Heterocyclic compound, and organic light-emitting device and electronic apparatus including same

Abstract

Disclosed are a heterocyclic compound, and an organic light-emitting device and an electronic device including the same, the heterocyclic compound being represented by Formula 1, wherein Ar1 and optionally included Ar2 in X1 are each independently a group represented by Formula 2, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group; rings CY1 to CY7 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group; cz1 is a group represented by formula 3; and the description of the remaining groups and variables is as provided herein. Formula 1 # imgabs 0 #, formula 2 # imgabs 1 # and formula 3 # imgabs 2 #

Description

[0001] Cross - reference to related applications

[0002] This application claims the priority and benefits of Korean Patent Application Nos. 10 - 2024 - 0000967 filed on January 3, 2024 and 10 - 2024 - 0151489 filed on October 30, 2024 with the Korean Intellectual Property Office, and all benefits arising therefrom, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present subject matter relates to heterocyclic compounds, and organic light - emitting devices and electronic devices including the same. Background Art

[0004] An organic light - emitting device (OLED) is a self - emissive device having excellent characteristics in terms of viewing angle, response time, brightness, driving voltage, response speed, etc. The OLED can also generate full - color images.

[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 disposed between the anode and the emission layer, and an electron - transport region may be disposed between the emission layer and the cathode. Holes provided from the anode move toward the emission layer through the hole - transport region, and electrons provided from the cathode move toward the emission layer through the electron - transport region. The holes and electrons recombine in the emission layer to generate excitons. The excitons may transition from an excited state to a ground state, thereby generating light. Summary of the Invention

[0006] Provided are heterocyclic compounds, and organic light - emitting devices and electronic devices including the same.

[0007] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments of the disclosure.

[0008] According to one aspect, provided is a heterocyclic compound represented by Formula 1:

[0009] Formula 1

[0010]

[0011] Formula 2

[0012]

[0013] Formula 3

[0014]

[0015] wherein, in Formulas 1, 2, and 3,

[0016] X1 is a single bond, O, S, Se, N(Ar2), N(R1), C(R1)(R2), Si(R1)(R2), Ge(R1)(R2), B(R1), P(R1), P(═O)(R1), S(═O)2, or C(═O), and

[0017] Ar1 and Ar2 are each independently a group represented by Formula 2, a substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 an alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

[0018] Rings CY1 to CY7 are each independently C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups,

[0019] Cz1 is a group represented by Formula 3,

[0020] R 11 is substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C1-C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

[0021] R1, R2, R 10 , R 20 , R 30 , R 40 , and R 50 Each is independently a group represented by Formula 3, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amidine group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-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 10Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkylaryl, 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 Alkylheteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 Heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2),

[0022] R 60 and R 70 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 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 C7-C 60 alkylaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 heteroarylthio, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(═O)(Q1), -S(═O)(Q1), -S(═O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(═O)(Q1)(Q2), or -P(═S)(Q1)(Q2),

[0023] b10, b20, b30, b40, and b50 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14,

[0024] b60 and b70 may each independently be 1, 2, 3, 4, 5, 6, 7, or 8,

[0025] R1, R2, R 10 , R 11 , R 20 , R 30 , R 40 , R 50 , R 60 , and R 70 At least two adjacent groups in are optionally bonded (combined) together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups,

[0026] Substituted C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, 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 C7-C60 Alkylaryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C2-C 60 Alkylheteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 The substituents of arylthio, substituted monovalent non-aromatic fused polycyclic groups, and substituted monovalent non-aromatic fused heteropolycyclic groups are each independently:

[0027] Deuterium, -F, -Cl, -Br, -I, -SF5, -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;

[0028] C1-C each substituted with 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, -SF5, -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, C7-C 60 Alkylaryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkylheteroaryl, C1-C 60 Heteroaryloxy, C1-C 60Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 11 )(Q 12 )(Q 13 )、-Ge(Q 11 )(Q 12 )、-C(=O)(Q 13 )、-S(=O)(Q 11 )、-S(=O)2(Q 11 )、-B(Q 11 )(Q 11 )、-P(Q 12 )(Q 11 )、-P(=O)(Q 12 )(Q 11 )、-P(=S)(Q 12 )(Q 11 )、or a combination thereof;

[0029] Each of C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group, which is unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, -SF5, -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 or a combination thereof; 60Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkylaryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkylheteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 21 )(Q 22 )(Q 23 ), -Ge(Q 21 )(Q 22 )(Q 23 ), -C(=O)(Q 21 ), -S(=O)(Q 21 ), -S(=O)2(Q 21 ), -B(Q 21 )(Q 22 ), -P(Q 21 )(Q 22 ), -P(=O)(Q 21 )(Q 22 ), -P(=S)(Q 21 )(Q 22 ), or a combination thereof;

[0030] -N(Q 31 )(Q 32 ), -Si(Q 31 )(Q 32 )(Q 33 ), -Ge(Q 31 )(Q 32 )(Q 33 ), -C(=O)(Q 31 ), -S(=O)(Q 31 ), -S(=O)2(Q 31 ), -B(Q 31 )(Q 32 ), -P(Q 31 )(Q 32 ), -P(=O)(Q 31 )(Q 32 ), or -P(=S)(Q 31 )(Q 32 ); or

[0031] their combination,

[0032] Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, 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, 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 C7-C 60 alkylaryl, a substituted or unsubstituted C7-C 60 arylalkyl, 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 C2-C 60 alkylheteroaryl, a substituted or unsubstituted C2-C 60 heteroarylalkyl, a substituted or unsubstituted C1-C 60 heteroaryloxy, a substituted or unsubstituted C1-C 60 heteroarylthio, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and

[0033] * represents the binding site to an adjacent atom.

[0034] According to another aspect, the organic light-emitting device includes at least one heterocyclic compound represented by Formula 1.

[0035] According to another aspect, there is provided an organic light-emitting device including a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes at least one heterocyclic compound represented by Formula 1.

[0036] According to another aspect of the present disclosure, an electronic device includes at least one heterocyclic compound represented by Formula 1.

[0037] According to another aspect, there is provided an electronic device including the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] The above and other aspects, features, and advantages of some embodiments will become more apparent from the following detailed description when considered in conjunction with the accompanying drawings, in which:

[0039] Figure 1 is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments; and

[0040] Figures 2 to 6 are each a schematic diagram showing energy transfer of an organic light-emitting device according to one or more embodiments. DETAILED DESCRIPTION

[0041] Embodiments will now be described in further detail, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout the specification. In this regard, the present embodiments may have different forms and should not be construed as limited to the descriptions set forth herein. Accordingly, the embodiments are described only by way of example with reference to the accompanying drawings to explain aspects. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. Expressions such as "at least one (kind) of" when before or after a list of elements modify the entire list of elements and not individual elements of the list.

[0042] The terms used herein are for the purpose of describing one or more exemplary embodiments only and are not intended to be limiting. As used herein, the singular forms "a," "an," and "the" are also intended to include the plural forms unless the context clearly dictates otherwise. The term "or" means "and / or." It will be further understood that the terms "comprises" or "comprising," when used in this specification, specify 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 groups thereof.

[0043] It will be understood that although the terms first, second, third, etc. may be used herein to describe various elements, components, regions, layers and / or sections, these elements, components, regions, layers and / or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or section from another. Thus, a first element, component, region, layer or section discussed below may be termed a second element, component, region, layer or section without departing from the teachings of this embodiment.

[0044] Exemplary embodiments are described herein with reference to cross-sectional views that are schematic illustrations of idealized embodiments. As such, 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 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 a region and are not intended to limit the scope of the claims.

[0045] It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, no intervening elements are present.

[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 general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the present disclosure and the relevant art and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0047] As used herein, “about” or “approximately” includes the stated value and means within an acceptable deviation range for a particular 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 particular 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 ±5%.

[0048] As used herein, "energy level" (e.g., singlet (S1) energy level or triplet (T1) energy level) is expressed as an absolute value from the vacuum energy level. Additionally, when an energy level is referred to as "deep", "high", or "large", the energy level has a large absolute value based on the vacuum energy level of "0 electron volts (eV)", and when an energy level is referred to as "shallow", "low", or "small", the energy level has a small absolute value based on the vacuum energy level of "0 eV".

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

[0050] Formula 1

[0051]

[0052] Wherein, in Formula 1, X1 is a single bond, O, S, Se, N(Ar2), N(R1), C(R1)(R2), Si(R1)(R2), Ge(R1)(R2), B(R1), P(R1), P(=O)(R1), S(=O)2, or C(=O).

[0053] In one or more embodiments, X1 can be a single bond, O, S, Se, N(Ar2), N(R1), C(R1)(R2), or Si(R1)(R2).

[0054] In Formula 1, Ar1 and Ar2 are each independently a group represented by Formula 2, a substituted or unsubstituted C6-C 60 aryl, a substituted or unsubstituted C1-C 60 heteroaryl, a substituted or unsubstituted C2-C 60 alkyl heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group:

[0055] Formula 2

[0056]

[0057] Wherein, in Formulas 1 and 2, ring CY1 to ring CY5 can each independently be a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group.

[0058] In Formula 2, * represents the bonding site to an adjacent atom.

[0059] In Formula 1, Cz1 is a group represented by Formula 3:

[0060] Formula 3

[0061]

[0062] In Formula 3, ring CY6 and ring CY7 are each independently a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group.

[0063] Thus, in Formula 1, rings CY1 to CY7 are each independently a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group.

[0064] In one or more embodiments, rings CY1 to CY7 can each independently be i) a first ring, ii) a second ring, iii) a fused ring group in which two or more first rings are fused to each other, iv) a fused ring group in which two or more second rings are fused to each other, or v) a fused ring group in which one or more first rings are fused to one or more second rings,

[0065] wherein the first ring can be a cyclopentyl group, a cyclopentadienyl group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole 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 azasilole group, a diazasilole group, or a triazasilole group, and

[0066] the second ring can be 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 (i.e., a norcamphyl group), a bicyclo[2.2.2]octyl group, a cyclohexyl group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0067] In one or more embodiments, rings CY1 to CY7 can each independently be a C6-C 30 aromatic carbocyclic group or a C1-C 30 aromatic heterocyclic group.

[0068] In one or more embodiments, rings CY1 to CY7 can each independently be 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, benzothiophene group, benzofuran group, indole group, indene group, benzothiophene group, benzoborole group, benzophosphole group, benzoselenophene group, benzogermole group, dibenzothiophene group, dibenzofuran group, carbazole group, fluorene group, dibenzosilole group, dibenzoborole group, dibenzophosphole group, dibenzoselenophene group, dibenzogermole group, dibenzothiophene 5 - oxide group, 9H - fluoren - 9 - one group, dibenzothiophene 5,5 - dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilole group, azabenzoborole group, azabenzophosphole group, azabenzoselenophene group, azabenzogermole group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzoselenophene group, azadibenzogermole group, azadibenzothiophene 5 - oxide group, aza - 9H - fluoren - 9 - one group, azadibenzothiophene 5,5 - dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, 5,6,7,8 - tetrahydroisoquinoline group, 5,6,7,8 - tetrahydroquinoline group, adamantyl group, norbornyl group, or norbornene group.

[0069] In one or more embodiments, ring CY1 to ring CY5 may each independently be a benzene group, naphthalene group, phenanthrene group, fluorene group, pyridine group, pyrimidine group, triazine group, quinoline group, isoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilole group, dibenzoborole group, dibenzophosphole group, dibenzoselenophene group, dibenzogermole group, dibenzothiophene 5 - oxide group, 9H - fluoren - 9 - one group, or dibenzothiophene 5,5 - dioxide group.

[0070] In one or more embodiments, ring CY6 and ring CY7 may each independently be a benzene group, naphthalene group, phenanthrene group, pyridine group, pyrimidine group, quinoline group, isoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, or quinazoline group.

[0071] In one or more embodiments, the group represented by Formula 2 may be a group represented by one of Formula 2 - 1 to 2 - 3:

[0072] Formula 2 - 1

[0073]

[0074] Formula 2-2

[0075]

[0076] Formula 2-3

[0077]

[0078] wherein, in Formulas 2-1 to 2-3,

[0079] Ring CY4, Ring CY5, R 40 , R 50 , b40 and b50 are each the same as those described herein,

[0080] represents a single bond or a double bond, and

[0081] * represents the binding site to an adjacent atom.

[0082] In one or more embodiments, the group represented by Formula 2 can be a group represented by one of Formulas 2A to 2C:

[0083] Formula 2A

[0084]

[0085] Formula 2B

[0086]

[0087] Formula 2C

[0088]

[0089] wherein, in Formulas 2A to 2C,

[0090] X 41 can be C(R 41 ) or N, X 42 can be C(R 42 ) or N, X 43 can be C(R 43 ) or N, and X 44 can be C(R 44 ) or N,

[0091] X 51 can be C(R 51 ) or N, X 52 can be C(R 52 ) or N, X 53 can be C(R 53 ) or N, X 54 can be C(R54 ) or N, and X 55 may be C(R 55 ) or N,

[0092] R 41 to R 44 are each independently the same as described in this specification,

[0093] R 51 to R 55 are each independently the same as described in this specification, and

[0094] * represents the binding site to the adjacent atom.

[0095] For example, in Formulas 2A to 2C, one of R 51 to R 55 , preferably R 52 or R 54 , may be phenyl, biphenyl, or naphthyl.

[0096] In one or more embodiments, the group represented by Formula 3 may be the group represented by Formula 3A:

[0097] Formula 3A

[0098]

[0099] wherein, in Formula 3A,

[0100] X 61 may be C(R 61 ) or N, X 62 may be C(R 62 ) or N, X 63 may be C(R 63 ) or N, and X 64 may be C(R 64 ) or N,

[0101] X 71 may be C(R 71 ) or N, X 72 may be C(R 72 ) or N, X 73 may be C(R 73 ) or N, and X 74 may be C(R 74 ) or N,

[0102] R 61 to R 64 are each independently the same as described regarding R 60 ,

[0103] R 71 to R 74Each independently with respect to R 70 is the same as that described for

[0104] * represents a binding site to an adjacent atom.

[0105] In Formula 1, R 11 is a substituted or unsubstituted C1-C 60 alkyl, a substituted or unsubstituted C3-C 10 cycloalkyl, 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.

[0106] In Formulas 1 and 2, R1, R2, R 10 , R 20 , R 30 , R 40 and R 50 each independently is a group represented by Formula 3, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro 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 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 C7-C 60 alkylaryl, a substituted or unsubstituted C7-C 60 arylalkyl, 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 C2-C 60 alkylheteroaryl, a substituted or unsubstituted C2-C 60 heteroarylalkyl, a substituted or unsubstituted C1-C 60 heteroaryloxy, a substituted or unsubstituted C1-C 60a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0107] In Formula 3, R 60 and R 70 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro 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 substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C1-C 60 alkylthio group, 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 C7-C 60 alkylaryl group, a substituted or unsubstituted C7-C 60 arylalkyl 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 C2-C 60 alkylheteroaryl group, a substituted or unsubstituted C2-C 60 heteroarylalkyl group, a substituted or unsubstituted C1-C 60 heteroaryloxy group, a substituted or unsubstituted C1-C 60Heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0108] In one or more embodiments, R1, R2, R 10 , R 20 , R 30 , R 40 , R 50 , R 60 and R 70 may each independently be:

[0109] C1-C 20 alkyl;

[0110] C1-C 20 alkyl substituted with: deuterium, -F, -Cl, -Br, -I, -SF5, -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, deuterated C1-C 20 alkyl, fluorinated C1-C 20 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornanyl), 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)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(C1-C alkyl) bicyclo[2.2.1]heptyl, (C1-C 20 (C1-C alkyl) bicyclo[2.2.2]octyl, silacyclopentyl, phenyl, (C1-C 20 (C1-C alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidinyl, or a combination thereof; or

[0111] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, silacyclopentyl, phenyl, (C1-C 20 (C1-C alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, (C1-C alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothienyl: deuterium, -F, -Cl, -Br, -I, -SF5, -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, deuterated C1-C 20 alkyl, fluorinated C1-C 20 alkyl, C1-C 20 alkoxy, C1-C 20 alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, (C1-C 20 (C1-C alkyl)cyclopentyl, (C1-C 20 (C1-C alkyl)cyclohexyl, (C1-C 20 (C1-C alkyl)cycloheptyl, (C1-C 20 (C1-C alkyl)cyclooctyl, (C1-C 20(C1-C alkyl)adamantyl, (C1-C 20 (C1-C alkyl)norbornenyl, (C1-C 20 (C1-C alkyl)cyclopentenyl, (C1-C 20 (C1-C alkyl)cyclohexenyl, (C1-C 20 (C1-C alkyl)cycloheptenyl, (C1-C 20 (C1-C alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 (C1-C alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 (C1-C alkyl)bicyclo[2.2.1]heptyl, (C1-C 20 (C1-C alkyl)bicyclo[2.2.2]octyl, silacyclopentyl, phenyl, (C1-C 20 (C1-C alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, (C1-C alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, 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, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, or a combination thereof.

[0112] In one or more embodiments, R1, R2, R 10 , R 20 , R 30 , R 40 , R 50 , R 60 and R 70 may each independently be:

[0113] hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, 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 20 alkyl, C1-C 20 alkoxy, or C1-C 20 alkylthio;

[0114] C1-C 20 alkyl, C1-C 20 alkoxy, or C1-C 20Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, -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, deuterated C1-C 20 alkyl, fluorinated C1-C 20 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornanyl), 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)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[2.2.1]heptyl, (C1-C 20 alkyl)bicyclo[2.2.2]octyl, silacyclopentyl, phenyl, (C1-C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidinyl, or a combination thereof;

[0115] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, silacyclopentyl, phenyl, (C1-C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, a base, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuryl, or azadibenzothienyl: deuterium, -F, -Cl, -Br, -I, -SF5, -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 20 alkyl, deuterated C1-C 20 alkyl, fluorinated C1-C 20 alkyl, C1-C 20 alkoxy, C1-C 20 alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, 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)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[2.2.1]heptyl, (C1-C 20 alkyl)bicyclo[2.2.2]octyl, silacyclopentyl, phenyl, (C1-C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, a group selected from the group consisting of a phenyl group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuryl group, a benzothienyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuryl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuryl group, an azadibenzothienyl group, or a combination thereof; or

[0116] -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0117] In one or more embodiments, R 11 may be a group represented by one of Formulae 9-1 to 9-61, 9-201 to 9-244, 10-1 to 10-154, or 10-201 to 10-350.

[0118] In one or more embodiments, R1, R2, R 10 , R 20 , R 30 , R 40 , R 50 , R 60 and R 70 may each independently be:

[0119] hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, or C1-C 60 alkylthio; or

[0120] a group represented by one of Formulae 9-1 to 9-61, 9-201 to 9-244, 10-1 to 10-154, or 10-201 to 10-350:

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131] Among formulas 9-1 to 9-61, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350, * represents a binding site to an adjacent atom, "Ph" represents a phenyl group, "TMS" represents a trimethylsilyl group, and "TMG" represents a trimethylgermyl group.

[0132] In one or more embodiments, R1, R2, R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , and R 70 may each independently be:

[0133] a group represented by formula 3, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, or C1-C 60 alkylthio; or

[0134] a group represented by one of formulas 9-1 to 9-61, 9-201 to 9-244, 10-1 to 10-154, or 10-201 to 10-350.

[0135] In one or more embodiments, at least one of R 10 , R 20 , and R 30 may be a group represented by formula 3.

[0136] For example, at least one of R with a quantity of b10 10 , at least one of R with a quantity of b20 20 , and / or at least one of R with a quantity of b30 30 may be a group represented by Formula 3.

[0137] In one or more embodiments, at least one of R with a quantity of b10 10 may be a group represented by Formula 3.

[0138] In one or more embodiments, at least one of R with a quantity of b20 20 may be a group represented by Formula 3.

[0139] In one or more embodiments, at least one of R with a quantity of b30 30 may be a group represented by Formula 3.

[0140] R 11 is a substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C 60 aryl, 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.

[0141] In one or more embodiments, R 11 may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 alkylphenyl, or naphthyl.

[0142] In one or more embodiments, at least one of R with a quantity of b20 20 may be a group represented by Formula 3.

[0143] In Formulas 1 and 2, b10, b20, b30, b40, and b50 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14.

[0144] In Formula 3, b60 and b70 are each independently 1, 2, 3, 4, 5, 6, 7, or 8.

[0145] In Formulas 1 and 2, R1, R2, R 10 , R 11 , R20 , R 30 , R 40 , R 50 , R 60 and R 70 at least two adjacent groups in 30 and 30 optionally bond together to form a substituted or unsubstituted C5-C

[0146] In one or more embodiments, the heterocyclic compound may be represented by Formula 11 or 12:

[0147] Formula 11

[0148]

[0149] Formula 12

[0150]

[0151] wherein, in Formulas 11 and 12,

[0152] ring CY1 to ring CY3, X1, Ar1, Ar2, X1, Cz1, R 10 , R 11 , R 20 , R 30 , b10, b20, and b30 are each the same as described herein,

[0153] Cz2 is the same as that described for Cz1,

[0154] R 21 is the same as that described for R 20 , and

[0155] represents a single bond or a double bond.

[0156] In one or more embodiments, the heterocyclic compound may be represented by Formula 21 or 22:

[0157] Formula 21

[0158]

[0159] Formula 22

[0160]

[0161] wherein, in Formulas 21 and 22,

[0162] Ar1, Ar2, X1 and R 11 are each the same as described herein,

[0163] X 12 may be C(R 12 ), or N, and X 13 may be C(R 13 ), or N,

[0164] X 21 may be C(R 21 ), or N, X 22 may be C(R 22 ), or N, X 23 may be C(R 23 ), or N, and X 24 may be C(R 24 ), or N,

[0165] X 31 may be C(R 31 ), or N, X 32 may be C(R 32 ), or N, and X 33 may be C(R 33 ), or N,

[0166] X 61 may be C(R 61 ), or N, X 62 may be C(R 62 ), or N, X 63 may be C(R 63 ), or N, X 64 may be C(R 64 ), or N, X 65 may be C(R 65 ), or N, X 66 may be C(R 66 ), or N, X 67 may be C(R 67 ), or N, and X 68 may be C(R 68 ), or N,

[0167] X 71 may be C(R 71 ), or N, X 72 may be C(R 72 ), or N, X 73 may be C(R 73 ), or N, X 74 may be C(R 74 ), or N, X 75 may be C(R 75 ), or N, X 76 may be C(R 76 ), or N, X 77 may be C(R 77 ), or N, and X 78can be C(R 78 ) or N

[0168] R 12 and R 13 are each independently the same as described for R 10 .

[0169] R 21 to R 24 are each independently the same as described for R 20 .

[0170] R 31 to R 33 are each independently the same as described for R 30 .

[0171] R 61 to R 68 are each independently the same as described for R 60 , and

[0172] R 71 to R 78 are each independently the same as described for R 70 .

[0173] In one or more embodiments, the heterocyclic compound can be represented by Formula 31 or 32:

[0174] Formula 31

[0175]

[0176] Formula 32

[0177]

[0178] wherein, in Formulas 31 and 32, Ar1, Ar2, X1, and R 11 are each the same as described herein, R 12 and R 13 are each independently the same as described for R 10 , R 21 to R 24 are each independently the same as described for R 20 ,

[0179] R 31 to R 33 are each independently the same as described for R 30 ,

[0180] R 61 to R 68 are each independently the same as described for R 60 , and

[0181] R 71 to R 78 are each independently the same as those described with respect to R 70 as described.

[0182] For example, in Formulas 31 and 32, Ar1 and Ar2 can each independently be a group represented by one of Formulas 2A to 2C, and in Formulas 2A to 2C, R 51 to R 55 one of, preferably R 52 or R 54 , can be phenyl, biphenyl, or naphthyl. In Formulas 31 and 32, R 11 can be an unsubstituted or substituted C1-C 20 alkyl (e.g., C1-C 10 alkyl or C1-C5 alkyl): deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 alkyl, C1-C 20 alkoxy, or C1-C 20 alkylthio. In Formulas 31 and 32, R 21 can be the same as or different from R 11 . In Formulas 31 and 32, R 32 can be an unsubstituted or substituted C1-C 20 alkyl (e.g., C1-C 20 linear alkyl or C3-C 20 branched alkyl, such as C1-C 10 linear alkyl or C3-C 10 branched alkyl): deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 alkyl, C1-C 20 alkoxy, or C1-C 20 alkylthio.

[0183] In one or more embodiments, the heterocyclic compound represented by Formula 1 can have a symmetric structure or an asymmetric structure.

[0184] For example, the heterocyclic compound represented by Formula 1 can have a symmetric structure.

[0185] In one or more embodiments, the heterocyclic compound represented by Formula 1 can have an asymmetric structure.

[0186] As used herein, a substituted C5-C 30 carbocyclic group, a substituted C1-C 30Heterocyclic 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 C7-C 60 Alkylaryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C2-C 60 Alkylheteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 Heteroarylthio, substituted monovalent non-aromatic fused polycyclic group, and substituted monovalent non-aromatic fused heteropolycyclic group can each independently be:

[0187] Deuterium, -F, -Cl, -Br, -I, -SF5, -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;

[0188] Each substituted by the following 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, -SF5, -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-C10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 11 )(Q 12 )(Q 13 )、-Ge(Q 11 )(Q 12 )(Q 13 )、-C(=O)(Q 11 )、-S(=O)(Q 11 )、-S(=O)2(Q 11 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-P(=O)(Q 11 )(Q 12 )、-P(=S)(Q 11 )(Q 12 )、or a combination thereof;

[0189] each of C3-C which is unsubstituted or substituted by the following 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C1-C 60 heteroaryloxy, C1-C 60Heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, 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, C7-C 60 alkylaryl, C7-C 60 arylalkyl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C2-C 60 heteroarylalkyl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-C(=O)(Q 21 )、-S(=O)(Q 21 )、-S(=O)2(Q 21 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-P(=O)(Q 21 )(Q 22 )、-P(=S)(Q 21 )(Q 22 )、or a combination thereof;

[0190] -N(Q 31 )(Q 32 )、-Si(Q 31)(Q 32 )(Q 33 )、 -Ge(Q 31 )(Q 32 )(Q 33 )、 -C(=O)(Q 31 )、 -S(=O)(Q 31 )、 -S(=O)2(Q 31 )、 -B(Q 31 )(Q 32 )、 -P(Q 31 )(Q 32 )、 -P(=O)(Q 31 )(Q 32 )、 or -P(=S)(Q 31 )(Q 32 ); or

[0191] a combination thereof.

[0192] As used herein, Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, 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, 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 C7-C 60 alkylaryl, a substituted or unsubstituted C7-C 60 arylalkyl, 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 C2-C 60 alkylheteroaryl, a substituted or unsubstituted C2-C60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 Heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group; or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0193] For example, Q1 to Q3, Q 11 to Q 13 、Q 21 to Q 23 and Q 31 to Q 33 described herein may each independently be:

[0194] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or

[0195] each unsubstituted or substituted with deuterium, C1-C 10 alkyl, phenyl, or a combination thereof, 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.

[0196] In one or more embodiments, the heterocyclic compound may include at least one of Compounds 1 to 83, but the embodiments are not limited thereto:

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205] The heterocyclic compound represented by Formula 1 satisfies the structure of the aforementioned Formula 1 and has a structure in which the group represented by Formula 3 is substituted onto the ring CY1 of Formula 1. Due to this structure, the heterocyclic compound represented by Formula 1 can have excellent light-emitting characteristics, and in particular, a short-wavelength deep blue color can be achieved.

[0206] Although not limited to any particular theory, the heterocyclic compound represented by Formula 1 can have a high singlet (S1) energy level by having the aforementioned structure in which the group represented by Formula 3 and R 11 are connected in the ortho position, and thus can have high photo-orientation. Therefore, when the heterocyclic compound is used as a light-emitting material, Dexter energy transfer can be suppressed, resulting in excellent lifetime characteristics.

[0207] In addition, since the heterocyclic compound represented by Formula 1 includes a combination of R 11 at the ortho position of the group represented by Formula 3 and the group represented by Formula 2 (for example, a terphenyl group), an electronic device including at least one of the heterocyclic compounds represented by Formula 1, such as an organic light-emitting device, can have high efficiency and a long lifetime.

[0208] The highest occupied molecular orbital (HOMO) energy level, lowest unoccupied molecular orbital (LUMO) energy level, singlet (S1) energy level, and triplet (T1) energy level of some compounds of the heterocyclic compound represented by Formula 1 were evaluated using the Gaussian 09 program with molecular structure optimization obtained by density functional theory (DFT) based on B3LYP, and the results are shown in Table 1.

[0209] Table 1

[0210]

[0211]

[0212] Referring to Table 1, it was confirmed that the heterocyclic compound represented by Formula 1 has electrical characteristics suitable for use as a dopant (for example, an emitter or a sensitizer) in an electronic device such as an organic light-emitting device.

[0213] In one or more embodiments, the full width at half maximum (FWHM) of the emission peak of the emission spectrum or electroluminescence spectrum of the heterocyclic compound represented by Formula 1 can be 60 nanometers (nm) or less. For example, the FWHM of the emission peak of the emission spectrum or electroluminescence spectrum of the heterocyclic compound represented by Formula 1 can be from about 5 nm to about 50 nm, from about 7 nm to about 40 nm, or from about 10 nm to about 30 nm.

[0214] The method for synthesizing the heterocyclic compound represented by Formula 1 can be recognized by those skilled in the art with reference to the synthesis examples described later.

[0215] There is no particular limitation on the way to confirm the structure of the heterocyclic compound represented by Formula 1. In one or more embodiments, the structure of the heterocyclic compound can be determined by known methods (e.g., NMR, LC-MS, etc.).

[0216] Organic light-emitting device

[0217] On the other hand, there is provided an organic light-emitting device including the heterocyclic compound represented by Formula 1.

[0218] In one or more embodiments, the organic light-emitting device includes a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and

[0219] wherein the organic layer includes at least one of the heterocyclic compounds represented by Formula 1.

[0220] In one or more embodiments, the emission layer may include at least one of the heterocyclic compounds represented by Formula 1.

[0221] In one or more embodiments, the emission layer may include a host and an emitter, and the emitter may include at least one of the heterocyclic compounds represented by Formula 1.

[0222] In one or more embodiments, based on weight, the amount of the host in the emission layer may be greater than the amount of at least one of the heterocyclic compounds represented by Formula 1 in the emission layer.

[0223] In one or more embodiments, the emission layer may further include a sensitizer.

[0224] In one or more embodiments, the sensitizer may include a phosphorescent compound, a delayed fluorescence compound, or a combination thereof.

[0225] The detailed descriptions of the above host, emitter, and sensitizer are provided herein.

[0226] When the organic light-emitting device includes an emission layer containing at least one of the aforementioned heterocyclic compounds represented by Formula 1, the organic light-emitting device may have a relatively narrow FWHM of the emission peak of the electroluminescence spectrum, excellent efficiency, and long lifetime characteristics.

[0227] In one or more embodiments, the heterocyclic compound represented by Formula 1 can be used as a dopant (e.g., emitter or sensitizer) in the emission layer, and the emission layer may further include a host (i.e., based on weight, the amount of at least one of the heterocyclic compounds represented by Formula 1 in the emission layer may be less than the amount of the host in the emission layer).

[0228] In one or more embodiments, the emissive layer may emit blue light. In one or more embodiments, the emissive layer may emit blue light having a maximum emission wavelength of about 410 nm to about 490 nm.

[0229] The expressions “(the emissive layer) includes at least one heterocyclic compound represented by Formula 1” and “(the emissive layer) includes at least one kind of heterocyclic compound represented by Formula 1” may be used interchangeably herein and may be construed to mean that “(the emissive layer) may include one heterocyclic compound of Formula 1 or two or more different heterocyclic compounds of Formula 1”.

[0230] In one or more embodiments, the emissive layer may include only Compound 1 as the at least one heterocyclic compound represented by Formula 1. In this regard, Compound 1 may be present in the emissive layer of the organic light-emitting device. In one or more embodiments, the emissive layer may include Compound 1 and 2 as the at least one heterocyclic compound represented by Formula 1, wherein Compound 1 and 2 are different from each other.

[0231] Figure 1 description

[0232] Figure 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Hereinafter, the structure and manufacturing method of the organic light-emitting device 10 according to one or more embodiments will be described with respect to Figure 1 the structure and manufacturing method of the organic light-emitting device 10 according to one or more embodiments will be described.

[0233] In Figure 1 the organic light-emitting device 10 includes a first electrode 11, a second electrode 19 facing the first electrode 11, and an organic layer 15 disposed between the first electrode 11 and the second electrode 19.

[0234] The organic layer 15 includes an emissive layer, and may further include a hole transport region disposed between the first electrode 11 and the emissive layer, and an electron transport region disposed between the emissive layer and the second electrode 19.

[0235] A substrate may be additionally disposed under the first electrode 11 or on the second electrode 19. As the substrate, a substrate generally used for 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 (operation), and / or water resistance, may be used.

[0236] The first electrode 11

[0237] The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 onto a substrate, for example. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials having a high work function to facilitate hole injection.

[0238] The first electrode 11 can be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, when the first electrode 11 is a transmissive electrode, the material used to form 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 used to form the first electrode 11 can be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or a combination thereof, but the embodiments are not limited thereto.

[0239] The first electrode 11 can have a single-layer structure or a multi-layer structure including multiple layers.

[0240] Emission layer

[0241] The emission layer can include at least one heterocyclic compound represented by Formula 1.

[0242] The thickness of the emission layer can be about 100 angstroms to about For example, about to about When the thickness of the emission layer is within these ranges, excellent light-emitting characteristics can be obtained without a significant increase in the driving voltage.

[0243] Figure 2 description of

[0244] In one or more embodiments, the heterocyclic compound represented by Formula 1 can be used as a fluorescent emitter.

[0245] In one or more embodiments, the emission layer can further include a host (hereinafter referred to as "host A", where host A is different from the heterocyclic compound represented by Formula 1). Host A can be understood with reference to the host materials described herein, but the embodiments are not limited thereto. Host A can be used as a fluorescent host.

[0246] Reference Figure 2 , the energy transfer according to one or more embodiments is described as follows.

[0247] Singlet excitons can be formed in the host A of the emission layer, and these singlet excitons formed in the host A can be transferred to the fluorescent emitter through (Förster) energy transfer (or, resonance energy transfer (FRET)).

[0248] Since singlet excitons formed in host A only account for 25%, the efficiency of the organic light-emitting device can be further improved as follows: allowing triplet excitons that are formed in host A and account for 75% to fuse with each other and be converted into singlet excitons. That is, by utilizing the triplet-triplet fusion (TTF) mechanism, the efficiency of the organic light-emitting device can be further improved.

[0249] In one or more embodiments, the ratio of the emission component emitted from the heterocyclic compound represented by Formula 1 to the total emission component emitted from the emission layer may be 80% or greater, for example 90% or greater. In one or more embodiments, the ratio of the emission component emitted from the heterocyclic compound represented by Formula 1 to the total emission component emitted from the emission layer may be 95% or greater.

[0250] Here, the heterocyclic compound represented by Formula 1 may emit phosphorescence or delayed fluorescence, while the host may not emit light.

[0251] In one or more embodiments, when the emission layer further includes host A in addition to the heterocyclic compound represented by Formula 1, based on 100 parts by weight of the emission layer, the amount of the heterocyclic compound represented by Formula 1 in the emission layer may be 50 parts by weight or less, for example 30 parts by weight or less, and based on 100 parts by weight of the emission layer, the amount of host A in the emission layer may be 50 parts by weight or greater, for example 70 parts by weight or greater, but the embodiments are not limited thereto.

[0252] In one or more embodiments, when the emission layer further includes host A in addition to the heterocyclic compound represented by Formula 1, host A and the heterocyclic compound may satisfy Condition A:

[0253] Condition A

[0254] E(H A ) S1 >E S1

[0255] Wherein, in Condition A,

[0256] E(H A ) S1 represents the lowest excited singlet state energy level of host A, and

[0257] E S1 represents the lowest excited singlet state energy level of the heterocyclic compound represented by Formula 1.

[0258] Here, E(H A ) S1 and E S1 are evaluated by using the DFT method of the Gaussian program with structural optimization at the B3LYP / 6-31G(d,p) basis set level.

[0259] Figure 3 Description

[0260] In one or more embodiments, the heterocyclic compound represented by Formula 1 can be used as a delayed fluorescence emitter.

[0261] In one or more embodiments, the emissive layer may further include a host (hereinafter referred to as "host B", where host B is different from the heterocyclic compound represented by Formula 1). Host B can be understood with reference to the host materials described herein, but the embodiments are not limited thereto.

[0262] Reference Figure 3 , the energy transfer according to one or more embodiments is described as follows.

[0263] The singlet excitons formed in host B of the emissive layer and accounting for 25% can be transferred to the delayed fluorescence emitter. Additionally, the triplet excitons formed in host B of the emissive layer and accounting for 75% can be transferred to the delayed fluorescence emitter through Dexter energy transfer. Here, at least a part of the energy of the delayed fluorescence emitter in the singlet state can be transferred to the energy in the triplet state through intersystem crossing (ISC). The energy of the triplet state transferred to the delayed fluorescence emitter can be transferred back to the singlet state through reverse intersystem crossing (RISC). Therefore, all of the singlet and triplet excitons generated in the emissive layer can be transferred to the heterocyclic compound, thereby obtaining an organic light emitting device with improved efficiency.

[0264] In one or more embodiments, the ratio of the emission component emitted from the heterocyclic compound represented by Formula 1 to the total emission component emitted from the emissive layer can be 80% or greater, for example 90% or greater. In one or more embodiments, the ratio of the emission component emitted from the heterocyclic compound represented by Formula 1 to the total emission component emitted from the emissive layer can be 95% or greater.

[0265] In this regard, the heterocyclic compound represented by Formula 1 can emit fluorescence and / or delayed fluorescence, and the emission component of the heterocyclic compound represented by Formula 1 can be the sum of the instantaneous emission component of the heterocyclic compound and the delayed fluorescence component related to RISC of the heterocyclic compound. Additionally, host B may not emit light.

[0266] In one or more embodiments, when the emissive layer further includes host B in addition to the heterocyclic compound represented by Formula 1, based on 100 parts by weight of the emissive layer, the amount of the heterocyclic compound represented by Formula 1 in the emissive layer can be 50 parts by weight or less, for example 30 parts by weight or less, and based on 100 parts by weight of the emissive layer, the amount of host B in the emissive layer can be 50 parts by weight or greater, for example 70 parts by weight or greater, but the embodiments are not limited thereto.

[0267] In one or more embodiments, when the emission layer further includes host B in addition to the heterocyclic compound represented by Formula 1, host B and the heterocyclic compound represented by Formula 1 may satisfy Condition B:

[0268] Condition B

[0269] E(H B ) S1 >E S1

[0270] Wherein, in Condition B,

[0271] E(H B ) S1 represents the lowest excited singlet state energy level of host B, and

[0272] E S1 represents the lowest excited singlet state energy level of the heterocyclic compound represented by Formula 1.

[0273] Here, E(H B ) S1 and E S1 are evaluated by using the DFT method of the Gaussian program with structural optimization at the B3LYP / 6-31G(d,p) basis set level.

[0274] Figure 4 description of

[0275] In one or more embodiments, the heterocyclic compound represented by Formula 1 can be used as a fluorescent emitter, and the emission layer may further include a sensitizer, specifically, a delayed fluorescence sensitizer. In this embodiment, the emission layer may further include a host (hereinafter referred to as "host C", where host C is different from the heterocyclic compound represented by Formula 1 and the sensitizer) and a sensitizer (hereinafter referred to as "sensitizer A", where sensitizer A is different from host C and the heterocyclic compound represented by Formula 1). Host C and sensitizer A can be understood by referring to the host material and sensitizer material described later, but the embodiment is not limited thereto.

[0276] In one or more embodiments, the ratio of the emission component emitted from the heterocyclic compound represented by Formula 1 to the total emission component emitted from the emission layer may be 80% or more, for example 90% or more (or for example, 95% or more). For example, the heterocyclic compound represented by Formula 1 may emit fluorescence. In addition, host C and sensitizer A may each not emit light.

[0277] Reference Figure 4 , the energy transfer according to one or more embodiments is described as follows.

[0278] In the host C of the emission layer, singlet and triplet excitons are formed, and these singlet and triplet excitons formed in the host C can first be transferred to the sensitizer A and then transferred back to the heterocyclic compound represented by Formula 1 through FRET. The singlet excitons formed in the host C and accounting for 25% can be transferred to the sensitizer A through FRET, and the energy of the triplet excitons formed in the host C and accounting for 75% can be transferred to the singlet and triplet states of the sensitizer A. Among these, at least a part of the energy of the sensitizer A in the singlet state can be transferred to the energy in the triplet state through ISC. The energy transferred to the triplet state of the sensitizer A can be transferred to the singlet state through RISC, and then, the singlet state energy of the sensitizer A can be transferred to the heterocyclic compound represented by Formula 1 through FRET.

[0279] Therefore, all of the singlet and triplet excitons generated in the emission layer can be transferred to the dopant (e.g., emitter), thereby obtaining an organic light-emitting device with improved efficiency. In addition, since the organic light-emitting device thus obtained has significantly reduced energy loss, the lifetime characteristics of the organic light-emitting device can also be improved.

[0280] Referring to Figure 4 , when the emission layer further includes the host C and the sensitizer A in addition to the heterocyclic compound represented by Formula 1, the heterocyclic compound, the host C, and the sensitizer A can satisfy the conditions C-1 and / or C-2:

[0281] Condition C-1

[0282] S1(H C )≥S1(S A )

[0283] Condition C-2

[0284] S1(S A )≥S1(HC)

[0285] Wherein, in Conditions C-1 and C-2,

[0286] S1(H c ) represents the lowest excited singlet state energy level of the host C,

[0287] S1(S A ) represents the lowest excited singlet state energy level of the sensitizer A, and

[0288] S1(HC) represents the lowest excited singlet state energy level of the heterocyclic compound represented by Formula 1.

[0289] Here, S1(H C )、S1(S A) and S1(HC) were evaluated by the DFT method of the Gaussian program that performs structural optimization at the B3LYP / 6-31G(d,p) basis set level.

[0290] When the host C, the sensitizer A, and the heterocyclic compound represented by Formula 1 satisfy the condition C-1 and / or C-2, FRET from the sensitizer A to the heterocyclic compound represented by Formula 1 can be promoted, thereby improving the light emission efficiency of the organic light-emitting device.

[0291] Figure 5 description

[0292] In one or more embodiments, the heterocyclic compound represented by Formula 1 can be used as a fluorescent emitter, and the emission layer may further include a sensitizer, specifically, a phosphorescent sensitizer.

[0293] In this embodiment, the emission layer may further include a host (hereinafter referred to as "host D", where host D is different from the heterocyclic compound represented by Formula 1 and the sensitizer) and a sensitizer (hereinafter referred to as "sensitizer B", where sensitizer B is different from host D and the heterocyclic compound represented by Formula 1). Host D and sensitizer B can be understood by referring to the host materials and sensitizer materials described herein, but the embodiments are not limited thereto.

[0294] In one or more embodiments, the ratio of the emission component emitted from the heterocyclic compound represented by Formula 1 to the total emission component emitted from the emission layer may be 80% or more, for example 90% or more (or for example, 95% or more). For example, the heterocyclic compound represented by Formula 1 may emit fluorescence. In addition, host D and sensitizer B may each not emit light.

[0295] Reference Figure 5 , the energy transfer according to one or more embodiments is described as follows.

[0296] The triplet excitons formed in host D of the emission layer and accounting for 75% can be transferred to sensitizer B by Dexter energy transfer, and the energy of the singlet excitons formed in host D of the emission layer and accounting for 25% can be transferred to the singlet and triplet states of sensitizer B. Among these, the energy transferred to the singlet state of sensitizer B can be transferred to the triplet state through ISC, and then, the triplet state energy of sensitizer B can be transferred to the heterocyclic compound represented by Formula 1 by FRET.

[0297] Therefore, all the singlet and triplet excitons generated in the emission layer can be transferred to the dopant (for example, the emitter), thereby obtaining an organic light-emitting device with improved efficiency. In addition, since the obtained organic light-emitting device has significantly reduced energy loss, the lifetime characteristics of the organic light-emitting device can also be improved.

[0298] In one or more embodiments, when the emission layer further includes host D and sensitizer B in addition to the heterocyclic compound represented by Formula 1, the heterocyclic compound, host D, and sensitizer B may satisfy Condition D-1 and / or D-2:

[0299] Condition D-1

[0300] T1(H D )≥T1(S B )

[0301] Condition D-2

[0302] T1(S B )≥S1(HC)

[0303] Wherein, in Conditions D-1 and D-2,

[0304] T1(H D ) represents the lowest excited triplet energy level of host D,

[0305] T1(S B ) represents the lowest excited triplet energy level of sensitizer B, and

[0306] S1(HC) represents the lowest excited singlet energy level of the heterocyclic compound represented by Formula 1.

[0307] Here, T1(H D )、T1(S B )、and S1(HC) are evaluated by the DFT method of the Gaussian program with structural optimization at the B3LYP / 6-31G(d,p) basis set level.

[0308] When host D, sensitizer B, and the heterocyclic compound represented by Formula 1 satisfy Condition D-1 and / or D-2, FRET from sensitizer B to the heterocyclic compound represented by Formula 1 can be promoted, thereby improving the light emission efficiency of the organic light emitting device.

[0309] In one or more embodiments, based on the total weight of the emission layer, the amount of the sensitizer in the emission layer may be about 5 wt% to about 50 wt%, for example, about 10 wt% to about 30 wt%. When the amount is within these ranges, energy transfer in the emission layer can be effectively achieved, and thus an organic light emitting device with high efficiency and long life can be achieved.

[0310] In one or more embodiments, based on the total weight of the emission layer, the amount of the heterocyclic compound represented by Formula 1 in the emission layer may be about 0.01 wt% to about 15 wt%, for example, about 0.05 wt% to about 3 wt%, but the embodiments are not limited thereto.

[0311] In one or more embodiments, the heterocyclic compound represented by Formula 1 may further satisfy Condition 5:

[0312] Condition 5

[0313] 0 μs < T 衰减 (HC) < 5 μs

[0314] Wherein, in Condition 5,

[0315] T 衰减 (HC) represents the decay time (microseconds, μs) of the heterocyclic compound represented by Formula 1.

[0316] The decay time of the heterocyclic compound represented by Formula 1 can be calculated from the time-resolved photoluminescence (TRPL) spectrum of a 40 nm thick film (hereinafter referred to as "film HC") at room temperature, and the film is obtained by vacuum co-depositing a host and the heterocyclic compound represented by Formula 1 on a quartz substrate under a vacuum pressure of 10 -7 torr, wherein the host and the heterocyclic compound represented by Formula 1 are included in a weight ratio of 90:10 in the emission layer.

[0317] Figure 6 description

[0318] In one or more embodiments, the heterocyclic compound represented by Formula 1 can be used as a delayed fluorescence emitter, and the emission layer may include a sensitizer, specifically, a delayed fluorescence emitter.

[0319] In this embodiment, the emission layer may further include a host (hereinafter referred to as "host E", where host E is different from the heterocyclic compound and the sensitizer represented by Formula 1) and a sensitizer (hereinafter referred to as "sensitizer C", where sensitizer C is different from host E and the heterocyclic compound). Host E and sensitizer C can be understood by referring to the host materials and sensitizer materials described herein, but the embodiments are not limited thereto.

[0320] In one or more embodiments, the ratio of the emission component emitted from the heterocyclic compound represented by Formula 1 to the total emission component emitted from the emission layer may be 80% or more, for example, 90% or more (or for example, 95% or more). For example, the heterocyclic compound represented by Formula 1 may emit fluorescence and / or delayed fluorescence. In addition, host E and sensitizer C may each not emit light.

[0321] In this regard, the heterocyclic compound represented by Formula 1 may emit fluorescence and / or delayed fluorescence, and the emission component of the heterocyclic compound represented by Formula 1 may be the sum of the instantaneous emission component of the heterocyclic compound represented by Formula 1 and the delayed fluorescence component related to the RISC of the heterocyclic compound represented by Formula 1.

[0322] ReferenceFigure 6 The energy transfer according to one or more embodiments is described below.

[0323] Among the singlet excitons formed in the host E of the emission layer and accounting for 25%, the energy can be transferred to the singlet state of the sensitizer C through FRET, and among the triplet excitons formed in the host E of the emission layer and accounting for 75%, the energy can be transferred to the triplet state of the sensitizer C. Then, the singlet energy of the sensitizer C can be transferred back to the heterocyclic compound represented by Formula 1 through FRET, and the triplet energy of the sensitizer C can be transferred to the heterocyclic compound represented by Formula 1 through Dexter energy transfer. Among these, the energy transferred to the triplet state of the sensitizer C can be transferred back to the singlet state through RISC. In addition, in the case of the sensitizer C, the energy of the triplet excitons formed in the sensitizer C can be transferred to the host E through triplet exciton distribution (TED), and then transferred back to the heterocyclic compound represented by Formula 1, thereby emitting light through RISC.

[0324] Therefore, all of the singlet and triplet excitons generated in the emission layer can be transferred to the dopant (e.g., emitter), thereby obtaining an organic light-emitting device with improved efficiency. In addition, since the obtained organic light-emitting device has significantly reduced energy loss, the lifetime characteristics of the organic light-emitting device can also be improved.

[0325] In one or more embodiments, when the emission layer further includes the host E and the sensitizer C in addition to the heterocyclic compound represented by Formula 1, the heterocyclic compound, the host E, and the sensitizer C may satisfy conditions E-1, E-2, and / or E-3:

[0326] Condition E-1

[0327] S1(H E )≥S1(S C )

[0328] Condition E-2

[0329] S1(S C )≥S1(HC)

[0330] Condition E-3

[0331] T1(S C )≥T1(HC)

[0332] Wherein, in conditions E-1, E-2, and E-3,

[0333] S1(H E ) represents the lowest excited singlet energy level of the host E,

[0334] S1(S C ) represents the lowest excited singlet energy level of the sensitizer C,

[0335] S1(HC) represents the lowest excited singlet energy level of the heterocyclic compound represented by Formula 1,

[0336] T1(S C ) represents the lowest excited triplet energy level of the sensitizer C, and

[0337] T1(HC) represents the lowest excited triplet energy level of the heterocyclic compound represented by Formula 1.

[0338] Here, S1(H E ), S1(S C ), S1(HC), T1(S C ) and T1(HC) are evaluated by the DFT method of the Gaussian program with structural optimization at the B3LYP / 6-31G(d,p) basis set level.

[0339] When the host E, the sensitizer C, and the heterocyclic compound represented by Formula 1 satisfy the conditions E-1, E-2, and / or E-3, Dexter transfer and FRET from the sensitizer C to the heterocyclic compound represented by Formula 1 can be promoted, thereby improving the light emission efficiency of the organic light-emitting device.

[0340] In one or more embodiments, based on the total weight of the emission layer, the amount of the sensitizer C in the emission layer can be about 5 wt% to about 50 wt%, such as about 10 wt% to about 30 wt%. When the amount is within these ranges, energy transfer in the emission layer can be effectively achieved, and thus an organic light-emitting device with high efficiency and long lifetime can be achieved.

[0341] In one or more embodiments, based on the total weight of the emission layer, the amount of the heterocyclic compound represented by Formula 1 in the emission layer can be about 0.01 wt% to about 15 wt%, such as about 0.05 wt% to about 3 wt%, but the embodiments are not limited thereto.

[0342] The host in the emission layer

[0343] In one or more embodiments, the host may not include metal atoms.

[0344] In one or more embodiments, the host may include at least one of the following: a fluorene-containing compound, a carbazole-containing compound, a dibenzofuran-containing compound, a dibenzothiophene-containing compound, an indolocarbazole-containing compound, an indolocarbazole-containing compound, a benzofurancarbazole-containing compound, a benzothiophenecarbazole-containing compound, an acridine-containing compound, a dihydroacridine-containing compound, a triindolobenzene-containing compound, a pyridine-containing compound, a pyrimidine-containing compound, a triazine-containing compound, a silicon-containing compound, a cyano-containing compound, a phosphine oxide-containing compound, a sulfoxide-containing compound, or a sulfonyl-containing compound.

[0345] For example, the host may be a compound including at least one carbazole ring and at least one cyano group, or a compound containing a phosphine oxide.

[0346] In one or more embodiments, the host may be composed of one type of host. When the host is composed of one type of host, the one type of host may be a bipolar host, an electron transporting host, or a hole transporting host, which will be described herein.

[0347] In one or more embodiments, the host may be a mixture of two or more different types of hosts. In one or more embodiments, the host may be a mixture of an electron transporting host and a hole transporting host, a mixture of two different types of electron transporting hosts, or a mixture of two different types of hole transporting hosts. The electron transporting host and the hole transporting host can be understood by referring to the description provided later.

[0348] In one or more embodiments, the host may include: an electron transporting host including at least one electron transporting moiety; and a hole transporting host not including an electron transporting moiety.

[0349] The electron transporting moiety used herein may be a cyano group, a ring group containing nitrogen with a deficient π electron, or a group represented by one of the following formulas:

[0350]

[0351] Wherein, in the above formulas, *, *', and *" each represent a binding site to an adjacent atom.

[0352] In one or more embodiments, the electron transporting host in the emission layer may include at least one of a cyano group and a ring group containing nitrogen with a deficient π electron.

[0353] In one or more embodiments, the electron transporting host in the emission layer may include at least one cyano group.

[0354] In one or more embodiments, the electron transport host in the emissive layer may include at least one cyano group and at least one ring group containing nitrogen with a deficient π - electron.

[0355] In one or more embodiments, the host may include an electron transport host and a hole transport host, where the electron transport host may include at least one ring group that does not contain nitrogen with a deficient π - electron and at least one electron transport moiety, and the hole transport host may include at least one ring group that does not contain nitrogen with a deficient π - electron and may not include an electron transport moiety.

[0356] As used herein, the term "ring group containing nitrogen with a deficient π - electron" refers to a ring group having at least one * - N = *' moiety, and for example, may include imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyridazine group, pyrimidine 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, and azacarbazole group; or a fused - ring group in which two or more ring groups containing nitrogen with a deficient π - electron are fused to each other.

[0357] In one or more embodiments, the ring group that does not contain nitrogen with a deficient π - electron may be a benzene group, heptalene group, indene group, naphthalene group, azulene group, indacene group, acenaphthene group, fluorene group, spiro - bifluorene 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, indacarbazole group, indolocarbazole group, benzofurocarbazole group, benzothiophenocarbazole group, and triindolobenzene group; or a fused - ring group of two or more ring groups that do not contain nitrogen with a deficient π - electron, but the embodiments are not limited thereto.

[0358] In one or more embodiments, when the host is a mixture of an electron-transporting host and a hole-transporting host, the weight ratio of the electron-transporting host to the hole-transporting host can be from about 1:9 to about 9:1, such as from about 2:8 to about 8:2, or such as from about 4:6 to about 6:4, or such as 5:5. When the weight ratio of the electron-transporting host to the hole-transporting host satisfies the above range, a balance between hole and electron transport in the emissive layer can be achieved.

[0359] The host can include at least one of 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphthalen-2-yl)anthracene (TBADN), 9,10-di(naphthalen-2-yl)anthracene (ADN) (also referred to as "DNA"), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), 1,3-bis(N-carbazolyl)benzene (mCP), Compound H50 or Compound H51, but the embodiments are not limited thereto:

[0360]

[0361] In one or more embodiments, the host can further include a compound represented by Formula 301:

[0362] Formula 301

[0363]

[0364] Wherein, in Formula 301, Ar 111 and Ar 112 can each independently be:

[0365] phenylene, naphthylene, phenanthrylene or pyrenylene; or

[0366] phenylene, naphthylene, phenanthrylene or pyrenylene each substituted with at least one of phenyl, naphthyl or anthryl.

[0367] In Formula 301, Ar 113 to Ar 116 can each independently be:

[0368] C1-C 10 alkyl, phenyl, naphthyl, phenanthryl or pyrenyl; or

[0369] phenyl, naphthyl, phenanthryl or pyrenyl each substituted with at least one of phenyl, naphthyl or anthryl.

[0370] In Formula 301, g, h, i and j can each independently be an integer from 0 to 4, or such as 0, 1 or 2.

[0371] In Formula 301, Ar 113 to Ar 116 may each independently be:

[0372] C1-C substituted by at least one of phenyl, naphthyl or anthryl 10 alkyl;

[0373] phenyl, naphthyl, anthryl, pyrenyl, phenanthryl, or fluorenyl;

[0374] phenyl, naphthyl, anthryl, pyrenyl, phenanthryl or fluorenyl each substituted by at least one of the following: deuterium, -F, -Cl, -Br, -I, -SF5, 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, C1-C 60 alkylthio, phenyl, naphthyl, anthryl, pyrenyl, phenanthryl or fluorenyl; or

[0375]

[0376] However, the embodiments are not limited thereto.

[0377] In one or more embodiments, the host may include a compound represented by Formula 302:

[0378] Formula 302

[0379]

[0380] wherein, in Formula 302, Ar 122 to Ar 125 are each the same as described for Ar in Formula 301 113 described.

[0381] In Formula 302, Ar 126 and Ar 127 may each independently be C1-C 10 alkyl (e.g., methyl, ethyl, propyl, etc.).

[0382] In Formula 302, k and l may each independently be an integer from 0 to 4. For example, k and l may each independently be 0, 1 or 2.

[0383] In one or more embodiments, the host may include at least one of Compounds H1 to H26:

[0384]

[0385]

[0386]

[0387] In one or more embodiments, the host may consist of one type of compound. For example, the one type of compound may be optionally selected from a first material (e.g., a hole-transporting host) or a second material (e.g., an electron-transporting host).

[0388] In one or more embodiments, the host may include two or more types of compounds. For example, the host may include two or more types of different hole-transporting hosts; two or more types of different electron-transporting hosts; or a combination of one or more types of hole-transporting hosts and one or more types of electron-transporting hosts.

[0389] The emitter in the emission layer

[0390] The emitter may include at least one of the heterocyclic compounds represented by Formula 1.

[0391] The sensitizer in the emission layer

[0392] In one or more embodiments, the sensitizer may include a phosphorescent compound.

[0393] In one or more embodiments, the phosphorescent compound may be an organometallic compound including at least one type of metal.

[0394] In one or more embodiments, the organometallic compound may include at least one type of metal (M 11 ) selected from transition metals and an organic ligand (L 11 ), wherein L 11 and M 11 may form 1, 2, 3, or 4 cyclometalated rings.

[0395] In one or more embodiments, the organometallic compound may be represented by Formula 101:

[0396] Formula 101

[0397] M 11 (L 11 ) n11 (L 12 ) n12

[0398] wherein, in Formula 101,

[0399] M 11 may be a transition metal,

[0400] L 11may be a ligand represented by one of Formulae 1-1 to 1-4,

[0401] L 12 may be a monodentate ligand or a bidentate ligand,

[0402] n11 may be 1, and

[0403] n12 may be 0, 1 or 2,

[0404]

[0405] wherein, in Formulae 1-1 to 1-4,

[0406] A1 to A4 may each independently be a substituted or unsubstituted C5-C 30 carbocyclic group, a substituted or unsubstituted C1-C 30 heterocyclic group, or an acyclic group,

[0407] Y 11 to Y 14 may each independently be a chemical bond, O, S, N(R 91 ), B(R 91 ), P(R 91 ), or C(R 91 )(R 92 ),

[0408] T1 to T4 may each independently be a single bond, a double bond, *-N(R 93 )-*', *-B(R 93 )-*', *-P(R 93 )-*', *-C(R 93 )(R 94 )-*', *-Si(R 93 )(R 94 )-*', *-Ge(R 93 )(R 94 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 93 )=*', *=C(R 93 )-*', *-C(R 93 )=C(R 94 )-*', *-C(=S)-*', or *-C≡C-*',

[0409] substituents of the substituted C5-C 30 carbocyclic group, substituents of the substituted C1-C 30 heterocyclic group, and R 91 to R 94may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro 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 substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C1-C 60 alkylthio group, 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 C7-C 60 alkylaryl group, a substituted or unsubstituted C7-C 60 arylalkyl 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 C2-C 60 alkylheteroaryl group, a substituted or unsubstituted C2-C 60 heteroarylalkyl group, a substituted or unsubstituted C1-C 60 heteroaryloxy group, a substituted or unsubstituted C1-C 60 heteroarylthio group, a substituted or unsubstituted monovalent aromatic fused polycyclic group, a substituted or unsubstituted monovalent aromatic fused heteropolycyclic group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), wherein the substituents of the substituted C5-C 30 carbocyclic group and the substituents of the substituted C1-C 30 heterocyclic group cannot be hydrogen,

[0410] *1, *2, *3 and *4 each represent a binding site to M 11 and

[0411] Q1 to Q3 may each independently be:

[0412] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazono, 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 C7-C 60 alkylaryl, substituted or unsubstituted C7-C 60 arylalkyl, C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 alkylheteroaryl, substituted or unsubstituted C2-C 60 heteroarylalkyl, substituted or unsubstituted C1-C 60 heteroaryloxy, substituted or unsubstituted C1-C 60 heteroarylthio, substituted or unsubstituted monovalent aromatic fused polycyclic group, substituted or unsubstituted monovalent aromatic fused heteropolycyclic group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group,

[0413] substituted by deuterium, -F, cyano, C1-C 60 alkyl, or C6-C 60 aryl of at least one substituted C1-C 60 alkyl, or

[0414] substituted by deuterium, -F, cyano, C1-C 60 alkyl, or C6-C 60 aryl of at least one substituted C6-C 60 aryl.

[0415] In one or more embodiments, the transition metal may include platinum (Pt), palladium (Pd), gold (Au), iridium (Ir), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm) or rhodium (Rh).

[0416] In one or more embodiments, the sensitizer may include a delayed fluorescence compound.

[0417] In one or more embodiments, the delayed fluorescence compound may be represented by Formula 101 or 102:

[0418]

[0419] Wherein, in Formulas 101 and 102,

[0420] A 21 may be an acceptor group,

[0421] D 21 may be a donor group,

[0422] m21 may be 1, 2, or 3, and n21 may be 1, 2, or 3,

[0423] The sum of n21 and m21 in Formula 101 may be 5 or less, and the sum of n21 and m21 in Formula 102 may be 6 or less,

[0424] R 201 may be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, 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 C7-C 60 alkylaryl, a substituted or unsubstituted C7-C 60 arylalkyl, 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 C2-C 60 alkylheteroaryl, a substituted or unsubstituted C2-C 60 heteroarylalkyl, a substituted or unsubstituted C1-C 60 heteroaryloxy, a substituted or unsubstituted C1-C60 Heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), where multiple Rs 201 may optionally be bonded together to form a substituted or unsubstituted C5-C 30 carbocyclic group or a substituted or unsubstituted C1-C 30 heterocyclic group, and

[0425] Q1 to Q3 may each independently be:

[0426] hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, 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, C7-C 60 alkylaryl, substituted or unsubstituted C7-C 60 arylalkyl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, substituted or unsubstituted C2-C 60 heteroarylalkyl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent aromatic fused polycyclic group, monovalent aromatic fused heteropolycyclic group, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group,

[0427] substituted C1-C by deuterium, -F, cyano, C1-C 60 alkyl, or C6-C 60 aryl of at least one substituted C1-C 60 alkyl; or

[0428] substituted by deuterium, -F, cyano, C1-C60 An alkyl group and at least one substituted C6-C 60 aryl group of C6-C 60 aryl group.

[0429] In one or more embodiments, in Formulas 101 and 102, A 21 may be a substituted or unsubstituted ring group that does not contain a nitrogen atom lacking π electrons.

[0430] In one or more embodiments, the ring group that does not contain a nitrogen atom lacking π electrons may 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 spiro-bifluorene 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, a group, a tetracene group, a picene group, a perylene group, a pentaphene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indacarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothiophenocarbazole group, a triindolobenzene group; or a fused ring group of two or more ring groups that do not contain a nitrogen atom lacking π electrons, but the embodiments are not limited thereto.

[0431] In one or more embodiments, in Formulas 101 and 102, D 21 may be:

[0432] -F, a cyano group, or a ring group containing a nitrogen atom lacking π electrons;

[0433] each C1-C substituted with at least one of -F or a cyano group 60 alkyl group, a ring group containing a nitrogen atom lacking π electrons, or a ring group that does not contain a nitrogen atom lacking π electrons; or

[0434] a ring group containing a nitrogen atom lacking π electrons substituted with at least one of deuterium, a C1-C 60 alkyl group, a ring group containing a nitrogen atom lacking π electrons, or a ring group that does not contain a nitrogen atom lacking π electrons.

[0435] In one or more embodiments, the ring group that does not contain a nitrogen atom lacking π electrons may be the same as those described above.

[0436] As used herein, the term "ring group containing π-deficient nitrogen" refers to a ring group having at least one *-N=*' moiety, and may be, for example, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, 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, a benzimidazole group, or a fused ring group of two or more ring groups containing π-deficient nitrogen.

[0437] In one or more embodiments, based on weight or volume, the amount of the sensitizer in the emissive layer may be greater than the amount of the emitter in the emissive layer. For example, the volume ratio of the sensitizer to the emitter may be in the range of about 30:0.1 to about 10:3 or about 10:0.1 to about 20:5. In one or more embodiments, the weight ratio of the sensitizer to the emitter may be in the range of about 10:0.1 to about 20:5. In one or more embodiments, the weight ratio of the host and the sensitizer in the emissive layer may be in the range of about 60:40 to about 95:5 or about 70:30 to about 90:10. In one or more embodiments, the weight ratio of the host and the sensitizer in the emissive layer may be in the range of about 60:40 to about 95:5. When the amounts within the above ranges are satisfied, the organic light-emitting device may have improved luminous efficiency and / or long lifetime characteristics.

[0438] Figure 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Hereinafter, with respect to Figure 1 The structure and manufacturing method of an organic light-emitting device 10 according to one or more embodiments of the present disclosure will be described. The organic light-emitting device 10 has a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are sequentially stacked.

[0439] A substrate may be additionally disposed under the first electrode 11 or on the second electrode 19. As the substrate, 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 (operation), and waterproofness, may be used.

[0440] The first electrode 11 can be formed by, for example, depositing or sputtering a material for forming the first electrode 11 onto a substrate. The first electrode 11 can be an anode. The material for forming the first electrode 11 can be selected from materials having a high work function to facilitate hole injection. The first electrode 11 can be a reflective electrode, a semi-transmissive reflective electrode, or a transmissive electrode. The material for forming the first electrode 11 can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 can be a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0441] The first electrode 11 can have a single-layer structure or a multi-layer structure including multiple layers. For example, the first electrode 11 can have a three-layer structure of ITO / Ag / ITO, but the embodiments are not limited thereto.

[0442] The organic layer 15 is disposed on the first electrode 11.

[0443] The organic layer 15 can include a hole transport region; an emission layer; and an electron transport region.

[0444] The hole transport region can be disposed between the first electrode 11 and the emission layer.

[0445] The hole transport region can include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.

[0446] The hole transport region can include only a hole injection layer or a hole transport layer. The hole transport region can have a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / electron blocking layer, or a hole injection layer / first hole transport layer / second hole transport layer / electron blocking layer structure, where the constituent layers are stacked in this order sequentially from the first electrode 11.

[0447] When the hole transport region includes a hole injection layer, the hole injection layer can be formed on the first electrode 11 by using various methods such as vacuum deposition, spin coating, casting, and / or Langmuir-Blodgett (LB) deposition, but the embodiments are not limited thereto.

[0448] When the hole injection layer is formed by a vacuum deposition method, the deposition conditions can vary depending on the compound used as the material for forming the hole injection layer, the desired structure and thermal properties of the hole injection layer, etc. For example, the deposition temperature can be about 100 °C to about 500 °C, the vacuum pressure can be about 10 -8 torr to about 10 -3 torr, and the deposition rate can be about 0.01 Å / second to about However, the embodiments are not limited thereto.

[0449] When forming the hole injection layer by a spin coating method, the coating conditions may vary depending on the compound used as the material for forming the hole injection layer, the structure and thermal properties of the desired hole injection layer, etc. For example, the coating rate may be about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and the temperature for heat treatment to remove the solvent after coating may be about 80 °C to about 200 °C, however, the embodiments are not limited thereto.

[0450] In this regard, the conditions for forming the hole transport layer and the electron blocking layer can be understood by referring to the conditions for forming the hole injection layer.

[0451] The hole transport region may include at least one of 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), β-NPB, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, or a compound represented by Formula 202:

[0452]

[0453] Formula 201

[0454]

[0455] Formula 202

[0456]

[0457] Wherein, in Formula 201, Ar 101 and Ar 102 may each independently be:

[0458] Phenylene, indenylene, naphthylene, azulylene, heptaleneylene, acenaphthylene, fluorenylene, phenalenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrenylene, -ylene, tetracenylene, picenylene, perylenylene, or pentacenylene; or

[0459] Phenylene, indenylene, naphthylene, azulylene, heptaleneylene, acenaphthylene, fluorenylene, phenalenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo[9,10]phenanthrylene, pyrenylene, -ylene, tetracenylene, picenylene, perylenylene, or pentacenylene, each substituted with: deuterium, -F, -Cl, -Br, -I, -SF5, 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 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C1-C 60 alkylthio, C3-C 10 cycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkylaryl, C7-C 60 arylalkyl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C2-C 60 heteroarylalkyl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or a combination thereof.

[0460] In Formula 201, xa and xb can each independently be an integer from 0 to 5, or can each independently be 0, 1, or 2. For example, xa can be 1 and xb can be 0, but the embodiments are not limited thereto.

[0461] In Formulas 201 and 202, R 101 to R 108 、R 111 to R 119 、and R 121 to R 124 can each independently be:

[0462] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, 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 (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), C1-C 10 alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentyloxy, etc.), or C1-C 10 alkylthio;

[0463] C1-C each substituted with the following 10 alkyl, C1-C 10 alkoxy, or C1-C 10 alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, 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, or a combination thereof;

[0464] phenyl, naphthyl, anthryl, fluorenyl, or pyrenyl; or

[0465] phenyl, naphthyl, anthryl, fluorenyl, or pyrenyl each substituted with the following: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, 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, C1-C 10 alkoxy, C1-C 10 alkylthio, or a combination thereof, but the embodiments are not limited thereto.

[0466] In Formula 201, R 109 may be:

[0467] phenyl, naphthyl, anthryl, or pyridyl; or

[0468] phenyl, naphthyl, anthryl, or pyridyl each substituted with the following: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, 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 20 alkyl, C1-C 20 alkoxy, C1-C 20 alkylthio, phenyl, naphthyl, anthryl, pyridyl, or a combination thereof.

[0469] In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but the embodiments are not limited thereto:

[0470] Formula 201A

[0471]

[0472] Among them, in Formula 201A, R 101 , R 111 , R 112 and R 109 can each be as defined herein.

[0473] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include at least one of Compounds HT1 to HT20, but the embodiments are not limited thereto:

[0474]

[0475]

[0476]

[0477] The thickness of the hole transport region may be about to about For example, about to about When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about to about For example, about to about and the thickness of the hole transport layer may be about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in the driving voltage.

[0478] In addition to the above materials, the hole transport region may further include a charge generation material for improving the conduction properties. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region.

[0479] The charge generation material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, or a cyanide-containing compound, but the embodiments are not limited thereto. Non-limiting examples of the p-dopant include quinone derivatives such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; or cyanide-containing compounds such as Compound HT-D1 or F12, but are not limited thereto:

[0480]

[0481] The hole transport region may further include a buffer layer.

[0482] The buffer layer may compensate for the optical resonance distance according to the wavelength of light emitted from the emission layer 15, and thus, the efficiency of the formed organic light-emitting device may be improved.

[0483] Meanwhile, when the hole transport region includes an electron blocking layer, the material for forming the electron blocking layer may be selected from the aforementioned materials for forming the hole transport region and the host materials to be described later, but the embodiments are not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material for forming the electron blocking layer may be mCP to be described later.

[0484] Then, the emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied when forming the hole injection layer, although the deposition or coating conditions may vary depending on the material used to form the emission layer.

[0485] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer. Due to the structure in which the red emission layer, the green emission layer, and / or the blue emission layer are stacked, the emission layer may emit white light.

[0486] When the emission layer includes a host and a dopant, based on 100 parts by weight of the host, the amount of the dopant in the emission layer may be about 0.01 part by weight to about 15 parts by weight, but the embodiments are not limited thereto.

[0487] The thickness of the emission layer may be about to about For example, about to about When the thickness of the emission layer is within these ranges, excellent light-emitting characteristics may be obtained without a significant increase in the driving voltage.

[0488] The electron transport region may be disposed on the emission layer.

[0489] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0490] For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure, or an electron transport layer / electron injection layer structure, but the embodiments are not limited thereto. The electron transport layer may have a single-layer structure or a multi-layer structure including multiple layers.

[0491] The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region may be understood by referring to the conditions for forming the hole injection layer.

[0492] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), or bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-ol)aluminum (BAlq), but embodiments are not limited thereto:

[0493]

[0494] The thickness of the hole blocking layer may be about to about For example, about to about When the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics can be obtained without a significant increase in the driving voltage.

[0495] The electron transport layer may include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinoline)aluminum (Alq3), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-ol)aluminum (BAlq), 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), or 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), but embodiments are not limited thereto:

[0496]

[0497] The electron transport layer may include at least one of compounds ET1 to ET25, but embodiments are not limited thereto:

[0498]

[0499]

[0500]

[0501] 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.

[0502] In addition to the foregoing materials, the electron transport layer may further include a metal-containing material.

[0503] The metal-containing material may include a Li complex. The Li complex may include, for example, the compound ET-D1 (lithium 8-hydroxyquinoline, LiQ) or ET-D2, but the embodiments are not limited thereto:

[0504]

[0505] The electron transport region may further include an electron injection layer that promotes the injection of electrons from the second electrode 19.

[0506] The electron injection layer may include LiQ, LiF, NaCl, CsF, Li2O, BaO, or a combination thereof.

[0507] The thickness of the electron injection layer may be about to about For example, about to about When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.

[0508] The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. The material for forming the second electrode 19 may be a metal, an alloy, a conductive compound, or a combination thereof each having a relatively low work function. For example, the material for forming the second electrode 19 may include lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. For manufacturing a top-emission type light-emitting device, a transmissive electrode formed of ITO or IZO can be used as the second electrode 19.

[0509] In the above, an organic light-emitting device has been described with reference to Figure 1 However, the embodiments are not limited thereto.

[0510] On the other hand, an electronic device including the organic light-emitting device is provided.

[0511] In addition to the above organic light-emitting device, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, wherein either the source electrode or the drain electrode may be electrically connected to either the first electrode or the second electrode of the organic light-emitting device.

[0512] On the other hand, a diagnostic composition including at least one of the heterocyclic compounds represented by Formula 1 is provided.

[0513] The diagnostic composition may include at least one type of the heterocyclic compound represented by Formula 1.

[0514] The heterocyclic compound represented by Formula 1 may be capable of providing high luminescence efficiency, and thus a diagnostic composition including at least one of the heterocyclic compounds represented by Formula 1 may have high diagnostic efficiency.

[0515] The diagnostic composition can be used in various applications including diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc., but the embodiments are not limited thereto.

[0516] As used herein, the term "C1-C 60 alkyl" refers to a straight-chain or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. As used herein, the term "C1-C 60 alkylene" refers to a divalent group having the same structure as C1-C 60 alkyl.

[0517] C1-C 60 alkyl, C1-C 20 alkyl and / or C1-C 10 alkyl non-limiting examples include 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, or tert-decyl, each unsubstituted or substituted by: 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. For example, the group represented by Formula 9-33 may be a C6 alkyl, such as tert-butyl substituted by two methyl groups.

[0518] 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 its non-limiting examples include methoxy, ethoxy, isopropoxy, n-propoxy, butoxy, pentyloxy, etc.

[0519] As used herein, the term "C1-C 60 alkylthio" refers to a group represented by -SA 101’ (where A 101’ is C1-C 60a monovalent group represented by (alkyl).

[0520] As used herein, the term "C2-C 60 alkenyl" refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond at the middle or end of a C2-C 60 alkyl, and non-limiting examples thereof include vinyl, propenyl, butenyl, etc. As used herein, the term "C2-C 60 alkenylene" refers to a divalent group having the same structure as a C2-C 60 alkenyl.

[0521] 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 a C2-C 60 alkyl, and non-limiting examples thereof include ethynyl, propynyl, etc. As used herein, the term "C2-C 60 alkynylene" refers to a divalent group having the same structure as a C2-C 60 alkynyl.

[0522] As used herein, the term "C3-C 10 cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms as ring-forming atoms. As used herein, the term "C3-C 10 cycloalkylene" refers to a divalent group having the same structure as a C3-C 10 cycloalkyl.

[0523] C3-C 10 Non-limiting examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornanyl), bicyclo[2.2.2]octyl, etc.

[0524] As used herein, the term "C1-C 10 heterocycloalkyl" refers to a monovalent saturated ring group having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as ring-forming atoms and 1 to 10 carbon atoms as ring-forming atoms. As used herein, the term "C1-C 10 heterocycloalkylene" refers to a divalent group having the same structure as a C1-C 10 heterocycloalkyl.

[0525] C1-C 10 Non-limiting examples of heterocycloalkyl include silacyclopentyl, silacyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, tetrahydrothienyl, etc.

[0526] As used herein, the term "C3-C 10 cycloalkenyl" refers to a monovalent hydrocarbon cyclic group having 3 to 10 carbon atoms as ring-forming atoms in its ring, at least one carbon-carbon double bond, and no aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, cycloheptenyl, etc. As used herein, the term "C3-C 10 subcycloalkenyl" refers to a divalent group having the same structure as C3-C 10 cycloalkenyl.

[0527] As used herein, the term "C1-C 10 heterocycloalkenyl" refers to a monovalent cyclic group having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as ring-forming atoms, 1 to 10 carbon atoms as ring-forming atoms, and at least one double bond, and no aromaticity. Non-limiting examples of C1-C 10 heterocycloalkenyl include 2,3-dihydrofuranyl, 2,3-dihydrothienyl, etc. As used herein, the term "C1-C 10 subheterocycloalkenyl" refers to a divalent group having the same structure as C1-C 10 heterocycloalkenyl.

[0528] As used herein, the term "C6-C 60 aryl" refers to a monovalent group having a carbocyclic aromatic ring system having 6 to 60 carbon atoms as ring-forming atoms, and as used herein, the term "C6-C 60 subaryl" refers to a divalent group having a carbocyclic aromatic ring system having 6 to 60 carbon atoms as ring-forming atoms. Non-limiting examples of C6-C 60 aryl include phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, yl, etc. When C6-C 60 aryl and C6-C 60 subaryl each include two or more rings, the rings may be fused to each other.

[0529] As used herein, the term "C7-C 60 alkylaryl" refers to a C6-C 54 aryl substituted with at least one C1-C 59 alkyl. As used herein, the term "C7-C 60 arylalkyl" refers to a C1-C 59 alkyl substituted with at least one C6-C 54 aryl.

[0530] As used herein, the term "C1-C 60"Heteroaryl" refers to a monovalent group having a heteroaromatic ring system as follows: having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring-forming atom and 1 to 60 carbon atoms as ring-forming atoms, and the term "C1-C 60 "Heteroarylene" refers to a divalent group having a heteroaromatic ring system as follows: having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge 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, isoquinolinyl, etc. When C1-C 60 heteroaryl and C1-C 60 heteroarylene each include two or more rings, the rings may be fused to each other.

[0531] As used herein, the term "C2-C 60 "Alkylheteroaryl" refers to a C1-C 59 heteroaryl substituted with at least one C1-C 59 alkyl. As used herein, the term "C2-C 60 "Heteroarylalkyl" refers to a C1-C 59 alkyl substituted with at least one C1-C 59 heteroaryl.

[0532] As used herein, the term "C6-C 60 "Aryloxy" refers to -OA 102 (where A 102 is a C6-C 60 aryl), and as used herein, the term "C6-C 60 "Arylthio" refers to -SA 103 (where A 103 is a C6-C 60 aryl).

[0533] As used herein, the term "C1-C 60 "Heteroaryloxy" means -OA 104 (where A 104 is a C1-C 60 heteroaryl), and as used herein, the term "C1-C 60 "Heteroarylthio" means -SA 105 (where A 105 is a C1-C 60 heteroaryl).

[0534] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group having two or more rings fused to each other, having only carbon atoms as ring-forming atoms, and being non-aromatic in its overall structure (e.g., having 8 to 60 carbon atoms). Non-limiting examples of the monovalent non-aromatic fused polycyclic group include fluorenyl groups and the like. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having the same structure as the above-described monovalent non-aromatic fused polycyclic group.

[0535] 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 B, N, O, P, Si, S, Se, and Ge in addition to carbon atoms as ring-forming atoms, and being non-aromatic in its overall structure (e.g., having 1 to 60 carbon atoms). Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic group include carbazolyl groups and the like. 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.

[0536] As used herein, the term "C5-C 30 carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring-forming atoms. The C5-C 30 carbocyclic group can be a monocyclic group or a polycyclic group. As used herein, non-limiting examples of "(unsubstituted or substituted by at least one R 1a substituted) C5-C 30 carbocyclic group" include (each unsubstituted or substituted by at least one R 1a substituted) adamantyl group, norbornene group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptane (norbornane) group, bicyclo[2.2.2]octyl group, cyclopentyl group, cyclohexyl group, cyclohexene group, benzene group, naphthalene group, anthracene group, phenanthrene group, benzo[9,10]phenanthrene group, pyrene group, group, 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, indene group, fluorenyl group, etc.

[0537] As used herein, the term "C1-C 30 heterocyclic group" refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge in addition to 1 to 30 carbon atoms as ring-forming atoms. The C1-C 30 heterocyclic group can be a monocyclic group or a polycyclic group. As used herein, "(unsubstituted or substituted by at least one R 1a substituted) C1-C 30Non-limiting examples of "heterocyclic group" include (each unsubstituted or substituted by at least one R 1a substituted) thiophene group, furan group, pyrrole group, silole group, borole group, phosphole group, selenophene group, germole group, benzothiophene group, benzofuran group, indole group, silole group, benzosilole group, benzoborole group, benzophosphole group, benzoselenophene group, benzogermole group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzosilole group, dibenzoborole group, dibenzophosphole group, dibenzoselenophene group, dibenzogermole group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilole group, azabenzoborole group, azabenzophosphole group, azabenzoselenophene group, azabenzogermole group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzoselenophene group, azadibenzogermole group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, etc.

[0538] In this specification, "TMS" represents *-Si(CH3)3, and "TMG" represents *-Ge(CH3)3.

[0539] 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 10Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkylaryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C2-C 60 Alkylheteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 Heteroarylthio, substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of a substituted monovalent non-aromatic fused heteropolycyclic group may be:

[0540] Deuterium, -F, -Cl, -Br, -I, -SF5, -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;

[0541] 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, -SF5, -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, C7-C 60 Alkylaryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 11 )(Q 12 )(Q 13 ), -Ge(Q 11 )(Q 12 )(Q 13 ), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), or a combination thereof;

[0542] C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkylaryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group;

[0543] C3-C each substituted by the following 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkylaryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60Heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, 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, C7-C 60 alkylaryl, C7-C 60 arylalkyl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C2-C 60 heteroarylalkyl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-C(=O)(Q 21 )、-S(=O)(Q 21 )、-S(=O)2(Q 21 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-P(=O)(Q 21 )(Q 22 )、-P(=S)(Q 21 )(Q 22 )、or a combination thereof; or

[0544] -N(Q 31 )(Q 32 )、-Si(Q 31)(Q 32 )(Q 33 )、 -Ge(Q 31 )(Q 32 )(Q 33 )、 -C(=O)(Q 31 )、 -S(=O)(Q 31 )、 -S(=O)2(Q 31 )、 -B(Q 31 )(Q 32 )、 -P(Q 31 )(Q 32 )、 -P(=O)(Q 31 )(Q 32 )、 or -P(=S)(Q 31 )(Q 32 ), and

[0545] Q1 to Q3, Q 11 to Q 13 、 Q 21 to Q 23 、 and Q 31 to Q 33 can 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 C2-C 10 heterocycloalkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 alkylaryl, 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, C2-C 60 alkylheteroaryl, C2-C 60 heteroarylalkyl, C1-C 60 heteroaryloxy, C1-C60 A heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0546] Hereinafter, compounds and organic light-emitting devices according to one or more embodiments will be described in further detail with reference to synthetic examples and embodiments. However, the following examples are not intended to limit the scope of the present disclosure. The phrase "using 'B' instead of 'A'" used in describing the synthetic examples means that, in terms of molar equivalents, the amount of 'A' used is the same as the amount of 'B' used.

[0547] Example

[0548] Synthetic Example

[0549] Synthetic Example 1: Synthesis of Compound 10

[0550] (1) Synthesis of Compound 10_P-3

[0551] Step 1

[0552]

[0553] 1,3-Dibromo-5-(tert-butyl)benzene (11.12 grams (g), 38.1 millimoles (mmol)), [1,1':3',1”-terphenyl]-2-amine (19.91 g, 81.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (2.20 g, 3.87 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (1.72 g, 4.25 mmol), and sodium tert-butoxide (NaOtBu) (9.17 g, 96.6 mmol) were added to a 1,000 mL three-necked round-bottom flask equipped with a magnetic stir bar. The flask was evacuated and backfilled with nitrogen three times, and toluene (380 milliliters (mL)) was added to the flask and stirred at 110 °C for 7 hours. Then, the reaction was terminated by adding water thereto. The mixture was extracted three times with dichloromethane, and the resulting organic layer was washed with brine, dried over MgSO4, then filtered and concentrated. The resulting crude product was purified by MPLC (gradient of hexane / dichloromethane (MC) from 8% to 45% by weight) to obtain a light gray solid, namely, Compound 10_P-3 (24.23 g, 38.7 mmol, >99% yield). As a result of liquid chromatography mass spectrometry (LCMS) analysis, the purity of Compound 10_P-3 was confirmed to be 98.93%. MS (ESI): 621 [M+H] + .

[0554] (2) Synthesis of Compound 10_P-2

[0555]

[0556] Add N 1 , N 3 -bis([1,1':3',1”-terphenyl]-2-yl)-5-(tert-butyl)benzene-1,3-diamine (Compound 10_P-3, 13.24 g, 20.9 mmol), 1-bromo-3-iodo-2-methylbenzene (44 mL, 312 mmol), CuI (15.9 g, 83.4 mmol), tetraethyl orthosilicate (TEOS, 9.3 mL, 41.7 mmol) and Cs2CO3 (27.2 g, 83.4 mmol) to a 250 mL round-bottomed three-necked flask equipped with a magnetic stir bar. The cycle of evacuating the flask and backfilling it with nitrogen was repeated three times, and tert-butylbenzene (40 mL) was added to the flask and stirred at 170 °C for 24 h. Then, the reaction mixture was filtered directly through a silica gel pad. The brown crude product obtained by evaporating the volatile substances to dryness was purified by MPLC (hexane / MC 5% to 35%) to obtain Compound 10_P-2 (10.35 g, 10.8 mmol, 52% yield) and the monoarylated product (9.50 g). As a result of LCMS analysis, the purity of Compound 10_P-2 was confirmed to be 98.63%. MS (ESI): 959 [M+H] + .

[0557] (3) Synthesis of Compound 10_P-1

[0558] Step 3

[0559]

[0560] Add N 1 , N 3 -3-bis([1,1':3',1”-terphenyl]-2-yl)-N 1 , N 3-Bis(3-bromo-2-methylphenyl)-5-(tert-butyl)benzene-1,3-diamine (Compound 10_P-2, 1.98 g, 2.07 mmol) was added to a test tube equipped with a magnetic stir bar, and the test tube was placed in a glove bag. The cycle of evacuating the glove bag and backfilling with nitrogen was repeated three times, and boron triiodide (3.24 g, 8.28 mmol) was added thereto under a nitrogen atmosphere. After removing the test tube from the glove bag, o-dichlorobenzene (DCB) (10 mL) was added to the test tube, and the reaction mixture was stirred at 170 °C for 24 hours. Then, the reaction was terminated by adding saturated aqueous Na2S2O3 solution (sat. Na2S2O3 aq.) and saturated aqueous NaHCO3 solution (sat. NaHCO3 aq.). The mixture was extracted three times using dichloromethane, and the resulting organic layer was washed with brine, dried over MgSO4, then filtered and concentrated. The obtained crude product was purified by MPLC (hexane / dichloromethane 5% to 25%) to obtain an orange solid, i.e., Compound 10_P-1 (0.90 g, about 0.74 mmol, about 36% yield). As a result of LCMS analysis, the purity of Compound 10_P-1 was confirmed to be about 80% (a mixture of about 1:4 conformational isomers). MS (ESI): 967 [M+H] + 。

[0561] (4) Synthesis of Compound 10

[0562]

[0563] 5,9-bis([1,1':3',1"-terphenyl]-2-yl)-3,11-dibromo-7-(tert-butyl)-4,10-dimethyl-5,9-dihydro-5,9-diaza-13b-borazinnaphtho[3,2,1-de]anthracene (Compound 10_P-1, 0.75 g, 0.78 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.68 g, 3.89 mmol), Pd2(dba)3 (0.21 g, 0.23 mmol) and lithium bis(trimethylsilyl)amide (LHMDS) (0.39 g, 2.34 mmol) were added to a flask with a magnetic stir bar. The flask was evacuated and refluxed with nitrogen. The cycle of filling was repeated three times, and tri-tert-butylphosphine (TTBP) (50% by weight in toluene, 0.20 mL, 0.51 mmol) and xylene (8.0 mL) were added thereto. After stirring at 140 ° C for 18 hours, the reaction mixture was directly filtered through a diatomaceous earth pad. The brown crude product was obtained by evaporating the volatile substances. The crude product was purified by MPLC (hexane / dichloromethane gradient of 5% to 35% by volume) to obtain an orange solid, i.e., compound 10 (0.03 g, 0.026 mmol, 3% yield). As a result of LCMS analysis, it was confirmed that the purity of compound 10 exceeded 80% (mixture of conformers). MS (ESI): 1155 [M+H] + .

[0564] The synthesis methods of the compounds of the present application (including Compound 1) other than Compound 10 can be easily recognized by those skilled in the art by referring to the aforementioned synthesis routes and starting materials.

[0565] Evaluation Example 1: Evaluation of Photoluminescence Quantum Yield (PLQY)

[0566] A solution of poly(methyl methacrylate) (PMMA) in CH2Cl2, 5 wt% of 4,4-dicarbazolyl-1,1'-biphenyl (CBP) and compound 1 were mixed and the resulting product was applied to a quartz substrate by spin coating using a spin coater. The substrate was heat treated in an oven at 80°C and then cooled to room temperature to produce a film.

[0567] To evaluate the PLQY in the film, the PLQY of compound 1 was evaluated using a Hamamatsu Photonics absolute PL quantum yield measurement system (Hamamatsu Photonics, Ltd., Shizuoka, Japan) equipped with a xenon lamp light source, a monochromator, a photon multichannel analyzer, and an integrating sphere and using PLQY measurement software, and this was repeated for compounds 10, B, and C. The evaluation results are shown in Table 2.

[0568] Table 2

[0569]

[0570]

[0571] Referring to Table 2, it is confirmed that the heterocyclic compound represented by Formula 1 according to one or more embodiments is suitable for emitting blue light and has excellent PLQY. In addition, it is confirmed that the heterocyclic compound represented by Formula 1 according to one or more embodiments has excellent properties based on high PLQY compared to the comparative compound.

[0572] Example 1

[0573] The ITO glass substrate was cut into a size of 50 mm × 50 mm × 0.5 mm, ultrasonically treated with acetone, isopropyl alcohol, and pure water for 15 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The obtained glass substrate was loaded onto a vacuum deposition apparatus.

[0574] Subsequently, HAT-CN was deposited on the ITO electrode (anode) of the glass substrate to form a hole injection layer having a thickness of, NPB was deposited on the hole injection layer to form a first hole transport layer having a thickness of, TCTA was deposited on the first hole transport layer to form a second hole transport layer having a thickness of, and mCP was deposited on the second hole transport layer to form an electron blocking layer having a thickness of.

[0575] The first host (H25), the second host (H26), the sensitizer (PT1), and the emitter (Compound 10) were co-deposited on the electron blocking layer to form an emission layer having a thickness of. Here, the first host and the second host were mixed at a weight ratio of 65:35, and the amounts of the sensitizer and the emitter were adjusted to 13 wt% and 1.2 wt%, respectively, based on the total weight of the first host, the second host, the sensitizer, and the emitter.

[0576] DBFPO was deposited on the emission layer to form a hole blocking layer having a thickness of, DBFPO and LiQ were co-deposited at a weight ratio of 5:5 to form an electron transport layer having a thickness of, LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of, and Al was deposited on the electron injection layer to form a cathode having a thickness of, thus completing the fabrication of the organic light-emitting device.

[0577]

[0578] Example 2 and Comparative Examples 1 and 2

[0579] An organic light-emitting device was fabricated in a similar manner to that in Example 1, except that when forming the emission layer, the compounds shown in Table 3 were each used as an emitter.

[0580] For the organic light-emitting devices of Example 1 and 2 and Comparative Examples 1 and 2, the external quantum efficiency (EQE, %) was measured and evaluated by using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). The evaluation results are shown in Table 3.

[0581] Table 3

[0582] Emitters in the emission layer EQE (%) at 1000 nits Example 1 Compound 1 21.9 Example 2 Compound 10 23.2 Comparative Example 1 Compound B 20.5 Comparative Example 2 Compound C 17.4

[0583]

[0584] Referring to Table 3, it was confirmed that the organic light-emitting device according to one or more embodiments has excellent luminous efficiency. In addition, it was confirmed that the organic light-emitting devices of Example 1 and 2 have excellent performance based on a high EQE as compared with the organic light-emitting devices of Comparative Examples 1 and 2.

[0585] According to one or more embodiments, the heterocyclic compound represented by Formula 1 has excellent light-emitting characteristics and excellent charge transfer characteristics, and thus an electronic device including at least one of the heterocyclic compounds represented by Formula 1, such as an organic light-emitting device, can have high efficiency. Therefore, by using at least one of the heterocyclic compounds represented by Formula 1, a high-quality organic light-emitting device can be realized. In addition, by using the heterocyclic compound represented by Formula 1, an electronic device having excellent efficiency can be realized.

[0586] 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.

Claims

1. A heterocyclic compound represented by Formula 1: Formula 1 Formula 2 Formula 3 Among them, In Formulas 1, 2, and 3, X1 is a single bond, O, S, Se, N(Ar2), N(R1), C(R1)(R2), Si(R1)(R2), Ge(R1)(R2), B(R1), P(R1), P(=O)(R1), S(=O)2, or C(=O), Ar1 and Ar2 are each independently a group represented by Formula 2, a substituted or unsubstituted C6-C 60 aryl, a substituted or unsubstituted C1-C 60 heteroaryl, a substituted or unsubstituted C2-C 60 alkyl heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, Ring CY1 to ring CY7 are each independently a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group, Cz1 is a group represented by Formula 3, R 11 is a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, R1, R2, R 10 , R 20 , R 30 , R 40 , and R 50 each independently represents a group represented by Formula 3, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro 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 substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C1-C 60 alkylthio group, 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 C7-C 60 alkylaryl group, a substituted or unsubstituted C7-C 60 arylalkyl 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 C2-C 60 alkylheteroaryl group, a substituted or unsubstituted C2-C 60 heteroarylalkyl group, a substituted or unsubstituted C1-C 60 heteroaryloxy group, a substituted or unsubstituted C1-C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), R 60 and R 70 each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro 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 substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C1-C 60 alkylthio group, 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 C7-C 60 alkylaryl group, a substituted or unsubstituted C7-C 60 arylalkyl 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 C2-C 60 alkylheteroaryl group, a substituted or unsubstituted C2-C 60 heteroarylalkyl group, a substituted or unsubstituted C1-C 60 heteroaryloxy group, a substituted or unsubstituted C1-C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), b10, b20, b30, b40, and b50 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14, b60 and b70 are each independently 1, 2, 3, 4, 5, 6, 7, or 8, R1, R2, R 10 , R 11 , R 20 , R 30 , R 40 , R 50 , R 60 , and R 70 in which at least two adjacent groups are optionally bonded together 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, 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 C7-C 60 alkylaryl, substituted C7-C 60 arylalkyl, substituted C6-C 60 aryloxy, substituted C6-C 60 arylthio, substituted C1-C 60 heteroaryl, substituted C2-C 60 alkylheteroaryl, substituted C2-C 60 heteroarylalkyl, substituted C1-C 60 heteroaryloxy, substituted C1-C 60 The substituents of substituted monovalent non-aromatic fused polycyclic groups, and substituted monovalent non-aromatic fused heteropolycyclic groups are each independently: Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl 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; 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, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, 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, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 11 )(Q 12 )(Q 13 )、-Ge(Q 11 )(Q 12 )(Q 13 )、-C(=O)(Q 11 )、-S(=O)(Q 11 )、-S(=O)2(Q 11 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-P(=O)(Q 11 )(Q 12 )、-P(=S)(Q 11 )(Q 12 )、or a combination thereof; Each of which is 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, C7-C 60 alkylaryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, 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, C7-C 60 alkylaryl, C7-C 60 arylalkyl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, C2-C 60 alkylheteroaryl, C2-C 60 heteroarylalkyl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-C(=O)(Q 21 )、-S(=O)(Q 21 ), -S(=O)2(Q 21 ), -B(Q 21 )(Q 22 ), -P(Q 21 )(Q 22 ), -P(=O)(Q 21 )(Q 22 ), -P(=S)(Q 21 )(Q 22 ), or a combination thereof; -N(Q 31 )(Q 32 )、-Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O)2(Q 31 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-P(=O)(Q 31 )(Q 32 )、or -P(=S)(Q 31 )(Q 32 );or in combination, Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 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 C7-C 60 alkylaryl, a substituted or unsubstituted C7-C 60 arylalkyl, 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 C2-C 60 alkylheteroaryl, a substituted or unsubstituted C2-C 60 heteroarylalkyl, a substituted or unsubstituted C1-C 60 heteroaryloxy, a substituted or unsubstituted C1-C 60 heteroarylthio, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and * represents a binding site to an adjacent atom.

2. The heterocyclic compound according to claim 1, wherein each of Ring CY1 to Ring CY5 is independently a benzene group, a naphthalene group, a phenanthrene group, a fluorene group, a pyridine group, a pyrimidine group, a triazine group, a quinoline group, an isoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a dibenzoborol group, a dibenzophosphol group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, or a dibenzothiophene 5,5-dioxide group.

3. The heterocyclic compound according to claim 1, wherein each of Ring CY6 and Ring CY7 is independently a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, or a quinazoline group.

4. The heterocyclic compound according to claim 1, wherein Ar1 and Ar2 are each independently a group represented by one of Formulas 2-1 to 2-3: Formula 2-1 Formula 2-2 Formula 2-3 Among them, In Formulas 2-1 to 2-3, Ring CY4, Ring CY5, R 40 , R 50 , b40 and b50 are each the same as those described in claim 1, represents a single bond or a double bond, and * represents a binding site to an adjacent atom.

5. The heterocyclic compound according to claim 1, wherein the group represented by Formula 2 is a group represented by one of Formulas 2A to 2C: Formula 2A Formula 2B Formula 2C Among them, In Formulas 2A to 2C, X 41 is C(R 41 ), or N, X 42 is C(R 42 ), or N, X 43 is C(R 43 ), or N, and X 44 is C(R 44 ), or N, X 51 is C(R 51 ), or N, X 52 is C(R 52 ), or N, X 53 is C(R 53 ), or N, X 54 is C(R 54 ), or N, and X 55 is C(R 55 ), or N, R 41 to R 44 Each independently is the same as that described for R in claim 1 40 described, R 51 to R 55 each independently is the same as that described for R in claim 1, and 50 ​ * represents a binding site to an adjacent atom.

6. The heterocyclic compound according to claim 1, wherein the group represented by Formula 3 is a group represented by Formula 3A: Formula 3A Among them, In Formula 3A, X 61 is C(R 61 ), or N, X 62 is C(R 62 ), or N, X 63 is C(R 63 ), or N, and X 64 is C(R 64 ), or N, X 71 is C(R 71 ), or N, X 72 is C(R 72 ), or N, X 73 is C(R 73 ), or N, and X 74 is C(R 74 ), or N, R 61 to R 64 Each independently is the same as that described for R in claim 1 60 as described, R 71 to R 74 each independently is the same as that described for R in claim 1, and 70 ​ * represents a binding site to an adjacent atom.

7. The heterocyclic compound according to claim 1, wherein R1, R2, R 10 、R 20 、R 30 、R 40 、R 50 、R 60 and R 70 are each independently: 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, C1-C 20 alkyl, C1-C 20 alkoxy, or C1-C 20 alkylthio; C1-C each substituted as follows 20 alkyl, C1-C 20 alkoxy, or C1-C 20 alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, -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, deuterated C1-C 20 alkyl, fluorinated C1-C 20 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, 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)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[2.2.1]heptyl, (C1-C 20 alkyl)bicyclo[2.2.2]octyl, silacyclopentyl, phenyl, (C1-C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidinyl, or a combination thereof; Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, silacyclopentyl, phenyl, (C1-C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, 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, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothienyl: deuterium, -F, -Cl, -Br, -I, -SF5, -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, deuterated C1-C 20 alkyl, fluorinated C1-C 20 alkyl, C1-C 20 alkoxy, C1-C 20 alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, 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)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 (C1-C alkyl) bicyclo[2.1.1]hexyl, (C1-C 20 (C1-C alkyl) bicyclo[2.2.1]heptyl, (C1-C 20 (C1-C alkyl) bicyclo[2.2.2]octyl, silacyclopentyl, phenyl, (C1-C 20 (C1-C alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, (C1-C alkyl), pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, 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, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, or a combination thereof; or -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

8. The heterocyclic compound according to claim 1, wherein at least one of R 20 is a group represented by Formula 3.

9. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is represented by Formula 11 or 12: Formula 11 Formula 12 Among them, In Formulas 11 and 12, Ring CY1 to ring CY3, X1, Ar1, Ar2, Cz1, R 10 , R 11 , R 20 , R 30 , b10, b20, and b30 are the same as those in claim 1, Cz2 is the same as that described for Cz1 in claim 1, R 21 is the same as that described for R in claim 1 20 and represents a single bond or a double bond.

10. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is represented by Formula 21 or 22: Formula 21 Formula 22 Among them, In Formulas 21 and 22, Ar1, Ar2, X1 and R 11 each being the same as those in claim 1, X 12 is C(R 12 ), or N, and X 13 is C(R 13 ), or N, X 21 is C(R 21 ), or N, X 22 is C(R 22 ), or N, X 23 is C(R 23 ), or N, and X 24 is C(R 24 ), or N, X 31 is C(R 31 ), or N, X 32 is C(R 32 ), or N, and X 33 is C(R 33 ), or N, X 61 is C(R 61 ), or N, X 62 is C(R 62 ), or N, X 63 is C(R 63 ), or N, X 64 is C(R 64 ), or N, X 65 is C(R 65 ), or N, X 66 is C(R 66 ), or N, X 67 is C(R 67 ), or N, and X 68 is C(R 68 ), or N, X 71 is C(R 71 ), or N, X 72 is C(R 72 ), or N, X 73 is C(R 73 ), or N, X 74 is C(R 74 ), or N, X 75 is C(R 75 ), or N, X 76 is C(R 76 ), or N, X 77 is C(R 77 ), or N, and X 78 is C(R 78 ), or N, R 12 and R 13 each independently is the same as that described for R in claim 1 10 respectively. R 21 to R 24 Each is independently the same as that described for R in claim 1 20 described, R 31 to R 33 Each independently is the same as that described for R in claim 1 30 as described R 61 to R 68 each independently is the same as that described for R in claim 1, and 60 ​ R 71 to R 78 Each independently is the same as that described for R in claim 1 70 as described 11. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is represented by Formula 31 or 32: Formula 31 Formula 32 Among them, In Formulas 31 and 32, Ar1, Ar2, X1 and R 11 each being the same as those in claim 1, R 12 and R 13 each independently is the same as that described for R in claim 1 10 respectively, R 21 to R 24 Each independently is the same as that described for R in claim 1 20 as described, R 31 to R 33 each independently is the same as that described for R in claim 1 30 as described, R 61 to R 68 each independently is the same as that described for R in claim 1, and 60 ​ R 71 to R 78 each independently is the same as that described for R in claim 1 70 as described.

12. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is one of Compounds 1 to 83:

13. An organic light-emitting device, comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes at least one heterocyclic compound according to any one of claims 1 to 12.

14. The organic light-emitting device according to claim 13, wherein the emission layer includes the at least one heterocyclic compound.

15. The organic light-emitting device according to claim 14, wherein the emission layer includes a host and an emitter, and the emitter includes the at least one heterocyclic compound.

16. The organic light-emitting device according to claim 15, wherein, based on weight, the amount of the host in the emission layer is greater than the amount of the heterocyclic compound in the emission layer.

17. The organic light-emitting device according to claim 15, wherein the emission layer further includes a sensitizer.

18. The organic light-emitting device according to claim 17, wherein the sensitizer includes a phosphorescent dopant.

19. The organic light-emitting device according to claim 14, wherein the emission layer emits light having a maximum emission wavelength of 400 nanometers to 490 nanometers.

20. An electronic device, comprising the organic light-emitting device according to any one of claims 13 to 19.

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