Compound
5.76
50
3545
7.09
blue
335

H-17

Example 7
Compound 13
Compound
5.84
50
3640
7.28
blue
363

H-36

Example 8
Compound 72
Compound
5.79
50
3375
6.75
blue
347

H-36

Example 9
Compound 15
Compound
5.87
50
3585
7.17
blue
382

H-52

Example 10
Compound 88
Compound
5.75
50
3475
6.95
blue
348

H-52

Example 11
Compound 18
Compound
5.98
50
3440
6.88
blue
355

H-57

Example 12
Compound 90
Compound
5.92
50
3625
7.25
blue
344

H-57

Comparative
DPAVBi
DNA
7.01
50
2645
5.29
blue
258

Example 1

Comparative
TPD
DNA
6.96
50
2730
5.46
blue
248

Example 2

Comparative
Compound
Compound
7.21
50
2660
5.32
blue
262

Example 3
B-1
A-1

Comparative
Compound
Compound
7.15
50
2690
5.38
blue
254

Example 4
B-1
A-2

Comparative
Compound
Compound
8.18
50
2525
5.05
blue
225

Example 5
B-1
A-3

Comparative
Compound
Compound
8.07
50
2445
4.89
blue
192

Example 6
B-2
A-4

Comparative
Compound
Compound
7.23
50
2620
5.24
blue-
248

Example 7
B-3
A-5

green

Comparative
Compound
Compound
7.54
50
2570
5.14
blue-
245

Example 8
B-3
A-6

green

Comparative
Compound
Compound
7.03
50
2675
5.35
blue-
230

Example 9
B-3
A-7

green

Comparative
Compound
Compound
7.05
50
2610
5.22
blue-
234

Example 10
B-4
A-7

green

Referring to Table 2, it was confirmed that the organic light-emitting devices manufactured in Examples 1 to 12 exhibited excellent characteristics, as compared with the organic light-emitting devices manufactured in Comparative Examples 1 to 10.

As described above, an organic light-emitting device according to one or more embodiment may have improved driving voltage, improved luminance, improved efficiency, improved color purity, and/or long lifespan characteristics.

It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments.

While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims, and equivalents thereof.

Number	Date	Country	Kind
10-2015-0063220	May 2015	KR	national
10-2016-0029102	Mar 2016	KR	national

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10-2016-0086482	Jul 2016	KR
200940682	Oct 2009	TW
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201300350	Jan 2013	TW
WO 2004018588	Mar 2004	WO

Organic light-emitting device

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US Referenced Citations (24)

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Non-Patent Literature Citations (3)

Related Publications (1)

Entry
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