Amine compound and organic light-emitting device comprising the same

Abstract

An amine compound and an organic light-emitting device including the same are provided, wherein the amine compound is represented by Formula 1. The description of the substituents and parameters in Formula 1 are the same as those provided in the detailed description. Formula 1

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application is based on and claims the benefit of priority from Korean Patent Application No. 10-2020-0102053 filed in the Korean Intellectual Property Office on August 13, 2020, the disclosure of which is incorporated herein in its entirety by reference. Technical Field

[0003] One or more embodiments relate to an amine 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 located between the anode and the emission layer, and an electron transport region may be located 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 include an amine 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 provided embodiments of the disclosure.

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

[0009] Formula 1

[0010]

[0011] Among them, in formula 1,

[0012] R 1 -R 8 are 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 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -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 C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 )、-B(Q 6 )(Q 7 ), or -P(=O)(Q 8 )(Q 9 ),

[0013] R 11 -R 14 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, 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 1 -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 C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 ), or -P(=O)(Q 8 )(Q 9 ),

[0014] R 21 -R 24 are 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 1 -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 60Heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 ), or -P(=O)(Q 8 )(Q 9 ),

[0015] b11-b14 are each independently an integer of 1-4,

[0016] b21-b24 are each independently an integer of 1-5,

[0017] 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 1 -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 Heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:

[0018] Deuterium, -F, -Cl, -Br, -I, -CD3 、-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;

[0019] Each of the following 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 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11)(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 ), or any combination thereof;

[0020] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof;

[0021] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -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, 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 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ), or any combination thereof; or

[0022] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 ), or any combination thereof,

[0023] Where Q 1 -Q 9 , Q 11 -Q 17 , Q 21 -Q 27 , and Q 31 -Q 37are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, 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 1 -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 C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0024] Another aspect provides an organic light emitting device including a first electrode; a second electrode; and an organic layer including an emission layer between the first electrode and the second electrode, wherein the organic layer includes at least one of the organic metal compounds. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] The above and other aspects, features, and advantages of some embodiments of the present disclosure will become more apparent from the following description considered in conjunction with the accompanying drawings, in which:

[0026] Figure 1 A schematic cross-sectional view of an organic light emitting device according to an exemplary embodiment is shown. DETAILED DESCRIPTION

[0027] 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.

[0028] 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.

[0029] 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.

[0030] The terms used herein are only used for the purpose of describing specific embodiments and are not intended to be limiting. As used herein, "a (kind) (indefinite article) (a, an)", "said (the)" and "at least one (kind)" do not represent the limitation of quantity and are intended to cover both the singular and the plural, unless the context clearly indicates otherwise. For example, "(an) element (anelement)" has the same meaning as "at least one element", unless the context clearly indicates otherwise.

[0031] "Or" means "and / or". It will be further understood that the terms "comprise" or "include" when used in this specification indicate the presence of 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 combinations thereof.

[0032] 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 drawings, relative terms are also intended to cover different orientations of the device. For example, if the device in one of the figures is turned over, the element described as being on the "lower" side of the other element will be oriented on the "upper" side of the other element. Therefore, depending on the specific orientation of the figure, the exemplary term "lower" can cover both "lower" and "upper" orientations. Similarly, if the device in one of the drawings is turned over, the element described as "below" or "below" the other element will be oriented "above" the other element. Therefore, the exemplary terms "below..." or "below..." can cover both "above..." and "below..." orientations.

[0033] 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 within one or more standard deviations, or within ±10% or 5% relative to the stated value.

[0034] 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.

[0035] 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 accompanying drawings 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.

[0036] In an embodiment, an amine compound represented by Formula 1 is provided:

[0037] Formula 1

[0038]

[0039] R in Formula 1 1 -R 8 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 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -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 C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 )、-B(Q 6 )(Q 7 ), or -P(=O)(Q 8 )(Q 9 ).

[0040] In an embodiment, R 1 -R 8 Can be independently:

[0041] hydrogen, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, pentalenyl, indenyl, naphthyl, 1-Heptenyl, ... 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, triazinyl, dibenzofuranyl, dibenzothiophenyl, imidazopyrimidinyl, or imidazopyridinyl; or

[0042] cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, pentalenyl, indenyl, naphthyl, 1-Heptenyl, ... 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, triazine, dibenzofuranyl, dibenzothiophenyl, imidazopyrimidinyl, or imidazopyridinyl: 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 2 -C 20 Alkenyl, C 2 -C 20 Alkynyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, phthalazinyl, quinoxalinyl, cinnolinyl, quinazolinyl, or any combination thereof.

[0043] In an embodiment, R1 -R 8 Can be independently:

[0044] hydrogen, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl; or

[0045] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl, each substituted with at least one of the following: deuterium, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, or any combination thereof.

[0046] In an embodiment, R 1 -R 8 Each may be hydrogen.

[0047] R in Formula 1 11 -R 14 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, 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 1 -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 C 1 -C 60Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 )、-B(Q 6 )(Q 7 ), or -P(=O)(Q 8 )(Q 9 ).

[0048] In an embodiment, R 11 -R 14 Can be independently:

[0049] Hydrogen, C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy;

[0050] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or any combination thereof;

[0051] Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, pentalenyl, indenyl, naphthyl, 1-Heptenyl, ... 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, triazinyl, dibenzofuranyl, dibenzothiophenyl, imidazopyrimidinyl, or imidazopyridinyl; or

[0052] cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, pentalenyl, indenyl, naphthyl, 1-Heptenyl, ... 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, or imidazopyridinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, 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, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, phthalazinyl, quinoxalinyl, cinnolinyl, quinazolinyl, or any combination thereof.

[0053] In an embodiment, R 11 -R 14 Can be independently:

[0054] Hydrogen, C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy;

[0055] Each of the following C 1 -C 20 Alkyl or C 1 -C 20Alkoxy: 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, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or any combination thereof;

[0056] Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, pentalenyl, indenyl, naphthyl, 1-Heptenyl, ... 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

[0057] cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, pentalenyl, indenyl, naphthyl, 1-Heptenyl, ... 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, triazine, dibenzofuranyl, dibenzothiophenyl, imidazopyrimidinyl, or imidazopyridinyl: 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 2 -C 20 Alkenyl, C 2 -C 20 Alkynyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, phthalazinyl, quinoxalinyl, cinnolinyl, quinazolinyl, or any combination thereof.

[0058] In an embodiment, R 11 -R 14 Can be independently:

[0059] Hydrogen, C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy;

[0060] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, phenyl, biphenyl, terphenyl, naphthyl, or any combination thereof;

[0061] cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl; or

[0062] cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl, each substituted with at least one of: deuterium, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, or any combination thereof.

[0063] In an embodiment, R 11 -R 14 Each may not be a cyano group.

[0064] In an embodiment, R 11 -R 14Each may be hydrogen.

[0065] b11-b14 in Formula 1 may each independently be an integer of 1-4. When b11 is 2 or greater, R 11 Two or more of may be the same as or different from each other. When b12 is 2 or greater, R 12 Two or more of may be the same or different from each other. When b13 is 2 or greater, R 13 Two or more of may be the same as or different from each other. When b14 is 2 or greater, R 14 Two or more of may be the same as or different from each other.

[0066] In an embodiment, when R 11 -R 14 When each is not hydrogen, b11-b14 may each independently be 1, 2, 3, or 4.

[0067] In an embodiment, when R 11 -R 14 When each is not hydrogen, b11-b14 may each independently be 1 or 2.

[0068] In an embodiment, when R 11 -R 14 When each is not hydrogen, b11-b14 may each be 1.

[0069] R in Formula 1 21 -R 24 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 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 ), or -P(=O)(Q 8 )(Q 9 ).

[0070] In an embodiment, R 21 -R 24 Can be independently:

[0071] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF 5 , C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy;

[0072] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof;

[0073] 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, or imidazopyrimidinyl;

[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, Oxazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl: 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, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or any combination thereof; or

[0075] -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 ), or -P(=O)(Q 8 )(Q 9 ),

[0076] Where Q 1 -Q 9 Can be independently:

[0077] -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 2H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CH 3 、-CD 2 CD 3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;

[0078] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0079] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of: deuterium, C 1 -C 10 Alkyl, phenyl, or any combination thereof.

[0080] In an embodiment, R 21 -R 24 can each independently be 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, or C 1 -C 20 Alkoxy;

[0081] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or any combination thereof;

[0082] Cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, pentalenyl, indenyl, naphthyl, 1-Heptenyl, ... 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, triazinyl, dibenzofuranyl, dibenzothiophenyl, imidazopyrimidinyl, or imidazopyridinyl; or

[0083] cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, pentalenyl, indenyl, naphthyl, 1-Heptenyl, ... 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, triazine, dibenzofuranyl, dibenzothiophenyl, imidazopyrimidinyl, or imidazopyridinyl: 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 2 -C 20 Alkenyl, C 2 -C 20 Alkynyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, phthalazinyl, quinoxalinyl, cinnolinyl, quinazolinyl, or any combination thereof.

[0084] In an embodiment, R21 -R 24 Each independently may be hydrogen, deuterium, -F, cyano, a group represented by one of formulae 9-1 to 9-19, or a group represented by one of formulae 10-1 to 10-195:

[0085]

[0086]

[0087]

[0088]

[0089]

[0090] Wherein, in Formulae 9-1 to 9-19 and 10-1 to 10-195, * represents a bonding site with an adjacent atom, Ph may be a phenyl group, and TMS may be a trimethylsilyl group.

[0091] In an embodiment, R 21 -R 24 can be independently hydrogen, deuterium, cyano, C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy;

[0092] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, cyano, phenyl, biphenyl, terphenyl, naphthyl, or any combination thereof;

[0093] cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl; or

[0094] cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl, each substituted with at least one of the following: deuterium, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, or any combination thereof.

[0095] In an embodiment, R 21 -R 24 Can be independently C 1-C 20 Alkyl or C 1 -C 20 Alkoxy;

[0096] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, cyano, phenyl, biphenyl, terphenyl, naphthyl, or any combination thereof;

[0097] cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl; or

[0098] cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl, each substituted with at least one of the following: deuterium, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, or any combination thereof.

[0099] In an embodiment, R 21 -R 24 Each may not be a cyano group.

[0100] In an embodiment, R 21 -R 24 Each may be hydrogen.

[0101] b21-b24 in Formula 1 may each be an integer of 1-5. When b21 is 2 or greater, R 21 Two or more of may be the same or different from each other. When b22 is 2 or greater, R 22 Two or more of may be the same or different from each other. When b23 is 2 or greater, R 23 Two or more of may be the same or different from each other. When b24 is 2 or greater, R 24 Two or more of may be the same as or different from each other.

[0102] In an embodiment, when R 21 -R 24 When each is not hydrogen, b21-b24 may each independently be 1, 2, 3, or 4.

[0103] In an embodiment, when R 21 -R 24 When each is not hydrogen, b21-b24 may each independently be 1, 2, or 3.

[0104] In an embodiment, when R 21 -R 24 When each is not hydrogen, b21-b24 may each independently be 1 or 2.

[0105] In an embodiment, when R 21 -R 24 When each is not hydrogen, b21-b24 may each independently be 1.

[0106] 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 1 -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 Heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

[0107] 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 60Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or any combination thereof;

[0108] Each of the following 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 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 ), or any combination thereof;

[0109] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof;

[0110] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, 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, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ), or any combination thereof; or

[0111] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 ), or any combination thereof,

[0112] Where Q 1 -Q 9 , 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 C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C60 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 1 -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 C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0113] In an embodiment, the amine compound may be represented by Formula 2:

[0114] Formula 2

[0115]

[0116] Among them, in formula 2,

[0117] R 1 -R 8 Same as described above,

[0118] R 31 , R 32 , R 38 , R 39 , R 41 , R 47 , R 48 , R 49 , R 51 , R 52 , R 58 , R 59 , R 61 , R 67 , R 68 , and R 69 Each independently and with respect to R 11 -R 14 Same as described, and

[0119] R 33 -R 37 , R 42 -R 46 , R 53 -R 57 and R 62 -R 66 Each independently and with respect to R 21 -R 24 Same as described.

[0120] In an embodiment, the amine compound may be one of compounds 1 to 26:

[0121]

[0122]

[0123]

[0124]

[0125] The amine compound represented by Formula 1 satisfies the structure of Formula 1 as described above, and due to a diamine structure including two amine groups substituted by groups including m-biphenyl and p-biphenyl, the amine compound may have singlet and triplet energy levels and highest occupied molecular orbital (HOMO) / lowest unoccupied molecular orbital (LUMO) energy levels suitable for use in organic light-emitting devices.

[0126] As described above, the amine compound represented by Formula 1 may have electrical properties suitable for use as a material for an organic light-emitting device, such as a host material and a dopant material in an emission layer, a hole transport material, an electron transport material, etc. Therefore, an organic light-emitting device using the amine compound may have high efficiency and / or a long lifespan.

[0127] In the amine compound represented by Formula 1, R 1 -R 8 Each is not an alkyl group. Although not limited by a particular theory, when R 1 -R 8 When at least one of is an alkyl group, for example, in the case of compound A, due to the alkyl substituent located at the central core, the energy transfer efficiency is reduced and the photo-orientation is deteriorated. Therefore, the organic light-emitting device using compound A may have lower efficiency and / or shorter lifespan than the organic light-emitting device using the amine compound.

[0128] <Compound A>

[0129]

[0130] In the amine compound represented by Formula 1, R 11 -R 14 Each is not cyano. Although not limited by a particular theory, when R 11 -R 14 When at least one of the amine compounds is a cyano group, for example, in the case of compound B, the HOMO energy level is relatively high (i.e., the absolute value of the HOMO energy level is small) due to the electron-withdrawing property of the cyano group. Therefore, the organic light-emitting device using compound B may have lower energy transfer efficiency in the emission layer than the organic light-emitting device using the amine compound.

[0131] <Compound B>

[0132]

[0133] Those skilled in the art may recognize a method of synthesizing the amine compound represented by Formula 1 by referring to Synthesis Examples which will be described later.

[0134] The amine compound represented by Formula 1 can be suitable for use as a material for the following: an organic layer of an organic light-emitting device, such as an emission layer, a hole transport region, and / or an electron transport region in the organic layer. Therefore, another aspect provides an organic light-emitting device, which includes a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode and including the emission layer, wherein the organic layer includes at least one amine compound represented by Formula 1.

[0135] Due to including the organic layer including the amine compound represented by Formula 1 above, the organic light emitting device may have low driving voltage, high efficiency, high brightness, high quantum luminous efficiency, and long lifespan.

[0136] In one embodiment, in the organic light-emitting device,

[0137] The first electrode is an anode and the second electrode is a cathode,

[0138] 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

[0139] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and

[0140] 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.

[0141] In an embodiment, the emission layer of the organic light emitting device may include at least one amine compound represented by Formula 1.

[0142] In an embodiment, the emission layer of the organic light emitting device may include a host and a dopant, and the dopant may include at least one amine compound represented by Formula 1 and an amount of the host may be greater than an amount of the dopant.

[0143] In an embodiment, the emission layer may further include a sensitizer.

[0144] The sensitizer may include at least one of an organic metal compound, a heterocyclic compound, or any combination thereof.

[0145] In an embodiment, the organometallic compound may include ruthenium (Ru), palladium (Pd), rhenium (Re), osmium (Os), platinum (Pt), or any combination thereof.

[0146] In an embodiment, the organometallic compound may be a compound represented by Formula 81.

[0147] In an embodiment, the sensitizer includes the organometallic compound, and the dopant and the organometallic compound may satisfy Equation 1:

[0148] Equation 1

[0149] T1(S PH )-S1(D)>0

[0150] Where, in equation 1,

[0151] T1(S PH ) is the lowest excited triplet energy level of the organometallic compound, and

[0152] S1(D) is the lowest excited singlet energy level of the dopant.

[0153] When the sensitizer including the organic metal compound and the dopant including the amine compound satisfy equation 1, high exciton energy can be transferred to the sensitizer and then to the dopant. Therefore, the deterioration of the dopant is suppressed, and thus, the life characteristics can be improved, and the spectral overlap between the sensitizer and the dopant can be increased, resulting in efficient (effective) energy transfer. Therefore, the radiation decay rate increases and the non-radiative transition decreases, so that the luminous efficiency of the organic light-emitting device can be improved.

[0154] In an embodiment, the heterocyclic compound may be a compound satisfying Equation E:

[0155] <Equation E>

[0156] |T1(S DF )-S1(S DF )|≤0.3eV

[0157] Where, in equation E,

[0158] T1(S DF ) is the lowest excited triplet energy level of the heterocyclic compound, and

[0159] S1(S DF ) is the lowest excited singlet energy level of the heterocyclic compound.

[0160] In an embodiment, the heterocyclic compound may be a thermally activated delayed fluorescence (TADF) compound in which the electron donor portion and the electron acceptor portion are spaced apart from each other. In this case, the heterocyclic compound can effectively prevent intramolecular orbital overlap, and thus, the singlet and triplet states of the molecule are prevented from overlapping, resulting in a very low ΔE st Therefore, even at room temperature, reverse intersystem crossing can occur from the triplet excited state to the singlet excited state by thermal activity (thermal activity). As a result, since the excitons in the triplet state are used for light emission, the luminous efficiency can be improved.

[0161] In an embodiment, the heterocyclic compound may be at least one of compounds TA-1 to TA-5.

[0162]

[0163] In an embodiment, the sensitizer includes the heterocyclic compound, and the dopant and the heterocyclic compound may satisfy Equation 2:

[0164] <Equation 2>

[0165] S1(S DF )-S1(D)>0

[0166] Where, in equation 2,

[0167] S1(S DF ) is the lowest excited singlet energy level of the heterocyclic compound, and

[0168] S1(D) is the lowest excited singlet energy level of the dopant.

[0169] When the sensitizer including the heterocyclic compound and the dopant satisfy equation 2, high exciton energy can be transferred to the sensitizer and then to the dopant. As a result, energy can be easily transferred and the time of residence in the sensitizer can be minimized. Therefore, the deterioration of the sensitizer is suppressed and the life characteristics can be improved. In addition, due to the reverse intersystem crossing of the TADF sensitizer, the radiative transition increases and the non-radiative transition decreases, and therefore, the luminous efficiency of the organic light-emitting device can be improved.

[0170] The lowest excited singlet energy level, the lowest excited triplet energy level of the sensitizer (including the organic metal compound and the heterocyclic compound), and the lowest excited singlet energy level of the dopant are evaluated using the DFT method of the Gaussian program with structural optimization at the B3LYP / 6-31G (d, p) level.

[0171] In an embodiment, the dopant and the sensitizer may satisfy Equation 3.

[0172] <Equation 3>

[0173] HOMO(S)-HOMO(D)>0

[0174] In equation 3,

[0175] HOMO(S) is the HOMO energy level of the sensitizer, and

[0176] HOMO(D) is the HOMO energy level of the dopant.

[0177] In the case where the sensitizer and the dopant satisfy Equation 3, the absolute value of the HOMO energy level of the dopant is large (i.e., the HOMO energy level of the dopant is deeper), so that direct injection of charges captured by the dopant can be prevented, and thus, a superfluorescent system can be easily obtained. In this case, since high exciton energy can be transferred to the sensitizer and then to the dopant, deterioration of the dopant can be suppressed and life characteristics can be improved. In addition, since non-radiative transitions are reduced due to the energy transfer mechanism described above, the luminous efficiency of the organic light-emitting device can be improved.

[0178] The HOMO levels of each of the dopant and the sensitizer were evaluated using the DFT method of the Gaussian program with structure optimization at the B3LYP / 6-31G(d,p) level.

[0179] The emission layer may emit red light, green light, or blue light.

[0180] According to one embodiment, the emission layer may emit blue light having a maximum emission wavelength of about 410 nm to about 490 nm.

[0181] In one embodiment, the amine compound represented by Formula 1 may be included in a hole transport region of the organic light emitting device.

[0182] In an embodiment, the hole transport region of the organic light-emitting device includes at least one of a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and at least one of the hole injection layer, the hole transport layer, the electron blocking layer, or a combination thereof may include an amine compound represented by Formula 1.

[0183] In one embodiment, the amine compound represented by Formula 1 may be included in an electron transport region of the organic light emitting device.

[0184] In an embodiment, the electron transport region of the organic light-emitting device includes at least one of a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof, and at least one of the hole blocking layer, the electron transport layer, the electron injection layer, or any combination thereof may include an amine compound represented by Formula 1.

[0185] In an embodiment, the hole transport region of the organic light emitting device may include an electron blocking layer, and the amine 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.

[0186] In an embodiment, the electron transport region of the organic light emitting device may include a hole blocking layer, and the amine compound represented by Formula 1 may be included in the hole blocking layer. The hole blocking layer may be in direct contact with the emission layer.

[0187] In an embodiment, the organometallic compound may be represented by Formula 81:

[0188] <Formula 81>

[0189] M(L 81 ) n81 (L 82 ) n82

[0190] <Formula 81A>

[0191]

[0192] In equations 81 and 81A,

[0193] M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh),

[0194] 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, L 81 Two or more of may be the same or different from each other,

[0195] L82 may be an organic ligand, n82 may be an integer of 0-4, and when n82 is 2 or greater, L 82 Two or more of may be the same or different from each other,

[0196] Y 81 -Y 84 may be independently carbon (C) or nitrogen (N),

[0197] Y 81 and Y 82 can be connected to each other via a single bond or a double bond, and Y 83 and Y 84 can be connected to each other via single or double bonds,

[0198] CY 81 and CY 82 Can be independently C 5 -C 30 Carbocyclic group or C 2 -C 30 Heterocyclic groups,

[0199] CY 81 and CY 82 may optionally additionally be bound to one another via an organic linking group,

[0200] R 81 -R 85 can 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 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60Aryloxy, 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 ), or -P(=O)(Q 88 )(Q 89 ),

[0201] a81-a83 can each independently be an integer of 0-5,

[0202] When a81 is 2 or more, two or more R 81 may be the same or different from each other,

[0203] When a82 is 2 or more, two or more R 82 may be the same or different from each other,

[0204] When a81 is 2 or greater, two adjacent R 81 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),

[0205] When a82 is 2 or greater, two adjacent R 82 Can be optionally linked to form a saturated or unsaturated C 2 -C 30ring (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),

[0206] R 88 Can be related to R 81 Same as described,

[0207] R 89 Can be related to R 82 Same as described,

[0208] * and *' in formula 81A each represent a binding site with M in formula 81, and

[0209] 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 1 -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 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 1 -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,

[0210] Where Q 81 -Q 89 and Q 91 -Q 93 can be independently hydrogen, deuterium, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.

[0211] In one embodiment, in Formula 81A,

[0212] a83 can be 1 or 2,

[0213] R 83 -R 85Can be independently:

[0214] -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, or -CD 2 CDH 2 ;

[0215] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0216] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of: deuterium, C 1 -C 10 Alkyl, phenyl, or any combination thereof,

[0217] However, the embodiments of the present disclosure are not limited thereto.

[0218] In one or more embodiments, in Formula 81A,

[0219] Y 81 Can be nitrogen, Y 82 and Y 83 Can be carbon, Y 84 Can be nitrogen or carbon,

[0220] CY 81 and CY 82 can be independently a cyclopentadiene group, a phenyl group, a heptadiene group, an indene group, a naphthalene group, group, indacene group, acenaphthene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, group, tetraphenyl group, phenoxy group, perylene group, pentacene group, hexaphenyl group, rubrocene 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 also includes oxazole group, benzocarbazole group, dibenzocarbazole group, imidazopyridine group, imidazopyrimidine group, dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, dibenzosilole group, or 2,3-dihydro-1H-imidazole group.

[0221] 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 82 It may be a benzene group, a naphthalene group, a fluorene group, a dibenzofuran group, or a dibenzothiophene group, but the embodiments of the present disclosure are not limited thereto.

[0222] 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 the embodiments of the present disclosure are not limited thereto.

[0223] In one or more embodiments, in Formula 81A,

[0224] Y 81 may be nitrogen and Y 82 -Y 84Each of them can be carbon,

[0225] 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 Azole group,

[0226] 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.

[0227] In one or more embodiments, in Formula 81A,

[0228] R 81 and R 82 Can be independently:

[0229] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF 5 , C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy;

[0230] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof;

[0231] 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, or imidazopyrimidinyl;

[0232] 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, Oxazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl: 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, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or any combination thereof; or

[0233] -B(Q 86 )(Q 87 ) or -P(=O)(Q 88 )(Q 89 ),

[0234] Where Q 86 -Q 89 Can be independently:

[0235] -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 2CD 3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;

[0236] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0237] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of: deuterium, C 1 -C 10 Alkyl, phenyl, or any combination thereof.

[0238] In one or more embodiments, in Formula 81A, the number of R is a81 81 and R with a quantity of a82 82 At least one of may be a cyano group.

[0239] In one or more embodiments, in Formula 81A, the number of R is a82 82 At least one of may be a cyano group.

[0240] In one or more embodiments, in Formula 81A, the number of R is a81 81 and R with a quantity of a82 82 At least one of may be deuterium.

[0241] 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(60), 3-1(61) 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):

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248] 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),

[0249] X 1 Can be O, S, C (Z 21 )(Z 22 ), or N(Z 23 ),

[0250] X 31 Can be N or C(Z 1a ) and X 32 Can be N or C(Z 1b ),

[0251] X 41 Can be O, S, N (Z 1a ), or C(Z 1a )(Z 1b ),

[0252] 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 23 Can be independently:

[0253] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF 5 , C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy;

[0254] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2H, -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, pyridyl, pyrimidinyl, or any combination thereof;

[0255] 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, or imidazopyrimidinyl;

[0256] 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, Oxazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2H.-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, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or any combination thereof; or

[0257] -B(Q 86 )(Q 87 ) or -P(=O)(Q 88 )(Q 89 ),

[0258] Where Q 86 -Q 89 Can be independently:

[0259] -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, or -CD 2 CDH 2 ;

[0260] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0261] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of: deuterium, C 1 -C 10 Alkyl, phenyl, or any combination thereof.

[0262] d2 and e2 can each independently be 0 or 2,

[0263] e3 can be an integer from 0 to 3.

[0264] d4 and e4 can each independently be an integer from 0 to 4,

[0265] d6 and e6 can each independently be an integer from 0 to 6,

[0266] d8 and e8 can each independently be an integer from 0 to 8,

[0267] * and *' each represent a binding site to M in Formula 1.

[0268] 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.

[0269] In an embodiment, the organometallic compound may be represented by the following formula 91:

[0270] <Formula 91>

[0271]

[0272] Among them, in formula 91,

[0273] M is the same as described above,

[0274] CY 91 -CY 94 Each independently and about CY 81 and CY 82 Same as described,

[0275] T 91 -T 94 can be independently a single bond, *-N(R 95 )-*'、*-B(R 95 )-*'、*-P(R 95 )-*'、*-C(R 95 )(R 96 )-*'、*-Si(R 95 )(R 96 )-*'、*-Ge(R 95 )(R 96 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(R 95 )=C(R 96 )-*', *-C(=S)-*', or *-C≡C-*',

[0276] Y 91 -Y 94 can be independently C or N,

[0277] X 91 -X 98 can be independently C or N,

[0278] R 91 -R 96 Can be independently related to R 81 and R 82 Same as described,

[0279] a91-a94 can each independently be an integer of 0-5,

[0280] When a91 is 2 or more, two or more R 91 may be the same or different from each other,

[0281] When a92 is 2 or more, two or more R 92 may be the same or different from each other,

[0282] When a93 is 2 or more, two or more R 93 may be the same or different from each other,

[0283] When a94 is 2 or more, two or more R 94 may be the same or different from each other,

[0284] 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 1 -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 1 -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,

[0285] Where Q 91-Q 93 can be independently hydrogen, deuterium, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.

[0286] In addition, in embodiments, the organometallic compound may be electrically neutral rather than a salt consisting of a cation and anion pair.

[0287] In one or more embodiments, the organometallic compound may include compounds PD1 to PD83 and FIr 6 At least one of, but the embodiments of the present disclosure are not limited thereto.

[0288]

[0289]

[0290]

[0291]

[0292] The expression “(the organic layer) includes at least one amine compound represented by Formula 1” used herein may include the case where “(the organic layer) includes the same amine compound represented by Formula 1” and the case where “(the organic layer) includes two or more different amine compounds represented by Formula 1”.

[0293] For example, the organic layer may include only Compound 1 as the amine compound. In this embodiment, Compound 1 may be included 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 amine 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).

[0294] 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.

[0295] 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 an organic compound, the "organic layer" may further include an organic metal complex including a metal.

[0296] Figure 1 FIG. 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to an exemplary embodiment. Figure 1 The structure of an organic light emitting device according to an embodiment of the present disclosure and a method of manufacturing the organic light emitting device according to an embodiment of the present disclosure are described. The organic light emitting device 10 includes a first electrode 11 , an organic layer 15 , and a second electrode 19 which are sequentially stacked.

[0297] 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, easy handling (processing), and water resistance.

[0298] 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).

[0299] 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.

[0300] The organic layer 15 is provided on the first electrode 11 .

[0301] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0302] The hole transport region may be between the first electrode 11 and the emission layer.

[0303] The hole transport region may include at least one of: a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0304] 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.

[0305] 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.

[0306] 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 Torr - about 10 -3 Torr vacuum pressure, and approx. -about However, the deposition conditions are not limited thereto.

[0307] 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.

[0308] 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.

[0309] The hole transport region may include at least one of m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201 below, a compound represented by Formula 202 below, or any combination thereof:

[0310]

[0311]

[0312] Formula 201

[0313]

[0314] Formula 202

[0315]

[0316] Ar in Formula 201 101 -Ar 102 Can be independently:

[0317] Phenylene, cyclopentadienylene, indenylene, naphthylene, 1-Heptalenyl, 1-Heptalenyl, 1-Acenaphthenylidene, 1-Fluorenyl, 1-Phenanthrenyl, 1-Anthracenyl, 1-Fluoranthenyl, 1-Benzo[9,10]phenanthrenyl, 1-Pyrenyl, 1-Phenanth ... phenylene, tetraphenylene, perylene, perylene, or pentphenylene; or

[0318] Each of which is substituted by at least one of the following: phenylene, pentalene, indenylene, naphthylene, 1-Heptalenyl, 1-Acenaphthene, 1-Fluorenyl, 1-Phenanthrenyl, 1-Phenanthrenyl, 1-Anthracene, 1-Fluoranthenyl, 1-Benthrenyl, 1-Phenan ... a phenylene group, a tetraphenylene group, a perylene group, a perylene group, or a pentphenylene group: a deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof.

[0319] 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.

[0320] R in formula 201 and 202 101 -R 108 , R 111 -R 119 and R 121 -R 124 Can be independently:

[0321] 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.) or C 1 -C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);

[0322] Each of the following C 1 -C 10 Alkyl or C 1 -C 10 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, or any combination thereof;

[0323] Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl; or

[0324] A phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl group, each substituted by at least one of: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, or any combination thereof,

[0325] However, the embodiments of the present disclosure are not limited thereto.

[0326] R in Formula 201 109 Can be:

[0327] phenyl, naphthyl, anthracenyl, or pyridyl; or

[0328] phenyl, naphthyl, anthracenyl, or pyridyl, each substituted by at least one of: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, naphthyl, anthracenyl, pyridyl, or any combination thereof.

[0329] According to an embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A, but embodiments of the present disclosure are not limited thereto:

[0330] Formula 201A

[0331]

[0332] R in Formula 201A 101 , R 111 , R 112 , and R 109 This can be understood by referring to the description provided herein.

[0333] 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:

[0334]

[0335]

[0336]

[0337] 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, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about -about For example, about -about and the thickness of the hole transport layer may be in the range of 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.

[0338] 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.

[0339] The charge generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, or a compound containing a cyano group, but the embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are quinone derivatives such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and compounds containing a cyano group such as the following compound HT-D1 or compound HT-D2, but are not limited thereto.

[0340]

[0341] The hole transport region may further include a buffer layer.

[0342] In addition, 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.

[0343] 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, the deposition or coating conditions may be similar to those applied when forming the hole injection layer, although the deposition or coating conditions may vary depending on the material used to form the emission layer.

[0344] 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.

[0345]

[0346] The thickness of the electron blocking layer may be about -about For example, about -about When the thickness of the electron blocking layer is within the above-described range, the electron blocking layer may have satisfactory electron blocking characteristics without a significant increase in driving voltage.

[0347] 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.

[0348] The emission layer may include an amine compound represented by Formula 1.

[0349] In an embodiment, the emission layer may include the amine compound represented by Formula 1 only.

[0350] In an embodiment, the emission layer may include a host and a dopant, and the dopant may include an organic metal compound represented by Formula 1.

[0351] The host may include at least one of TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, or any combination thereof:

[0352]

[0353] In one or more embodiments, the host may further include a compound represented by Formula 301 below.

[0354] Formula 301

[0355]

[0356] Ar in Formula 301 111 and Ar 112 Can be independently:

[0357] Phenylene, naphthylene, phenanthrenyl, or pyrenylene; or

[0358] Phenylene, naphthylene, phenanthrenylene, or pyrenylene, each substituted with at least one of phenyl, naphthyl, anthracenyl, or any combination thereof.

[0359] Ar in Formula 301 113 -Ar 116 Can be independently:

[0360] C 1 -C 10 alkyl, phenyl, naphthyl, phenanthrenyl, or pyrenyl; or

[0361] Phenyl, naphthyl, phenanthrenyl, or pyrenyl, each substituted with at least one of phenyl, naphthyl, anthracenyl, or any combination thereof.

[0362] g, h, i, and j in Formula 301 may each independently be an integer of 0-4, and may be 0, 1, or 2, for example.

[0363] Ar in Formula 301 113 -Ar 116 Can be independently:

[0364] C substituted with at least one of the following 1 -C 10 Alkyl: phenyl, naphthyl, anthracenyl, or any combination thereof;

[0365] Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl;

[0366] phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl, each substituted by at least one of: 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 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, fluorenyl, or any combination thereof; or

[0367]

[0368] However, the embodiments of the present disclosure are not limited thereto.

[0369] In one or more embodiments, the host may include a compound represented by the following formula 302:

[0370] <Formula 302>

[0371]

[0372] Ar in formula 302 122 -Ar 125 With respect to Ar in Formula 301 113 Same as described in detail.

[0373] Ar in formula 302 126 and Ar 127 Can be independently C 1 -C 10 Alkyl (eg, methyl, ethyl, or propyl).

[0374] In formula 302, k and l may each independently be an integer of 0 to 4. For example, k and l may be 0, 1, or 2.

[0375] 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, or 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.

[0376] 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 extinction.

[0377] When the emission layer includes an amine compound represented by Formula 1 and a second compound different from the amine compound, a weight ratio of the amine compound represented by Formula 1 to the second compound may be in a range of about 1:99 to about 99:1, for example, about 70:30 to about 30:70. In one or more embodiments, a weight ratio of the amine compound represented by Formula 1 to the second compound may be in a range of about 60:40 to about 40:60. When the weight ratio of the amine 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 achieved.

[0378] The thickness of the emission layer may be about -about For example, about -about When the thickness of the emission layer satisfies the above range, excellent light emitting characteristics can be exhibited without a significant increase in driving voltage.

[0379] Then, an electron transport region may be disposed on the emission layer.

[0380] The electron transport region may include at least one of: a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0381] 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.

[0382] The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region can be understood by referring to the conditions for forming the hole injection layer.

[0383] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, or any combination thereof, but embodiments of the present disclosure are not limited thereto.

[0384]

[0385] In one or more embodiments, the hole blocking layer may include an amine compound represented by Formula 1.

[0386] 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.

[0387] The electron transport layer may further include at least one of the following: BCP, Bphen, Alq 3 , BAlq, TAZ, NTAZ, or any combination thereof.

[0388]

[0389] In one or more embodiments, the electron transport layer may include at least one of ET1 to ET25, but is not limited thereto:

[0390]

[0391]

[0392] 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.

[0393] In addition, the electron transport layer may further include a material containing a metal in addition to the materials described above.

[0394] 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:

[0395]

[0396] The electron transport region may include an electron injection layer (EIL) that facilitates the flow of electrons from the second electrode 19 thereinto.

[0397] The electron injection layer may include at least one of the following: LiQ, LiF, NaCl, CsF, Li 2 O, BaO, or any combination thereof.

[0398] 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.

[0399] A second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. The material for forming the second electrode 19 may be a metal, an alloy, a conductive compound, or a combination thereof having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as a material for forming the second electrode 19. In one or more embodiments, in order to manufacture a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0400] In the above, reference has been made to Figure 1 An organic light emitting device is described, but embodiments of the present disclosure are not limited thereto.

[0401] 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.

[0402] 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.

[0403] As used herein, the term "C 2 -C 60 "Alkenyl" refers to a group consisting of a carbon-carbon double bond inserted into a 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed in the middle or at the end of an alkyl group, and examples thereof include vinyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0404] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a group consisting of a carbon-carbon triple bond inserted into a 2 -C 60 The term "C" as used herein is a hydrocarbon group formed in the middle or at the end 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.

[0405] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring 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 ring 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 -C10 Cycloalkyl is a divalent group of the same structure.

[0406] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent saturated monocyclic group having at least one N, O, P, Si, S, B, Se, Ge, or a combination thereof as a ring 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.

[0407] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent cyclic 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.

[0408] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl" refers to a monovalent monocyclic group having at least one heteroatom N, O, P, Si, S, B, Se, Ge, or a combination thereof as a ring atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. 1 -C 10 Examples of heterocycloalkenyl are 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. 1 -C 10 "Heterocycloalkenylene" refers to a 1 -C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0409] 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 60Examples 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.

[0410] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one N, O, P, Si, S, B, Se, Ge, or a combination thereof 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 N, O, P, S, B, Se, Ge, or a combination thereof 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.

[0411] 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).

[0412] As used herein, the term "C 7 -C 60 "Alkylaryl" means a C 1 -C 54 Alkyl substituted C 6 -C 59 Examples include tolyl.

[0413] As used herein, the term "C 2 -C 60 "Alkylheteroaryl" means a C 1-C 59 Alkyl substituted C 1 -C 59 Heteroaryl. Examples include a pyridine ring substituted with a methyl group.

[0414] As used herein, the term "C 1 -C 60 "Heteroaryloxy" means -OA 104 (A 104 C 1 -C 60 Heteroaryl), and as used herein, the term "C 1 -C 60 "Heteroarylthio" means -SA 105 (A 105 C 1 -C 60 heteroaryl).

[0415] 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 monovalent non-aromatic fused polycyclic groups 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.

[0416] 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 N, O, P, Si, S, B, Se, Ge, or a combination thereof as a ring-forming atom in addition to carbon atoms, and not having aromaticity in terms of its entire molecular structure. Examples of monovalent non-aromatic fused heteropolycyclic groups include carbazolyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as a monovalent non-aromatic fused heteropolycyclic group.

[0417] As used herein, the term "C 5 -C 30 The term "carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring atoms. 5 -C 30 The carbocyclic group may be a monocyclic group or a polycyclic group.

[0418] As used herein, the term "C 1 -C 30The term "heterocyclic group" refers to a saturated or unsaturated cyclic group having at least one heteroatom N, O, Si, P, S, B, Se, Ge, or a combination thereof as a ring atom in addition to 1 to 30 carbon atoms. 1 -C 30 The heterocyclic group may be a monocyclic group or a polycyclic group.

[0419] 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 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Alkyl aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 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:

[0420] 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 -C60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy;

[0421] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, 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 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 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 )、-P(=O)(Q 18 )(Q 19 ), or any combination thereof;

[0422] C 3 -C 10 Cycloalkyl, C1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 an alkylheteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group;

[0423] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, 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 -C60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 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 )、-P(=O)(Q 28 )(Q 29 ), or any combination thereof; or

[0424] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 ), or -P(=O)(Q 38 )(Q 39 ),

[0425] Where Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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, deuterated, C 1 -C60 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 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, deuterated, 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 condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.

[0426] Hereinafter, the compound and the organic light-emitting device according to the embodiment are described in detail with reference to the synthesis examples and the examples. However, the organic light-emitting device is not limited thereto. The phrase "using 'B' instead of 'A'" used in describing the synthesis examples means that the amount of 'A' used is the same as the amount of 'B' used in terms of molar equivalent.

[0427] Example

[0428] Synthesis Example 1: Synthesis of Compound 1

[0429]

[0430] In a round-bottom flask, 4.777 g (14.86 mmol) of N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-3-amine, 2.140 g (5.94 mmol) of 1,6-dibromopyrene, 1.367 g (2.38 mmol) of bis(dibenzylideneacetone)palladium (Pd(dba) 2 ), 0.962ml (2.38mmol) of tri-tert-butylphosphine (ttbp, 50% (w / w) in toluene), and 2.856g (29.72mmol) of sodium tert-butoxide (NaOtBu) were added to 30mL of dioxane, and then refluxed for 24 hours while heating at 110°C in a nitrogen atmosphere. Upon completion of the reaction, the mixture was cooled to room temperature and added dropwise to 800mL of methanol for crystallization, and the resulting solid was filtered therefrom and washed with methanol. The solid obtained therefrom was dissolved in 8L of toluene for hot silica filtration, and the filtrate was concentrated to obtain a solid. The obtained solid was recrystallized again using 1800mL of DMF, filtered, and dried under vacuum to obtain compound 1 (2.51g). Compound 1 was confirmed by LC-MS.

[0431] C 64 H 44 N 2 :M + 841.336

[0432] Example 1

[0433] The glass substrate on which ITO was deposited as an electrode (anode) was cut into a size of 50 mm×50 mm×0.5 mm, and then ultrasonically treated in acetone, isopropyl alcohol, and pure water for 15 minutes each, and then cleaned by exposure to UV ozone for 30 minutes.

[0434] Then, m-MTDATA is replaced with The deposition rate is deposited on the ITO electrode (anode) of the glass substrate to form a The hole injection layer is then formed with α-NPD is deposited on the hole injection layer at a deposition rate of The hole transport layer has a thickness of .

[0435] CBP (host), compound PD79 (sensitizer), and compound 1 (dopant) were co-deposited on the hole transport layer in a weight ratio of 88.5:10:1.5 to form a The thickness of the emission layer.

[0436] BAlq The deposition rate is deposited on the emission layer to form a The hole blocking layer is of thickness , and the Alq 3 deposited on the hole blocking layer to form a An electron transport layer having a thickness of , and then LiF is deposited on the electron transport layer to form a An electron injection layer having a thickness of , and then Al is vacuum deposited on the electron injection layer to form a The second electrode (cathode) has a thickness of Fabrication of an organic light-emitting device with a structure.

[0437]

[0438] Comparative Examples 1-7

[0439] An organic light-emitting device was manufactured in the same manner as in Example 1, except that when forming the emission layer, for use as a dopant, Compounds AG shown in Table 1 were used instead of Compound 1. Evaluation Example 1: Characterization of Organic Light-Emitting Device

[0440] The driving voltage, external quantum efficiency (EQE), maximum emission wavelength and lifetime (T 95 The results are shown in Table 1. A current-voltage meter (Keithley 2400) and a brightness meter (Minolta Cs-1000A) were used as the evaluation equipment, and the lifespan (T 95 ) (at 1000 nits), and the results are expressed as relative values.

[0441] Table 1

[0442]

[0443]

[0444] It can be seen from Table 1 that, compared with the organic light-emitting devices of Comparative Examples 1-7, the organic light-emitting device of Example 1 has superior external quantum efficiency and long lifetime.

[0445] The amine compound has excellent electrical characteristics and thermal stability, and has a structure suitable for efficient energy transfer and minimizing charges trapped by the dopant. Therefore, an organic light-emitting device using the amine compound can have high efficiency and long lifespan.

[0446] 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. An amine compound represented by Formula 1: Formula 1 in, In formula 1, R1-R8 are each independently hydrogen or deuterium, R 11 -R 14 Each independently Hydrogen, Deuterium, C1-C 20 Alkyl, or C1-C 20 alkoxy; or C1-C substituted with deuterium 20 Alkyl or C1-C 20 Alkoxy, R 21 -R 24 Each independently Hydrogen, Deuterium, C1-C 20 Alkyl, or C1-C 20 alkoxy; or C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -CD3, -CD2H, -CDH2, C1-C 10 Alkyl, or any combination thereof, b11-b14 are each independently an integer of 1-4, and b21-b24 are each independently an integer of 1-5.

2. The amine compound according to claim 1, wherein R 21 -R 24 Each independently is: Hydrogen, deuterium, or a group represented by one of formulae 9-1 to 9-19: in, In Formulae 9-1 to 9-19, * represents a bonding site with an adjacent atom.

3. The amine compound according to claim 1, wherein R1 to R8 are each hydrogen.

4. The amine compound as claimed in claim 1, wherein when R 11 -R 14 When each is not hydrogen, b11-b14 are each 1 or 2, and When R 21 -R 24 When each is not hydrogen, b21-b24 are each 1, 2, or 3.

5. The amine compound according to claim 1, wherein the amine compound represented by Formula 1 is any one of Compounds 1, 19, and 21 to 26:

6. An 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, and The organic layer comprises at least one amine compound as claimed in any one of claims 1 to 5. 7 . The organic light emitting device of claim 6 , wherein the amine compound represented by Formula 1 is included in the emission layer.

8. The organic light emitting device of claim 7, wherein the emission layer comprises a host and a dopant, The dopant includes an amine compound represented by Formula 1, and The amount of the host is greater than the amount of the dopant.

9. The organic light emitting device according to claim 8, wherein the emission layer further comprises a sensitizer, and The sensitizer includes at least one of the following: an organic metal compound, a heterocyclic compound, or any combination thereof.

10. The organic light emitting device according to claim 9, wherein the sensitizer comprises the organic metal compound, The organometallic compound includes ruthenium (Ru), palladium (Pd), rhenium (Re), osmium (Os), platinum (Pt), or any combination thereof, and The dopant and the organometallic compound satisfy Equation 1: Equation 1 T1(S PH )-S1(D)>0 in, In equation 1, T1(S PH ) is the lowest excited triplet energy level of the organometallic compound, and S1(D) is the lowest excited singlet energy level of the dopant.

11. The organic light emitting device according to claim 9, wherein the sensitizer comprises the heterocyclic compound, and The heterocyclic compound satisfies equation E: <Equation E> |T1(S DF )-S1(S DF )|≤0.3eV Among them, In equation E, T1(S DF ) is the lowest excited triplet energy level of the heterocyclic compound, and S1(S DF ) is the lowest excited singlet energy level of the heterocyclic compound.

12. The organic light emitting device of claim 11, wherein the dopant and the heterocyclic compound satisfy Equation 2: <Equation 2> S1(S DF )-S1(D)>0 in, In equation 2, S1(S DF ) is the lowest excited singlet energy level of the heterocyclic compound, and S1(D) is the lowest excited singlet energy level of the dopant.

13. The organic light emitting device according to claim 9, wherein the dopant and the sensitizer satisfy Equation 3: <Equation 3> HOMO(S)-HOMO(D)>0 in, In equation 3, HOMO(S) is the HOMO energy level of the sensitizer, and HOMO(D) is the HOMO energy level of the dopant. 14 . The organic light emitting device of claim 7 , wherein the emission layer emits blue light having a maximum emission wavelength of 410 nm to 490 nm.

15. The organic light emitting device of claim 6, 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 of the following: a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and The electron transport region includes at least one of the following: a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. 16 . The organic light emitting device of claim 15 , wherein the amine compound represented by Formula 1 is included in the hole transport region or the electron transport region.

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