Heterocyclic compound and organic light-emitting device comprising the same

Abstract

Provided are a heterocyclic compound and an organic light-emitting device including the same. The heterocyclic compound is represented by Formula 1 and has an asymmetric structure. In Formula 1, X1 is O or Se, Ar1 is a group represented by Formula 1A, and Ar2 is a group represented by Formula 1B, and other substituents and parameters are understood as described in the detailed description. Formula 1#imgabs0##imgabs1#.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0158454 filed in the Korean Intellectual Property Office on December 2, 2019, the contents of which are incorporated herein by reference in their entirety. Technical Field

[0003] One or more embodiments relate to a heterocyclic compound and an organic light-emitting device 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 producing a full-color image.

[0005] In an example, an organic light emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes 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. These excitons transition from an excited state to a ground state, thereby generating light. Summary of the invention

[0006] One or more embodiments provide 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] One aspect of the present disclosure provides a heterocyclic compound represented by Formula 1 and having an asymmetric structure.

[0009] Formula 1

[0010]

[0011]

[0012] In Formulas 1, 1A and 1B,

[0013] X 1 Can be O or Se,

[0014] Ar 1 may be a group represented by Formula 1A, and Ar 2 may be a group represented by Formula 1B,

[0015] L1 and L 2 may be independently substituted or unsubstituted C 5 -C 30 Carbocyclic group, substituted or unsubstituted C 1 -C 30 Heterocyclic group, or any combination thereof,

[0016] a1 and a2 can each independently be an integer of 0-3,

[0017] When a1 is 2 or greater, two or more L 1 may be the same as or different from each other, and when a2 is 2 or greater, two or more L 2 may be the same or different from each other,

[0018] R 1 , R 2 , R 10 , R 20 , R 30 and R 40 can be independently 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, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or any combination thereof,

[0019] b1 and b2 can each independently be an integer of 1-5,

[0020] When b1 is 2 or greater, two or more R 1 may be the same as or different from each other, and when b2 is 2 or greater, two or more R 2 may be the same or different from each other,

[0021] b10 and b20 can each independently be an integer of 1-8,

[0022] b30 and b40 can each independently be an integer of 1-3,

[0023] c1 and c2 can each independently be an integer of 1-8,

[0024] The sum of b10 and c1 can be 9 and the sum of b20 and c2 can be 9, and

[0025] 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 6 -C 60 Aryloxy, substituted C 6 -C 60Arylthio, substituted C 1 -C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is:

[0026] 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, or any combination thereof,

[0027] Each of the following is substituted by at least one C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or any combination thereof: 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, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 ), and -B(Q 16 )(Q 17 ),

[0028] 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, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof,

[0029] Each of the following is substituted by at least one 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, or any combination thereof: 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, C1 -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, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 ), and -B(Q 26 )(Q 27 ),or

[0030] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 ), or any combination thereof,

[0031] Where Q 1 -Q 7 , Q 11 -Q 17 , Q 21 -Q 27 , and Q 31 -Q 37 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 C2 -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 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof.

[0032] An organic light emitting device according to another aspect includes a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode and including at least one heterocyclic compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] By combining Figure 1 The above and other aspects, features and advantages of some embodiments of the present disclosure will become more apparent upon consideration of the following description. Figure 1 A schematic cross-sectional view showing an organic light emitting device according to an embodiment is shown. DETAILED DESCRIPTION

[0034] 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 embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the following only describes the embodiments to illustrate aspects by reference to the accompanying drawings. As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. 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.

[0035] 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.

[0036] 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.

[0037] The terms used herein are for the purpose of describing specific embodiments only and are not intended to be limiting. As used herein, "a, an," "the," and "at least one" do not represent a limitation of quantity and are intended to cover both the singular and the plural, unless the context clearly indicates otherwise. For example, "an element" has the same meaning as "at least one element," unless the context clearly indicates otherwise.

[0038] "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.

[0039] 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 shown 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" may include 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..." may include both "above..." and "below..." orientations.

[0040] As used herein, "about" or "approximately" includes 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 that the deviation from the stated value is within one or more standard deviations, or within ±10% or 5%.

[0041] 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 the same meaning as they have 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.

[0042] 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 illustrated 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.

[0043] The heterocyclic compound according to an embodiment of the present disclosure may be represented by Formula 1:

[0044]

[0045] X in Formula 1 1 Can be O or Se.

[0046] In one or more embodiments, X 1 Can be O. In one or more embodiments, X 1 Can be Se.

[0047] In formula 1, Ar 1 may be a group represented by Formula 1A, and Ar 2 It may be a group represented by Formula 1B.

[0048] In one or more embodiments, Ar 1 It may be a group represented by one of Formulae 1A-1 to 1A-5:

[0049]

[0050] In Formulae 1A-1 to 1A-5,

[0051] L 1 、a1、R 1 and b1 may be the same as described in this specification,

[0052] R 11 -R 19 Can be related to R 10 Same as described, and

[0053] *Indicates the binding site with the adjacent atom.

[0054] In one or more embodiments, Ar 2 It may be a group represented by one of Formulae 2A-1 to 2A-5:

[0055]

[0056] In Formulae 2A-1 to 2A-5,

[0057] L 2 , a2, R 2 and b2 may be the same as described in this specification,

[0058] R 21 -R 29 Can be related to R 20 Same as described, and

[0059] *Indicates the binding site with the adjacent atom.

[0060] In one or more embodiments, the heterocyclic compound represented by Formula 1 may be a compound represented by one of Formulas 1-1 to 1-6:

[0061]

[0062] In formulas 1-1 to 1-6,

[0063] X 1 ,Ar 1 and Ar 2 can be the same as described in this specification,

[0064] R 31 -R 34 Can be related to R 30 Same as described,

[0065] R 41 -R 44 Can be related to R 40 Same as described.

[0066] L in Formula 1A and 1B 1 and L 2 may be independently substituted or unsubstituted C 5 -C 30 Carbocyclic group, substituted or unsubstituted C 1 -C 30 A heterocyclic group, or any combination thereof.

[0067] In one or more embodiments, L 1 and L 2 Each of the following may be independently selected from: phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthenylene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrene, pyren ... phenanthrenylene, fluorenylene, phenanth phenylene, tetraphenylene, perylenene, pentphenylene, or any combination thereof; or

[0068] Each of the following is selected from at least one substituted phenylene, pentalene, indenylene, naphthylene, azulenylene, heptalene, acenaphthene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenyl ... phenanthrenylene, fluorenylene, benzo[9,10]phenan phenylene, tetraphenylene, perylene, perylene, pentphenylene, or any combination thereof: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group 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 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 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.

[0069] a1 and a2 in Formula 1A and 1B may each independently be an integer of 0 to 3. When a1 is 2 or greater, two or more L 1 When a2 is 2 or more, two or more L 2 Can be the same as or different from each other.

[0070] R in Formula 1, 1A and 1B 1 , R 2 , R 10 , R 20 , R 30 and R 40 can be independently 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, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or any combination thereof.

[0071] In one or more embodiments, R 1 , R 2 , R 10 , R 20 , R 30 and R 40 Can be independently:

[0072] 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, C 1 -C 20 Alkoxy, or any combination thereof;

[0073] Each of the following is substituted by at least one C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or any combination thereof: 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 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, and pyrimidinyl;

[0074] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or any combination thereof;

[0075] Each of which is selected from at least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or any combination thereof: 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, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl; or

[0076] -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or any combination thereof,

[0077] Where Q 1 -Q 9 Can be independently:

[0078] -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 CH 3 、-CD 2 CD 3 、-CD 2 CD 2 H.-CD 2 CDH 2 , or any combination thereof;

[0079] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, or any combination thereof; or

[0080] each selected from at least one substituted n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, or any combination thereof: deuterium, C 1 -C 10Alkyl, and phenyl.

[0081] b1 and b2 in Formula 1, 1A and 1B may each independently be an integer of 1 to 5. When b1 is 2 or greater, two or more R 1 When b2 is 2 or more, two or more R 2 Can be the same as or different from each other.

[0082] b10 and b20 in Formulae 1, 1A and 1B may each independently be an integer of 1 to 8. When b10 is 2 or greater, two or more R 10 When b20 is 2 or more, two or more R 20 Can be the same as or different from each other.

[0083] b30 and b40 in Formulae 1, 1A and 1B may each independently be an integer of 1 to 3. When b30 is 2 or greater, two or more R 30 When b40 is 2 or more, two or more R 40 Can be the same as or different from each other.

[0084] c1 and c2 in Formula 1, 1A and 1B may each independently be an integer of 1 to 8. When c1 is 2 or greater, two or more -(L 1 ) a1 -(R 1 ) b1 The groups may be identical or different from each other. When c2 is 2 or greater, two or more -(L 2 ) a2 -(R 2 ) b2 The groups may be the same as or different from each other.

[0085] In Formulas 1, 1A, and 1B, the sum of b10 and c1 may be 9 and the sum of b20 and c2 may be 9.

[0086] In one or more embodiments, b10 may be 8 and c1 may be 1.

[0087] In one or more embodiments, b20 may be 8 and c2 may be 1.

[0088] In one or more embodiments, R 1 and R 2 can be independently deuterium, -F, -Cl, -Br, -I, -CF 3 、-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 -C60 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, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or any combination thereof.

[0089] In one or more embodiments, R 1 and R 2 can be independently deuterium, -F, -CF 3 , cyano, nitro, -SF 5 , a group represented by formula 9-1 to 9-19, a group represented by formula 10-1 to 10-208, or any combination thereof:

[0090]

[0091]

[0092]

[0093]

[0094] In Formulae 9-1 to 9-19 and 10-1 to 10-208, * represents a bonding site with an adjacent atom, Ph may be a phenyl group, and TMS may be a trimethylsilyl group.

[0095] In one or more embodiments, R 1 and R 2 Can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, -CF 3 , hydroxyl, cyano, nitro, -SF 5 , amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or any combination thereof;

[0096] Each of the following is substituted by at least one C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or any combination thereof: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl;

[0097] Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenanthrenyl, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzo oxazolyl, benzimidazolyl, furyl, benzofuranyl, thienyl, benzothienyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl, Azolyl, Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, imidazopyrimidinyl, imidazopyridinyl, or any combination thereof; or

[0098] each selected from at least one substituted cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenanthrenyl, hexaphenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzo oxazolyl, benzimidazolyl, furyl, benzofuranyl, thienyl, benzothienyl, thiazolyl, isothiazolyl, benzothiazolyl, isothiazolyl, Azolyl, Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, imidazopyrimidinyl, imidazopyridinyl, or any combination thereof: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 20 Alkyl, C 2 -C 20 Alkenyl, C 2 -C 20 Alkynyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, fluorenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, phthalazinyl, quinoxalinyl, cinnolinyl, and quinazolinyl.

[0099] In one or more embodiments, R 10 , R 20 , R 30 and R 40 can be independently hydrogen, deuterium, -F, -CF 3 , cyano, nitro, -SF 5 、-CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , a group represented by formula 9-1 to 9-19, a group represented by formula 10-1 to 10-208, or any combination thereof:

[0100]

[0101]

[0102]

[0103]

[0104] In Formulae 9-1 to 9-19 and 10-1 to 10-208, * represents a bonding site with an adjacent atom, Ph may be a phenyl group, and TMS may be a trimethylsilyl group.

[0105] In one or more embodiments, R 10 , R 20 , R 30 and R 40 Each may be hydrogen.

[0106] In one or more embodiments, the heterocyclic compound represented by Formula 1 may be represented by one of Formulas 10-1 to 10-6:

[0107]

[0108]

[0109] In formulas 10-1 to 10-6,

[0110] X 1 , L 1 , L 2 , a1, a2, R 1 , R 2 , b1 and b2 are the same as described above.

[0111] In one or more embodiments, the heterocyclic compound may be one of compounds 1 to 2120:

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[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]

[0217]

[0218] The heterocyclic compound represented by Formula 1 may satisfy the structure of Formula 1 and have an asymmetric structure, and therefore, its crystallinity (crystallinity) may be reduced. Therefore, in the heterocyclic compound, close packing between molecules may be prevented, and therefore, the heterocyclic compound represented by Formula 1 may have an effect of obtaining relatively excellent amorphous thin film characteristics.

[0219] As described above, the heterocyclic compound represented by Formula 1 may have such electrical characteristics that it is suitable for use as a material for an organic light-emitting device, such as a host material in an emission layer, a hole transport material, an electron transport material, etc. Therefore, an organic light-emitting device using the heterocyclic compound may have high efficiency and / or a long lifespan.

[0220] In one or more embodiments, the heterocyclic compound represented by Formula 1 satisfies Equation 1:

[0221] Equation 1

[0222] E(T1) <E(S1)<2×E(T1)。

[0223] In Equation 1, E(T1) represents the lowest excited triplet energy level of the heterocyclic compound and E(S1) represents the lowest excited singlet energy level of the heterocyclic compound.

[0224] In one or more embodiments, the heterocyclic compound represented by Formula 1 satisfies Equation 2:

[0225] Equation 2

[0226] [2×E(T1)]-E(S1)<0.5eV.

[0227] In Equation 2, E(T1) represents the lowest excited triplet energy level of the heterocyclic compound and E(S1) represents the lowest excited singlet energy level of the heterocyclic compound.

[0228] Since the heterocyclic compound represented by Formula 1 satisfies Equation 1 and / or Equation 2, a triplet-triplet fusion (TTF) phenomenon in which triplet excitons fuse to generate singlet excitons may be very likely to occur. Therefore, when the heterocyclic compound is applied to an organic light-emitting device, fluorescent emission may occur from singlet excitons generated by the TTF phenomenon, thereby improving the emission efficiency and lifespan of the device.

[0229] For example, the highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), triplet energy level (E(T1)), and singlet energy level (E(S1)) of compounds 1, 113, 134, 171, 1121, and 2102 were measured using the DFT method of the Gaussian program (B3LYP, structural optimization at the 6-31G (d, p) level). The evaluation results are shown in Table 1 below.

[0230] Table 1

[0231]

[0232]

[0233]

[0234] From Table 1, it can be seen that the heterocyclic compound represented by Formula 1 has electrical characteristics suitable for use in electronic devices, for example, as a material for an emission layer for an organic light emitting device.

[0235] 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.

[0236] The heterocyclic compound represented by Formula 1 may be suitable for use in an organic layer, for example, as an emission layer material, a hole transport region material, and / or an electron transport region material of the organic layer. Therefore, another aspect of the present disclosure provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode and comprising an emission layer, wherein the organic layer may include at least one heterocyclic compound represented by Formula 1.

[0237] Due to including the organic layer including the heterocyclic compound represented by Formula 1 as described above, the organic light emitting device may have low driving voltage, high efficiency, high brightness, high quantum emission efficiency, and a long lifespan.

[0238] In one or more embodiments, in the organic light-emitting device,

[0239] The first electrode is an anode and the second electrode is a cathode,

[0240] The organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,

[0241] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and

[0242] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof, but embodiments of the present disclosure are not limited thereto.

[0243] For example, the emission layer of the organic light emitting device may include at least one heterocyclic compound represented by Formula 1.

[0244] In one or more embodiments, the emission layer in the organic light-emitting device may include a host and a dopant, and the host may include at least one heterocyclic compound represented by Formula 1, and the dopant may include a phosphorescent dopant or a fluorescent dopant. For example, the dopant may include a phosphorescent dopant (e.g., an organic metal compound represented by Formula 81). In addition to the heterocyclic compound represented by Formula 1, the host may further include any other host.

[0245] The emission layer may emit red light, green light, or blue light.

[0246] In one or more embodiments, the emission layer may include a fluorescent dopant, but embodiments of the present disclosure are not limited thereto.

[0247] In one or more embodiments, the emission layer may include a phosphorescent dopant, but embodiments of the present disclosure are not limited thereto.

[0248] In one or more embodiments, the heterocyclic compound represented by Formula 1 may be included in a hole transport region of the organic light emitting device.

[0249] For example, the hole transport region of the organic light emitting device includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, and at least one of the hole injection layer, the hole transport layer, and the electron blocking layer may include the heterocyclic compound represented by Formula 1.

[0250] In one or more embodiments, the heterocyclic compound represented by Formula 1 may be included in the electron transport region of the organic light emitting device.

[0251] For example, the electron transport region of the organic light-emitting device includes at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer, and the at least one selected from the hole blocking layer, the electron transport layer, and the electron injection layer may include a heterocyclic compound represented by Formula 1.

[0252] In one or more embodiments, the hole transport region of the organic light emitting device may include an electron blocking layer, and the heterocyclic compound represented by Formula 1 may be included in the electron blocking layer. The electron blocking layer may be in direct contact with the emission layer.

[0253] In one or more embodiments, the electron transport region of the organic light emitting device may include a hole blocking layer, and the heterocyclic compound represented by Formula 1 may be included in the hole blocking layer. The hole blocking layer may directly contact the emission layer.

[0254] In one or more embodiments, the organic layer of the organic light-emitting device may further include a fluorescent dopant in addition to the heterocyclic compound represented by Formula 1.

[0255] For example, the fluorescent dopant may be a condensed polycyclic compound or a styryl compound.

[0256] For example, the fluorescent dopant may include one of the following: a naphthalene-containing core, a fluorene-containing core, a spiro-bifluorene-containing core, a benzofluorene-containing core, a dibenzofluorene-containing core, a phenanthrene-containing core, an anthracene-containing core, a fluoranthene-containing core, a benzo[9,10]phenanthrene-containing core, a pyrene-containing core, a A core containing tetracene, a core containing chrysene, a core containing perylene, a core containing pentaphene, a core containing indenoanthracene, a core containing bianthracene, a core represented by Formulae 501-1 to 501-18, or any combination thereof, but the embodiments of the present disclosure are not limited thereto:

[0257]

[0258] In one or more embodiments, the fluorescent dopant may be a styryl-amine-based compound or a styryl-carbazole-based compound, but embodiments of the present disclosure are not limited thereto.

[0259] In one or more embodiments, the fluorescent dopant may be a compound represented by Formula 501:

[0260] Formula 501

[0261]

[0262] In formula 501,

[0263] Ar 501 Can be:

[0264] Naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, group, a naphthacene group, a chrysene group, a perylene group, a pentaphene group, an indenoanthracene group, a bianthracene group, or a group (core) represented by Formulae 501-1 to 501-18; or

[0265] Each is selected from at least one substituted naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, A group, a naphthacene group, a phenanthracene group, a perylene group, a pentaphene group, an indenoanthracene group, a bianthracene group, or a group represented by the formulae 501-1 to 501-18: 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, 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, C3 -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, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, and -Si(Q 501 )(Q 502 )(Q 503 )(where Q 501 -Q 503 can be independently hydrogen, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof);

[0266] L 501 -L 503 may be independently substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group, or any combination thereof,

[0267] R 501 and R 502 Can be independently:

[0268] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, or any combination thereof; or

[0269] Each of which is selected from at least one substituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, or any combination thereof: 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 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, xd1-xd3 may each independently be 0, 1, 2 or 3, and

[0270] xd4 can be 0, 1, 2, 3, 4, 5 or 6.

[0271] For example, in Equation 501,

[0272] Ar 501 Can be:

[0273] Naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, group, a naphthacene group, a chrysene group, a perylene group, a pentaphene group, an indenoanthracene group, a bianthracene group, or a group represented by Formulae 501-1 to 501-18; or

[0274] Each is selected from at least one substituted naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, A group, a naphthacene group, a phenanthracene group, a perylene group, a pentaphene group, an indenoanthracene group, a bianthracene group, or a group represented by the formulae 501-1 to 501-18: 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, C1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, and -Si(Q) 501 )(Q 502 )(Q 503 )(Q 501 -Q 503 can be independently hydrogen, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, or any combination thereof,

[0275] L 501 -L 503 About L 21 Same as described,

[0276] xd1-xd3 can each independently be 0, 1 or 2, and

[0277] xd4 may be 0, 1, 2 or 3, but embodiments of the present disclosure are not limited thereto.

[0278] In one or more embodiments, the fluorescent dopant may include a compound represented by one of Formulas 502-1 to 502-5:

[0279] Formula 502-1

[0280]

[0281] Formula 502-2

[0282]

[0283] Formula 502-3

[0284]

[0285] Formula 502-4

[0286]

[0287] Formula 502-5

[0288]

[0289] In formulas 502-1 to 502-5,

[0290] X 51 Can be N or C-[(L501 ) xd1 -R 501 ], X 52 Can be N or C-[(L 502 ) xd2 -R 502 ], X 53 Can be N or C-[(L 503 ) xd3 -R 503 ], X 54 Can be N or C-[(L 504 ) xd4 -R 504 ], X 55 Can be N or C-[(L 505 ) xd5 -R 505 ], X 56 Can be N or C-[(L 506 ) xd6 -R 506 ], X 57 Can be N or C-[(L 507 ) xd7 -R 507 ], and X 58 Can be N or C-[(L 508 ) xd8 -R 508 ],

[0291] L 501 -L 508 Each of them is related to L in formula 501 501 Same as described,

[0292] xd1-xd8 are each the same as described with respect to xd1 in Formula 501,

[0293] R 501 -R 508 Can be independently:

[0294] 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 20 Alkyl, C 1 -C 20 Alkoxy, or any combination thereof,

[0295] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, or any combination thereof; or

[0296] Each of which is selected from at least one substituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, or any combination thereof: 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 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl, and dibenzothiophenyl,

[0297] xd11 and xd12 can each independently be an integer from 0 to 5, and

[0298] R 501 -R 504 Two of may be optionally linked together to form a saturated or unsaturated ring, and

[0299] R 505 -R 508 Two of may be optionally linked together to form a saturated or unsaturated ring.

[0300] The fluorescent dopant may include, for example, at least one compound selected from the following compounds FD(1) to FD(16) and FD1 to FD14:

[0301]

[0302]

[0303] In one or more embodiments, the organic layer of the organic light emitting device may further include a phosphorescent dopant in addition to the heterocyclic compound represented by Formula 1.

[0304] For example, the phosphorescent dopant may further include an organic metal compound represented by Formula 81:

[0305] Formula 81

[0306] M(L 81 ) n81 (L 82 ) n82

[0307] Formula 81A

[0308]

[0309] In equations 81 and 81A,

[0310] M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh),

[0311] L 81 may be a ligand represented by Formula 81A, n81 may be an integer of 1 to 3, and when n81 is 2 or greater, two or more L 81 may be the same or different from each other,

[0312] L 82 may be an organic ligand, n82 may be an integer of 0-4, and when n82 is 2 or greater, two or more L 82 may be the same or different from each other,

[0313] Y 81 -Y 84 may be independently carbon (C) or nitrogen (N),

[0314] Y 81 and Y 82 can be connected to each other via single bonds or double bonds, and Y 83 and Y 84 can be connected to each other via single or double bonds,

[0315] CY 81 and CY 82 Can be independently C 5 -C 30 Carbocyclic group, C 2 -C 30 Heterocarbocyclic group, or any combination thereof,

[0316] In addition, CY 81 and CY 82 may optionally be linked to each other via an organic linking group,

[0317] R 81 -R 85can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF 5 , 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, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 81 )(Q 82 )(Q 83 )、-N(Q 84 )(Q 85 )、-B(Q 86 )(Q 87 )、-P(=O)(Q 88 )(Q 89 ), or any combination thereof,

[0318] a81-a83 can each independently be an integer of 0-5,

[0319] When a81 is 2 or more, two or more R 81 may be the same or different from each other,

[0320] When a82 is 2 or more, two or more R 82 may be the same or different from each other,

[0321] When a81 is 2 or greater, two adjacent R81 Can be optionally linked to form a saturated or unsaturated C 2 -C 30 ring (e.g., a benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a bicyclo[2.2.1]heptane ring, a naphthalene ring, a benzindene ring, a benzindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring) or is replaced by at least one R 88 Substituted saturated or unsaturated C 2 -C 30 rings (eg, each of which is represented by at least one R 88 a substituted benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a bicyclo[2.2.1]heptane ring, a naphthalene ring, a benzindene ring, a benzindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring),

[0322] When a82 is 2 or greater, two adjacent R 82 Can be optionally linked to form a saturated or unsaturated C 2 -C 30 ring (e.g., a benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a bicyclo[2.2.1]heptane ring, a naphthalene ring, a benzindene ring, a benzindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring) or is replaced by at least one R 89 Substituted saturated or unsaturated C 2 -C 30 rings (eg, each of which is represented by at least one R 89 a substituted benzene ring, a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a norbornane ring, a bicyclo[2.2.1]heptane ring, a naphthalene ring, a benzindene ring, a benzindole ring, a benzofuran ring, a benzothiophene ring, a pyridine ring, a pyrimidine ring, or a pyrazine ring),

[0323] R 88 Can be related to R 81 Same as described,

[0324] R 89 Can be related to R 82 Same as described,

[0325] * and *' in formula 81A each represent a binding site with M in formula 81, and

[0326] Substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C60 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 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a 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, -Si(Q 91 )(Q 92 )(Q 93 ), or any combination thereof,

[0327] Where Q 81 -Q 89 and Q 91 -Q 93 can be independently hydrogen, deuterium, C 1 -C60 Alkyl, 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 1 -C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof.

[0328] In one or more embodiments, in Formula 81A,

[0329] a83 can be 1 or 2,

[0330] R 83 -R 85 Can be independently:

[0331] -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 CH 3 、-CD 2 CD 3 、-CD 2 CD 2 H.-CD 2 CDH 2 , or any combination thereof;

[0332] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, or any combination thereof; or

[0333] each selected from at least one substituted n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, or any combination thereof: deuterium, C 1 -C 10 An alkyl group, and a phenyl group, but the embodiments of the present disclosure are not limited thereto.

[0334] In one or more embodiments, in Formula 81A,

[0335] Y 81 Can be nitrogen, Y 82 and Y 83 Can be carbon, Y 84 may be nitrogen or carbon, and

[0336] CY 81 and CY 82 Each of the following may be independently a cyclopentadiene group, a phenyl group, a heptalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, an acenaphthene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthren group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, group, tetraphenyl group, phenanthracene group, perylene group, pentacene group, hexaphenyl group, pentaphene group, rubine group, coronaphenyl group, ovaphenyl group, pyrrole group, isoindole group, indole group, indazole group, pyrazole group, imidazole group, triazole group, Azole group, iso Azole group, a benzofuran group, a benzothiophene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiazole group, a benzo Azole group, isobenzo The invention further comprises a benzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, a 2,3-dihydro-1H-imidazole group, or any combination thereof.

[0337] In one or more embodiments, in Formula 81A, Y 81 Can be nitrogen, Y 82 -Y 84 Can be carbon, CY 81 It may be a 5-membered ring in which two nitrogen atoms are ring atoms, and CY 82It may be a benzene group, a naphthalene group, a fluorene group, a dibenzofuran group, or a dibenzothiophene group, but embodiments of the present disclosure are not limited thereto.

[0338] In one or more embodiments, in Formula 81A, Y 81 Can be nitrogen, Y 82 -Y 84 Can be carbon, CY 81 may be an imidazole group or a 2,3-dihydro-1H-imidazole group, and CY 82 It may be a benzene group, a naphthalene group, a fluorene group, a dibenzofuran group, or a dibenzothiophene group, but embodiments of the present disclosure are not limited thereto.

[0339] In one or more embodiments, in Formula 81A,

[0340] Y 81 can be nitrogen and Y 82 -Y 84 Can be carbon,

[0341] CY 81 It can be a pyrrole group, a pyrazole group, an imidazole group, a triazole group, Azole group, iso Azole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, pyridine group, pyrimidine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, benzimidazole group, isobenzothiazole group, benzo Azole group, or isobenzo an azole group, and

[0342] CY 82 It can be a cyclopentadiene group, a benzene group, a naphthalene group, a fluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a benzo[9,10]phenanthrene group, a pyrene group, group, a perylene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, or a dibenzosilole group.

[0343] In one or more embodiments, in Formula 81A,

[0344] R 81 and R 82 Can be independently:

[0345] 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 , C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or any combination thereof;

[0346] Each of the following is substituted by at least one C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or any combination thereof: 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 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, and pyrimidinyl;

[0347] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or any combination thereof;

[0348] Each of which is selected from at least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or any combination thereof: 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, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl; or

[0349] -B(Q 86 )(Q 87 ), or -P(=O)(Q 88 )(Q 89 ), or any combination thereof,

[0350] Where Q 86 -Q 89 Can be independently:

[0351] -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 CH 3 、-CD 2 CD 3 、-CD 2 CD 2 H.-CD 2 CDH 2 , or any combination thereof;

[0352] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, or any combination thereof; or

[0353] each selected from at least one substituted n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, or any combination thereof: deuterium, C 1 -C 10 Alkyl, and phenyl.

[0354] In one or more embodiments, in Formula 81A, R selected from a81 81 and R with a quantity of a82 82 At least one of may be a cyano group.

[0355] In one or more embodiments, in Formula 81A, R selected from a82 82 At least one of may be a cyano group.

[0356] In one or more embodiments, in Formula 81A, R selected from a81 81 and R with a quantity of a82 82 At least one of may be deuterium.

[0357] In one or more embodiments, L in Formula 81 82 It may be a ligand represented by one of the formulae 3-1(1) to 3-1(69), 3-1(71) to 3-1(79), 3-1(81) to 3-1(88), 3-1(91) to 3-1(98), and 3-1(101) to 3-1(114):

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364] In Formulas 3-1(1) to 3-1(69), 3-1(71) to 3-1(79), 3-1(81) to 3-1(88), 3-1(91) to 3-1(98), and 3-1(101) to 3-1(114),

[0365] X 1 Can be O, S, C (Z 21 )(Z 22 ), or N(Z 23 ),

[0366] X 31 Can be N or C(Z 1a ) and X 32 Can be N or C(Z 1b ),

[0367] X 41 Can be O, S, N (Z 1a ), or C(Z 1a )(Z 1b ),

[0368] Z 1 -Z 4 , Z 1a , Z 1b , Z 1c , Z 1d , Z 2a , Z 2b , Z 2c , Z 2d , Z 11 -Z 14 and Z 21 -Z 23Can be independently:

[0369] 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, C 1 -C 20 Alkoxy, or any combination thereof;

[0370] Each of the following is substituted by at least one C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or any combination thereof: 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 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, and pyrimidinyl;

[0371] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or any combination thereof;

[0372] Each of which is selected from at least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or any combination thereof: 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, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl; or

[0373] -B(Q 86 )(Q 87 )、-P(=O)(Q 88 )(Q 89 ), or any combination thereof,

[0374] Where Q 86 -Q 89 Can be independently:

[0375] -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 CH 3 、-CD 2 CD 3 、-CD 2 CD 2 H.-CD 2 CDH 2 , or any combination thereof;

[0376] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, or any combination thereof; or

[0377] each of which is selected from at least one substituted n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl: deuterium, C 1 -C 10 Alkyl, and phenyl;

[0378] d2 and e2 can each independently be 0 or 2,

[0379] e3 can be an integer from 0 to 3.

[0380] d4 and e4 can each independently be an integer from 0 to 4,

[0381] d6 and e6 can each independently be an integer from 0 to 6,

[0382] d8 and e8 can each independently be an integer from 0 to 8,

[0383] * and *' each represent a binding site to M in Formula 1.

[0384] In one or more embodiments, in Formula 81, M may be Ir and the sum of n81 and n82 may be 3; or M may be Pt and the sum of n81 and n82 may be 2.

[0385] In one or more embodiments, the organometallic compound represented by Formula 81 may be electrically neutral rather than a salt consisting of a pair of cations and anions.

[0386] In one or more embodiments, the organometallic compound represented by Formula 81 may include PD1 to PD78 and FIr 6 At least one compound, but the embodiments of the present disclosure are not limited thereto.

[0387]

[0388]

[0389]

[0390] As used herein, the expression “(the organic layer) includes at least one heterocyclic compound” may include the case where “(the organic layer) includes the same heterocyclic compound represented by Formula 1” and the case where “(the organic layer) includes two or more different heterocyclic compounds represented by Formula 1”.

[0391] For example, the organic layer may include only Compound 1 as the heterocyclic compound. In this regard, Compound 1 may be present only in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include Compound 1 and Compound 2 as the heterocyclic compound. In this case, Compound 1 and Compound 2 may be present in the same layer (for example, Compound 1 and Compound 2 may all be present in the emission layer) or in different layers (for example, Compound 1 may be present in the emission layer and Compound 2 may be present in the hole blocking layer).

[0392] The first electrode may be an anode as a hole injection electrode, and the second electrode may be a cathode as an electron injection electrode; or the first electrode may be a cathode as an electron injection electrode, and the second electrode may be an anode as a hole injection electrode.

[0393] The term "organic layer" used herein refers to a single layer and / or a plurality of layers between a first electrode and a second electrode of an organic light emitting device. In addition to organic compounds, the "organic layer" may further include an organic metal complex including a metal.

[0394] 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 of an organic light emitting device according to an embodiment and a method of manufacturing the organic light emitting device according to an embodiment 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.

[0395] A substrate may be additionally provided below the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate used in an organic light-emitting device available in the art may be used, and the substrate may be a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0396] In one or more embodiments, the first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be a material having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (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).

[0397] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more 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.

[0398] The organic layer 15 is located on the first electrode 11 .

[0399] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0400] The hole transport region may be between the first electrode 11 and the emission layer.

[0401] The hole transport region may include at least one selected from a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.

[0402] 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 or a hole injection layer / hole transport layer / electron blocking layer structure, wherein for each structure, each layer is sequentially stacked in the order stated starting from the first electrode 11.

[0403] When the hole transport region includes a hole injection layer (HIL), the HIL 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.

[0404] 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 of about 100° C. to about 500° C., a ... 8 -About 10- 3 Torr vacuum pressure, and about Seconds - Approx. The deposition rate is 2000 s. However, the deposition conditions are not limited thereto.

[0405] When the hole injection layer is formed using spin coating, the coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, the coating speed may be about 2,000 rpm to about 5,000 rpm, and the temperature of heat treatment to remove the solvent after coating may be about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

[0406] The conditions for forming the hole transport layer and the electron blocking layer can be understood by referring to the conditions for forming the hole injection layer.

[0407] The hole transport region may include at least one selected from 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:

[0408]

[0409]

[0410] Formula 201

[0411]

[0412] Formula 202

[0413]

[0414] Ar in Formula 201 101 -Ar 102 Can be independently:

[0415] 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, perylenene, pentphenylene, or any combination thereof; or

[0416] Each of the following is selected from at least one substituted phenylene, pentalene, indenylene, naphthylene, azulenylene, heptalene, acenaphthene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, acenaphthene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, acenaphthene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, acenaphthene, fluorenylene, phenanthrenylene, phenanthrenylene, fluorenylene, benzo[9,10]phenanthrenylene, py ... phenylene, tetraphenylene, perylene, perylene, pentphenylene, or any combination thereof: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group 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 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 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.

[0417] 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.

[0418] R in formula 201 and 202 101 -R 108 , R 111 -R 119 and R 121 -R 124 Can be independently:

[0419] 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, hexyl, etc.), C 1 -C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.), or any combination thereof;

[0420] Each of the following is substituted by at least one C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, or any combination thereof: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, and phosphoric acid group or its salt;

[0421] Phenyl, naphthyl, anthracenyl, fluorenyl, pyrenyl, or any combination thereof; or

[0422] Each of the phenyl, naphthyl, anthracenyl, fluorenyl, pyrenyl, or any combination thereof is selected from at least one substituted group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C 1 -C 10 Alkyl, and C 1 -C 10 Alkoxy group, but the embodiments of the present disclosure are not limited thereto.

[0423] R in Formula 201 109 Can be:

[0424] phenyl, naphthyl, anthracenyl, or pyridyl; or

[0425] each being selected from at least one substituted phenyl, naphthyl, anthracenyl, or pyridyl group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, naphthyl, anthracenyl, and pyridyl.

[0426] According to one 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:

[0427] Formula 201A

[0428]

[0429] R in Formula 201A 101 , R 111 , R 112 and R 109 This can be understood by referring to the description provided herein.

[0430] 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:

[0431]

[0432]

[0433] The thickness of the hole transport region may be about about For example, about 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 about For example, about about In the range of, and the thickness of the hole transport layer may be about about For example, about 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.

[0434] In addition to these materials, the hole transport region may further include a charge generating material for improving conductive properties. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0435] The charge generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano-containing compound, 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 cyano-containing compounds such as the following compound HT-D1 or compound HT-D2, but are not limited thereto.

[0436]

[0437] The hole transport region may include a buffer layer.

[0438] Also, 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.

[0439] The hole transport region may further include an electron blocking layer. The electron blocking layer may include a material available in the art, such as mCP, but the embodiments of the present disclosure are not limited thereto.

[0440]

[0441] The thickness of the electron blocking layer may be about to about For example, about to about When the thickness of the electron blocking layer is within the above range, the electron blocking layer may have satisfactory electron blocking characteristics without a significant increase in driving voltage.

[0442] Then, an emission layer (EML) 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, although the deposition or coating conditions may vary depending on the material used to form the emission layer, the deposition or coating conditions may be similar to those applied when forming the hole injection layer.

[0443] When the organic light emitting device 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, due to the stacked structure including the red emission layer, the green emission layer, and / or the blue emission layer, the emission layer may emit white light.

[0444] The emission layer may include a heterocyclic compound represented by Formula 1.

[0445] For example, the emission layer may include the heterocyclic compound represented by Formula 1 only.

[0446] In one or more embodiments, the emission layer may include a heterocyclic compound represented by Formula 1, and may further include: i) a second compound (e.g., a compound different from the heterocyclic compound represented by Formula 1); ii) an organic metal compound represented by Formula 81; or iii) any combination thereof.

[0447] The heterocyclic compound represented by Formula 1, the second compound, and the organometallic compound represented by Formula 81 may each be the same as described above.

[0448] When the emission layer includes a host and a dopant, the amount of the dopant may be in the range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the emission layer. However, the amount of the dopant included in the emission layer is not limited thereto. When the amount of the dopant satisfies this range, it may be possible to achieve emission without quenching.

[0449] When the emission layer includes the heterocyclic compound represented by Formula 1 and the second compound, the weight ratio of the heterocyclic compound represented by Formula 1 to the second compound may be in the range of about 1:99 to about 99:1, for example, about 70:30 to about 30:70. In one or more embodiments, the weight ratio of the heterocyclic compound represented by Formula 1 to the second compound may be in the range of about 60:40 to about 40:60. When the weight ratio of the heterocyclic compound represented by Formula 1 to the second compound in the emission layer is within this range, charge transfer balance in the emission layer may be effectively performed.

[0450] The thickness of the emission layer may be about about For example, about about When the thickness of the emission layer is within this range, excellent light emitting characteristics can be obtained without a significant increase in driving voltage.

[0451] Then, an electron transport region may be located on the emissive layer.

[0452] The electron transport region may include at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

[0453] 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.

[0454] 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.

[0455] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP and Bphen, but embodiments of the present disclosure are not limited thereto.

[0456]

[0457] In one or more embodiments, the hole blocking layer may include a heterocyclic compound represented by Formula 1.

[0458] The thickness of the hole blocking layer may be about about For example, about about When the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking properties without a significant increase in driving voltage.

[0459] The electron transport layer may further include BCP, Bphen, Alq 3 , BAlq, TAZ, and NTAZ.

[0460]

[0461] In one or more embodiments, the electron transport layer may include at least one selected from ET1, ET2 and ET3, but is not limited thereto:

[0462]

[0463] The thickness of the electron transport layer may be about about For example, about about When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a significant increase in driving voltage.

[0464] Also, the electron transport layer may further include a material including a metal in addition to the materials described above.

[0465] 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:

[0466]

[0467] The electron transport region may include an electron injection layer (EIL) that facilitates the flow of electrons from the second electrode 19 therein.

[0468] The electron injection layer may include a material selected from LiQ, LiF, NaCl, CsF, Li 2 At least one of O and BaO.

[0469] The thickness of the electron injection layer can be about about and for example about about When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a significant increase in driving voltage.

[0470] 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 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.

[0471] In the foregoing, the organic light emitting device has been described with reference to the accompanying drawings, but the embodiments of the present disclosure are not limited thereto.

[0472] According to one embodiment, an electronic device is provided, which includes a substrate and an organic light-emitting device on the substrate. The organic light-emitting device is the same as described above.

[0473] According to one embodiment, the electronic device may further include a color conversion layer,

[0474] The color conversion layer may be located in at least one propagation direction of light emitted from the organic light emitting device, and may include quantum dots.

[0475] The quantum dots are particles having a crystal structure of several nanometers to several tens of nanometers and include hundreds to thousands of atoms.

[0476] Since quantum dots are very small in size, a quantum confinement effect may occur. The quantum confinement effect refers to a phenomenon in which the band gap of an object becomes larger when the object becomes smaller than a nanometer size. Therefore, when light having a wavelength having an energy intensity greater than the band gap of a quantum dot is irradiated to the quantum dot, the quantum dot is excited by absorbing the light and emits light having a specific wavelength and transitions to a ground state. In this case, the wavelength of the emitted light has a value corresponding to the band gap.

[0477] The quantum dots may be semiconductor materials. For example, the quantum dots may include II-VI semiconductor compounds, III-V semiconductor compounds, IV-VI semiconductor compounds, IV elements or compounds, or combinations thereof. The II-VI semiconductor compound may be, for example, a binary compound, which may be CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, or a combination thereof; a ternary compound, which may be CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, or a combination thereof; or a quaternary compound, which may be CdHgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, or a combination thereof. The III-V semiconductor compound may be, for example, a binary compound, which may be GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, or a combination thereof; a ternary compound, which may be GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, or a combination thereof; or a quaternary compound, which may be GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, or a combination thereof. The IV-VI semiconductor compound may be, for example, a binary compound such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, or a combination thereof; a ternary compound such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, or a combination thereof; or a quaternary compound such as SnPbSSe, SnPbSeTe, SnPbSTe, or a combination thereof. The IV group element or compound may be, for example, Si, Ge, SiC, SiGe, or a combination thereof.

[0478] The quantum dot may have a core structure or a core-shell structure, or a core-shell-shell structure. Depending on the constituent materials, the quantum dot core may have a diameter of about 1 nm to several tens of nm. The quantum dot core-shell structure may be, for example, a CdSe / CdS structure or an InP / ZnS structure. The quantum dot core-shell-shell structure may be, for example, a CdSe / CdS / ZnS structure.

[0479] The quantum dots can adjust the color of the emitted light according to the particle size. Therefore, the quantum dots can emit a variety of emission colors such as blue, red or green.

[0480] In addition, the shape of the quantum dots is not particularly limited. For example, the quantum dots may be spherical, cubic, pyramidal, or multi-armed nanoparticles. In one or more embodiments, the quantum dots may have the form of nanotubes, nanowires, nanofibers, nanosheet particles, etc.

[0481] 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.

[0482] The term "C 1 -C 60 "Alkoxy" refers to a 101 (A 101 C 1 -C 60 An alkyl group is a monovalent group represented by an alkyl group, and examples thereof include a methoxy group, an ethoxy group and an isopropoxy group.

[0483] 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.

[0484] 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 into the middle or 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.

[0485] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon 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.

[0486] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent saturated monocyclic group having at least one selected from N, O, P, Si, B, Se, Ge, Te and S as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a group having a C 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0487] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0488] As used herein, the term "C 2 -C 10The term "heterocycloalkenyl" refers to a monovalent monocyclic group having at least one selected from N, O, P, Si, B, Se, Ge, Te and S as a ring atom, 2 to 10 carbon atoms, and at least one (e.g., carbon-carbon) double bond in its ring. 2 -C 10 Examples of heterocycloalkenyl are 2,3-dihydrofuranyl and 2,3-dihydrothienyl. 2 -C 10 "Heterocycloalkenylene" refers to a 2 -C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0489] 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. 7 -C 60 Alkaryl refers to a group consisting of at least one C 1 -C 60 Alkyl substituted C 6 -C 60 Aryl.

[0490] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si, B, Se, Ge, Te 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 a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, B, Se, Ge, Te 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.6 -C 60 Heteroaryl and C 6 -C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other. 2 -C 60 Alkylheteroaryl refers to a 1 -C 59 Alkyl substituted C 1 -C 59 Heteroaryl.

[0491] 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).

[0492] 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.

[0493] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 2-60 carbon atoms) having two or more rings fused to each other, having at least one heteroatom selected from N, O, P, Si, B, Se, Ge, Te and S as a ring-forming atom 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.

[0494] 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 -C30 The carbocyclic group may be a monocyclic group or a polycyclic group.

[0495] 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, B, Se, Ge, Te and S as a ring atom. 1 -C 30 The heterocyclic group may be a monocyclic group or a polycyclic group.

[0496] 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 Alkaryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 At least one substituent of the alkylheteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is:

[0497] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2, hydroxyl, cyano, nitro, 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, or any combination thereof;

[0498] Each of the following is substituted by at least one C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or any combination thereof: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, 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 7 -C 60 Alkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 alkylheteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17), and -P(=O)(Q 18 )(Q 19 );

[0499] 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, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 an alkylheteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof;

[0500] Each of the following is substituted by at least one 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, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, or any combination thereof: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2, hydroxyl, cyano, nitro, 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 7 -C 60 Alkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 alkylheteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ), and -P(=O)(Q 28 )(Q 29 );or

[0501] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 ), or any combination thereof,

[0502] Where Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q29 , and Q 31 -Q 39 can each independently be 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, C 1 -C 60 Alkyl, selected from deuterium, C 1 -C 60 Alkyl, and C 6 -C 60 At least one 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, C 6 -C 60 Aryl, selected from deuterium, C 1 -C 60 Alkyl, and C 6 -C 60 At least one substituted C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 an alkylheteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof.

[0503] Hereinafter, the compound and the organic light-emitting device according to the embodiment will be 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 in terms of molar equivalents, the amount of 'A' used is the same as the amount of 'B' used.

[0504] Example

[0505] Synthesis Example 1: Synthesis of Compound 1

[0506] Compound 1 was synthesized according to the following reaction scheme.

[0507]

[0508] 3,6-Diiododibenzofuran (5 g, 11.9 mmol), (10-phenylanthracen-9-yl)boronic acid (7.8 g, 26.2 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4 , 2.8 g, 2.4 mmol), and tripotassium phosphate (K 3 PO 4 , 15.2g, 71.4mmol) was added to 50ml toluene, 12ml ethanol and 12ml distilled water, and the mixture was refluxed. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was extracted with toluene, and anhydrous sodium sulfate (Na 2 SO 4 ) was dried and filtered using a silica filter. The filtrate was concentrated and recrystallized with toluene and ethyl acetate to obtain compound 1. (3.8 g, 5.6 mmol, yield 47%)

[0509] LCMS (calculated value: 672.25, found value (M+1): 673.245 m / z)

[0510] Synthesis Example 2: Synthesis of Compound 113

[0511] Compound 113 was synthesized using the same method as in Synthesis Example 1, except that 6-bromo-2-iododibenzofuran was used instead of 3,6-diiododibenzofuran when compound 1 was synthesized. (45% yield)

[0512] LCMS (calculated value: 672.25, found value (M+1): 673.245 m / z)

[0513] Synthesis Example 3: Synthesis of Compound 134

[0514] Compound 134 was synthesized in the same manner as used in Synthesis Example 1, except that when compound 1 was synthesized, 6-bromo-2-iododibenzofuran was used instead of 3,6-diiododibenzofuran, and 2-(10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene-9-yl)benzonitrile was used instead of (10-phenylanthracene-9-yl)boronic acid. (35% yield)

[0515] LCMS (calculated value: 722.24, found value (M+1): 723.241 m / z)

[0516] Synthesis Example 4: Synthesis of Compound 171

[0517] Compound 171 was synthesized according to the following reaction scheme.

[0518]

[0519] (1) Synthesis of intermediate (1)

[0520] 6-Bromo-2-iododibenzofuran (10 g, 26.8 mmol), (10-phenylanthracen-9-yl)boronic acid (8.8 g, 29.5 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4 , 6.2 g, 5.4 mmol), and potassium carbonate (K 2 CO 3 , 11.1 g, 80.4 mmol) was added to 120 ml of tetrahydrofuran (THF) and 40 ml of distilled water, and the mixture was refluxed. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was extracted with toluene, and anhydrous sodium sulfate (Na 2 SO 4 ) was dried and concentrated, and subjected to silica gel column chromatography, thereby obtaining Intermediate 1. (7.3 g, 14.6 mmol, yield 55%)

[0521] (2) Synthesis of Compound 171

[0522] Compound 171 was synthesized using the same method as in Synthesis Example 1, except that when synthesizing Compound 1, Intermediate 1 was used instead of 3,6-diiododibenzofuran, and 1.2 equivalents of 10-(1-naphthyl)anthracene-9-boronic acid was used instead of (10-phenylanthracene-9-yl)boronic acid. (52% yield)

[0523] LCMS (calculated value: 722.26, found value (M+1): 723.257 m / z)

[0524] Synthesis Example 5: Synthesis of Compound 1121

[0525] Compound 1121 was synthesized using the same method as in Synthesis Example 1, except that 6-bromo-2-iododibenzoselenophene was used instead of 3,6-diiododibenzofuran when compound 1 was synthesized. (38% yield)

[0526] LCMS (calculated value: 736.17, found value (M+1): 737.155 m / z)

[0527] Synthesis Example 6: Synthesis of Compound 2102

[0528] Compound 2102 was synthesized using the same method as in Synthesis Example 1, except that when compound 1 was synthesized, 6-bromo-2-iododibenzofuran was used instead of 3,6-diiododibenzofuran, and (10-butylanthracen-9-yl)boric acid was used instead of (10-phenylanthracen-9-yl)boric acid. (46% yield)

[0529] LCMS (calculated value: 632.31, found value (M+1): 633.307 m / z)

[0530] Synthesis Example 7: Synthesis of Compound A

[0531] Compound A was synthesized using the same method as in Synthesis Example 1, except that 2,8-dibromodibenzofuran was used instead of 3,6-diiododibenzofuran when compound 1 was synthesized. (43% yield)

[0532] LCMS (calculated value: 672.25, found value (M+1): 673.245 m / z)

[0533] Synthesis Example 8: Synthesis of Compound B

[0534] Compound B was synthesized using the same method as in Synthesis Example 1, except that 6-bromo-2-iododibenzothiophene was used instead of 3,6-diiododibenzofuran when compound 1 was synthesized. (41% yield)

[0535] LCMS (calculated value: 688.22, found value (M+1): 689.167 m / z)

[0536] Example 1

[0537] The patterned ITO glass substrate (50 mm×50 mm×0.7 mm) was ultrasonically cleaned in acetone, isopropyl alcohol, and distilled water for 20 minutes each, and then heat-treated at a temperature of 250° C. for 10 minutes.

[0538] Then, HATCN The deposition rate of 10000 s was deposited on the ITO electrode (anode) on the glass substrate to form a The hole injection layer is formed by adding NPB sec deposition rate is deposited on the hole injection layer to form a The hole transport layer has a thickness of .

[0539] Then, mCP sec deposition rate is deposited on the hole transport layer to form a The thickness of the electron blocking layer is .

[0540] Compound 1 (host) and compound D1 (dopant) were prepared by Seconds and The deposition rate of 2.5 sec is co-deposited on the electron blocking layer to form a The thickness of the emission layer.

[0541] DPEPO and LiQ (in a 1:1 ratio) were mixed with The deposition rate of 1000 s is co-deposited on the emission layer to form a The thickness of the electron transport layer is then LiQ The deposition rate of 1000 s is deposited on the electron transport layer to form a Then, Al is vacuum deposited on the electron injection layer to form a The second electrode (cathode) with a thickness of ITO / HATCN ( ) / NPB( ) / mCP( ) / Compound 1+Compound D1(3%) ( ) / DPEPO:LiQ( ) / LiQ( ) / Al( ) structure of an organic light-emitting device.

[0542]

[0543] Examples 2-5 and Comparative Examples 1-2

[0544] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 2 were each used as a host instead of Compound 1 in forming the emission layer.

[0545] Evaluation Example 1: Characterization of organic light-emitting devices

[0546] For each of the organic light emitting devices manufactured according to Examples 1-5 and Comparative Examples 1-2, the photoluminescence quantum efficiency (PLQY), external quantum efficiency (EQE), TTF ratio and lifetime (T 95 ) was evaluated as a relative value. The results are shown in Table 2. The evaluation was performed using a current-voltage meter (Keithley 2400) and a brightness meter (Minolta Cs-1,000A), and the lifespan (T 95The TTF ratio was obtained by measuring the decay of transient electroluminescence (TrEL) to obtain a plot of 1 / (square root of TrEL intensity from 500ns to 4000ns) (1 / sqrt(TrEL)) versus time, and then taking the square of the inverse of the y-intercept value in the plot.

[0547] Table 2

[0548]

[0549]

[0550]

[0551] Table 2 shows that the organic light-emitting devices of Examples 1-5 have excellent external quantum efficiency and lifetime characteristics and high TTF ratio. In addition, compared with the organic light-emitting devices of Comparative Examples 1 and 2, the organic light-emitting devices of Examples 1-5 show better lifetime characteristics and higher TTF ratio.

[0552] As described above, the heterocyclic compound according to the embodiment of the present disclosure has excellent electrical characteristics and thermal stability. Therefore, an organic light-emitting device using the heterocyclic compound may have high efficiency, long lifespan, and high TTF ratio.

[0553] 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 one of Formulas 1-1 and 1-2 and having an asymmetric structure: in, In Formulas 1-1, 1-2, 1A-5 and 2A-5, X1 in Formula 1-1 is O, and X1 in Formula 1-2 is O or Se, Ar1 is represented by formula 1A-5, and Ar2 is represented by formula 2A-5, L1 and L2 are each independently substituted or unsubstituted C5-C 30 Carbocyclic group, substituted or unsubstituted C1-C 30 Heterocyclic group, or any combination thereof, a1 and a2 are each independently 0, R1 and R2 are each independently: C1-C 20 Alkyl or C1-C 20 Alkoxy; Each of the following C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, and cyano; Phenyl or naphthyl; Each of the phenyl or naphthyl groups is selected from at least one substituted group consisting of deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, and C1-C 20 Alkoxy; or A group represented by one of formulae 10-63 to 10-65: Where Ph is phenyl, R 11 -R 14 , R 16 -R 19 , R 21 -R 24 , R 26 -R 29 , R 32 -R 34 , and R 41 -R 44 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, or C1-C 20 Alkoxy; or Each of the following C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, and cyano, and b1 and b2 are each independently 1.

2. The heterocyclic compound according to claim 1, wherein R1 and R2 are each independently a group represented by one of formulas 9-1 to 9-19, or a group represented by one of formulas 10-13 to 10-41, 10-49 to 10-62, 10-70 to 10-72, 10-81, 10-82 and 10-156: in, In Formulae 9-1 to 9-19, 10-13 to 10-41, 10-49 to 10-62, 10-70 to 10-72, 10-81, 10-82 and 10-156, * represents a binding site with an adjacent atom.

3. The heterocyclic compound as claimed in claim 1, wherein R 11 -R 14 , R 16 -R 19 , R 21 -R 24 , R 26 -R 29 , R 32 -R 34 and R 41 -R 44 Each independently is: Hydrogen, deuterium, cyano, C1-C 20 Alkyl, or C1-C 20 Alkoxy; or C1-C ... 20 Alkyl or C1-C 20 Alkoxy.

4. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by Formula 1-1 is a compound represented by Formula 10-1, and the heterocyclic compound represented by Formula 1-2 is a compound represented by Formula 10-2: in, In equations 10-1 and 10-2, X1, L1, L2, a1, a2, R1, R2, b1 and b2 are the same as described with respect to claim 1.

5. The heterocyclic compound as claimed in claim 1, wherein the heterocyclic compound represented by one of Formulas 1-1 and 1-2 satisfies Equation 1: Equation 1 E(T1) <E(S1)<2×E(T1) Among them, In equation 1, E(T1) represents the lowest excited triplet energy level of the heterocyclic compound and E(S1) represents the lowest excited singlet energy level of the heterocyclic compound.

6. The heterocyclic compound as claimed in claim 1, wherein the heterocyclic compound represented by one of Formulas 1-1 and 1-2 satisfies Equation 2: Equation 2 [2×E(T1)]-E(S1)<0.5eV in, In equation 2, E(T1) represents the lowest excited triplet energy level of the heterocyclic compound and E(S1) represents the lowest excited singlet energy level of the heterocyclic compound.

7. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by one of Formulas 1-1 and 1-2 is one of the following compounds:

8. Organic light-emitting device, comprising: a first electrode; a second electrode; as well as an organic layer located between the first electrode and the second electrode and including an emission layer, The organic layer comprises at least one heterocyclic compound represented by one of Formulae 1-1 and 1-2 as claimed in any one of claims 1 to 7.

9. The organic light emitting device according to claim 8, wherein The first electrode is an anode and the second electrode is a cathode, The organic layer includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, wherein the hole transport region comprises at least one selected from a hole injection layer, a hole transport layer and an electron blocking layer, and The electron transport region includes at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer. 10 . The organic light emitting device of claim 9 , wherein a heterocyclic compound represented by one of Formulae 1-1 and 1-2 is included in the emission layer.

11. The organic light emitting device of claim 10, wherein the emission layer comprises a host and a dopant, The host includes a heterocyclic compound represented by one of Formulae 1-1 and 1-2, and an amount of the host is greater than an amount of the dopant. 12 . The organic light emitting device of claim 11 , wherein the dopant is a fluorescent dopant or a phosphorescent dopant. 13 . The organic light emitting device of claim 10 , wherein the emission layer emits light having a maximum emission wavelength of about 410 nm to about 490 nm. 14 . The organic light emitting device of claim 9 , wherein a heterocyclic compound represented by one of Formulae 1-1 and 1-2 is included in the hole transport region. 15 . The organic light emitting device of claim 9 , wherein a heterocyclic compound represented by one of Formulae 1-1 and 1-2 is included in the electron transport region.

Images