Heterocyclic compound and organic light-emitting device including same

Abstract

Disclosed are a heterocyclic compound represented by Formula 1 and an organic light-emitting device including the same. 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), CY1-CY3 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, Ar1 and Ar2 are each independently a group represented by Formula 2, and the remaining groups and variables are as detailed in the specification. Formula 1 # imgabs 0 # and formula 2 # imgabs 1 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application is based on and claims the benefit of priority from Korean Patent Application No. 10-2023-0098941 filed on July 28, 2023 in the Korean Intellectual Property Office, the contents of which are incorporated herein in their entirety by reference. Technical Field

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

[0004] The organic light emitting device is a self-emitting device having improved characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed, and produces a full-color image.

[0005] OLED includes an anode, a cathode, and an organic layer between the anode and the cathode and including an emission layer. A hole transport region may be between the anode and the emission layer, and an electron transport region may be between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. Holes and electrons recombine in the emission layer to generate excitons. Excitons may transition from an excited state to a ground state, thereby generating light. Summary of the invention

[0006] Provided are a heterocyclic compound and an organic light-emitting device including the same.

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

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

[0009] Formula 1

[0010]

[0011] Formula 2

[0012]

[0013] Wherein, in formula 1 and 2,

[0014] X 1 For single bonds, O, S, Se, N (Ar 2 )、N(R 1 )、C(R 1 )(R 2 )、Si(R 1 )(R 2)、Ge(R 1 )(R 2 )、P(R 1 )、P(=O)(R 1 )、S(=O) 2 , or C(=O),

[0015] CY 1 -CY 3 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0016] Ar 1 and Ar 2 are each independently a group represented by Formula 2,

[0017] L 1 is a single bond, substituted or unsubstituted C 5 -C 30 A carbocyclic group, or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0018] a1 is 1, 2, or 3,

[0019] CY 21 -CY 24 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0020] R 1 , R 2 , R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , and R 70 Each independently represents a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-P(=O)(Q 1 )(Q 2 )、-P(=S)(Q 1 )(Q 2 ), or a group represented by formula 3,

[0021] Formula 3

[0022]

[0023] Among them, in formula 3,

[0024] X 31 For single bonds, O, S, N(R 301 ), or C(R 301 )(R 302 ),

[0025] k31 is 0 or 1,

[0026] CY 31 and CY 32 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0027] L 30 is a single bond, substituted or unsubstituted C 5 -C 30 A carbocyclic group, or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0028] a30 is 1, 2, or 3,

[0029] R 301 , R 302 , R 310 , and R 320 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 6 -C60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-P(=O)(Q 1 )(Q 2 ), or -P(=S)(Q 1 )(Q 2 ),

[0030] b310 and b320 are each independently 1, 2, 3, 4, 5, 6, 7, or 8,

[0031] b10, b20, b30, b40, b50, b60, and b70 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14,

[0032] R 1 , R 2 , R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , R 70 , R 301 , R 302 , R 310 , and R 320Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0033] Substituted C 5 -C 30 Carbocyclic groups, substituted C 1 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 2 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Alkyl aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is

[0034] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy,

[0035] Each of C is substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, 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 any combination thereof,

[0036] C each unsubstituted or substituted 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C6 -C 60 Arylthio, C 1 -C 60 heteroaryl, 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 any combination thereof,

[0037] -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(Q 31 )(Q 32 ),or

[0038] Any combination of

[0039] Q 1 -Q 3 , Q 11 -Q 13 , Q 21 -Q23 , and Q 31 -Q 33 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, unsubstituted or substituted with deuterium, C 1 -C 60 Alkyl, C 6 -C 60 Aryl, or any combination thereof substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, unsubstituted or substituted with deuterium, C 1 -C 60 Alkyl, C 6 -C 60 Aryl, or any combination thereof substituted C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group, and

[0040] * indicates the binding site with the adjacent atom.

[0041] According to another aspect of the present disclosure, an organic light emitting device includes the heterocyclic compound. BRIEF DESCRIPTION OF THE DRAWINGS

[0042] The above and other aspects, features, and advantages of some embodiments of the present disclosure will become more apparent from the following description considered in conjunction with the accompanying drawings, in which:

[0043] Figure 1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment; and

[0044] Figures 2 to 6Each is a schematic diagram illustrating energy transfer of an organic light emitting device according to an embodiment. DETAILED DESCRIPTION

[0045] Embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Therefore, embodiments are described below only by reference to the accompanying drawings to illustrate aspects.

[0046] It will be understood that when an element is referred to as being “on” another element, it can be directly on the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.

[0047] It will be understood that although the terms "first", "second", "third", etc. may be used herein to describe various elements, components, regions, layers and / or parts, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or part from another element, component, region, layer or part. Therefore, without departing from the teachings herein, the first element, component, region, layer, or part discussed below may be referred to as a second element, component, region, layer, or part.

[0048] The terms used herein are only used for the purpose of describing specific embodiments and are not intended to be restrictive. As used herein, "a (kind) (indefinite article) (a, an)", "said (the)" and "at least one (kind)" do not represent the limitation of quantity, and are intended to cover both the singular and the plural, unless the context clearly indicates otherwise. For example, "element" has the same meaning as "at least one element", unless the context clearly indicates otherwise. Expressions such as "at least one (kind)" when before or after a list of elements modify the entire list of elements and do not modify the individual elements of the list.

[0049] "Or" means "and / or". As used herein, the term "and / or" includes any and all combinations of one or more of the relevant listed items. It will be further understood that the terms "comprise" or "include" when used in this specification indicate the presence of the stated features, regions, integers, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more additional features, regions, integers, steps, operations, elements, components, and / or their collections.

[0050] In addition, relative terms such as "lower" or "bottom" and "upper" or "top" may be used herein to describe the relationship of one element to another element as shown in the figure. It will be understood that in addition to the orientation depicted in the figure, relative terms are also intended to include different orientations of the device. For example, if the device in one of the figures is turned over, the element described as being on the "lower" side of the other element will be oriented on the "upper" side of the other element. Therefore, depending on the specific orientation of the figure, the exemplary term "lower" can cover both "lower" and "upper" orientations. Similarly, if the device in one of the figures is turned over, the element described as "below" or "below" the other element will be oriented "above" the other element. Therefore, the exemplary terms "below..." or "below..." can cover both "above..." and "below..." orientations.

[0051] As used herein, "about" or "approximately" is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art taking into account the measurement in question and the errors 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, or within ±10% or 5% relative to the stated value.

[0052] 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 the present disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the present disclosure and the relevant art, and will not be interpreted in an idealized or overly formal sense, unless clearly so defined herein.

[0053] Exemplary embodiments are described herein with reference to cross-sectional views as schematic diagrams of idealized embodiments. Thus, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are to be expected. Therefore, the embodiments described herein should not be construed as being limited to the specific shapes of the regions as illustrated herein, but rather include deviations in shape caused by, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. Moreover, the illustrated sharp corners may be rounded. Therefore, the regions shown in the figures are schematic in nature and their shapes are not intended to illustrate the precise shapes of the regions and are not intended to limit the scope of the claims.

[0054] The heterocyclic compound according to an embodiment may be represented by Formula 1:

[0055] Formula 1

[0056]

[0057] In formula 1, X 1 Can be single bond, O, S, Se, N(Ar 2 )、N(R 1 )、C(R 1 )(R 2 )、Si(R 1 )(R 2 )、Ge(R 1 )(R 2 )、B(R 1 )、P(R 1 )、P(=O)(R 1 )、S(=O) 2 , or C(=O).

[0058] In an embodiment, X 1 Can be single bond, O, S, Se, N(Ar 2 )、N(R 1 )、C(R 1 )(R 2 ), or Si(R 1 )(R 2 ).

[0059] In formula 1, CY 1 -CY 3 Can be independently C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.

[0060] In an embodiment, CY 1 -CY 3 may each independently be i) a first ring, ii) a second ring, iii) a fused ring in which at least two first rings are fused, iv) a fused ring in which at least two second rings are fused, or v) a fused ring in which at least one first ring is fused with at least one second ring,

[0061] The first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a thiorrole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzothiorrole 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 isothitriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiorrole group, a diazathiorrole group, or a triazathiorrole group, and

[0062] The second ring may be an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane(norbornane) group, a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0063] In an embodiment, CY 1 -CY 3 Can be independently C 6 -C 30 Aromatic carbocyclic group or C 1 -C 30 Aromatic heterocyclic group.

[0064] In an embodiment, CY 1 -CY 3 can be independently 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, benzothiorrole group, benzoborole group, benzophosphole group, benzoselenophene group, benzogermanol group, dibenzothiophene group, dibenzofuran group, carbazole group, fluorene group, dibenzothiorrole group, dibenzoborole group, dibenzophosphole group, dibenzoselenophene group, dibenzogermanol group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzothiorrole group, azabenzoborole group, azabenzophosphole group , an azabenzoselenophene group, an azabenzogermanol group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborol group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermanol group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.

[0065] In an embodiment, CY 1 -CY 3Each may independently be a benzene group, a naphthyl group, a phenanthrene group, a fluorene group, a spirobifluorene group, a pyridine group, a pyrimidine 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 dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermanol group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, or a dibenzothiophene 5,5-dioxide group.

[0066] In an embodiment, CY 1 and CY 2 Each may be independently a group represented by any one of Formulae 1-1 to 1-9:

[0067]

[0068] Among them, in formulas 1-1 to 1-9,

[0069] R 11 -R 18 and R 11a -R 18a Each independently and with respect to R 10 Same as described,

[0070] X 2 Can be O, S, Se, N (R 3 )、C(R 3 )(R 4 )、Si(R 3 )(R 4 )、Ge(R 3 )(R 4 )、B(R 3 )、P(R 3 )、P(=O)(R 3 )、S(=O) 2 , or C(=O),

[0071] R 3 and R 4 Each independently and with respect to R 1 Same as described, and

[0072] * 1 and* 2 Each represents a binding site with a neighboring atom.

[0073] In an embodiment, * in Formulas 1-1 to 1-9 1 and* 2 Any one of may be a binding site to the B atom in Formula 1.

[0074] For example, * in formulas 1-1 to 1-9 1 It can be a binding site with the B atom in Formula 1.

[0075] In another example, * in Formulas 1-1 to 1-9 2 It can be a binding site with the B atom in Formula 1.

[0076] In formula 2, CY 21 -CY 24 Can be independently C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.

[0077] In an embodiment, CY 21 -CY 24 may each independently be i) a first ring, ii) a second ring, iii) a fused ring in which at least two first rings are fused, iv) a fused ring in which at least two second rings are fused, or v) a fused ring in which at least one first ring is fused with at least one second ring,

[0078] The first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a thiorrole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzothiorrole 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 isothitriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiorrole group, a diazathiorrole group, or a triazathiorrole group, and

[0079] The second ring may be an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane(norbornane) group, a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0080] In an embodiment, CY 21 -CY 24 Can be independently C 6 -C 30 Aromatic carbocyclic group or C 1 -C 30 Aromatic heterocyclic group.

[0081] In an embodiment, CY 21 -CY 24can be independently 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, benzothiorrole group, benzoborole group, benzophosphole group, benzoselenophene group, benzogermanol group, dibenzothiophene group, dibenzofuran group, carbazole group, fluorene group, dibenzothiorrole group, dibenzoborole group, dibenzophosphole group, dibenzoselenophene group, dibenzogermanol group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzothiorrole group, azabenzoborole group, azabenzophosphole group , an azabenzoselenophene group, an azabenzogermanol group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborol group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermanol group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.

[0082] In an embodiment, CY 21 -CY 24 Each may independently be a benzene group, a naphthyl 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.

[0083] In an embodiment, CY 21 -CY 24 Each may be a phenyl group.

[0084] In an embodiment, the group represented by Formula 2 may be a group represented by any one of Formulae 2A to 2D:

[0085]

[0086] Wherein, in Formulas 2A to 2D,

[0087] CY 22 -CY 24 , L 1、a1、R 50 , R 60 , R 70 , b50, b60, and b70 are each the same as described above,

[0088] R 41 -R 44 Each and About R 40 Same as described, and

[0089] *Indicates the binding site with the adjacent atom.

[0090] In an embodiment, the group represented by Formula 2 may be a group represented by any one of Formulae 2-1 to 2-4:

[0091]

[0092] Among them, in formulas 2-1 to 2-4,

[0093] L 1 and a1 are each the same as described above,

[0094] R 41 -R 44 Each and About R 40 Same as described,

[0095] R 51 -R 54 Each and About R 50 Same as described,

[0096] R 61 -R 64 Each and About R 60 Same as described,

[0097] R 71 -R 74 Each and About R 70 Same as described, and

[0098] *Indicates the binding site with the adjacent atom.

[0099] In formula 2, L 1 Can be a single bond, substituted or unsubstituted C 5 -C 30 A carbocyclic group, or a substituted or unsubstituted C 1 -C 30 Heterocyclic group.

[0100] In an embodiment, L 1 may be a single bond, phenylene, naphthylene, phenanthrenyl, fluorenylene, or pyrenylene; or

[0101] Phenylene, naphthylene, phenanthrenyl, fluorenylene, or pyrenylene, each substituted by deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, naphthyl, anthracenyl, or any combination thereof.

[0102] In an embodiment, L 1 Can be a single bond.

[0103] In Formula 2, a1 may be 1, 2, or 3.

[0104] In an embodiment, a1 may be 1.

[0105] In Formula 2, * represents a binding site with an adjacent atom.

[0106] In formulas 1 and 2, R 1 , R 2 , R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , and R 70 Each of them may be independently a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-P(=O)(Q 1 )(Q 2 )、-P(=S)(Q 1 )(Q 2 ), or a group represented by Formula 3:

[0107] Formula 3

[0108]

[0109] In formula 3, X 31 Can be single bond, O, S, N(R 301 ), or C(R 301 )(R 302).

[0110] In Formula 3, k31 can be 0 or 1. When k31 is 0, (X 31 ) 31 Does not exist.

[0111] In formula 3, CY 31 and CY 32 Can be independently C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.

[0112] In an embodiment, CY 31 and CY 32 Each may independently be a benzene group, a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a silole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzosilole group.

[0113] In formula 3, L 30 Can be a single bond, substituted or unsubstituted C 5 -C 30 A carbocyclic group, or a substituted or unsubstituted C 1 -C 30 Heterocyclic group.

[0114] In Formula 3, a30 may be 1, 2, or 3.

[0115] In an embodiment, a30 may be 1.

[0116] In formula 3, R 301 , R 302 , R 310 , and R 320 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-P(=O)(Q 1 )(Q 2 ), or -P(=S)(Q 1 )(Q 2 ).

[0117] In an embodiment, R 301 , R 302 , R 310 , and R 320 Can be independently:

[0118] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF 5 , C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy;

[0119] Each of C is substituted by 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -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 (norbornyl), bicyclo[2.2.2]octyl, (C 1 -C 20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C 1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl, (C1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl)bicyclo[2.2.1]heptyl, (C 1 -C 20 alkyl) bicyclo[2.2.2]octyl, silanol, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidinyl, or any combination thereof;

[0120] 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, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzo Thiphenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, C 1 -C 20alkoxy, 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, (C 1 -C 20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C 1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl)bicyclo[2.2.1]heptyl, (C 1 -C 20 alkyl) bicyclo[2.2.2]octyl, silanol, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, or any combination thereof; or

[0121] -N(Q1 )(Q 2 )、-Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-P(=O)(Q 1 )(Q 2 ), or -P(=S)(Q 1 )(Q 2 ).

[0122] In an embodiment, R 301 , R 302 , R 310 , and R 320 can each independently be hydrogen, deuterium, 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, C 1 -C 20 Alkylphenyl, or naphthyl.

[0123] In Formula 3, b310 and b320 may each independently be 1, 2, 3, 4, 5, 6, 7, or 8.

[0124] In an embodiment, R 1 , R 2 , R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , and R 70 Each of them may be independently: a group represented by Formula 2, a group represented by Formula 3, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino 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, -SF 5 , C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy;

[0125] Each of C is substituted by 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -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 (norbornyl), bicyclo[2.2.2]octyl, (C 1 -C 20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C 1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl)bicyclo[2.2.1]heptyl, (C 1 -C 20 alkyl) bicyclo[2.2.2]octyl, silanol, phenyl, (C 1 -C20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidinyl, or any combination thereof;

[0126] 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, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzo Thiphenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, 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, (C 1 -C 20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl)bicyclo[2.2.1]heptyl, (C 1 -C 20 alkyl) bicyclo[2.2.2]octyl, silanol, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, or any combination thereof; or

[0127] -N(Q 1 )(Q 2 )、-Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-C(=O)(Q 1 )、-S(=O)(Q 1)、-S(=O) 2 (Q 1 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-P(=O)(Q 1 )(Q 2 ), or -P(=S)(Q 1 )(Q 2 ).

[0128] In an embodiment, R 1 , R 2 , R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , and R 70 Can be independently:

[0129] A group represented by Formula 2, a group represented by Formula 3, hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy; or

[0130] A group represented by any one of formulae 9-1 to 9-61, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350:

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141] Wherein, in Formulae 9-1 to 9-61, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350, * represents a bonding site with an adjacent atom, "Ph" represents a phenyl group, "TMS" represents a trimethylsilyl group, and "TMG" represents a trimethylgermyl group.

[0142] In an embodiment, R 1 , R 2 , R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , and R 70 Can be independently:

[0143] A group represented by Formula 2, a group represented by Formula 3, hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy; or

[0144] A group represented by any one of formulae 9-1 to 9-61, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350.

[0145] In an embodiment, R 10 , R 20 , and R 30 At least one of may be a group represented by Formula 3.

[0146] For example, the quantity R is b10 10 At least one R of b2020 At least one, and / or a quantity of b30 R 30 At least one of may be a group represented by Formula 3.

[0147] In an embodiment, the number of R is b10 10 At least one of may be a group represented by Formula 3.

[0148] In an embodiment, the number of R is b20 20 At least one of may be a group represented by Formula 3.

[0149] In an embodiment, the number of R is b30 30 At least one of may be a group represented by Formula 3.

[0150] In Formulae 1 and 2, b10, b20, b30, b40, b50, b60, and b70 may each independently be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14.

[0151] In an embodiment, the group represented by Formula 3 may be a group represented by any one of Formulae 3-1 to 3-3:

[0152]

[0153] Among them, in formulas 3-1 to 3-3,

[0154] L 30 and a30 are each the same as described in the specification,

[0155] X 301 About X 31 Same as described,

[0156] X 311 Can be C(R 311 ) or N, X 312 Can be C(R 312 ) or N, X 313 Can be C(R 313 ) or N, X 314 Can be C(R 314 ) or N, X 315 Can be C(R 315 ) or N,

[0157] X 321 Can be C(R 321 ) or N, X 322 Can be C(R 322 ) or N, X 323 Can be C(R 323 ) or N, X 324 Can be C(R 324) or N, X 325 Can be C(R 325 ) or N,

[0158] R 311 -R 315 Each independently and with respect to R 310 Same as described,

[0159] R 321 -R 325 Each independently and with respect to R 320 Same as described, and

[0160] *Indicates the binding site with the adjacent atom.

[0161] In formulas 1 and 2, R 1 , R 2 , R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , R 70 , R 301 , R 302 , R 310 , and R 320 Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic group.

[0162] In an embodiment, the heterocyclic compound may be represented by Formula 11-1 or 11-2:

[0163] Formula 11-1

[0164]

[0165] Formula 11-2

[0166]

[0167] Among them, in formulas 11-1 and 11-2,

[0168] CY 1 CY 2 ,Ar 1 ,Ar 2 , R 10 , R 20 , b10, and b20 are each the same as described above,

[0169] X 11Can be single bond, O, S, Se, N(R 1 )、C(R 1 )(R 2 )、Si(R 1 )(R 2 )、Ge(R 1 )(R 2 )、B(R 1 )、P(R 1 )、P(=O)(R 1 )、S(=O) 2 , or C(=O), R 1 and R 2 each being the same as described above, and

[0170] R 31 -R 33 Each independently and with respect to R 30 Same as described.

[0171] In an embodiment, in Formulas 11-1 and 11-2, R 31 -R 33 At least one of may be a group represented by Formula 3. For example, R 32 The group may be a group represented by Formula 3.

[0172] In an embodiment, the heterocyclic compound may have a symmetrical structure or an asymmetrical structure.

[0173] For example, the heterocyclic compound may have a symmetrical structure.

[0174] In another example, the heterocyclic compound may have an asymmetric structure.

[0175] In the specification, the substituted C 5 -C 30 Carbocyclic groups, substituted C 1 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 2 -C 10Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Alkyl aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

[0176] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy;

[0177] Each of C is substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, 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 any combination thereof;

[0178] C each unsubstituted or substituted 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, 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 any combination thereof;

[0179] -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(Q 31 )(Q 32 );or

[0180] Any combination thereof.

[0181] The Q 1 -Q 3 , Q 11 -Q 13 , Q 21 -Q 23 , and Q 31 -Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphoric acid group or its salt; unsubstituted or substituted with deuterium, C 1 -C 60 Alkyl, C 6 -C 60 Aryl, or any combination thereof substituted C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; C 3 -C 10 Cycloalkyl; C 1 -C 10 Heterocycloalkyl; C 3 -C 10 Cycloalkenyl; C 2 -C 10 Heterocycloalkenyl; unsubstituted or substituted with deuterium, C1 -C 60 Alkyl, C 6 -C 60 Aryl, or any combination thereof substituted C 6 -C 60 Aryl; C 6 -C 60 Aryloxy; C 6 -C 60 Arylthio; C 1 -C 60 heteroaryl; a monovalent non-aromatic fused polycyclic group; or a monovalent non-aromatic fused heteropolycyclic group.

[0182] For example, the Q 1 -Q 3 , Q 11 -Q 13 , Q 21 -Q 23 , and Q 31 -Q 33 Can be independently:

[0183] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;or

[0184] n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl, each unsubstituted or substituted with: deuterium, C 1 -C 10 Alkyl, phenyl, or any combination thereof.

[0185] In an embodiment, the heterocyclic compound may be at least one of compounds 1 to 360, but embodiments of the present disclosure are not limited thereto:

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216] The heterocyclic compound represented by Formula 1 may satisfy the structure of Formula 1 described above and include a structure in which an N atom of Formula 1 is substituted with a group represented by Formula 2. Due to such a structure, the heterocyclic compound represented by Formula 1 may have excellent light emitting characteristics, and in particular, may realize a deep blue color with a short wavelength.

[0217] Although not limited to a particular theory, it is believed that since the heterocyclic compound satisfies the structure described above and thus has a high oscillator strength (f), when the heterocyclic compound is applied to an electronic device, its efficiency can be improved. In addition, by including a substituent with a bulky structure represented by Formula 2 as described above, the heterocyclic compound can have a high S 1 Energy level and photo-directional (photo-orientation) characteristics. Therefore, when the heterocyclic compound is used as a light-emitting material, Dexter energy transfer can be suppressed, which leads to excellent life characteristics.

[0218] Therefore, an electronic device including the heterocyclic compound represented by Formula 1, for example, an organic light emitting device, may have high efficiency and a long lifespan.

[0219] The highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, S 1 Energy level, T 1 The energy level and oscillator strength (f) are shown in Table 1.

[0220] Table 1

[0221]

[0222]

[0223] As shown in Table 1, the heterocyclic compound represented by Formula 1 has electrical characteristics suitable for use in electronic devices, for example, as a dopant (eg, an emitter or a sensitizer) of an organic light-emitting device.

[0224] In an embodiment, the emission spectrum of the heterocyclic compound or the emission peak of the electroluminescence spectrum may have a half width (FWHM) of 60 nanometers (nm) or less. For example, the emission spectrum of the heterocyclic compound or the emission peak of the electroluminescence spectrum may have a FWHM of about 5 nm to about 50 nm, about 7 nm to about 40 nm, or about 10 nm to about 30 nm.

[0225] The synthesis method of the heterocyclic compound represented by Formula 1 can be recognized by those skilled in the art with reference to the following synthesis examples.

[0226] There is no particular limitation on the method of confirming the structure of the heterocyclic compound represented by Formula 1. In an embodiment, the structure of the heterocyclic compound may be confirmed by a known method such as nuclear magnetic resonance spectroscopy (NMR), liquid chromatography-mass spectrometry (LC-MS), and the like.

[0227] Organic light-emitting devices

[0228] According to another aspect of the present disclosure, an organic light emitting device includes the heterocyclic compound.

[0229] An organic light emitting device according to an embodiment may include: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, and

[0230] The organic layer may include a heterocyclic compound represented by Formula 1.

[0231] In one or more embodiments, the emission layer may include the heterocyclic compound.

[0232] In an embodiment, the emission layer may include a host and an emitter, and the emitter may include the heterocyclic compound.

[0233] In an embodiment, the amount of the host in the emission layer may be greater than that of the heterocyclic compound based on weight.

[0234] In an embodiment, the emission layer may further include a sensitizer.

[0235] In embodiments, the sensitizer may include a phosphorescent compound, a delayed fluorescent compound, or any combination thereof.

[0236] The detailed description of the emitter is the same as provided above, and the detailed description of the host and the sensitizer is the same as provided below.

[0237] By including the emission layer including the heterocyclic compound represented by Formula 1, the organic light emitting device may have a relatively narrow EL spectrum emission peak FWHM and excellent efficiency and lifespan characteristics.

[0238] In an embodiment, the heterocyclic compound may be used as a dopant (e.g., an emitter or a sensitizer) in the emission layer, and the emission layer may further include a host (i.e., in the emission layer, the amount of the heterocyclic compound represented by Formula 1 may be less than the amount of the host).

[0239] In an embodiment, the emission layer may emit blue light. For example, the emission layer may emit blue light having a maximum emission wavelength in a range of about 400 nm to about 490 nm, for example, about 410 nm to about 490 nm.

[0240] As used herein, the expression “(the emission layer) includes at least one heterocyclic compound represented by Formula 1” may include the case where “(the emission layer) includes the same heterocyclic compound represented by Formula 1” and the case where “(the emission layer) includes two or more different heterocyclic compounds represented by Formula 1”.

[0241] For example, the emission layer may include only Compound 1 as the heterocyclic compound. In this regard, Compound 1 may be present in the emission layer of the organic light-emitting device. In some embodiments, the emission layer may include Compounds 1 and 2 as the heterocyclic compound.

[0242] Figure 1 Description

[0243] Figure 1 FIG. 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. Figure 1 A structure and a method of manufacturing an organic light emitting device according to an embodiment are described.

[0244] Figure 1 The organic light emitting device 10 may include 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 .

[0245] The organic layer 15 may include an emission layer, and may further include a hole transport region disposed between the first electrode 11 and the emission layer, and an electron transport region disposed between the emission layer and the second electrode 19 .

[0246] A substrate may be additionally provided under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in an organic light-emitting device, for example, a glass substrate or a transparent plastic substrate, each of which has excellent mechanical strength, thermal stability, transparency, surface smoothness, easy handling (processing), and waterproofness.

[0247] The first electrode 11

[0248] The first electrode 11 may be manufactured by depositing or sputtering a material for forming the first electrode 11 onto the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials having a high work function to facilitate hole injection.

[0249] The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 11 is a transmissive electrode, the material used to form the first electrode 11 may be selected from indium tin oxide ("ITO"), indium zinc oxide ("IZO"), tin oxide (SnO 2 ), zinc oxide (ZnO), and any combination thereof, but the embodiment is not limited thereto. In some embodiments, when the first electrode 11 is a semi-transmissive electrode or a reflective electrode, as a material for forming the first electrode 11, at least one of the following can be used: magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiment is not limited thereto.

[0250] The first electrode 11 may have a single-layer structure or a multi-layer structure including a plurality of layers.

[0251] Emission Layer

[0252] The emission layer may include the heterocyclic compound.

[0253] The thickness of the emission layer may be about to about For example 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 driving voltage.

[0254] Figure 2 Description

[0255] In an embodiment, the heterocyclic compound may be a fluorescent emitter.

[0256] According to an embodiment, the emission layer may further include a host (hereinafter, referred to as "host A", and host A may be different from the heterocyclic compound). Host A can be understood by referring to the description of the host material provided herein, but the embodiment is not limited thereto. Host A may be a fluorescent host.

[0257] refer to Figure 2 , describing energy transfer according to an embodiment.

[0258] Singlet excitons can be generated by the host A in the emission layer, and the singlet excitons generated by the host A can be Energy transfer (or Resonance Energy Transfer (FRET)) is transferred to the fluorescent emitter.

[0259] The ratio of singlet excitons generated by the host A may be 25%, and therefore, 75% of triplet excitons generated by the host A may fuse with each other to be converted into singlet excitons. Therefore, the efficiency of the organic light-emitting device may be further improved. That is, by utilizing the triplet-triplet fusion (TTF) mechanism, the efficiency of the organic light-emitting device may be further improved.

[0260] According to an embodiment, the ratio of the emission component emitted from the heterocyclic compound to the total emission component emitted from the emission layer may be 80% or more, for example 90% or more. In some embodiments, the ratio of the emission component emitted from the heterocyclic compound to the total emission component emitted from the emission layer may be 95% or more.

[0261] The heterocyclic compound may emit fluorescence, and the host may not emit light.

[0262] In an embodiment, when the emission layer further includes a host A in addition to the heterocyclic compound, the amount of the heterocyclic compound may be 50 parts by weight or less, for example, 30 parts by weight or less, based on 100 parts by weight of the emission layer, and the amount of the host A in the emission layer may be 50 parts by weight or more, for example, 70 parts by weight or more, based on 100 parts by weight of the emission layer, but the embodiment is not limited thereto.

[0263] In an embodiment, when the emission layer further includes a host A in addition to the heterocyclic compound, the host A and the heterocyclic compound may satisfy Condition A:

[0264] Condition A

[0265] E(H A ) S1 >E S1

[0266] Among them, in condition A,

[0267] E(H A ) S1 represents the lowest excited singlet energy level of host A, and

[0268] E S1 represents the lowest excited singlet energy level of the heterocyclic compound.

[0269] Here, E(H A ) S1 and E S1The evaluation can be performed by using the Gaussian program according to a density functional theory (DFT) method in which the structure optimization is performed at the level of B3LYP / 6-31G (d, p) .

[0270] for Figure 3 Description

[0271] In an embodiment, the heterocyclic compound may be a delayed fluorescence emitter.

[0272] According to an embodiment, the emission layer may further include a host (hereinafter, referred to as "host B", and host B may be different from the heterocyclic compound). Host B may be understood by referring to the description of the host material provided herein, but embodiments are not limited thereto.

[0273] refer to Figure 3 , describing energy transfer according to an embodiment.

[0274] 25% of the singlet excitons generated by the host B in the emission layer can be transferred to the delayed fluorescence emitter by FRET. In addition, 75% of the triplet excitons generated by the host B in the emission layer can be transferred to the delayed fluorescence emitter by Dexter energy transfer. At least some of the singlet energy of the fluorescent emitter can be transferred to the triplet state by intersystem crossing (ISC). The energy transferred to the triplet state of the delayed fluorescence emitter can undergo reverse intersystem crossing (RISC). Therefore, by transferring all singlet excitons and triplet excitons generated in the emission layer to the heterocyclic compound, an organic light-emitting device with improved efficiency can be obtained.

[0275] Therefore, in an embodiment, the ratio of the emission component emitted from the heterocyclic compound to the total emission component emitted from the emission layer may be 80% or more, such as 90% or more. In some embodiments, the ratio of the emission component emitted from the heterocyclic compound to the total emission component emitted from the emission layer may be 95% or more.

[0276] Here, the heterocyclic compound may emit fluorescence and / or delayed fluorescence, and the emission component of the heterocyclic compound may be the sum of the instantaneous emission component of the heterocyclic compound and the delayed fluorescence component of the heterocyclic compound through RISC. In addition, the host B may not emit light.

[0277] In an embodiment, when the emission layer further includes a host B in addition to the heterocyclic compound, the amount of the heterocyclic compound may be 50 parts by weight or less, for example, 30 parts by weight or less, based on 100 parts by weight of the emission layer, and the amount of the host B in the emission layer may be 50 parts by weight or more, for example, 70 parts by weight or more, based on 100 parts by weight of the emission layer, but the embodiment is not limited thereto.

[0278] In an embodiment, when the emission layer further includes a host B in addition to the heterocyclic compound, the host B and the heterocyclic compound may satisfy Condition B:

[0279] Condition B

[0280] E(H B ) S1 >E S1

[0281] Among them, in condition B,

[0282] E(H B ) S1 represents the lowest excited singlet energy level of host B, and

[0283] E S1 represents the lowest excited singlet energy level of the heterocyclic compound.

[0284] Here, E(H B ) S1 and E S1 The evaluation can be performed by using the Gaussian program according to a density functional theory (DFT) method in which the structure optimization is performed at the level of B3LYP / 6-31G (d, p) .

[0285] Figure 4 Description

[0286] In an embodiment, the heterocyclic compound may be used as a fluorescent emitter, and the emission layer may further include a sensitizer, such as a delayed fluorescence sensitizer. In an embodiment, the emission layer may further include a host (hereinafter referred to as "host C", and host C may be different from the heterocyclic compound and the sensitizer) and a sensitizer (hereinafter referred to as "sensitizer A", and sensitizer A may be different from host C and the heterocyclic compound). Host C and sensitizer A can be understood by referring to the description of the host material and sensitizer material provided herein, respectively, but embodiments are not limited thereto.

[0287] In an embodiment, the ratio of the emission component of the heterocyclic compound relative to the total emission component emitted from the emission layer may be about 80% or more, for example 90% or more (or for example, 95% or more). For example, the heterocyclic compound may emit fluorescence. In addition, the host C and the sensitizer A may each not emit light.

[0288] refer to Figure 4 , describing energy transfer according to an embodiment.

[0289] Singlet and triplet excitons can be generated by the host C in the emission layer, and the singlet and triplet excitons generated by the host C can be transferred to the sensitizer A and then transferred to the heterocyclic compound through FRET. 25% of the singlet excitons generated by the host C can be transferred to the sensitizer A through FRET, and 75% of the triplet excitons generated by the host C can be transferred to the singlet and triplet states of the sensitizer A. At least some of the singlet energy of the sensitizer A can be transferred to the triplet state through intersystem crossing (ISC). The energy transferred to the triplet state of the sensitizer A can be transferred to the singlet state through reverse intersystem crossing (RISC), and then the singlet energy of the sensitizer A can be transferred to the heterocyclic compound through FRET.

[0290] Therefore, by transferring all singlet excitons and triplet excitons generated in the emission layer to the dopant (e.g., emitter), an organic light-emitting device with improved efficiency can be obtained. In addition, since an organic light-emitting device with significantly reduced energy loss can be obtained, the life characteristics of the organic light-emitting device can be improved.

[0291] refer to Figure 4 , when the emission layer further includes a host C and a sensitizer A in addition to the heterocyclic compound, the host C, the sensitizer A and the heterocyclic compound may satisfy conditions C-1 and / or C-2:

[0292] Condition C-1

[0293] S 1 (H C )≥S 1 (S A )

[0294] Condition C-2

[0295] S 1 (S A )≥S 1 (HC)

[0296] Among them, in conditions C-1 and C-2,

[0297] S 1 (H C) represents the lowest excited singlet energy level of the host C,

[0298] S 1 (S A ) represents the lowest excited singlet energy level of sensitizer A, and

[0299] S 1 (HC) represents the lowest excited singlet energy level of the heterocyclic compound.

[0300] S can be evaluated using the Gaussian program according to the DFT method. 1 (H C ), S 1 (S A ), and S 1 (HC), where the structure was optimized at the B3LYP / 6-31G(d,p) level.

[0301] When the host C, the sensitizer A, and the heterocyclic compound satisfy Condition C-1 and / or C-2, FRET from the sensitizer A to the heterocyclic compound may be promoted, and thus, the organic light-emitting device may have improved luminous efficiency.

[0302] Figure 5 Description

[0303] In an embodiment, the heterocyclic compound may be used as a fluorescent emitter, and the emission layer may further include a sensitizer such as a phosphorescent sensitizer.

[0304] In an embodiment, the emission layer may further include a host (hereinafter, referred to as "host D", and the host D may be different from the heterocyclic compound and the sensitizer) and a sensitizer (hereinafter, referred to as "sensitizer B", and the sensitizer B may be different from the host D and the heterocyclic compound). The host D and the sensitizer B may be understood by referring to the description of the host material and the sensitizer material provided herein, respectively, but the embodiment is not limited thereto.

[0305] In an embodiment, the ratio of the emission component of the heterocyclic compound relative to the total emission component emitted from the emission layer may be about 80% or more, for example 90% or more (or for example, 95% or more). For example, the heterocyclic compound may emit fluorescence. In addition, the host D and the sensitizer B may each not emit light.

[0306] refer to Figure 5 , describing energy transfer according to an embodiment.

[0307] 75% of triplet excitons generated by the host D in the emission layer may be transferred to the sensitizer B by Dexter energy transfer, and 25% of the energy of singlet excitons generated by the host D may be transferred to the singlet and triplet states of the sensitizer B. The energy transferred to the singlet state of the sensitizer B may undergo ISC to be transferred to the triplet state, and then, the triplet energy of the sensitizer B may be transferred to the heterocyclic compound by FRET.

[0308] Therefore, by transferring all singlet excitons and triplet excitons generated in the emission layer to the dopant (e.g., emitter), an organic light-emitting device with improved efficiency can be obtained. In addition, since an organic light-emitting device with significantly reduced energy loss can be obtained, the life characteristics of the organic light-emitting device can be improved.

[0309] In an embodiment, when the emission layer further includes a host D and a sensitizer B in addition to the heterocyclic compound, the host D, the sensitizer B and the heterocyclic compound may satisfy conditions D-1 and / or D-2:

[0310] Condition D-1

[0311] T 1 (H D )≥T 1 (S B )

[0312] Condition D-2

[0313] T 1 (S B )≥S 1 (HC)

[0314] Among them, in conditions D-1 and D-2,

[0315] T 1 (H D ) represents the lowest excited triplet energy level of the host D,

[0316] T 1 (S B ) represents the lowest excited triplet energy level of sensitizer B, and

[0317] S 1 (HC) represents the lowest excited singlet energy level of the heterocyclic compound.

[0318] T can be evaluated using the Gaussian program according to the DFT method. 1 (H D ), T 1 (S B ), and S 1(HC), where the structure was optimized at the B3LYP / 6-31G(d,p) level.

[0319] When the host D, the sensitizer B, and the heterocyclic compound satisfy Condition D-1 and / or D-2, FRET from the sensitizer B to the heterocyclic compound may be promoted, and thus, the organic light-emitting device may have improved luminous efficiency.

[0320] In an embodiment, the amount of the sensitizer in the emission layer may be in a range of about 5 weight percent (wt%) to about 50 wt%, or for example, about 10 wt% to about 30 wt%. When the content is within this range, energy transfer in the emission layer may occur efficiently. Therefore, the organic light emitting device may have high efficiency and long life.

[0321] In an embodiment, an amount of the heterocyclic compound in the emission layer may be in a range of about 0.01 wt % to about 15 wt %, or for example, about 0.05 wt % to about 3 wt %, but embodiments are not limited thereto.

[0322] In an embodiment, the heterocyclic compound may further satisfy condition 5:

[0323] Condition 5

[0324] 0 microseconds (μs) <T 衰减 (HC)<5μs

[0325] Among them, in condition 5,

[0326] T 衰减 (HC) represents the decay time of the heterocyclic compound.

[0327] The decay time of the heterocyclic compound was measured by time-resolved photoluminescence (TRPL) spectroscopy at room temperature of a film having a thickness of 40 nm (hereinafter, referred to as "film (HC)") formed as follows: -7 The host and the heterocyclic compound included in the emission layer were vacuum deposited on a quartz substrate at a weight ratio of 90:10 at a vacuum pressure of 200 torr.

[0328] Figure 6 Description

[0329] In an embodiment, the heterocyclic compound may be used as a delayed fluorescence emitter, and the emission layer may further include a sensitizer, for example, a delayed fluorescence sensitizer.

[0330] In an embodiment, the emission layer may further include a host (hereinafter, referred to as "host E", and the host E may be different from the heterocyclic compound and the sensitizer) and a sensitizer (hereinafter, referred to as "sensitizer C", and the sensitizer C may be different from the host E and the heterocyclic compound). The host E and the sensitizer C can be understood by referring to the description of the host material and the sensitizer material provided herein, respectively, but the embodiment is not limited thereto.

[0331] In an embodiment, the ratio of the emission component of the heterocyclic compound relative to the total emission component emitted from the emission layer may be about 80% or more, for example 90% or more (or for example, 95% or more). In some embodiments, the heterocyclic compound may emit fluorescence and / or delayed fluorescence. In addition, the host E and the sensitizer C may each not emit light.

[0332] Here, the heterocyclic compound may emit fluorescence and / or delayed fluorescence, and the emission component of the heterocyclic compound may be the sum of an instantaneous emission component of the heterocyclic compound and a delayed fluorescence component of the heterocyclic compound through RISC.

[0333] refer to Figure 6 , describing energy transfer according to an embodiment.

[0334] 25% of the singlet excitons generated by the host E in the emission layer can be transferred to the singlet state of the sensitizer C by FRET, and the energy of 75% of the triplet excitons generated by the host E can be transferred to the triplet state of the sensitizer C, and then the singlet energy of the sensitizer C can be transferred to the heterocyclic compound by FRET. Subsequently, the triplet energy of the sensitizer C can be transferred to the heterocyclic compound by Dexter energy transfer. The energy transferred to the triplet state of the sensitizer C can undergo RISC to be transferred to the singlet state. In addition, in the case of the sensitizer C, the triplet energy generated by the sensitizer C can be reversely transferred to the host E (i.e., triplet exciton distribution (TED)), and then transferred to the heterocyclic compound by RISC to emit light.

[0335] Therefore, by transferring all singlet excitons and triplet excitons generated in the emission layer to the dopant (e.g., emitter), an organic light-emitting device with improved efficiency can be obtained. In addition, since an organic light-emitting device with significantly reduced energy loss can be obtained, the life characteristics of the organic light-emitting device can be improved.

[0336] In an embodiment, when the emission layer further includes a host E and a sensitizer C in addition to the heterocyclic compound, the host E, the sensitizer C, and the heterocyclic compound may satisfy conditions E-1, E-2, and / or E-3:

[0337] Condition E-1

[0338] S 1 (H E )≥S 1 (S C )

[0339] Condition E-2

[0340] S 1 (S C )≥S 1 (HC)

[0341] Condition E-3

[0342] T 1 (S C )≥T 1 (HC)

[0343] Among them, in conditions E-1, E-2, and E-3,

[0344] S 1 (H E ) represents the lowest excited singlet energy level of the host E,

[0345] S 1 (S C ) represents the lowest excited singlet energy level of sensitizer C,

[0346] S 1 (HC) represents the lowest excited singlet energy level of the heterocyclic compound,

[0347] T 1 (S C ) represents the lowest excited triplet energy level of sensitizer C, and

[0348] T 1 (HC) represents the lowest excited triplet energy level of the heterocyclic compound.

[0349] S can be evaluated using the Gaussian program according to the DFT method. 1 (H E ), S 1 (S C ), S 1 (HC), T 1 (S C ), and T 1 (HC), where the structure was optimized at the B3LYP / 6-31G(d,p) level.

[0350] When the host E, the sensitizer C, and the heterocyclic compound satisfy conditions E-1, E-2, and / or E-3, Dexter energy transfer and FRET from the sensitizer C to the heterocyclic compound can be promoted, and thus, the organic light-emitting device can have improved luminous efficiency.

[0351] In an embodiment, the amount of the sensitizer C in the emission layer may be in the range of about 5 wt % to about 50 wt %, or for example, about 10 wt % to about 30 wt %. When the content is within this range, energy transfer in the emission layer may occur efficiently. Therefore, the organic light emitting device may have high efficiency and long life.

[0352] In an embodiment, an amount of the heterocyclic compound in the emission layer may be in a range of about 0.01 wt % to about 15 wt %, or for example, about 0.05 wt % to about 3 wt %, but embodiments are not limited thereto.

[0353] Subject in the emission layer

[0354] In an embodiment, the host may not include metal atoms.

[0355] In an embodiment, the main body may include at least one compound selected from the following: a compound containing fluorene, a compound containing carbazole, a compound containing dibenzofuran, a compound containing dibenzothiophene, a compound containing indenylcarbazole, a compound containing indolecarbazole, a compound containing benzofurancarbazole, a compound containing benzothiophenecarbazole, a compound containing acridine, a compound containing dihydroacridine, a compound containing triindoleacene, a compound containing pyridine, a compound containing pyrimidine, a compound containing triazine, a compound containing silicon, a cyano group, a phosphine oxide-containing compound, a sulfoxide-containing compound, and a sulfonyl group-containing compound.

[0356] 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.

[0357] In an embodiment, the host may consist of one kind of host. When the host consists of one kind of host, the one kind of host may be selected from a bipolar host, an electron transport host, and a hole transport host, which will be described later.

[0358] In an embodiment, the host may include a mixture of two or more different hosts. For example, the host may be a mixture of an electron transport host and a hole transport host, a mixture of two different types of electron transport hosts, or a mixture of two different types of hole transport hosts. The electron transport host and the hole transport host can be understood by referring to the relevant description to be presented later.

[0359] In an embodiment, 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.

[0360] The electron transport moiety used herein may be selected from a cyano group, a cyclic group containing π-electron-deficient nitrogen, and a group represented by one of the following formulae:

[0361]

[0362] Wherein, in the formula part, *, *', and *" may each represent a binding site with an adjacent atom.

[0363] In an embodiment, the electron transport host of the emission layer may include at least one of a cyano group and a cyclic group containing π-electron-deficient nitrogen.

[0364] In an embodiment, the electron transport host in the emission layer may include at least one cyano group.

[0365] In an embodiment, the electron transport host in the emission layer may include at least one cyano group and at least one cyclic group including π-electron-deficient nitrogen.

[0366] In an embodiment, the host may include an electron transport host and a hole transport host, wherein the electron transport host may include at least one cyclic group that does not contain π-electron-deficient nitrogen and at least one electron transport portion, and the hole transport host may include at least one cyclic group that does not contain π-electron-deficient nitrogen and may not include an electron transport portion.

[0367] The term "cyclic group containing π-electron-deficient nitrogen" as used herein refers to a cyclic group having at least one *-N=*' portion, and for example, can be selected from 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, and an azacarbazole group; and a condensed ring group in which two or more of the aforementioned cyclic groups containing π-electron-deficient nitrogen are fused to each other.

[0368] At the same time, the cyclic group not containing π-electron-deficient nitrogen can be selected from a phenyl group, a heptadene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthene group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthene group, a phenanthene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, Group, tetraphenyl group, The invention also includes but is not limited to a fused ring group of two or more of the foregoing cyclic groups not containing π-electron-deficient nitrogen, a perylene group, a pentacene group, a hexacenyl group, a pentaphene group, a rubine group, a coronene group, an ovalenyl group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a triindolephenyl group, and a fused ring group of two or more of the foregoing cyclic groups not containing π-electron-deficient nitrogen, but the embodiments of the present disclosure are not limited thereto.

[0369] In an embodiment, when the host is a mixture of an electron transport host and a hole transport host, the weight ratio of the electron transport host to the hole transport host may be 1:9 to 9:1, for example, 2:8 to 8:2, for example, 4:6 to 6:4, for example, 5: 5. When the weight ratio of the electron transport host to the hole transport host satisfies the above-described range, a hole-and-electron transport balance in the emission layer may be achieved.

[0370] The host may include at least one selected from TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, compound H50, and compound H51:

[0371]

[0372] In one or more embodiments, the host may further include a compound represented by Formula 301:

[0373] Formula 301

[0374]

[0375] Ar in Formula 301 111 and Ar 112 Can be independently selected from:

[0376] phenylene, naphthylene, phenanthrenyl, and pyrenylene; and

[0377] Phenylene, naphthylene, phenanthrenylene, and pyrenylene groups each being substituted by at least one selected from the group consisting of phenyl, naphthyl, and anthracenyl.

[0378] Ar in Formula 301 113 -Ar 116 Can be independently selected from:

[0379] C 1 -C 10 alkyl, phenyl, naphthyl, phenanthrenyl, and pyrenyl; and

[0380] Phenyl, naphthyl, phenanthrenyl, and pyrenyl, each of which is substituted by at least one selected from the group consisting of phenyl, naphthyl, and anthracenyl.

[0381] In Formula 301, g, h, i, and j may each independently be an integer of 0-4, and may be 0, 1, or 2, for example.

[0382] Ar in Formula 301 113 -Ar 116 Can be independently selected from:

[0383] C substituted by at least one selected from phenyl, naphthyl, and anthracenyl 1 -C 10 alkyl;

[0384] phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, and fluorenyl;

[0385] phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, and fluorenyl, each of which is selected from at least one substituted group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, and fluorenyl; and

[0386]

[0387] However, the implementation of the present disclosure is not limited thereto.

[0388] In one or more embodiments, the host may include a compound represented by the following formula 302:

[0389] Formula 302

[0390]

[0391] Ar in formula 302 122 -Ar 125With respect to Ar in Formula 301 113 Same as described in detail.

[0392] Ar in formula 302 126 and Ar 127 Can be independently C 1 -C 10 Alkyl (eg, methyl, ethyl, or propyl).

[0393] In formula 302, k and l may each independently be an integer of 0 to 4. For example, k and l may be 0, 1, or 2.

[0394] In an embodiment, the host may include at least one of compounds H1 to H26:

[0395]

[0396]

[0397] In an embodiment, the host may be composed of one type of compound. For example, the one type of compound may be selected from a first material (hole transport host) and a second material (electron transport host).

[0398] In an embodiment, the host may include at least two kinds of compounds. For example, the host may include at least two different kinds of hole transport hosts, at least two different kinds of electron transport hosts, or a combination of at least one kind of hole transport host and at least one kind of electron transport host.

[0399] Emitters in the Emission Layer

[0400] The emitter may include the heterocyclic compound.

[0401] Sensitizer in the emissive layer

[0402] In embodiments, the sensitizer may include a phosphorescent compound.

[0403] In an embodiment, the phosphorescent compound may include an organic metal compound including at least one kind of metal.

[0404] In an embodiment, the organometallic compound may include at least one metal selected from transition metals (M 11 ) and organic ligands (L 11 ), and L 11 and M 11 One, two, three, or four cyclometallated rings may be formed.

[0405] In an embodiment, the organometallic compound may be represented by Formula 101:

[0406] Formula 101

[0407] M 11 (L 11 ) n11 (L 12 ) n12

[0408] Wherein, in Formula 101,

[0409] M 11 It can be a transition metal,

[0410] L 11 may be a ligand represented by any one of formulae 111-1 to 111-4,

[0411] L 12 It can be a monodentate ligand or a bidentate ligand,

[0412] n11 is 1,

[0413] n12 can be selected from 0, 1, and 2,

[0414]

[0415] Among them, in formulas 111-1 to 111-4,

[0416] A1-A4 can be independently selected from substituted or unsubstituted C 5 -C 30 Carbocyclic group, substituted or unsubstituted C 1 -C 30 Heterocyclic groups, and non-cyclic groups,

[0417] Y 11 -Y 14 Can be independently a chemical bond, O, S, N (R 91 )、B(R 91 )、P(R 91 ), or C(R 91 )(R 92 ),

[0418] T 1 -T 4 can be independently selected from 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)-*', and *-C≡C-*',

[0419] Substituted C 5 -C 30 Substituents of carbocyclic groups, substituted C 1 -C 30 The substituent of the heterocyclic group, and R 91 -R 94 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, 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, -Si(Q 1 )(Q2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-C(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ), and -P(=S)(Q 1 )(Q 2 ), wherein the substituted C 5 -C 30 Substituents of carbocyclic groups and substituted C 1 -C 30 The substituent of the heterocyclic group is not hydrogen,

[0420] * 1 ,* 2 ,* 3 ,and* 4 Each indicates that 11 The binding site, and

[0421] Q 1 -Q 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio, monovalent aromatic fused polycyclic group, monovalent aromatic fused heteropolycyclic group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 60 Alkyl, and C 6 -C 60 At least one substituted C 1 -C 60 Alkyl, and is selected from deuterium, -F, cyano, C 1 -C 60 Alkyl, and C 6 -C 60 At least one substituted C 6 -C 60 Aryl.

[0422] In an embodiment, the transition metal may be 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).

[0423] In embodiments, the sensitizer may include a delayed fluorescence compound.

[0424] In an embodiment, the delayed fluorescence compound may be represented by Formula 101 or 102:

[0425]

[0426] Wherein, in equations 101 and 102,

[0427] A 21 Can be an acceptor group,

[0428] D 21 Can be a donor group,

[0429] m21 may be 1, 2, or 3, and n21 may be 1, 2, or 3,

[0430] 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,

[0431] R 201 Can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, SF 5 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-C(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ), and -P(=S)(Q 1 )(Q 2 ), and multiple R 201 may be optionally bonded to each other to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups, and

[0432] Q 1 -Q 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60heteroarylthio, monovalent aromatic fused polycyclic group, monovalent aromatic fused heteropolycyclic group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 60 Alkyl, and C 6 -C 60 At least one substituted C 1 -C 60 Alkyl, and is selected from deuterium, -F, cyano, C 1 -C 60 Alkyl, and C 6 -C 60 At least one substituted C 6 -C 60 Aryl.

[0433] In an embodiment, A in Formulas 101 and 102 21 It may be a substituted or unsubstituted cyclic group that does not contain π-electron-deficient nitrogen.

[0434] In an embodiment, the cyclic group not containing π-electron-deficient nitrogen can be selected from a phenyl group, a heptadene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthene group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthene group, a phenanthene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, Group, tetraphenyl group, The invention relates to a cyclopentadiene group, a perylene group, a pentacene group, a hexaphenyl group, a pentylphene group, a rubine 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 indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a triindolephenyl group; and a condensed ring group of two or more of the foregoing cyclic groups not containing π-electron-deficient nitrogen, but the embodiments of the present disclosure are not limited thereto.

[0435] In an embodiment, in Formulas 101 and 102, D 21 Can be selected from: -F, cyano, and cyclic groups containing π-electron-deficient nitrogen;

[0436] C each substituted with at least one selected from -F and cyano 1 -C 60 an alkyl group, a cyclic group containing a π-electron-deficient nitrogen, and a cyclic group not containing a π-electron-deficient nitrogen; and

[0437] A cyclic group containing a π-electron-deficient nitrogen substituted by at least one selected from the group consisting of deuterium, C 1 -C 60 An alkyl group, a cyclic group containing a π-electron-deficient nitrogen, and a cyclic group not containing a π-electron-deficient nitrogen.

[0438] In an embodiment, the cyclic group not containing π-electron-deficient nitrogen is the same as described above.

[0439] The term "cyclic group containing π-electron-deficient nitrogen" as used herein refers to a cyclic group having at least one *-N=*' portion, and for example, can be selected from 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, and a benzimidazole-benzimidazole group; and a condensed ring group in which two or more of the aforementioned cyclic groups containing π-electron-deficient nitrogen are fused to each other.

[0440] In an embodiment, the amount of the sensitizer in the organic layer may be greater than the amount of the emitter. For example, the volume ratio between the sensitizer and the emitter may be 30:0.1 to 10:3 or 10:0.1 to 20:5. The weight ratio between the sensitizer and the emitter may be 10:0.1 to 20:5. The volume ratio between the host and the sensitizer in the organic layer may be 60:40 to 95:5 or 70:30 to 90:10. Alternatively, the weight ratio between the host and the sensitizer may be selected from the range of 60:40 to 95:5. By satisfying the aforementioned content range, the organic light-emitting device may have improved luminous efficiency and / or life characteristics.

[0441] Figure 1 FIG. 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. Figure 1 The structure and manufacturing method of the organic light emitting device 10 according to an embodiment of the present disclosure are described. The organic light emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.

[0442] A substrate may be additionally provided under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in an organic light-emitting device, for example, a glass substrate or a transparent plastic substrate, each of which has excellent mechanical strength, thermal stability, transparency, surface smoothness, easy handling (processing), and waterproofness.

[0443] The first electrode 11 can be manufactured by depositing or sputtering a material for forming the first electrode 11 onto the 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 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 (SnO 2 ), or zinc oxide (ZnO). In one or more embodiments, the material used to form the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0444] The first electrode 11 may have a single-layer structure or a multi-layer structure including a plurality of layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 11 is not limited thereto.

[0445] The organic layer 15 is located on the first electrode 11 .

[0446] The organic layer 15 may include an emission layer, and may further include a hole transport region and an electron transport region.

[0447] The hole transport region may be between the first electrode 11 and the emission layer.

[0448] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0449] The hole transport region may include only a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / electron blocking layer structure, or a first hole injection layer / second hole injection layer / hole transport layer / electron blocking layer structure, wherein for each structure, the corresponding layers are sequentially stacked in the order stated starting from the first electrode 11.

[0450] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, casting, and / or Langmuir-Blodgett (LB) deposition.

[0451] When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature in the range of about 100° C. to about 500° C., a ... -8 To about 10 -3 The vacuum pressure in the range of torr, and about to about However, the deposition conditions are not limited thereto.

[0452] When the hole injection layer is formed by spin coating, the coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the coating conditions may include a coating speed in the range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and a heat treatment temperature in the range of about 80° C. to about 200° C. for removing the solvent after coating. However, the coating conditions are not limited thereto.

[0453] Conditions for forming the hole transport layer and the electron blocking layer may be the same as conditions for forming the hole injection layer.

[0454] The hole transport region may include at least one selected from the group consisting of m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(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 the following Formula 201, and a compound represented by the following Formula 202:

[0455]

[0456] Formula 201

[0457]

[0458] Formula 202

[0459]

[0460] Ar in Formula 201 101 and Ar 102 Can be independently:

[0461] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthenylene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyren ... phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene phenylene, tetraphenylene, perylene, perylene, or pentphenylene; or

[0462] each substituted with at least one of the following: phenylene, pentalene, indenylene, naphthylene, azulenylene, heptalene, acenaphthene, fluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, acenaphthene, fluor ... phenanthrenylene, phenanthrenylene, phen a phenylene group, a tetraphenylene group, a perylene group, a perylene group, or a pentphenylene group: a deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino 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 C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof.

[0463] Xa and xb in Formula 201 may each independently be an integer of 0 to 5, or 0, 1, or 2. For example, Xa may be 1 and Xb may be 0, but Xa and Xb are not limited thereto.

[0464] R in formula 201 and 202 101 -R 108 , R 111 -R 119 and R 121 -R 124 Can be independently:

[0465] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, or hexyl), or C 1 -C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, or pentoxy);

[0466] Each of C is substituted by 1 -C 10 Alkyl or C 1 -C 10 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, or a combination thereof;

[0467] Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl; or

[0468] phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl, each substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, or a combination thereof, but the embodiments of the present disclosure are not limited thereto.

[0469] R in Formula 201 109 Can be:

[0470] phenyl, naphthyl, anthracenyl, or pyridyl; or

[0471] phenyl, naphthyl, anthracenyl, or pyridyl, each substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, naphthyl, anthracenyl, pyridyl, or any combination thereof.

[0472] According to an embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A, but embodiments of the present disclosure are not limited thereto:

[0473] Formula 201A

[0474]

[0475] R in Formula 201A 101 , R 111 , R 112 , and R 109 Each is the same as described in the specification.

[0476] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include compounds HT1 to HT20 shown below, but are not limited thereto:

[0477]

[0478]

[0479]

[0480] The thickness of the hole transport region may be about to about For example 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 to about and the thickness of the hole transport layer may be in the range of about to about For example 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 may be obtained without a significant increase in driving voltage.

[0481] In addition to these materials, the hole transport region may further include a charge generating material for improving the conductive property. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0482] The charge generating material may be, for example, a p-dopant. The p-dopant may be one selected from a quinone derivative, a metal oxide, and a compound containing a cyano group, but the embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are 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; and compounds containing a cyano group such as compounds HT-D1 or F12, but are not limited thereto:

[0483]

[0484] The hole transport region may include a buffer layer.

[0485] Furthermore, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of the formed organic light emitting device may be improved.

[0486] Meanwhile, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be selected from the materials for the hole transport region described above and the materials for the host described above. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be mCP, which will be described later.

[0487] Then, an 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, deposition or coating conditions may be similar to those applied when forming the hole injection layer, although deposition or coating conditions may vary depending on the material used to form the emission layer.

[0488] 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 a blue emission layer. In one or more embodiments, the emission layer may emit white light due to a stacked structure including a red emission layer, a green emission layer, and / or a blue emission layer.

[0489] When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.

[0490] The thickness of the emission layer may be about to about For example 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 driving voltage.

[0491] An electron transport region may be located on the emission layer.

[0492] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0493] 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, and the structure of the electron transport region is not limited thereto. The electron transport layer may have a multilayer structure or a single layer structure including two or more different materials.

[0494] 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.

[0495] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAlq, but embodiments of the present disclosure are not limited thereto:

[0496]

[0497] The thickness of the hole blocking layer may be about to about For example to about When the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics may be obtained without a significant increase in driving voltage.

[0498] The electron transport layer may include BCP, Bphen, Alq 3 , BAlq, TAZ, and NTAZ:

[0499]

[0500] In one or more embodiments, the electron transport layer may include at least one of ET1 to ET25, but is not limited thereto:

[0501]

[0502]

[0503]

[0504] The thickness of the electron transport layer may be about to about For example to about When the thickness of the electron transport layer is within the above-described range, the electron transport layer may have satisfactory electron transport characteristics without a significant increase in driving voltage.

[0505] The electron transport layer may further include a material containing a metal in addition to the materials described above.

[0506] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (8-hydroxyquinoline lithium, LiQ) or ET-D2:

[0507]

[0508] The electron transport region may include an electron injection layer that facilitates the flow of electrons from the second electrode 19 thereinto.

[0509] The electron injection layer may include LiF, NaCl, CsF, Li 2 O, BaO, or any combination thereof.

[0510] The thickness of the electron injection layer may be about to about and for example about to about When the thickness of the electron injection layer is within the above-described range, satisfactory electron injection characteristics may be obtained without a significant increase in driving voltage.

[0511] The second electrode 19 is located on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a metal, an alloy, a conductive compound, or a combination thereof having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as a material for forming the second electrode 19. In one or more embodiments, in order to manufacture a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0512] In the above, reference has been made to Figure 1 An organic light emitting device is described, but embodiments of the present disclosure are not limited thereto.

[0513] According to another aspect of the present disclosure, an electronic device includes the organic light emitting device.

[0514] In addition to the organic light-emitting device described above, 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 any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the organic light-emitting device.

[0515] According to another aspect of the present disclosure, a diagnostic composition includes a heterocyclic compound represented by Formula 1.

[0516] The diagnostic composition may include at least one heterocyclic compound represented by Formula 1.

[0517] Since the heterocyclic compound represented by Formula 1 provides high luminescence efficiency, a diagnostic composition including the heterocyclic compound may have high diagnostic efficiency.

[0518] The diagnostic compositions can be used in a variety of applications including diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0519] As used herein, the term "C 1 -C 60 "Alkyl" refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 Alkyl is a divalent group of the same structure.

[0520] C 1 -C 60 Alkyl, C 1 -C 20 Alkyl, and / or C 1 -C 10 Examples of alkyl are 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: 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 any combination thereof. For example, Formula 9-33 is a branched C 6 Alkyl, for example, tert-butyl substituted with two methyl groups.

[0521] The term "C 1 -C 60 "Alkoxy" refers to a 101 (A 101 C 1 -C 60The invention further comprises a monovalent group represented by an alkyl group, and examples thereof include a methoxy group, an ethoxy group, and an isopropoxy group.

[0522] C 1 -C 60 Alkoxy, C 1 -C 20 Alkoxy or C 1 -C 10 Examples of the alkoxy group are methoxy, ethoxy, propoxy, butoxy, and pentoxy.

[0523] As used herein, the term "C 2 -C 60 "Alkenyl" refers to a group consisting of 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon double bond in the middle or at the terminal of an alkyl group, and examples thereof include ethenyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0524] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon triple bond in the middle or at the terminal of an alkyl group, and examples thereof include ethynyl and propynyl. 2 -C 60 "Alkyne" refers to a group having a C 2 -C 60 Alkynyl is a divalent group of the same structure.

[0525] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms as ring atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms as ring atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. 3 -C 10 "Cycloalkylene" refers to a cycloalkylene having a 3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0526] As used herein, the term "C 3 -C 10The term "cycloalkyl" may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, and the like.

[0527] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl" as used herein refers to a monovalent saturated cyclic group having at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom and 1 to 10 carbon atoms as ring-forming atoms, and examples thereof include tetrahydrofuranyl and tetrahydrothienyl. 1 -C 10 "Heterocycloalkylene" refers to a 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0528] C 1 -C 10 Examples of heterocycloalkyl groups are silacyclopentyl, silacyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, and tetrahydrothienyl.

[0529] As used herein, the term "C 3 -C 10 The term "cycloalkenyl" as used herein refers to a monovalent cyclic group having 3 to 10 carbon atoms as ring atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0530] As used herein, the term "C 2 -C 10 The term "heterocycloalkenyl" refers to a monovalent cyclic group having at least one heteroatom selected from N, O, P, Si, and S as a ring atom, 2 to 10 carbon atoms as ring atoms, and at least one carbon-carbon double bond in its ring structure and having no aromaticity. 2 -C 10 Examples of heterocycloalkenyl are 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. 2 -C 10 "Heterocycloalkenylene" refers to a 2 -C 10 The term "C" as used herein refers to a divalent group having the same structure as a heterocycloalkenyl group. 2 -C10 "Heterocycloalkenylene" refers to a 2 -C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0531] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.

[0532] As used herein, the term "C 7 -C 60 "Alkylaryl" refers to a 1 -C 54 Alkyl substituted C 6 -C 59 Aryl.

[0533] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group having a cyclic aromatic system having at least one heteroatom selected from N, O, P, Si, and S as a ring atom, and 1 to 60 carbon atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having an aromatic system having at least one heteroatom selected from N, O, P, Si, and S as a ring atom, and 1 to 60 carbon atoms. 1 -C 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, and isoquinolyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.

[0534] As used herein, the term "C 2 -C 60 "Alkylheteroaryl" refers to a1 -C 59 Alkyl substituted C 1 -C 59 Heteroaryl.

[0535] As used herein, the term "C 6 -C 60 "Aryloxy" means -OA 102 (A 102 C 6 -C 60 aryl), and as used herein, the term "C 6 -C 60 "Arylthio" means -SA 103 (A 103 C 6 -C 60 aryl).

[0536] As used herein, the term "C 1 -C 60 "Heteroaryloxy" means -OA 104 (A 104 C 1 -C 60 Heteroaryl), and as used herein, the term "C 1 -C 60 "Heteroarylthio" means -SA 105 (A 105 C 1 -C 60 heteroaryl).

[0537] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8-60 carbon atoms) having two or more rings fused to each other, having only carbon atoms as ring-forming atoms, and not having aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic fused polycyclic group include fluorenyl. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group described above.

[0538] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings fused to each other, having heteroatoms selected from N, O, P, Si, and S as ring-forming atoms in addition to carbon atoms, and having no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic fused heteropolycyclic group include carbazolyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group described above.

[0539] As used herein, the term "C 5 -C 30 The term "carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring atoms. 5 -C 30 The carbocyclic group may be a monocyclic group or a polycyclic group. As used herein, "(unsubstituted or replaced by at least one R 1a Replaced)C 5 -C 30 Examples of the "carbocyclic group" may include (each unsubstituted or substituted by at least one R 1a adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane(norbornane) group, a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, a cyclohexene group, a phenyl group, an indene group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, and a fluorene group.

[0540] As used herein, the term "C 1 -C 30 The term "heterocyclic group" refers to a saturated or unsaturated cyclic group having, in addition to 1 to 30 carbon atoms, at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom. 1 -C 30 The heterocyclic group may be a monocyclic group or a polycyclic group. As used herein, "(unsubstituted or replaced by at least one R 1a Replaced)C 1 -C 30 Examples of the "heterocyclic group" may include (each unsubstituted or substituted by at least one R 1asubstituted) thiophene group, furan group, pyrrole group, thiol group, borolide group, phospholide group, selenophene group, germanol group, benzothiophene group, benzofuran group, indole group, thiol group, benzothiol group, benzoborol group, benzophospholide group, benzoselenophene group, benzogermanol group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzothiol group, dibenzoborol group, a pentadiene group, a dibenzophosphoside group, a dibenzoselenophene group, a dibenzogermanoside group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzothiorrole group, an azabenzoborole group, an azabenzophosphoside group, an azabenzoselenophene group, an azabenzogermanoside group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzothiorrole group, an azabenzoborole group, an azabenzophosphoside group, an azabenzoselenophene group, an azabenzogermanoside group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzoselenophene group, azadibenzogermanol group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, The invention also includes but is not limited to: an oxazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group.

[0541] In the specification, TMS represents *-Si(CH 3 ) 3 , and TMG represents *-Ge(CH 3 ) 3 In addition, the term “(C 1 -C 20 alkyl)X group" (e.g., (C 1 -C 20 Alkyl)phenyl) refers to a 1 -C 20 Alkyl substituted X groups (eg, phenyl).

[0542] Substituted C 5 -C 30 Carbocyclic groups, substituted C 1 -C 30Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 2 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Alkyl aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

[0543] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy;

[0544] Each of C is substituted by 1 -C60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed 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 )(Q12 ), or any combination thereof;

[0545] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;

[0546] Each of C is substituted by 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed 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 any combination thereof; or

[0547] -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 (Q31 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-P(=O)(Q 31 )(Q 32 ), or -P(Q 31 )(Q 32 ),and

[0548] Q 11 -Q 13 , Q 21 -Q 23 , and Q 31 -Q 33 Each of them may be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0549] Hereinafter, the compound and the organic light-emitting device according to the embodiment are described in detail with reference to the synthesis examples and the examples. However, the organic light-emitting device is not limited thereto. The phrase "using 'B' instead of 'A'" used in describing the synthesis examples means that the amount of 'A' used is the same as the amount of 'B' used on a molar equivalent basis.

[0550] Synthesis Example

[0551] Synthesis Example 1: Synthesis of Compound 355

[0552]

[0553] (1) Synthesis of Compound 355_P-1

[0554] Step 1

[0555]

[0556] N-(3-(9H-carbazol-9-yl)phenyl)-9,9'-spirobi[fluorene]-2-amine [5.56 g, 9.71 mmol], N-(5-(9H-carbazol-9-yl)-2,3-dichlorophenyl)-N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine (9.11 g, 14.42 mmol), Pd 2 (dba) 3 To the flask of 250 milliliters (mL) 3 neck round bottom flask with magnetic stirring bar, add 4-nitropropene (0.20g, 0.22mmol), SPhos (0.21g, 0.51mmol) and NaOtBu (1.27g, 13.22mmol).After evacuating the flask and being filled with nitrogen three times, toluene (120mL) is added thereto, then stirred at 110 ℃ for 14 hours.Then the reaction mixture is directly filtered through silica gel pad.The brown crude product obtained by evaporation and drying volatile matter is purified by medium pressure liquid chromatography (MPLC) (hexane / dichloromethane 10% to 45%, by volume) to provide compound 355_P-1 (11.41g, 9.77mmol, yield:>99%) as white solid.Analyzed by LCMS, purity is 93.34%, and MS (ESI): 1167[M+H] + .

[0557] (2) Synthesis of compound 355

[0558] Step 2

[0559]

[0560] N 1-(9,9'-spirobi[fluorene]-2-yl)-N 1 -(3-(9H-carbazol-9-yl)phenyl)-N 3 ,N 3 -bis([1,1'-biphenyl]-4-yl)-5-(9H-carbazole-9-yl)-2-chlorobenzene-1,3-diamine (compound 355_P-1, 9.20 g, 7.88 mmol) was added to a 250 mL 3-neck round bottom flask with a magnetic stirrer. After the flask was evacuated and filled with nitrogen three times, tert-butylbenzene (tBu-Ph, 110 mL) was added thereto, and the mixture was cooled to -78 ° C in a dry ice-hexane container. Tert-butyl lithium (1.47 M in pentane, 13 mL, 19.7 mmol) was added to the reactant at -78 ° C, followed by stirring at 60 ° C for 30 minutes. The reaction mixture was cooled to -78 ° C again, and boron tribromide (1.90 mL, 19.72 mmol) was added thereto. After the mixture was stirred at room temperature for 1 hour, the reaction mixture was cooled to 0°C, and then N,N-diisopropylethylamine (DIPEA, 6.90 mL, 41.75 mmol) was added thereto. After stirring at 110°C for 4 hours, the reactant was diluted with dichloromethane and filtered to obtain a crude solid. The crude solid was purified by using CH 2 Cl 2 / MeOH was repeatedly recrystallized to provide compound 355 (0.79 g, 0.69 mmol, yield: 8.8%) as a light yellow solid. The purity was 99.08% by LCMS analysis, and MS (ESI): 1140 [M+H] + .

[0561] Synthesis Example 2: Synthesis of Compound 356

[0562]

[0563] (1) Synthesis of Compound 356_P-2

[0564] Step 1

[0565]

[0566] N-(3-(9H-carbazol-9-yl)phenyl)-9,9'-spirobi[fluorene]-2-amine (9.70 g, 16.94 mmol), 9-(3,4,5-trichlorophenyl)-9H-carbazole (11.74 g, 33.87 mmol), Pd 2 (dba) 2To a 1,000 mL 3-necked round bottom flask with a magnetic stirrer was added to 1.06 mmol), tri-tert-butylphosphine (ttbp, 50% by weight in toluene, 0.69 g, 1.71 mmol), and NaOtBu (1.95 g, 20.3 mmol). The flask was evacuated and filled with nitrogen three times, and toluene (240 mL) was added thereto. After stirring at 90 ° C for 5 hours, the reaction mixture was directly filtered through a silica gel pad. The brown crude product obtained by evaporation and drying of volatile substances was analyzed by MPLC (hexane / CH 2 Cl 2 10% to 40% by volume) to provide compound 356_P-2 (8.40 g, 9.51 mmol, yield: 56%) as a white solid. The purity was 98.7% by LCMS analysis, and MS (ESI): 881 [M].

[0567] (2) Synthesis of Compound 356_P-1

[0568] Step 2

[0569]

[0570] N-(5-(9H-carbazol-9-yl)-2,3-dichlorophenyl)-N-(3-(9H-carbazol-9-yl)phenyl)-9,9'-spirobi[fluorene]-2-amine (compound 356_P-2, 4.37 g, 4.95 mmol), 9-([1,1'-biphenyl]-3-yl)-N-([1,1'-biphenyl]-4-yl)-9H-carbazol-4-amine (2.19 g, 4.50 mmol), Pd 2 (dba) 2 The 250mL 3-necked round-bottomed flask with magnetic stirring bar was added with ttbp (0.26g, 0.28mmol), ttbp (50% by weight in toluene, 0.18g, 0.45mmol) and NaOtBu (0.52g, 5.40mmol). After the flask was evacuated and filled with nitrogen three times, toluene (45mL) was added thereto, then stirred for 9 hours at 110 ℃. The reaction mixture was then directly filtered through a silica gel pad. The brown crude product obtained by evaporation and drying of volatile substances was analyzed by MPLC (hexane / CH 2 Cl 2 The remaining starting material was acetylated (acetyl chloride, pyridine, in dichloromethane for 18 hours at room temperature) and subjected to a secondary MPLC process (hexane / CH 2Cl 2 37%, by volume) to provide compound 356_P-1 (5.30 g, 3.97 mmol, yield: 88%). The purity was 98.5% by LCMS analysis, and MS (ESI): 1332 [M+H] + .

[0571] (3) Synthesis of Compound 356

[0572]

[0573] N 1 -(9,9'-spirobi[fluorene]-2-yl)-N 1 -(3-(9H-carbazol-9-yl)phenyl)-N 3 ,N 3 -bis([1,1'-biphenyl]-4-yl)-5-(9H-carbazole-9-yl)-2-chlorobenzene-1,3-diamine (compound 356_P-1, 5.00 g, 3.75 mmol) was added to a 250 mL 3-neck round bottom flask with a magnetic stirrer. After the flask was evacuated and filled with nitrogen three times, tert-butylbenzene (125 mL) was added and cooled to -78 ° C in a dry ice / hexane bath. Tert-butyl lithium (1.47 M in pentane, 5.1 mL, 7.50 mmol) was added to the reaction mixture at -78 ° C, followed by stirring at 60 ° C for 1.5 hours. The reaction mixture was cooled to -78 ° C again, and boron tribromide (1.45 mL, 15.05 mmol) was added thereto. After the mixture was stirred at 30 ° C for 1 hour, the reaction mixture was cooled to -78 ° C, and N, N-diisopropylethylamine (2.00 mL, 12.10 mmol) was added thereto. After stirring at 150 ° C for 18 hours, the reaction mixture was diluted with dichloromethane and filtered to obtain a crude solid. The crude solid was analyzed by MPLC (hexane / CH 2 Cl 2 40% by volume) and then purified by CH 2 Cl 2 / MeOH recrystallization to provide compound 356 (0.44 g, 0.34 mmol, 9.0%) as a light yellow solid. The purity was 99.51% by LCMS analysis, and MS (ESI): 1306 [M+H] + .

[0574] Example

[0575] Example 1

[0576] The ITO glass substrate was cut into a size of 50 millimeters (mm)×50 mm×0.5 mm, and then, sonicated in acetone, isopropyl alcohol, and pure water for 15 minutes each, and then, cleaned by exposure to ultraviolet (UV) ozone for 30 minutes.

[0577] Then, in a vacuum deposition device, HAT-CN was deposited on the ITO electrode (anode) on the glass substrate to form a A hole injection layer having a thickness of A first hole transport layer having a thickness of and depositing mCP on the second hole transport layer to form a second hole transport layer having a thickness of The thickness of the electron blocking layer is .

[0578] A first host (H25), a second host (H26), a sensitizer (PT1), and an emitter (compound 355) are co-deposited on the electron blocking layer to form a At this time, the first host and the second host are mixed in a ratio of 65:35, and the amounts of the sensitizer and the emitter are 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.

[0579] Next, DBFPO is deposited on the emission layer to form a A hole blocking layer having a thickness of , DBFPO and LiQ are co-deposited on the hole blocking layer at a weight ratio of 5:5 to form a An electron transport layer having a thickness of Then, a layer having a thickness of Al with a thickness of 1000 nm is used to form a cathode, thereby completing the manufacture of an organic light-emitting device.

[0580]

[0581] Example 2 and Comparative Example 1

[0582] Organic light-emitting devices were manufactured in the same manner as in Example 1, except that in forming the emission layer, the compounds shown in Table 2 were each used as an emitter.

[0583] The driving voltage (V), external quantum efficiency (EQE, %), and T of the organic light-emitting devices of Examples 1 to 2 and Comparative Example 1 were measured and evaluated by using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). 95 Life characteristics, where T 95 The time taken for the luminance to decrease from the initial luminance to 95% of its initial luminance (at 1,200 cd / m 2 ) in hours (hr)]. The results are shown in Table 2.

[0584] Table 2

[0585] Emission layer emitter Driving voltage(V) EQE(%) <![CDATA[T 95 (hr)]]> Example 1 Compound 355 4.37 22.2 48.3 Example 2 Compound 356 4.32 21.6 43.6 Comparative Example 1 Compound A 4.51 20.5 40.0

[0586]

[0587] As shown in Table 2, the organic light-emitting device according to the embodiment has excellent driving voltage, luminous efficiency, and life characteristics. In addition, compared with the organic light-emitting device of Comparative Example 1, the organic light-emitting devices of Examples 1 and 2 have lower driving voltage, higher external quantum efficiency, and significantly longer life.

[0588] Example 3

[0589] An organic light emitting device was manufactured in the same manner as in Example 1, except that when the emission layer was formed, the first host (H25), the second host (H26), and the emitter (compound 355) were co-deposited. In this regard, the first host and the second host were mixed in a weight ratio of 65:35, and the emitter was adjusted to 1.5 wt % based on the total weight of the first host, the second host, and the emitter.

[0590] Example 4 and Comparative Example 2

[0591] Organic light-emitting devices were manufactured in the same manner as in Example 3, except that in forming the emission layer, the compounds shown in Table 3 were each used as an emitter.

[0592] The driving voltage (V), external quantum efficiency (EQE, %), and T of the organic light-emitting devices of Examples 3-4 and Comparative Example 2 were measured and evaluated by using a current-voltage meter (Keithley 2400) and a brightness meter (Minolta Cs-1000A). 95 Life characteristics, where T 95 The time it takes for the brightness to decrease from the initial brightness to 95% (at 1,200 cd / m 2 The results are shown in Table 3.

[0593] Table 3

[0594] Emission layer emitter Driving voltage(V) EQE(%) <![CDATA[T 95 (hr)]]> Example 3 Compound 355 5.10 19.0 1.7 Example 4 Compound 356 5.07 17.8 1.4 Comparative Example 2 Compound A 5.28 16.3 1.4

[0595]

[0596] As shown in Table 3, the organic light-emitting device according to the embodiment has excellent driving voltage, luminous efficiency, and lifespan characteristics. In addition, compared with the organic light-emitting device of Comparative Example 2, the organic light-emitting devices of Examples 3 and 4 have lower driving voltage, higher external quantum efficiency, and longer or equal lifespan.

[0597] Due to the excellent luminescence characteristics and charge mobility characteristics of the heterocyclic compound, electronic devices such as organic light-emitting devices using the heterocyclic compound can have low driving voltage, high efficiency, and long life. Therefore, by using the heterocyclic compound, a high-quality organic light-emitting device can be realized. In addition, by using the heterocyclic compound, a diagnostic composition with high diagnostic efficiency can be realized.

[0598] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each embodiment should typically be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art 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 in, In equations 1 and 2, 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), CY1-CY3 are each independently C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, Ar1 and Ar2 are each independently a group represented by Formula 2, L1 is a single bond, substituted or unsubstituted C5-C 30 A carbocyclic group, or a substituted or unsubstituted C1-C 30 Heterocyclic groups, a1 is 1, 2, or 3, CY 21 -CY 24 Each independently is C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, R1, R2, R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , and R 70 Each is independently a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, 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 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 Alkyl aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q1)(Q2), -Si(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), -P(═S)(Q1)(Q2), or a group represented by Formula 3, Formula 3 Among them, in formula 3, X 31 For single bonds, O, S, N(R 301 ), or C(R 301 )(R 302 ), k31 is 0 or 1, CY 31 and CY 32 Each independently is C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, L 30 is a single bond, substituted or unsubstituted C5-C 30 A carbocyclic group, or a substituted or unsubstituted C1-C 30 Heterocyclic groups, a30 is 1, 2, or 3, R 301 , R 302 , R 310 , and R 320 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, 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 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 Alkyl aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, 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), b310 and b320 are each independently 1, 2, 3, 4, 5, 6, 7, or 8, b10, b20, b30, b40, b50, b60, and b70 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14, R1, R2, R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , R 70 , R 301 , R 302 , R 310 , and R 320 Two or more adjacent groups of 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups, 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 C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C2-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, or the substituted monovalent non-aromatic condensed heteropolycyclic group is: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, or C1-C 60 Alkoxy; C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, or C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -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 any combination thereof; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -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 any 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(Q 31 )(Q 32 );or Any combination of Q1-Q3, Q 11 -Q 13 , Q 21 -Q 23 , and Q 31 -Q 33 Each is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphoric acid group or its salt; unsubstituted or substituted with deuterium, C1-C 60 Alkyl, C6-C 60 Aryl, or any combination thereof substituted C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; C3-C 10 Cycloalkyl; C1-C 10 Heterocycloalkyl; C3-C 10 Cycloalkenyl; C2-C 10 Heterocycloalkenyl; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 Aryl, or any combination thereof substituted C6-C 60 Aryl; C6-C 60 Aryloxy; C6-C 60 Arylthio; C1-C 60 heteroaryl; a monovalent non-aromatic fused polycyclic group; or a monovalent non-aromatic fused heteropolycyclic group, and * indicates the binding site with the adjacent atom.

2. The heterocyclic compound of claim 1, wherein CY1-CY3 are each independently a phenyl group, a naphthalene group, a phenanthrene group, a fluorene group, a spirobifluorene group, a pyridine group, a pyrimidine 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 dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermanol group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, or a dibenzothiophene 5,5-dioxide group.

3. The heterocyclic compound according to claim 1, wherein CY1 and CY2 are each independently a group represented by any one of formulae 1-1 to 1-9: in, In formulas 1-1 to 1-9, R 11 -R 18 and R 11a -R 18a Each independently as claimed in claim 1 regarding R 10 As described, X2 is O, S, Se, N(R3), C(R3)(R4), Si(R3)(R4), Ge(R3)(R4), B(R3), P(R3), P(═O)(R3), S(═O)2, or C(═O), R3 and R4 are each independently as described with respect to R1 in claim 1, and * 1 and* 2 Each represents a binding site with a neighboring atom.

4. The heterocyclic compound as claimed in claim 1, wherein CY 21 -CY 24 Each is independently a benzene group, a naphthyl 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.

5. The heterocyclic compound according to claim 1, wherein the group represented by Formula 2 is a group represented by any one of Formulas 2A to 2D: in, In Formulas 2A to 2D, CY 22 -CY 24 , L1, a1, R 50 , R 60 , R 70 , b50, b60, and b70 are each as described in claim 1, R 41 -R 44 Each of the claims 1 regarding R 40 described, and * indicates the binding site with the adjacent atom.

6. The heterocyclic compound according to claim 1, wherein the group represented by Formula 2 is a group represented by any one of Formulas 2-1 to 2-4: in, In formulas 2-1 to 2-4, L1 and a1 are each as described in claim 1, R 41 -R 44 Each of the claims 1 regarding R 40 As described, R 51 -R 54 Each of the claims 1 regarding R 50 As described, R 61 -R 64 Each of the claims 1 regarding R 60 As described, R 71 -R 74 Each of the claims 1 regarding R 70 described, and * indicates the binding site with the adjacent atom.

7. The heterocyclic compound according to claim 1, wherein L1 is: a single bond, a phenylene group, a naphthylene group, a phenanthrenyl group, a fluorenyl group, or a pyrenyl group; or a phenylene group, a naphthylene group, a phenanthylene group, a fluorenylene group, or a pyrenylene group, each of which is substituted by deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 20 Alkyl, C1-C containing deuterium 20 Alkyl, fluorinated C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, naphthyl, anthracenyl, or any combination thereof.

8. The heterocyclic compound as claimed in claim 1, wherein R1, R2, R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , R 70 , R 301 , R 302 , R 310 , and R 320 Each independently is: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF5, C1-C 20 Alkyl, or C1-C 20 Alkoxy; C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C containing deuterium 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) norbornene, (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, silanol, phenyl, (C1-C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidinyl, or any 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, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl , dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C containing deuterium 20 Alkyl, fluorinated C1-C 20 Alkyl, C1-C 20 alkoxy, 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) norbornene, (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, silanol, phenyl, (C1-C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, or any combination thereof; or -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

9. The heterocyclic compound as claimed in claim 1, wherein R 10 , R 20 , and R 30 At least one of them is a group represented by Formula 3.

10. The heterocyclic compound according to claim 1, wherein the group represented by Formula 3 is represented by any one of Formulas 3-1 to 3-3: in, In formulas 3-1 to 3-3, L 30 and a30 are each as described in claim 1, X 301 As claimed in claim 1, regarding X 31 As described, X 311 C(R 311 ) or N, X 312 C(R 312 ) or N, X 313 C(R 313 ) or N, X 314 C(R 314 ) or N, X 315 C(R 315 ) or N, X 321 C(R 321 ) or N, X 322 C(R 322 ) or N, X 323 C(R 323 ) or N, X 324 C(R 324 ) or N, X 325 C(R 325 ) or N, R 311 -R 315 Each independently as claimed in claim 1 regarding R 310 As described, R 321 -R 325 Each independently as claimed in claim 1 regarding R 320 described, and * indicates the binding site with the adjacent atom.

11. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is represented by Formula 11-1 or 11-2: Formula 11-1 Formula 11-2 in, In formulas 11-1 and 11-2, CY1, CY2, Ar1, Ar2, R 10 , R 20 , b10, and b20 are each as described in claim 1, X 11 is a single bond, O, S, Se, N(R1), C(R1)(R2), Si(R1)(R2), Ge(R1)(R2), B(R1), P(R1), P(═O)(R1), S(═O)2, or C(═O), R1 and R2 are each as described in claim 1, and R 31 -R 33 Each independently as claimed in claim 1 regarding R 30 as described. 12 . The heterocyclic compound according to claim 1 , wherein the heterocyclic compound has a symmetrical structure or an asymmetrical structure.

13. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is one of compounds 1 to 360:

14. Organic light-emitting device, comprising: a first electrode; a second electrode; as well as an organic layer disposed between the first electrode and the second electrode and including an emission layer, The organic layer comprises the heterocyclic compound as claimed in any one of claims 1 to 13. The organic light emitting device of claim 14 , wherein the emission layer comprises the heterocyclic compound.

16. The organic light emitting device of claim 15, wherein the emission layer comprises a host and an emitter, and The emitter includes the heterocyclic compound. The organic light emitting device of claim 16 , wherein the amount of the host is greater than the amount of the heterocyclic compound. The organic light emitting device of claim 16 , wherein the emission layer further comprises a sensitizer.

19. An organic light emitting device as claimed in claim 18, wherein the sensitizer comprises a phosphorescent dopant. 20 . The organic light emitting device of claim 15 , wherein the emission layer emits blue light having a maximum emission wavelength of 400 nm to 490 nm.

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