Organometallic compound, and organic light-emitting device and diagnostic composition comprising the same

Abstract

Disclosed are an organic metal compound, an organic light-emitting device and a diagnostic composition comprising the same. The organic metal compound is represented by Formula 1, wherein in Formula 1, M is a transition metal, L 1 is a ligand represented by Formula 2A, L 2 is a ligand represented by formula 2B, n1 is 1 or 2, wherein when n1 is 2, the two groups L 1 are the same as or different from each other, n2 is 1 or 2, wherein when n2 is 2, the two groups L 2 are the same or different, the sum of n1 and n2 is 2 or 3, and L 1 and L 2 In Formula 2A and Formula 2B, X 1 CY 1 CY 2 CY 14 , R 1 ‑R 3 , R 11 ‑R 14 , Z 1 ‑Z 3 , a1, a2, a3, b1, and c1 are the same as those described in the specification, and * and *' in Formula 2A and 2B each represent a binding site with M in Formula 1. Formula 1M(L 1 ) n1 (L 2 ) n2 #imgabs0#

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of and priority to Korean Patent Application No. 10-2018-0155457 filed on December 5, 2018 in the Korean Intellectual Property Office and all rights arising therefrom, the contents of which are incorporated herein by reference in their entirety. Technical Field

[0003] One or more embodiments of the present disclosure are directed to an organometallic compound, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound. Background Art

[0004] An organic light emitting device (OLED) is a self-emitting device that has excellent characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed and produces a full-color image.

[0005] In an example, an organic light emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode. Holes provided from the anode 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.

[0006] Meanwhile, the luminescent compound can be used to monitor, sense or detect a variety of biological materials, including cells and proteins.Examples of the luminescent compound include phosphorescent luminescent compounds.

[0007] Various types of organic light emitting devices are known. However, there is still a need for OLEDs with low driving voltage, high efficiency, high brightness, and long lifetime. Summary of the invention

[0008] Provided are an organometallic compound, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound.

[0009] Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments.

[0010] According to one aspect of the embodiment, the organometallic compound is represented by Formula 1:

[0011] Formula 1

[0012] M(L 1) n1 (L 2 ) n2

[0013] In formula 1,

[0014] M may be a transition metal,

[0015] L 1 may be a ligand represented by Formula 2A,

[0016] n1 can be 1 or 2, wherein when n1 is 2, the two groups L 1 may be the same or different from each other,

[0017] L 2 may be a ligand represented by Formula 2B,

[0018] n2 can be 1 or 2, wherein when n2 is 2, the two groups L 2 may be the same or different from each other,

[0019] The sum of n1 and n2 can be 2 or 3, and

[0020] L 1 and L 2 Can be different from each other:

[0021]

[0022] In Formulas 2A and 2B,

[0023] X 1 Can be C, N, Si, or P,

[0024] Cyclo 1 CY 2 , and ring CY 14 Can be independently C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0025] R 1 -R 3 Can be independently C 1 -C 60 Alkyl or C 6 -C 60 Aryl, each of which is unsubstituted or substituted by at least one selected from the group consisting of 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, and C 1 -C 10 alkyl,

[0026] Z 1 -Z 3 and R 11 -R 14 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 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 7 -C 60 Arylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 Heteroarylthio, substituted or unsubstituted C 2 -C 60 heteroarylalkyl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4)(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 ), and -P(=O)(Q 8 )(Q 9 ), where R 12 But it is neither hydrogen nor methyl,

[0027] a1 can be an integer from 0 to 3, wherein when a1 is 2 or greater, two or more groups Z 1 may be the same or different from each other,

[0028] a2, a3, and b1 may each independently be an integer of 0-20, wherein when a2 is 2 or greater, two or more groups Z 2 may be the same as or different from each other. When a3 is 2 or greater, two or more groups Z 3 may be the same as or different from each other, and when b1 is 2 or greater, two or more groups R 14 may be the same or different from each other,

[0029] c1 can be an integer from 1 to 4, wherein when c1 is 2 or greater, two or more The groups represented by may be the same as or different from each other,

[0030] When a1 is 2 or more, two or more groups Z 1 may be optionally linked to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0031] When a2 is 2 or more, two or more groups Z 2 may be optionally linked to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0032] When a3 is 2 or more, two or more groups Z 3 may be optionally linked to form an unsubstituted or substituted with at least one R 10a Substituted C 5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0033] R 12 and R 13 may be optionally linked to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0034] When b1 is 2 or more, two or more groups R 14 may be optionally linked to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0035] Two or more selected from Z 1 and Z 2 The substituents may be optionally linked to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0036] Two or more selected from R 11 -R 14 The substituents may be optionally linked to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0037] R 10a Can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1-C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 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 7 -C 60 Arylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 Heteroarylthio, substituted or unsubstituted C 2 -C 60 heteroarylalkyl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 ), and -P(=O)(Q 8 )(Q 9 ),

[0038] * and *' in Formula 2A and 2B each represent a binding site with M in Formula 1,

[0039] Substituted C 1 -C 60 Alkyl, substituted C2 -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 7 -C 60 Arylalkyl, substituted C 1 -C 60 Heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 Heteroarylthio, substituted C 2 -C 60 At least one substituent of the heteroaralkyl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may each be independently selected from:

[0040] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy;

[0041] Each of the following is substituted by at least one C 1 -C 60 Alkyl, C 2 -C60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60 heteroarylalkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 ), and -P(=O)(Q 18 )(Q 19 );

[0042] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60 a heteroaralkyl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group;

[0043] Each of the following is substituted by at least one C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2-C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60 heteroarylalkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ), and -P(=O)(Q 28 )(Q 29 );and

[0044] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 ), or -P(=O)(Q 38 )(Q 39 ),and

[0045] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39can be independently selected from 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, 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, selected from 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, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.

[0046] Another aspect of the present disclosure provides an organic light emitting device including: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one organic metal compound represented by Formula 1.

[0047] The emission layer may include the at least one organometallic compound. The organometallic compound in the emission layer may act as a dopant.

[0048] Another aspect of the present disclosure provides a diagnostic composition comprising at least one organometallic compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0049] By combining Figure 1 These and / or other aspects will become clear and more readily understood from the following description of the embodiments contemplated herein. Figure 1 is a schematic diagram of an organic light emitting device according to an embodiment. DETAILED DESCRIPTION

[0050] 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 description of the embodiments is provided only by reference to the accompanying drawings to illustrate aspects of the present description. 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) of" modify the entire list of elements when before or after the list of elements and do not modify the individual elements of the list.

[0051] It will be understood that when an element is referred to as being "on" another element, it can be directly in contact with the other element or intervening elements may exist therebetween. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements.

[0052] It will be understood that although the terms first, second, third, etc. can be used to describe various elements, components, regions, layers and / or parts in this article, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish an element, component, region, layer or part from another element, component, region, layer or part. Therefore, without departing from the teaching of the present embodiment, the first element, component, region, layer or part discussed below can be referred to as the second element, component, region, layer or part.

[0053] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0054] The term "or" means "and / or". It will be further understood that the terms "include" or "comprises" 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.

[0055] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of this disclosure and the relevant art, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0056] 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 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, for example, caused by manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. In addition, the illustrated sharp corners may be rounded. Therefore, the regions illustrated in the figures are schematic in nature, and their shapes are not intended to illustrate the precise shapes of the regions, and are not intended to limit the scope of the claims.

[0057] As used herein, "about" or "approximately" includes the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean that the deviation from the stated value is within one or more standard deviations, or within a range of ±10% or 5%.

[0058] The organometallic compound according to an embodiment is represented by Formula 1:

[0059] Formula 1

[0060] M(L 1 ) n1 (L 2 ) n2

[0061] In Formula 1, M may be a transition metal. For example, M may be selected from the first row transition metals, the second row transition metals, and the third row transition metals of the periodic table.

[0062] In one embodiment, M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0063] In one embodiment, M may be Ir, Pt, Os, or Rh, but embodiments of the present disclosure are not limited thereto.

[0064] In formula 1, L 1 It may be a ligand represented by Formula 2A. In Formula 1, n1 represents a group L 1 The number of L can be 1 or 2. When n1 is 2, the two groups L 1 Can be the same as or different from each other.

[0065] In formula 1, L 2 It may be a ligand represented by Formula 2B. In Formula 1, n2 represents a group L2 The number of L can be 1 or 2. When n2 is 2, the two groups L 2 Can be the same as or different from each other.

[0066]

[0067] Formulae 2A and 2B will be described below.

[0068] In formula 1, L 1 and L 2 Can be different from each other.

[0069] In one embodiment, M may be Ir, and the sum of n1 and n2 may be 3; or M may be Pt, and the sum of n1 and n2 may be 2.

[0070] In Formula 2A, X 1 It can be C, N, Si, or P. For example, X 1 It may be C, but the embodiments of the present disclosure are not limited thereto.

[0071] In Formulae 2A and 2B, ring CY 1 CY 2 , and ring CY 14 Can be independently C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.

[0072] For example, CY 1 CY 2 , and ring CY 14 may each independently be i) a first ring, ii) a second ring, iii) a fused ring in which at least two first rings are fused, iv) a fused ring in which at least two second rings are fused, or v) a fused ring in which at least one first ring and at least one second ring are fused, wherein

[0073] The first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, Azole group, iso Azole group, Oxadiazole group, isocyanate Oxadiazole group, Triazole group, iso a triazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiole group, a diazathiole group, or a triazathiole group, and

[0074] The second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0075] In one embodiment, cycloCY 1 CY 2 , and ring CY 14 can be independently selected from a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, Azabenzophosphoside group, azaindene group, azabenzosilole group, azabenzogermanol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborol group, azadibenzophosphoside group, azafluorene group, azadibenzosilole group, azadibenzogermanol group, azadibenzothiophene group , azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, Azole group, iso azole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo Azole group, benzothiazole group, benzo A oxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group, but the embodiments of the present disclosure are not limited thereto.

[0076] In one embodiment, cycloCY 1 CY 2 , and ring CY 14 Each may be independently selected from a phenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, and an azadibenzosilole group, but the embodiments of the present disclosure are not limited thereto.

[0077] In Formula 2B, R 1 -R 3 Can be independently C 1 -C 60 Alkyl or C 6 -C 60 Aryl, each of which is unsubstituted or substituted by at least one selected from the group consisting of 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, and C 1 -C 10 alkyl.

[0078] For example, R 1 -R 3 The tert-butyl radicals may be each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, phenyl, biphenyl, or naphthyl, each of which is unsubstituted or substituted by at least one radical selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF2 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, and C 1 -C 10 alkyl.

[0079] In one embodiment, R 1 -R 3 Can be independently -CH 3 、-CH 2 CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CD 3 , or -CD 2 CH 3 .

[0080] In Formula 2B, R 1 -R 3 Can be the same as or different from each other.

[0081] In one embodiment, R 1 -R 3 may be the same as each other, but the embodiments of the present disclosure are not limited thereto.

[0082] In Formulas 2A and 2B, Z 1 -Z 3 and R 11 -R 14 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60 heteroarylalkyl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 ), and -P(=O)(Q 8 )(Q 9 ), where R 12 can be neither hydrogen nor methyl, and Q 1 -Q 9 Same as described above.

[0083] In one embodiment, Z 1 -Z 3 and R 11 -R 14 Can be independently selected from:

[0084] 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;

[0085] Each of the following is substituted by at least one C 1 -C 20 Alkyl or C 1 -C 20Alkoxy: 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, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, or pyrimidinyl;

[0086] each being unsubstituted or substituted with at least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, 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, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH2 , 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, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, 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, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, and -Si(Q) 33 )(Q 34 )(Q 35 );and

[0087] -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ), where R 12 is neither hydrogen nor methyl, and

[0088] Q 1 -Q9 and Q 33 -Q 35 Can be independently selected from:

[0089] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;and

[0090] each being unsubstituted or substituted with at least one selected from the group consisting of n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl; 1 -C 10 Alkyl, and phenyl.

[0091] In one embodiment, in Formula 2B, R 12 You can choose from:

[0092] C 2 -C 20 Alkyl or C 2 -C 20 Alkoxy;

[0093] Each of the following is selected from at least one substituted methyl or methoxy group: 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 14 Aryl, C 1 -C 14heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;

[0094] Each of the following is substituted by at least one C 2 -C 20 Alkyl or C 2 -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, C 1 -C 10 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 14 Aryl, C 1 -C 14 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;

[0095] Each is unsubstituted or substituted by at least one selected from 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 14 Aryl, C 1 -C 14 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 14 Aryl, C 1 -C 14 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and

[0096] -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 ), or -P(=O)(Q 8 )(Q 9 ).

[0097] In one embodiment, in Formula 2B, R 12 You can choose from:

[0098] C 2 -C 20 Alkyl or C 2 -C 20 Alkoxy;

[0099] methyl or methoxy, each substituted with at least one selected from the group consisting of cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, phenyl, naphthyl, pyridinyl, and pyrimidinyl;

[0100] methyl or methoxy, each substituted with: i) at least one selected from cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, phenyl, naphthyl, pyridinyl, and pyrimidinyl, and ii) at least one deuterium;

[0101] Each of the following is substituted by at least one C 2 -C 20 Alkyl or C 2 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, phenyl, naphthyl, pyridinyl, and pyrimidinyl; and

[0102] each being unsubstituted or substituted with at least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, 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, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, 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, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, and azadibenzothiophenyl.

[0103] C 1 -C 60 Alkyl, C 1 -C 20 Alkyl, and C 1 -C 10Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, or tert-decyl, and C 1 -C 60 Alkoxy, C 1 -C 20 Alkoxy, and C 1 -C 10 Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group.

[0104] In one embodiment, in Formulae 2A and 2B, Z 1 -Z 3 , R 11 , R 13 , and R 14 can be independently selected from hydrogen, deuterium, -F, cyano, nitro, -SF 5 、-CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , a group represented by formula 9-1 to 9-66, a group represented by formula 9-1 to 9-66 in which at least one hydrogen is replaced by deuterium, a group represented by formula 10-1 to 10-249, a group represented by formula 10-1 to 10-249 in which at least one hydrogen is replaced by deuterium, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 ), and -Ge(Q 3 )(Q 4 )(Q 5 )(where Q 1 -Q 5 each independently the same as described above); and

[0105] R in Formula 2B 12 It can be selected from groups represented by formulae 9-1 to 9-66, groups represented by formulae 9-1 to 9-66 in which at least one hydrogen is replaced by deuterium, groups represented by formulae 10-1 to 10-249, and groups represented by formulae 10-1 to 10-249 in which at least one hydrogen is replaced by deuterium.

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113] In formulae 9-1 to 9-66 and 10-1 to 10-249, * represents a binding site with an adjacent atom, Ph represents a phenyl group, and TMS represents a trimethylsilyl group. As used herein, "a group represented by formulae 9-1 to 9-66 in which at least one hydrogen is replaced by deuterium" may be, for example, a group represented by formulae 9-501 to 9-552:

[0114]

[0115] As used herein, the “group represented by formulae 10-1 to 10-249 in which at least one hydrogen is replaced by deuterium” may be, for example, a group represented by formulae 10-501 to 10-510:

[0116]

[0117] In one embodiment, in Formula 2A, Z 1 can be selected from hydrogen, deuterium, -F, cyano, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 ), and -Ge(Q 3 )(Q 4 )(Q 5 ), where Q 1 -Q 5 Same as described above.

[0118] In formula 2A, a1 represents a group Z 1 When a1 is 2 or more, two or more groups Z 1 Can be the same as or different from each other.

[0119] In Formulae 2A and 2B, a2, a3, and b1 each represent a group Z 2 , Z 3 , and R 14 When a2 is 2 or more, two or more groups Z 2 may be the same as or different from each other. When a3 is 2 or greater, two or more groups Z 3 may be the same as or different from each other, and when b1 is 2 or greater, two or more groups R 14 For example, a2, a3, and b1 may each independently be an integer of 0-10, but the embodiments of the present disclosure are not limited thereto.

[0120] c1 can be an integer from 1 to 4, wherein when c1 is 2 or greater, two or more The groups represented by may be the same as or different from each other. For example, c1 may be 1 or 2.

[0121] In formulae 2A and 2B, i) is selected from a plurality of groups Z 1 Two or more groups of may be optionally linked to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group, ii) selected from a plurality of groups Z 2 Two or more groups of may be optionally linked to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 The heterocyclic group, iii) is selected from a plurality of groups Z 3 Two or more groups of may be optionally linked to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30Heterocyclic group, iv) R 12 and R 13 may be optionally linked to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 The heterocyclic group, v) is selected from a plurality of groups R 14 Two or more groups of may be optionally linked to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 A heterocyclic group, or vi) selected from the group Z 1 , Z 2 , and R 11 -R 14 Two or more groups of may be optionally linked to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Here, unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Examples of heterocyclic groups include each of which is unsubstituted or substituted with at least one R 10a a substituted phenyl group, a cyclopentane group, a cyclopentadienyl group, a bicyclo[2.2.1]heptane group, a furanyl group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuranyl group, a benzothiophene group, an indole group, or a benzosilole group, wherein R 10a With Z 1 The same definition applies. 5 -C 30 Carbocyclic groups and C 1 -C 30 The heterocyclic group will be described additionally below.

[0122] In Formulae 2A and 2B, * and *' each represent a binding site to M in Formula 1.

[0123] In one embodiment, in Formula 2A, The groups represented can be selected from groups Z which are each unsubstituted or substituted by a3 3 Substituted C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.

[0124] a3, Z 3 , and X 1 Same as described above.

[0125] In one embodiment, in Formula 2A, The groups represented can be selected from groups Z which are each unsubstituted or substituted by a3 3 Substituted phenyl, biphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl.

[0126] In one embodiment, in Formula 2A, The group represented may be a group represented by one selected from the group consisting of formulae CY1(1) to CY1(20):

[0127]

[0128] In formulas CY1(1) to CY1(20),

[0129] Z 3 Same as described above,

[0130] X 19 Can be O, S, N (Z 4 )、C(Z 4 )(Z5 ), or Si(Z 4 )(Z 5 ),

[0131] Z 4 and Z 5 Can be independently related to Z 3 Same as described,

[0132] a12 can be an integer from 0 to 2.

[0133] a13 can be an integer from 0 to 3.

[0134] a14 can be an integer from 0 to 4.

[0135] a15 can be an integer from 0 to 5.

[0136] a17 can be an integer from 0 to 7.

[0137] a19 can be an integer from 0 to 9, and

[0138] * indicates the binding site with the adjacent carbon atom.

[0139] In one embodiment, in Formula 2A, The group represented may be a group represented by one selected from Formulae 10-10(1) to 10-10(18) and 10-249:

[0140]

[0141] In formulas 10-10(1) to 10-10(18), Z 3a -Z 3e Can be independently related to Z 3 Same as described, where Z 3a -Z 3e It may not be hydrogen, and * indicates a bonding site with an adjacent carbon atom.

[0142] In one embodiment, in Formula 2A, The group represented may be selected from the groups represented by Formulae 10-1 to 10-249 and the groups represented by Formulae 10-1 to 10-249 in which at least one hydrogen is replaced by deuterium, but embodiments of the present disclosure are not limited thereto.

[0143] In one embodiment, in Formula 2A, The group represented may be a group represented by one selected from the group consisting of formulae CY1-1 to CY1-56:

[0144]

[0145]

[0146]

[0147] In formulas CY1-1 to CY1-56,

[0148] X 1 CY 1 , Z 3 , and a3 may each independently be the same as described herein,

[0149] Z 1a -Z 1d Can be independently related to Z 1 Same as described, where Z 1a -Z 1d It may not be hydrogen,

[0150] X 11 and X 12 Can be independently related to X 1 Same as described,

[0151] Cyclo 11 and CY 12 Can be independently related to the ring CY 1 Same as described,

[0152] Z 31 and Z 32 Can be independently related to Z 3 Same as described,

[0153] a31 and a32 may each independently be the same as described with respect to a3,

[0154] Cyclo 10a Can be C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0155] R 10a Same as described above,

[0156] aa can be an integer from 0 to 10, and

[0157] * represents the binding site with M in Formula 1, and *" represents the binding site with ring CY in Formula 2A. 2 binding site.

[0158] In one embodiment, in Formula 2A, The group represented may be a group represented by one selected from the group consisting of formulae CY2-1 to CY2-64:

[0159]

[0160]

[0161]

[0162]

[0163] In formulas CY2-1 to CY2-64,

[0164] Z 2 Same as described above,

[0165] X 22 Can be C(Z 22 )(Z 23 )、N(Z 22 ), O, S, or Si(Z 22 )(Z 23 ),

[0166] Z 22 -Z 29 Can be independently related to Z 2 Same as described,

[0167] a28 can be an integer from 0 to 8.

[0168] a26 can be an integer from 0 to 6.

[0169] a25 can be an integer from 0 to 5.

[0170] a24 can be an integer from 0 to 4.

[0171] a23 can be an integer from 0 to 3.

[0172] a22 can be an integer from 0 to 2.

[0173] *" represents the binding site to the carbon atom of the adjacent pyridine ring in Formula 2A, and

[0174] *' represents the binding site with M in Formula 1.

[0175] In one embodiment, in Formula 2A, The group represented may be a group represented by one selected from the group consisting of formulae CY2(1) to CY2(16):

[0176]

[0177] In formulas CY2(1) to CY2(16),

[0178] Z 2a -Z 2d Can be independently related to Z 2Same as described, where Z 2a -Z 2d It may not be hydrogen,

[0179] *" represents the binding site to the carbon atom of the adjacent pyridine ring in Formula 2A, and

[0180] *' represents the binding site with M in Formula 1.

[0181] In one embodiment, in Formula 2B, The group represented may be a group represented by one selected from the group consisting of formulae CY14-1 to CY14-64:

[0182]

[0183]

[0184]

[0185] In formulas CY14-1 to CY14-64,

[0186] R 14 Same as described above,

[0187] X 14 Can be C(R 1 )(R 2 )、N(R 1 ), O, S, or Si (R 1 )(R 2 ),

[0188] R 1 -R 8 Can be independently related to R 14 Same as described,

[0189] b18 can be an integer from 0 to 8.

[0190] b16 can be an integer from 0 to 6.

[0191] b15 can be an integer from 0 to 5.

[0192] b14 can be an integer from 0 to 4.

[0193] b13 can be an integer from 0 to 3.

[0194] b12 can be an integer from 0 to 2.

[0195] *" represents the binding site to the carbon atom of the adjacent pyridine ring in Formula 2B, and

[0196] *' represents the binding site with M in Formula 1.

[0197] In one embodiment, in Formula 2B, The group represented may be a group represented by one selected from the group consisting of formulae CY14(1) to CY14(16):

[0198]

[0199] In formulas CY14(1) to CY14(16),

[0200] R 14a -R 14d Can be independently related to R 14 Same as described, where R 14a -R 14d It may not be hydrogen,

[0201] *" represents the binding site to the carbon atom of the adjacent pyridine ring in Formula 2B, and

[0202] *' represents the binding site with M in Formula 1.

[0203] In one embodiment, the organometallic compound may be represented by Formula 1A:

[0204]

[0205]

[0206] In Formula 1A,

[0207] M, n1, n2, X 1 CY 1 , R 1 -R 3 , Z 3 , R 11 -R 13 , and c1 may each independently be the same as described herein,

[0208] T 11 Can be N, C(Z 1a ), or connected to the ring CY 1 Carbon, T 12 Can be N, C(Z 1b ), or connected to the ring CY 1 Carbon, T 13 Can be N, C(Z 1c ), or connected to the ring CY 1 Carbon, T 14 Can be N, C(Z 1d ), or connected to the ring CY 1 Carbon, selected from T 11 To T 14 At least one of the1 of carbon, and Z 1a -Z 1d Can be independently related to Z 1 Same as described,

[0209] T 21 Can be N or C(Z 2a ), T 22 Can be N or C(Z 2b ), T 23 Can be N or C(Z 2c ), T 24 Can be N or C(Z 2d ), and Z 2a -Z 2d Can be independently related to Z 2 Same as described,

[0210] T 31 Can be N or C(R 14a ), T 32 Can be N or C(R 14b ), T 33 Can be N or C(R 14c ), T 34 Can be N or C(R 14d ), and R 14a -R 14d Can be independently related to R 14 Same as described,

[0211] Group Z 1a -Z 1d Two or more of may be optionally linked to form an unsubstituted or substituted R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0212] Group Z 2a -Z 2d Two or more of may be optionally linked to form an unsubstituted or substituted R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0213] Two or more groups Z 3 may be optionally linked to form an unsubstituted or substituted with at least one R10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0214] R 12 and R 13 may be optionally linked to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0215] Group R 14a -R 14d Two or more of may be optionally linked to form an unsubstituted or substituted R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0216] Group Z 1a -Z 1d , Z 2a -Z 2d , R 11 -R 13 , and R 14a -R 14d Two or more of may be optionally linked to form an unsubstituted or substituted R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups, and

[0217] R 10a May be the same as described above.

[0218] In one embodiment, the organometallic compound represented by Formula 1 may satisfy at least one selected from Conditions 1 to 5:

[0219] Condition 1

[0220] Z in Formula 2A 1 Not-Si(Q 3 )(Q4 )(Q 5 )

[0221] Condition 2

[0222] In Formula 2A, Z 2 Not-Si(Q 3 )(Q 4 )(Q 5 )

[0223] Condition 3

[0224] Z in Formula 2A 3 Not-Si(Q 3 )(Q 4 )(Q 5 )

[0225] Condition 4

[0226] R in Formula 2B 11 -R 13 Wuyiwei-Si(Q 3 )(Q 4 )(Q 5 )

[0227] Condition 5

[0228] R in Formula 2B 14 Not-Si(Q 3 )(Q 4 )(Q 5 ).

[0229] In one embodiment, the number of silicon (Si) atoms in the organometallic compound represented by Formula 1 may be 1, 2, or 3.

[0230] In one embodiment, the number of silicon (Si) atoms in the organometallic compound represented by Formula 1 may be 1 or 2.

[0231] As used herein, the term “azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzosilole group, azabenzogermanol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermanol group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, and azadibenzothiophene 5,5-dioxide group” refers to an azadibenzothiophene 5,5-dioxide group. The “group” each refers to a heterocyclic group having the same structural skeleton as the respective structural skeletons of “indole group, benzoborole group, benzophosphole group, indene group, benzosilole group, benzogermanol group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzosilole group, dibenzogermanol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, and dibenzothiophene 5,5-dioxide group”, wherein at least one of the ring-forming carbons of the above rings is replaced by nitrogen.

[0232] For example, the organometallic compound may be one selected from Compounds 1 to 420, but embodiments of the present disclosure are not limited thereto:

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244] L in the organometallic compound represented by Formula 1 1 It can be a ligand represented by formula 2A, n1 is a group L 1 The number can be 1 or 2, L 2 It can be a ligand represented by formula 2B, n2 is a group L 2 The number can be 1 or 2, and L 1 and L 2 That is, the organometallic compound may be a heteroleptic complex mainly including at least one ligand represented by Formula 2A and at least one ligand represented by Formula 2B as ligands attached to the metal M.

[0245] Although not wishing to be bound by theory, since L in Eq. 2 The ligand represented by Formula 2B, therefore, the organometallic compound represented by Formula 1 may have a highest occupied molecular orbital (HOMO) energy level, a lowest unoccupied molecular orbital (LUMO) energy level, and T suitable for materials for electronic devices, such as materials for organic light-emitting devices. 1 Therefore, an electronic device including the organometallic compound represented by Formula 1, such as an organic light emitting device, may have excellent luminous efficiency and lifespan characteristics.

[0246] R in Formula 2B 12 Thus, the organometallic compound represented by Formula 1 can emit light shifted toward a relatively shorter wavelength, such as blue light, green light, or green-blue light, and an electronic device including the organometallic compound, such as an organic light-emitting device, can have excellent out-coupling efficiency and high emission efficiency.

[0247] In Formula 2B, the silyl group is bonded to the 5-position of the pyridine ring (see Formula 2B). Without wishing to be bound by theory, due to this bonding, the organometallic compound comprising the ligand represented by Formula 2B has excellent heat resistance and anti-decomposition properties. Therefore, electronic devices such as organic light-emitting devices comprising the organometallic compound have high stability during manufacturing, storage, and / or driving, and long life.

[0248] In addition, the pyridine ring in Formula 2A may be replaced by a number of c1 rings CY 1 Therefore, the orientation property of the organometallic compound represented by Formula 1 is improved, thereby providing high light emission efficiency to an electronic device including the organometallic compound, such as an organic light emitting device.

[0249] The highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, the singlet state (S) energy level of some of the organometallic compounds represented by Formula 1 were evaluated by using the Gaussian 09 program accompanied by optimization of the molecular structure according to the density functional theory (DFT) based on B3LYP. 1 ) energy level, and triplet state (T 1 The results are shown in Table 1, where each value is in electron volts (eV).

[0250] Table 1

[0251]

[0252] From Table 1, it was confirmed that the organometallic compound represented by Formula 1 had electrical characteristics suitable for use in electronic devices, for example, suitable for use as a dopant for an organic light-emitting device.

[0253] The synthesis method of the organometallic compound represented by Formula 1 can be understood by one of ordinary skill in the art by referring to the synthesis examples provided below.

[0254] The organometallic compound represented by Formula 1 is suitable for use in an organic layer of an organic light-emitting device, for example, suitable for use as a dopant in an emission layer of the organic layer. Therefore, another aspect provides an organic light-emitting device, comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and comprising an emission layer, the organic layer comprising at least one organometallic compound represented by Formula 1.

[0255] Due to including the organic layer including the organometallic compound represented by Formula 1, the organic light emitting device may have low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, low roll-off ratio, and excellent color purity.

[0256] The organic metal compound of Formula 1 can be used between the electrode pairs of the organic light-emitting device. For example, the organic metal compound represented by Formula 1 can be included in the emission layer. In this regard, the organic metal compound can act as a dopant, and the emission layer can further include a host (that is, the amount of the organic metal compound represented by Formula 1 is less than the amount of the host). The emission layer can emit, for example, green light or blue light.

[0257] The expression “(organic layer) includes at least one organic metal compound” used herein may include the case where “(organic layer) includes the same organic metal compound represented by Formula 1” and the case where “(organic layer) includes two or more different organic metal compounds represented by Formula 1”.

[0258] For example, the organic layer may include only Compound 1 as the organometallic compound. In this regard, Compound 1 may be present in the emission layer of the organic light-emitting device. In another embodiment, the organic layer may include Compound 1 and Compound 2 as the organometallic compound. In this regard, Compound 1 and Compound 2 may be present in the same layer (e.g., Compound 1 and Compound 2 may both be present in the emission layer).

[0259] 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.

[0260] In one embodiment, in the organic light-emitting device, the first electrode is an anode, and the second electrode is a cathode, and the organic layer further includes a hole transport region arranged between the first electrode and the emission layer and an electron transport region arranged between the emission layer and the second electrode, and the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0261] The term "organic layer" as used herein refers to a single layer and / or a plurality of layers between the first electrode and the second electrode of the organic light emitting device. The "organic layer" may further include an organic metal complex including a metal in addition to an organic compound.

[0262] Figure 1 FIG. 1 is a schematic diagram of an organic light emitting device 10 according to an embodiment. Figure 1 The structure of an organic light emitting device according to an embodiment and a method of manufacturing the organic light emitting device according to an embodiment are described. The organic light emitting device 10 includes a first electrode 11 , an organic layer 15 , and a second electrode 19 , which are sequentially stacked.

[0263] 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 a general organic light-emitting device 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, and water resistance.

[0264] The first electrode 11 may be formed, for example, 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 selected from materials 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 may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), and zinc oxide (ZnO). In one embodiment, 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 first electrode.

[0265] 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 110 is not limited thereto.

[0266] The organic layer 15 may be disposed on the first electrode 11 .

[0267] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0268] The hole transport region may be disposed between the first electrode 11 and the emission layer.

[0269] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0270] The hole transport region may include only one of the hole injection layer or the hole transport layer. In another embodiment, 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, which are sequentially stacked in the order stated in the direction extending from the first electrode 11.

[0271] The hole injection layer may be formed on the first electrode 11 by using one or more exemplary methods selected from vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) deposition.

[0272] When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the compound 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 about / second - approx. However, the deposition conditions are not limited thereto.

[0273] 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 after coating to remove the solvent may be about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

[0274] By referring to the conditions for forming the hole injection layer, the conditions for forming the hole transport layer and the electron blocking layer can be understood.

[0275] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by the following Formula 201, and a compound represented by the following Formula 202:

[0276]

[0277]

[0278] Ar in Formula 201 101 and Ar 102 Can be independently selected from:

[0279] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthenylene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyren ... phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene phenylene, tetraphenylene, perylenene, and pentacene; and

[0280] Each of the following is selected from at least one substituted phenylene, pentalene, indenylene, naphthylene, azulenylene, heptalene, acenaphthene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenyl ... phenanthrenylene, fluorenylene, benzo[9,10]phenan phenylene, tetraphenylene, perylene, and pentphenylene: 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 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkyl, C 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, or a monovalent non-aromatic fused heteropolycyclic group.

[0281] In Formula 201, xa and xb may each independently be an integer of 0 to 5, or may be 0, 1, or 2. For example, xa is 1 and xb is 0, but xa and xb are not limited thereto.

[0282] R in formula 201 and 202 101 -R 108 , R 111 -R 119 , and R 121 -R 124 Can be independently selected from:

[0283] 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.);

[0284] Each of the following is substituted by at least one 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, or phosphoric acid group or its salt;

[0285] phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl; and

[0286] phenyl, naphthyl, anthracenyl, fluorenyl, and pyrenyl, each of which is selected from at least one substituted group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 Alkyl, or C 1 -C 10 Alkoxy,

[0287] However, the implementation of the present disclosure is not limited thereto.

[0288] R in Formula 201 109 You can choose from:

[0289] phenyl, naphthyl, anthracenyl, or pyridyl; and

[0290] phenyl, naphthyl, anthracenyl, and pyridyl groups, each of which is selected from at least one substituted group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, naphthyl, anthracenyl, or pyridyl.

[0291] In one embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments of the present disclosure are not limited thereto:

[0292]

[0293] R in Formula 201A 101 , R 111 , R 112 , and R 109 This can be understood by referring to the description provided herein.

[0294] 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.

[0295]

[0296]

[0297]

[0298] The thickness of the hole transport region may be about 100 angstroms. -about For example, about -about When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about -about and for example about -about and the thickness of the hole transport layer may be in the range of about -about and 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.

[0299] 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.

[0300] The charge generating material may be, for example, a p-dopant. The p-dopant may be one selected from a quinone derivative, a metal oxide, and a compound containing a cyano group, but the embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are quinone derivatives such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and compounds containing a cyano group such as the following compound HT-D1, but are not limited thereto.

[0301]

[0302] The hole transport region may include a buffer layer.

[0303] In an embodiment, 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.

[0304] In an embodiment, the emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied when forming the hole injection layer, although the deposition or coating conditions may vary depending on the compound used to form the emission layer.

[0305] In an embodiment, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be selected from the materials for the hole transport region described above and the materials for the host to be described later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be mCP, which will be described later.

[0306] The emission layer may include a host and a dopant, and the dopant may include an organic metal compound represented by Formula 1.

[0307] The host may include at least one selected from TPBi, TBADN, ADN (also known as "DNA"), CBP, CDBP, TCP, mCP, and compounds H50 to H52:

[0308]

[0309] 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 an embodiment, 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.

[0310] When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.

[0311] The thickness of the emission layer may be about -about For example, about -about When the thickness of the emission layer is within this range, excellent light emitting characteristics can be obtained without a significant increase in driving voltage.

[0312] Then, an electron transport region may be disposed on the emission layer.

[0313] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0314] For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a multilayer structure including two or more different materials or a single layer structure.

[0315] The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region may be understood by referring to the conditions for forming the hole injection layer.

[0316] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAlq, but embodiments of the present disclosure are not limited thereto.

[0317]

[0318] 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 improved hole blocking capability without a significant increase in driving voltage.

[0319] The electron transport layer may further include BCP, Bphen, Alq 3 , BAlq, TAZ, and NTAZ.

[0320]

[0321] In one embodiment, the electron transport layer may include at least one selected from ET1 to ET25, but is not limited thereto:

[0322]

[0323]

[0324] 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.

[0325] In addition, the electron transport layer may further include a material including a metal in addition to the materials described above.

[0326] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (8-hydroxyquinolate lithium, LiQ) or ET-D2.

[0327]

[0328] The electron transport region may include an electron injection layer that facilitates the flow of electrons from the second electrode 19 thereinto.

[0329] The electron injection layer may include a material selected from LiF, NaCl, CsF, Li 2 At least one of O and BaO.

[0330] The thickness of the electron injection layer can be about -about 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.

[0331] The second electrode 19 may be disposed on the organic layer 15. The second electrode 19 may be a cathode. The material for forming the second electrode 19 may be selected from metals, alloys, conductive compounds, or combinations 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 the material for forming the second electrode 19. In one embodiment, 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.

[0332] Another aspect of the present disclosure provides a diagnostic composition comprising at least one organometallic compound represented by Formula 1.

[0333] The organometallic compound represented by Formula 1 provides high luminescence efficiency. Therefore, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.

[0334] The diagnostic compositions can be used in a variety of applications including diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0335] In the above, the organometallic compound has been described, such as reference Figure 1 An organic light emitting device, and a diagnostic composition including the organometallic compound are described, but embodiments of the present disclosure are not limited thereto.

[0336] 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 C1 -C 60 Alkyl is a divalent group of the same structure.

[0337] As used herein, the term "C 1 -C 60 "Alkoxy" refers to a 101 The monovalent group represented by 101 C 1 -C 60 The term "alkyl" refers to an alkyl radical, and non-limiting examples thereof include methoxy, ethoxy, and isopropoxy.

[0338] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, and examples thereof include ethenyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0339] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminal of the 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.

[0340] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. 3 -C 10 "Cycloalkylene" refers to a cycloalkylene having a 3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0341] As used herein, the term "C 1 -C 10"Heterocycloalkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si and S 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 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0342] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0343] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, P, Si and S as a ring atom, 1 to 10 carbon atoms, and at least one 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.

[0344] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C 6 -C 60 Aryl and C 6 -C 60When the arylene groups each include two or more rings, the rings may be fused to each other.

[0345] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si and S as a ring atom and 1 to 60 carbon atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si, and S as a ring atom and 1 to 60 carbon atoms. 1 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.

[0346] The term "C 6 -C 60 "Aryloxy" means -OA 102 (A 102 C 6 -C 60 aryl), and C 6 -C 60 Arylthio represents -SA 103 (A 103 C 6 -C 60 aryl).

[0347] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8-60 carbon atoms) having two or more rings fused to each other, having only carbon atoms as ring-forming atoms, and not having aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic fused polycyclic group include fluorenyl. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.

[0348] 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 heteroatoms selected from N, O, P, Si and S as ring-forming atoms in addition to carbon atoms, and having no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic group include carbazolyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.

[0349] 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.

[0350] As used herein, the term "C 1 -C 30 The term "heterocyclic group" refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, Si, P and S 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.

[0351] 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 6 -C 60 Aryloxy, substituted C 6 -C60 Arylthio, substituted C 7 -C 60 Arylalkyl, substituted C 1 -C 60 Heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 Heteroarylthio, substituted C 2 -C 60 The heteroaralkyl group, the substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of the substituted monovalent non-aromatic fused heteropolycyclic group may each independently be:

[0352] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy;

[0353] Each of the following is substituted by at least one C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10Cycloalkenyl, 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, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 ), and -P(=O)(Q 18 )(Q 19 );

[0354] 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 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60 a heteroaralkyl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group;

[0355] Each of the following is substituted by at least one C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60 heteroarylalkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ), and -P(=O)(Q 28 )(Q 29 );or

[0356] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 ), or -P(=O)(Q 38 )(Q 39 ),and

[0357] As used here, Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 can be independently selected from 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, 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, selected from 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 60Arylthio, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.

[0358] When a group containing the specified number of carbon atoms is substituted with any of the groups listed in the preceding paragraph, the number of carbon atoms in the resulting "substituted" group is defined as the sum of the carbon atoms contained in the original (unsubstituted) group plus the carbon atoms contained in the substituent, if any. 1 -C 30 "Alkyl" refers to a C 6 -C 30 Aryl substituted C 1 -C 30 When the alkyl group is substituted with an aryl group, the total number of carbon atoms in the resulting aryl-substituted alkylene group is C 7 -C 60 .

[0359] As used herein, the expressions * and *' each denote a binding site to an adjacent atom unless otherwise specified.

[0360] 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 B used is the same as the amount of A used in terms of molar equivalents.

[0361] Example

[0362] Synthesis Example 1 (Compound 13)

[0363] Synthesis of compound 13A

[0364]

[0365] 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine (8.0 grams (g), 28.2 millimoles (mmol)) and iridium chloride trihydrate (4.4 g, 12.5 mmol) were mixed with 120 mL of ethoxyethanol and 40 mL of distilled water and stirred for 24 hours under reflux, and the reaction mixture was cooled to room temperature. The solid produced thereby was filtered, separated, and washed thoroughly with water, methanol, and hexane in sequence. The solid was dried in a vacuum oven to obtain 5.5 g (55% yield) of compound 13A.

[0366] Synthesis of compound 13B

[0367]

[0368] Compound 13A (1.7g, 1.0mmol) and 45mL dichloromethane (MC) are mixed, and AgOTf (0.54g, 2.1mmol) is dissolved in 15mL methanol and added thereto.Then, reaction mixture is stirred for 18 hours at room temperature under the state of blocking light with aluminum foil therein.Remove the solid produced by filtering reaction mixture via using diatomite, and filtrate is evaporated under reduced pressure to obtain solid (compound 13B), which is used for next reaction without additional purification.

[0369] Synthesis of compound 13

[0370]

[0371] Compound 13B (1.8 g, 1.9 mmol) and 5-methyl-2,4-diphenylpyridine (0.6 g, 2.3 mmol) were mixed with 40 mL of ethanol and stirred at reflux for 18 hours, and the reaction mixture was cooled. The mixture obtained therefrom was filtered to obtain a solid. The solid was fully washed with ethanol and hexane, and column chromatography was performed with a dichloromethane:hexane solvent system to obtain 0.8 g (41% yield) of compound 13. Compound 13 was confirmed by high resolution mass spectrometry (HRMS) and HPLC analysis.

[0372] HRMS (matrix-assisted laser desorption ionization (MALDI)): for C 54 H 62 Ir 3 Si 2 Calculated value: m / z 1001.4112, found value: 1001.4107.

[0373] Synthesis Example 2 (Compound 163)

[0374]

[0375] 0.6 g (32% yield) of Compound 163 was obtained in the same manner as for the synthesis of Compound 13 of Synthesis Example 1, except that 2,4-diphenyl-5-(trimethylsilyl)pyridine was used instead of 5-methyl-2,4-diphenylpyridine. Compound 163 was confirmed by HRMS and HPLC analysis.

[0376] HRMS (MALDI): For C 56 H 68 Ir 3 Si 3 Calculated value: m / z 1059.4350, found: 1059.4358.

[0377] Synthesis Example 3 (Compound 193)

[0378]

[0379] 0.9 g (yield 47%) of compound 193 was obtained in the same manner as for compound 13 of Synthesis Example 1, except that 2-(dibenzo[b,d]furan-2-yl)-5-methyl-4-phenylpyridine was used instead of 5-methyl-2,4-diphenylpyridine. Compound 193 was confirmed by HRMS and HPLC analysis.

[0380] Synthesis Example 4: Synthesis of Compound 358

[0381] Synthesis of compound 358A

[0382]

[0383] 3.2 g (52% yield) of Compound 358A was obtained in the same manner as for the synthesis of Compound 13A of Synthesis Example 1, except that 4-(cyclopentylmethyl-D2)-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine. Compound 358A was confirmed by HRMS and HPLC analysis.

[0384] Synthesis of compound 358B

[0385]

[0386] Compound 358B was obtained in the same manner as used to synthesize Compound 13B of Synthesis Example 1, except that Compound 358A was used instead of Compound 13A. Compound 358B was used in the next reaction without additional purification.

[0387] Synthesis of compound 358

[0388]

[0389] 0.5 g (yield of 26%) of compound 358 was obtained in the same manner as for compound 13 of Synthesis Example 1, except that compound 358B was used instead of compound 13B, and 4-(isopropylphenyl)-5-methyl-2-phenylpyridine was used instead of 5-methyl-2,4-diphenylpyridine. Compound 358 was confirmed by HRMS and HPLC analysis.

[0390] HRMS (MALDI): For C 61 H 68 D 4 Ir 3 Si 2Calculated value: m / z 1099.5145, found: 1099.5152.

[0391] Synthesis Example 5: Synthesis of Compound 371

[0392]

[0393] 0.7 g (37% yield) of Compound 371 was obtained in the same manner as for the synthesis of Compound 13 of Synthesis Example 1, except that 4-methyl-D3-2,5-diphenylpyridine was used instead of 5-methyl-2,4-diphenylpyridine. Compound 371 was confirmed by HRMS and HPLC analysis.

[0394] HRMS (MALDI): For C 60 H 64 Ir 3 Si 2 Calculated value: m / z 1091.4217, found: 1091.4210.

[0395] Example 1

[0396] ITO / Ag / ITO were deposited on it. The glass substrate as an anode was cut into a size of 50 mm×50 mm×0.5 mm, ultrasonically treated with isopropyl alcohol and deionized water for 5 minutes each, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the glass substrate was provided to a vacuum deposition device.

[0397] N-(2-naphthyl)-N',N'-di{4-[2-naphthyl(phenyl)amino]phenyl}-N-phenyl-1,4-phenylenediamine (2-TNATA) was vacuum deposited on the anode to form a A hole injection layer having a thickness of 1000 Å was formed, and 4,4′-di[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum deposited on the hole injection layer to form a The hole transport layer has a thickness of .

[0398] Then, 9,9'-(4,4'-biphenyldiyl)bis(9H-carbazole) (CBP) (host) and compound 13 (dopant) were co-deposited on the hole transport layer at a weight ratio of 98:2 to form a The thickness of the emission layer.

[0399] Then, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) was vacuum deposited on the emission layer to form a The thickness of the hole blocking layer is Alq 3Vacuum deposition is performed on the hole blocking layer to form a An electron transport layer having a thickness of , LiF is vacuum deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Mg and Ag are co-deposited on the electron injection layer at a weight ratio of 90:10 to form a A cathode with a thickness of is provided, thereby completing the manufacture of the organic light-emitting device.

[0400]

[0401] Examples 2 to 5 and Comparative Examples A and B

[0402] An organic light-emitting device was manufactured in the same manner as in Example 1, except that in forming the emission layer, the compounds shown in Table 2 were each used instead of Compound 13 as a dopant.

[0403] Evaluation Example 2: Evaluation of Characteristics of Organic Light-Emitting Device

[0404] The driving voltage (volt, V), the maximum value (maximum EQE) of the external quantum efficiency (%), the roll-off ratio, the half width (FWHM) of the main peak of the electroluminescence (EL) spectrum (nanometers, nm), the maximum emission wavelength (nm), and the lifetime (T 97 ), and the results are shown in Table 2. An ammeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation equipment. Lifespan (T 97 ) (at 3,500 nits or 3,500 candelas / square meter) represents the amount of time (hours, h) that elapses when the brightness is 97% of the initial brightness (100%), and is expressed as a relative value (%). The roll-off ratio is calculated by using Equation 20:

[0405] Equation 20

[0406] Roll-off ratio = {1-(efficiency (at 3,500 nits) / maximum emission efficiency)}×100%

[0407] Table 2

[0408]

[0409] Dopant Compounds:

[0410]

[0411] From Table 2, it is confirmed that the organic light emitting devices of Examples 1 to 5 have improved driving voltage, external quantum efficiency, roll-off ratio, and lifespan characteristics compared to those of the organic light emitting devices of Comparative Examples A and B.

[0412] Since the organometallic compound has excellent electrical properties and heat resistance, an electronic device including the organometallic compound, such as an organic light-emitting device, can have improved driving voltage, current density, efficiency, power, color purity, and / or life characteristics. In addition, since the organometallic compound has excellent phosphorescent properties, a diagnostic composition with high diagnostic efficiency can be provided by using the organometallic compound.

[0413] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects in each embodiment should typically be considered as available for other similar features or aspects in other embodiments.

[0414] Although embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the following claims.

Claims

1. An organometallic compound represented by formula 1: Formula 1 M(L1) n1 (L2) n2 , in, In formula 1, M is Ir, L1 is a ligand represented by formula 2A, n1 is 1 or 2, wherein when n1 is 2, the two groups L1 are the same or different from each other, L2 is a ligand represented by formula 2B, n2 is 1 or 2, wherein when n2 is 2, the two groups L2 are the same or different from each other, The sum of n1 and n2 is 3, and L1 and L2 are different from each other: Wherein, in Formulas 2A and 2B, X1 is C, Ring CY1 is a phenyl group, Ring CY2 is a benzene group, a dibenzothiophene group, or a dibenzofuran group, Cyclo 14 is a phenyl group, R1-R3 are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, or tert-decyl, each of which is unsubstituted or substituted with at least one substituted radical selected from deuterium, -CD3, -CD2H, -CDH2, and C1-C 10 alkyl, Z1-Z3, R 11 , and R 13 -R 14 Each independently selected from: Hydrogen, Deuterium, C1-C 20 Alkyl, or C1-C 20 Alkoxy; and Each of the following C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -CD3, -CD2H, -CDH2, or C1-C 10 alkyl, R 12 is neither hydrogen nor methyl, and R 12 for: C2-C 20 Alkyl or C2-C 20 Alkoxy; methyl or methoxy groups each substituted with at least one selected from the group consisting of cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and phenyl; methyl or methoxy groups each substituted with: i) at least one selected from cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and phenyl, and ii) at least one deuterium; and Each of the following C2-C 20 Alkyl or C2-C 20 Alkoxy: deuterium, -CD3, -CD2H, -CDH2, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and phenyl, a1 is an integer of 0-3, wherein when a1 is 2 or more, two or more groups Z1 are the same or different from each other, c1 is 1, * and *' in Formula 2A and 2B each represent a binding site with M in Formula 1, Depend on The group represented is a group represented by the formula CY1(1): Among them, in formula CY1(1), Z3 is the same as described above, a15 is an integer from 0 to 5, and * indicates the binding site with the adjacent carbon atom, In formula 2A, The group represented is a group represented by one selected from the group consisting of formulae CY2-1, CY2-26, and CY2-27: Among them, in formulas CY2-1, CY2-26, and CY2-27, Z2 is the same as described above, X 22 is O or S, a26 is an integer from 0 to 6. a24 is an integer from 0 to 4. *" represents the binding site to the carbon atom of the adjacent pyridine ring in Formula 2A, and *' represents the binding site with M in Formula 1, and In formula 2B, The group represented is a group represented by the formula CY14-1: Among them, in formula CY14-1, R 14 Same as described above, b14 is an integer from 0 to 4. *" represents the binding site to the carbon atom of the adjacent pyridine ring in Formula 2B, and *' represents the binding site with M in Formula 1.

2. The organometallic compound according to claim 1, wherein In Formula 1, n1 is 1, and n2 is 2.

3. The organometallic compound according to claim 1, wherein In formula 2A, The group represented is a group represented by the formula CY2-1.

4. The organometallic compound according to claim 1, wherein In Formulas 2A and 2B, Z1-Z3, R 11 , R 13 , and R 14 Each independently selected from hydrogen, deuterium, -CH3, -CD3, -CD2H, -CDH2, a group represented by formula 9-1 to 9-33, and a group represented by formula 9-1 to 9-33 in which at least one hydrogen is replaced by deuterium, and R in Formula 2B 12 Selected from the groups represented by the formulae 9-1 to 9-36, 9-44 to 9-46, 9-54 to 9-56, and 9-64 to 9-66, and the groups represented by the formulae 9-1 to 9-36, 9-44 to 9-46, 9-54 to 9-56, and 9-64 to 9-66 in which at least one hydrogen is replaced by deuterium: In formulae 9-1 to 9-36, 9-44 to 9-46, 9-54 to 9-56, and 9-64 to 9-66, * represents a binding site with an adjacent atom.

5. The organometallic compound according to claim 1, wherein In Formula 2A, Z1 is selected from hydrogen, deuterium, and unsubstituted C1 alkyl.

6. The organometallic compound according to claim 1, wherein In formula 2A, The group represented is a group represented by one selected from the formulae CY1-1 to CY1-32: in, In formulas CY1-1 to CY1-32, X1, ring CY1, Z3, and a3 are each independently the same as described in claim 1, Z 1a -Z 1d Each independently the same as described in claim 1 with respect to Z1, wherein Z 1a -Z 1d Not hydrogen, * represents the binding site with M in Formula 1, and *" indicates the binding site to ring CY2 in Formula 2A.

7. The organometallic compound according to claim 1, wherein The organometallic compound is represented by Formula 1A: Formula 1A in, In Formula 1A, M, n1, n2, X1, R1-R3, R 11 -R 13 , c1, and by The groups represented are each independently the same as described in claim 1, T 11 C(Z 1a ) or connected to the carbon of ring CY1, T 12 C(Z 1b ) or connected to the carbon of ring CY1, T 13 C(Z 1c ) or connected to the carbon of ring CY1, T 14 C(Z 1d ) or a carbon connected to ring CY1, selected from T 11 -T 14 One of Z is connected to the carbon of ring CY1, and Z 1a -Z 1d Each independently the same as described in claim 1 with respect to Z1, T 21 C(Z 2a ), T 22 C(Z 2b ), T 23 C(Z 2c ), T 24 C(Z 2d ), and Z 2a -Z 2d Each independently the same as described in claim 1 with respect to Z2, T 31 C(R 14a ), T 32 C(R 14b ), T 33 C(R 14c ), T 34 C(R 14d ), and R 14a -R 14d Each independently of the above in claim 1 with respect to R 14 Same as described, The bond between N and M is a coordination bond, and The bond between C and M is a covalent bond.

8. The organometallic compound according to claim 1, wherein The organometallic compound is one selected from the following compounds:

9. Organic light-emitting device, comprising: a first electrode; a second electrode; as well as an organic layer disposed between the first electrode and the second electrode and including an emission layer, The organic layer comprises at least one organic metal compound as claimed in any one of claims 1 to 8.

10. The organic light emitting device according to claim 9, wherein The first electrode is an anode, The second electrode is a cathode, The organic layer further includes a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

11. The organic light emitting device according to claim 9, wherein The emissive layer includes the at least one organometallic compound.

12. The organic light emitting device according to claim 11, wherein The emissive layer further includes a host, and an amount of the host is greater than an amount of the at least one organometallic compound.

13. A diagnostic composition comprising an organometallic compound as claimed in any one of claims 1 to 8.

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