Condensed cyclic compound, light emitting device including same, and electronic device including light emitting device

Abstract

Provided are a fused ring compound represented by Formula 1 below, a light-emitting device including the same, and an electronic apparatus including the light-emitting device. For the description of Formula 1, the description provided in this specification is referenced. Formula 1 # imgabs0 #

Description

[0001] Cross-reference to related applications

[0002] This application claims priority to Korean Patent Application Nos. 10-2024-0007635, filed on January 17, 2024, and 10-2024-0018417, filed on February 6, 2024, with the Korean Intellectual Property Office, the entire disclosures of which are incorporated herein by reference. Technical Field

[0003] The present disclosure relates to a polycyclic compound, a light-emitting device including the same, and an electronic device including the light-emitting device. Background Art

[0004] In a light-emitting device, an organic light-emitting device is a self-emitting device having a wide viewing angle, a high contrast ratio, a short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to devices of related art, and generates a full-color image.

[0005] In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode and including an emission layer. A hole transport region may be provided between the anode and the emission layer, and an electron transport region may be provided between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. Holes and electrons recombine in the emission layer to generate excitons. When the excitons transition from an excited state to a ground state, light is emitted. Summary of the Invention

[0006] Provided are a novel polycyclic compound, a light-emitting device using the same, and an electronic device including the light-emitting device.

[0007] 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 present disclosure.

[0008] According to an aspect of the present disclosure, provided is a polycyclic compound represented by Formula 1:

[0009] Formula 1

[0010]

[0011] wherein Ar0 in Formula 1 is a group represented by Formula 2,

[0012] Formula 2

[0013]

[0014] wherein, in Formulas 1 and 2,

[0015] Ring CY1 to Ring CY3 are each independently a C5-C 60 carbocyclic group or a C3-C 60 heterocyclic group,

[0016] W1 is a single bond, O, S, N(R8), N(Ar1), C(R8)(R9), or Si(R8)(R9),

[0017] W2 is a single bond, O, S, N(R 10 ), N(Ar2), C(R 10 )(R 11 ), or Si(R 10 )(R 11 ),

[0018] n1 and n2 are each independently 0 or 1,

[0019] When n1 is 0, *-(W1) n1 -' does not exist,

[0020] When n2 is 0, *-(W2) n2 -' does not exist,

[0021] The sum of n1 and n2 is 1 or 2,

[0022] T1 is a single bond, C(R 12 )(R 13 ), Si(R 12 )(R 13 ), N(R 12 ), B(R 12 ), O, S, Se, or Te,

[0023] Ar1 and Ar2 are each independently a group represented by Formula 2,

[0024] R1 to R 13 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a substituted or unsubstituted C1-C 60 alkyl, a substituted or unsubstituted C2-C 60 alkenyl, a substituted or unsubstituted C2-C 60 alkynyl, a substituted or unsubstituted C1-C 60 alkoxy, a substituted or unsubstituted C1-C 60 alkylthio, a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C1-C 10 heterocycloalkyl, a substituted or unsubstituted C3-C10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0025] a1 to a3 and m are each independently an integer from 0 to 10,

[0026] a4 to a6 are each independently an integer from 0 to 4,

[0027] a7 is an integer from 0 to 8,

[0028] R1 to R3 and R8 to R 11 Two or more of which are optionally connected to each other to form a substituted or unsubstituted C5-C 30 Carbocyclic group, or a substituted or unsubstituted C1-C 30 Heterocyclic group,

[0029] Substituted C5-C 30 Carbocyclic group, substituted C1-C 30 Heterocyclic group, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 At least one substituent of heteroaryl, substituted monovalent non-aromatic fused polycyclic group and substituted monovalent non-aromatic fused heteropolycyclic group may be

[0030] deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio,

[0031] C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 ), or a combination thereof,

[0032] C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 23 )、-Si(Q 23 )(Q 24 )(Q 25 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 )、or a combination thereof,

[0033] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39)、 or -P(Q 38 )(Q 39 ), or

[0034] their combination, and

[0035] Q1 to Q9, Q 11 to Q 19 , Q 21 to Q 29 and Q 31 to Q 39 are each independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; amino; amidino; hydrazino; hydrazono; a carboxylic acid group or its salt; a sulfonic acid group or its salt; a phosphoric acid group or its salt; or a C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C1-C 60 alkylthio, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, C1-C 60 alkyl, C6-C 60 aryl, or their combination.

[0036] According to another aspect of the present disclosure, a light-emitting device includes a first electrode, a second electrode, and an intermediate layer disposed between the first electrode and the second electrode and including an emission layer, wherein the intermediate layer includes one or more of the polycyclic compounds.

[0037] According to another aspect of the present disclosure, an electronic device includes the light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] From the following description taken in conjunction with Figure 1 consideration, the above and other aspects, features, and advantages of some embodiments of the present disclosure will become more apparent, Figure 1 showing a schematic cross-sectional view of a light-emitting device according to an exemplary embodiment. DETAILED DESCRIPTION

[0039] The embodiments will now be described in detail, examples thereof being illustrated in the accompanying drawings, wherein like reference numerals in the specification always refer to like elements. In this regard, the embodiments may have different forms and should not be construed as limited to the description set forth herein. Accordingly, the embodiments are described only by way of example below with reference to the accompanying drawings. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. The phrase such as "at least one (kind)" when before or after a list of elements modifies the entire list of elements and not individual elements of the list.

[0040] It will be understood that when an element is referred to as being "on" another element, it can be directly on the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being "directly on" another element, no intervening elements are present.

[0041] It will be understood that although the terms "first", "second", "third", etc. may be used herein to describe various elements, components, regions, layers and / or parts, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or part from another element, component, region, layer or part. Thus, without departing from the teachings herein, the "first element", "component", "region", "layer", or "part" discussed below may be referred to as a second element, component, region, layer, or part.

[0042] The terms used herein are for the purpose of describing particular embodiments only and are not intended to be limiting. As used herein, the indefinite articles "a", "an", the definite article "the", and "at least one (kind)" do not denote a limitation of quantity and are intended to cover both the singular and the plural, unless the context clearly indicates otherwise. For example, "element" has the same meaning as "at least one element" unless the context clearly indicates otherwise.

[0043] "Or" means "and / or". As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. It will be further understood that the terms "comprising" or "including" when used in this specification indicate the presence of the stated features, regions, wholes, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, regions, wholes, steps, operations, elements, components, and / or their groups.

[0044] In addition, relative terms such as "lower" or "bottom" and "upper" or "top" may be used herein to describe the relationship of one element to another as shown in the figures. It will be understood that relative terms are intended to include different orientations of the device in addition to the orientation (position) depicted in the figures. For example, if the device in one of the figures is flipped, an element described as on the "lower" side of another element will be oriented on the "upper" side of the other element. Thus, depending on the specific orientation of the figure, the exemplary term "lower" can encompass both the "lower" and "upper" orientations. Similarly, if the device in one of the figures is flipped, an element described as "beneath" or "under" another element will be oriented "above" the other element. Thus, the exemplary terms "beneath" or "under" can encompass both above and beneath.

[0045] As used herein, "about" or "approximately" includes the stated value and means within an acceptable deviation range for the specific value as determined by one of ordinary skill in the art in view of the measurements discussed and the error associated with the measurement of the specific quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations of the stated value, or within ±10% or 5%.

[0046] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the present disclosure and the relevant art, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0047] Exemplary embodiments are described herein with reference to cross-sectional views that are schematic illustrations of idealized embodiments. Thus, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are to be expected. Accordingly, the embodiments described herein should not be construed as limited to the specific shapes of the regions as illustrated herein, but include deviations in shapes that result, for example, from manufacturing. For example, regions illustrated or described as flat may typically have rough and / or non-linear features. Also, sharp corners illustrated may be rounded. Thus, the regions shown in the figures are schematic in nature and their shapes are not intended to illustrate the exact shape of the regions and are not intended to limit the scope of the claims.

[0048] Description of polycyclic compounds

[0049] One aspect provides a polycyclic compound represented by Formula 1:

[0050] Formula 1

[0051]

[0052] wherein Ar0 in Formula 1 is a group represented by Formula 2,

[0053] Formula 2

[0054]

[0055] wherein, in Formulas 1 and 2,

[0056] Ring CY1 to Ring CY3 may each independently be a C5-C 60 carbocyclic group or a C3-C 60 heterocyclic group,

[0057] W1 may be a single bond, O, S, N(R8), N(Ar1), C(R8)(R9), or Si(R8)(R9),

[0058] W2 may be a single bond, O, S, N(R 10 ), N(Ar2), C(R 10 )(R 11 ), or Si(R 10 )(R 11 ),

[0059] n1 and n2 may each independently be 0 or 1,

[0060] when n1 is 0, *-(W1) n1 -' does not exist,

[0061] when n2 is 0, *-(W2) n2 -' does not exist,

[0062] the sum of n1 and n2 may be 1 or greater,

[0063] T1 may be a single bond, C(R 12 )(R 13 ), Si(R 12 )(R 13 ), N(R 12 ), B(R 12 ), O, S, Se or Te,

[0064] Ar1 and Ar2 may each independently be a group represented by Formula 2,

[0065] R1 to R 13 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a substituted or unsubstituted C1-C 60Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0066] a1 to a3 and m can each independently be an integer from 0 to 10,

[0067] a4 to a6 can each independently be an integer from 0 to 4,

[0068] a7 can be an integer from 0 to 8,

[0069] Two or more of R1 to R3 and R8 to R 11 can optionally be connected to each other to form a substituted or unsubstituted C5-C 30 carbocyclic group, or a substituted or unsubstituted C1-C 30 heterocyclic group,

[0070] Substituted C5-C 30 carbocyclic group, substituted C1-C 30 heterocyclic group, substituted C1-C 60 alkyl, substituted C2-C 60 alkenyl, substituted C2-C 60 alkynyl, substituted C1-C 60 alkoxy, substituted C1-C 60 alkylthio, substituted C3-C 10 cycloalkyl, substituted C1-C 10 heterocycloalkyl, substituted C3-C 10 cycloalkenyl, substituted C1-C 10Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 At least one substituent of heteroaryl, substituted monovalent non-aromatic fused polycyclic group, and substituted monovalent non-aromatic fused heteropolycyclic group may be:

[0071] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio;

[0072] C1-C each substituted by the following 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19), -P(Q 18 )(Q 19 ), or a combination thereof;

[0073] C3-C, each unsubstituted or substituted with the following 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C1-C 60 alkylthio, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 23 ), -Si(Q 23 )(Q 24 )(Q 25 ), -Ge(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), -P(Q 28 )(Q 29 ), or a combination thereof;

[0074] -N(Q 31 )(Q 32 ), -Si(Q 33)(Q 34 )(Q 35 )、 -Ge(Q 33 )(Q 34 )(Q 35 )、 -B(Q 36 )(Q 37 )、 -P(=O)(Q 38 )(Q 39 )、 or -P(Q 38 )(Q 39 ); or

[0075] their combination, and

[0076] Q1 to Q9, Q 11 to Q 19 , Q 21 to Q 29 and Q 31 to Q 39 can each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amino; amidino; hydrazino; hydrazono; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphoric acid group or its salt; or C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C1-C 60 alkylthio, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, C1-C 60 alkyl, C6-C 60 aryl, or their combination.

[0077] According to an embodiment, ring CY1 to ring CY3 can each independently be a cyclopentadienyl group, an adamantyl group, a norbornyl group, a phenyl group, a bicyclopentadienyl group, a naphthyl group, an azulene group, an indacene group, an acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, a group, a perylene group, a pentacene group, a heptacene group, a tetracene group, a picene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, an indene group, a fluorene group, a spirobifluorene group, a benzo[b]fluorene group, an indenophenanthrene group, an indenoanthracene group, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indolocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothiophenocarbazole group, a benzosilolecarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothiophenodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, or an azadibenzofuran group.

[0078] According to an embodiment, each of ring CY1 to ring CY3 may independently be a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group.

[0079] According to an embodiment, i) n1 may be 1 and n2 may be 0, or ii) n1 may be 0 and n2 may be 1.

[0080] According to an embodiment, the sum of n1 and n2 may be 1, W1 may be N(R8) or N(Ar1), and W2 may be N(R 10 ) or N(Ar2).

[0081] According to an embodiment, the sum of n1 and n2 may be 1, W1 may be N(Ar1), and W2 may be N(Ar2).

[0082] According to an embodiment, Ar0 and Ar1 may be the same as each other, or Ar0 and Ar2 may be the same as each other.

[0083] According to an embodiment, the sum of n1 and n2 may be 1, W1 may be N(Ar1), W2 may be N(Ar2), the sum of a1 to a3 is at least 1, and at least one of R1 to R3 is not hydrogen. In an embodiment, the sum of a1 to a3 is at least 2, and at least two of R1 to R3 are not hydrogen. In an embodiment, the sum of a1 to a3 is at least 3, and at least three of R1 to R3 are not hydrogen.

[0084] According to an embodiment, the sum of n1 and n2 may be 1, W1 may be N(Ar1), W2 may be N(Ar2), the sum of a1 to a3 is at least 1, and at least one of R1 to R3 is a substituted or unsubstituted C1-C 60 alkyl, a substituted or unsubstituted C6-C 60 aryl, a substituted or unsubstituted C1-C 60 heteroaryl, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group. In an embodiment, the sum of a1 to a3 is at least 2, and at least two of R1 to R3 are each independently a substituted or unsubstituted C1-C 60 alkyl, a substituted or unsubstituted C6-C 60 aryl, a substituted or unsubstituted C1-C 60 heteroaryl, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group. In an embodiment, the sum of a1 to a3 is at least 3, and at least three of R1 to R3 are each independently a substituted or unsubstituted C1-C 60 alkyl, a substituted or unsubstituted C6-C 60 aryl, a substituted or unsubstituted C1-C 60 heteroaryl, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0085] According to one embodiment, the fused-ring compound may have a symmetric structure.

[0086] According to an embodiment, the fused-ring compound may have a symmetric structure based on i) the straight line connecting the center of CY1 and B, or ii) the straight line connecting the center of CY3 and B.

[0087] According to an embodiment, when n1 is 0, n2 is 1, W2 is N(Ar2), and Ar0 and Ar2 are the same as each other, the fused-ring compound may have a symmetric structure.

[0088] According to an embodiment, when n1 is 0, n2 is 1, W2 is N(Ar2), Ar0 and Ar2 are the same as each other, a1 and a2 are 1, and R1 and R2 are the same as each other, the fused-ring compound may have a symmetric structure.

[0089] According to another embodiment, the fused-ring compound may have an asymmetric structure.

[0090] According to an embodiment, when n1 is 0, n2 is 1, W2 is N(Ar2), and Ar0 and Ar2 are different from each other, the fused-ring compound may have an asymmetric structure.

[0091] According to an embodiment, when n1 is 0, n2 is 1, W2 is N(Ar2), Ar0 and Ar2 are different from each other, a1 and a2 are 1, and R1 and R2 are the same as each other, the fused-ring compound may have an asymmetric structure.

[0092] According to an embodiment, when n1 is 0, n2 is 1, W2 is N(Ar2), Ar0 and Ar2 are the same as each other, a1 and a2 are 1, and R1 and R2 are different from each other, the fused-ring compound may have an asymmetric structure.

[0093] According to an embodiment, when n1 is 0, n2 is 1, W2 is N(Ar2), Ar0 and Ar2 are different from each other, a1 and a2 are 1, and R1 and R2 are different from each other, the fused-ring compound may have an asymmetric structure.

[0094] According to an embodiment, T1 may be a single bond, O, or S.

[0095] According to an embodiment, T1 may be a single bond.

[0096] According to an embodiment, R1 to R3 may each independently be:

[0097] hydrogen, deuterium, -F, or a cyano group; or

[0098] a C1-C 20 alkyl group which is unsubstituted or substituted with deuterium, -F, a cyano group, or a combination thereof; or

[0099] a phenyl group or a carbazolyl group which is each unsubstituted or substituted with: deuterium, -F, a cyano group, a C1-C 20 alkyl group, a phenyl group, or a combination thereof.

[0100] According to an embodiment, R1 to R3 may each independently be:

[0101] hydrogen;

[0102] methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, or 1,2-dimethylpropyl, each unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, or a combination thereof; or

[0103] phenyl or carbazolyl, each unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl, phenyl, or a combination thereof.

[0104] According to an embodiment, one of R1 and one of R2 may each independently be a carbazolyl group substituted with deuterium, such as a carbazolyl group partially or fully substituted with deuterium, and the remaining of R1 and the remaining of R2 may each independently be hydrogen, deuterium, or a C1-C 20 alkyl group unsubstituted or substituted with deuterium, -F, cyano, or a combination thereof. One of R3 may be a C1-C 20 alkyl group (e.g., a straight-chain C1-C 20 alkyl group or a branched C3-C 20 alkyl group) unsubstituted or substituted with deuterium, -F, cyano, or a combination thereof, and the remaining of R3 may each independently be hydrogen or deuterium.

[0105] According to an embodiment, R4 to R7 may each independently be:

[0106] hydrogen, deuterium, -F, or cyano; or

[0107] a C1-C 20 alkyl group unsubstituted or substituted with deuterium, -F, cyano, or a combination thereof; or

[0108] phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or azacarbazolyl, each unsubstituted or substituted with: deuterium, -F, cyano, C1-C 20 alkyl, phenyl, or a combination thereof.

[0109] According to an embodiment, R4 to R7 may each independently be:

[0110] hydrogen;

[0111] Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, or 1,2-dimethylpropyl, each unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, or a combination thereof; or

[0112] Phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or azacarbazolyl, each unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl, phenyl, or a combination thereof.

[0113] According to an embodiment, R8 to R 13 may each independently be:

[0114] Hydrogen, deuterium, -F, or cyano;

[0115] C1-C, each unsubstituted or substituted with: 20 alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorene, or dibenzosilolyl: deuterium, -F, cyano, C1-C 20 alkyl, phenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorene, dibenzosilolyl, or a combination thereof; or

[0116] -N(Q1)(Q2), and

[0117] Q1 and Q2 may each independently be C1-C, each unsubstituted or substituted with: 20 alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorene, or dibenzosilolyl: deuterium, -F, cyano, C1-C 20 alkyl, phenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorene, dibenzosilolyl, or a combination thereof.

[0118] According to an embodiment, the fused-ring compound may be represented by Formula 1A:

[0119] Formula 1A

[0120]

[0121] wherein, in Formula 1A,

[0122] W3 may be O, S, N(R 10)、N(Ar2), C(R 10 )(R 11 ), or Si(R 10 )(R 11 ),

[0123] Ar0, Ar2, R1 to R3, R 10 and R 11 may each be as described herein,

[0124] b1 and b2 may each independently be an integer from 0 to 4, and

[0125] b3 may be an integer from 0 to 3.

[0126] For example, in Formula 1A, R1, R2, and R3 at the para-position of the corresponding benzene ring relative to B may each not be hydrogen. For example, said R1 and R2 may each independently be a carbazolyl group substituted with deuterium, such as a carbazolyl group partially or completely substituted with deuterium, and said R3 may be an unsubstituted or deuterium-, -F-, cyano-, or a combination thereof-substituted C1-C 20 alkyl (e.g., linear C1-C 20 alkyl or branched C3-C 20 alkyl). As for R1, R2, and R3 at the remaining positions, they may each independently be hydrogen, deuterium, or an unsubstituted or deuterium-, -F-, cyano-, or a combination thereof-substituted C1-C 20 alkyl.

[0127] In an embodiment, m may be 0 or 1.

[0128] According to an embodiment, the group represented by Formula 2 may be any one of the groups represented by Formulas 2-1 to 2-9:

[0129]

[0130]

[0131]

[0132] wherein, in Formulas 2-1 to 2-9,

[0133] T1, R4 to R7, and a4 to a7 are as described herein.

[0134] In Formulas 2-1 to 2-9, for example, T1 may be a single bond, O, or S, a7 may be an integer from 1 to 8, and R7 may each independently be hydrogen, deuterium, -F, cyano, or an unsubstituted or deuterium-, -F-, cyano-, or a combination thereof-substituted C1-C 20Alkyl. For example, T1 may be a single bond, a7 may be 8, and at least one of R7 (e.g., one, two, three, four, five, six, seven, or all) may be deuterium, and the remainder of R7 may be hydrogen or C1-C deuterium-substituted 20 alkyl.

[0135] According to an embodiment, the polycyclic compound may include at least one deuterium, tert-butyl, or a combination thereof.

[0136] According to an embodiment, the polycyclic compound may be any one of Compounds 1 to 66:

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] Ar0 in Formula 1 may be a group represented by Formula 2, and the group represented by Formula 2 may include an o-biphenyl group and a hetero-fused ring containing N (also referred to as a substituent containing a heteroatom). Therefore, in the polycyclic compound represented by Formula 1, introducing a substituent containing a heteroatom at its end contributes to the stabilization of the light-emitting process, and thus, a relatively small full width at half maximum (FWHM) of emission can be obtained and a relatively low highest occupied molecular orbital (HOMO) energy level can be maintained, allowing emission of light with a short wavelength. Moreover, an electronic device such as a light-emitting device using the polycyclic compound can have improved external quantum efficiency and improved lifetime characteristics.

[0144] According to an embodiment, the FWHM of the emission spectrum of the polycyclic compound may be from about 5 nm to about 40 nm, for example, from about 10 nm to about 25 nm.

[0145] In some embodiments, the emission peak wavelength in the emission spectrum of the polycyclic compound may be from about 400 nm to about 500 nm, for example, from about 440 nm to about 470 nm.

[0146] In some embodiments, the singlet (S1) energy level of the polycyclic compound may be from about 2.4 eV to about 3.1 eV.

[0147] In some embodiments, the absolute value of the difference between the singlet (S1) energy level and the triplet (T1) energy level of the polycyclic compound may be greater than about 0 eV and less than or equal to about 1 eV.

[0148] In some embodiments, the absolute value of the highest occupied molecular orbital (HOMO) energy level of the fused-ring compound may be from about 4.0 eV to about 6.5 eV.

[0149] The method for synthesizing the fused-ring compound can be recognized by those skilled in the art by referring to the synthesis examples described later.

[0150] Light-emitting device

[0151] The fused-ring compound may be suitable for use as an intermediate layer of a light-emitting device, for example, as a material for an emission layer in the intermediate layer. Another aspect of the present disclosure provides a light-emitting device including a first electrode, a second electrode, and an intermediate layer disposed between the first electrode and the second electrode and including an emission layer, wherein the intermediate layer includes at least one type of the fused-ring compound.

[0152] Since the light-emitting device includes an intermediate layer containing at least one type of the fused-ring compound as described above, the light-emitting device can emit blue light having a relatively narrow full width at half maximum (FWHM) and a short wavelength, and has improved external quantum efficiency, improved luminous efficiency, and / or improved lifetime characteristics.

[0153] The fused-ring compound can be used between electrode pairs of a light-emitting device. For example, the fused-ring compound can be included in the emission layer. In this regard, the emission layer may further include a host. In the emission layer, the amount (e.g., weight) of the host may be greater than the amount (e.g., weight) of the fused-ring compound. The emission layer can emit red light, green light, or blue light. For example, the emission layer can emit blue light.

[0154] According to an embodiment, the CIEy value of the light emitted from the emission layer may be from about 0.040 to about 0.170, from about 0.050 to about 0.170, from about 0.060 to about 0.170, from about 0.040 to about 0.165, from about 0.050 to about 0.165, or from about 0.060 to about 0.165.

[0155] In some embodiments, the emission peak wavelength of the light emitted from the emission layer may be from about 440 nm to about 470 nm, from about 445 nm to about 470 nm, from about 450 nm to about 470 nm, from about 455 nm to about 470 nm, from about 460 nm to about 470 nm, from about 440 nm to about 465 nm, from about 445 nm to about 465 nm, from about 450 nm to about 465 nm, from about 455 nm to about 465 nm, or from about 460 nm to about 465 nm.

[0156] The emission layer may further include a host. The host may be as described herein.

[0157] The first electrode can be an anode serving as a hole injection electrode, and the second electrode can be a cathode serving as an electron injection electrode, or the first electrode can be a cathode serving as an electron injection electrode, and the second electrode can be an anode serving as a hole injection electrode.

[0158] For example, in a light-emitting device (also referred to as an organic light-emitting device hereinafter), the first electrode can be an anode, the second electrode can be a cathode, and the intermediate layer can 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, where the hole transport region can include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, an auxiliary layer, or a combination thereof, and the electron transport region can include a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0159] As used herein, the term "intermediate layer" refers to a single or multiple layers disposed between the first electrode and the second electrode in a light-emitting device. In addition to organic compounds, the "intermediate layer" can also include organometallic complexes containing metals.

[0160] In some embodiments, the emission layer can include a first embodiment or a second embodiment:

[0161] First embodiment

[0162] The emission layer includes at least one polycyclic compound represented by Formula 1, and the polycyclic compound can function as an emitter such as a delayed fluorescence emitter. That is, the polycyclic compound can be an emitter. For example, among all the light-emitting components of the emission layer, the light-emitting component emitted from the polycyclic compound can be at least 80%, at least 85%, at least 90%, or at least 95%. The light emitted from the polycyclic compound can be blue light. The emission layer can further include a sensitizer, and the sensitizer and the polycyclic compound can be different from each other. The sensitizer can be an organometallic compound, a delayed fluorescence material, an instantaneous fluorescence material, or a combination thereof. For every 100 parts by weight of the emission layer, the amount (by weight) of the sensitizer can be about 0.01 part by weight to about 20 parts by weight, for example, about 0.01 part by weight to about 10 parts by weight.

[0163] Second embodiment

[0164] The emission layer includes at least one polycyclic compound represented by Formula 1, and the polycyclic compound can function as a sensitizer or an auxiliary dopant. That is, the polycyclic compound can be a sensitizer or an auxiliary dopant. The sensitizer can effectively transfer excitons from the host to the emitter. The emission layer can further include an emitter, and the emitter can be different from the polycyclic compound. The emitter can be an organometallic compound, an instantaneous fluorescence material, a delayed fluorescence material, or a combination thereof.

[0165] In the present specification, an emitter is a material that receives excitons from a host, a sensitizer, and / or a co-dopant and emits light through exciton transition to the ground state.

[0166] In the first embodiment and the second embodiment, based on 100 parts by weight of the emission layer, the amount of the polycyclic compound may be about 0.01 part by weight to about 40 parts by weight, about 0.1 part by weight to about 20 parts by weight, or about 1 part by weight to about 20 parts by weight.

[0167] The organometallic compound in the first embodiment and the second embodiment includes a transition metal and n ligands bonded to the transition metal, and n may be an integer from 1 to 4.

[0168] According to an embodiment, with respect to the organometallic compound, the transition metal may be platinum (Pt) or palladium (Pd), n may be 1, and the ligand may be a tetradentate ligand. The tetradentate ligand may include, for example, a carbene moiety bonded to the transition metal.

[0169] In some embodiments, the organometallic compound includes a transition metal and a tetradentate ligand bonded to the transition metal, the transition metal may be platinum or palladium, and the tetradentate ligand may include a carbene moiety bonded to the transition metal.

[0170] In some embodiments, with respect to the organometallic compound, the transition metal may be iridium (Ir) or osmium (Os), n may be 3, and at least one of the n ligands may be a bidentate ligand including -F, a cyano group, or a combination thereof, or a bidentate ligand including a carbene moiety bonded to the transition metal. For example, the bidentate ligand may further include an imidazole group or a triazole group.

[0171] In some embodiments, the organometallic compound may be the organometallic compound represented by Formula 3 and / or the organometallic compound represented by Formula 5 described herein. Details of Formulas 3 and 5 will be provided below.

[0172] The delayed fluorescence material in the first embodiment and the second embodiment may be, for example, a thermally activated delayed fluorescence material. As another example, the delayed fluorescence material may be a multi-resonant thermally activated delayed fluorescence material.

[0173] The multi-resonant thermally activated delayed fluorescence material may be i) free of a transition metal, and ii) a polycyclic compound having a core in which two or more C3-C 60 cyclic groups are fused to each other. In this regard, two C3-C 60 cyclic groups of the core may be fused to each other while sharing boron (B) or nitrogen (N).

[0174] According to an embodiment, the delayed fluorescence material may be a polycyclic compound represented by the following Formula 4. Details of Formula 4 will be provided below.

[0175] The transient fluorescent materials in the first and second embodiments may be amino-containing compounds, styryl-containing compounds, etc. For example, the transient fluorescent materials may include naphthalene groups, fluorene groups, spirobifluorene groups, benzofluorene groups, dibenzofluorene groups, phenanthrene groups, anthracene groups, fluoranthene groups, benzo[9,10]phenanthrene groups, pyrene groups, groups, tetracene groups (naphthacene groups), picene groups, perylene groups, pentaphene groups, indenoanthracene groups, groups represented by any one of Formulas 501-1 to 501-21, or combinations thereof:

[0176]

[0177] In some embodiments, the transient fluorescent material may include a compound represented by Formula 501A or 501B:

[0178]

[0179] Wherein, in Formulas 501A and 501B,

[0180] Ar 501 may be a naphthalene group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, groups, a tetracene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a bianthracene group, or a group represented by any one of Formulas 501-1 to 501-21,

[0181] R 511 may be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused polycyclic group, or -Si(Q 501 )(Q 502 )(Q 503 ),

[0182] xd5 can be an integer from 0 to 10,

[0183] L 501 to L 503 can each independently be:

[0184] a single bond; and

[0185] each unsubstituted or substituted by the following C3-C 10 cycloalkylidene, C1-C 10 heterocycloalkylidene, C3-C 10 cycloalkenylidene, C1-C 10 heterocycloalkenylidene, C6-C 60 arylidene, C1-C 60 heteroarylidene, a divalent non-aromatic fused polycyclic group, or a divalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxy, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, -Si(Q 501 )(Q 502 )(Q 503 ), or a combination thereof,

[0186] xd1 to xd3 can each independently be 1, 2, or 3,

[0187] R 501 and R 502 can each independently be phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, or dibenzosilolyl: deuterium, -F, -Cl, -Br, -I, hydroxy, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, C1-C60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C2-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 501 )(Q 502 )(Q 503 ), or any combination thereof,

[0188] Z 11 can be C1-C each unsubstituted or substituted by the following 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q501 )(Q 502 )(Q 503 ) or any combination thereof,

[0189] xd4 can be 1, 2, 3, 4, 5 or 6, and

[0190] Q 501 to Q 503 can each independently be selected from hydrogen, C1-C 60 alkyl, C1-C 60 alkoxy, C6-C 60 aryl, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group.

[0191] In some embodiments, the transient fluorescent material includes a compound represented by Formula 501A or 501B, wherein xd4 in Formula 501A can be 1, 2, 3, 4, 5 or 6, and xd4 in Formula 501B can be 2, 3 or 4.

[0192] Description of the host

[0193] The emission layer may include m1 hosts, and the m1 hosts may include a hole transport compound, an electron transport compound, a bipolar compound, or a combination thereof. Each of the m1 hosts may not include a transition metal.

[0194] For example, m1 in the emission layer is 2, and the two hosts in the emission layer may be a hole transport compound and an electron transport compound respectively, and the hole transport compound and the electron transport compound may be different from each other.

[0195] According to an embodiment, the hole transport compound may be a compound including at least one π-electron-rich C3-C 60 cyclic group and not including an electron transport group. Examples of electron transport groups are a cyano group, a fluorine group (-F), a cyclic group including π-electron-deficient nitrogen, a phosphine oxide group, a sulfoxide group, etc.

[0196] As used herein, the term "cyclic group including π-electron-deficient nitrogen" may be a C1-C 60 heterocyclic group having at least one *-N=*' moiety as a ring-forming moiety. Examples of cyclic groups including π-electron-deficient nitrogen may include a triazine group, an imidazole group, etc.

[0197] As used herein, the term "π-electron-rich C3-C 60 cyclic group" may be a C3-C 60 cyclic group not including a *-N=*' moiety as a ring-forming moiety. The π-electron-rich C3-C 60Examples of the cyclic group include a benzene group, a naphthalene group, a benzo[9,10]phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indolodibenzofuran group, an indolodibenzothiophene group, an indolocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrenobenzofuran group, a phenanthrenobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, or a dibenzocarbazole group.

[0198] For example, the hole transporting compound may include two or more carbazole groups.

[0199] In some embodiments, the electron transporting compound may include at least one electron transporting group. The electron transporting group may be a cyano group, a fluorine group, a C1-C cyclic group including electron-deficient π electrons, a phosphine oxide group, a sulfoxide group, or a combination thereof. According to an embodiment, the electron transporting compound may include a triazine group. 60 The cyclic group, a phosphine oxide group, a sulfoxide group, or a combination thereof. According to an embodiment, the electron transporting compound may include a triazine group.

[0200] For example, the electron transporting compound may include: at least one electron transporting group (e.g., a triazine group); and at least one π-electron-rich C3-C cyclic group (e.g., a benzene group, a naphthalene group, a benzo[9,10]phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indolodibenzofuran group, an indolodibenzothiophene group, an indolocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrenobenzofuran group, a phenanthrenobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzocarbazole group, or a combination thereof). 60 The cyclic group, a phosphine oxide group, a sulfoxide group, or a combination thereof. According to an embodiment, the electron transporting compound may include a triazine group.

[0201] For example, m1 in the emission layer may be 2, the two hosts in the emission layer may be a hole transporting compound and an electron transporting compound respectively, the hole transporting compound may be H1, and the electron transporting compound may be H2:

[0202]

[0203] The ratio of H1 to H2 (e.g., weight ratio) may be from about 80:20 to about 20:80, such as from about 70:30 to about 30:70, or from about 60:40 to about 40:60.

[0204] According to an embodiment, the hole transporting compound may be a compound represented by Formula 6:

[0205] Formula 6

[0206]

[0207] In Formula 6,

[0208] L 61and L 62 may each independently be an unsubstituted or substituted π - electron - rich C3 - C 60 cyclic group: deuterium, C1 - C 20 alkyl, deuterated C1 - C 20 alkyl, phenyl, deuterated phenyl, (C1 - C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, (C1 - C 20 alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or a combination thereof,

[0209] e61 and e62 may each independently be an integer from 1 to 6,

[0210] R 61 to R 64 may each independently be:

[0211] hydrogen, deuterium, C1 - C 20 alkyl, or deuterated C1 - C 20 alkyl;

[0212] an unsubstituted or substituted π - electron - rich C3 - C 60 cyclic group: deuterium, C1 - C 20 alkyl, deuterated C1 - C 20 alkyl, phenyl, deuterated phenyl, (C1 - C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, (C1 - C 20 alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or a combination thereof, or

[0213] -Si(Q3)(Q4)(Q5), and

[0214] a63 and a64 may each independently be an integer from 0 to 7.

[0215] Q3 to Q5 and Q 33 to Q 35 are each as described herein.

[0216] In some embodiments, the hole - transporting compound may be a compound represented by Formula 6 - 1, 6 - 2, or 6 - 3:

[0217] Formula 6 - 1

[0218]

[0219] Formula 6 - 2

[0220]

[0221] Formula 6-3

[0222]

[0223] Wherein, in Formulas 6-1 to 6-3, L 61 、L 62 、R 61 to R 64 、e61, e62, a63 and a64 are respectively the same as those described herein.

[0224] In some embodiments, the hole transporting compound can be one of Compounds HTH1 to HTH6:

[0225]

[0226] In some embodiments, the electron transporting compound can be a compound represented by Formula 7:

[0227] Formula 7

[0228]

[0229] Wherein, in Formula 7,

[0230] X 74 can be C(R 74 ) or N, X 75 can be C(R 75 ) or N, X 76 can be C(R 76 ) or N, and at least one of X 74 to X 76 is N,

[0231] L 71 to L 73 can each independently be a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group, unsubstituted or substituted with the following: deuterium, -F, cyano, C1-C 20 alkyl, deuterated C1-C 20 alkyl, fluorinated C1-C 20 alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or a combination thereof,

[0232] e71 to e73 can each independently be an integer from 1 to 10,

[0233] R 71 to R 76 can each independently be:

[0234] hydrogen, deuterium, -F, or cyano;

[0235] a C1-C 20 alkyl group that is unsubstituted or substituted with deuterium, -F, cyano, or a combination thereof;

[0236] a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group that is each unsubstituted or substituted with: deuterium, -F, cyano, a C1-C 20 alkyl group, a deuterated C1-C 20 alkyl group, a fluorinated C1-C 20 alkyl group, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 )), or a combination thereof; or

[0237] -Si(Q3)(Q4)(Q5).

[0238] Q3 to Q5 and Q 33 to Q 35 are each as described herein.

[0239] In some embodiments, X in Formula 7 74 to X 76 can each be N.

[0240] In some embodiments, L in Formula 7 71 to L 73 can each independently be a phenyl group, a naphthyl group, a benzo[9,10]phenanthryl group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indolodibenzofuran group, an indolodibenzothiophene group, an indolocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrenobenzofuran group, a phenanthrenobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, or a dibenzocarbazole group that is each unsubstituted or substituted with: deuterium, -F, cyano, a C1-C 20 alkyl group, a deuterated C1-C 20 alkyl group, a fluorinated C1-C 20 alkyl group, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or a combination thereof.

[0241] In some embodiments, in Formula 7, at least one of e71 L 71 , at least one of e72 L 72 , at least one of e73 L 73 , or a combination thereof may each independently be a dibenzofuran group, dibenzothiophene group, carbazole group, indolodibenzofuran group, indolodibenzothiophene group, indolocarbazole group, naphthobenzofuran group, naphthobenzothiophene group, benzocarbazole group, phenanthrenobenzofuran group, phenanthrenobenzothiophene group, naphthocarbazole group, dinaphthofuran group, dinaphthothiophene group, or dibenzocarbazole group, each unsubstituted or substituted with: deuterium, -F, cyano, C1-C 20 alkyl, deuterated C1-C 20 alkyl, fluorinated C1-C 20 alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or a combination thereof.

[0242] In some embodiments, in Formula 7, at least one of e71 L 71 , at least one of e72 L 72 , at least one of e73 L 73 , or a combination thereof may be a carbazole group, indolocarbazole group, benzocarbazole group, naphthocarbazole group, or dibenzocarbazole group, each having a nitrogen atom attached to a carbon atom of the 6-membered ring including X 71 to X 72 and / or L 73 in Formula 7 via a single bond or adjacent L 74 to X 76 .

[0243] In some embodiments, e71 to e73 in Formula 7 respectively represent the number of L 71 to the number of L 73 , and may each independently be, for example, 1, 2, 3, 4, or 5.

[0244] In some embodiments, R in Formula 771 to R 76 may each independently be:

[0245] hydrogen, deuterium, -F, or cyano;

[0246] C1-C that is unsubstituted or substituted with deuterium, -F, cyano, or a combination thereof 20 alkyl;

[0247] a phenyl group, a naphthyl group, a benzo[9,10]phenanthryl group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indolodibenzofuran group, an indolodibenzothiophene group, an indolocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrenobenzofuran group, a phenanthrenobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, or a dibenzocarbazole group, each of which is unsubstituted or substituted with: deuterium, -F, cyano, C1-C 20 alkyl, deuterated C1-C 20 alkyl, fluorinated C1-C 20 alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 )), or a combination thereof; or

[0248] -Si(Q3)(Q4)(Q5).

[0249] In some embodiments, the electron transport compound may be one of compounds ETH1 to ETH7:

[0250]

[0251] Description of Formula 3

[0252] The organometallic compounds in the first embodiment and the second embodiment may be organometallic compounds represented by Formula 3:

[0253] Formula 3

[0254]

[0255] wherein, in Formula 3,

[0256] M 31 may be a transition metal,

[0257] X 11 to X 14 may each independently be C or N,

[0258] X 11 and M 31 between the bond, X 12 and M 31 between the bond, X 13 and M 31 between the bond, and X 14 and M 31 between the two bonds of the bond may each be a coordination bond, and the other two bonds may each be a covalent bond,

[0259] Ring CY 31 to ring CY 34 may each independently be a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group,

[0260] T 31 may be a single bond, a double bond, *-N(R 35a ))-*', *-B(R 35a ))-*', *-P(R 35a ))-*', *-C(R 35a )(R 35b ))-*', *-Si(R 35a )(R 35b ))-*', *-Ge(R 35a )(R 35b ))-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 35a ))=*', *=C(R 35a ))-*', *-C(R 35a ))=C(R 35b ))-*', *-C(=S)-*', *-C≡C-*', unsubstituted or substituted with at least one R 10a carbocyclic group, or unsubstituted or substituted with at least one R 30 heterocyclic group, 10a substituted C1-C 30 heterocyclic group,

[0261] T 32 may be a single bond, a double bond, *-N(R 36a ))-*', *-B(R 36a ))-*', *-P(R 36a ))-*', *-C(R 36a )(R 36b )-*', *-Si(R 36a )(R 36b )-*', *-Ge(R 36a)(R 36b )-*'、*-S-*'、*-Se-*'、*-O-*'、*-C(=O)-*'、*-S(=O)-*'、*-S(=O)2-*'、*-C(R 36a )=*'、*=C(R 36a )-*'、*-C(R 36a )=C(R 36b )-*'、*-C(=S)-*'、*-C≡C-*'、unsubstituted or substituted by at least one R 10a substituted C5-C 30 carbocyclic group, or unsubstituted or substituted by at least one R 10a substituted C1-C 30 heterocyclic group,

[0262] T 33 can be a single bond, a double bond, *-N(R 37a )-*'、*-B(R 37a )-*'、*-P(R 37a )-*'、*-C(R 37a )(R 37b )-*'、*-Si(R 37a )(R 37b )-*'、*-Ge(R 37a )(R 37b )-*'、*-S-*'、*-Se-*'、*-O-*'、*-C(=O)-*'、*-S(=O)-*'、*-S(=O)2-*'、*-C(R 37a )=*'、*=C(R 37a )-*'、*-C(R 37a )=C(R 37b )-*'、*-C(=S)-*'、*-C≡C-*'、unsubstituted or substituted by at least one R 10a substituted C5-C 30 carbocyclic group, or unsubstituted or substituted by at least one R 10a substituted C1-C 30 heterocyclic group,

[0263] T 34 can be a single bond, a double bond, *-N(R 38a )-*'、*-B(R 38a )-*'、*-P(R 38a )-*'、*-C(R 38a )(R 38b )-*'、*-Si(R 38a )(R 38b )-*'、*-Ge(R 38a )(R38b )-*', *-S-*, *-Se-*, *-O-*, *-C(=O)-*, *-S(=O)-*, *-S(=O)2-*, *-C(R 38a )=*, *=C(R 38a )-*, *-C(R 38a )=C(R 38b )-*, *-C(=S)-*, *-C≡C-*, unsubstituted or substituted by at least one R 10a substituted C5-C 30 carbocyclic group, or unsubstituted or substituted by at least one R 10a substituted C1-C 30 heterocyclic group,

[0264] n31 to n34 can each independently be an integer from 0 to 5, and three or more of n31 to n34 can each independently be an integer from 1 to 5,

[0265] when n31 is 0, T 31 may not exist, when n32 is 0, T 32 may not exist, when n33 is 0, T 33 may not exist, and when n34 is 0, T 34 may not exist,

[0266] when n31 is 2 or greater, two or more Ts 31 may be the same as or different from each other, when n32 is 2 or greater, two or more Ts 32 may be the same as or different from each other, when n33 is 2 or greater, two or more Ts 33 may be the same as or different from each other, and when n34 is 2 or greater, two or more Ts 34 may be the same as or different from each other,

[0267] R 31 to R 34 、R 35a 、R 35b 、R 36a 、R 36b 、R 37a 、R 37b 、R 38a and R 38b can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -SF5, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0268] a31 to a34 can each independently be an integer from 0 to 20,

[0269] a31 R 31 Two or more of which may optionally be bonded to each other to form an unsubstituted or at least one R 10a Substituted C5-C 30 Carbocyclic group or unsubstituted or at least one R 10a Substituted C1-C 30 Heterocyclic group,

[0270] a32 R 32 Two or more of which may optionally be bonded to each other to form an unsubstituted or at least one R 10a Substituted C5-C 30 Carbocyclic group or unsubstituted or at least one R 10a Substituted C1-C 30 Heterocyclic group,

[0271] a33 R 33 Two or more of which may optionally be bonded to each other to form an unsubstituted or at least one R 10a Substituted C5-C 30 Carbocyclic group or unsubstituted or at least one R 10a Substituted C1-C 30Heterocyclic group,

[0272] Thirty-four Rs 34 Two or more of which may optionally be bonded to each other to form an unsubstituted or at least one R 10a Substituted C5-C 30 Carbocyclic group or an unsubstituted or at least one R 10a Substituted C1-C 30 Heterocyclic group,

[0273] R 31 To R 34 、R 35a 、R 35b 、R 36a 、R 36b 、R 37a 、R 37b 、R 38a And R 38b Two or more of which may optionally be bonded to each other to form an unsubstituted or at least one R 10a Substituted C5-C 30 Carbocyclic group or an unsubstituted or at least one R 10a Substituted C1-C 30 Heterocyclic group,

[0274] R 10a Is the same as that described for R 31 As described,

[0275] * and *' each represent a binding site to an adjacent atom,

[0276] Substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C2-C 60 The substituents of heteroarylalkyl, substituted monovalent non-aromatic fused polycyclic groups and substituted monovalent non-aromatic fused heteropolycyclic groups may be:

[0277] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy,

[0278] each C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -Ge(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ), or a combination thereof;

[0279] each unsubstituted or substituted by the following C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 23 )、-Si(Q 23 )(Q 24 )(Q 25 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 )、or a combination thereof;

[0280] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 )、or -P(Q 38 )(Q 39 ); or

[0281] Its combination, and

[0282] Q1 to Q9, Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, unsubstituted or substituted by deuterium, C1-C 60 alkyl, C6-C 60 aryl, or a combination thereof-substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, unsubstituted or substituted by deuterium, C1-C 60 alkyl, C6-C 60 aryl, or a combination thereof-substituted C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group.

[0283] According to an embodiment, M in Formula 3 31 can be Pt, Pd or Au.

[0284] In some embodiments, M in Formula 3 31 can be Pt or Pd.

[0285] In some embodiments, the bond between X 11 and M 31 in Formula 3 can be a coordination bond.

[0286] In one or more embodiments, in Formula 3, X 11 can be C, and the bond between X 11 and M 31 can be a coordination bond. That is, X 11 in Formula 3 can be the C in the carbene moiety.

[0287] In one or more embodiments, ring CY in Formula 3 31 to ring CY 34may each independently be i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused to each other, iv) a fused ring in which two or more second rings are fused to each other, or v) a fused ring in which at least one first ring is fused to at least one second ring,

[0288] wherein the first ring may be a cyclopentyl group, a cyclopentadienyl group, a furan group, a thiophene group, a pyrrole group, a silole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an aza-silole group, a diaza-silole group, or a triaza-silole group, and

[0289] the second ring may be an adamantyl group, a norbornyl group, a norbornene group, a cyclohexyl group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, an oxazine group, a thiazine group, a dihydropyrazine group, a dihydropyridine group, or a dihydroazasilane group.

[0290] According to an embodiment, R 31 to R 34 、R 35a 、R 35b 、R 36a 、R 36b 、R 37a 、R 37b 、R 38a and R 38b may each independently be:

[0291] hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano (CN), nitro, amino, C1-C 20 alkyl, or C1-C 20 alkoxy;

[0292] C1-C 20 alkyl or C1-C 20 alkoxy each substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano (CN), nitro, amino, and phenyl; or

[0293] A cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, or anthracenyl group, each unsubstituted or substituted by at least one of the following: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano (CN), nitro, amino, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, and anthracenyl.

[0294] According to an embodiment, the organometallic compound represented by Formula 3 may be an organometallic compound represented by Formula 3-1 or an organometallic compound represented by Formula 3-2:

[0295] Formula 3-1

[0296] and

[0297] Formula 3-2

[0298]

[0299] The bond between the carbon of the imidazole group in Formula 3-1 and M 31 may be a coordination bond. That is, the imidazole group in Formula 3-1 may include a carbene moiety bonded to M 31 .

[0300] The bond between the carbon of the benzimidazole group in Formula 3-2 and M 31 may be a coordination bond. That is, the benzimidazole group in Formula 3-2 includes a carbene moiety bonded to M 31 .

[0301] Wherein, in Formulas 3-1 and 3-2,

[0302] M 31 , CY 32 , CY 33 , CY 34 , X 12 , X 13 , X 14 , T 31 , T 32 , T 33 , n31, n32, n33, R 32 , R 33 , R 34 , a32, a33, and a34 may be respectively determined by referring to M provided herein 31 , CY 32 , CY 33 , CY 34, X 12 , X 13 , X 14 , T 31 , T 32 , T 33 , n31, n32, n33, R 32 , R 33 , R 34 , the descriptions of a32, a33, and a34, and

[0303] , R 311 to R 317 can each be understood by referring to the description of R provided herein 31 .

[0304] In an embodiment, in Formulas 3-1 and 3-2,

[0305] , R 311 to R 317 can each independently be:

[0306] hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -SF5, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a phosphoric acid group or a salt thereof;

[0307] a C1-C 20 alkyl or a C1-C 20 alkoxy that is each unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -SF5, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, or a combination thereof;

[0308] a C3-C 10 cycloalkyl, a C1-C 10 heterocycloalkyl, a C6-C 60 aryl, a C7-C 60 arylalkyl, a C6-C 60 aryloxy, a C6-C 60 arylthio, a C1-C 60 heteroaryl, a C2-C 60 heteroarylalkyl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -SF5, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, a C1-C 20 alkyl, a C1-C 20an alkoxy group, or a combination thereof; or

[0309] -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9).

[0310] For example, in Formulas 3-1 and 3-2,

[0311] R 311 to R 317 at least one of which may be

[0312] each unsubstituted or substituted with at least one of the following C1-C 20 alkyl group, C6-C 60 aryl group, or C7-C 60 arylalkyl group: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl, cumyl (isopropylphenyl), or a combination thereof.

[0313] Description of Formula 5

[0314] The organometallic compound in the first embodiment and the second embodiment may be an organometallic compound represented by Formula 5:

[0315] Formula 5

[0316] M 51 (L 51 ) n51 (L 52 ) n52

[0317] M in Formula 5 51 may be a transition metal.

[0318] In an embodiment, M 51 may be a first-row transition metal, a second-row transition metal, or a third-row transition metal of the periodic table.

[0319] In one or more embodiments, M 51 may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0320] In one or more embodiments, M 51 may be Ir, Pt, Os, or Rh.

[0321] In some embodiments, M 51 may be Ir or Os.

[0322] In Formula 5, L51 can be a ligand represented by Formula 5A, and L 52 can be a ligand represented by Formula 5B:

[0323]

[0324] wherein Formula 5A and 5B are each the same as those described in this specification.

[0325] n51 in Formula 5 can be 1, 2, or 3, wherein when n51 is 2 or greater, two or more L 51 can be the same as or different from each other.

[0326] n52 in Formula 5 can be 0, 1, or 2, wherein when n52 is 2, the two L 52 can be the same as or different from each other.

[0327] The sum of n51 and n52 in Formula 5 can be 2 or 3. For example, the sum of n51 and n52 can be 3.

[0328] In an embodiment, in Formula 5, i) M can be Ir, and n51 + n52 = 3; or ii) M can be Pt, and n51 + n52 = 2.

[0329] In one or more embodiments, in Formula 5, M can be Ir, and i) n51 can be 1 and n52 can be 2, or ii) n51 can be 2 and n52 can be 1.

[0330] L in Formula 5 51 and L 52 can be different from each other.

[0331] Y in Formulas 5A to 5B 51 to Y 54 can each independently be C or N. For example, Y 51 and Y 53 can each be N, and Y 52 and Y 54 can each be C.

[0332] The ring CY in Formulas 5A and 5B 51 to the ring CY 54 can each independently be a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group.

[0333] For example, the ring CY in Formulas 5A and 5B 51 to the ring CY 54 can each independently include (or be) i)

[0334] the third ring, ii) the fourth ring, iii) a fused ring in which two or more of the third rings are fused to each other, iv) a fused ring in which two or more of the fourth rings are fused to each other, or v) a fused ring in which at least one of the third rings is fused to at least one of the fourth rings,

[0335] wherein the third ring can be a cyclopentyl group, a cyclopentenyl group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an aza-silole group, and

[0336] the fourth ring can be an adamantyl group, a norbornyl group, a norbornene group, a cyclohexyl group, a cyclohexenyl group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0337] In some embodiments, in Formulas 5A and 5B, ring CY1 to ring CY4 can each independently be a cyclopentyl group, a cyclohexyl group, a cyclohexenyl group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, pyrrole group, furan group, thiophene group, silole group, borole group, phosphole group, germole group, selenophene group, indene group, indole group, benzofuran group, benzothiophene group, benzosilole group, benzoborole group, benzophosphole group, benzogermole group, benzoselenophene group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilole group, dibenzoborole group, dibenzophosphole group, dibenzogermole group, dibenzoselenophene group, benzofluoren group, benzocarbazole group, naphthobenzofuran group, naphthobenzothiophene group, naphthobenzosilole group, naphthobenzoborole group, naphthobenzophosphole group, naphthobenzogermole group, naphthobenzoselenophene group, dibenzofluoren group, dibenzocarbazole group, dinaphthofuran group, dinaphthothiophene group, dinaphthosilole group, dinaphthoborole group, dinaphthophosphole group, dinaphthogermole group, dinaphthoselenophene group, indeno[1,2,3-cd]pyrene group, indolo[1,2,3-cd]pyrene group, phenanthro[9,10-b]benzofuran group, phenanthro[9,10-b]benzothiophene group, phenanthro[9,10-b]benzosilole group, phenanthro[9,10-b]benzoborole group, phenanthro[9,10-b]benzophosphole group, phenanthro[9,10-b]benzogermole group, phenanthro[9,10-b]benzoselenophene group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, indolizine group, indole group, benzofuran group, benzothiophene group, benzosilole group, benzoborole group, benzophosphole group, benzogermole group, benzoselenophene group, azafluorene group, azacarbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilole group, dibenzoborole group, dibenzophosphole group, dibenzogermole group, dibenzoselenophene group, benzoazafluorene group, benzoazacarbazole group, naphthobenzofuran group, naphthobenzothiophene group, naphthobenzosilole group, naphthobenzoborole group, naphthobenzophosphole group, naphthobenzogermole group, naphthobenzoselenophene group, dibenzoazafluorene group, dibenzoazacarbazole group, dinaphthofuran group, dinaphthothiophene group, dinaphthosilole group, dinaphthoborole group, dinaphthophosphole group, dinaphthogermole group, dinaphthoselenophene group, indeno[1,2,3-cd]pyrene group, indolo[1,2,3-cd]pyrene group, phenanthro[9,10-b]furan group, phenanthro[9,10-b]thiophene group, phenanthro[9,10-b]silole group, phenanthro[9,10-b]borole group, phenanthro[9,10-b]phosphole group, phenanthro[9,10-b]germole group, phenanthro[9,10-b]selenophene group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, benzoquinoline group, benzoisoquinoline group, benzoquinoxaline group, benzoquinazoline group, phenanthroline group, phenanthridine group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, azasilole group, azaborole group, azaphosphole group, azagermole group, azaselenophene group, benzopyrrole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, benzoxadiazole group, benzothiadiazole group, pyrido[2,3-b]pyrrole group, pyrido[2,3-b]pyrazole group, pyrido[2,3-b]imidazole group, pyrido[2,3-b]oxazole group, pyrido[2,3-b]isoxazole group, pyrido[2,3-b]thiazole group, pyrido[2,3-b]isothiazole group, pyrido[2,3-b]oxadiazole group, pyrido[2,3-b]thiadiazole group, pyrimido[4,5-b]pyrrole group, pyrimido[4,5-b]pyrazole group, pyrimido[4,5-b]imidazole group, pyrimido[4,5-b]oxazole group, pyrimido[4,5-b]isoxazole group, pyrimido[4,5-b]thiazole group, pyrimido[4,5-b]isothiazole group, pyrimido[4,5-b]oxadiazole group, pyrimido[4,5-b]thiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinolinyl group, adamantyl group, norbornyl group, norbornenyl group, benzene group fused with cyclohexyl group, benzene group fused with norbornyl group, pyridine group fused with cyclohexyl group, or pyridine group fused with norbornyl group.,

[0338] For example, ring CY in Formulas 5A and 5B 51 and ring CY 53 may be different from each other.

[0339] In one or more embodiments, ring CY in Formulas 5A and 5B 52 and ring CY 54 may be different from each other.

[0340] In one or more embodiments, ring CY in Formulas 5A and 5B 51 to ring CY 54 may be different from each other.

[0341] R in Formulas 5A and 5B 51 to R 54 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 alkynyl, substituted or unsubstituted C1-C 60 alkoxy, substituted or unsubstituted C1-C 60 alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 heterocycloalkyl, substituted or unsubstituted C3-C 10 cycloalkenyl, substituted or unsubstituted C1-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q 51 )(Q 52 ), -Si(Q 53 )(Q 54 )(Q 55 ), -Ge(Q 53 )(Q 54 )(Q 55), -B(Q 56 )(Q 57 ), -P(=O)(Q 58 )(Q 59 ), or -P(Q 58 )(Q 59 ). Q 51 to Q 59 are each the same as those described in this specification.

[0342] In an embodiment, R 51 to R 54 in Formulas 5A and 5B can each independently be:

[0343] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, -SF5, C1-C 20 alkyl, C1-C 20 alkoxy, or C1-C 20 alkylthio;

[0344] C1-C 20 alkyl, C1-C 20 alkoxy, or C1-C 20 alkylthio each substituted with the following: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 alkyl)adamantyl, (C1-C 20 alkyl)norbornyl, (C1-C 20 alkyl)norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 alkyl)bicyclo[1.1.1]pentyl, (C1-C 20(alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 (alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 (alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidyl, or a combination thereof;

[0345] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C1-C 20 (alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, (group), pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothienyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 (alkyl), (phenyl)C1-C 10 (alkyl), C1-C 20 (alkoxy), cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 (alkyl)cyclopentyl, (C1-C 20 (alkyl)cyclohexyl, (C1-C 20 (alkyl)cycloheptyl, (C1-C 20 (alkyl)cyclooctyl, (C1-C 20 (alkyl)adamantyl, (C1-C 20 (alkyl)norbornyl, (C1-C 20 (alkyl)norbornenyl, (C1-C 20 (alkyl)cyclopentenyl, (C1-C 20alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, or a combination thereof; or

[0346] -N(Q 51 )(Q 52 )、-Si(Q 53 )(Q 54 )(Q 55 )、-Ge(Q 53 )(Q 54 )(Q 55 )、-B(Q 56 )(Q 57 )、-P(=O)(Q 58 )(Q 59 ), or -P(Q 58 )(Q 59 ),

[0347] Where Q 51 To Q 59 Can be independently:

[0348] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or

[0349] n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl, each unsubstituted or substituted with: deuterium, C1-C 10 alkyl, phenyl, or a combination thereof.

[0350] In one or more embodiments, R 51 through R 54 can each independently be:

[0351] hydrogen, deuterium, -F, or cyano;

[0352] C1-C 20 alkyl, unsubstituted or substituted with: deuterium, cyano, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, fluorinated C3-C 10 cycloalkyl, (C1-C 20 alkyl)C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, deuterated C1-C 10 heterocycloalkyl, fluorinated C1-C 10 heterocycloalkyl, (C1-C 20 alkyl)C1-C 10 heterocycloalkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl)biphenyl, dibenzofuranyl, deuterated dibenzofuranyl, fluorinated dibenzofuranyl, (C1-C 20 alkyl)dibenzofuranyl, dibenzothiophenyl, deuterated dibenzothiophenyl, fluorinated dibenzothiophenyl, (C1-C 20 alkyl)dibenzothiophenyl, or any combination thereof;

[0353] C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, phenyl, or biphenyl, each unsubstituted or substituted with: deuterium, cyano, C1-C 20 alkyl, deuterated C1-C 20 alkyl, fluorinated C1-C 20 alkyl, C1-C 20 alkoxy, deuterated C1-C 20 alkoxy, fluorinated C1-C 20 alkoxy, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, fluorinated C3-C 10 cycloalkyl, (C1-C20 alkyl)C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, deuterated C1-C 10 heterocycloalkyl, fluorinated C1-C 10 heterocycloalkyl, (C1-C 20 alkyl)C1-C 10 heterocycloalkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C 20 alkyl)biphenyl, dibenzofuranyl, deuterated dibenzofuranyl, fluorinated dibenzofuranyl, (C1-C 20 alkyl)dibenzofuranyl, dibenzothiophenyl, deuterated dibenzothiophenyl, fluorinated dibenzothiophenyl, (C1-C 20 alkyl)dibenzothiophenyl, or a combination thereof; or

[0354] -Si(Q 53 )(Q 54 )(Q 55 ) or -Ge(Q 53 )(Q 54 )(Q 55 )。

[0355] In Formulas 5A and 5B, b51 to b54 each represent the number of R 51 to R 54 , and can each independently be an integer from 0 to 20. When b51 is 2 or greater, two or more R 51 can be the same as or different from each other. When b52 is 2 or greater, two or more R 52 can be the same as or different from each other. When b53 is 2 or greater, two or more R 53 can be the same as or different from each other, and when b54 is 2 or greater, two or more R 54 can be the same as or different from each other. For example, b51 to b54 can each independently be an integer from 0 to 8.

[0356] According to an embodiment, in Formula 5A, Y 52 can be C, the bond between Y 52 and M 51 can be a covalent bond, and at least one of the b52 R 52 can be cyano or -F.

[0357] In some embodiments, in Formula 5A, Y 51 can be N, the bond between Y 51 and M 51 can be a coordination bond, CY 51may be an imidazole group, a triazole group, a benzimidazole group, or a triazolopyridine group, and at least one of the b52 Rs 52 may be a cyano group or -F.

[0358] In some embodiments, in Formula 5A, Y 51 may be C, and the bond between Y 51 and M 51 may be a coordination bond.

[0359] In some embodiments, in Formula 5A, Y 51 may be C, the bond between Y 51 and M 51 may be a coordination bond, and CY 51 may be a benzimidazole group or an imidazopyrazine group.

[0360] Specific examples of the organometallic compound represented by Formula 3 or Formula 5 are described below.

[0361] For example, the organometallic compound represented by Formula 3 or Formula 5 may be one of Compounds P1 to P52:

[0362]

[0363]

[0364]

[0365] Description of Formula 4

[0366] The delayed fluorescence material in the first embodiment and the second embodiment may be a polycyclic compound represented by Formula 4:

[0367] Formula 4

[0368]

[0369] wherein, in Formula 4,

[0370] Z may be B or N,

[0371] Ring CY 41 to ring CY 43 may each independently be a C5-C 60 carbocyclic group or a C1-C 60 heterocyclic group,

[0372] Y 41 may be a single bond, *-N(R 44 )-*', *-B(R 44 )-*', *-P(R 44 )-*', *-C(R 44 )(R 45)-*'、*-Si(R 44 )(R 45 )-*'、*-Ge(R 44 )(R 45 )-*'、*-O-*'、*-S-*'、*-Se-*'、*-C(=O)-*'、 or *-S(=O)2-*',

[0373] Y 42 can be a single bond, *-N(R 46 )(R 46 )-*'、*-B(R 46 )-*'、*-P(R 46 )(R 47 )-*'、*-Si(R 46 )(R 47 )-*'、*-Ge(R 46 )(R 47 )-*'、*-O-*'、*-S-*'、*-Se-*'、*-C(=O)-*'、 or *-S(=O)2-*',

[0374] Y 43 can be a single bond, *-N(R 48 )(R 48 )-*'、*-B(R 48 )-*'、*-P(R 48 )(R 49 )-*'、*-Si(R 48 )(R 49 )-*'、*-Ge(R 48 )(R 49 )-*'、*-O-*'、*-S-*'、*-Se-*'、*-C(=O)-*'、 or *-S(=O)2-*',

[0375] b41 to b43 can each independently be 0 or 1,

[0376] when b41 is 0, Y 41 may not exist, when b42 is 0, Y 42 may not exist, and when b43 is 0, Y 43 may not exist,

[0377] R 41 to R 49 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0378] a41 to a43 can each independently be an integer from 0 to 20,

[0379] Two or more of the a41 Rs 41 may optionally be bonded to each other to form an unsubstituted or at least one R 10b substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 30 heterocyclic group,

[0380] Two or more of the a42 Rs 42 may optionally be bonded to each other to form an unsubstituted or at least one R 10b substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 30 heterocyclic group,

[0381] Two or more of the a43 Rs 43 may optionally be bonded to each other to form an unsubstituted or at least one R 10b substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10bSubstituted C1-C 30 heterocyclic group,

[0382] R 41 to R 49 two or more of which may optionally be bonded to each other to form an unsubstituted or at least one R 10b substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 30 heterocyclic group,

[0383] R 10b is the same as that described with respect to R 41 as described,

[0384] * and *' each represent a binding site to an adjacent atom,

[0385] Substituted C1-C 60 alkyl, substituted C2-C 60 alkenyl, substituted C2-C 60 alkynyl, substituted C1-C 60 alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 heterocycloalkyl, substituted C3-C 10 cycloalkenyl, substituted C1-C 10 heterocycloalkenyl, substituted C6-C 60 aryl, substituted C7-C 60 arylalkyl, substituted C6-C 60 aryloxy, substituted C6-C 60 arylthio, substituted C1-C 60 heteroaryl, substituted C2-C 60 The substituents of heteroarylalkyl, substituted monovalent non-aromatic fused polycyclic groups, and substituted monovalent non-aromatic fused heteropolycyclic groups may be:

[0386] deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy,

[0387] Each C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60alkynyl, or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 )、or a combination thereof;

[0388] Each of C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 10Naphthenyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 23 )、-Si(Q 23 )(Q 24 )(Q 25 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 )、or a combination thereof;

[0389] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 )、or -P(Q 38 )(Q 39 ); or

[0390] a combination thereof, and

[0391] Q1 to Q9, Q 11 to Q 19 、Q 21 to Q 29 、and Q 31 to Q 39 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, unsubstituted or substituted by deuterium, C1-C 60 alkyl, C6-C 60 aryl, or a combination thereof substituted C1-C 60Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one of deuterium, C1-C 60 alkyl, C6-C 60 aryl, or a combination thereof, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group.

[0392] According to an embodiment, ring CY 41 to ring CY 43 may each independently be: i) a benzene group, or ii) a polycyclic group in which two or more C3-C 30 ring groups are fused to each other. Two C3-C 30 ring groups in the polycyclic group may be fused to each other while sharing boron (B) or nitrogen (N).

[0393] In some embodiments, at least one of b41 to b43, or at least two of b41 to b43 may each be 1. In some embodiments, two of b41 to b43 may be 1, and the remaining one may be 0.

[0394] In some embodiments, R 41 to R 49 may each independently be:

[0395] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl, or C1-C 20 alkoxy;

[0396] C1-C 60 alkyl or C1-C 60 alkoxy each substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, and group; or

[0397] A cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, each of which is unsubstituted or substituted with at least one of the following: group, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, or carbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, C1-C 60 alkyl, C1-C 60 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, group, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, and carbazolyl.

[0398] In some embodiments, the polycyclic compound represented by Formula 4 may be a polycyclic compound represented by one of Formulas 4-1 to 4-9:

[0399] Formula 4-1

[0400]

[0401] Formula 4-2

[0402]

[0403] Formula 4-3

[0404]

[0405] Formula 4-4

[0406]

[0407] Formula 4-5

[0408]

[0409] Formula 4-6

[0410]

[0411] Formula 4-7

[0412]

[0413] Formula 4-8

[0414]

[0415] Formula 4-9

[0416]

[0417] Wherein, in Formulas 4-1 to 4-9,

[0418] Z1 to Z3 are each as described in the specification regarding Z,

[0419] Y 41 and Y 42 as described in this specification,

[0420] Y 44 to Y 47 respectively refer to the description of Y in this specification 41 and Y 42 for the description,

[0421] R 411 is the same as that described regarding R 41 R 421 is the same as that described regarding R 42 R 431 and R 432 are each the same as that described regarding R 43 R 441 is the same as that described regarding R 41 R 451 is the same as that described regarding R 42 and R 461 is the same as that described regarding R 43 for the description,

[0422] a411 can be an integer from 0 to 4,

[0423] a421 can be an integer from 0 to 3,

[0424] a431 can be an integer from 0 to 4,

[0425] a441 can be an integer from 0 to 4,

[0426] a451 can be an integer from 0 to 3, and

[0427] a461 is an integer from 0 to 3.

[0428] The polycyclic compound represented by Formula 4 may be selected from Compounds D1 to D30:

[0429]

[0430]

[0431]

[0432] Figure 1 is a schematic cross-sectional view of the organic light-emitting device 10 according to an embodiment. Hereinafter, reference will be made to Figure 1 describe the structure and manufacturing method of the organic light-emitting device 10 according to an embodiment.

[0433] Figure 1 The organic light-emitting device 10 includes a first electrode 11, a second electrode 19 facing the first electrode 11, and an intermediate layer 10A between the first electrode 11 and the second electrode 19.

[0434] The intermediate layer 10A includes an emission layer 15, and may further include a hole transport region 12 between the first electrode 11 and the emission layer 15, and an electron transport region 17 between the emission layer 15 and the second electrode 19.

[0435] A substrate may be further provided under the first electrode 11 or on the second electrode 19. The substrate may be a substrate commonly used in organic light-emitting devices, such as a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness.

[0436] The first electrode 11 may be formed by, for example, depositing or sputtering a material for forming the first electrode 11 onto the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may include a material having a high work function to facilitate hole injection.

[0437] The first electrode 11 can be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In an embodiment, when the first electrode 11 is a transmissive electrode, the material for forming the first electrode 11 can include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or a combination thereof. In one or more embodiments, when the first electrode 11 is a semi-transmissive electrode or a reflective electrode, the material for forming the first electrode 11 can include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or a combination thereof.

[0438] The first electrode 11 can have a single-layer structure or a multi-layer structure including two or more layers.

[0439] The thickness of the emission layer 15 can be in the range of about 100 angstroms to about 1,000 angstroms, for example, about 200 angstroms to about 600 angstroms. When the thickness of the emission layer is within the range described above, excellent light-emitting characteristics can be obtained without a significant increase in the driving voltage.

[0440] According to an embodiment, the emission layer 15 can include a polycyclic compound as described herein. The emission layer 15 can follow the first embodiment or the second embodiment described in this specification.

[0441] In addition to the polycyclic compound, sensitizer, and emitter as described herein, the emission layer 15 can further include a host as described herein.

[0442] The hole transport region 12 can be disposed between the first electrode 11 and the emission layer 15 of the organic light-emitting device 10.

[0443] The hole transport region 12 can have a single-layer structure or a multi-layer structure.

[0444] For example, the hole transport region 12 can have a hole injection layer, a hole transport layer, a hole injection layer / hole transport layer structure, a hole injection layer / first hole transport layer / second hole transport layer structure, a hole injection layer / first hole transport layer / second hole transport layer / electron blocking layer structure, a hole transport layer / buffer layer structure, a hole injection layer / hole transport layer / buffer layer structure, a hole transport layer / electron blocking layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure.

[0445] The hole transport region 12 can include any compound having hole transport properties.

[0446] For example, the hole transport region 12 can include an amine-based compound.

[0447] In an embodiment, the hole transport region 12 may include, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), one of the compounds represented by Formula 201 to Formula 205, or a combination thereof:

[0448]

[0449] Formula 201

[0450]

[0451] Formula 202

[0452]

[0453] Formula 203

[0454]

[0455] Formula 204

[0456]

[0457] Formula 205

[0458]

[0459] Wherein, in Formulas 201 to 205,

[0460] L 201 to L 209 may each independently be *-O-*', *-S-*', a substituted or unsubstituted C5-C 60 carbocyclic group, or a substituted or unsubstituted C1-C 60 heterocyclic group,

[0461] xa1 to xa9 may each independently be an integer from 0 to 5, and

[0462] R 201 to R 206 may each independently be a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C1-C 10 heterocycloalkyl, a substituted or unsubstituted C3-C 10Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein R 201 to R 206 Two adjacent groups may optionally be connected to each other via a single bond, dimethyl-methylene, or diphenyl-methylene.

[0463] In an embodiment,

[0464] L 201 to L 209 may each be a benzene group, heptalene group, indene group, naphthalene group, azulene group, indacene group, acenaphthene group, fluorene group, spirobifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, group, tetracene group, picene group, perylene group, pentaphene group, hexacene group, pentacene group, rubicene group, coronene group, ovalene group, pyrrole group, isoindole group, indole group, furan group, thiophene group, benzofuran group, benzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, dibenzosilole group, indacenocarbazole group, indolocarbazole group, benzofurancarbazole group, benzothiophenocarbazole group, or triindolobenzene group: deuterium, C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzo[9,10]phenanthryl, biphenyl, terphenyl, quaterphenyl, -Si(Q 11 )(Q 12 )(Q 13 ), or a combination thereof,

[0465] xa1 to xa9 may each independently be 0, 1, or 2, and

[0466] R 201 to R 206Each may independently be phenyl, biphenyl, terphenyl, cyclopentadienyl, indenyl, naphthyl, azulyl, heptaleneyl, indacenyl, acenaphthylenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, -yl, tetraphenylenyl, picenyl, perylenyl, pentaphenylenyl, hexaphenylenyl, pentacenyl, coronenyl, ovalenyl, thiophenyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridyl, indacarbazolyl, indolocarbazolyl, benzofurancarbazolyl, or benzothiophencarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, phenyl substituted with C1-C 10 alkyl, phenyl substituted with -F, cyclopentadienyl, indenyl, naphthyl, azulyl, heptaleneyl, indacenyl, acenaphthylenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, -yl, tetraphenylenyl, picenyl, perylenyl, pentaphenylenyl, hexaphenylenyl, pentacenyl, coronenyl, ovalenyl, thiophenyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), or a combination thereof.

[0467] Q 11 to Q 13 and Q 31 to Q 33 may each independently be C1-C 10 alkyl, C1-C 10 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.

[0468] In one or more embodiments, the hole transport region 12 may include a carbazole-containing amine-based compound.

[0469] In one or more embodiments, the hole transport region 12 may include a carbazole-containing amine-based compound and a carbazole-free amine-based compound.

[0470] The amine-based compounds containing carbazole may include, for example, compounds represented by Formula 201 that include a carbazole group and further include at least one of the following: a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spirobifluorene group, an indolocarbazole group, an indolocarbazole group, a benzofurocarbazole group, and a benzothienocarbazole group.

[0471] The amine-based compounds without carbazole may include, for example, compounds represented by Formula 201 that do not include a carbazole group and include at least one of the following: a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spirobifluorene group, an indolocarbazole group, an indolocarbazole group, a benzofurocarbazole group, and a benzothienocarbazole group.

[0472] In one or more embodiments, the hole transport region 12 may include a compound represented by Formula 201, a compound represented by Formula 202, or a combination thereof.

[0473] In one or more embodiments, the hole transport region 12 may include a compound represented by Formula 201-1, 202-1 or 201-2, or a combination thereof:

[0474] Formula 201-1

[0475]

[0476] Formula 202-1

[0477]

[0478] Formula 201-2

[0479]

[0480] Wherein, in Formulas 201-1, 202-1 and 201-2, L 201 to L 203 、L 205 、xa1 to xa3, xa5, R 201 and R 202 are each the same as described herein, and R 211 to R 213 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, substituted by C1-C 10An alkyl-substituted phenyl, a phenyl substituted with -F, a naphthyl, a fluorenyl, a spirobifluorenyl, a dimethylfluorenyl, a diphenylfluorenyl, a benzo[9,10]phenanthryl, a thienyl, a furyl, a carbazolyl, an indolyl, an isoindolyl, a benzofuranyl, a benzothienyl, a dibenzofuranyl, a dibenzothienyl, a benzocarbazolyl, a dibenzocarbazolyl, a dibenzosilolyl, or a pyridyl.

[0481] In an embodiment, the hole transport region 12 may include one of compounds HT1 to HT39, or a combination thereof:

[0482]

[0483]

[0484]

[0485]

[0486] In one or more embodiments, the hole transport region 12 of the organic light emitting device 10 may further include a p-dopant. When the hole transport region 12 further includes a p-dopant, the hole transport region 12 may have a matrix (e.g., at least one of the compounds represented by Formulas 201 to 205) and a p-dopant included in the matrix. The p-dopant may be doped in the hole transport region 12 uniformly or non-uniformly.

[0487] In an embodiment, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be about -3.5 eV or less.

[0488] The p-dopant may include a quinone derivative, a metal oxide, a cyanide-containing compound, or a combination thereof.

[0489] For example, the p-dopant may include:

[0490] Quinone derivatives such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), and F6-TCNNQ;

[0491] Metal oxides such as tungsten oxide or molybdenum oxide;

[0492] 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile (HAT-CN);

[0493] A compound represented by Formula 221; or

[0494] A combination thereof:

[0495]

[0496] Formula 221

[0497]

[0498] Wherein, in Formula 221,

[0499] R 221 to R 223 may each independently be a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C1-C 10 heterocycloalkyl, a substituted or unsubstituted C3-C 10 cycloalkenyl, a substituted or unsubstituted C1-C 10 heterocycloalkenyl, a substituted or unsubstituted C6-C 60 aryl, a substituted or unsubstituted C1-C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein R 221 to R 223 at least one substituent may be: cyano; -F; -Cl; -Br; -I; a C1-C 20 alkyl substituted with -F; a C1-C 20 alkyl substituted with -Cl; a C1-C 20 alkyl substituted with -Br; a C1-C 20 alkyl substituted with -I; or a combination thereof.

[0500] The compound represented by Formula 221 may include, for example, compound HT-D2:

[0501]

[0502] The hole transport region 12 may have a thickness in the range of about to about For example, about to about and the emission layer 15 may have a thickness in the range of about to about For example, about to about When the thicknesses of the hole transport region 12 and the emission layer 15 are each within these ranges, satisfactory hole transport characteristics and / or light emission characteristics can be obtained without a significant increase in the driving voltage.

[0503] The hole transport region 12 may further include a buffer layer.

[0504] The buffer layer may compensate for the optical resonance distance according to the wavelength of the light emitted from the emission layer 15, and thus, the efficiency of the formed organic light-emitting device can be improved.

[0505] The hole transport region 12 may further include an electron blocking layer. The electron blocking layer may include known materials, such as mCP or DBFPO:

[0506]

[0507] The electron transport region 17 is disposed between the emission layer 15 and the second electrode 19 of the organic light emitting device 10.

[0508] The electron transport region 17 may have a single-layer structure or a multi-layer structure.

[0509] For example, the electron transport region 17 may have an electron transport layer, an electron transport layer / electron injection layer structure, a buffer layer / electron transport layer structure, a hole blocking layer / electron transport layer structure, a buffer layer / electron transport layer / electron injection layer structure, or a hole blocking layer / electron transport layer / electron injection layer structure. The electron transport region 17 may further include an electron control layer.

[0510] The electron transport region 17 may include known electron transport materials.

[0511] The electron transport region 17 (e.g., the buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include the following metal-free compounds: which contain at least one C1-C 60 cyclic group containing nitrogen with deficient π electrons. The C1-C 60 cyclic group containing nitrogen with deficient π electrons is the same as that described herein.

[0512] For example, the electron transport region 17 may include a compound represented by Formula 601:

[0513] Formula 601

[0514] [Ar 601 xe11 -[(L 601 ) xe1 -R 601 xe21 .

[0515] In Formula 601,

[0516] Ar 601 and L 601 may each independently be an unsubstituted or at least one R 601a substituted C5-C 60 carbocyclic group or an unsubstituted or at least one R 601a substituted C1-C 60 heterocyclic group,

[0517] xe11 may be 1, 2 or 3, ​​

[0518] xe1 can be an integer from 0 to 5,

[0519] R 601a and R 601 can each independently be a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), or -P(=O)(Q 601 )(Q 602 ),

[0520] Q 601 to Q 603 can each independently be a C1-C 10 alkyl group, a C1-C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and

[0521] xe21 can be an integer from 1 to 5.

[0522] In an embodiment, at least one of xe11 Ar 601 and xe21 R 601 may include a C1-C 60 cyclic group containing nitrogen with a deficiency of π electrons.

[0523] In an embodiment, Ar 601 and L 601 in Formula 601 can each independently be a benzene group, a naphthalene group, a fluorene group, a spirobifluorene group, a benzo[9,10]fluorene group, a dibenzo[9,10]fluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, each of which is unsubstituted or substituted with the following, Group, tetracene group, picene group, perylene group, pentacene group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, benzisothiazole group, benzoxazole group, benzisoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, or azacarbazole group: deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1-C 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32 ), or a combination thereof, and

[0524] Q 31 to Q 33 may each independently be a C1-C 10 alkyl group, C1-C 10 alkoxy group, phenyl group, biphenyl group, terphenyl group, or naphthyl group.

[0525] When xe11 in Formula 601 is 2 or greater, two or more Ars 601 may be connected to each other via a single bond.

[0526] In one or more embodiments, Ar in Formula 601 601 may be an anthracene group.

[0527] In one or more embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:

[0528] Formula 601-1

[0529]

[0530] wherein, in Formula 601-1,

[0531] X 614 may be N or C(R 614 ), X 615 may be N or C(R 615 ), X616 may be N or C(R 616 ), and X 614 to X 616 at least one of which may be N,

[0532] L 611 to L 613 each independently is the same as described with respect to L 601 ,

[0533] xe611 to xe613 each independently is the same as described with respect to xe1,

[0534] R 611 to R 613 each independently is the same as described with respect to R 601 , and

[0535] R 614 to R 616 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.

[0536] In one or more embodiments, xe1 and xe611 to xe613 in Formulas 601 and 601-1 may each independently be 0, 1, or 2.

[0537] In one or more embodiments, R 601 and R 611 to R 613 may each independently be phenyl, biphenyl, terphenyl, naphthyl, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, phenanthrene, anthracene, fluoranthene, benzo[9,10]phenanthrene, pyrene, each unsubstituted or substituted with the following, A base, a perylene base, a pentaphene base, a hexacene phenyl group, a pentacene phenyl group, a thiophene group, a furan group, a carbazole group, an indole group, an isoindole group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzosilole group, a pyridine group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a thiadiazole group, an oxadiazole group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, a benzoisothiazole group, a benzoxazole group, a benzoisoxazole group, a triazole group, a tetrazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazone group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, a base, a perylene base, a pentaphene base, a hexacene phenyl group, a pentacene phenyl group, a thiophene group, a furan group, a carbazole group, an indole group, an isoindole group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzosilole group, a pyridine group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a thiadiazole group, an oxadiazole group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, a benzoisothiazole group, a benzoxazole group, a benzoisoxazole group, a triazole group, a tetrazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, or a combination thereof; or

[0538] -S(=O)2(Q 601 ), or -P(=O)(Q 601 )(Q 602 ), and

[0539] Q 601 and Q 602 are the same as those described herein.

[0540] The electron transport region 17 may include one of the compounds ET1 to ET36, or a combination thereof:

[0541]

[0542]

[0543]

[0544] In one or more embodiments, the electron transport region 17 may include 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, DBFPO, or a combination thereof. For example, when the electron transport region 17 includes a hole blocking layer, the hole blocking layer may include DBFPO, BCP, or Bphen:

[0545]

[0546] The thicknesses of the buffer layer, the hole blocking layer, and the electron control layer may each independently be in the range of about to about For example, about to about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, excellent hole blocking characteristics or excellent electron control characteristics can be obtained without a significant increase in the driving voltage.

[0547] The thickness of the electron transport layer may be about to about For example, about to about When the thickness of the electron transport layer is within these ranges, satisfactory electron transport characteristics can be obtained without a significant increase in the driving voltage.

[0548] In addition to the foregoing materials, the electron transport region 17 (e.g., the electron transport layer in the electron transport region 17) may further include a metal-containing material.

[0549] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or a combination thereof. The metal ions of the alkali metal complex may include Li ions, Na ions, K ions, Rb ions, Cs ions, or a combination thereof, and the metal ions of the alkaline earth metal complex may include Be ions, Mg ions, Ca ions, Sr ions, Ba ions, or a combination thereof. The ligands coordinated to the metal ions of the alkali metal complex or the alkaline earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiphenyl oxadiazole, hydroxydiphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or a combination thereof.

[0550] In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, the compound ET-D1(LiQ) or ET-D2:

[0551]

[0552] The electron transport region 17 may include an electron injection layer that facilitates the injection of electrons from the second electrode 19. The electron injection layer may be in direct contact with the second electrode 19.

[0553] The electron injection layer may have i) a single-layer structure composed of a single layer including a single material, ii) a single-layer structure composed of a single layer including a plurality of different materials, or iii) a multi-layer structure composed of a plurality of layers including a plurality of different materials.

[0554] 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.

[0555] The alkali metal may include Li, Na, K, Rb, Cs, or a combination thereof. In an embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs.

[0556] The alkaline earth metal may include Mg, Ca, Sr, Ba, or a combination thereof.

[0557] The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or a combination thereof.

[0558] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may include oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth metal, and the rare earth metal, or a combination thereof.

[0559] The alkali metal compound may include: one of alkali metal oxides such as Li2O, Cs2O, K2O, etc.; one of alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, etc.; or a combination thereof. In an embodiment, the alkali metal compound may include LiF, Li2O, NaF, LiI, NaI, CsI, KI, or a combination thereof.

[0560] The alkaline earth metal compound may include an alkaline earth metal compound such as one of the following: BaO, SrO, CaO, Ba x Sr 1-x O (where 0 < x < 1), or Ba x Ca 1-x O (where 0 < x < 1), or a combination thereof. In an embodiment, the alkaline earth metal compound may include BaO, SrO, CaO, or a combination thereof.

[0561] The rare earth metal compounds may include YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, TbF3, or a combination thereof. In an embodiment, the rare earth metal compounds may include YbF3, ScF3, TbF3, YbI3, ScI3, TbI3, or a combination thereof.

[0562] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include the ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and the ligands coordinated to the metal ions of the alkali metal complex, alkaline earth metal complex, or rare earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiphenyl oxadiazole, hydroxydiphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or a combination thereof.

[0563] The electron injection layer may be composed of the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or a combination thereof as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or a combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.

[0564] The thickness of the electron injection layer may be about to about and for example about to about When the thickness of the electron injection layer is within the range as described above, satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.

[0565] The second electrode 19 is disposed on the intermediate layer 10A as described above. The second electrode 19 may be a cathode as an electron injection electrode, and in this regard, the material for forming the second electrode 19 may be selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function.

[0566] The second electrode 19 may include Li, Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, ITO, IZO, or a combination thereof. The second electrode 19 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0567] The second electrode 19 may have a single-layer structure having a single layer or a multilayer structure including two or more layers.

[0568] As used herein, the term "C1-C 60 alkyl" refers to a straight-chain or branched saturated aliphatic hydrocarbon monovalent group having from 1 to 60 carbon atoms, and as used herein, the term "C1-C 60 alkylene" refers to a divalent group having the same structure as C1-C 60 alkyl.

[0569] As used herein, C1-C 60 alkyl may be C1-C 20 alkyl, such as C1-C 10 alkyl. C1-C 60 alkyl, C1-C 20 alkyl, and / or C1-C 10 alkyl include, as non-limiting examples, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, or tert-decyl, each unsubstituted or substituted with: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, or a combination thereof.

[0570] As used herein, the term "C1-C 60 alkoxy" refers to a monovalent group represented by -OA 101 (where A 101 is C1-C 60 alkyl), and non-limiting examples thereof include methoxy, ethoxy, propoxy, butoxy, and pentyloxy. As used herein, the term "C1-C 60 alkylthio" refers to a monovalent group represented by -OS 101 (where A 101 is C1-C 60 alkyl), and non-limiting examples thereof include methylthio, ethylthio, propylthio, butylthio, and pentylthio.

[0571] As used herein, the term "C2-C 60 alkenyl" refers to a structure containing at least one carbon-carbon double bond at the middle or terminal of C2-C 60 alkyl, and non-limiting examples thereof include vinyl, propenyl, and butenyl. As used herein, the term "C2-C 60"Vinylene" refers to a divalent group having the same structure as C2-C 60 alkenyl.

[0572] As used herein, the term "C2-C 60 alkynyl" refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond at the middle or end of C2-C 60 alkyl, and examples thereof include ethynyl and propynyl. As used herein, the term "C2-C 60 alkynylene" refers to a divalent group having the same structure as C2-C 60 alkynyl.

[0573] As used herein, the term "C3-C 10 cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having from 3 to 10 carbon atoms as ring-forming atoms, and as used herein, the term "C3-C 10 cycloalkylene" refers to a divalent group having the same structure as C3-C 10 cycloalkyl.

[0574] C3-C 10 Examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl.

[0575] As used herein, the term "C1-C 10 heterocycloalkyl" refers to a monovalent saturated cyclic group including at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as ring-forming atoms and 1 to 10 carbon atoms as ring-forming atoms, and as used herein, the term "C1-C 10 heterocycloalkylene" refers to a divalent group having the same structure as C1-C 10 heterocycloalkyl.

[0576] C1-C 10 Examples of heterocycloalkyl include silacyclopentyl, silacyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, and tetrahydrothienyl.

[0577] As used herein, the term "C3-C 10 cycloalkenyl" refers to a monovalent hydrocarbon cyclic group having from 3 to 10 carbon atoms as ring-forming atoms in its ring and at least one carbon-carbon double bond and not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C 10 cycloalkenylene" refers to a divalent group having the same structure as C3-C 10 cycloalkenyl.

[0578] As used herein, the term "C1-C 10 heterocycloalkenyl" refers to a monovalent cyclic group having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, 1 to 10 carbon atoms as ring-forming atoms, and at least one carbon-carbon double bond and being non-aromatic. C1-C 10 Non-limiting examples of heterocycloalkenyl include 2,3-dihydrofuranyl and 2,3-dihydrothienyl. As used herein, the term "C1-C 10 heterocycloalkenylene" refers to a divalent group having the same structure as C1-C 10 heterocycloalkenyl.

[0579] As used herein, the term "C6-C 60 aryl" refers to a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms as ring-forming atoms, and as used herein, the term "C6-C 60 arylene" refers to a divalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms as ring-forming atoms. C6-C 60 Non-limiting examples of aryl include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and yl. When C6-C 60 aryl and C6-C 60 arylene each include two or more rings, the rings may be fused to each other.

[0580] As used herein, the term "C1-C 60 heteroaryl" refers to a monovalent group including a heteroaromatic system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 60 carbon atoms as ring-forming atoms, and as used herein, the term "C1-C 60 heteroarylene" refers to a divalent group including a heteroaromatic system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and 1 to 60 carbon atoms as ring-forming atoms. C1-C 60 Non-limiting examples of heteroaryl include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C 60 heteroaryl and C1-C 60 heteroarylene each include two or more rings, the rings may be fused to each other.

[0581] As used herein, the term "C6-C 60 aryloxy" means -OA 102 (where A 102 is C6-C 60aryl), and as used herein, the term "C6-C 60 arylsulfanyl" means -SA 103 (where A 103 is C6-C 60 aryl).

[0582] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group in which two or more rings are fused to each other, using only carbon as the ring-forming atoms (e.g., the number of carbon atoms can be from 8 to 60), and the entire group is non-aromatic. An example of a monovalent non-aromatic fused polycyclic group is a fluorenyl group. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.

[0583] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" refers to a monovalent group having two or more rings fused to each other, having heteroatoms selected from N, O, P, Si, S, Se, Ge, and B as ring-forming atoms in addition to carbon atoms (e.g., having 1 to 60 carbon atoms), and not being aromatic in its entire structure. Non-limiting examples of monovalent non-aromatic fused heteropolycyclic groups include a carbazolyl group. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.

[0584] As used herein, the term "C1-C 60 cyclic group containing π-deficient nitrogen" refers to a cyclic group having 1 to 60 carbon atoms and including at least one *-N=*' (where * and *' each represent a binding site to an adjacent atom) as a ring-forming moiety. For example, the C1-C 60 cyclic group containing π-deficient nitrogen can be a) a first ring, b) a fused ring in which at least two first rings are fused, or c) a fused ring in which at least one first ring and at least one second ring are fused.

[0585] As used herein, the term "π-rich C3-C 60 cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and not including any *-N=*' (where * and *' each represent a binding site to an adjacent atom) as a ring-forming moiety. For example, the π-rich C3-C 60 cyclic group can be a) a second ring or b) a fused ring in which at least two second rings are fused.

[0586] As used herein, the term "C5-C 60"Carbocyclic group" means a monocyclic or polycyclic group having only 5 to 60 carbon atoms as ring-forming atoms, and can be, for example, a) a third ring or b) a fused ring in which two or more third rings are fused to each other.

[0587] As used herein, the term "C1-C" 60 "Heterocyclic group" means a monocyclic or polycyclic group having 1 to 60 carbon atoms and at least one heteroatom as ring-forming atoms, and can be, for example, a) a fourth ring, b) a fused ring in which two or more fourth rings are fused to each other, or c) a fused ring in which at least one third ring is fused to at least one fourth ring.

[0588] As used herein, the "first ring" can be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, or a thiadiazole group.

[0589] As used herein, the "second ring" can be a benzene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, or a silole group.

[0590] As used herein, the "third ring" can be a cyclopentyl group, a cyclopentadiene group, an indene group, an adamantyl group, a norbornene group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group (norbornanyl group), a bicyclo[2.2.2]octyl group, a cyclohexyl group, a cyclohexene group, or a benzene group.

[0591] As used herein, the "fourth ring" can be a furan group, a thiophene group, a pyrrole group, a silole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, aaza-silole group, diaza-silole group, triaza-silole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0592] For example, C1-C containing nitrogen with electron-deficient π 60The cyclic group can be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, a benzisothiazole group, a benzoxazole group, a benzisoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an acridine group, or a pyridopyrazine group.

[0593] For example, the π - electron - rich C3 - C 60 The cyclic group can be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthene group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, group, a tetracene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, a furan group, a thiophene group, an isoindole group, an indole group, an indene group, a benzofuran group, a benzothiophene group, a benzosilole group, a naphthopyrrole group, a naphthofuran group, a naphthothiophene group, a naphthosilole group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a dibenzosilole group, an indacarbazole group, an indolocarbazole group, a benzofurancarbazole group, a benzothiophenecarbazole group, a benzosilolecarbazole group, a triindolobenzene group, a pyrrolophenanthrene group, a furanophenanthrene group, a thiophenophenanthrene group, a benzonaphthofuran group, a benzonaphthothiophene group, an indolophenanthrene group, a benzofuranophenanthrene group, or a benzothiophenophenanthrene group.

[0594] For example, C5 - C 60 The carbocyclic group can be a cyclopentyl group, a cyclohexyl group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, a 1,2,3,4 - tetrahydronaphthalene group, a cyclopentadiene group, an indene group, a fluorene group, a 5,6,7,8 - tetrahydroisoquinoline group, a 5,6,7,8 - tetrahydroquinoline group, an adamantyl group, a norbornyl group, or a norbornene group.

[0595] For example, C1 - C 60The heterocyclic group may be a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a silole group, a borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole 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 pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, or a benzothiadiazole group.

[0596] As used herein, the term "C1-C containing nitrogen lacking π electrons" 60 cyclic group, π electron-rich C3-C 60 cyclic group, C5-C 60 carbocyclic group, and C1-C 60 heterocyclic group" each refers to a part of a fused ring or a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group depending on the formula structure.

[0597] Substituted C1-C containing nitrogen lacking π electrons 60 cyclic group, substituted π electron-rich C3-C 60 cyclic group, substituted C5-C 60 carbocyclic group, substituted C1-C 60 heterocyclic group, substituted C1-C 60 alkylene, substituted C2-C 60 alkenylene, substituted C2-C60 Arylidyne, substituted C3-C 10 Substituted C1-C 10 Substituted C3-C 10 Substituted C1-C 10 Substituted C6-C 60 Substituted C1-C 60 Substituted divalent non-aromatic fused polycyclic group, substituted divalent non-aromatic fused heteropolycyclic group, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 The substituents of the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may each independently be:

[0598] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio;

[0599] Each C1-C substituted by the following 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 ), or any combination thereof;

[0600] C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 )、or a combination thereof; -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 )、or -P(Q 38 )(Q 39 );or

[0601] a combination thereof.

[0602] Q1 to Q9, Q 11 to Q 19 、Q 21 to Q 29 and Q 31 to Q 39 may each independently be hydrogen; deuterium; -F; or a C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C1-C 60 alkylthio, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, cyano, C1-C 60 alkyl, C6-C 60 aryl, or a combination thereof.

[0603] Unless otherwise defined herein, Q1 to Q9, Q 11 to Q 19 , Q 21 to Q 29 and Q 31 to Q 39 may each independently be, for example:

[0604] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or

[0605] n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl, each unsubstituted or substituted with: deuterium, C1-C 10 alkyl, phenyl, or a combination thereof.

[0606] As used herein, the term "room temperature" refers to a temperature of about 25 °C.

[0607] As used herein, the terms "biphenyl, terphenyl, and quaterphenyl" refer to monovalent groups in which two, three, or four phenyl groups are connected together via single bonds, respectively.

[0608] As used herein, "(C1-C 20 alkyl)phenyl" refers to a phenyl group substituted with at least one C1-C 20 alkyl. Other similar terms can be understood in a similar manner.

[0609] Hereinafter, compounds and organic light-emitting devices according to embodiments are described in detail with reference to synthetic examples and examples. However, the organic light-emitting devices are not limited thereto. The phrase "using 'B' instead of 'A'" used in the description of the synthetic examples refers to the case where the amount of 'A' used is the same as the amount of 'B' used in terms of molar equivalents.

[0610] Examples

[0611] Synthesis Example 1: Synthesis of Compound 35

[0612]

[0613] Under a nitrogen atmosphere in a glove box, 5-(tert-butyl)-N1,N3-bis(3'-chloro-[1,1'-biphenyl]-2-yl)-N1,N3-bis(3-chlorophenyl)benzene-1,3-diamine (1.73 g, 2.28 mmol) and boron triiodide (4.46 g, 11.40 mmol) were added to a 50 mL round-bottom flask, and 1,2-dichlorobenzene (11.4 mL) was added thereto. The resulting mixture was stirred at 160 °C for 4 hours, then cooled to room temperature, and then neutralized with an aqueous solution of sodium acetate (NaOAc). It was worked up with dichloromethane and distilled water. The organic layer was dried over MgSO4, then filtered and concentrated. The concentrated reaction product was purified by silica gel column chromatography (dichloromethane (DCM): hexane = 1:9, v / v) to obtain 7-(tert-butyl)-3,11-dichloro-5,9-bis(3'-chloro-[1,1'-biphenyl]-2-yl)-5,9-dihydro-5,9-diaza-13b-boraphenanthro[3,2,1-de]anthracene (1.01 g), which is a yellow solid. The obtained 7-(tert-butyl)-3,11-dichloro-5,9-bis(3'-chloro-[1,1'-biphenyl]-2-yl)-5,9-dihydro-5,9-diaza-13b-boraphenanthro[3,2,1-de]anthracene was confirmed by ultra-high performance liquid chromatography-mass spectrometry (UPLC-MS). (C 46 H 33 BCl4N2: 764.0734)

[0614] Thereafter, under a nitrogen atmosphere, 7-(tert-butyl)-3,11-dichloro-5,9-bis(3'-chloro-[1,1'-biphenyl]-2-yl)-5,9-dihydro-5,9-diaza-13b-boraphenanthro[3,2,1-de]anthracene (1.6 g, 2.09 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.61 g, 9.19 mmol), Pd2(dba)3 (0.38 g, 0.42 mmol), S-phos (0.34 g, 0.84 mmol) and NaOtBu (1.20 g, 12.5 mmol) were added to a 50 mL round-bottom flask and 35 mL of xylene was added thereto. The resulting mixture was stirred at 130 °C for 6 hours to complete the reaction, filtered through a diatomaceous earth filter, then concentrated, and subsequently purified by silica gel column chromatography (DCM: hexane = 2:8, v / v) to obtain Compound 35 (2.07 g) as a yellow solid. Compound 35 was confirmed by UPLC-MS. (C 94 H 33 D 32 BN6: 1321.5998)

[0615] Evaluation of Example 1

[0616] The Gaussian 09 program was used to calculate the HOMO and LUMO energy levels of compound 35 and R1 to R4 respectively. The Gaussian 09 program involves molecular structure optimization by time-dependent density functional theory (TDDFT) based on B3LYP / 6-31(d,p) / gas. The results are listed in Table 1 below. Additionally, the S1 and T1 energy levels of compound 35 and R1 to R4 respectively were calculated based on the method described in J. Phys. Chem. A 2021, 125, 10373 - 10378 using delta SCF reference. ΔEst was obtained by subtracting the T1 energy level from the S1 energy level. The results are shown in Table 1 below.

[0617] Table 1

[0618]

[0619] <r1>

[0620]

[0621] <r2>

[0622]

[0623] <r3>

[0624]

[0625] Example 1

[0626] On which is formed A glass substrate with a thick ITO electrode (anode) is cut into a size of 50 mm × 50 mm × 0.5 mm, and ultrasonically cleaned in acetone, isopropyl alcohol, and pure water for 15 minutes each, followed by ultraviolet (UV) ozone cleaning for 30 minutes. Then, the obtained glass substrate is loaded onto a vacuum deposition device.

[0627] Next, HAT-CN is deposited on the ITO electrode on the glass substrate to form a hole injection layer with a thickness of And NPB is deposited on the hole injection layer to form a first hole transport layer with a thickness of And TCTA is deposited on the first hole transport layer to form a second hole transport layer with a thickness of And mCP is deposited on the second hole transport layer to form an electron blocking layer with a thickness of

[0628] The first host (H1), the second host (H2), the sensitizer (S-1), and the emitter (Compound 35) are co-deposited on the electron blocking layer to form an emission layer with a thickness of At this point, the first host and the second host are mixed at a ratio of 60:40, and based on the total weight of the first host, the second host, the sensitizer, and the emitter, the sensitizer and the emitter are adjusted to 15 wt% and 1 wt%, respectively.

[0629] DBFPO is deposited on the emission layer to form a hole blocking layer with a thickness of Then, DBFPO and Liq are co-deposited on the hole blocking layer at a weight ratio of 5:5 to form an electron transport layer with a thickness of Then, Liq is deposited on the electron transport layer to form an electron injection layer with a thickness of Then, Al is deposited on the electron injection layer to form a cathode with a thickness of , thus completing the fabrication of the light-emitting device.

[0630]

[0631] Comparative Examples 1 to 3

[0632] A light-emitting device is fabricated in the same manner as in Example 1, except that: when forming the emission layer, the compounds shown in Table 2 are each used instead of Compound 35 as the emitter. ​

[0633] Evaluation of Example 2

[0634] For each of the light-emitting devices fabricated in Example 1 and Comparative Examples 1 to 3, the emission peak wavelength (maximum emission peak wavelength), full width at half maximum (FWHM), external quantum efficiency at 1000 nits (EQE at 1000 nits), and lifetime (LT at 1000 nits 95 ) of the electroluminescence (EL) spectrum were evaluated. The results are shown in Table 2. The emission peak wavelength and FWHM of the EL spectrum were evaluated for each of the light-emitting devices using the EL spectrum (at 1000 cd / m 2 ) measured using a luminance meter (Minolta Cs-1000A). The external quantum efficiency at 1000 nits was evaluated using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A), and expressed as a relative value (%) with respect to Comparative Example 1. For the lifetime (LT at 1000 nits 95 ), the time (hr) taken to reach 95% of the luminance compared to 100% of the initial luminance was evaluated, and this value was expressed as a relative value (%) with respect to Comparative Example 1.

[0635] Table 2

[0636]

[0637]

[0638] <r1>

[0639]

[0640] <r2>

[0641]

[0642] <r3>

[0643]

[0644] As can be seen from Table 2, compared with the light-emitting devices of Comparative Examples 1 to 3, the light-emitting device of Example 1 has a lower FWHM and exhibits a higher external quantum efficiency and device lifetime.

[0645] For the polycyclic compound, the introduction of a substituent containing a heteroatom contributes to the stabilization of the light-emitting process, and thus, a relatively small light-emitting FWHM can be obtained, and a relatively low HOMO level can be maintained, thereby allowing the emission of blue light with a reduced wavelength. Moreover, an electronic device such as a light-emitting device using the polycyclic compound can have an improved external quantum efficiency and improved lifetime characteristics.

[0646] It should be understood that the embodiments described herein should be considered only in a descriptive sense and not for purposes of limitation. The description of features or aspects in each embodiment should typically be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, those of ordinary skill in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope as defined by the appended claims. < / r2> < / r1> < / r2> < / r1>

Claims

1. A polycyclic compound represented by Formula 1: Formula 1 wherein Ar0 in Formula 1 is a group represented by Formula 2, Formula 2 Among them, in Formulas 1 and 2, Ring CY1 to ring CY3 are each independently a C5-C 60 carbocyclic group or a C3-C 60 heterocyclic group, W1 is a single bond, O, S, N(R8), N(Ar1), C(R8)(R9), or Si(R8)(R9), W2 is a single bond, O, S, N(R 10 ), N(Ar2), C(R 10 )(R 11 ), or Si(R 10 )(R 11 ), n1 and n2 are each independently 0 or 1, When n1 is 0, *-(W1) n1 -*' does not exist, When n2 is 0, *-(W2) n2 -*' does not exist the sum of n1 and n2 is 1 or 2, T1 is a single bond, C(R 12 )(R 13 )、Si(R 12 )(R 13 )、N(R 12 )、B(R 12 ), O, S, Se, or Te, Ar1 and Ar2 are each independently a group represented by Formula 2, R1 to R 13 each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a substituted or unsubstituted C1-C 60 alkyl, a substituted or unsubstituted C2-C 60 alkenyl, a substituted or unsubstituted C2-C 60 alkynyl, a substituted or unsubstituted C1-C 60 alkoxy, a substituted or unsubstituted C1-C 60 alkylthio, a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C1-C 10 heterocycloalkyl, a substituted or unsubstituted C3-C 10 cycloalkenyl, a substituted or unsubstituted C1-C 10 heterocycloalkenyl, a substituted or unsubstituted C6-C 60 aryl, a substituted or unsubstituted C6-C 60 aryloxy, a substituted or unsubstituted C6-C 60 arylthio, a substituted or unsubstituted C1-C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), a1 to a3 and m are each independently an integer from 0 to 10, a4 to a6 are each independently an integer from 0 to 4, a7 is an integer from 0 to 8, R1 to R3 and R8 to R 11 Two or more of which are optionally joined to each other to form a substituted or unsubstituted C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group, Substituted C5-C 30 carbocyclic group, substituted C1-C 30 heterocyclic group, substituted C1-C 60 alkyl group, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 alkoxy group, substituted C1-C 60 alkylthio group, substituted C3-C 10 cycloalkyl group, substituted C1-C 10 heterocycloalkyl group, substituted C3-C 10 cycloalkenyl group, substituted C1-C 10 heterocycloalkenyl group, substituted C6-C 60 aryl group, substituted C6-C 60 aryloxy group, substituted C6-C 60 arylthio group, substituted C1-C 60 heteroaryl group, at least one substituent of the substituted monovalent non-aromatic fused polycyclic group and the substituted monovalent non-aromatic fused heteropolycyclic group is: Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, or C1-C 60 alkylthio group; each of C1-C substituted as follows 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, or C1-C 60 alkylthio: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 )、or a combination thereof; Each of which is unsubstituted or substituted with the following: C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C1-C 60 alkylthio, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 23 )、-Si(Q 23 )(Q 24 )(Q 25 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 )、or a combination thereof; -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 )、 or -P(Q 38 )(Q 39 ); or their combinations, and Q1 to Q9, Q 11 to Q 19 、Q 21 to Q 29 and Q 31 to Q 39 are each independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; amino; amidino; hydrazino; hydrazono; a carboxylic acid group or its salt; a sulfonic acid group or its salt; a phosphoric acid group or its salt; or a C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C1-C 60 alkylthio, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, C1-C 60 alkyl, C6-C 60 aryl, or a combination thereof.

2. The polycyclic compound according to claim 1, wherein Ring CY1 to Ring CY3 are each independently a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group.

3. The polycyclic compound according to claim 1, wherein i) n1 is 1 and n2 is 0, or ii) n1 is 0 and n2 is 1.

4. The polycyclic compound according to claim 1, wherein the sum of n1 and n2 is 1, W1 is N(R8) or N(Ar1), and W2 is N(R 10 ) or N(Ar2).

5. The polycyclic compound according to claim 1, wherein the polycyclic compound has a symmetric structure.

6. The polycyclic compound according to claim 1, wherein T1 is a single bond, O, or S.

7. The polycyclic compound according to claim 1, wherein R1 to R3 are each independently selected from: hydrogen, deuterium, -F, or cyano; A C1-C alkyl which is unsubstituted or substituted with deuterium, -F, a cyano group, or a combination thereof; or 20 or A phenyl or carbazolyl group, each of which is unsubstituted or substituted by: deuterium, -F, cyano, C1-C 20 alkyl, phenyl, or a combination thereof, R4 to R7 are each: hydrogen, deuterium, -F, or cyano; A C1-C alkyl that is unsubstituted or substituted with deuterium, -F, cyano, or a combination thereof; or 20 or A phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or azacarbazolyl group, each unsubstituted or substituted with: deuterium, -F, cyano, C1-C 20 alkyl, phenyl, or a combination thereof, and / or R8 to R 13 Each independently is: hydrogen, deuterium, -F, or cyano; Each of which is unsubstituted or substituted by the following C1-C 20 alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, or dibenzosilolyl: deuterium, -F, cyano, C1-C 20 alkyl, phenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, dibenzosilolyl, or a combination thereof; or -N(Q1)(Q2), and Q1 and Q2 are each independently a C1-C that is unsubstituted or substituted as follows 20 alkyl group, phenyl group, biphenyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, fluorene group, or dibenzosilolyl group: deuterium, -F, cyano group, C1-C 20 alkyl group, phenyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, fluorene group, dibenzosilolyl group, or a combination thereof.

8. The polycyclic compound according to claim 1, wherein the polycyclic compound is represented by Formula 1A: Formula 1A Among them, in Formula 1A, W3 is O, S, N(R 10 ), N(Ar2), C(R 10 )(R 11 ), or Si(R 10 )(R 11 ), Ar0, Ar2, R1 to R3, R 10 and R 11 each as described in claim 1, b1 and b2 are each independently an integer from 0 to 4, and b3 is an integer from 0 to 3.

9. The polycyclic compound according to claim 1, wherein the group represented by Formula 2 is any one of the groups represented by Formulas 2-1 to 2-9: Among them, In Formulas 2-1 to 2-9, T1, R4 to R7, and a4 to a7 are each as described in claim 1.

10. The polycyclic compound according to claim 1, wherein the polycyclic compound includes at least one deuterium, tert-butyl, or a combination thereof.

11. The polycyclic compound according to claim 1, wherein the polycyclic compound is one of Compounds 1 to 66:

12. A light-emitting device, comprising: a first electrode; a second electrode, and an intermediate layer disposed between the first electrode and the second electrode and including an emission layer, wherein the intermediate layer includes one or more polycyclic compounds represented by Formula 1 according to any one of claims 1 to 11.

13. The light-emitting device according to claim 12, wherein the one or more polycyclic compounds are included in the emission layer.

14. The light-emitting device according to claim 12, wherein the emission peak wavelength of the light emitted from the emission layer is 440 nm to 470 nm.

15. The light-emitting device according to claim 13, wherein The one or more polycyclic compounds included in the emission layer are emitters or sensitizers.

16. The light-emitting device according to claim 13, wherein the emission layer further includes a sensitizer, and the sensitizer and the one or more polycyclic compounds are different from each other.

17. An electronic device, comprising the light-emitting device according to any one of claims 12 to 16.

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