Heterocyclic compound, organic light-emitting device including heterocyclic compound, and electronic device including organic light-emitting device

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0170043, filed on Dec. 18, 2019, in the Korean Intellectual Property Office, the entire content of which is incorporated herein by reference.

BACKGROUND
1. Field

One or more aspects of embodiments of the present disclosure relate to a heterocyclic compound, an organic light-emitting device including the heterocyclic compound, and an electronic apparatus including the organic light-emitting device.

2. Description of Related Art

Organic light-emitting devices (OLEDs) are self-emission devices that, as compared with related devices, have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of brightness, driving voltage, and/or response speed, and can produce full-color images.

OLEDs may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state to thereby generate light.

SUMMARY

One or more aspects of embodiments of the present disclosure are directed toward a heterocyclic compound and an organic light-emitting device including the same.

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

According to one or more embodiments, a heterocylic compound may be represented by Formula 1:

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wherein, in Formula 1,

rings A₁₁to A₁₃, rings A₂₁to A₂₃, and rings A₃₁to A₃₃may each independently be a C₅-C₃₀carbocyclic group or a C₂-C₃₀heterocyclic group,

X₁₁may be O, S, N(R_11a), C(R_11a)(R_11b), or Si(R_11a)(R_11b),

X₂₁may be O, S, N(R_21a), C(R_21a)(R_21b), or Si(R_21a)(R_21b),

X₃₁may be O, S, N(R_31a), C(R_31a)(R_31b), or Si(R_31a)(R_31b),

a2 may be 0 or 1, and when a2 is 0, a corresponding boron atom may not be present,

b2 may be 0 or 1, and when b2 is 0, X₂₁may not be present,

c2 may be 0 or 1, and when c2 is 0, ring A₂₃may not be present,

a3 may be 0 or 1, and when a3 is 0, a corresponding boron atom may not be present,

b3 may be 0 or 1, and when b3 is 0, X₃₁may not be present,

c3 may be 0 or 1, and when c3 is 0, ring A₃₃may not be present,

R_11a, R_11b, R_21a, R_21b, R_31a, R_31b, R₁₁to R₁₃, R₂₁to R₂₃, and R₃₁to R₃₃may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

d11 to d13, d21 to d23, and d31 to d33 may each independently be an integer from 0 to 10,

at least two selected from R_11a, R_11b, R_21a, R_21b, R_31a, R_31b, R₁₁to R₁₃, R₂₁to R₂₃, and R₃₁to R₃₃may optionally be bound to form a C₅-C₃₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, or a C₂-C₃₀heterocyclic group that is unsubstituted or substituted with at least one R_10a,

R_10amay be the same as described in connection with R₁₁provided herein, 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 C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group;

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

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

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

wherein Q₁to Q₃, Q₁₁to Q₁₃, Q₂₁to Q₂₃, and Q₃₁to Q₃₃may each independently be selected from: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a C₁-C₆₀alkyl group; a C₂-C₆₀alkenyl group; a C₂-C₆₀alkynyl group; a C₁-C₆₀alkoxy group; a C₃-C₁₀cycloalkyl group; a C₁-C₁₀heterocycloalkyl group; a C₃-C₁₀cycloalkenyl group; a C₁-C₁₀heterocycloalkenyl group; a C₆-C₆₀aryl group; a C₁-C₆₀heteroaryl group; a monovalent non-aromatic condensed polycyclic group; a monovalent non-aromatic condensed heteropolycyclic group; a C₁-C₆₀alkyl group substituted with at least one selected from deuterium, —F, and a cyano group; a C₆-C₆₀aryl group substituted with at least one selected from deuterium, —F, and a cyano group; a biphenyl group; and a terphenyl group.

According to one or more embodiments, an organic light-emitting device may include: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode and including an emission layer; and at least one heterocyclic compound of the present embodiments.

BRIEF DESCRIPTION OF THE DRAWINGS

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

FIG. 1 is a schematic cross-sectional view of an embodiment of an organic light-emitting device;

FIG. 2 is a schematic cross-sectional view of an embodiment of an organic light-emitting device;

FIG. 3 is a schematic cross-sectional view of an embodiment of an organic light-emitting device; and

FIG. 4 is a schematic cross-sectional view of an embodiment of an organic light-emitting device.

DETAILED DESCRIPTION

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

A heterocyclic compound may be represented by Formula 1:

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wherein, in Formula 1, rings A₁₁to A₁₃, rings A₂₁to A₂₃, and rings A₃₁to A₃₃may each independently be a C₅-C₃₀carbocyclic group or a C₂-C₃₀heterocyclic group.

In some embodiments, rings A₁₁to A₁₃, A₂₁to A₂₃, and A₃₁to A₃₃may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophenegroup, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

In one or more embodiments, ring A₁₃may be a benzene group, a naphthalene group, a carbazole group, a fluorene group, a dibenzothiophene group, or a dibenzofuran group.

In one or more embodiments, rings A₁₃, A₂₃, and A₃₃may each independently be a benzene group, a naphthalene group, a carbazole group, a fluorene group, a dibenzothiophene group, or a dibenzofuran group.

In some embodiments, rings A₁₁to A₁₃, A₂₁to A₂₃, and A₃₁to A₃₃may each independently be a benzene group, a naphthalene group, a carbazole group, a fluorene group, a dibenzothiophene group, or a dibenzofuran group.

In some embodiments, rings A₁₁, A₁₂, A₂₁, A₂₂, A₃₁, and A₃₂may each be a benzene group, and rings A₁₃, A₂₃, and A₃₃may each independently be a benzene group, a naphthalene group, a carbazole group, a fluorene group, a dibenzothiophene group, or a dibenzofuran group.

In Formula 1, X₁₁may be O, S, N(R_11a), C(R_11a)(R_11b), or Si(R_11a)(R_11b)X₂₁may be O, S, N(R_21a), C(R_21a)(R_21b), or Si(R_21a)(R_21b), and X₃₁may be O, S, N(R_31a), C(R_31a)(R_31b), or Si(R_31a)(R_31b).

In Formula 1,

a2 may be 0 or 1, and when a2 is 0, a corresponding boron atom may not be present,

b2 may be 0 or 1, and when b2 is 0, X₂₁may not be present,

c2 may be 0 or 1, and when c2 is 0, ring A₂₃may not be present,

a3 may be 0 or 1, and when a3 is 0, a corresponding boron atom may not be present,

b3 may be 0 or 1, and when b3 is 0, X₃₁may not be present, and

c3 may be 0 or 1, and when c3 is 0, ring A₃₃may not be present.

In some embodiments, a2, b2, and c2 may be identical to one another, and a3, b3, and c3 may be identical to one another.

In some embodiments, a2, b2, c2, a3, b3, and c3 may each be 0, or

a2, b2, and c2 may each be 1, and a3, b3, and c3 may each be 0, or

a2, b2, and c2 may each be 0, and a3, b3, and c3 may each be 1, or

a2, b2, c2, a3, b3, and c3 may each be 1.

In an embodiment, in Formula 1, b2 may be 1, and X₁₁may be identical to X₂₁. In some embodiments, in Formula 1, 1) b2 may be 1; and 2) i) X₁₁and X₂₁may both be O or S, or ii) X₁₁may be N(R_11a), and X₂₁may be N(R_21a).

In one or more embodiments, in Formula 1, b2 may be 1, and X₁₁and X₂₁may be different from each other.

In some embodiments, in Formula 1, 1) b2 may be 1; and 2) X₁₁may be O, and X₂₁may be S.

In one or more embodiments, in Formula 1, b2 and b3 may each be 1, and X₁₁, X₂₁, and X₃₁may be identical to one another.

In some embodiments, in Formula 1, 1) b2 and b3 may each be 1; and 2) i) X₂₁, and X₃₁may all be O or S, or ii) X₁₁may be N(R_11a), X₂₁may be N(R_21a), and X₃₁may be N(R_31a).

In one or more embodiments, in Formula 1, b2 and b3 may each be 1, and i) X₁₁may be different from X₂₁, ii) X₂₁may be different from X₃₁, and/or iii) X₃₁may be different from X₁₁.

In some embodiments, in Formula 1, 1) b2 and b3 may each be 1; and 2) may be O, X₂₁may be C(R_21a)(R_21b), and X₃₁may be S.

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

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may be represented by one of Formulae 2-1 to 2-10:

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wherein, in Formulae 2-1 to 2-10,

ring A₁₁, ring A₁₂, X₁₁, R₁₁to R₁₃, d11, and d12 may each independently be the same as described herein,

X₁₂may be O, S, N(R_12a), C(R_12a)(R_12b), or Si(R_12a)(R_12b), wherein R_12aand R_12bmay each independently be the same as described in connection with R_11aand R_11bprovided herein,

e14 may be an integer from 0 to 4,

e16 may be an integer from 0 to 6, and

* and *′ may each indicate a binding site to a carbon atom in a benzene group of Formula 1.

In one or more embodiments, the heterocyclic compound represented by Formula 1 may be represented by one of Formulae 1-1 to 1-3:

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wherein, in Formulae 1-1 to 1-3, rings A₁₁to A₁₃, rings A₂₁to A₂₃, rings A₃₁to A₃₃, X₁₁, X₂₁, X₃₁, R₁₁to R₁₃, R₂₁to R₂₃, R₃₁to R₃₃, d11 to d13, d21 to d23, and d31 to d33 may each independently be the same as described in connection with Formula 1.

In Formulae 1, 2-1 to 2-10, and 1-1 to 1-3, R_11a, R_11b, R_21a, R_21b, R_31a, R_31b, R₁₁to R₁₃, R₂₁to R₂₃, and R₃₁to R₃₃may 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 substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), wherein Q₁to Q₃may respectively be understood by referring to the descriptions of Q₁to Q₃provided herein.

In some embodiments, R_11a, R_11b, R_21a, R_21b, R_31a, R_31b, R₁₁to R₁₃, R₂₁to R₂₃, and R₃₁to R₃₃may each independently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group and a C₁-C₂₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C₁-C₁₀alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, and an azadibenzosilolyl group, each substituted with at least one selected from deuterium, —F, —C, —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 C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomanyl group, a norbomenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C₁-C₁₀alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —P(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂); and

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

wherein Q₁to Q₃and Q₃₁to Q₃₃may each independently be selected from:

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

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group, each independently unsubstituted or substituted with at least one selected from deuterium, a C₁-C₁₀alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group.

In some embodiments, R_11a, R_11b, R_21a, R_21b, R_31a, R_31b, R₁₁to R₁₃, R₂₁to R₂₃, and R₃₁to R₃₃may each independently be selected from:

hydrogen, deuterium, a C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group and a C₁-C₂₀alkoxy group, each substituted with at least one selected from deuterium, —CD₃, —CD₂H, —CDH₂, C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, and a naphthyl group;

wherein Q₁to Q₃and Q₃₁to Q₃₃may each independently be selected from:

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, and a naphthyl group, each independently unsubstituted or substituted with at least one selected from deuterium, a C₁-C₁₀alkyl group, a phenyl group, and a biphenyl group.

In Formula 1, d11 to d13, d21 to d23, and d31 to d33 may each independently indicate the number of R₁₁(s) to R₁₃(s), R₂₁(s) to R₂₃(s), and R₃₁(s) to R₃₃(s). d11 to d13, d21 to d23, and d31 to d33 may each independently be an integer from 0 to 10.

When d11 is 2 or greater, at least two R₁₁(s) may be identical to or different from each other, when d12 is 2 or greater, at least two R₁₂(s) may be identical to or different from each other, and when d13 is 2 or greater, at least two R₁₃(s) may be identical to or different from each other,

when d21 is 2 or greater, at least two R₂₁(s) may be identical to or different from each other, when d22 is 2 or greater, at least two R₂₂(s) may be identical to or different from each other, and when d23 is 2 or greater, at least two R₂₃(s) may be identical to or different from each other, and

when d31 is 2 or greater, at least two R₃₁(s) may be identical to or different from each other, when d32 is 2 or greater, at least two R₃₂(s) may be identical to or different from each other, and when d33 is 2 or greater, at least two R₃₃(s) may be identical to or different from each other.

In Formula 1, at least two selected from R_11a, R_11b, R_21a, R_21b, R_31a, R_31b, R₁₁to R₁₃, R₂₁to R₂₃, and R₃₁to R₃₃may optionally be bound to form a C₅-C₃₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, or a C₂-C₃₀heterocyclic group that is unsubstituted or substituted with at least one R_10a, and

R_10amay be the same as described in connection with R₁₁provided herein.

In an embodiment, the heterocyclic compound may satisfy at least one of Conditions 1 to 3:

Condition 1

X₁₁may be N(R_11a), and

R_11amay be bound to R₁₃to form a C₅-C₃₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, or a C₂-C₃₀heterocyclic group that is unsubstituted or substituted with at least one R_10a;

Condition 2

a2, b2, and c2 may each be 1,

X₂₁may be N(R_21a), and

R_21amay be bound to R₂₃to form a C₅-C₃₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, or a C₂-C₃₀heterocyclic group that is unsubstituted or substituted with at least one R_10a; and

Condition 3

a3, b3, and c3 may each be 1,

X₃₁may be N(R_31a), and

R_31amay be bound to R₃₃to form a C₅-C₃₀carbocyclic group that is unsubstituted or substituted with at least one R_10a, or a C₂-C₃₀heterocyclic group that is unsubstituted or substituted with at least one R_10a.

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

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may be represented by Formula 3-1:

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In Formula 3-1, ring A₁₁, ring A₁₂, R₁₁to R₁₃, and d11 to d13 may each independently be the same as described herein,

ring A₁₄may be a C₅-C₃₀carbocyclic group or a C₂-C₃₀heterocyclic group,

R₁₄may be the same as described in connection with R₁₁provided herein,

d14 may be an integer from 0 to 10,

X₁₃may be a single bond, O, S, N(R_13a), C(R_13a)(R_13b), or Si(R_13a)(R_13b), wherein R_13aand R_13bmay each independently be the same as described in connection with R_11aand R_11bprovided herein, and

* and *′ may each indicate a binding site to a carbon atom in a benzene group of Formula 1.

In an embodiment, the heterocyclic compound may satisfy at least one of Conditions 1A to 3A:

Condition 1A

a group represented by

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in Formula 1 may be represented by Formula 3-1:

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wherein, in Formula 3-1,

rings A₁₁to A₁₃, R₁₁to R₁₃, and d11 to d13 may each independently be the same as described herein,

ring A₁₄may be a C₅-C₃₀carbocyclic group or a C₂-C₃₀heterocyclic group,

R₁₄may be the same as described in connection with R₁₁provided herein,

d14 may be an integer from 0 to 10,

* and *′ may each indicate a binding site to a carbon atom in a benzene group of Formula 1;

Condition 2A

a group represented by

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in Formula 1 may be represented by Formula 3-2:

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wherein, in Formula 3-2,

rings A₂₁to A₂₃, R₂₁to R₂₃, and d21 to d23 may each independently be the same as described herein,

ring A₂₄may be a C₅-C₃₀carbocyclic group or a C₂-C₃₀heterocyclic group,

R₂₄may be the same as described in connection with R₂₁provided herein,

d24 may be an integer from 0 to 10,

X₂₃may be a single bond, O, S, N(R_23a), C(R_23a)(R_23b), or Si(R_23a)(R_23b), wherein R_23aand R_23bmay each independently be the same as described in connection with R_21aand R_21bprovided herein, and

* and *′ may each indicate a binding site to a carbon atom in a benzene group of Formula 1.

Condition 3A

a group represented by

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in Formula 1 may be represented by Formula 3-3:

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wherein, in Formula 3-3,

rings A₃₁to A₃₃, R₃₁to R₃₃, and d31 to d33 may each independently be the same as described herein,

ring A₃₄may be a C₅-C₃₀carbocyclic group or a C₂-C₃₀heterocyclic group,

R₃₄may be the same as described in connection with R₃₁provided herein,

d34 may be an integer from 0 to 10,

X₃₃may be a single bond, O, S, N(R_33a), C(R_33a)(R_33b), or Si(R_33a)(R_33b), wherein R_33aand R_33bmay each independently be the same as described in connection with R_31aand R_31bprovided herein, and

* and *′ may each indicate a binding site to a carbon atom in a benzene group of Formula 1.

In the heterocyclic compound represented by Formula 1, a difference between a singlet energy level and a triplet energy level may be 0.3 electron volts (eV) or lower, for example, about 0 eV to about 0.3 eV. When the difference between a singlet energy level and a triplet energy level in the heterocyclic compound is within this range, the heterocyclic compound may emit delayed fluorescence, e.g., thermal activated delayed fluorescence (TADF).

In an embodiment, the heterocyclic compound may be selected from Compounds 1 to 31, but embodiments are not limited thereto:

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The heterocyclic compound represented by Formula 1 may have a structure in which at least one boron atom is included in a triindolobenzene-based backbone, as shown in Formula 1′:

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As Formula 1 has a triindolobenzene-based backbone, due to a large planar structure having a condensed ring, multiple resonance may be more (e.g., better) activated, and delocalization in electrons may be expanded. Due to an increased polarizability, an f value may be further increased, thus allowing the heterocyclic compound to be used as a highly efficient delayed fluorescence emitting material. In addition, the triindolobenzene-based backbone includes a substituent condensed to a heterocyclic ring, thus having a smaller number of freely rotating C—N bonds than a substituent that is not so condensed. Accordingly, a molecule (e.g., a molecule of the compound of Formula 1) may be more rigid in view of a bond dissociation energy (BDE), thereby supplementing chemical instability (that may be a weak point due to properties of a boron atom) with an increased electron density.

As Formula 1 includes at least one boron atom, the highest occupied molecular orbital (HOMO)/the lowest unoccupied molecular orbital (LUMO) separation may be increased, thereby enhancing multiple resonance, e.g., increasing short range charge transfer (CT). Accordingly, a high oscillator strength may be achieved, and a low ΔE_STas well, by separating a singlet and a triplet energy levels of a molecule. Therefore, luminescence efficiency may be improved, because a triplet state exciton is used for emission by facilitating reverse intersystem crossing and delayed fluorescence even at room temperature. In addition, when a molecule is transferred, probability of having a charge transfer characteristic in the transition of a triplet level (such as T₂or T₃) higher than T₁may be increased, and thus the LEST value may be further reduced. In particular, some of the heterocyclic compounds of the present embodiments and Compound A (DABNA-1) were subjected to discrete Fourier transform (DFT) calculation. As shown in Table 1, low ΔE_STvalues and increased oscillator strength (OSC) may be obtained.

TABLE 1

Dipole

No.
HOMO
LUMO
T1 (eV)
S1 (eV)
(Debye)
OSC
ΔE_ST

Compound
−4.73
−1.09
2.62
3.11
2.55
0.20
0.492

A

Compound
−4.941
−1.647
2.3882
2.837
2.947
0.2046
0.449

1

Compound
−4.775
−1.416
2.4175
2.871
2.500
0.3546
0.454

10

Compound
−5.108
−1.814
2.3488
2.606
2.729
0.1613
0.257

16

Compound
−5.228
−1.948
2.3115
2.602
2.602
0.0748
0.290

26

*Dipole: Criterion for molecular polarity.

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Therefore, an electronic device, e.g., an organic light-emitting device, applying the heterocyclic compound represented by Formula 1 may have a low driving voltage, high maximum quantum yield, high efficiency, and long lifespan.

Methods of synthesizing the heterocyclic compound represented by Formula 1 should be readily apparent to those of ordinary skill in the art by referring to Examples described herein.

At least one heterocyclic compound represented by Formula 1 may be included between a pair of electrodes in an organic light-emitting device. In some embodiments, the heterocyclic compound may be included in an emission layer. In some embodiments, the heterocyclic compound represented by Formula 1 may be used as a material for forming a capping layer, which may be positioned on outer sides of at least one of a pair of electrodes in an organic light-emitting device.

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

For example, the organic layer may include only Compound 1 as the heterocyclic compound. In this embodiment, Compound 1 may be included in the emission layer of the organic light-emitting device. In some embodiments, the organic layer may include Compounds 1 and 2 as the heterocyclic compounds. In this embodiment, Compounds 1 and 2 may be included in the same layer (for example, both Compounds 1 and 2 may be included in an emission layer) or in different layers (for example, Compound 1 may be included in an emission layer, and Compound 2 may be included in an electron transport layer).

In some embodiments, the first electrode may be an anode,

the second electrode may be a cathode, and

the organic layer may include the heterocyclic compound, and

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

In some embodiments, the hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a 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.

In some embodiments, the emission layer may include the heterocyclic compound.

In some embodiments, the emission layer may include a host and a dopant,

the host may be different from the dopant,

a content (e.g., amount) of the host may be greater than a content (e.g., amount) of the dopant, and

the dopant may include the heterocyclic compound.

In some embodiments, the emission layer may include a dopant and a host,

The host may include at least one heterocyclic compound.

In some embodiments, the emission layer may emit blue light or blue-green light.

In some embodiments, the heterocyclic compound may emit blue light or blue-green light having a maximum emission wavelength in a range of about 400 nanometers (nm) to about 500 nm.

In some embodiments, an electronic apparatus may include the organic light-emitting device.

In some embodiments, the electronic apparatus may include a thin-film transistor, the thin-film transistor may include a source electrode and a drain electrode, and the first electrode of the organic light-emitting device may be electrically coupled to the source electrode or the drain electrode.

The term “organic layer” as used herein refers to a single layer and/or a plurality of layers between the first electrode and the second electrode in an organic light-emitting device. A material included in the “organic layer” is not limited to an organic material.

In some embodiments, the organic light-emitting device may have i) a first electrode/organic layer/second electrode/second capping layer structure, ii) a first capping layer/first electrode/organic layer/second electrode structure, or iii) a first capping layer/first electrode/organic layer/second electrode/second capping layer structure, wherein the layers of each structure are sequentially stacked in each stated order. At least one of the first capping layer or the second capping layer may include the heterocyclic compound.

Description of FIG. 1

FIG. 1 illustrates a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 may include a first electrode 110, an organic layer 150, and a second electrode 190.

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

First Electrode 110

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

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

The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and any combinations thereof, but embodiments are not limited thereto. In some embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, as a material for forming the first electrode 110, at least one selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combinations thereof may be used, but embodiments are not limited thereto.

The first electrode 110 may have a single-layered structure, or a multi-layered structure including two or more layers. In some embodiments, the first electrode 110 may have a triple-layered structure of ITO/Ag/ITO, but embodiments are not limited thereto.

Organic Layer 150

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

The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 190.

Hole Transport Region in Organic Layer 150

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

The hole transport region may include at least one selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.

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

The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, a spiro-TPD, a 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), CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), a compound represented by Formula 201, and a compound represented by Formula 202:

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wherein, in Formulae 201 and 202,

L₂₀₁to L₂₀₄may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

L₂₀₅may be selected from *—O—*′, *—S—*′, *—N(Q₂₀₁)—*′, a substituted or unsubstituted C₁-C₂₀alkylene group, a substituted or unsubstituted C₂-C₂₀alkenylene group, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be an integer from 0 to 3,

xa5 may be an integer from 1 to 10, and

R₂₀₁to R₂₀₄and Q₂₀₁may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In some embodiments, in Formula 202, R₂₀₁and R₂₀₂may optionally be bound via a single bond, a dimethyl-methylene group, and/or a diphenyl-methylene group, and R₂₀₃and R₂₀₄may optionally be bound via a single bond, a dimethyl-methylene group, and/or a diphenyl-methylene group.

In an embodiment, in Formulae 201 and 202,

L₂₀₁to L₂₀₅may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂),

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

In one or more embodiments, xa1 to xa4 may each independently be 0, 1, or 2.

In one or more embodiments, xa5 may be 1, 2, 3, or 4.

In one or more embodiments, R₂₀₁to R₂₀₄and Q₂₀₁may each independently be selected from a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂),

wherein Q₃₁to Q₃₃may respectively be understood by referring to the descriptions of Q₃₁to Q₃₃provided herein.

In one or more embodiments, in Formula 201, at least one of R₂₀₁to R₂₀₃may be selected from:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments are not limited thereto.

In one or more embodiments, in Formula 202, i) R₂₀₁and R₂₀₂may be bound via a single bond, and/or ii) R₂₀₃and R₂₀₄may be bound via a single bond.

In one or more embodiments, in Formula 202, at least one of R₂₀₁to R₂₀₄may be selected from:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments are not limited thereto.

The compound represented by Formula 201 may be represented by Formula 201-1:

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In some embodiments, the compound represented by Formula 201 may be represented by Formula 201-2, but embodiments are not limited thereto:

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In some embodiments, the compound represented by Formula 201 may be represented by Formula 201-2(1), but embodiments are not limited thereto:

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The compound represented by Formula 201 may be represented by Formula 201A:

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In some embodiments, the compound represented by Formula 201 may be represented by Formula 201A(1), but embodiments are not limited thereto:

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In some embodiments, the compound represented by Formula 201 may be represented by Formula 201A-1, but embodiments are not limited thereto:

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In some embodiments, the compound represented by Formula 202 may be represented by Formula 202-1:

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In one or more embodiments, the compound represented by Formula 202 may be represented by Formula 202-1(1):

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In some embodiments, the compound represented by Formula 202 may be represented by Formula 202A:

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In some embodiments, the compound represented by Formula 202 may be represented by Formula 202A-1:

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In Formulae 201-1, 201-2, 201-2(1), 201A, 201A(1), 201A-1, 202-1, 202-1(1), 202A, and 202A-1,

L₂₀₁to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂to R₂₀₄may respectively be understood by referring to the description of L₂₀₁to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂to R₂₀₄provided herein,

L₂₀₅may be selected from a phenylene group and a fluorenylene group,

X₂₁₁may be selected from O, S, and N(R₂₁₁),

X₂₁₂may be selected from O, S, and N(R₂₁₂),

R₂₁₁and R₂₁₂may each be understood by referring to the description of R₂₀₃provided herein, and

R₂₁₃to R₂₁₇may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group.

The hole transport region may include at least one compound selected from Compounds HT1 to HT48, 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, and in some embodiments, about 100 Å to about 1,000 Å. When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and in some embodiments, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, and in some embodiments, about 100 Å to about 1,500 Å.

When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are each independently within any of these ranges, excellent (or improved) hole transport characteristics may be obtained without a substantial increase in driving voltage.

The emission auxiliary layer may increase light emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer. The electron blocking layer may reduce or eliminate the flow of electrons from an electron transport region. The emission auxiliary layer and the electron blocking layer may each independently include any of the aforementioned materials.

p-Dopant

The hole transport region may include a charge generating material, as well as any of 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.

In some embodiments, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be −3.5 eV or less.

The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments are not limited thereto.

In some embodiments, the p-dopant may include at least one selected from:

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

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

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

a compound represented by Formula 221,

but embodiments are not limited thereto:

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wherein, in Formula 221,

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

Emission Layer in Organic Layer 150

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, or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure. The stacked structure may include two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer. The two or more layers may be in direct contact with each other. In some embodiments, the two or more layers may be separated from each other. In one or more embodiments, the emission layer may include two or more materials. The two or more materials may include a red light-emitting material, a green light-emitting material, or a blue light-emitting material. The two or more materials may be mixed with each other in a single layer. The two or more materials mixed with each other in the single layer may emit white light.

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

The emission layer may include a host and a luminescent material. The luminescent material may include at least one of a phosphorescent dopant, a fluorescent dopant, or a quantum dot.

The amount of the dopant in the emission layer may be, for example, in a range of about 0.01 parts to about 15 parts by weight based on 100 parts by weight of the host, but embodiments are not limited thereto.

In some embodiments, the emission layer may emit blue light or blue-green light.

In some embodiments, the heterocyclic compound emits blue light or blue-green light having a maximum emission wavelength in a range of about 400 nm to about 500 nm.

The thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, and in some embodiments, about 200 Å to about 600 Å. 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.

Host in Emission Layer

The host may be different from the dopant, and a content (e.g., amount) of the host may be greater than a content (e.g., amount) of the dopant, and the host may include the heterocyclic compound represented by Formula 1.

The host may further include a compound represented by Formula 301: Formula 301

[Ar₃₀₁]_xb11-[(L₃₀₁)_xb1-R₃₀₁]_xb21

wherein, in Formula 301,

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

xb11 may be 1, 2, or 3,

L₃₀₁may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xb1 may be an integer from 0 to 5,

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

xb21 may be an integer from 1 to 5,

wherein Q₃₀₁to Q₃₀₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but embodiments are not limited thereto.

In some embodiments, in Formula 301, Ar₃₀₁may be selected from:

a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, and a dibenzothiophene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁to Q₃₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but embodiments are not limited thereto.

When xb11 in Formula 301 is 2 or greater, at least two Ar₃₀₁(s) may be bound via a single bond.

In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or 301-2:

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wherein, in Formulae 301-1 to 301-2,

A₃₀₁to A₃₀₄may each independently be selected from a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrimidine group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an indole group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a furan group, a benzofuran group, a dibenzofuran group, a naphthofuran group, a benzonaphthofuran group, a dinaphthofuran group, a thiophene group, a benzothiophene group, a dibenzothiophene group, a naphthothiophene group, a benzonapthothiophene group, and a dinaphthothiophene group,

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

R₃₁₁to R₃₁₄may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

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

L₃₀₁, xb1, R₃₀₁, and Q₃₁to Q₃₃may respectively be understood by referring to the descriptions of L₃₀₁, xb1, R₃₀₁, and Q₃₁to Q₃₃provided herein,

L₃₀₂to L₃₀₄may each be understood by referring to the descriptions of L₃₀₁provided herein,

xb2 to xb4 may each be understood by referring to the descriptions of xb1 provided herein, and

R₃₀₂to R₃₀₄may each be understood by referring to the descriptions of R₃₀₁provided herein.

In some embodiments, in Formulae 301, 301-1, and 301-2, L₃₀₁to L₃₀₄may each independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene 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 cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁to Q₃₃may respectively be understood by referring to the descriptions of Q₃₁to Q₃₃provided herein.

In some embodiments, in Formulae 301, 301-1, and 301-2, R₃₀₁to R₃₀₄may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁to Q₃₃may respectively be understood by referring to the descriptions of Q₃₁to Q₃₃provided herein.

In some embodiments, the host may include an alkaline earth metal complex. For example, the host may include a beryllium (Be) complex (e.g., Compound H55), a magnesium (Mg) complex, and/or a zinc (Zn) complex.

The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55, but embodiments are not limited thereto:

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Phosphorescent Dopant Included in Emission Layer of Organic Layer 150

The phosphorescent dopant may include an organometallic complex represented by Formula 401:

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wherein, in Formulae 401 and 402,

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

L₄₀₁may be selected from ligands represented by Formula 402, and xc1 may be 1, 2, or 3; when xc1 is 2 or greater, at least two L₄₀₁(s) may be identical to or different from each other,

L₄₀₂may be an organic ligand, and xc2 may be an integer selected from 0 to 4; when xc2 is 2 or greater, at least two L₄₀₂(s) may be identical to or different from each other,

X₄₀₁to X₄₀₄may each independently be a nitrogen or a carbon,

X₄₀₁and X₄₀₃may be bound to each other via a single bond or a double bond, X₄₀₂and X₄₀₄may be bound to each other via a single bond or a double bond,

A₄₀₁and A₄₀₂may each independently be a C₅-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group,

X₄₀₅may be a single bond, *—O—*′, *—C(═O)—*′, *—N(Q₄₁₁)-*′, *—C(Q₄₁₁)(Q₄₁₂)-*′, *—C(Q₄₁₁)═C(Q₄₁₂)-*′, *—C(Q₄₁₁)=*′, or *═C═*′, wherein Q₄₁₁and Q₄₁₂may each independently be hydrogen, deuterium, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group,

X₄₀₆may be a single bond, O, or S,

R₄₀₁and R₄₀₂may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-C₂₀alkyl group, a substituted or unsubstituted C₁-C₂₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂), wherein Q₄₀₁to Q₄₀₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a C₆-C₂₀aryl group, and a C₁-C₂₀heteroaryl group,

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

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

In an embodiment, in Formula 402, A₄₀₁and A₄₀₂may each independently be selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a dibenzofuran group, and a dibenzothiophene group.

In one or more embodiments, in Formula 402, i) X₄₀₁may be nitrogen, and X₄₀₂may be carbon, or ii) X₄₀₁and X₄₀₂may each be nitrogen.

In an embodiment, in Formula 402, R₄₀₁and R₄₀₂may each independently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group and a C₁-C₂₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornanyl group, and a norbornenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

—Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂),

wherein Q₄₀₁to Q₄₀₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group, but embodiments are not limited thereto.

In one or more embodiments, when xc1 in Formula 401 is 2 or greater, two A₄₀₁(s) of at least two L₄₀₁(s) may optionally be linked via X₄₀₇as a linking group; and/or two A₄₀₂(s) may optionally be linked via X₄₀₈as a linking group (see e.g., Compounds PD1 to PD4 and PD7). X₄₀₇and X₄₀₈may each independently be selected from a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₃)-*′, *—C(Q₄₁₃)(Q₄₁₄)-*′, and *—C(Q₄₁₃)=C(Q₄₁₄)-*′, wherein Q₄₁₃and Q₄₁₄may each independently be hydrogen, deuterium, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, but embodiments are not limited thereto.

L₄₀₂in Formula 401 may be any suitable monovalent, divalent, or trivalent organic ligand. For example, L₄₀₂may be selected from halogen, diketone (e.g., acetylacetonate), a carboxylic acid (e.g., picolinate), —C(═O), isonitrile, —CN, and phosphorus (e.g., phosphine and/or phosphite), but embodiments are not limited thereto.

In some embodiments, the phosphorescent dopant may include, for example, at least one selected from Compounds PD1 to PD25, but embodiments are not limited thereto:

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Fluorescent Dopant in Emission Layer

In some embodiments, the fluorescent dopant may include a heterocyclic compound represented by Formula 1:

The fluorescent dopant may further include an arylamine compound and/or a styrylamine compound.

In some embodiments, the fluorescent dopant may further include a compound represented by Formula 501:

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wherein, in Formula 501,

Ar₅₀₁may be selected from a substituted or unsubstituted C₅-C₆₀carbocyclic group and a substituted or unsubstituted C₁-C₆₀heterocyclic group,

L₅₀₁to L₅₀₃may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xd1 to xd3 may each independently be an integer from 0 to 3,

R₅₀₁and R₅₀₂may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and

xd4 may be an integer from 1 to 6.

In some embodiments, in Formula 501, Ar₅₀₁may be selected from:

a naphthalene group, a heptalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, and an indenophenanthrene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

In an embodiment, in Formula 501, L₅₀₁and L₅₀₃may each independently be selected from:

In an embodiment, in Formula 501, R₅₀₁and R₅₀₂may each independently be selected from:

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

In one or more embodiments, xd4 in Formula 501 may be 2, but embodiments are not limited thereto.

In some embodiments, the fluorescent dopant may be selected from Compounds FD1 to FD22:

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In some embodiments, the fluorescent dopant may be selected from the following compounds, but embodiments are not limited thereto:

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Quantum Dot

The emission layer included in the organic light-emitting device of the present disclosure may include a quantum dot material.

The quantum dot is a particle having a crystal structure of several to tens of nanometers in size. The quantum dot may include hundreds to thousands of atoms.

Because the quantum dot is very small in size, quantum confinement effect may occur. The quantum confinement is a phenomenon in which a band gap of an object becomes larger when the object becomes smaller, such as when the object becomes smaller than or reaches a nanometer size. Accordingly, when light of a wavelength having an energy larger than a band gap of the quantum dot is incident on the quantum dot, the quantum dot is excited by absorbing the light, emits light of a specific wavelength, and falls to the ground state. In this case, the wavelength of the emitted light may have a value corresponding to the band gap.

A core of the quantum dot may include a Group II-VI compound, a Group III-VI compound, a Group III-V compound, a Group IV-VI compound, a Group IV element or compound, a Group compound, or a combination thereof.

The Group II-VI compound may be selected from a binary compound selected from the group consisting of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; a ternary compound selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, and mixtures thereof; and a quaternary compound selected from the group consisting of CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and mixtures thereof.

The Group III-VI compound may include a binary compound such as In₂S₃and/or In₂Se₃; a ternary compound such as InGaS₃and/or InGaSe₃; or any combination thereof.

The Group III-V compound may be selected from a binary compound selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb and mixtures thereof; a ternary compound selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, and mixtures thereof; and a quaternary compound selected from the group consisting of GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. The Group III-V compound may further include a Group II metal (e.g., e.g., the Group III-V compound may be InZnP).

The Group IV-VI compound may be selected from a binary compound selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; a ternary compound selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and a quaternary compound selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. The Group IV element may be selected from the group consisting of Si, Ge, and a mixture thereof. The Group IV compound may be a binary compound selected from the group consisting of SiC, SiGe, and a mixture thereof.

In this case, the binary compound, the ternary compound, or the quaternary compound may each independently be present in particles at a uniform concentration or may be present in the same particle by being partially divided into different concentrations. One quantum dot may have a core-shell structure surrounding another quantum dot. An interface between a core and a shell of the quantum dot may have a concentration gradient where a concentration of elements present in the shell decreases toward the center.

In some embodiments, the quantum dot may have a core-shell structure including a core including the nano-sized crystals described above and a shell surrounding the core. The shell of the quantum dot may serve as a protective layer for preventing or reducing chemical denaturation of the core to maintain semiconductor characteristics and/or as a charging layer for imparting electrophoretic characteristics to the quantum dot. The shell may be monolayer or multilayer. An interface between a core and a shell may have a concentration gradient where a concentration of elements present in the shell decreases toward the center. Examples of the shell of the quantum dot include metal oxide, nonmetal oxide, a semiconductor compound, and a combination thereof, but embodiments are not limited thereto.

In some embodiments, the metal oxide or nonmetal oxide may each independently be a binary compound such as SiO₂, Al₂O₃, TiO₂, ZnO, MnO, Mn₂O₃, Mn₃O₄, CuO, FeO, Fe₂O₃, Fe₃O₄, CoO, Co₃O₄, and/or NiO; or a ternary compound such as MgAl₂O₄, CoFe₂O₄, NiFe₂O₄, and/or CoMn₂O₄, but embodiments are not limited thereto.

In some embodiments, the semiconductor compound may be CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, and/or AlSb, but embodiments are not limited thereto.

The quantum dot may have a full width of half maximum (FWHM) of a spectrum of an emission wavelength of about 45 nm or less, about 40 nm or less, or about 30 nm or less. When the FWHM of the quantum dot is within any of these ranges, color purity and/or color reproducibility may be improved. In addition, because light emitted through the quantum dot is emitted in all directions, an optical viewing angle may be improved.

The form (e.g., shape) of the quantum dot may be any suitable form and is not particularly limited. The quantum dot may be a spherical form, a pyramidal form, a multi-armed form, and/or a cubic nanoparticle, a nanotube, a nanowire, a nanofiber, a nano-plate particle, and/or the like.

The quantum dot may control color of emitted light according to the particle size. Accordingly, the quantum dot may have various emission colors such as blue, red, or green.

Electron Transport Region in Organic Layer 150

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

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

In some embodiments, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein the layers of each structure are sequentially stacked on the emission layer in each stated order, but embodiments are not limited thereto.

The electron transport region (e.g., the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron injection layer in the electron transport region) may include the heterocyclic compound represented by Formula 1.

In some embodiments, the electron transport region may include the heterocyclic compound represented by Formula 1, and may further include a metal-free compound containing at least one π electron-depleted nitrogen-containing ring.

The term “π electron-depleted nitrogen-containing ring” as used herein refers to a C₁-C₆₀heterocyclic group having at least one *—N═*′ moiety as a ring-forming moiety.

For example, the “π electron-depleted nitrogen-containing ring” may be i) a 5-membered to 7-membered heteromonocyclic group having at least one *—N═*′ moiety, ii) a heteropolycyclic group in which at least two 5-membered to 7-membered heteromonocyclic groups, each having at least one *—N═*′ moiety, are condensed, or iii) a heteropolycyclic group in which at least one of a 5-membered to 7-membered heteromonocyclic group, each having at least one *—N═*′ moiety, is condensed with at least one C₅-C₆₀carbocyclic group.

Examples of the π electron-depleted nitrogen-containing ring may include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole, but embodiments are not limited thereto.

In some embodiments, the electron transport region may include a compound represented by Formula 601: Formula 601

[Ar₆₀₁]_xe11-[(L₆₀₁)_xe1-R₆₀₁])_xe21,

wherein, in Formula 601,

Ar₆₀₁may be selected from a substituted or unsubstituted C₅-C₆₀carbocyclic group and a substituted or unsubstituted C₁-C₆₀heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xe1 may be an integer from 0 to 5,

R₆₀₁may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁), —S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂),

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

xe21 may be an integer from 1 to 5.

In some embodiments, at least one selected from Ar₆₀₁(s) in the number of xe11 and R₆₀₁(s) in the number of xe21 may include the π electron-depleted nitrogen-containing ring.

In some embodiments, in Formula 601, Ar₆₀₁may be selected from:

a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and

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

When xe11 in Formula 601 is 2 or greater, at least two Ar₆₀₁(s) may be bound via a single bond.

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

In some embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:

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wherein, in Formula 601-1,

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

L₆₁₁to L₆₁₃may each independently be understood by referring to the description of L₆₀₁provided herein,

xe611 to xe613 may each independently be understood by referring to the description of xe1 provided herein,

R₆₁₁to R₆₁₃may each independently be understood by referring to the description of R₆₀₁provided herein, and

R₆₁₄to R₆₁₆may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

In some embodiments, in Formulae 601 and 601-1, L₆₀₁and L₆₁₁to L₆₁₃may each independently be selected from:

but embodiments are not limited thereto.

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

In one or more embodiments, in Formulae 601 and 601-1, R₆₀₁and R₆₁₁to R₆₁₃may each independently be selected from:

—S(═O)₂(Q₆₀₁) and —P(═O)(Q₆₀₁)(Q₆₀₂),

wherein Q₆₀₁and Q₆₀₂may respectively be understood by referring to the descriptions of Q₆₀₁and Q₆₀₂provided herein.

The electron transport region may include at least one compound selected from Compounds ET1 to ET36, but embodiments are not limited thereto:

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In some embodiments, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), NTAZ, diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide (TSPO1), and 2,2′,2″-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) (TPBi):

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The thicknesses of the buffer layer, the hole blocking layer, and the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, and in some embodiments, about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer, or the electron control layer are each independently within any of these ranges, excellent (or improved) hole blocking characteristics and/or excellent (or improved) electron controlling characteristics may be obtained without a substantial increase in driving voltage.

The thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, and in some embodiments, about 150 Å to about 500 Å. 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 region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.

The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex may include a metal ion selected from a lithium (Li) ion, a sodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, and a cesium (Cs) ion. The alkaline earth metal complex may include a metal ion selected from a beryllium (Be) ion, a magnesium (Mg) ion, a calcium (Ca) ion, a strontium (Sr) ion, and a barium (Ba) ion. A ligand coordinated with the metal ion of the alkali metal complex and the alkaline earth metal complex may each independently be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments are not limited thereto.

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

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

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

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

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In some embodiments, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but embodiments are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may each independently be selected from oxides and halides (e.g., fluorides, chlorides, bromides, and/or iodides) of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively.

The alkali metal compound may be selected from alkali metal oxides (such as Li₂O, Cs₂O, and/or K₂O), and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and/or KI). In some embodiments, the alkali metal compound may be selected from LiF, Li₂O, NaF, LiI, NaI, CsI, and KI, but embodiments are not limited thereto.

The alkaline earth-metal compound may be selected from alkaline earth-metal compounds, such as BaO, SrO, CaO, Ba_xSr_1-xO (wherein 0<x<1), and/or Ba_xCa_1-xO (wherein 0<x<1). In some embodiments, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but embodiments are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, Sc₂O₃, Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In some embodiments, the rare earth metal compound may be selected from YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, and TbI₃, but embodiments are not limited thereto.

The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may each include ions of the above-described alkali metal, alkaline earth metal, and rare earth metal, respectively. The ligand coordinated with the metal ion of the alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may each independently be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments are not limited thereto.

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

The thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and in some embodiments, about 3 Å to about 90 Å. 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.

Second Electrode 190

The second electrode 190 may be on the organic layer 150. In an embodiment, the second electrode 190 may be a cathode, that is an electron injection electrode. In this embodiment, a material for forming the second electrode 190 may be a material having a low work function, for example, a metal, an alloy, an electrically conductive compound, or a combination thereof.

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

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

Description of FIGS. 2 to 4

Referring to FIG. 2, an organic light-emitting device 20 has a first capping layer 210, the first electrode 110, the organic layer 150, and the second electrode 190 structure, wherein the layers are sequentially stacked in this stated order. Referring to FIG. 3, an organic light-emitting device 30 has the first electrode 110, the organic layer 150, the second electrode 190, and a second capping layer 220 structure, wherein the layers are sequentially stacked in this stated order. Referring to FIG. 4, an organic light-emitting device 40 has the first capping layer 210, the first electrode 110, the organic layer 150, the second electrode 190, and the second capping layer 220 structure, wherein the layers are stacked in this stated order.

The first electrode 110, the organic layer 150, and the second electrode 190 illustrated in FIGS. 2 to 4 may be substantially the same as those illustrated in and described in connection with FIG. 1.

In the organic light-emitting devices 20 and 40, light emitted from the emission layer in the organic layer 150 may pass through the first electrode 110 (which may be a semi-transmissive electrode or a transmissive electrode) and through the first capping layer 210 to the outside. In the organic light-emitting devices 30 and 40, light emitted from the emission layer in the organic layer 150 may pass through the second electrode 190 (which may be a semi-transmissive electrode or a transmissive electrode) and through the second capping layer 220 to the outside.

The first capping layer 210 and the second capping layer 220 may improve the external luminescence efficiency based on the principle of constructive interference.

The first capping layer 210 and the second capping layer 220 may each independently include (e.g., be) an organic matter (e.g., an organic material), an inorganic matter (e.g., an inorganic material), or any combination thereof.

At least one of the first capping layer 210 and the second capping layer 220 may each independently include at least one selected from a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, a silicon-based inorganic matter (such as SiON, SiNx, and/or SiOx), a silicon-based organic matter, an acrylic compound, and an epoxy compound. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may each independently be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In some embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently include an amine-based compound.

In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently include a compound represented by Formula 201 or a compound represented by 202.

In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from Compounds HT28 to HT33 and Compounds CP1 to CP5, but embodiments are not limited thereto:

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

The layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region may be formed in a specific region by using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser printing, and laser-induced thermal imaging.

When any of the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region are each independently formed by vacuum deposition, the vacuum deposition may be performed at a deposition 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 deposition rate in a range of about 0.01 Angstroms per second (A/sec) to about 100 Å/sec, depending on the material to be included in each layer and the structure of each layer to be formed.

When any of the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region are each independently formed by spin coating, the spin coating may be performed at a coating rate of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and at a heat treatment temperature of about 80° C. to about 200° C., depending on the material to be included in each layer and the structure of each layer to be formed.

General Definitions of Substituents

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

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

The term “C₂-C₆₀alkynyl group” as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle and/or at either terminus of the C₂-C₆₀alkyl group. Non-limiting 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 “C₁-C₆₀alkoxy group” as used herein refers to a monovalent group represented by —OA₁₀₁(wherein A₁₀₁is the C₁-C₆₀alkyl group). Non-limiting examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.

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

The term “C₁-C₁₀heterocycloalkyl group” as used herein refers to a monovalent monocyclic group including at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and 1 to 10 carbon atoms as the remaining ring-forming atoms. Non-limiting examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C₁-C₁₀heterocycloalkylene group” as used herein refers to a divalent group having 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 double bond in its ring, and is not aromatic. Non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

The term “C₁-C₁₀heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group including at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms as the remaining ring-forming atoms, and at least one double bond in its ring. Non-limiting examples of the C₁-C₁₀heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C₁-C₁₀heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₁₀heterocycloalkyl group.

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

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and 1 to 60 carbon atoms as the remaining ring-forming atoms. Non-limiting examples of the C₁-C₆₀heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having the same structure as the C₁-C₆₀heteroaryl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀heteroarylene group each independently include two or more rings, the respective rings may be fused.

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

The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group that has two or more rings condensed and only carbon atoms as ring-forming atoms (e.g., 8 to 60 carbon atoms), wherein the entire molecular structure is non-aromatic. Non-limiting examples of the monovalent non-aromatic condensed polycyclic group may 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 selected from N, O, Si, P, and S, in addition to carbon atoms (e.g., 1 to 60 carbon atoms), as a ring-forming atom, wherein the entire molecular structure is non-aromatic. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group may include a 9H-xanthenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

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

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

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

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

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

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

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

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

“Ph” used herein represents a phenyl group, “Me” used herein represents a methyl group, “Et” used herein represents an ethyl group, “ter-Bu” or “But” used herein represents a tert-butyl group, and “OMe” used herein represents a methoxy group.

The term “biphenyl group” as used herein refers to a phenyl group substituted with at least one phenyl group. The “biphenyl group” may be “a substituted phenyl group” having a “C₆-C₆₀aryl group” as a substituent.

The term “terphenyl group” as used herein refers to a phenyl group substituted with at least one phenyl group. The “terphenyl group” may be “a substituted phenyl group” having a “C₆-C₆₀aryl group substituted with a C₆-C₆₀aryl group” as a substituent.

The symbols * and *′ as used herein, unless defined otherwise, refer to a binding site to an adjacent atom in a corresponding formula.

Hereinafter, compounds and an organic light-emitting device according to one or more embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of B used was identical to an amount of A used in terms of molar equivalents.

EXAMPLES
Synthesis Example 1: Synthesis of Compound 1

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Synthesis of Intermediate 1-1

10,15-dihydro-5H-diindolo[3,2-a:3′,2′-c]carbazole)(1 eq.), bromobenzene (2 eq.), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq.), BINAP (0.1 eq.), and sodium t-butoxide (3 eq.) were dissolved in toluene under a nitrogen atmosphere, followed by stirring at a temperature of 100° C. for 12 hours. Once the mixture was cooled and washed three times using ethyl acetate and water, the resulting organic layer was dried using anhydrous magnesium sulfate under reduced pressure. Subsequently, the residue was separated and purified through column chromatography to thereby obtain Intermediate 1-1 (yield: 65%).

Synthesis of Intermediate 1-2

Intermediate 1-1 (1 eq.), 1-bromo-3-fluorobenzene (1.5 eq.), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq.), tri-t-butylphosphine (0.1 eq.), and sodium t-butoxide (3 eq.) were dissolved in toluene under a nitrogen atmosphere, followed by stirring at a temperature of 100° C. for 12 hours. Once the mixture was cooled and washed three times using ethyl acetate and water, the resulting organic layer was dried using anhydrous magnesium sulfate under reduced pressure. Subsequently, the residue was separated and purified through column chromatography to thereby obtain Intermediate 1-2 (yield: 85%).

Synthesis of Intermediate 1-3

Intermediate 1-2 (1 eq.), 2-bromophenol (1.5 eq.), and potassium (III) phosphate (2 eq.) were dissolved in dimethylformamide (DMF), followed by stirring at a temperature of 160° C. for 12 hours. Once the mixture was cooled, the solvent was removed therefrom under reduced pressure, and the resultant was washed three times using dichloromethane and water. The resulting organic layer was dried using anhydrous magnesium sulfate under reduced pressure. Subsequently, the residue was separated and purified through column chromatography to thereby obtain Intermediate 1-3 (yield: 55%).

Synthesis of Compound 1

Intermediate 1-3 was dissolved in o-xylene, and the mixture was cooled to a temperature of −20° C. and stirred. Then, n-butyl lithium (1.2 eq.) was added thereto, followed by raising the temperature to 70° C. and stirring for 2 hours. The reaction glass was cooled to a temperature of −30° C., and boron tribromide (1.3 eq.) was slowly added thereto, followed by stirring at room temperature for 1 hour. The reaction glass was cooled to a temperature of 0° C., triethylamine (1.5 eq.) was added thereto, followed by raising the temperature to 120° C. and stirring for 5 hours. Once the mixture was cooled, a sodium acetate aqueous solution was added thereto to complete the reaction. Then, the reaction solution was removed by drying under reduced pressure in a rotary evaporator. The resultant was washed using diethyl ether and acetone, and filtered to thereby synthesize Compound 1 (yield: 21%).

Synthesis Example 2: Synthesis of Compound 10

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Synthesis of Intermediate 10-1

Intermediate 10-1 was synthesized in substantially the same manner as in Synthesis of Intermediate 1-2, except that 1-bromo-3-chlorobenzene was used instead of 1-bromo-3-fluorobenzene (yield: 80%).

Synthesis of Intermediate 10-2

Intermediate 10-2 was synthesized in substantially the same manner as in Synthesis of Intermediate 10-1, except that the Intermediate 10-1 was used instead of the Intermediate 1-1, and 2-bromo-N-phenylaniline was used instead of 1-bromo-3-chlorobenzene (yield: 74%).

Synthesis of Compound 10

Compound 10 was synthesized in substantially the same manner as in Synthesis of Compound 1, except that Intermediate 10-2 was used instead of Intermediate 1-3 (yield: 19%).

Synthesis Example 3: Synthesis of Compound 13

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Synthesis of Intermediate 13-1

1,3-dibromo-5-fluorobenzene (1 eq.), diphenylamine (1 eq.), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq.), tri-t-butylphosphine (0.1 eq.), and sodium t-butoxide (3 eq.) were dissolved in toluene under a nitrogen atmosphere, followed by stirring at a temperature of 80° C. for 12 hours. Once the mixture was cooled and washed three times using ethyl acetate and water, the resulting organic layer was dried using anhydrous magnesium sulfate under reduced pressure. Subsequently, the residue was separated and purified through column chromatography to thereby obtain Intermediate 13-1 (yield: 65%).

Synthesis of Intermediate 13-2

Intermediate 13-2 was synthesized in substantially the same manner as in Synthesis of Intermediate 1-2, except that Intermediate 13-1 was used instead of 1-bromo-3-fluorobenzene (yield: 60%).

Synthesis of Intermediate 13-3

Intermediate 13-3 was synthesized in substantially the same manner as in Synthesis of Intermediate 1-3, except that Intermediate 13-2 was used instead of Intermediate 1-2 (yield: 61%).

Synthesis of Compound 13

Compound 13 was synthesized in substantially the same manner as in Synthesis of Compound 1, except that Intermediate 13-3 was used instead of Intermediate 1-3 (yield: 15%).

Synthesis Example 4: Synthesis of Compound 16

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Synthesis of Intermediate 16-1

Intermediate 16-1 was synthesized in substantially the same manner as in Synthesis of Intermediate 1-1, except that 1-bromo-3-fluorobenzene was used instead of bromobenzene (yield: 60%).

Synthesis of Intermediate 16-2

Intermediate 16-2 was synthesized in substantially the same manner as in Synthesis of Intermediate 1-2, except that bromobenzene was used instead of 1-bromo-3-fluorobenzene (yield: 82%).

Synthesis of Intermediate 16-3

Intermediate 16-3 was synthesized in substantially the same manner as in Synthesis of Intermediate 1-3, except that 2-bromophenol was used in an amount of 2.2 eq. instead of 1.5 eq. (yield: 71%).

Synthesis of Compound 16

Intermediate 16-3 was dissolved in o-xylene, and the mixture was cooled to a temperature of −20° C. and stirred. Then, n-butyl lithium (2.2 eq.) was added thereto, followed by raising the temperature to 70° C. and stirring for 2 hours. The reaction glass was cooled to a temperature of −30° C., and boron tribromide (3.0 eq.) was slowly added thereto, followed by stirring at room temperature for 3 hour. The reaction glass was cooled to a temperature of 0° C., triethylamine (3.0 eq.) was added thereto, followed by raising the temperature to 120° C. and stirring for 5 hours. Once the mixture was cooled, a sodium acetate aqueous solution was added thereto to complete the reaction. Then, the reaction solution was removed by drying under reduced pressure in a rotary evaporator. The resultant was washed using diethyl ether and acetone, and filtered to thereby synthesize Compound 16 (yield: 15%).

Synthesis Example 5: Synthesis of Compound 26

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Synthesis of Intermediate 26-1

10,15-dihydro-5H-diindolo[3,2-a:3′,2′-c]carbazole (1 eq.), 1-bromo-3-fluorobenzene (3.3 eq.), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq.), tri-t-butylphosphine (0.1 eq.), and sodium t-butoxide (3 eq.) were dissolved in toluene under a nitrogen atmosphere, followed by stirring at a temperature of 100° C. for 12 hours. Once the mixture was cooled and washed three times using ethyl acetate and water, the resulting organic layer was dried using anhydrous magnesium sulfate under reduced pressure. Subsequently, the residue was separated and purified through column chromatography to thereby obtain Intermediate 26-1 (yield: 80%).

Synthesis of Intermediate 26-2

Intermediate 26-2 was synthesized in substantially the same manner as in Synthesis of Intermediate 1-3, except that 2-bromophenol was used in an amount of 3.3 eq. instead of 1.5 eq. (yield: 75%).

Synthesis of Compound 26

Compound 26 was synthesized in substantially the same manner as in Synthesis of Compound 16, except that n-butyl lithium was used in an amount of 3.3 eq. instead of 2.2 eq., and boron tribromide and triethyl amine were used in an amount of 3.5 eq. each instead of 3.0 eq. each (yield: 12%).

Synthesis Example 6: Synthesis of Compound 30

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Synthesis of Intermediate 30-1

Intermediate 30-1 was synthesized in substantially the same manner as in Synthesis of Intermediate 1-2, except that 8-bromo-1,2,3,4-tetrahydroquinoline was used instead of 1-bromo-3-fluorobenzene (yield: 75%).

Synthesis of Compound 30

Compound 30 was synthesized in substantially the same manner as in Synthesis of Compound 1, except that Intermediate 30-1 was used instead of Intermediate 1-3 (yield: 22%).

The ¹H NMR and MS/FAB results of the synthesized compounds are shown in Table 2. Methods of synthesizing compounds other than compounds shown in Table 2 should be easily understood to those skilled in the art by referring to the synthesis pathways and raw materials described above.

TABLE 2

Com-

MS/FAB

pound
H NMR (δ)
Calc.
Found

1
8.8-8.72(1H, d), 8.52-8.48(1H,d),
673.56
673.54

7.67-7.60(10H, m),

7.50-7.25(8H, m), 7.20-7.10(4H,m),

6.78-6.74(2H, m),

6.13-6.08(2H, m)

10
8.96-8.90(1H, d), 8.86-8.80(1H, d),
748.68
748.66

7.80-7.56(15H, m),

7.48-7.20(8H, m), 7.20-7.02(6H, m),

6.86-6.80(2H, m)

13
8.8-8.72(1H, d), 8.52-8.48(1H, d),
840.77
840.75

7.80-7.61(20H, m),

7.58-7.45(7H, m), 7.41-7.26(4H, m),

7.15-7.08(4H, m)

16
9.12-9.06(2H, d), 8.98-8.92(2H, d),
773.45
773.44

8.12-7.79(12H, m),

7.68-7.33(8H, m), 7.28-7.11(5H, m)

26
8.98-8.90(3H, d), 8.80-8.72(3H, d),
873.33
873.31

8.01-7.72(9H, m),

7.65-7.51(9H, m), 7.47-7.38(6H, m)

30
9.12-9.08(1H, d), 9.03-8.48(1H, d),
712.64
712.62

7.66-7.59(10H, m),

7.55-7.49(4H, m), 7.43-7.38(4H, m),

7.33-7.28(5H, m),

7.21-7.12(2H, m), 3.10-3.04(2H, m),

2.84-2.78(2H, m),

1.93-1.88(2H, m)

Example 1

A Corning, Inc. 15 Ohms per square centimeter (Ω/cm₂) (1,200 Å) ITO glass substrate was cut to a size of 50 millimeters (mm)×50 mm×0.7 mm, sonicated in isopropyl alcohol and pure water for 5 minutes in each solvent, and cleaned by exposure to ultraviolet rays with ozone to use the glass substrate as an anode. Then, the glass substrate was mounted to a vacuum-deposition apparatus.

N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPD) was vacuum-deposited on the ITO anode formed on the glass substrate to form a hole injection layer having a thickness of 300 Å. TCTA was then vacuum-deposited on the hole injection layer to form a first hole transport layer having a thickness of 200 Å.

Compound CzSi as a hole transporting compound was vacuum-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 100 Å.

mCP (as a host) and Compound 1 (as a dopant) were co-deposited on the second hole transport layer at a weight ratio of 99:1 to form an emission layer having a thickness of 200 Å.

Subsequently, TSPO1 was deposited on the emission layer to form a buffer layer having a thickness of 200 Å, and TPBi as an electron transporting compound was deposited on the buffer layer to form an electron transport layer having a thickness of 300 Å.

LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited on the electron injection layer to form a LiF/Al electrode having a thickness of 3,000 Å, thereby completing the manufacture of an organic light-emitting device.

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Examples 2 to 4 and Comparative Examples A to C

Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that compounds shown in Table 3 were used instead of Compound 1.

Evaluation Example 1

To evaluate characteristics of the organic light-emitting devices manufactured in Examples 1 to 4 and Comparative Examples A to C, the driving voltage, luminescence efficiency, and maximum external quantum yield (EQE) of the organic light-emitting devices at a current density of 10 milliamperes per square centimeter (mA/cm²) were measured. The driving voltage of the organic light-emitting devices were measured using a source meter (Keithley Instruments, 2400 series). The maximum external quantum yield of the organic light-emitting devices were measured using Hamamastu Absolute PL Quantum Yield Measurement System C9920-2-12. In evaluation of the maximum external quantum yield, luminance/current density was measured using a luminance meter with calibration of wavelength sensitivity, and the maximum external quantum yield was calculated by the angular luminance distribution on the assumption of the Lambertian surface. The evaluation results of the organic light-emitting devices are shown in Table 3.

TABLE 3

Maximum

Dopant in
Driving
Luminescence
external

emission
voltage
efficiency
quantum
Emission

layer
(V)
(Cd/A)
yield (%)
color

Example 1
Compound
4.7
16.1
20.3
blue

1

Example 2
Compound
4.64
19.5
20.6
Blue-

10

green

Example 3
Compound
4.74
23.2
20.5
Blue

16

Example 4
Compound
4.8
24.1
20.1
Blue

26

Comparative
Compound
5.2
12.1
14.3
Blue

Example A
A

Comparative
Compound
5.7
13.8
13.7
Blue-

Example B
B

green

Comparative
Compound
5.4
11.7
5.1
Dark blue

Example C
C

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Referring to the results of Table 3, the organic light-emitting devices of Examples 1 to 4 were found to have excellent driving voltage, luminescence efficiency, and external quantum yield, as compared with the organic light-emitting devices of Comparative Examples A, B, and C.

As used herein, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.

In addition, the terms “substantially,” “about,” and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art.

Also, any numerical range recited herein is intended to include all subranges of the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.

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

Number	Name	Date	Kind
10374166	Hatakeyama et al.	Aug 2019	B2
20190058124	Hatakeyama et al.	Feb 2019	A1
20190181350	Hatakeyama et al.	Jun 2019	A1
20190207112	Hatakeyama et al.	Jul 2019	A1
20200066997	Huang et al.	Feb 2020	A1
20200091431	Hatakeyama et al.	Mar 2020	A1

Number	Date	Country
107417715	Dec 2017	CN
10-2016-0119683	Oct 2016	KR
10-2018-0083152	Jul 2018	KR
10-2018-0108604	Oct 2018	KR
10-2018-0134850	Dec 2018	KR
10-2019-0025065	Mar 2019	KR
10-2019-0069295	Jun 2019	KR
WO 2016152544	Sep 2016	WO
WO 2017138526	Aug 2017	WO
WO 2018095397	May 2018	WO
WO 2018212169	Nov 2018	WO

Heterocyclic compound, organic light-emitting device including heterocyclic compound, and electronic device including organic light-emitting device

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Entry
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