ORGANIC LIGHT-EMITTING DEVICE

CROSS-REFERENCE TO RELATED APPLICATION

This application is based on and claims priority to Korean Patent Application No. 10-2021-0002217, filed on Jan. 7, 2021, in the Korean Intellectual Property Office, and all the benefits accruing therefrom under 35 U.S.C. § 119, the entire content of which is incorporated by reference herein.

BACKGROUND
1. Field

The present disclosure relates to an organic light-emitting device.

2. Description of the Related Art

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

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

Various types of organic light emitting devices are known. However, there still remains a need in OLEDs having one or more, preferably all, of high efficiency, long lifespan, and high triplet-triplet fusion (TTF) ratio characteristics.

SUMMARY

Provided herein is an organic light-emitting device including a silane compound as a host, thus having high efficiency, long lifespan, and high triplet-triplet fusion (TTF) ratio characteristics.

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

According to an aspect of an embodiment, an organic light-emitting device may include:

a first electrode,

a second electrode, and

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

an emission layer,

wherein the emission layer may include a host and a dopant, and

the host may include at least one silane compound represented by Formula 1.

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wherein in Formula 1,

Ar₁to Ar₃may each independently be 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 C₁-C₆₀alkylthio 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 C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉),

at least one of Ar₁to Ar₃may be 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,

L₁₀may be a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

a10 may be an integer from 1 to 3, and when a10 is 2 or greater, at least two L₁₀(s) may be identical to or different from each other,

R₁₀and R₂₀may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an am idino 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 C₁-C₆₀alkylthio 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 C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉),

- b10 and b20 may each independently be an integer from 1 to 8,

when b10 is 2 or greater, at least two R₁₀(s) may be identical to or different from each other, and when b20 is 2 or greater, at least two R₂₀(s) may be identical to or different from each other,

c10 may be an integer from 1 to 9,

when c10 is 2 or greater, at least two -[(L₁₀)_a10-(R₁₀)_b10](s) may be identical to or different from each other,

at least one substituent of the substituted C₅-C₃₀carbocyclic group, the substituted C₁-C₃₀heterocyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₁-C₆₀alkylthio group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted C₁-C₆₀heteroaryloxy group, the substituted C₁-C₆₀heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, or the substituted monovalent non-aromatic condensed heteropolycyclic group may be

deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkylthio group, or a C₁-C₆₀alkoxy group,

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkylthio group, or a C₁-C₆₀alkoxy group, each independently 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₄)(Q₁₅), or —B(Q₁₆)(Q₁₇),

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 C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each independently 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 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 C₁-C₆₀alkylthio 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 C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₄)(Q₂₅), or —B(Q₂₆)(Q₂₇), or

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

wherein Q₁to Q₉, 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 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 C₁-C₆₀alkylthio 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 C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and

wherein substituents L₁₀, R₁₀, and R₂₀are present on each ring through which the bond with the corresponding substituent passes.

BRIEF DESCRIPTION OF THE DRAWING

The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the FIGURE, which shows a schematic cross-sectional view of an organic light-emitting device according to an embodiment.

DETAILED DESCRIPTION

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

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

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

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

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

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

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

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

In any formula, * and *′ each indicate a binding site to a neighboring atom or a neighboring functional group.

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

According to an embodiment, a silane compound represented by Formula 1 may be provided:

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wherein, in Formula 1, Ar₁to Ar₃may each independently be 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 C₁-C₆₀alkylthio 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 heteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉), or

at least one of Ar₁to Ar₃may be a substituted or unsubstituted C₆-C₆₀aryl 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.

In an embodiment, Ar₁to Ar₃may each independently be:

a C₁-C₂₀alkyl group, C₁-C₂₀alkylthio group, or a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group, C₁-C₂₀alkylthio group, or a C₁-C₂₀alkoxy group, each independently substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an am idino 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 pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, or a triazinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl 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 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a phenoxazinyl group, a phenothiazinyl group, an imidazopyrimidinyl group, or an imidazopyridinyl group, each independently substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, or a quinazolinyl group.

In an embodiment, at least one of Ar₁to Ar₃may be:

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl 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 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a phenoxazinyl group, a phenothiazinyl group, an imidazopyrimidinyl group, or an imidazopyridinyl group, each independently substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an am idino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, or a quinazolinyl group.

In an embodiment, Ar₁to Ar₃may each independently be a substituted or unsubstituted C₆-C₆₀aryl 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.

In an embodiment, Ar₁to Ar₃may each independently be: a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl 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 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a phenoxazinyl group, a phenothiazinyl group, an imidazopyrimidinyl group, or an imidazopyridinyl group; or

In an embodiment, Ar₁to Ar₃may each independently be:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a phenoxazinyl group, or a phenothiazinyl group, each independently substituted with at least one of deuterium, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

In Formula 1, L₁₀may be a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group.

In an embodiment, L₁₀may be: a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentacenylene group, a carbazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, a pyridinylene group, a pyrimidinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a phenoxazinylene group, a phenothiazinylene group, an azacarbazolylene group, an azadibenzofuranylene group, or an azadibenzothiophenylene group;

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentacenylene group, a carbazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, a pyridinylene group, a pyrimidinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a phenoxazinylene group, a phenothiazinylene group, an azacarbazolylene group, an azadibenzofuranylene group, or an azadibenzothiophenylene group, each independently substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an am idino 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 C₁-C₆₀alkylthio group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group; or

a group represented by Formula 2A or Formula 2B:

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wherein, in Formulae 2A and 2B,

Y₂₁to Y₂₄may each independently be a single bond, O, S, N(R₂₁), C(R₂₁)(R₂₂), Si(R₂₁)(R₂₂), C(═O), S(═O), S(═O)₂, B(R₂₁), P(R₂₁), or P(═O)(R₂₁),

A₂₁to A₂₃may each independently be a phenyl group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group,

R₂₁and R₂₂may each independently be understood by referring to the description of R₁₀or R₂₀provided herein, and

* and *′ each indicate a binding site to an adjacent atom.

In an embodiment, in Formulae 2A and 2B, Y₂₁to Y₂₄may each independently be a single bond, O, S, N(R₂₁), C(R₂₁)(R₂₂), or Si(R₂₁)(R₂₂).

In an embodiment, Y₂₁and Y₂₂may not each be a single bond simultaneously, and Y₂₃and Y₂₄may not each be a single bond simultaneously.

In an embodiment, A₂₁to A₂₃may each independently be a phenyl group, a naphthalene group, a pyridine group, or a pyrimidine group.

In an embodiment, A₂₁to A₂₃may each independently be a phenyl group or a naphthalene group.

In Formula 1, a10 may be an integer from 0 to 3, and when a10 is 2 or greater, at least two L₁₀(s) may be identical to or different from each other.

In an embodiment, a10 may be 0 or 1. For example, a10 may be 0. In an embodiment, a10 may be 1.

In an embodiment, when a10 is 0, -(L₁₀)_a10- represents a single bond.

In Formula 1, R₁₀and R₂₀may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₁-C₆₀alkylthio 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 C₁-C₆₀heteroaryl group, a substituted or unsubstituted C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉).

In an embodiment, R₁₀and R₂₀may each independently be:

a C₁-C₂₀alkyl group, a C₁-C₂₀alkylthio group, or a C₁-C₂₀alkoxy group, each independently 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, or a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrimidinyl group, each independently 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrimidinyl group; or

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

wherein Q₁to Q₉may each independently be:

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

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, or a naphthyl group, each independently substituted with at least one of deuterium, a C₁-C₁₀alkyl group, or a phenyl group.

In an embodiment, R₁₀and R₂₀may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkylthio group, or a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group, a C₁-C₂₀alkylthio group, or a C₁-C₂₀alkoxy group, each independently substituted with at least one of 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 phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, or a triazinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl 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 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a phenoxazinyl group, a phenothiazinyl group, an imidazopyrimidinyl group, or an imidazopyridinyl group, each independently substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an am idino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a phenoxazinyl group, or a phenothiazinyl group.

In an embodiment, R₁₀and R₂₀may each independently be deuterium, —F, a cyano group, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, groups represented by Formulae 9-1 to 9-19, or groups represented by Formulae 10-1 to 10-211:

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wherein, in Formulae 9-1 to 9-19 and 10-1 to 10-211, * indicates a binding site to an adjacent atom, “Ph” represents a phenyl group, and “TMS” represents a trimethylsilyl group.

In an embodiment, R₁₀and R₂₀may each independently be: hydrogen, deuterium, —F, a cyano group, —CD₃, —CD₂H, —CDH₂, —CF₃, —CFH₂, a C₁-C₂₀alkyl group, a C₁-C₂₀alkylthio group, or a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group, a C₁-C₂₀alkylthio group, or a C₁-C₂₀alkoxy group, each independently substituted with at least one of deuterium, a cyano group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a phenoxazinyl group, or a phenothiazinyl group, each independently substituted with at least one of deuterium, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

In an embodiment, R₁₀may be: deuterium, —F, a cyano group, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a C₁-C₂₀alkyl group, a C₁-C₂₀alkylthio group, or a C₁-C₂₀alkoxy group;

a biphenyl group, a terphenyl group, a naphthyl group, a carbazole group, a dibenzofuranyl group, or a dibenzothiophenyl group.

In an embodiment, R₂₀may be hydrogen, deuterium, —F, a cyano group, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a C₁-C₂₀alkyl group, or a phenyl group.

In Formula 1, substituents L₁₀, R₁₀, and R₂₀are present on each ring through which the bond with the corresponding substituent passes.

In Formula 1, b10 and b20 may each independently be an integer from 1 to 8. When b10 is 2 or greater, at least two R₁₀(s) may be identical to or different from each other. When b20 is 2 or greater, at least two R₂₀(s) may be identical to or different from each other.

In an embodiment, b10 and b20 may each independently be 1, 2, 3, or 4.

In an embodiment, b10 may be 1.

In an embodiment, b20 may be 1.

In Formula 1, c10 may be an integer from 1 to 9. When c10 is 2 or greater, at least two -[(L₁₀)_a10-(R₁₀)_b10] group(s) may be identical to or different from each other.

In an embodiment, c10 may be 1, 2, 3, or 4.

In an embodiment, c10 may be 1 or 2.

In an embodiment, c10 may be 1.

In Formula 1, a sum of b20 and c10 may be 9.

In an embodiment, the silane compound represented by Formula 1 may be represented by one of Formulae 10-1 to 10-5:

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wherein, in Formulae 10-1 to 10-5,

descriptions of Ar₁to Ar₃, L₁₀, a10, and R₁₀may respectively be understood by referring to the descriptions of Ar₁to Ar₃, L₁₀, a10, and R₁₀provided herein, and

R₁to R₉may each independently be understood by referring to the description of R₂₀provided herein.

In an embodiment, the silane compound represented by Formula 1 may be a compound represented by Formula 10-5.

In an embodiment, in Formulae 10-1 to 10-5, R₁₀may be: a C₁-C₂₀alkyl group, a C₁-C₂₀alkylthio group, or a C₁-C₂₀alkoxy group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each independently substituted with at least one of deuterium, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

In an embodiment, the silane compound may be one of Compounds 1 to 160:

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When the silane compound represented by Formula 1 may have an asymmetric structure, it may have a low crystallinity of a material. In an embodiment, as intermolecular close packing of the silane compound represented by Formula 1 may be prevented, the silane compound may have relatively excellent or improved amorphous thin film characteristics.

As described above, the silane compound represented by Formula 1 may have suitable electrical characteristics for a material for organic light-emitting devices, e.g., a host material, a hole transport material, and an electron transport material in an emission layer. In an embodiment, an organic light-emitting device including the silane compound may have high or improved efficiency and/or a long or improved lifespan.

In an embodiment, the silane compound represented by Formula 1 may satisfy Equation 1:

E(T1)<E(S1)<2×E(T1) Equation 1

wherein, in Equation 1,

E(T1) indicates a lowest excited triplet energy level of the silane compound, and E(S1) indicates a lowest excited singlet energy level of the silane compound.

In an embodiment, the silane compound represented by Formula 1 may satisfy Equation 2:

[2×E(T1)]−E(S1)<1 eV Equation 2

wherein, in Equation 2,

E(T1) indicates a lowest excited triplet energy level of the silane compound, and E(S1) indicates a lowest excited singlet energy level of the silane compound.

While not wishing to be bound by theory, it is understood that when the silane compound represented by Formula 1 may satisfy Equation 1 and/or Equation 2, a triplet-triplet fusion (TTF) phenomenon, in which triplet excitons may be fused to thereby form singlet excitons, may occur. Thus, when the silane compound is applied to an organic light-emitting device, fluorescent emission may occur from the produced singlet excitons due to such a TTF phenomenon, and thus, the organic light-emitting device may have improved luminescence efficiency and lifespan.

In an embodiment, the silane compound represented by Formula 1 may satisfy Equation 2-1:

[2×E(T1)]−E(S1)<0.5 eV Equation 2-1

wherein, in Equation 2-1,

E(T1) indicates a lowest excited triplet energy level of the silane compound, and E(S1) indicates a lowest excited singlet energy level of the silane compound.

A method of synthesizing the silane compound represented by Formula 1 may be apparent to one of ordinary skill in the art by referring to Synthesis Examples provided herein.

The silane compound represented by Formula 1 may be suitable for use as an organic layer material of an organic light-emitting device, for example, an emission layer material, a hole transport region material, and/or an electron transport region material of the organic layer. According to an aspect of an embodiment, an organic light-emitting device may include: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer and at least one of the silane compound represented by Formula 1.

As the organic light-emitting device has an organic layer including the silane compound represented by Formula 1, the organic light-emitting device may have a low driving voltage, high or improved efficiency, high or improved luminance, high or improved quantum efficiency, and long or improved lifespan.

In an embodiment, in the organic light-emitting device,

the first electrode may be an anode, the second electrode may be a cathode,

the organic layer may include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,

wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and

the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof, but embodiments are not limited thereto.

In an embodiment, the emission layer in the organic light-emitting device may include at least one of the silane compounds represented by Formula 1.

In an embodiment, the emission layer in the organic light-emitting device may include a host and a dopant, wherein the host may include at least one of the silane compound represented by Formula 1, and the dopant may include a phosphorescent dopant or a fluorescent dopant. In an embodiment, the dopant may include a phosphorescent dopant (e.g., an organometallic compound represented by Formula 81 provided herein). The host may further include any suitable host, in addition to the silane compound represented by Formula 1.

The emission layer may emit red light, green light, or blue light.

In an embodiment, the emission layer may include a fluorescent dopant, but embodiments are not limited thereto.

In an embodiment, the emission layer may include a phosphorescent dopant, but embodiments are not limited thereto.

In an embodiment, the silane compound represented by Formula 1 may be included in a hole transport region of the organic light-emitting device.

In an embodiment, a hole transport region of the organic light-emitting device may include at least one of a hole injection layer, a hole transport layer, or an electron blocking layer, wherein at least one of the hole injection layer, the hole transport layer, or the electron blocking layer may include the silane compound represented by Formula 1.

In an embodiment, the silane compound represented by Formula 1 may be included in an electron transport region of the organic light-emitting device.

In an embodiment, an electron transport region of the organic light-emitting device may include at least one of a hole blocking layer, an electron transport layer, or an electron injection layer, wherein at least one of the hole blocking layer, the electron transport layer, or the electron injection layer, may include the silane compound represented by Formula 1.

In an embodiment, a hole transport region of the organic light-emitting device may include an electron blocking layer, wherein the electron blocking layer may include the silane compound represented by Formula 1. The electron blocking layer may be in a direct contact with the emission layer.

In an embodiment, an electron transport region of the organic light-emitting device may include a hole blocking layer, wherein the hole blocking layer may include the silane compound represented by Formula 1. The hole blocking layer may be in a direct contact with the emission layer.

In an embodiment, an organic light-emitting device may include: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode and including an emission layer,

wherein the emission layer may include a host and a dopant, and

the host may include at least one silane compound represented by Formula 1.

In an embodiment, a content of the host may be greater than a content of the dopant in the emission layer in the organic light-emitting device.

In an embodiment, the host in the emission layer in the organic light-emitting device may consist of the silane compound.

In an embodiment, a ratio of emission components emitted from the dopant may be 80% or greater of the whole emission components emitted from the emission layer of the organic light-emitting device.

In an embodiment, the dopant in the emission layer in the organic light-emitting device may be a fluorescent dopant.

For example, the fluorescent dopant may be a condensed polycyclic compound or a styryl-based compound.

For example, the fluorescent dopant may include 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 are not limited thereto:

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In an embodiment, the fluorescent dopant may be a styryl-amine-based compound or a styryl-carbazole-based compound, but embodiments are not limited thereto.

In an embodiment, the fluorescent 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 group, an indenoanthracene group, a tetracene group, a bisanthracene group, or a group represented by one of Formulae 501-1 to 501-18, each independently substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an am idino 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 C₁-C₆₀alkylthio 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 C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or —Si(Q₅₀₁)(Q₅₀₂)(Q₅₀₃) (wherein Q₅₀₁to Q₅₀₃may each independently be hydrogen, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a C₁-C₆₀alkylthio group, a C₆-C₆₀aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group),

L₅₀₁to L₅₀₃may each independently be a substituted or unsubstituted cycloalkylene 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 independently substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio 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, or a dibenzothiophenyl group,

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

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

In an embodiment, 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 Formulae 501-1 to 501-18, each independently substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio 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, or —Si(Q₅₀₁)(Q₅₀₂)(Q₅₀₃) (wherein Q₅₀₁to Q₅₀₃may each independently be hydrogen, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group),

L₅₀₁to L₅₀₃may each be understood by referring to the description of L₁₀provided herein,

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

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

In an embodiment, the fluorescent 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], X₅₈may be N or C-[(L₅₀₈)_xd8−R₅₀₈],

L₅₀₁to L₅₀₈may each be understood by referring to the description of L₅₀₁in Formula 501,

xd1 to xd8 may each be understood by referring to the description of xd1 in Formula 501,

R₅₀₁to R₅₀₈may each independently be:

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

two of R₅₀₁to R₅₀₄may optionally be bound to form a saturated or unsaturated ring,

two of R₅₀₅to R₅₀₈may optionally be bound to form a saturated or unsaturated ring, and

wherein in Formulae 502-2 to 502-5, substituents L₅₀₁, L₅₀₂, R₅₀₁, and R₅₀₂are present on each ring through which the bond with the corresponding substituent passes.

The fluorescent dopant may include, for example, Compounds FD(1) to FD(16) or FD1 to FD13:

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In an embodiment, the emission layer in the organic light-emitting device may further include a phosphorescent dopant, in addition to the silane compound represented by Formula 1.

For example, the phosphorescent dopant may include an organometallic compound represented by Formula 81:

M(L₈₁)_n81(L₈₂)_n82 Formula 81

wherein L₈₁may be a ligand represented by Formula 81A,

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wherein, in Formulae 81 and 81A,

M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh),

n81 may be an integer from 1 to 3; and when n81 is 2 or greater, at least two L₈₁(s) may be identical to or different from each other,

L₈₂may be an organic ligand, n82 may be an integer from 0 to 4; and when n82 is 2 or greater, at least two L₈₂(s) may be identical to or different from each other,

Y₈₁to Y₈₄may each independently be carbon (C) or nitrogen (N),

Y₈₁and Y₈₂may be linked to each other via a single bond or a double bond, and Y₈₃and Y₈₄are linked to each other via a single bond or a double bond,

CY₈₁and CY₈₂may each independently be a C₅-C₃₀carbocyclic group or a C₂-C₃₀heterocyclic group,

CY₈₁and CY₈₂may optionally be bound via an organic linking group,

R₈₁to R₈₅may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF₅, 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 C₁-C₆₀alkylthio 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 C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₈₁)(Q₈₂)(Q₈₃), —N(Q₈₄)(Q₈₅), —B(Q₈₈)(Q₈₇), or —P(═O)(Q₈₈)(Q₈₉),

a81 to a83 may each independently be an integer from 0 to 5,

when a81 is 2 or greater, at least two R₈₁(s) may be identical to or different from each other,

when a82 is 2 or greater, at least two R₈₂(s) may be identical to or different from each other,

when a81 is 2 or greater, two adjacent R₈₁(s) may be optionally bound to form a saturated or unsaturated C₂-C₃₀ring (e.g., a benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a bicyclo[2.2.1]heptane ring, a naphthalene ring, a benzoindene ring, a benzoindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring), or a saturated or unsaturated C₂-C₃₀ring substituted with at least one R₈₈(e.g., a benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a bicyclo[2.2.1]heptane ring, a naphthalene ring, a benzoindene ring, a benzoindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring, each independently substituted with at least one R₈₈),

when a82 is 2 or greater, two adjacent R₈₂(s) may be optionally bound to form a saturated or unsaturated C₂-C₃₀ring (e.g., a benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a bicyclo[2.2.1]heptane ring, a naphthalene ring, a benzoindene ring, a benzoindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring), or a saturated or unsaturated C₂-C₃₀ring substituted with at least one R₈₉(e.g., a benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a bicyclo[2.2.1]heptane ring, a naphthalene ring, a benzoindene ring, a benzoindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring, each independently substituted with at least one R₈₉),

R₈₈may be understood by referring to the description of R₈₁provided herein,

R₈₉may be understood by referring to the description of R₈₂provided herein,

* and *′ in Formula 81A each indicate a binding site to M in Formula 81, and at least one substituent of the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₁-C₆₀alkylthio group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted C₁-C₆₀heteroaryloxy group, the substituted C₁-C₆₀heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be: 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 C₁-C₆₀alkylthio 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 C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or —Si(Q₉₁)(Q₉₂)(Q₉₃),

wherein Q₈₁to Q₈₉and Q₉₁to Q₉₃may each independently be hydrogen, deuterium, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a C₁-C₆₀alkylthio group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.

In an embodiment, in Formula 81A,

a83 may be 1 or 2, and

R₈₃to R₈₅may each independently be:

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, or a naphthyl group; or an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, or a naphthyl group, each independently substituted with at least one of deuterium, a C₁-C₁₀alkyl group, or a phenyl group, but embodiments are not limited thereto.

In an embodiment, in Formula 81A,

Y₈₁may be N, Y₈₂and Y₈₃may each be C, Y₈₄may be N or C, and

CY₈₁and CY₈₂may each independently be a cyclopentadiene group, a phenyl 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 pentacene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, an isoindole group, an indole group, an indazole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a purine group, a furan group, a thiophene group, a pyridine group, a pyrimidine 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, a benzofuran group, a benzothiophene group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a benzocarbazole group, a dibenzocarbazole group, an imidazopyridine group, an imidazopyrimidine group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, or a 2,3-dihydro-1H-imidazole group.

In an embodiment, in Formula 81A, Y₈₁may be N, Y₈₂to Y₈₄may each be C, CY₈₁may be 5-membered rings including two N atoms as ring-forming atoms, and CY₈₂may be a phenyl group, a naphthalene group a fluorene group, a dibenzofuran group, or a dibenzothiophene group, but embodiments are not limited thereto.

In an embodiment, in Formula 81A, Y₈₁may be N, Y₈₂to Y₈₄may each be C, CY₈₁may be an imidazole group or a 2,3-dihydro-1H-imidazole group, and CY₈₂may be a phenyl group, a naphthalene group a fluorene group, a dibenzofuran group, or a dibenzothiophene group, but embodiments are not limited thereto.

In an embodiment, in Formula 81A,

Y₈₁may be N, Y₈₂to Y₈₄may each be C,

CY₈₁may be a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a pyridine group, a pyrimidine 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 benzimidazole group, an iso-benzothiazole group, a benzoxazole group, or an isobenzoxazole group, or

CY₈₂may be a cyclopentadiene group, a phenyl group, a naphthalene group, a fluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a triphenylene group, a pyrene group, a chrysene group, a perylene 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, or a dibenzosilole group.

In an embodiment, in Formula 81A,

R₈₁and R₈₂may each independently be:

—B(Q₈₆)(Q₈₇) or —P(═O)(Q₈₈)(Q₈₉),

wherein Q₈₆to Q₈₉may each independently be:

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, or a naphthyl group; or an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, or a naphthyl group, each independently substituted with at least one of deuterium, a C₁-C₁₀alkyl group, or a phenyl group.

In an embodiment, in Formula 81A, at least one of R₈₁(s) in the number of a81 and R₈₂(s) in the number of a82 may be a cyano group.

In an embodiment, in Formula 81A, at least one of R₈₂(s) in the number of a82 may be a cyano group.

In an embodiment, in Formula 81A, at least one of R₈₁(s) in the number of a81 and R₈₂(s) in the number of a82 may be deuterium.

In an embodiment, in Formula 81, L₈₂may be ligands represented by Formulae 3-1(1) to 3-1(69), 3-1(71) to 3-1(79), 3-1(81) to 3-1(88), 3-1(91) to 3-1(98), and 3-1(101) to 3-1(114):

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wherein, in Formulae 3-1(1) to 3-1(69), 3-1(71) to 3-1(79), 3-1(81) to 3-1(88), 3-1(91) to 3-1(98), and 3-1(101) to 3-1(114),

X₁may be O, S, C(Z₂₁)(Z₂₂), or N(Z₂₃),

X₃₁may be N or C(Z_1a), X₃₂may be N or C(Z_1b),

X₄₁may be O, S, N(Z_1a), or C(Z_1a)(Z_1b),

Z₁to Z₄, Z_1a, Z_1b, Z_1c, Z_1d, Z_2a, Z_2b, Z_2c, Z_2d, Z₁₁to Z₁₄, and Z₂₁to Z₂₃may each independently be:

—B(Q₈₆)(Q₈₇) or —P(═O)(Q₈₈)(Q₈₉),

wherein Q₈₈to Q₈₉may each independently be:

d2 and e2 may each independently be 0 or 2,

e3 may be an integer from 0 to 3,

d4 and e4 may each independently be an integer from 0 to 4,

d6 and e6 may each independently be an integer from 0 to 6,

d8 and e8 may each independently be an integer from 0 to 8, and

* and *′ each indicate a binding site to M in Formula 1.

In an embodiment, in Formula 81, M may be Ir, and a sum of n81 and n82 may be 3. In an embodiment, in Formula 81, M may be Pt, and a sum of n81 and n82 may be 2.

In an embodiment, the organometallic compound represented by Formula 81 may be neutral and may not include ion pairs of cations and anions.

In an embodiment, the organometallic compound represented by Formula 81 may include at least one of Compounds PD1 to PD78 or FIr₆, but embodiments are not limited thereto:

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In an embodiment, the emission layer in the light-emitting device may emit blue light having a maximum emission wavelength in a range of about 410 nanometers (nm) to about 490 nm.

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

For example, Compound 1 may only be included as the silane compound in the organic layer. In an embodiment, Compound 1 may be included in the emission layer of the organic light-emitting device. In an embodiment, the organic layer may include Compounds 1 and 2 as the silane compounds. In an embodiment, Compounds 1 and 2 may be present in the same layer (for example, Compounds 1 and 2 may be both present in an emission layer), or in different layers (for example, Compound 1 may be present in an emission layer, and Compound 2 may be present in a hole blocking layer).

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

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

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

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

The first electrode 11 may be formed by depositing or sputtering, onto the substrate, a material for forming the first electrode 11. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be materials with a high work function for easy hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), or zinc oxide (ZnO). In an embodiment, the material for forming the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).

The first electrode 11 may have a single-layered structure or a multi-layered structure including a plurality of layers. In an embodiment, the first electrode 11 may have a triple-layered structure of ITO/Ag/ITO, but embodiments are not limited thereto.

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

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

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

The hole transport region may include at least one of a hole injection layer, a hole transport layer, an electron blocking layer, or a buffer layer.

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

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

When a hole injection layer is formed by vacuum-deposition, for example, the vacuum deposition may be performed at a temperature in a range of about 100° C. to about 500° C., at a vacuum degree in a range of about 10⁻⁸torr to about 10⁻³torr, and at a rate in a range of about 0.01 Angstroms per second (Å/sec) to about 100 Å/sec, though the conditions may vary depending on a compound used as a hole injection material and a structure and thermal properties of a desired hole injection layer, but embodiments are not limited thereto.

When a hole injection layer is formed by spin coating, the spin coating may be performed at a rate in a range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and at a temperature in a range of about 80° C. to 200° C. to facilitate removal of a solvent after the spin coating, though the conditions may vary depending on a compound used as a hole injection material and a structure and thermal properties of a desired hole injection layer, but embodiments are not limited thereto.

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

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

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wherein, in Formula 201, Ar₁₀₁and Ar₁₀₂may each independently be:

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

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

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group (e.g., a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group), a C₁-C₁₀alkoxy group (e.g., a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group), or a C₁-C₁₀alkylthio group (e.g., a thiomethyl group, a thioethyl group, a thiopropyl group, a thiobutyl group, a thiopentyl group, or a thiohexyl group);

a C₁-C₁₀alkyl group, a C₁-C₁₀alkylthio group, or a C₁-C₁₀alkoxy group, each independently substituted with at least one of 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, or a phosphoric acid group or a salt thereof;

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

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each independently substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a C₁-C₁₀alkylthio group, or a C₁-C₁₀alkoxy group, but embodiments are not limited thereto.

In Formula 201, R₁₀₉may be:

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

a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each independently substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio group, a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group.

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

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

In an embodiment, the compounds represented by Formulae 201 and 202 may include Compounds HT1 to HT20, but embodiments are not limited thereto:

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The thickness of the hole transport region may be in a range of about 100 Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000 Å, about 100 Å to about 2,000 Å, about 100 Å to about 3,000 Å, about 100 Å to about 4,000 Å, about 100 Å to about 5,000 Å, about 100 Å to about 6,000 Å, about 100 Å to about 7,000 Å, about 100 Å to about 8,000 Å, or about 100 Å to about 9,000 Å. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, 100 Å to about 2,000 Å, about 100 Å to about 3,000 Å, about 100 Å to about 4,000 Å, about 100 Å to about 5,000 Å, about 100 Å to about 6,000 Å, about 100 Å to about 7,000 Å, about 100 Å to about 8,000 Å, or about 100 Å to about 9,000 Å. The thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å, about 100 Å to about 1,000 Å, about 100 Å to about 500 Å, about 50 Å to about 1,500 Å, about 50 Å to about 1,000 Å, or about 50 Å to about 500 Å. While not wishing to be bound by theory, it is understood that when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, excellent or improved hole transport characteristics may be obtained without a substantial increase in driving voltage.

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

The charge generating material may include, for example, a p-dopant. The p-dopant may include one of a quinone derivative, a metal oxide, and a compound containing a cyano group, but embodiments are not limited thereto. For example, non-limiting examples of the p-dopant include a quinone derivative, such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenum oxide; and a compound containing a cyano group, such as Compound HT-D1 or Compound HT-D2, but embodiments are not limited thereto:

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The hole transport region may further include a buffer layer.

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

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

The hole transport region may further include an electron blocking layer. The electron blocking layer may include any suitable material, e.g., mCP, but embodiments are not limited thereto:

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The thickness of the electron blocking layer may be in a range of about 50 Å to about 1,000 Å, and in some embodiments, about 70 Å to about 500 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron blocking layer is within any of these ranges, excellent or improved electron blocking characteristics may be obtained without a substantial increase in driving voltage.

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

The emission layer may include the silane compound represented by Formula 1.

In an embodiment, the emission layer may include the silane compound represented by Formula 1 only.

In an embodiment, the emission layer may include

the silane compound represented by Formula 1 and

i) a second compound as a host which is different from the silane compound represented by Formula 1;

ii) the organometallic compound represented by Formula 81; or

iii) any combination of i) and ii).

The silane compound represented by Formula 1, the second compound, and the organometallic compound represented by Formula 81 may respectively be understood by referring to the descriptions for those provided herein. The second compound may be any suitable host used in an organic light emitting device available in the art.

When the emission layer includes the host and the dopant, an amount of the dopant may be selected from a range of about 0.01 parts to about 20 parts by weight based on about 100 parts by weight of the emission layer, but embodiments are not limited thereto. For example, the amount of the dopant may be from a range of about 0.01 parts to about 20 parts, about 0.01 parts to about 15 parts, about 0.01 parts to about 10 parts, about 0.01 parts to about 7 parts, about 0.01 parts to about 5 parts, about 0.01 parts to about 3 parts, about 0.01 parts to about 1 parts, or about 0.01 parts to about 0.5 parts by weight based on about 100 parts by weight of the emission layer, but embodiments are not limited thereto. While not wishing to be bound by theory, it is understood that when the amount of the dopant is within this range, light emission without quenching may be realized.

When the emission layer includes the silane compound represented by Formula 1 and the second compound, a weight ratio of the silane compound represented by Formula 1 to the second compound may be in a range of about 1:99 to about 99:1, for example, about 90:10 to about 10:90, about 80:20 to about 20:80, about 70:30 to about 30:70, or about 60:40 to about 40:60. In an embodiment, a weight ratio of the silane compound represented by Formula 1 to the second compound may be in a range of about 60:40 to about 40:60. While not wishing to be bound by theory, it is understood that when the weight ratio of the silane compound represented by Formula 1 to the second compound in the emission layer is within any of these ranges, the charge transport balance may be efficiently achieved in the emission layer.

The thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, and in an embodiment, about 200 Å to about 600 Å. While not wishing to be bound by theory, it is understood that when the thickness of the emission layer is within any of these ranges, improved luminescence characteristics may be obtained without a substantial increase in driving voltage.

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

The electron transport region may include at least one of a hole blocking layer, an electron transport layer, or an electron injection layer.

In an embodiment, the electron transport region may have a hole blocking layer/an electron transport layer/an electron injection layer structure or an electron transport layer/an electron injection layer structure, but embodiments are not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.

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

When the electron transport region includes a hole blocking layer, the hole blocking layer, for example, may include at least one of BCP or Bphen, but embodiments are not limited thereto:

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The hole blocking layer may include the silane compound represented by Formula

The thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, about 40 Å to about 400 Å, about 50 Å to about 500 Å, about 60 Å to about 600 Å, about 70 Å to about 700 Å, about 80 Å to about 800 Å, about 90 Å to about 900 Å, or about 100 Å to about 1000 Å. While not wishing to be bound by theory, it is understood that when the thickness of the hole blocking layer is within any of these ranges, excellent or improved hole blocking characteristics may be obtained without a substantial increase in driving voltage.

The electron transport layer may include at least one of BCP, Bphen, Alq₃, BAlq, TAZ, or NTAZ:

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In an embodiment, the electron transport layer may include at least one of Compounds ET1, ET2, or ET3, but embodiments are not limited thereto:

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The thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, and in an embodiment, about 150 Å to about 500 Å, about 200 Å to about 600 Å, about 300 Å to about 700 Å, about 400 Å to about 800 Å, about 500 Å to about 900 Å, or about 600 Å to about 1000 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron transport layer is within any of these ranges, excellent or improved electron transport characteristics may be obtained without a substantial increase in driving voltage.

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

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

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

The electron injection layer may include at least one of LiQ, LiF, NaCl, CsF, Li₂O, or BaO.

The thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and in an embodiment, about 3 Å to about 90 Å, about 10 Å to about 80 Å, about 20 Å to about 70 Å, about 30 Å to about 60 Å, or about 40 Å to about 50 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron injection layer is within any of these ranges, excellent or improved electron injection characteristics may be obtained without a substantial increase in driving voltage.

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

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

DEFINITION 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. Examples thereof include a methyl group, an ethyl group, a propyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. The term “C₁-C₆₀alkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₆₀alkyl group.

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

The term “C₁-C₆₀alkylthio group” used herein refers to a monovalent group represented by-SA₁₀₄(wherein A₁₀₄is the C₁-C₆₀alkyl group), and examples thereof include a thiomethyl group, a thioethyl group, and a thioisopropyl group.

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

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

The term “C₃-C₁₀cycloalkyl group” as used herein refers to a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms. 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 (e.g. C₂-C₁₀heterocycloalkenyl group)” as used herein refers to a monovalent monocyclic group including at least one heteroatom of N, O, P, Si, or S as a ring-forming atom and 1 to 10 carbon atoms. 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 its ring, wherein the molecular structure as a whole is non-aromatic. Examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

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

The term “C₆-C₆₀aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. The term “C₆-C₆₀arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C₆-C₆₀aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀aryl group and the C₆-C₆₀arylene group each include a plurality of rings, the plurality of rings may be fused to each other. The term “C₇-C₆₀alkyl aryl group” as used herein refers to a C₆-C₆₀aryl group substituted with at least one C₁-C₆₀alkyl group.

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom N, O, P, Si, or S as a ring-forming atom and 1 to 60 carbon atoms. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom N, O, P, Si, or S as a ring-forming atom and 1 to 60 carbon atoms. Examples of the C₁-C₆₀heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀heteroarylene group each include a plurality of rings, the plurality of rings may be fused to each other. The term “C₂-C₆₀alkyl heteroaryl group” as used herein refers to a C₁-C₆₀heteroaryl group substituted with at least one C₁-C₆₀alkyl group.

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

The term “C₁-C₆₀heteroaryloxy group” as used herein refers to-OA₁₀₅(wherein A₁₀₅is the C₁-C₆₀heteroaryl group), and the term “C₁-C₆₀heteroarylthio group” as used herein indicates-SA₁₀₆(wherein A₁₀₆is the C₁-C₆₀heteroaryl group).

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

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

The term “C₅-C₃₀carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group including 5 to 30 carbon atoms only as ring-forming atoms. The C₅-C₃₀carbocyclic group may be a monocyclic group or a polycyclic group.

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

At least one substituent of the substituted C₅-C₃₀carbocyclic group, the substituted C₁-C₃₀heterocyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₁-C₆₀alkylthio group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₇-C₆₀alkyl aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted C₁-C₆₀heteroaryloxy group, the substituted C₁-C₆₀heteroarylthio group, the substituted C₂-C₆₀alkyl heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, or the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkylthio group, or a C₁-C₆₀alkoxy group;

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkylthio group, or a C₁-C₆₀alkoxy group, each independently 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₇-C₆₀alkyl aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a C₂-C₆₀alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), or —P(═O)(Q₁₈)(Q₁₉);

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₇-C₆₀alkyl aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a C₂-C₆₀alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each independently 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 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 C₁-C₆₀alkylthio group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₇-C₆₀alkyl aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a C₂-C₆₀alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), or —P(═O)(Q₂₈)(Q₂₉), or

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

wherein Q₁to Q₉, Q₁₁to Q₁₉, Q₂₁to Q₂₉, and Q₃₁to Q₃₉may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₁-C₆₀alkyl group substituted with at least one of deuterium, a C₁-C₆₀alkyl group, or a C₆-C₆₀aryl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₁-C₆₀alkylthio 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 of deuterium, a C₁-C₆₀alkyl group, or a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a heteroaryloxy group, a C₁-C₆₀heteroarylthio group, a C₂-C₆₀alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.

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

EXAMPLES
Synthesis Example 1: Synthesis of Compound 10

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9-bromo-10-phenylanthracene (1.0 equivalents (eq.)), triphenyl silylacetylene (2.0 eq.), bis(triphenyl phosphine) palladium(II) dichloride (Pd(PPh₃)₂C₁₂) (0.1 eq.), copper(I) iodide (CuI) (0.11 eq.), and piperidine (8.0 eq.) were added to a reaction vessel, followed by purging with nitrogen. Then, triethylamine (Et₃N) was used as a solvent to perform heating under reflux for 20 hours. A saturated ammonium chloride solution was added thereto, followed by extraction using dichloromethane. After drying with anhydrous magnesium sulfate, a solvent was removed therefrom, and purification through column chromatography and recrystallization (using ethyl acetate and hexane) were performed, to thereby obtain a white solid of Compound 10. Yield: 32%, LCMS[M+H, m/z] 537.2

Synthesis Example 2: Synthesis of Compound 24

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Compound 24 was synthesized in substantially the same manner as in Synthesis Example 1, except that 9-bromo-10-(naphthalen-1-yl)anthracene was used instead of 9-bromo-10-phenylanthracene, and dibenzo[b,d]furan-2-yl(ethynyl)diphenyl silane was used instead of triphenyl silylacetylene. Yield: 35%, LCMS[M+H, m/z] 677.2

Synthesis Example 3: Synthesis of Compound 51

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Compound 51 was synthesized in substantially the same manner as in Synthesis Example 1, except that 9-bromo-10-(naphthalen-1-yl)anthracene was used instead of 9-bromo-10-phenylanthracene. Yield: 32%, LCMS[M+H, m/z] 587.2

Synthesis Example 4: Synthesis of Compound 56

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Compound 56 was synthesized in substantially the same manner as in Synthesis Example 1, except that 2-(10-bromoanthracen-9-yl)dibenzo[b,d]furan was used instead of 9-bromo-10-phenylanthracene. Yield: 35%, LCMS[M+H, m/z] 627.2

Example 1

A patterned ITO glass substrate (50 millimeters (mm)×50 mm×0.7 mm) was sonicated in acetone, isopropyl alcohol, and distilled water for 20 minutes each, and heat-treated for 20 minutes at 250° C.

Thereafter, a hole injection layer was formed to have a thickness of about 100 Å on the ITO electrode (anode) on the glass substrate by depositing HATCN at a rate of 1 Å/sec. A hole transport layer was formed to have a thickness of about 800 Å on the hole injection layer by depositing NPB at a rate of 1 Å/sec.

Then, an electron blocking layer was formed to have a thickness of 50 Å on the hole transport layer by depositing mCP at a rate of 1 Å/sec.

An emission layer was formed to have a thickness of 200 Å on the electron blocking layer by co-depositing Compound 10 (as a host) and Compound D1 (as a dopant) at a deposition rate of 0.97 Å/sec and 0.3 Å/sec, respectively.

An electron transport layer was formed to have a thickness of 300 Å by depositing DPEPO and LiQ (1:1) on the emission layer at a deposition rate of 0.5 Å/sec. An electron injection layer was formed to have a thickness of 10 Å by depositing LiQ on the electron transport layer at a deposition rate of 0.5 Å/sec. A second electrode (cathode) was formed to have a thickness of 1,000 Å by vacuum-depositing aluminum (Al) on the electron injection layer, thereby completing the manufacture of an organic light-emitting device having a structure of ITO/HATCN (100 Å)/NPB (800 Å)/mCP (50 Å)/Compound 10+Compound D1 (3 vol %) (200 Å)/DPEPO:LiQ (300 Å)/LiQ (10 Å)/Al (1,000 Å).

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Examples 2 to 4

Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of Compound 10 as a host in the formation of an emission layer.

Comparative Examples 1 and 2

Organic light-emitting devices were manufactured in the same manner as in Example 1, except that Compound A or Compound 10 was used as a single light-emitting material as shown in Table 1.

Evaluation Example 1: Evaluation of Characteristics of Organic Light-Emitting Device

The external quantum efficiency (EQE), a TTF ratio, and lifespan (T97) of the organic light-emitting devices of Examples 1 to 4 and Comparative Examples 1 and 2 were evaluated in relative values. The results thereof are shown in Table 1. A Keithley 2400 current voltmeter and a luminance meter (Minolta Cs-1000A) were used for the evaluation. The lifespan (T₉₇) refers to time required for the luminance of the organic light-emitting device to reduce from the initial luminance to 97% thereof. The TTF ratio was measured as a y-intercept value reciprocal squared value in the graph of 1/square root of the TrEL Intensity (1/sqrt (TrEL))−time, in which the decay of transient electroluminescence (TrEL) was measured from 500 nanoseconds (ns) to 4,000 ns. In Table 1, “N.D.” indicates “not detected”.

TABLE 1

Life-

Driving

span

Emission
Emission
voltage
EQE
(T₉₇)
TTF

layer
layer
(relative
(relative
(relative
ratio

No.
Host
Dopant
value)
value)
value)
(%)

Example 1
Compound
Compound
100
100
100
40.5

10
D1

Example 2
Compound
Compound
104.9
148.9
66.9
34.2

24
D1

Example 3
Compound
Compound
102.3
159.2
106.3
34.2

51
D1

Example 4
Compound
Compound
103.4
164.7
99.9
35.4

56
D1

Compar-
—
Compound
116.4
97.6
0.5
N.D.

ative

A

Example 1

Compar-
—
Compound
105.5
110.3
2.0
N.D.

ative

10

Example 2

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As shown in Table 1, the organic light-emitting devices of Examples 1 to 4 were each found to have a low driving voltage, an improved or equal level of EQE, significantly excellent or improved lifespan, and a high or improved TTF ratio, as compared with the organic light-emitting devices of Comparative Examples 1 and 2.

As apparent from the foregoing description, the silane compound was found to have excellent or improved electrical characteristics and thermal stability, and an organic light-emitting device including the silane compound as a host was found to have high or improved efficiency, long or improved lifespan, and a high or improved TTF ratio.

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

ORGANIC LIGHT-EMITTING DEVICE

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