ORGANIC LIGHT-EMITTING DEVICE

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority under 35 U.S.C. § 119 to Korean Patent Application No. 10-2020-0178364, filed on Dec. 18, 2020, in the Korean Intellectual Property Office, the content of which is incorporated by reference herein in its entirety.

BACKGROUND
1. Field

Provided is an organic light-emitting device.

2. Description of the Related Art

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

In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be located between the anode and the emission layer, and an electron transport region may be located between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state to thereby generate light.

SUMMARY

One or more embodiments provide a new organic light-emitting device.

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

According to one or more embodiments, a light-emitting device including: a first electrode,

a second electrode; and

an organic layer between the first electrode and the second electrode and including an emission layer,

wherein the organic layer includes at least one condensed cyclic compound represented by Formula 1.

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In Formula 1,

ring A₁and ring A₂are each independently a C₅-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group,

L₁is a single bond, a C₅-C₃₀carbocyclic group unsubstituted or substituted with at least one R_10a, or a C₁-C₃₀heterocyclic group unsubstituted or substituted with at least one R_10a,

a1 is an integer from 1 to 5,

Ar₁and Ar₂are each independently a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

R₁to R₄, R₁₀, R₂₀, and R_10aare each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a 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(Q₄)(Q₅), or —B(Q₆)(Q₇),

b1 to b4 are each independently an integer from 0 to 2,

b10 and b20 are each independently an integer from 0 to 10,

at least one substituent of the substituted C₅-C₆₀carbocyclic group, the substituted C₁-C₆₀heterocyclic 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 is selected from

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

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

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇)₇or any combination thereof; or

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₄)(Q₃₅), or —B(Q₃₆)(Q₃₇),

wherein Q₁to Q₇, Q₁₁to Q₁₇, Q₂₁to Q₂₇, and Q₃₁to Q₃₇are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl 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 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

According to an aspect of another embodiment, an organic light-emitting device includes: a first electrode; a second electrode; m emission units between the first electrode and the second electrode and including at least one emission layer; and

m−1 charge generating layers between neighboring two emission units of the m emission units and including an n-type charge generating layer and a p-type charge generating layer,

wherein m is an integer of 2 or more,

the maximum emission wavelength of light emitted from at least one emission unit of the m emission units may be different from the maximum emission wavelength of light emitted from at least one emission unit of the remaining emission units among the m emission units, and

the emission layer includes the at least one condensed cyclic compound.

According to an aspect of another embodiment, an organic light-emitting device includes: a first electrode; a second electrode; and m emission layers between the first electrode and the second electrode,

wherein m is an integer of 2 or more,

the maximum emission wavelength of light emitted from at least one emission layer of the m emission layers may be different from the maximum emission wavelength of light emitted from at least one emission layer of the remaining emission layers among the m emission layers, and

the emission layer includes the at least one condensed cyclic compound.

BRIEF DESCRIPTION OF THE DRAWINGS

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

FIGS. 1, 2, and 3 each show a schematic cross-sectional view of an organic light-emitting device according to an exemplary embodiment.

DETAILED DESCRIPTION

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

It will be understood that when an element is referred to as being “on” another element, it can be directly on the other element or intervening elements may be present therebetween In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present

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

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

“Or” means “and/or.” As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.

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

“About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ±30%, 20%, 10% or 5% of the stated value.

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

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

In an embodiment, provided is an organic light-emitting device including a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one type of condensed cyclic compound represented by Formula 1.

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Ring A₁and ring A₂in Formula 1 may each independently be a C₅-C₃₀carbocyclic group or a C₁-C₆₀heterocyclic group.

In an embodiment, ring A₁and ring A₂in Formula 1 may each independently be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a triindolobenzene group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, a benzoisoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, or a condensed ring of any combination thereof.

For example, ring A₁and ring A₂in Formula 1 may be identical to or different from each other.

For example, ring A₁and ring A₂in Formula 1 may be a benzene group.

In Formula 1, L₁may be a single bond, a C₅-C₃₀carbocyclic group unsubstituted or substituted with at least one R_10a, or a C₁-C₃₀heterocyclic group unsubstituted or substituted with at least one R_10a.

In an embodiment, L₁in Formula 1 may be: a single bond, a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentacene group, a rubicene group, corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a triindolobenzene group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, a benzoisoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a triindolobenzene group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, a benzoisoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each substituted with at least one R_10a.

For example, L₁in Formula 1 may be a single bond.

a1 in Formula 1 may be the number of groups represented by L₁, and when a1 is 2 or more, two or more of L₁(s) may be identical to or different from each other.

Ar₁and Ar₂in Formula 1 may each independently be a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group.

In an embodiment, Ar₁and Ar₂in Formula 1 may each independently be: 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-bifluorenyl 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 pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a thiophenyl group, a furanyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzonaphthofuranyl group, a dinaphthofuranyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a benzonaphthosilolyl group, a dinaphthosilolyl group, a benzimidazolyl group, or an imidazopyridinyl 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-bifluorenyl 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 pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a thiophenyl group, a furanyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzonaphthofuranyl group, a dinaphthofuranyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a benzonaphtho silolyl group, a dinaphtho silolyl group, a benzimidazolyl group, or an imidazopyridinyl group, each substituted with at least one —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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-bifluorenyl 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 pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a thiophenyl group, a furanyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), or any combination thereof,

wherein Q₃₁to Q₃₇may each independently be a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a pyridinyl group.

For example, Ar₁and Ar₂in Formula 1 may each independently be a biphenyl group and a terphenyl group; and a biphenyl group and a terphenyl group, each substituted with at least one C₁-C₂₀alkyl group.

For example, Ar₁and Ar₂in Formula 1 may each independently be a group represented by one of Formulae 2-1 to 2-17:

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In Formulae 2-1 to 2-17,

Z₃₁to Z₃₃may each independently be:

—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, or a C₁-C₂₀alkyl group; or

a C₁-C₂₀alkyl group substituted with at least one —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, or any combination thereof,

d3 may be an integer from 0 to 3,

d4 may be an integer from 0 to 4, and

d5 may be an integer from 0 to 5.

R₁to R₄, R₁₀, R₂₀, and R_10ain Formula 1 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a 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(Q₄)(Q₅), or —B(Q₆)(Q₇).

In an embodiment, R₁to R₄, R₁₀, R₂₀and R_10ain Formula 1 may each independently be: hydrogen, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF₅, a C₁-C₂₀alkyl group, or a C₁-C₂₀alkoxy group; or

a C₁-C₂₀alkyl group or a C₁-C₂₀alkoxy group, each substituted with at least one —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, or any combination thereof.

For example, R₁to R₄, R₁₀, R₂₀, and R_10ain Formula 1 may each independently be: hydrogen, a C₁-C₂₀alkyl group, or any combination thereof; or a C₁-C₂₀alkyl group substituted with a C₁-C₂₀alkyl group.

b1 to b4 in Formula 1 may each independently be an integer from 0 to 2 and b10 and b20 may each independently be an integer from 0 to 10.

b1 to b4, b10, and b20 in Formula 1 may each be the number of groups represented by R₁to R₄, R₁₀, and R₂₀, respectively, and when b1 is 2 or more, two or more of R₁(s) may be identical to or different from each other, when b2 is 2 or more, two or more of R₂(s) may be identical to or different from each other, when b3 is 2 or more, two or more of R₃(s) may be identical to or different from each other, when b4 is 2 or more, two or more of R₄(s) may be identical to or different from each other, when b10 is 2 or more, two or more of R₁₀(s) may be identical to or different from each other, and when b20 is 2 or more, two or more of R₂₀(s) may be identical to or different from each other.

At least one substituent of the substituted C₅-C₆₀carbocyclic group, the substituted C₁-C₆₀heterocyclic 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 is:

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

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₄)(Q₃₅), or —B(Q₃₆)(Q₃₇),

wherein Q₁to Q₇, Q₁₁to Q₁₇, Q₂₁to Q₂₇, and Q₃₁to Q₃₇may each independently be hydrogen, deuterium, —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl 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.

In an embodiment, Formula 1, a moiety represented by

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may independently be represented by one of Formulae 3-1 to 3-3:

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In Formulae 3-1 to 3-3,

Z₄₁to Z₄₃may each independently be:

—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, or a phenyl group; or

a C₁-C₂₀alkyl group or a phenyl group, each substituted with at least one —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, or any combination thereof,

Z₅₁to Z₅₄may each independently be:

a C₁-C₂₀alkyl group or a phenyl group; or

e3 may be an integer from 0 to 3, and

e4 may be an integer from 0 to 4.

In an embodiment, the condensed cyclic compound may be represented by one of Formulae 1-1 and 1-2:

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Ring A₁, ring A₂, L₁, a1, Ar₁, Ar₂, R₁to R₄, R₁₀, R₂₀, b1 to b4, b10, and b20 in Formulae 1-1 and 1-2 are the same as described above.

In an embodiment, the condensed cyclic compound may be represented by one of Formulae 1(1) and 1(2):

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Ring A₁, ring A₂, L₁, a1, Ar₁, Ar₂, R₁to R₄, R₁₀, R₂₀, b1 to b4, b10, and b20 in Formulae 1(1) and 1(2) are the same as described above.

In an embodiment, the condensed cyclic compound may be represented by one of Formulae 1A to 1E:

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Ring A₁, ring A₂, L₁, a1, Ar₁, Ar₂, R₁to R₄, R₁₀, R₂₀, b1 to b4, b10, and b20 in Formulae 1A and 1E are the same as described above.

In an embodiment, the condensed cyclic compound may have an asymmetric structure.

In an embodiment, the condensed cyclic compound may be one of Compounds FD1 to FD1051:

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In the condensed cyclic compound, a carbazole group and amine group may be asymmetrically substituted, thereby maintaining a light emission wavelength similar to that of a structure in which the amine group is symmetrically substituted into a pyrene core, while adjusting the HOMO energy level to be deeper to reduce hole traps to thereby increase lifespan.

In addition, by optionally substituting the carbazole group or the amine group of the condensed cyclic compound with a bulky non-emission unit or a functional group, the distance between phosphorescence or TADF molecules to be described later and the condensed cyclic compounds may be secured sufficiently, thereby suppressing Dexter energy transfer to improve efficiency.

In addition, as the condensed cyclic compound may have a structure wherein a pyrene core is in direct contact with a carbazole group without a linker, HOMO may be more effectively deepened and S1 may be increased. In addition, since LUMO does not spread widely including a linker but distributes only to a pyrene moiety, there may be an effect wherein the FWHM is reduced, which is in the important factor in a fluorescent dopant.

Condensed Cyclic Compound

According to an aspect, a condensed cyclic compound may be represented by Formula 1:

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In Formula 1,

ring A₁and ring A₂may each independently be a C₅-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group,

L₁may be a single bond, a C₅-C₃₀carbocyclic group unsubstituted or substituted with at least one R_10a, or a C₁-C₃₀heterocyclic group unsubstituted or substituted with at least one R_10a,

a1 may be an integer from 1 to 5,

Ar₁and Ar₂may each independently be a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

R₁to R₄, R₁₀, R₂₀, and R_10amay each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a 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(Q₄)(Q₅), or —B(Q₆)(Q₇),

b1 to b4 may each independently be an integer from 0 to 2,

b10 and b20 may each independently be an integer from 0 to 10,

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₄)(Q₃₅), or —B(Q₃₆)(Q₃₇),

wherein Q₁to Q₇, Q₁₁to Q₁₇, Q₂₁to Q₂₇, and Q₃₁to Q₃₇may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted heterocycloalkyl 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 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

Ring A₁, ring A₂, L₁, a1, Art Ar₂, R₁to R₄, R₁₀, R₂₀, R_10a, b1 to b4, b10, and b20 are the same as described above.

In an embodiment, at least one of Ar₁and Ar₂may be a group represented by Formula 2-1:

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Z₃₁, Z₃₂, d4, and d5 in Formula 2-1 are the same as described in the present specification, and * indicates a binding site to a neighboring atom.

In an embodiment, at least one of Ar₁and Ar₂may be a group represented by Formula 2-3:

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Z₃₁, Z₃₂, d4, and d5 in Formula 2-3 are the same as described in the present specification, and * indicates a binding site to a neighboring atom.

In an embodiment, at least one of R₁₀(s) in the number of b10, R₂₀(s) in the number of b20, or any combination thereof may be a substituted or unsubstituted C₄-C₆₀alkyl group or a substituted or unsubstituted C₆-C₆₀aryl group.

In an embodiment, at least one of Ar₁, Ar₂, or a combination thereof may be a biphenyl group or a terphenyl group, each substituted with at least one C₄-C₂₀alkyl group.

In an embodiment, the condensed cyclic compound may be represented by Formula 1-A:

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In Formula 1-A,

X₁to X₄may each independently be N or C(R₁₀), X₅to X₈may each independently be N or C(R₂₀), and

L₁, a1, Ar₁, Ar₂, R₁to R₄, R₁₀, R₂₀, and b1 to b4 are the same as described above.

For example, at least one of X₁to X₄may be C(R₁₀), and R₁₀may be a substituted or unsubstituted C₄-C₆₀alkyl group, or a substituted or unsubstituted C₆-C₆₀aryl group.

For example, X₃may be C(R₁₀), and R₁₀may be a substituted or unsubstituted C₄-C₆₀alkyl group, or a substituted or unsubstituted C₆-C₆₀aryl group.

For example, at least one of X₅to X₈may be C(R₁₀), and R₁₀may be a substituted or unsubstituted C₄-C₆₀alkyl group, or a substituted or unsubstituted C₆-C₆₀aryl group.

For example, X₇may be C(R₁₀), and R₁₀may be a substituted or unsubstituted C₄-C₆₀alkyl group, or a substituted or unsubstituted C₆-C₆₀aryl group.

Description of FIG. 1

FIG. 1 is a schematic view of an organic light-emitting device 10 according to an exemplary embodiment. Hereinafter, a structure and a manufacturing method of an organic light-emitting device according to an example of the present disclosure will be described with reference to FIG. 1.

The organic light-emitting device 10 of FIG. 1 includes a first electrode 11, a second electrode 19 facing the first electrode 11, and an organic layer 10A between the first electrode 11 and the second electrode 19.

The organic layer 10A includes an emission layer 15, a hole transport region 12 located between the first electrode 11 and the emission layer 15, and an electron transport region 17 located between the emission layer 15 and the second electrode 19.

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

First Electrode 11

In one or more embodiments, the first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be a material with a high work function to facilitate hole injection.

The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 11 is a transmissive electrode, a material for forming a first electrode may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), or any combination thereof, but embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combination thereof, but embodiments of the present disclosure are not limited thereto.

The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers.

Emission Layer 15

An emission layer 15 may include the condensed cyclic compound.

In this regard, the emission layer 15 may further include a host, and the condensed cyclic compound may be a dopant.

For example, the condensed cyclic compound may be a fluorescent dopant.

A fluorescent dopant (e.g., a blue fluorescent dopant) in the emission layer 15 may be a hole trapping material, but the hole movement in the emission layer may not be smooth because of the fluorescent dopant. However, embodiments of the present disclosure are not limited thereto. As a result, I) the driving voltage of the organic light-emitting device may increase, ii) the emission efficiency of the organic light-emitting device may be reduced due to the triplet-polaron-quenching (TPQ), which arises when excess holes and/or electrons left unrecombined in the emission layer and triplet excitons in the emission layer are linked, and iii) the lifespan of the organic light-emitting device may be reduced as the bond of the emission layer material molecules is broken by the energy generated by the TQP.

However, since the condensed cyclic compound in the emission layer is represented by Formula 1, hole traps may be reduced. As a result, hole injection characteristics into the emission layer (e.g., hole injection characteristics at low gradations of 100 nit or less, 50 nit or less, or 1 mA/cm²or less) may be improved and the charge imbalance between holes and electrons in the emission layer may substantially be prevented. As a result, triplet-triplet fusion (TTF) generation efficiency in the emission layer may increase, thereby increasing the emission efficiency of an organic light-emitting device including the emission layer, and improving driving voltage and dark area expression power (e.g., dark area expression power in low gradations of 100 nit or less, 50 nit or less, 1 mA/cm²or less, in which the electric field is weak).

According to an embodiment, the lowest triple energy level (T₁) of the host may be at least 2.0 eV.

T₁is measured using the Density Functional Theory (DFT).

The term “DFT was used” as used herein may indicate based on the 6-311+G(d,p) basis set, a quantum chemical calculation method according to the DFT was used. The quantum chemical calculation method can use, for example, the Gaussian 09 program.

The ratio of the fluorescent luminescent component emitted from the fluorescent dopant among the entire fluorescent luminescent component emitted from the emission layer 15 may be about 50% or more, about 60% or more, about 70% or more, about 80% or more or about 90% or more. That is, the fluorescent luminescent component from the emission layer 15 may be a fluorescent luminescent component emitted from the fluorescent dopant.

The emission layer 15 may further include a first compound and a second compound, and the first compound may satisfy one of Condition 1 and Condition 2, and the second compound may be different from the first compound and the condensed cyclic compound:

Condition 1

The first compound includes a transition metal.

Condition 2

The difference between the triplet energy level of the first compound and the singlet energy level of the first compound is about 0.3 eV or less, and the first compound may emit delayed fluorescence.

The description of the first compound, the second compound, and the condensed cyclic compound are each the same as described in the present specification.

The first compound, the second compound, and the condensed cyclic compound included in the emission layer 15 are different from each other. That is, the emission layer 15 may include three or more compounds different from each other.

In an embodiment, the emission layer 15 may include a sensitizer, a dopant, and a host, the sensitizer may include a first compound, the dopant may include a condensed cyclic compound, and the host may include a third compound.

The emission layer 15 may emit fluorescence. That is, the dopant may be a material that may emit fluorescence. The emission layer 15, which emits the fluorescent light, is clearly distinguished from an emission layer of the related art that emits phosphorescent light.

In general, it is known that since triplet excitons remain for an extended period of time in an excited state, they influence the decrease in the lifespan of organic light-emitting devices. However, according to the present disclosure, the dopant is used to reduce the time during which the triplet excitons of the sensitizer remain in the excited state. Accordingly, an organic light-emitting device including the dopant may have a prolonged lifespan.

In an embodiment, the more triplet excitons the sensitizer has, the more excess energy is accumulated in the sensitizer, resulting in more hot excitons. That is, the amount of triplet excitons of the sensitizer is proportional to the number of hot excitons. The hot excitons break down various chemical bonds of a compound included in an emission layer and/or a compound existing at the interface of the emission layer and other layers to decompose the compound. Accordingly, the lifespan of organic light-emitting devices may be reduced. However, according to the present disclosure, by using dopants, the triplet excitons of the sensitizer can be quickly converted to singlet excitons of the dopant, ultimately reducing the number of hot excitons and increasing the lifespan of an organic light-emitting device.

In this regard, “hot excitons” may be generated or increased by exciton-exciton annihilation due to an increase in the density of excitons in an emission layer 15, exciton-charge annihilation due to the charge imbalance in an emission layer 15, and/or radical ion pairs due to the delivery of electrons between a host and dopant.

Further, the dopant emits fluorescence, and accordingly, an organic light-emitting device having high color purity may be provided, and particularly, a singlet exciton in an excited state in the dopant rapidly transitions to a ground state at room temperature, the accumulation of singlet excitons in an excited state in the dopant may be prevented, and the lifespan of the light-emitting device may be improved.

Particularly, singlet and triplet excitons are formed at the host in the emission layer 15, and the singlet and triplet excitons formed at the host are transferred to the sensitizer and then to the dopant through the Förster energy transfer (FRET). In this regard, in order to embody the high efficiency and long lifespan of the organic light-emitting device, it is necessary to control the hot excitons generated in the emission layer, which requires optimization of energy transfer.

Particularly, when the sensitizer is a thermally activated delayed fluorescence (TADF) emitter which satisfies ΔE_ST≤0.3 eV, singlet excitons formed in the host in a proportion of 25% are delivered to the sensitizer through the FRET, and the energy of the triplet excitons formed in the host in a proportion of 75% is transitioned to the singlet and the triplet of the sensitizer, and the energy transferred to the triplet undergoes reverse intersystem crossing (RISC) to be a singlet, and then the singlet energy of the sensitizer is transitioned to the dopant through the FRET.

More particularly, if the sensitizer is an organometallic compound including at least one metal of a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, and a third-row transition metal of the Periodic Table of Elements, the triplet excitons formed in the host at a proportion of 75% may be transferred to the sensitizer through Dexter energy transfer, the energy of the singlet excitons formed in the host at a proportion of 25% may be transitioned to the singlet and the triplet of the sensitizer, the energy transferred to the singlet undergoes intersystem crossing (ISC) to a triplet, and then the triplet energy of the sensitizer is transitioned to the dopant through the FRET.

Accordingly, by transferring all the singlet excitons and triplet excitons generated in the host of the emission layer 15 to the dopant, an organic light-emitting device having improved efficiency can be obtained. In addition, since an organic light-emitting device can be obtained with significantly reduced energy loss, the lifespan characteristics of the organic light-emitting device can be improved.

The amount of the sensitizer in the emission layer 15 may be from about 5 wt % to about 50 wt %. Within these ranges, it is possible to achieve effective energy transfer in the emission layer 15, and accordingly, an organic light-emitting device having high efficiency and long lifespan can be obtained.

The emission layer 15 may consist of the host, the dopant, and the sensitizer. That is, the emission layer 15 may not further include materials other than the host, the dopant, and the sensitizer.

A thickness of the emission layer 15 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 15 is within these ranges, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.

Host in Emission Layer 15

The host may include an at least one second compound.

The second compound may include a bipolar compound, an electron transport compound, and/or a hole transport compound,

the electron transport compound may include at least one electron transport moiety,

the hole transport compound may not include an electron transport moiety, and

the electron transport moiety may include a cyano group, a π electron-deficient nitrogen-containing cyclic group, or a group represented by one of the following Formulae:

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In the above Formulae, *, *′, and *″ are each a binding site to a neighboring atom.

In an embodiment, the electron transport compound may include at least one π electron-deficient nitrogen-free cyclic group and at least one electron transport moiety,

the hole transport compound may include at least one π electron-deficient nitrogen-free cyclic group and may not include an electron transport moiety, and

the electron transport moiety may be a cyano group or π electron-deficient nitrogen-containing cyclic group.

For example, the π electron-deficient nitrogen-containing cyclic group may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, a benzoisoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; or a condensed cyclic group in which the two or more π electron-deficient nitrogen-containing cyclic groups are condensed with each other, or

the π electron-deficient nitrogen-free cyclic group may be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a triindolobenzene group; or a condensed cyclic group in which two or more π electron-deficient nitrogen-free cyclic groups are condensed with each other.

For example, the electron transport compound may include i) at least one of a cyano group, a pyrimidine group, a pyrazine group, a triazine group, or any combination thereof, or ii) a triphenylene group, and

the hole transport compound may include a carbazole group.

The second compound is the same as described in connection with the host to be described later.

The host may include no metal atoms.

In one or more embodiments, the host may include one kind of host. When the host includes one host, the one host may be a bipolar host, an electron transport host, or a hole transport host, which will be described later.

In one or more embodiments, the host may include a mixture of two or more different hosts. For example, the host may be a mixture of an electron transport host and a hole transport host, a mixture of two types of electron transport hosts different from each other, or a mixture of two types of hole transport hosts different from each other. The electron transport host and the hole transport host may be understood by referring to the related description to be presented later.

In an embodiment, the host may include an electron transport compound including at least one electron transport moiety, a hole transport compound that is free of an electron transport moiety, or any combination thereof.

In an embodiment, the electron transport compound in the emission layer 15 may include at least one of a cyano group, a π electron-deficient nitrogen-containing cyclic group, or any combination thereof.

In an embodiment, the electron transport compound in the emission layer 15 may include at least one cyano group.

In an embodiment, the electron transport compound in the emission layer 15 may include at least one cyano group and at least one π electron deficient nitrogen-containing cyclic group.

In an embodiment, the electron transport compound may be a compound represented by Formula E-1, and

the hole transport compound may be a compound represented by Formula H-1, but embodiments of the present disclosure are not limited thereto:

[Ar301]xb11-[(L301)xb1-R301]xb21 <Formula E-1>

wherein, in Formula E-1,

Ar₃₀₁may be a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group, and

xb11 may be 1, 2, or 3,

L₃₀₁may each independently be a single bond, a group represented by the one of the following formulae, a substituted or unsubstituted C₅-C₆₀carbocyclic group, or a substituted or unsubstituted C₁-C₆₀heterocyclic group, and *, *′ and *″ in the following formulae are each a binding site to a neighboring atom,

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xb1 may be an integer from 1 to 5,

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

xb21 may be an integer from 1 to 5,

Q₃₀₁to Q₃₀₃are each independently be a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and at least one of Condition A to Condition C may be satisfied.

Condition A

Ar₃₀₁, L₃₀₁, and R₃₀₁in Formula E-1 may each independently include a π electron-deficient nitrogen-containing cyclic group.

Condition B

L₃₀₁in Formula E-1 is a group represented by one of the following groups:

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Condition C

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

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

L₄₀₁may be:

a single bond; or

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

xd1 may be an integer from 1 to 10, wherein when xd1 is 2 or more, two or more of L₄₀₁(s) may be identical to or different from each other,

Ar₄₀₁may be a group represented by Formulae 11 or 12,

Ar₄₀₂may be a group represented by Formula 11 or 12, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group; or

a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group, each substituted with at least one deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, or any combination thereof,

CY₄₀₁and CY₄₀₂may each independently be a benzene group, a naphthalene group, a fluorene group, a carbazole group, a benzocarbazole group, an indolocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a benzonaphthofuran group, a benzonaphthothiophene group, or a benzonaphthosilole group,

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

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

at least one of A₂₁, A₂₂, or any combination thereof in Formula 12 is not a single bond,

R₅₁to R₅₄, R₆₀, and R₇₀may each independently be:

hydrogen, deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, or a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group or a C₁-C₂₀alkoxy group, each substituted with at least one deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof;

a π electron-deficient nitrogen-free cyclic group (for example, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, and a triphenylenyl group), each substituted with at least one deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a biphenyl group; or

—Si(Q₄₀₄)(Q₄₀₅)(Q₄₀₆),

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

Q₄₀₁to Q₄₀₆may each independently be hydrogen, deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group, or

* indicates a binding site to an adjacent atom.

In one or more embodiments, Ar₃₀₁and L₃₀₁in Formula E-1 may each independently be a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof,

at least one of L₃₀₁(s) in the number of xb1 may each independently be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano group-containing phenyl group, a cyano group-containing biphenyl group, a cyano group-containing terphenyl group, a cyano group-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof, and

R₃₀₁may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing quaterphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁to Q₃₃may each independently be a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, but embodiments of the present disclosure are not limited thereto.

In one or more embodiments,

A₃₀₁may be a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof; or

a group represented by one of Formulae 5-1 to 5-3 and Formulae 6-1 to 6-33, and

L₃₀₁may be a group represented by Formulae 5-1 to 5-3 and Formulae 6-1 to 6-33:

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wherein, in Formulae 5-1 to 5-3 and 6-1 to 6-33,

Z₁may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂),

d4 may be 0, 1, 2, 3, or 4,

d3 may be 0, 1, 2, or 3,

d2 may be 0, 1, or 2, and

* and *¹each indicate a binding site to a neighboring atom.

wherein Q₃₁to Q₃₃are the same as described above.

In one or more embodiments, L₃₀₁may be a group represented by Formulae 5-2, 5-3 and 6-8 to 6-33.

In one or more embodiments, R₃₀₁may be a cyano group or a group represented by one of Formula 7-1 to 7-18, and at least one of Ar₄₀₂(s) in the number of xd11 may be a group represented by one of Formulae 7-1 to 7-18, but embodiments of the present disclosure are not limited thereto:

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wherein, in Formulae 7-1 to 7-18,

xb41 to xb44 may each be 0, 1, or 2, wherein xb41 in Formula 7-10 is not 0, the sum of xb41 and xb42 in Formulae 7-11 to 7-13 is not 0, the sum of xb41, xb42, and xb43 in Formulae 7-14 to 7-16 is not 0, the sum of xb41, xb42, xb43, and xb44 in Formulae 7-17 and 7-18 is not 0, and * indicates a binding site to a neighboring atom.

Two or more Ar₃₀₁(s) in Formula E-1 may be identical to or different from each other, two or more of L₃₀₁(s) in Formula E-1 may be identical to or different from each other, two or more of L₄₀₁(s) in Formula H-1 may be identical to or different from each other, and two or more of Ar₄₀₂(s) in Formula H-1 may be identical to or different from each other.

In an embodiment, the electron transport compound may include at least one cyano group.

The electron transport compound may be, for example, a group of HE1 to HE7, but embodiments of the present disclosure are not limited thereto:

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In one embodiment, the hole transport host may be one of Compounds H-H1 to H-H103, but embodiments of the present disclosure are not limited thereto:

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In an embodiment, the bipolar host may be group HEH1, but embodiments of the present disclosure are not limited thereto:

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wherein, in Compounds 1 to 432, Ph is a phenyl group.

When the host is a mixture of an electron transport host and a hole transport host, the weight ratio of the electron transport host to the hole transport host may be 1:9 to 9:1, for example, 2:8 to 8:2, for example, 4:6 to 6:4, for example, 5:5. When the weight ratio of the electron transport host and the hole transport host satisfies the above-described ranges, the hole-and-electron transport balance in the emission layer 15 may be achieved.

Dopant in Emission Layer 15

The dopant may include a condensed cyclic compound.

Since the dopant emits fluorescent light, organic light-emitting devices according to an embodiment of the present disclosure are clearly distinguished from organic light-emitting devices containing compounds that emit phosphorescent light.

In an embodiment, the dopant may be free of metal atoms.

In an embodiment, the dopant may further include a condensed polycyclic compound, a styryl compound, or a combination thereof, in addition to the condensed cyclic compound.

For example, the dopant may include one of a naphthalene-containing core, a fluorene-containing core, a spiro-bifluorene-containing core, a benzofluorene-containing core, a dibenzofluorene-containing core, a phenanthrene-containing core, an anthracene-containing core, a fluoranthene-containing core, a triphenylene-containing core, a pyrene-containing core, a chrysene-containing core, a naphthacene-containing core, a picene-containing core, a perylene-containing core, a pentaphene-containing core, an indenoanthracene-containing core, a tetracene-containing core, a bisanthracene-containing core, or a core represented by one of Formulae 501-1 to 501-18, but embodiments of the present disclosure are not limited thereto:

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In one or more embodiments, the dopant may be a styryl-amine-based compound or a styryl-carbazole-based compound, but embodiments of the present disclosure are not limited thereto.

In one embodiment, the dopant may be compounds represented by Formula 501:

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wherein, in Formula 501,

Ar₅₀₁may be:

a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene 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 indenoanthracene group, a tetracene group, a bisanthracene group, or a group represented by one of Formulae 501-1 to 501-18, each substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-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(Q₅₀₁)(Q₅₀₂)(Q₅₀₃) (wherein Q₅₀₁to Q₅₀₃may each independently be hydrogen, C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a C₆-C₆₀aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group), or any combination thereof,

L₅₀₁to L₅₀₃may each independently be a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted heterocycloalkenylene 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, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

R₅₀₁and R₅₀₂may each independently be:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl 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, a dibenzofuranyl group, or a dibenzothiophenyl group, each substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, 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-bifluorenyl 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, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof,

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

xd4 may be 0, 1, 2, 3, 4, 5, or 6.

For example, in Formula 501,

Ar₅₀₁may be:

a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a tetracene group, a bisanthracene group, or a group represented by one of Formula 501-1 to 501-18, each substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, —Si(Q₅₀₁)(Q₅₀₂)(Q₅₀₃) (Q₅₀₁to Q₅₀₃may each independently be hydrogen, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group), or any combination thereof,

L₅₀₁to L₅₀₃are the same as described in connection with L₂₀₁to L₂₀₉,

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

xd4 may be 0, 1, 2, or 3, but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, the dopant may include a compound represented by one of Formulae 502-1 to 502-5:

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wherein, in Formulae 502-1 to 502-5,

X₅₁may be N or C-[(L₅₀₁)_xd1-R₅₀₁], X₅₂may be N or C-[(L₅₀₂)_xd2-R₅₀₂], X₅₃may be N or C-[(L₅₀₃)_xd3-R₅₀₃], X₅₄may be N or C-[(L₅₀₄)_xd4-R₅₀₄], X₅₅may be N or C-[(L₅₀₅)_xd5-R₅₀₅], X₅₆may be N or C-[(L₅₀₆)_xd6-R₅₀₆], X₅₇may be N or C-[(L₅₀₇)_xd7-R₅₀₇], and X₅₈may be N or C-[(L₅₀₈)_xd8-R₅₀₈],

L₅₀₁to L₅₀₈are each the same as described in connection with L₅₀₁in Formula 501,

xd1 to xd8 are each the same as described in connection with xd1 in Formula 501,

R₅₀₁to R₅₀₈may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group,

xd11 and xd12 may each independently be an integer from 0 to 5, and

two of R₅₀₁to R₅₀₄may optionally be linked together to form a saturated or unsaturated ring, and

two of R₅₀₅to R₅₀₈may optionally be linked together to form a saturated or unsaturated ring.

The dopant may include at least one compound of, for example, Compounds FD(1) to FD(16) and Group F-1:

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The amount of the dopant in the emission layer may be about 0.01 wt % to about 15 wt %, but embodiments of the present disclosure are not limited thereto.

Sensitizer in Emission Layer 15

The sensitizer may include a first compound.

In an embodiment, the first compound may satisfy Condition 1.

For example, the first compound may include an organometallic compound represented by Formula 101:

M₁₁(L₁₁)_n11(L₁₂)_n12. Formula 101

In Formula 101,

M₁₁may be a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, or a third-row transition metal of the Periodic Table of Elements,

L₁₁may be a ligand represented by one of Formulae 101-1 to 101-4,

L₁₂may be a monodentate ligand or a bidentate ligand;

n11 may be 1,

n12 may be 0, 1, and 2,

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wherein, in Formula 101-1 to 101-4,

A₁₀₁to A₁₀₄may each independently be a substituted or unsubstituted C₅-C₃₀carbocyclic group, a substituted or unsubstituted C₁-C₃₀heterocyclic group, or a non-cyclic group,

Y₁₀₁to Y₁₀₄may each independently be a chemical bond, O, S, N(R₉₁), B(R₉₁), P(R₉₁), or C(R₉₁)(R₉₂),

T₁₀₁to T₁₀₄may each independently be a single bond, a double bond, *—N(R₉₃)—*′, *—B(R₉₃)—*′, *—P(R₉₃)—*′, *—C(R₉₃)(R₉₄)—*′, *—Si(R₉₃)(R₉₄)—*′, *—Ge(R₉₃)(R₉₄)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*′, *—C(R₉₃)═*′, *═C(R₉₃)—*′, *—C(R₉₃)═C(R₉₄)—*′, *—C(═S)—*′, or *—C≡C—*′,

a substituent of the substituted C₅-C₃₀carbocyclic group, a substituent of the substituted C₁-C₃₀heterocyclic group, and R₉₁to R₉₄may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(═O)(Q₄₁), —S(═O)(Q₄₁), —S(═O)₂(Q₄₁), —N(Q₄₂)(Q₄₃), —B(Q₄₂)(Q₄₃), —Si(Q₄₄)(Q₄₅)(Q₄₆), —Ge(Q₄₄)(Q₄₅)(Q₄₆), —P(═O)(Q₄₇)(Q₄₈), —P(═S)(Q₄₇)(Q₄₈), or —P(Q₄₇)(Q₄₈), wherein each of the substituent of the substituted C₅-C₃₀carbocyclic group and the substituent of the substituted C₁-C₃₀heterocyclic group is not hydrogen,

*₁, *₂, *₃, and *₄each indicate a binding site to M₁₁, and

Q₄₁to Q₄₈may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₇-C₆₀alkylaryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀alkyl heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C₁-C₆₀alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryl group that is substituted with one or more of deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or a combination thereof.

In an embodiment, the first compound may satisfy Condition 2.

For example, the first compound may include a thermally activated delayed fluorescence emitter represented by any one of Formula 201 or 202:

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In Formula 201,

X₂₀₁to X₂₀₃may each independently be B or N,

A₂₀₁to A₂₀₅may each independently be a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

L₂₀₁to L₂₀₅may each independently be a single bond, a C₅-C₃₀carbocyclic group unsubstituted or substituted with at least one R_200a, or a C₁-C₃₀heterocyclic group unsubstituted or substituted with at least one R_200a,

a201 to a205 may each independently be an integer from 1 to 5,

R₂₀₁to R₂₀₅, and R_200amay each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₅₁)(Q₅₂), —Si(Q₅₃)(Q₅₄)(Q₅₅), —Ge(Q₅₃)(Q₅₄)(Q₅₅), —B(Q₅₆)(Q₅₇), —P(═O)(Q₅₈)(Q₅₉), or —P(Q₅₈)(Q₅₉),

b201 to b205 may each independently be 0 to 10, when b201 is 2 or more, two or more of R₂₀₁(s) may be identical to or different from each other, when b202 is 2 or more, two or more of R₂₀₂(s) may be identical to or different from each other, when b203 is 2 or more, two or more of R₂₀₃(s) may be identical to or different from each other, when b204 is 2 or more, two or more of R₂₀₄(s) may be identical to or different from each other, and when b205 is 2 or more, two or more of R₂₀₅(s) may be identical to or different from each other,

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A₂₁₁may be a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

W₂₁₁may be an acceptor group,

D₂₁₁may be a donor group,

m211 may be an integer from 1 to 4, n211 may be an integer from 1 to 4,

R₂₁₁may be hydrogen, deuterium, —F, —Cl, —Br, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₅₁)(Q₅₂), —Si(Q₅₃)(Q₅₄)(Q₅₅), —Ge(Q₅₃)(Q₅₄)(Q₅₅), —B(Q₅₆)(Q₅₇), —P(═O)(Q₅₈)(Q₅₉), or —P(Q₅₈)(Q₅₉), wherein a plurality of R₂₁₁are optionally linked to each other to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

a substituent of the substituted C₅-C₃₀carbocyclic group, substituted C₁-C₃₀heterocyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:

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

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, or C₁-C₆₀alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₆₁)(Q₆₂), —Si(Q₆₃)(Q₆₄)(Q₆₅), —Ge(Q₆₃)(Q₆₄)(Q₆₅), —B(Q₆₆)(Q₆₇), —P(═O)(Q₆₈)(Q₆₉), —P(Q₆₈)(Q₆₉), or any combination thereof;

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₇₁)(Q₇₂), —Si(Q₇₃)(Q₇₄)(Q₇₅), —Ge(Q₇₃)(Q₇₄)(Q₇₅), —B(Q₇₆)(Q₇₇), —P(═O)(Q₇₈)(Q₇₉), —P(Q₇₈)(Q₇₉), or any combination thereof;

—N(Q₈₁)(Q₈₂), —Si(Q₈₃)(Q₈₄)(Q₈₅), —Ge(Q₈₃)(Q₈₄)(Q₈₅), —B(Q₈₆)(Q₈₇), —P(═O)(Q₈₈)(Q₈₉) or —P(Q₈₈)(Q₈₉); or

any combination thereof,

wherein Q₅₁to Q₅₉, Q₆₁to Q₆₉, Q₇₁to Q₇₉, and Q₈₁to Q₈₉may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid or a salt thereof; a sulfonic acid or a salt thereof; a phosphoric acid or a salt thereof; a C₁-C₆₀alkyl group which is unsubstituted or substituted with deuterium, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or any combination thereof; a C₂-C₆₀alkenyl group; a C₂-C₆₀alkynyl group; a alkoxy group; a C₃-C₁₀cycloalkyl group; a C₁-C₁₀heterocycloalkyl group; a C₃-C₁₀cycloalkenyl group; a C₁-C₁₀heterocycloalkenyl group; a C₆-C₆₀aryl group which is unsubstituted or substituted with deuterium, a C₁-C₆₀alkyl group, a C₆-C₆₀aryl group, or any combination thereof; a C₆-C₆₀aryloxy group; a C₆-C₆₀arylthio group; a C₁-C₆₀heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

For example, W₂₁₁may be a substituted or unsubstituted π electron-deficient nitrogen-free cyclic group;

D₂₁₁may be —F, a cyano group, or a π electron-deficient nitrogen-containing cyclic group;

a C₁-C₆₀alkyl group, an π electron-deficient nitrogen-containing cyclic group, or an π electron-deficient nitrogen-free cyclic group, each substituted with at least one —F, a cyano group, or a combination thereof; or

a π electron-deficient nitrogen-containing cyclic group substituted with at least one deuterium, a C₁-C₆₀alkyl group, a π electron-deficient nitrogen-containing cyclic group, a π electron-deficient nitrogen-free cyclic group, or any combination thereof,

The term “π electron-deficient nitrogen-containing cyclic group” used herein refers to a cyclic group having at least one *—N=*′ moiety, and, for example, may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, a benzimidazolobenzimidazole group, or a condensed cyclic group in which two or more π electron-efficient nitrogen-containing cyclic groups are condensed with each other.

In an embodiment, the sensitizer may be a compound of Groups I to VI, but embodiments of the present disclosure are not limited thereto.

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Group V

In an embodiment, the sensitizer may be a compound represented by Formula A below.

(L₁₀₁)_n101-M₁₀₁-(L₁₀₂)_m101 Formula A

L₁₀₁, n101, M₁₀₁, L₁₀₂, and m101 in Formula A are the same as described in connection with Tables 1 to 3:

TABLE 1

Compound

name
L₁₀₁
n101
M₁₀₁
L₁₀₂
m101

BD001
LM1
3
Ir
—
0

BD002
LM2
3
Ir
—
0

BD003
LM3
3
Ir
—
0

BD004
LM4
3
Ir
—
0

BD005
LM5
3
Ir
—
0

BD006
LM6
3
Ir
—
0

BD007
LM7
3
Ir
—
0

BD008
LM8
3
Ir
—
0

BD009
LM9
3
Ir
—
0

BD010
LM10
3
Ir
—
0

BD011
LM11
3
Ir
—
0

BD012
LM12
3
Ir
—
0

BD013
LM13
3
Ir
—
0

BD014
LM14
3
Ir
—
0

BD015
LM15
3
Ir
—
0

BD016
LM16
3
Ir
—
0

BD017
LM17
3
Ir
—
0

BD018
LM18
3
Ir
—
0

BD019
LM19
3
Ir
—
0

BD020
LM20
3
Ir
—
0

BD021
LM21
3
Ir
—
0

BD022
LM22
3
Ir
—
0

BD023
LM23
3
Ir
—
0

BD024
LM24
3
Ir
—
0

BD025
LM25
3
Ir
—
0

BD026
LM26
3
Ir
—
0

BD027
LM27
3
Ir
—
0

BD028
LM28
3
Ir
—
0

BD029
LM29
3
Ir
—
0

BD030
LM30
3
Ir
—
0

BD031
LM31
3
Ir
—
0

BD032
LM32
3
Ir
—
0

BD033
LM33
3
Ir
—
0

BD034
LM34
3
Ir
—
0

BD035
LM35
3
Ir
—
0

BD036
LM36
3
Ir
—
0

BD037
LM37
3
Ir
—
0

BD038
LM38
3
Ir
—
0

BD039
LM39
3
Ir
—
0

BD040
LM40
3
Ir
—
0

BD041
LM41
3
Ir
—
0

BD042
LM42
3
Ir
—
0

BD043
LM43
3
Ir
—
0

BD044
LM44
3
Ir
—
0

BD045
LM45
3
Ir
—
0

BD046
LM46
3
Ir
—
0

BD047
LM47
3
Ir
—
0

BD048
LM48
3
Ir
—
0

BD049
LM49
3
Ir
—
0

BD050
LM50
3
Ir
—
0

BD051
LM51
3
Ir
—
0

BD052
LM52
3
Ir
—
0

BD053
LM53
3
Ir
—
0

BD054
LM54
3
Ir
—
0

BD055
LM55
3
Ir
—
0

BD056
LM56
3
Ir
—
0

BD057
LM57
3
Ir
—
0

BD058
LM58
3
Ir
—
0

BD059
LM59
3
Ir
—
0

BD060
LM60
3
Ir
—
0

BD061
LM61
3
Ir
—
0

BD062
LM62
3
Ir
—
0

BD063
LM63
3
Ir
—
0

BD064
LM64
3
Ir
—
0

BD065
LM65
3
Ir
—
0

BD066
LM66
3
Ir
—
0

BD067
LM67
3
Ir
—
0

BD068
LM68
3
Ir
—
0

BD069
LM69
3
Ir
—
0

BD070
LM70
3
Ir
—
0

BD071
LM71
3
Ir
—
0

BD072
LM72
3
Ir
—
0

BD073
LM73
3
Ir
—
0

BD074
LM74
3
Ir
—
0

BD075
LM75
3
Ir
—
0

BD076
LM76
3
Ir
—
0

BD077
LM77
3
Ir
—
0

BD078
LM78
3
Ir
—
0

BD079
LM79
3
Ir
—
0

BD080
LM80
3
Ir
—
0

BD081
LM81
3
Ir
—
0

BD082
LM82
3
Ir
—
0

BD083
LM83
3
Ir
—
0

BD084
LM84
3
Ir
—
0

BD085
LM85
3
Ir
—
0

BD086
LM86
3
Ir
—
0

BD087
LM87
3
Ir
—
0

BD088
LM88
3
Ir
—
0

BD089
LM89
3
Ir
—
0

BD090
LM90
3
Ir
—
0

BD091
LM91
3
Ir
—
0

BD092
LM92
3
Ir
—
0

BD093
LM93
3
Ir
—
0

BD094
LM94
3
Ir
—
0

BD095
LM95
3
Ir
—
0

BD096
LM96
3
Ir
—
0

BD097
LM97
3
Ir
—
0

BD098
LM98
3
Ir
—
0

BD099
LM99
3
Ir
—
0

BD100
LM100
3
Ir
—
0

TABLE 2

Compound

name
L₁₀₁
n101
M₁₀₁
L₁₀₂
m101

BD101
LM101
3
Ir
—
0

BD102
LM102
3
Ir
—
0

BD103
LM103
3
Ir
—
0

BD104
LM104
3
Ir
—
0

BD105
LM105
3
Ir
—
0

BD106
LM106
3
Ir
—
0

BD107
LM107
3
Ir
—
0

BD108
LM108
3
Ir
—
0

BD109
LM109
3
Ir
—
0

BD110
LM110
3
Ir
—
0

BD111
LM111
3
Ir
—
0

BD112
LM112
3
Ir
—
0

BD113
LM113
3
Ir
—
0

BD114
LM114
3
Ir
—
0

BD115
LM115
3
Ir
—
0

BD116
LM116
3
Ir
—
0

BD117
LM117
3
Ir
—
0

BD118
LM118
3
Ir
—
0

BD119
LM119
3
Ir
—
0

BD120
LM120
3
Ir
—
0

BD121
LM121
3
Ir
—
0

BD122
LM122
3
Ir
—
0

BD123
LM123
3
Ir
—
0

BD124
LM124
3
Ir
—
0

BD125
LM125
3
Ir
—
0

BD126
LM126
3
Ir
—
0

BD127
LM127
3
Ir
—
0

BD128
LM128
3
Ir
—
0

BD129
LM129
3
Ir
—
0

BD130
LM130
3
Ir
—
0

BD131
LM131
3
Ir
—
0

BD132
LM132
3
Ir
—
0

BD133
LM133
3
Ir
—
0

BD134
LM134
3
Ir
—
0

BD135
LM135
3
Ir
—
0

BD136
LM136
3
Ir
—
0

BD137
LM137
3
Ir
—
0

BD138
LM138
3
Ir
—
0

BD139
LM139
3
Ir
—
0

BD140
LM140
3
Ir
—
0

BD141
LM141
3
Ir
—
0

BD142
LM142
3
Ir
—
0

BD143
LM143
3
Ir
—
0

BD144
LM144
3
Ir
—
0

BD145
LM145
3
Ir
—
0

BD146
LM146
3
Ir
—
0

BD147
LM147
3
Ir
—
0

BD148
LM148
3
Ir
—
0

BD149
LM149
3
Ir
—
0

BD150
LM150
3
Ir
—
0

BD151
LM151
3
Ir
—
0

BD152
LM152
3
Ir
—
0

BD153
LM153
3
Ir
—
0

BD154
LM154
3
Ir
—
0

BD155
LM155
3
Ir
—
0

BD156
LM156
3
Ir
—
0

BD157
LM157
3
Ir
—
0

BD158
LM158
3
Ir
—
0

BD159
LM159
3
Ir
—
0

BD160
LM160
3
Ir
—
0

BD161
LM161
3
Ir
—
0

BD162
LM162
3
Ir
—
0

BD163
LM163
3
Ir
—
0

BD164
LM164
3
Ir
—
0

BD165
LM165
3
Ir
—
0

BD166
LM166
3
Ir
—
0

BD167
LM167
3
Ir
—
0

BD168
LM168
3
Ir
—
0

BD169
LM169
3
Ir
—
0

BD170
LM170
3
Ir
—
0

BD171
LM171
3
Ir
—
0

BD172
LM172
3
Ir
—
0

BD173
LM173
3
Ir
—
0

BD174
LM174
3
Ir
—
0

BD175
LM175
3
Ir
—
0

BD176
LM176
3
Ir
—
0

BD177
LM177
3
Ir
—
0

BD178
LM178
3
Ir
—
0

BD179
LM179
3
Ir
—
0

BD180
LM180
3
Ir
—
0

BD181
LM181
3
Ir
—
0

BD182
LM182
3
Ir
—
0

BD183
LM183
3
Ir
—
0

BD184
LM184
3
Ir
—
0

BD185
LM185
3
Ir
—
0

BD186
LM186
3
Ir
—
0

BD187
LM187
3
Ir
—
0

BD188
LM188
3
Ir
—
0

BD189
LM189
3
Ir
—
0

BD190
LM190
3
Ir
—
0

BD191
LM191
3
Ir
—
0

BD192
LM192
3
Ir
—
0

BD193
LM193
3
Ir
—
0

BD194
LM194
3
Ir
—
0

BD195
LM195
3
Ir
—
0

BD196
LM196
3
Ir
—
0

BD197
LM197
3
Ir
—
0

BD198
LM198
3
Ir
—
0

BD199
LM199
3
Ir
—
0

BD200
LM200
3
Ir
—
0

TABLE 3

Compound

name
L₁₀₁
n101
M₁₀₁
L₁₀₂
m101

BD201
LM201
3
Ir
—
—

BD202
LM202
3
Ir
—
—

BD203
LM203
3
Ir
—
—

BD204
LM204
3
Ir
—
—

BD205
LM205
3
Ir
—
—

BD206
LM206
3
Ir
—
—

BD207
LM207
3
Ir
—
—

BD208
LM208
3
Ir
—
—

BD209
LM209
3
Ir
—
—

BD210
LM210
3
Ir
—
—

BD211
LM211
3
Ir
—
—

BD212
LM212
3
Ir
—
—

BD213
LM213
3
Ir
—
—

BD214
LM214
3
Ir
—
—

BD215
LM215
3
Ir
—
—

BD216
LM216
3
Ir
—
—

BD217
LM217
3
Ir
—
—

BD218
LM218
3
Ir
—
—

BD219
LM219
3
Ir
—
—

BD220
LM220
3
Ir
—
—

BD221
LM221
3
Ir
—
—

BD222
LM222
3
Ir
—
—

BD223
LM223
3
Ir
—
—

BD224
LM224
3
Ir
—
—

BD225
LM225
3
Ir
—
—

BD226
LM226
3
Ir
—
—

BD227
LM227
3
Ir
—
—

BD228
LM228
3
Ir
—
—

BD229
LM229
3
Ir
—
—

BD230
LM230
3
Ir
—
—

BD231
LM231
3
Ir
—
—

BD232
LM232
3
Ir
—
—

BD233
LM233
3
Ir
—
—

BD234
LM234
3
Ir
—
—

BD235
LM235
3
Ir
—
—

BD236
LM236
3
Ir
—
—

BD237
LM237
3
Ir
—
—

BD238
LM238
3
Ir
—
—

BD239
LM239
3
Ir
—
—

BD240
LM240
3
Ir
—
—

BD241
LM241
3
Ir
—
—

BD242
LM242
3
Ir
—
—

BD243
LM243
3
Ir
—
—

BD244
LFM1
3
Ir
—
—

BD245
LFM2
3
Ir
—
—

BD246
LFM3
3
Ir
—
—

BD247
LFM4
3
Ir
—
—

BD248
LFM5
3
Ir
—
—

BD249
LFM6
3
Ir
—
—

BD250
LFM7
3
Ir
—
—

BD251
LFP1
3
Ir
—
0

BD252
LFP2
3
Ir
—
0

BD253
LFP3
3
Ir
—
0

BD254
LFP4
3
Ir
—
0

BD255
LFP5
3
Ir
—
0

BD256
LFP6
3
Ir
—
0

BD257
LFP7
3
Ir
—
0

BD258
LM47
2
Ir
AN1
1

BD259
LM47
2
Ir
AN2
1

BD260
LM47
2
Ir
AN3
1

BD261
LM47
2
Ir
AN4
1

BD262
LM47
2
Ir
AN5
1

BD263
LM11
2
Pt
—
0

BD264
LM13
2
Pt
—
0

BD265
LM15
2
Pt
—
0

BD266
LM45
2
Pt
—
0

BD267
LM47
2
Pt
—
0

BD268
LM49
2
Pt
—
0

BD269
LM98
2
Pt
—
0

BD270
LM100
2
Pt
—
0

BD271
LM102
2
Pt
—
0

BD272
LM132
2
Pt
—
0

BD273
LM134
2
Pt
—
0

BD274
LM136
2
Pt
—
0

BD275
LM151
2
Pt
—
0

BD276
LM153
2
Pt
—
0

BD277
LM158
2
Pt
—
0

BD278
LM180
2
Pt
—
0

BD279
LM182
2
Pt
—
0

BD280
LM187
2
Pt
—
0

BD281
LM201
2
Pt
—
0

BD282
LM206
2
Pt
—
0

BD283
LM211
2
Pt
—
0

BD284
LM233
2
Pt
—
0

BD285
LM235
2
Pt
—
0

BD286
LM240
2
Pt
—
0

BD287
LFM5
2
Pt
—
0

BD288
LFM6
2
Pt
—
0

BD289
LFM7
2
Pt
—
0

BD290
LFP5
2
Pt
—
0

BD291
LFP6
2
Pt
—
0

BD292
LFP7
2
Pt
—
0

BD293
LM47
1
Pt
AN1
1

BD294
LM47
1
Pt
AN2
1

BD295
LM47
1
Pt
AN3
1

BD296
LM47
1
Pt
AN4
1

BD297
LM47
1
Pt
ANS
1

LM1 to LM243, LFM1 to LFM7, and LFP1 to LFP7 in Tables 1 to 3 may be understood by referring to Formulae 1-1 to 1-3 and Tables 4 to 6.

embedded image

TABLE 4

Formula 1-1

Ligand

name
R₁₁
R₁₂
R₁₃
R₁₄
R₁₅
R₁₆
R₁₇
R₁₈
R₁₉
R₂₀

LM1
X1
H
X3
H
X1
H
H
H
H
D

LM2
X1
H
X3
H
X1
H
H
H
D
H

LM3
X1
H
X3
H
X1
H
H
H
D
D

LM4
Y1
H
X3
H
Y1
H
H
H
D
D

LM5
Y2
H
X3
H
Y2
H
H
H
D
D

LM6
Y3
H
X3
H
Y3
H
H
H
D
D

LM7
Y3
D
X3
D
Y3
H
H
H
D
D

LM8
Y3
D
X3
D
Y3
D
H
H
D
D

LM9
Y3
D
X3
D
Y3
D
D
H
D
D

LM10
Y3
D
X3
D
Y3
D
D
D
D
D

LM11
Y3
D
Y11
D
Y
3D
D
D
D
D

LM12
Y3
D
Y11
D
Y3
H
X1
H
D
D

LM13
Y3
D
Y11
D
Y3
D
Y3
D
D
D

LM14
Y3
D
Y11
D
Y3
H
X4
H
D
D

LM15
Y3
D
Y11
D
Y3
D
Y12
D
D
D

LM16
X2
H
X3
H
X2
H
H
H
H
D

LM17
X2
H
X3
H
X2
H
H
H
D
H

LM18
X2
H
X3
H
X2
H
H
H
D
D

LM19
Y4
H
X3
H
Y4
H
H
H
D
D

LM20
Y5
H
X3
H
Y5
H
H
H
D
D

LM21
Y6
H
X3
H
Y6
H
H
H
D
D

LM22
Y7
H
X3
H
Y7
H
H
H
D
D

LM23
Y8
H
X3
H
Y8
H
H
H
D
D

LM24
Y9
H
X3
H
Y9
H
H
H
D
D

LM25
Y10
H
X3
H
Y10
H
H
H
D
D

LM26
Y10
D
X3
D
Y10
H
H
H
D
D

LM27
Y10
D
X3
D
Y10
D
H
H
D
D

LM28
Y10
D
X3
D
Y10
D
D
H
D
D

LM29
Y10
D
X3
D
Y10
D
D
D
D
D

LM30
Y10
D
Y11
D
Y10
D
D
D
D
D

LM31
Y10
D
Y11
D
Y10
H
X1
H
D
D

LM32
Y10
D
Y11
D
Y10
D
Y3
D
D
D

LM33
Y10
D
Y11
D
Y10
H
X4
H
D
D

LM34
Y10
D
Y11
D
Y10
D
Y12
D
D
D

LM35
X1
H
X4
H
X1
H
H
H
H
D

LM36
X1
H
X4
H
X1
H
H
H
D
H

LM37
X1
H
X4
H
X1
H
H
H
D
D

LM38
Y1
H
X4
H
Y1
H
H
H
D
D

LM39
Y2
H
X4
H
Y2
H
H
H
D
D

LM40
Y3
H
X4
H
Y3
H
H
H
D
D

LM41
Y3
D
X4
D
Y3
H
H
H
D
D

LM42
Y3
D
X4
D
Y3
D
H
H
D
D

LM43
Y3
D
X4
D
Y3
D
D
H
D
D

LM44
Y3
D
X4
D
Y3
D
D
D
D
D

LM45
Y3
D
Y12
D
Y3
D
D
D
D
D

LM46
Y3
D
Y12
D
Y3
H
X1
H
D
D

LM47
Y3
D
Y12
D
Y3
D
Y3
D
D
D

LM48
Y3
D
Y12
D
Y3
H
X4
H
D
D

LM49
Y3
D
Y12
D
Y3
D
Y12
D
D
D

LM50
X2
H
X4
H
X2
H
H
H
H
D

LM51
X2
H
X4
H
X2
H
H
H
D
H

LM52
X2
H
X4
H
X2
H
H
H
D
D

LM53
Y4
H
X4
H
Y4
H
H
H
D
D

LM54
Y5
H
X4
H
Y5
H
H
H
D
D

LM55
Y6
H
X4
H
Y6
H
H
H
D
D

LM56
Y7
H
X4
H
Y7
H
H
H
D
D

LM57
Y8
H
X4
H
Y8
H
H
H
D
D

LM58
Y9
H
X4
H
Y9
H
H
H
D
D

LM59
Y10
H
X4
H
Y10
H
H
H
D
D

LM60
Y10
D
X4
D
Y10
H
H
H
D
D

LM61
Y10
D
X4
D
Y10
D
H
H
D
D

LM62
Y10
D
X4
D
Y10
D
D
H
D
D

LM63
Y10
D
X4
D
Y10
D
D
D
D
D

LM64
Y10
D
Y12
D
Y10
D
D
D
D
D

LM65
Y10
D
Y12
D
Y10
H
X1
H
D
D

LM66
Y10
D
Y12
D
Y10
D
Y3
D
D
D

LM67
Y10
D
Y12
D
Y10
H
X4
H
D
D

LM68
Y10
D
Y12
D
Y10
D
Y12
D
D
D

LM69
X1
H
X5
H
X1
H
H
H
H
D

LM70
X1
H
X5
H
X1
H
H
H
D
H

LM71
X1
H
X5
H
X1
H
H
H
D
D

LM72
Y1
H
X5
H
Y1
H
H
H
D
D

LM73
Y2
H
X5
H
Y2
H
H
H
D
D

LM74
Y3
H
X5
H
Y3
H
H
H
D
D

LM75
Y3
D
X5
D
Y3
H
H
H
D
D

LM76
Y3
D
X5
D
Y3
D
H
H
D
D

LM77
Y3
D
X5
D
Y3
D
D
H
D
D

LM78
Y3
D
X5
D
Y3
D
D
D
D
D

LM79
Y3
D
Y13
D
Y3
D
D
D
D
D

LM80
Y3
D
Y13
D
Y3
H
X1
H
D
D

LM81
Y3
D
Y13
D
Y3
D
Y3
D
D
D

LM82
Y3
D
Y13
D
Y3
H
X4
H
D
D

LM83
Y3
D
Y13
D
Y3
D
Y12
D
D
D

LM84
X2
H
X5
H
X2
H
H
H
H
D

LM85
X2
H
X5
H
X2
H
H
H
D
H

LM86
X2
H
X5
H
X2
H
H
H
D
D

LM87
Y4
H
X5
H
Y4
H
H
H
D
D

LM88
Y5
H
X5
H
Y5
H
H
H
D
D

LM89
Y6
H
X5
H
Y6
H
H
H
D
D

LM90
Y7
H
X5
H
Y7
H
H
H
D
D

LM91
Y8
H
X5
H
Y8
H
H
H
D
D

LM92
Y9
H
X5
H
Y9
H
H
H
D
D

LM93
Y10
H
X5
H
Y10
H
H
H
D
D

LM94
Y10
D
X5
D
Y10
H
H
H
D
D

LM95
Y10
D
X5
D
Y10
D
H
H
D
D

LM96
Y10
D
X5
D
Y10
D
D
H
D
D

LM97
Y10
D
X5
D
Y10
D
D
D
D
D

LM98
Y10
D
Y13
D
Y10
D
D
D
D
D

LM99
Y10
D
Y13
D
Y10
H
X1
H
D
D

LM100
Y10
D
Y13
D
Y10
D
Y3
D
D
D

LM101
Y10
D
Y13
D
Y10
H
X4
H
D
D

LM102
Y10
D
Y13
D
Y10
D
Y12
D
D
D

LM103
X1
H
X6
H
X1
H
H
H
H
D

LM104
X1
H
X6
H
X1
H
H
H
D
H

LM105
X1
H
X6
H
X1
H
H
H
D
D

LM106
Y1
H
X6
H
Y1
H
H
H
D
D

LM107
Y2
H
X6
H
Y2
H
H
H
D
D

LM108
Y3
H
X6
H
Y3
H
H
H
D
D

LM109
Y3
D
X6
D
Y3
H
H
H
D
D

LM110
Y3
D
X6
D
Y3
D
H
H
D
D

LM111
Y3
D
X6
D
Y3
D
D
H
D
D

LM112
Y3
D
X6
D
Y3
D
D
D
D
D

LM113
Y3
D
Y14
D
Y3
D
D
D
D
D

LM114
Y3
D
Y14
D
Y3
H
X1
H
D
D

LM115
Y3
D
Y14
D
Y3
D
Y3
D
D
D

LM116
Y3
D
Y14
D
Y3
H
X4
H
D
D

LM117
Y3
D
Y14
D
Y3
D
Y12
D
D
D

LM118
X2
H
X6
H
X2
H
H
H
H
D

LM119
X2
H
X6
H
X2
H
H
H
D
H

LM120
X2
H
X6
H
X2
H
H
H
D
D

LM121
Y4
H
X6
H
Y4
H
H
H
D
D

LM122
Y5
H
X6
H
Y5
H
H
H
D
D

LM123
Y6
H
X6
H
Y6
H
H
H
D
D

LM124
Y7
H
X6
H
Y7
H
H
H
D
D

LM125
Y8
H
X6
H
Y8
H
H
H
D
D

LM126
Y9
H
X6
H
Y9
H
H
H
D
D

LM127
Y10
H
X6
H
Y10
H
H
H
D
D

LM128
Y10
D
X6
D
Y10
H
H
H
D
D

LM129
Y10
D
X6
D
Y10
D
H
H
D
D

LM130
Y10
D
X6
D
Y10
D
D
H
D
D

LM131
Y10
D
X6
D
Y10
D
D
D
D
D

LM132
Y10
D
Y14
D
Y10
D
D
D
D
D

LM133
Y10
D
Y14
D
Y10
H
X1
H
D
D

LM134
Y10
D
Y14
D
Y10
D
Y3
D
D
D

LM135
Y10
D
Y14
D
Y10
H
X4
H
D
D

LM136
Y10
D
Y14
D
Y10
D
Y12
D
D
D

LM137
X1
H
X7
H
X1
H
H
H
H
D

LM138
X1
H
X7
H
X1
H
H
H
D
H

LM139
X1
H
X7
H
X1
H
H
H
D
D

LM140
Y1
H
X7
H
Y1
H
H
H
D
D

LM141
Y2
H
X7
H
Y2
H
H
H
D
D

LM142
Y3
H
X7
H
Y3
H
H
H
D
D

LM143
Y3
D
X7
D
Y3
H
H
H
D
D

LM144
Y3
D
X7
D
Y3
D
H
H
D
D

LM145
Y3
D
X7
D
Y3
D
D
H
D
D

LM146
Y3
D
X7
D
Y3
D
D
D
D
D

LM147
Y3
D
X8
D
Y3
D
D
D
D
D

LM148
Y3
D
Y16
D
Y3
D
D
D
D
D

LM149
Y3
D
Y17
D
Y3
D
D
D
D
D

LM150
Y3
D
Y18
D
Y3
D
D
D
D
D

LM151
Y3
D
Y15
D
Y3
D
D
D
D
D

LM152
Y3
D
Y15
D
Y3
H
X1
H
D
D

LM153
Y3
D
Y15
D
Y3
D
Y3
D
D
D

LM154
Y3
D
Y16
D
Y3
D
Y3
D
D
D

LM155
Y3
D
Y17
D
Y3
D
Y3
D
D
D

LM156
Y3
D
Y18
D
Y3
D
Y3
D
D
D

LM157
Y3
D
Y15
D
Y3
H
X4
H
D
D

LM158
Y3
D
Y15
D
Y3
D
Y12
D
D
D

LM159
Y3
D
Y16
D
Y3
D
Y12
D
D
D

LM160
Y3
D
Y17
D
Y3
D
Y12
D
D
D

LM161
Y3
D
Y18
D
Y3
D
Y12
D
D
D

LM162
X2
H
X7
H
X2
H
H
H
H
D

LM163
X2
H
X7
H
X2
H
H
H
D
H

LM164
X2
H
X7
H
X2
H
H
H
D
D

LM165
Y4
H
X7
H
Y4
H
H
H
D
D

LM166
Y5
H
X7
H
Y5
H
H
H
D
D

LM167
Y6
H
X7
H
Y6
H
H
H
D
D

LM168
Y7
H
X7
H
Y7
H
H
H
D
D

LM169
Y8
H
X7
H
Y8
H
H
H
D
D

LM170
Y9
H
X7
H
Y9
H
H
H
D
D

LM171
Y10
H
X7
H
Y10
H
H
H
D
D

LM172
Y10
D
X7
D
Y10
H
H
H
D
D

LM173
Y10
D
X7
D
Y10
D
H
H
D
D

LM174
Y10
D
X7
D
Y10
D
D
H
D
D

LM175
Y10
D
X7
D
Y10
D
D
D
D
D

LM176
Y10
D
X8
D
Y10
D
D
D
D
D

LM177
Y10
D
Y16
D
Y10
D
D
D
D
D

LM178
Y10
D
Y17
D
Y10
D
D
D
D
D

LM179
Y10
D
Y18
D
Y10
D
D
D
D
D

LM180
Y10
D
Y15
D
Y10
D
D
D
D
D

LM181
Y10
D
Y15
D
Y10
H
X1
H
D
D

LM182
Y10
D
Y15
D
Y10
D
Y3
D
D
D

LM183
Y10
D
Y16
D
Y10
D
Y3
D
D
D

LM184
Y10
D
Y17
D
Y10
D
Y3
D
D
D

LM185
Y10
D
Y18
D
Y10
D
Y3
D
D
D

LM186
Y10
D
Y15
D
Y10
H
X4
H
D
D

LM187
Y10
D
Y15
D
Y10
D
Y12
D
D
D

LM188
Y10
D
Y16
D
Y10
D
Y12
D
D
D

LM189
Y10
D
Y17
D
Y10
D
Y12
D
D
D

LM190
Y10
D
Y18
D
Y10
D
Y12
D
D
D

LM191
X1
X7
H
H
X1
H
H
H
H
D

LM192
X1
X7
H
H
X1
H
H
H
D
H

LM193
X1
X7
H
H
X1
H
H
H
D
D

LM194
Y1
X7
H
H
Y1
H
H
H
D
D

LM195
Y2
X7
H
H
Y2
H
H
H
D
D

LM196
Y3
X7
H
H
Y3
H
H
H
D
D

LM197
Y3
X7
D
D
Y3
H
H
H
D
D

LM198
Y3
X7
D
D
Y3
D
H
H
D
D

LM199
Y3
X7
D
D
Y3
D
D
H
D
D

LM200
Y3
X7
D
D
Y3
D
D
D
D
D

LM201
Y3
Y15
D
D
Y3
D
D
D
D
D

LM202
Y3
Y16
D
D
Y3
D
D
D
D
D

LM203
Y3
Y17
D
D
Y3
D
D
D
D
D

LM204
Y3
Y18
D
D
Y3
D
D
D
D
D

LM205
Y3
Y15
D
D
Y3
H
X1
H
D
D

LM206
Y3
Y15
D
D
Y3
D
Y3
D
D
D

LM207
Y3
Y16
D
D
Y3
D
Y3
D
D
D

LM208
Y3
Y17
D
D
Y3
D
Y3
D
D
D

LM209
Y3
Y18
D
D
Y3
D
Y3
D
D
D

LM210
Y3
Y15
D
D
Y3
H
X4
H
D
D

LM211
Y3
Y15
D
D
Y3
D
Y12
D
D
D

LM212
Y3
Y16
D
D
Y3
D
Y12
D
D
D

LM213
Y3
Y17
D
D
Y3
D
Y12
D
D
D

LM214
Y3
Y18
D
D
Y3
D
Y12
D
D
D

LM215
X2
X7
H
H
X2
H
H
H
H
D

LM216
X2
X7
H
H
X2
H
H
H
D
H

LM217
X2
X7
H
H
X2
H
H
H
D
D

LM218
Y4
X7
H
H
Y4
H
H
H
D
D

LM219
Y5
X7
H
H
Y5
H
H
H
D
D

LM220
Y6
X7
H
H
Y6
H
H
H
D
D

LM221
Y7
X7
H
H
Y7
H
H
H
D
D

LM222
Y8
X7
H
H
Y8
H
H
H
D
D

LM223
Y9
X7
H
H
Y9
H
H
H
D
D

LM224
Y10
X7
H
H
Y10
H
H
H
D
D

LM225
Y10
X7
D
D
Y10
H
H
H
D
D

LM226
Y10
X7
D
D
Y10
D
H
H
D
D

LM227
Y10
X7
D
D
Y10
D
D
H
D
D

LM228
Y10
X7
D
D
Y10
D
D
D
D
D

LM229
Y10
X8
D
D
Y10
D
D
D
D
D

LM230
Y10
Y16
D
D
Y10
D
D
D
D
D

LM231
Y10
Y17
D
D
Y10
D
D
D
D
D

LM232
Y10
Y18
D
D
Y10
D
D
D
D
D

LM233
Y10
Y15
D
D
Y10
D
D
D
D
D

LM234
Y10
Y15
D
D
Y10
H
X1
H
D
D

LM235
Y10
Y15
D
D
Y10
D
Y3
D
D
D

LM236
Y10
Y16
D
D
Y10
D
Y3
D
D
D

LM237
Y10
Y17
D
D
Y10
D
Y3
D
D
D

LM238
Y10
Y18
D
D
Y10
D
Y3
D
D
D

LM239
Y10
Y15
D
D
Y10
H
X4
H
D
D

LM240
Y10
Y15
D
D
Y10
D
Y12
D
D
D

LM241
Y10
Y16
D
D
Y10
D
Y12
D
D
D

LM242
Y10
Y17
D
D
Y10
D
Y12
D
D
D

LM243
Y10
Y18
D
D
Y10
D
Y12
D
D
D

TABLE 5

Formula 1-2

Ligand

name
R₁₁
X₁₁
R₁₀₁
R₁₀₂
R₁₀₃
R₁₀₄
R₁₄
R₁₅
R₁₆
R₁₇
R₁₈
R₁₉
R₂₀

LFM1
Y10
N-Ph
D
D
D
D
D
Y10
D
D
D
D
D

LFM2
Y10
S
D
D
D
D
D
Y10
D
D
D
D
D

LFM3
Y10
O
D
D
D
D
D
Y10
D
D
D
D
D

LFM4
Y3
O
D
D
D
D
D
Y3
D
D
D
D
D

LFM5
Y10
O
D
D
D
D
D
Y10
D
D
D
D
D

LFM6
Y10
O
D
D
D
D
D
Y10
D
Y3
D
D
D

LFM7
Y10
O
D
D
D
D
D
Y10
D
Y12
D
D
D

TABLE 6

Formula 1-3

Ligand

name
R₁₁
X₁₁
R₁₀₁
R₁₀₂
R₁₀₃
R₁₀₄
R₁₄
R₁₅
R₁₆
R₁₇
R₁₈
R₁₉
R₂₀

LFP1
Y10
N-Ph
D
D
D
D
D
Y10
D
D
D
D
D

LFP2
Y10
S
D
D
D
D
D
Y10
D
D
D
D
D

LFP3
Y10
O
D
D
D
D
D
Y10
D
D
D
D
D

LFP4
Y30
O
D
D
D
D
D
Y3
D
D
D
D
D

LFP5
Y100
O
D
D
D
D
D
Y10
D
D
D
D
D

LFP6
Y100
O
D
D
D
D
D
Y10
D
Y3
D
D
D

LFP7
Y100
O
D
D
D
D
D
Y10
D
Y12
D
D
D

X₁to X₁₀and Y₁to Y₁₈in Tables 4 to 6 are the same as described below, and Ph in the tables refers to a phenyl group:

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In an embodiment, the sensitizer may include ac compound of Group VI

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In an embodiment, the sensitizer may include a thermally activated delayed fluorescence emitter represented by Formula 201 or 202.

For example, W₂₁₁in Formula 202 may be a substituted or unsubstituted electron-deficient nitrogen-free cyclic group.

In an embodiment, the π electron-deficient nitrogen-free cyclic group may be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a triindolobenzene group; or a condensed cyclic group of two or more π electron-deficient nitrogen-free cyclic groups, but embodiments of the present disclosure are not limited thereto.

For example, D₂₁₁in Formula 202 may be: —F, a cyano group, or a u electron-deficient nitrogen-containing cyclic group;

a C₁-C₆₀alkyl group, an π electron-deficient nitrogen-containing cyclic group, or an π electron-deficient nitrogen-free cyclic group, each substituted with at least one —F and a cyano group; or

an π-electron deficient nitrogen-containing cyclic group, substituted with at least one deuterium, a C₁-C₆₀alkyl group, an π-electron deficient nitrogen-containing cyclic group, an π electron-deficient nitrogen-free cyclic group, or any combination thereof.

In an embodiment, the π electron-deficient nitrogen-free cyclic group is the same as described above.

The term “π electron-deficient nitrogen-containing cyclic group” used herein refers to a cyclic group having at least one *—N=*′ moiety, and, for example, may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, and a benzimidazolobenzimidazole group; or a condensed cyclic group in which two or more π electron-efficient nitrogen-containing cyclic groups are condensed with each other.

In an embodiment, the sensitizer may be Groups VII to XIII, but embodiments of the present disclosure are not limited thereto:

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Hole Transport Region 12

The hole transport region 12 may be located between the first electrode 11 and the emission layer 15 of the organic light-emitting device 10.

The hole transport region 12 may have a single-layered structure or a multi-layered structure.

For example, the hole transport region 12 may have a hole injection layer, a hole transport layer, a hole injection layer/hole transport layer structure, a hole injection layer/first hole transport layer/second hole transport layer structure, a hole transport layer/middle layer structure, a hole injection layer/hole transport layer/middle layer structure, a hole transport layer/electron blocking layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, but embodiments of the present disclosure are not limited thereto.

The hole transport region 12 may include any compound having hole transport properties.

For example, the hole transport region 12 may include an amine-based compound.

In an embodiment, the hole transport region 1 may include at least one of a compound represented by Formula 201 to a compound represented by Formula 205, but embodiments of the present disclosure are not limited thereto:

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wherein, in Formulae 201 to 205,

L₂₀₁to L₂₀₉may each independently *-be O*′, *—S—*′, a substituted or unsubstituted C₅-C₆₀carbocyclic group, or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

xa1 to xa9 may each independently be an integer from 0 to 5, and

R₂₀₁to R₂₀₆may each independently be a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein neighboring two groups of R₂₀₁to R₂₀₆may optionally be linked to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.

For example,

L₂₀₁to L₂₀₉may be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or a triindolobenzene group, each unsubstituted or substituted with deuterium, a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triphenylenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and —Si(Q₁₁)(Q₁₂)(Q₁₃),

xa1 to xa9 may each independently be 0, 1, or 2, and

R₂₀₁to R₂₀₆may each independently be 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-bifluorenyl 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, a pyridinyl group, an indeno carbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, or a benzothienocarbazolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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-bifluorenyl 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, a pyridinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), or any combination thereof,

wherein Q₁₁to Q₁₃and Q₃₁to Q₃₃may each independently be a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

In one or more embodiments, the hole transport region 12 may include a carbazole-containing amine-based compound.

In an embodiment, the hole transport region 12 may include a carbazole-containing amine-based compound or a carbazole-free amine-based compound.

The carbazole-containing amine-based compound may be, for example, a compound represented by Formula 201 including a carbazole group and further including at least one of a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or any combination thereof.

The carbazole-free amine-based compound may be, for example, a compound represented by Formula 201 which does not include a carbazole group and which includes at least one of a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or any combination thereof.

In one or more embodiments, the hole transport region 12 may include at least one compound represented by Formulae 201 or 202, or a combination thereof.

In an embodiment, the hole transport region 12 may include at least one compound represented by Formulae 201-1, 202-1, 201-2, or any combination thereof, but embodiments of the present disclosure are not limited thereto.

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In Formulae 201-1, 202-1, and 201-2, L₂₀₁to L₂₀₃, L₂₀₅, xa1 to xa3, xa5, R₂₀₁, and R₂₀₂are the same as described herein, and R₂₁₁to R₂₁₃may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy 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 naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a dimethylfluorenyl group, a diphenyl fluorenyl group, a triphenylenyl 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, or a pyridinyl group.

For example, the hole transport region 12 may include at least one of Compounds HT1 to HT39, but embodiments of the present disclosure are not limited thereto.

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In one or more embodiments, hole transport region 12 of the organic light-emitting device 10 may further include a p-dopant. When the hole transport region 12 further includes a p-dopant, the hole transport region 12 may have a matrix (for example, at least one compound represented by Formulae 201 to 205) and a p-dopant included in the matrix. The p-dopant may be uniformly or non-uniformly doped in the hole transport region 12.

In an embodiment, the LUMO energy level of the p-dopant may be about −3.5 eV or less.

The p-dopant may include at least one of a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof, but embodiments of the present disclosure are not limited thereto.

In an embodiment, the p-dopant may include at least one of:

a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), F6-TCNNQ, or any combination thereof;

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

1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN);

a compound represented by Formula 221 below;

or a combination thereof,

but embodiments of the present disclosure are not limited thereto:

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In Formula 221,

R₂₂₁to R₂₂₃may each independently be 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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and at least one of R₂₂₁to R₂₂₃may have at least one cyano group, —F, —Cl, —Br, —I, C₁-C₂₀alkyl group substituted with —F, C₁-C₂₀alkyl group substituted with —Cl, C₁-C₂₀alkyl group substituted with —Br, C₁-C₂₀alkyl group substituted with —I, or any combination thereof.

The hole transport region 12 may have a thickness of about 100 Å to about 10000 Å, for example, about 400 Å to about 2000 Å, and the emission layer 15 may have a thickness of about 100 Å to about 3000 Å, for example, about 300 Å to about 1000 Å. When the thickness of each of the hole transport region 12 and the emission layer 15 is within these ranges described above, satisfactory hole transportation characteristics and/or luminescent characteristics may be obtained without a substantial increase in driving voltage.

Electron Transport Region 17

The electron transport region 17 is placed between the emission layer 15 and the second electrode 19 of the organic light-emitting device 10.

The electron transport region 17 may have a single-layered structure or a multi-layered structure.

For example, the electron transport region 17 may have an electron transport layer, an electron transport layer/electron injection layer structure, a buffer layer/electron transport layer structure, hole blocking layer/electron transport layer structure, a buffer layer/electron transport layer/electron injection layer structure, or a hole blocking layer/electron transport layer/electron injection layer structure, but embodiments of the present disclosure are not limited thereto. The electron transport region 17 may further include an electron control layer.

The electron transport region 17 may include known electron transport materials.

The electron transport region (for example, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-deficient nitrogen-containing cyclic group. The π electron-deficient nitrogen-containing cyclic group is the same as described above.

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

[Ar601]xe11-[(L601)xe1-R601]xe21 Formula 601

wherein, in Formula 601,

Ar₆₀₁and L₆₀₁may each independently be a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

xe11 may be 1, 2, or 3,

xe1 is an integer from 0 to 5,

R₆₀₁may be a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl 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 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁), —S(═O)₂(Q₆₀₁), or —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁to Q₆₀₃may each independently be a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and

xe21 is an integer from 1 to 5.

In one embodiment, at least one of Ar₆₀₁(s) in the number of xe11 and R₆₀₁(s) in the number of xe21 may include the π electron-deficient nitrogen-containing cyclic group.

In one embodiment, ring Ar₆₀₁and L₆₀₁in Formula 601 may each independently be a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof,

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

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

In one or more embodiments, Ar₆₀₁in Formula 601 may be an anthracene group.

In one or more embodiments, the compound represented by Formula 601 may be represented by Formula 601-1.

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In Formula 601-1,

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

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

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

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

R₆₁₄to R₆₁₆may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, 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, or a naphthyl group.

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

In one or more embodiments, R₆₀₁and R₆₁₁to R₆₁₃in Formulae 601 and 601-1 may each independently be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl 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, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, or an azacarbazolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl 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, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, or any combination thereof; or

—S(═O)₂(Q₆₀₁) or —P(═O)(Q₆₀₁)(Q₆₀₂),

wherein Q₆₀₁and Q₆₀₂are the same as described above.

The electron transport region may include at least one compound of Compounds ET1 to ET36, but embodiments of the present disclosure are not limited thereto:

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In one or more embodiments, the electron transport region may include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-dphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), NTAZ, or any combination thereof.

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Thicknesses of the buffer layer, the hole blocking layer, and the electron control layer may each independently be in the range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, excellent hole blocking characteristics or excellent electron control characteristics may be obtained without a substantial increase in driving voltage.

A thickness of the electron transport layer may be in the 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 the range described above, the electron transport layer may have satisfactory electron transporting characteristics without a substantial increase in driving voltage.

The electron transport region 17 (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.

The metal-containing material may include at least one alkali metal complex and alkaline earth-metal complex. The alkali metal complex may include a metal ion of a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the alkaline earth-metal complex may include a metal ion of a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may be a hydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, a hydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxy phenylpyridine, a hydroxy phenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, a phenanthroline, or a cyclopentadiene, but embodiments of the present disclosure are not limited thereto.

In an embodiment, the metal-containing material may include a L₁complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate, LiQ) or ET-D2:

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The electron transport region 17 may include an electron injection layer that facilitates the injection of electrons from the second electrode 19. The electron injection layer may directly contact the second electrode 19.

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 include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof.

The alkali metal may be Li, Na, K, Rb, or Cs. In an embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but embodiments of the present disclosure are not limited thereto.

The alkaline earth metal may be Mg, Ca, Sr, or Ba.

The rare earth metal may be Sc, Y, Ce, Tb, Yb, or Gd.

The alkali metal compound, the alkaline earth-metal compound, and the rare earth metal compound may be an oxide or a halides (for example, fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth-metal, or the rare earth metal.

The alkali metal compound may be an alkali metal oxide, such as Li₂O, Cs₂O, or K₂O, or an alkali metal halide, such as LiF, NaF, CsF, KF, LiI, Nal, CsI, or KI. In an embodiment, the alkali metal compound may be LiF, Li₂O, NaF, LiI, Nal, CsI, or KI, but embodiments of the present disclosure are not limited thereto.

The alkaline earth-metal compound may be an alkaline earth-metal oxide, such as BaO, SrO, CaO, Ba_xSr_1-xO (0<x<1), or Ba_xCa_1-xO (0<x<1). In an embodiment, the alkaline earth-metal compound may be BaO, SrO, or CaO, but embodiments of the present disclosure are not limited thereto.

The rare earth metal compound may be of YbF₃, ScF₃, Sc₂O₃, Y₂O₃, Ce₂O₃, GdF₃, or TbF₃. In an embodiment, the rare earth metal compound may be YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, or TbI₃, but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include an ion of alkali metal, alkaline earth-metal, or rare earth metal as described above, and a ligand coordinated with a metal ion of the alkali metal complex, the alkaline earth-metal complex, or the rare earth metal complex may be hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxy phenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole, hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine, phenanthroline, or cyclopentadiene, but embodiments of the present disclosure are not limited thereto.

The electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.

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

Second Electrode 19

The second electrode 19 is located on the organic layer 10A having such a structure. The second electrode 19 may be a cathode which is an electron injection electrode, and in this regard, a material for forming the second electrode 19 may be a metal, an alloy, an electrically conductive compound, or any combination thereof, which may have a relatively low work function.

The second electrode 19 may include at least one lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, IZO, or any combination thereof, but embodiments of the present disclosure are not limited thereto. The second electrode 19 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 19 may have a single-layered structure having a single layer or a multi-layered structure including two or more layers.

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

Description of FIG. 2

FIG. 2 is a schematic cross-sectional view of an organic light-emitting device 100 according to another exemplary embodiment.

The organic light-emitting device 100 of FIG. 2 includes a first electrode 110, a second electrode 190 facing the first electrode 110, and a first emission unit 151 and a second emission unit 152 between the first electrode 110 and the second electrode 190. A charge generating layer 141 is located between the first emission unit 151 and the second emission unit 152, and the charge generating layer 141 may include an n-type charge generating layer 141-N and a p-type charge generating layer 141-P. The charge generating layer 141 is a layer that generates charge and supplies the charge to neighboring emission units, and any known material may be used therefor.

The first emission unit 151 may include a first emission layer 151-EM, and the second emission unit 152 may include a second emission layer 152-EM. The maximum emission wavelength of light emitted from the first emission unit 151 may be different from the maximum emission wavelength of light emitted from the second emission unit 152. For example, the mixed light of the light emitted from the first emission unit 151 and the light emitted from the second emission unit 152 may be white light, but embodiments of the present disclosure are not limited thereto.

The hole transport region 120 is located between the first emission unit 151 and the first electrode 110, and the second emission unit 152 may include the first hole transport region 121 located on the side of the first electrode 110.

An electron transport region 170 is located between the second emission unit 152 and the second electrode 190, and the first emission unit 151 may include a first electron transport region 171 located between the charge generating layer 141 and the first emission layer 151-EM.

The first emission layer 151-EM may include the composition described above.

For example, the first light emitting layer 151-EM may include a host, a dopant, and a sensitizer, wherein the sensitizer includes a first compound in the composition, and the dopant includes a second compound in the composition, and the host includes at least one third compound in the composition.

The second emission layer 151-EM may include the composition described above.

For example, the second emission layer 152-EM may include a host, a dopant, and a sensitizer, wherein the sensitizer includes a first compound in the composition, and the dopant includes a second compound in the composition, and the host includes at least one third compound in the composition.

The first electrode 110 and the second electrode 190 illustrated in FIG. 2 may be the same as described in connection with the first electrode 11 and the second electrode 19 illustrated in FIG. 1.

The first emission layer 151-EM and the second emission layer 152-EM illustrated in FIG. 2 are each the same as described in connection with the emission layer 15 illustrated in FIG. 2.

The hole transport region 120 and the first hole transport region 121 illustrated in FIG. 2 are each the same as described in connection with the hole transport region 12 illustrated in FIG. 1.

The electron transport region 170 and the first electron transport region 171 illustrated in FIG. 2 are each the same as described in connection with the electron transport region 17 illustrated in FIG. 1.

As described above, referring to FIG. 2, an organic light-emitting device in which each of the first emission unit 151 and the second emission unit 152 includes an emission layer including a host, a dopant, and a sensitizer, has been described. However, the organic light-emitting device may have various other forms. For example, one of the first emission unit 151 and the second emission unit 152 of the organic light-emitting device 100 of FIG. 2 may be replaced with any known emission unit, or may include three or more emission units.

Description of FIG. 3

FIG. 3 is a schematic cross-sectional view of an organic light-emitting device 200 according to another embodiment.

The organic light-emitting device 200 may include a first electrode 210, a second electrode 290 facing the first electrode 210, and a first emission layer 251 and a second emission layer 252 which are stacked between the first electrode 210 and the second electrode 290.

The maximum emission wavelength of light emitted from the first emission layer 251 may be different from the maximum emission wavelength of light emitted from the second emission layer 252. For example, the mixed light of the light emitted from the first emission layer 251 and the light emitted from the second emission layer 252 may be white light, but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, a hole transport region 220 may be located between the first emission layer 251 and the first electrode 210, and an electron transport region 270 may be located between the second emission layer 252 and the second electrode 290.

The first emission layer 251 may include the composition described above.

For example, the first emission layer 251 may include a host, a dopant, and a sensitizer, wherein the sensitizer includes a first compound in the composition, and the dopant includes a second compound in the composition, and the host includes at least one third compound in the composition.

The second emission layer 252 may include the composition described above.

For example, the second emission layer 252 may include a host, a dopant, and a sensitizer, wherein the sensitizer includes a first compound in the composition, and the dopant includes a second compound in the composition, and the host includes at least one third compound in the composition.

The first electrode 210, the hole transport region 220, and the second electrode 290 illustrated in FIG. 3 are respectively the same as described in connection with the first electrode 11, the hole transport region 12, and the second electrode 19 illustrated in FIG. 1.

The first emission layer 251 and the second emission layer 252 illustrated in FIG. 4 are each the same as described in connection with the emission layer 15 illustrated in FIG. 1.

The electron transport region 270 illustrated in FIG. 3 may be the same as described in connection with the electron transport region 17 in FIG. 1.

As described above, referring to FIG. 3, an organic light-emitting device, in which each of the first emission layer 251 and the second emission layer 252 includes a host, a dopant, and a sensitizer, has been described. However, the organic light-emitting device may have various other forms. For example, one of the first emission layer 251 and the second emission layer 252 of the organic light-emitting device 200 of FIG. 3 may be replaced with any known emission layer, or an interlayer may be additionally located between neighboring emission layers.

Explanation of Terms

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

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

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

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

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

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

The term “C₃-C₁₀cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

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

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

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having a heterocarbocyclic aromatic system that has at least one heteroatom N, O, P, Si, S, Se, Ge, B, or any combination thereof as a ring-forming atom, and 1 to 60 carbon atoms. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having a carbocyclic aromatic system that has at least one heteroatom N, O, P, S, Se, Ge, B, or any combination thereof as a ring-forming atom, and 1 to 60 carbon atoms. Examples of the C₁-C₆₀heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C₆-C₆₀heteroaryl group and the C₆-C₆₀heteroarylene group each include two or more rings, the rings may be fused to each other.

The term “C₆-C₆₀aryloxy group” as used herein indicates —OA₁₀₂(wherein A₁₀₂is the C₆-C₆₀aryl group), and the term “C₆-C₆₀arylthio group” as used herein indicates —SA₁₀₃(wherein A₁₀₃is the C₆-C₆₀aryl group).

The term “monovalent non-aromatic condensed polycyclic group” used herein refers to a monovalent group in which two or more rings are condensed with each other, only carbon is used as a ring-forming atom (for example, the number of carbon atoms may be 8 to 60) and the whole molecule is a non-aromaticity group. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group having two or more rings condensed to each other, a heteroatom N, O, P, Si, S, Se, Ge, B, or any combination thereof other than carbon atoms (for example, having 1 to 60 carbon atoms), as a ring-forming atom, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic heterocondensed polycyclic group” as used herein refers to a divalent group having the same structure as a monovalent non-aromatic heterocondensed polycyclic group.

The term “C₅-C₃₀carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C₅-C₃₀carbocyclic group may be a monocyclic group or a polycyclic group, and may be a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group, depending on the formula structure.

The term “C₁-C₃₀heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom N, O, Si, P, S, Se, Ge, B, or any combination thereof other than 1 to 30 carbon atoms. The C₁-C₃₀heterocyclic group may be a monocyclic group or a polycyclic group, and may be a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group, depending on the formula structure.

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

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

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

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

wherein Q₁to Q₉, Q₁₁to Q₁₉, Q₂₁to Q₂₉and Q₃₁to Q₃₉may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryl group substituted with at least one a C₁-C₆₀alkyl group, and a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof.

The term “room temperature” used herein refers to a temperature of about 25° C.

The terms “a biphenyl group, a terphenyl group, and a quaterphenyl group” used herein respectively refer to monovalent groups in which two, three, or four phenyl groups which are linked together via a single bond.

The terms “a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, and a cyano-containing quaterphenyl group” used herein respectively refer to a phenyl group, a biphenyl group, a terphenyl group, and a quaterphenyl group, each of which is substituted with at least one cyano group. In “a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, and a cyano-containing quaterphenyl group”, a cyano group may be substituted to any position of the corresponding group, and the “cyano-containing phenyl group, the cyano-containing biphenyl group, the cyano-containing terphenyl group, and the cyano-containing quaterphenyl group” may further include substituents other than a cyano group. For example, a phenyl group substituted with a cyano group, and a phenyl group substituted with a cyano group and a methyl group may all belong to “a cyano-containing phenyl group.”

Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Examples and Examples. However, the organic light-emitting device is not limited thereto. The wording 13′ was used instead of ‘A″’ used in describing Synthesis Examples means that an amount of ‘A’ used was identical to an amount of ‘B’ used, in terms of a molar equivalent.

EXAMPLES
Synthesis Example 1 (Synthesis of FD24)

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Synthesis of Intermediate (A)

5.62 g of carbazole (33.61 mmol), 14.52 g of 1,6-dibromopyrene (40.33 mmol), 1.93 g of Pd(dba)₂(3.36 mmol), 9.69 g of sodium tert-butoxide (100.82 mmol), and 3.89 g of xantphos (6.72 mmol) were dissolved in 560 ml of toluene, and then, the resultant mixture was stirred while refluxing for 24 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, toluene was completely removed therefrom, the residue was boiled and dissolved in 1 L of dichloromethane, and was filtered under reduced pressure through a silica gel. The filtrate was concentrated under reduced pressure and the product obtained therefrom was separated by silica gel column chromatography to obtain a target compound of 4.85 g of Intermediate (A) (yield of 32%).

LC-Mass (calculated: 445.05 g/mol, found: M⁺¹=446 g/mol)

Synthesis of Intermediate (B)

7.90 g of [1,1′-biphenyl]-3-amine (46.67 mmol), 11.97 g of 4-bromo-1,1′-biphenyl (51.33 mmol), 0.86 g of Pd₂(dba)₃(0.93 mmol), 0.76 g of 50% of tri-tert-butylphosphine solution (1.87 mmol), and 4.93 g of sodium tert-butoxide (51.33 mmol) were dissolved in 233 ml of Xylene, and then, the resultant mixture was stirred while refluxing for 18 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and an organic layer was extracted and separated with dichloromethane. Water was removed from the recovered organic layer with magnesium sulfate and the organic layer was filtered under reduced pressure. The obtained filtrate was separated by silica gel column chromatography to obtain a target compound of 11.30 g of Intermediate (B) (yield of 75%).

LC-Mass (calculated: 321.15 g/mol, found: M+1=322 g/mol)

Synthesis of FD24

1.30 g of Intermediate (A) (2.91 mmol), 1.03 g of Intermediate (B) (3.20 mmol), 0.17 g of Pd(dba)₂(0.29 mmol), 0.98 g of potassium tert-butoxide (8.74 mmol), and 0.24 g of 50% of tri-tert-butylphosphine solution (0.58 mmol) were dissolved in 7.30 ml of toluene, and then, the resultant mixture was stirred while refluxing for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, methanol was added thereto, was stirred while refluxing for 1 hour, and was filtered under reduced pressure. The obtained solid was boiled and dissolved in toluene and was filtered under reduced pressure through a silica gel, the filtrate was concentrated under reduced pressure, and the obtained product was recrystallized with toluene to obtain a target compound of 0.98 g of FD24 (yield of 49%).

LC-Mass (calculated: 686.27 g/mol, found: M+1=687 g/mol)

Synthesis Example 2 (Synthesis of FD157)

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Synthesis of Intermediate (C)

15.01 g of 3,6-di-tert-butyl-9H-carbazole (53.71 mmol), 23.21 g of 1,6-dibromopyrene (64.45 mmol), 3.09 g of Pd(dba)₂(5.37 mmol), 15.49 g of sodium tert-butoxide (161.13 mmol), and 6.22 g of xantphos (10.74 mmol) were dissolved in 895 ml of toluene, and then, the resultant mixture was stirred while refluxing for 24 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, toluene was completely removed therefrom, the residue was boiled and dissolved in 1.5 L of dichloromethane, and was filtered under reduced pressure through a silica gel. The filtrate was concentrated under reduced pressure and the product obtained therefrom was separated by silica gel column chromatography to obtain a target compound of 8.41 g of Intermediate (C) (yield of 28%).

LC-Mass (calculated: 555.17 g/mol, found: M+1=556 g/mol)

Synthesis of FD157

2.45 g of Intermediate (C) (4.38 mmol), 1.55 g of Intermediate (B) (4.82 mmol), 0.25 g of Pd(dba)₂(0.44 mmol), 1.48 g of potassium tert-butoxide (13.14 mmol), and 0.35 g of 50% of tri-tert-butylphosphine solution (1.75 mmol) were dissolved in 10.95 ml of toluene, and then, the resultant mixture was stirred while refluxing for 3 hours. After completion of the reaction, the reactant was cooled to room temperature, methanol was added thereto, was stirred while refluxing for 1 hour, and was filtered under reduced pressure. The obtained solid was separated by silica gel column chromatography and then concentrated under reduced pressure. The obtained product was recrystallized under ethyl acetate/methanol conditions to obtain a target compound of 0.90 g of FD157 (yield of 26%).

LC-Mass (calculated: 798.40 g/mol, found: M+1=799 g/mol)

Synthesis Example 3 (Synthesis of FD470)

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Synthesis of Intermediate (D)

In the synthesis of Intermediate (B), 3′,5′-di-tert-butyl-[1,1′-biphenyl]-3-amine and 4′-bromo-3,5-di-tert-butyl-1,1′-biphenyl were each used instead of [1,1′-biphenyl]-3-amine and 4-bromo-1,1′-biphenyl. Synthesis and purification were carried out in the same way as that of Intermediate (B) to obtain a target compound of 8.60 g of Intermediate (D) (yield of 69%).

LC-Mass (calculated: 545.40 g/mol, found: M+1=546 g/mol)

Synthesis of FD470

In the synthesis of FD157, Intermediate (D) was used instead of Intermediate (4). Synthesis and purification were carried out in the same way as that of FD157 to obtain a target compound of 0.63 g of FD470 (yield of 52%).

LC-Mass (calculated: 1,022.65 g/mol, found: M+1=1,023 g/mol)

Synthesis Example 4 (Synthesis of FD23)

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Synthesis of Intermediate (E)

In the synthesis of Intermediate (B), [1,1′-biphenyl]-3-amine and 3-bromo-1,1′-biphenyl were each used instead of [1,1′-biphenyl]-3-amine and 4-bromo-1,1′-biphenyl. Synthesis and purification were carried out in the same way as that of Intermediate (B) to obtain a target compound of 11.3 g of Intermediate (E) (yield of 76%).

LC-Mass (calculated: 321.15 g/mol, found: M+1=322 g/mol)

Synthesis of FD23

In the synthesis of FD24, Intermediate (E) was used instead of Intermediate (B). Synthesis and purification were carried out in the same way as that of FD24 to obtain a target compound of 0.85 g of FD23 (yield of 49%).

LC-Mass (calculated: 686.27 g/mol, found: M+1=687 g/mol)

Synthesis Example 5 (Synthesis of FD156)

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Synthesis of FD156

In the synthesis of FD157, Intermediate (E) was used instead of Intermediate (B). Synthesis and purification were carried out in the same way as that of FD157 to obtain a target compound of 0.35 g of FD156 (yield of 51%).

LC-Mass (calculated: 798.40 g/mol, found: M+1=799 g/mol)

Synthesis Example 6 (Synthesis of FD461)

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Synthesis of Intermediate (F)

In the synthesis of Intermediate (B), 3′,5′-di-tert-butyl-[1,1′-biphenyl]-3-amine and 3′-bromo-3,5-di-tert-butyl-1,1′-biphenyl were each used instead of [1,1′-biphenyl]-3-amine and 4-bromo-1,1′-biphenyl. Synthesis and purification were carried out in the same way as that of Intermediate (B) to obtain a target compound of 9.7 g of Intermediate (F) (yield of 65%).

LC-Mass (calculated: 545.40 g/mol, found: M+1=546 g/mol)

Synthesis of FD461

In the synthesis of FD157, Intermediate (F) was used instead of Intermediate (B). Synthesis and purification were carried out in the same way as that of FD157 to obtain a target compound of 0.88 g of FD461 (yield of 53%).

LC-Mass (calculated: 1,022.65 g/mol, found: M+1=1,023 g/mol)

Synthesis Example 7 (Synthesis of FD22)

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Synthesis of Intermediate (g)

In the synthesis of Intermediate (B), [1,1′-biphenyl]-2-amine was used instead of [1,1′-biphenyl]-3-amine. Synthesis and purification were carried out in the same way as that of Intermediate (B) to obtain a target compound of 6.9 g of Intermediate (F) (yield of 64%).

LC-Mass (calculated: 321.15 g/mol, found: M+1=322 g/mol)

Synthesis of FD22

In the synthesis of FD24, Intermediate (g) was used instead of Intermediate (B). Synthesis and purification were carried out in the same way as that of FD24 to obtain a target compound of 0.33 g of FD22 (yield of 39%).

LC-Mass (calculated: 686.27 g/mol, found: M+1=687 g/mol)

Synthesis Example 8 (Synthesis of FD451)

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Synthesis of Intermediate (H)

In the synthesis of Intermediate (B), 3′,5′-di-tert-butyl-[1,1′-biphenyl]-2-amine and 4′-bromo-3,5-di-tert-butyl-1,1′-biphenyl were each used instead of [1,1′-biphenyl]-3-amine and 4-bromo-1,1′-biphenyl. Synthesis and purification were carried out in the same way as that of Intermediate (B) to obtain a target compound of 4.9 g of Intermediate (h) (yield of 45%).

LC-Mass (calculated: 545.40 g/mol, found: M+1=546 g/mol)

Synthesis of FD451

In the synthesis of FD157, Intermediate (h) was used instead of Intermediate (B). Synthesis and purification were carried out in the same way as that of FD157 to obtain a target compound of 0.35 g of FD156 (yield of 51%).

LC-Mass (calculated: 1,022.65 g/mol, found: M+1=1,023 g/mol)

Comparative Synthesis Example 1 (FD-A)

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Synthesis of FD-A

2.14 g of 1,6-dibromopyrene (5.94 mmol), 4.78 g of Intermediate (g) (14.86 mmol), 0.34 g of Pd(dba)₂(0.59 mmol), 2.01 g of potassium tert-butoxide (17.83 mmol), and 0.48 g of 50% of tri-tert-butylphosphine solution (1.19 mmol) were dissolved in 14.9 ml of toluene, and then, the resultant mixture was stirred while refluxing for 0.5 hours. After completion of the reaction, methanol was added to the reaction mixture, stirred while refluxing for 18 hours, and then filtered under reduced pressure. The obtained solid was boiled and dissolved in toluene and was filtered under reduced pressure through a silica gel, the filtrate was concentrated under reduced pressure, and the obtained product was recrystallized under a toluene/DMF condition to obtain a target compound of 3.50 g of FD-A (yield of 70%).

LC-Mass (calculated: 840.35 g/mol, found: M+1=841 g/mol)

Comparative Synthesis Example 2 (FD-B)

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Synthesis of FD-B

1.40 g of 1,6-dibromopyrene (3.88 mmol), 5.29 g of Intermediate (F) (9.69 mmol), 0.22 g of Pd(dba)₂(0.39 mmol), 1.31 g of potassium tert-butoxide (11.63 mmol), and 0.31 g of 50% of tri-tert-butylphosphine solution (1.55 mmol) were dissolved in 9.7 ml of toluene, and then, the resultant mixture was stirred while refluxing for 3 hours. After completion of the reaction, the reactant was cooled to room temperature, methanol was added thereto, was stirred while refluxing for 1 hour, and the residue was filtered under reduced pressure. The obtained solid was separated by silica gel column chromatography and then concentrated under reduced pressure. The obtained product was recrystallized under a dichloromethane/hexane condition to obtain a target compound of 2.50 g of FD-B (yield of 50%).

LC-Mass (calculated: 1,288.85 g/mol, found: M+1=1,290 g/mol)

Evaluation Example 1

Using the Gaussian 09 program, the HOMO, LUMO, S1, T1 energy levels, and FWHM of each compound of Table 7 were evaluated using a quantum chemical calculation method according to the DFT based on the 6-311+G(d,p) basis set, and the result thereof is shown in Table 7.

TABLE 7

Compound
HOMO
LUMO
S1
T1

No.
(eV)
(eV)
(eV)
(eV)

FD22
−4.97
−1.74
2.85
2.01

FD23
−5.04
−1.82
2.86
2.07

FD
−5.00
−1.84
2.80
2.06

FD 15246
−5.00
−1.80
2.85
2.07

FD 157
−4.96
−1.80
2.81
2.06

FD 451
−4.89
−1.72
2.82
2.03

FD 461
−4.94
−1.75
2.84
2.06

FD 470
−4.89
−1.76
2.79
2.06

FD-A
−4.66
−1.51
2.79
1.99

FD-B
−4.73
−1.61
2.78
2.00

Example 1

An ITO glass substrate was cut to a size of 50 mm×50 mm×0.5 mm and then, sonicated in acetone isopropyl alcohol and pure water, each for 15 minutes, and then, cleaned by exposure to UV and ozone for 30 minutes.

Subsequently, F6-TCNNQ was deposited on the ITO electrode (anode) on the glass substrate to form a hole injection layer having a thickness of 100 Å, and HT1 was deposited on the hole injection layer to form a hole transport layer having a thickness of 1,260 Å to thereby form a hole transport region.

Compound H-H1 (first host), Compound H-E1 (second host), and Compound SP001 (sensitizer) (Here, the weight ratio of the first host, the second host, and the sensitizer is 45:45:10) and FD1 (dopant) (Here, the dopant is 0.1 wt % based on the total amount of the first host, the second host, the sensitizer, and the dopant) were co-deposited on the hole transport region to form an emission layer having a thickness of 400 Å.

Compound ET17 and Liq were co-deposited on the emission layer to a weight ratio of 5:5 to form an electron transport layer having a thickness of 360 Å, and then, LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 5 Å, and then, an Al having a thickness of 800 Å was formed on the electron injection layer, thereby completing the manufacture of an organic light-emitting device.

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Example 2 to 8 and Comparative Example 1

An organic light-emitting device was manufactured in the same manner as in Example 1, except that, in forming an emission layer, for use as a sensitizer and a dopant, corresponding compounds and amount shown in Table 8 were used.

TABLE 8

Second

First host
host
Sensitizer
Dopant

Example 1
H-H1
H-E1
122
FD24

Example 2
H-H1
H-E1
122
FD157

Example 3
H-H1
H-E1
122
FD470

Example 4
H-H1
H-E1
122
FD23

Example 5
H-H1
H-E1
122
FD461

Example 6
H-H1
H-E1
122
FD156

Example 7
H-H1
H-E1
122
FD22

Example 8
H-H1
H-E1
122
FD451

Comparative
H-H1
H-E1
122
FD-A

Example 1

Comparative
H-H1
H-E1
122
FD-B

Example 2

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122

Evaluation Example 2: OLED Lifespan and Evaluation of External Quantum Efficiency

(1) The driving voltage, the external quantum efficiency (EQE), and the lifespan (T₉₅) of each of the organic light-emitting devices manufactured according to Examples 1 to 8 and Comparative Examples 1 and 2 were evaluated. Results thereof are shown in Table 9. The value of the driving voltage, the external quantum efficiency, and the lifespan were each represented as a relative value, based on the value of Comparative Example 1 as 100%.

TABLE 9

Driving
Lifespan

voltage
(T₉₅)
EQE

(%)
(%)
(%)

Example 1
96
636
275

Example 2
93
588
235

Example 3
92
639
200

Example 4
94
486
279

Example 5
94
461
265

Example 6
96
509
221

Example 7
97
197
150

Example 8
94
274
215

Comparative
100
100
100

Example 1

Comparative
97
131
135

Example 2

The organic light-emitting devices according to embodiments of the present disclosure have high efficiency and a long lifespan.

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.

ORGANIC LIGHT-EMITTING DEVICE

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