Organometallic compound, organic light emitting device including the same, and electronic device including the organic light emitting device

Abstract

Disclosed are organometallic compounds, organic light emitting devices including the same, and electronic devices including the organic light emitting devices. The organometallic compounds are represented by Formula 1, wherein M1 is a first row transition metal of the periodic table, a second row transition metal of the periodic table, or a third row transition metal of the periodic table, Ln1 is a bidentate ligand, n1 is 0, 1, or 2, and Ln2 is a ligand represented by Formula 1A, wherein A1, A2, Y1, Y2, R1-R3, R 10 , R 20 , b10, and b20 are as provided herein, and * and *' each represent a binding site with an adjacent atom. Formula 1 M1(Ln1) n1 (Ln2) 3‑n1 Formula 1A

Description

[0001] Cross Reference to Related Applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0122432, filed on September 22, 2020, in the Korean Intellectual Property Office, and all the benefits accruing therefrom, the contents of which are incorporated herein in their entirety by reference. TECHNICAL FIELD

[0003] One or more embodiments of the present disclosure relate to an organometallic compound, an organic light emitting device including the same, and an electronic device including the organic light emitting device. BACKGROUND

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

[0005] In an example, an organic light emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region can be disposed between the anode and the emission layer, and an electron transport region can be disposed between the emission layer and the cathode. Holes provided from the anode can move toward the emission layer through the hole transport region, and electrons provided from the cathode can move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state to thereby generate visible light. SUMMARY

[0006] An organometallic compound, an organic light emitting device including the same, and an electronic device including the organic light emitting device are provided.

[0007] Additional aspects will be set forth in part in the description which follows, and in part will become apparent to those skilled in the art upon examination of the following description, or can be learned by practice of the presented embodiments of the disclosure.

[0008] According to an aspect of one or more embodiments, an organometallic compound is provided by Formula 1:

[0009] Formula 1

[0010] M1(Ln1) n1 (Ln2) 3-n1

[0011] Formula 1A

[0012]

[0013] Formula 1-1

[0014]

[0015] wherein, in formula 1,

[0016] M1is a first row transition metal of the periodic table, a second row transition metal of the periodic table, or a third row transition metal of the periodic table,

[0017] Ln1is a bidentate ligand,

[0018] n1is 0, 1, or 2, and

[0019] Ln2is a ligand represented by formula 1A, and

[0020] in formulae 1A and 1-1,

[0021] A1, A3, and A4 are each independently C5-C 30 carbocyclic group or C1-C 30 heterocyclic group,

[0022] A2is: (i) a 6-membered carbocyclic group or a 6-membered heterocyclic group, or (ii) a bicyclic or polycyclic C5-C 30 carbocyclic group including a 6-membered carbocyclic group, or a bicyclic or polycyclic C1-C 30 heterocyclic group including at least one of a 6-membered carbocyclic group and a 6-membered heterocyclic group,

[0023] Y1is C or N, and Y2is C or N,

[0024] R1, R2, and R3are each independently a group represented by formula 1-1, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C1-C 60 alkylthio group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C7-C 60 aralkyl group, a substituted or unsubstituted C1-C60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroalkyl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0025] At least one of R1, R2, and R3 is a group represented by formula 1-1.

[0026] R 10 R 20 R 30 and R 40 Each of the following groups is independently 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, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroalkyl, substituted or unsubstituted C2-C 60Alkyl heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0027] R 10 R 20 R 30 and R 40 At least two adjacent groups are optionally linked together to form a substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,

[0028] b10 and b20 are each independent integers from 1 to 10.

[0029] b30 and b40 are each independent integers from 1 to 10.

[0030] When A1 is a phenyl group, (i) R with a quantity of b20 20 At least one of them is a substituted or unsubstituted C1-C 60 Alkyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3), and / or (ii) R1 or R2 are groups represented by formula 1-1.

[0031] * and *' represent the binding sites with adjacent atoms, and

[0032] Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C7-C 60 Aryl groups, substituted C1-C 60 heteroaryl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60heteroaryl thiols, substituted C2-C 60 Heteroalkyl, substituted C2-C 60 At least one substituent of the alkyl heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group is:

[0033] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy;

[0034] Each of the C1-Cs is replaced by one or more of the following: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroalkyl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q)16 (Q) 17 -P(=O)(Q8)(Q9), or -P(Q8)(Q9);

[0035] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heterocyclic group;

[0036] Each of the C3-Cs is replaced by one or more of the following: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroalkyl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 ), or -P(Q 28 (Q) 29 );as well as

[0037] -Si(Q 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 )-P(=O)(Q 38 (Q) 39 ), or -P(Q 38 (Q) 39 ),

[0038] Among them, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each of the following groups is independently 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, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroalkyl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic group, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic group.

[0039] According to another aspect of the embodiment, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emitting layer, wherein the organic layer comprises at least one organometallic compound as provided herein.

[0040] The organometallic compounds provided herein may be included in the emission layer of the organic layer, and the organometallic compounds included in the emission layer may act as dopants.

[0041] According to another aspect of the embodiment, an electronic device including an organic light-emitting device as described herein is provided. Attached Figure Description

[0042] By combination Figure 1 The above and other aspects, features, and advantages of some embodiments of this disclosure will become clearer from the following description. Figure 1 This shows a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments. Detailed Implementation

[0043] Exemplary embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals always refer to the same elements. In this respect, the exemplary embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the exemplary embodiments are described below in more detail only to illustrate aspects, with reference to the accompanying drawings. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. Expressions such as “at least one of” modify the entire list of elements when preceding or following it, without modifying any individual element of the list.

[0044] It will be understood that when an element is referred to as being "on" another element, it may be in direct contact with said other element or there may be an intermediate element between them. Conversely, when an element is referred to as being "directly on" another element, there is no intermediate element.

[0045] It will be understood that although the terms first, second, third, etc., may be used herein to describe various elements, components, regions, layers, and / or portions, these elements, components, regions, layers, and / or portions should not be limited by these terms. These terms are used only to distinguish one element, component, region, layer, or portion from another. Therefore, without departing from the teachings of this embodiment, the first element, component, region, layer, or portion discussed below may be referred to as the second element, component, region, layer, or portion.

[0046] 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” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0047] The term "or" means "and / or". It will be further understood that the terms "comprising" or "including", when used in this specification, indicate the presence of the stated features, areas, integrals, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more additional features, areas, integrals, steps, operations, elements, components, and / or collections thereof.

[0048] Unless otherwise defined, all terms used herein (including technical and scientific terms) 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 common dictionaries, should be interpreted as having meanings consistent with their context in the relevant field and in the present disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly defined herein.

[0049] Exemplary embodiments are described herein with reference to cross-sectional views that serve as schematic diagrams of one or more idealized embodiments. Thus, deviations from the shapes shown in the figures will be anticipated as a result of, for example, manufacturing techniques and / or tolerances. Therefore, the embodiments described herein should not be construed as limited to the specific shapes of the regions illustrated herein, but rather include deviations in shape caused, for example, by manufacturing processes. For example, regions illustrated or described as flat may typically have rough and / or non-linear characteristics. Furthermore, sharp corners in the figures 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 nor to limit the scope of the claims.

[0050] As used herein, “about” or “approximately” includes the stated value and means within an acceptable range of deviation from the specific value, as determined by a person skilled in the art taking into account the measurement in question and the errors associated with the measurement of the specific quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations relative to the stated value, or within ±10% or 5%.

[0051] One aspect of this disclosure provides organometallic compounds represented by Formula 1:

[0052] Formula 1

[0053] M1(Ln1) n1 (Ln2) 3-n1

[0054] In Equation 1, M1 represents the transition metal in the first row of the periodic table, the transition metal in the second row of the periodic table, or the transition metal in the third row of the periodic table.

[0055] In one or more embodiments, M1 may be beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), iridium (Ir), osmium (Os), platinum (Pt), or gold (Au).

[0056] In one or more embodiments, M1 may be Ir, Os, Pt, Pd, or Au.

[0057] In one or more embodiments, M1 may be Ir.

[0058] In Equation 1, Ln1 can be a bidentate ligand.

[0059] In Equation 1, n1 can be 0, 1, or 2.

[0060] In Equation 1, Ln2 can be a ligand represented by Equation 1A:

[0061] Formula 1A

[0062]

[0063] Equation 1-1

[0064]

[0065] In equations 1A and 1-1, A1, A3, and A4 can each be independently represented as C5-C. 60 Carbocyclic groups or C1-C 60 Heterocyclic groups.

[0066] For example, A1, A3, and A4 can each independently be i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused together, iv) a fused ring in which two or more second rings are fused together, or v) a fused ring in which one or more first rings and one or more second rings are fused together.

[0067] The first ring may be a cyclopentyl group, a cyclopentadienyl group, a furan group, a thiophene group, a pyrrole group, a thiophene group, an indole group, a benzofuran group, a benzothiophene group, an indole group, or a benzothiophene group. azole group, iso- azole group, diazole group, isodiazole group diazole group, Triazole group, iso Triazole group, thiazole group, isothiazole group, thiadiazole group, isothiazole group, thiatriazole group, isothiazole group, pyrazole group, imidazole group, triazole group, tetraazole group, azathiophene group, diazathiophene group, or triazathiophene group, and

[0068] The second ring may be an adamantyl group, norbornene group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptane (norbornene) group, bicyclo[2.2.2]octyl group, cyclohexyl group, cyclohexene group, phenyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group.

[0069] In one or more embodiments, A1, A3, and A4 may each independently be a phenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, etc. Groups, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, pyrrole group, cyclopentadienyl group, thiophene group, borocyclopentadienyl group, phosphacyclopentadienyl group, selenophene group, germanium heterocyclopentadienyl group, benzothiophene group, benzofuran group, indole group, indene group, benzothiophene group, benzoboron heterocyclopentadienyl group, benzophosphacyclopentadienyl group, benzoselenophene group, benzogermanium heterocycle Pentadiene group, dibenzothiophene group, dibenzofuran group, carbazole group, fluorene group, dibenzothiophene group, dibenzoborone heterocyclopentadiene group, dibenzophosphonone heterocyclopentadiene group, dibenzoselenophene group, dibenzogermanium heterocyclopentadiene group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azibabenzothiophene group, azibabenzofuran group, Azaindole group, azaindenyl group, azabenzothiophene group, azabenzoborone heterocyclopentadienyl group, azabenzophosphacyclopentadienyl group, azabenzoselenophene group, azabenzogermanium heterocyclopentadienyl group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzothiophene group, azadibenzoborone heterocyclopentadienyl group, azadibenzophosphacyclopentadienyl group Azadibenzoselenophene group, azadibenzogermanium heterocyclopentadiene 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, phenanthrene-rhein group, pyrazole group, imidazole group, triazole group azole group, iso- azole group, thiazole group, isothiazole group, Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo[] azole group, benzothiazole group, benzo[] The diazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, adamantyl group, norbornene group, or norbornene group.

[0070] In one or more embodiments, A1 may be a phenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a benzothiophene group, a benzofuran group, an indole group, an indole group, a benzothiophene group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzothiophene group.

[0071] In one or more embodiments, A1 may be a phenyl group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzothiophene group.

[0072] In Formula 1A, A2 can be: (i) a 6-membered carbon ring group or a 6-membered heterocyclic group, or (ii) a bicyclic or polycyclic C5-C group including a 6-membered carbon ring group. 30 A bicyclic or polycyclic C1-C ring group, or including at least one of a 6-membered carbocyclic group and a 6-membered heterocyclic group. 30 Heterocyclic groups.

[0073] In one or more embodiments, A2 may be an azibazothiophene group, an azibazofuran group, an azibaindol group, an azibazoindene group, an azibazothiophene group, an azibazoboranecyclopentadiene group, an azibazophosphacyclopentadiene group, an azibazoselenophene group, an azibazogeronanecyclopentadiene group, an azibadibenzothiophene group, an azibadibenzofuran group, an azibacarbazole group, an azibafluorene group, an azibadibenzothiophene group, an azibadibenzoboranecyclopentadiene group, or an azibadibenzothiophene group. Phosphacyclopentadiene group, azidobenzylselenene group, azidobenzgeranium azidocyclopentadiene group, azidobenzthiophene 5-oxide group, azido-9H-fluorene-9-one group, azidobenzthiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, 5,6,7,8-tetrahydroisoquinoline group, or 5,6,7,8-tetrahydroquinoline group.

[0074] In one or more embodiments, A2 may be a pyridine group, pyrimidine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, or phenanthrene group.

[0075] In one or more embodiments, A3 and A4 may each independently be a phenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a benzothiophene group, a benzofuran group, an indole group, an indole group, a benzothiophene group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzothiophene group.

[0076] In one or more embodiments, A3 and A4 may each be independently a phenyl group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzothiophene group.

[0077] In Equation 1A, Y1 can be C or N, and Y2 can be C or N.

[0078] In Equations 1 and 1A, the bond between M1 and Y1 can be a covalent bond or a coordinate bond.

[0079] In Equations 1 and 1A, the bond between M1 and Y2 can be a covalent bond or a coordinate bond.

[0080] In one or more embodiments, Y1 can be C, Y2 can be N, the bond between M1 and Y1 can be a covalent bond, and the bond between M1 and Y2 can be a coordinate bond.

[0081] In Formula 1A, R1, R2, and R3 can each independently be a group represented by Formula 1-1, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroalkyl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), and

[0082] At least one of R1, R2, and R3 may be a group represented by formula 1-1.

[0083] In one or more embodiments, R1, R2, and R3 can each be independently:

[0084] Groups represented by Formula 1-1;

[0085] 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, phosphate group or its salt, -SF5, C1-C 20 Alkyl, C2-C 20 alkenyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio;

[0086] Each of the C1-Cs is replaced by one or more of the following: 20 Alkyl, C2-C 20 alkenyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel (bicyclo[2.2.1]heptyl), norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20 alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, or pyrimidinyl,

[0087] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20 alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, or azadibenzothiophenyl; or

[0088] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0089] Q1-Q9 can be independently defined as follows:

[0090] Deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, - OR

[0091] Each of the following groups, either unsubstituted or substituted with one or more of the following: 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: deuterium, -F, C1-C 10 Alkyl, or phenyl, and

[0092] At least one of R1, R2, and R3 may be a group represented by formula 1-1.

[0093] In one or more embodiments, R1, R2, and R3 may each independently be a group represented by Formula 1-1, hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 Alkylphenyl, naphthyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3),

[0094] At least one of R1, R2, and R3 may be a group represented by formula 1-1.

[0095] In one or more embodiments, any one of R1-R3 may be a group represented by formula 1-1.

[0096] For example, R2 can be a group represented by formula 1-1, and R1 and R3 can each be hydrogen.

[0097] In equations 1A and 1-1, R 10 R 20 R 30 and R 40 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroalkyl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9).

[0098] In equations 1A and 1-1, R 10 R 20 R 30 and R 40 Each can be independently:

[0099] 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, phosphate group or its salt, -SF5, C1-C 20 Alkyl, C2-C 20 alkenyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio;

[0100] Each of the C1-Cs is replaced by one or more of the following: 20 Alkyl, C2-C 20 alkenyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel (bicyclo[2.2.1]heptyl), norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, or pyrimidinyl;

[0101] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20 alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, or azadibenzothiophenyl; or

[0102] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), or -B(Q6)(Q7),

[0103] Q1-Q3 and Q6-Q7 can be independently defined as follows:

[0104] Deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, - OR

[0105] Each of the following groups, either unsubstituted or substituted with one or more of the following: 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: deuterium, -F, C1-C 10 Alkyl or phenyl.

[0106] In Equation 1A, b10 represents R 10 The quantity, and can be an integer from 1 to 10. In Equation 1A, b20 represents R. 20 The quantity can be an integer from 1 to 10.

[0107] In Equation 1-1, b30 represents R 30 The quantity, and can be an integer from 1 to 10. In Equation 1-1, b40 represents R. 40 The quantity can be an integer from 1 to 10.

[0108] In one or more embodiments, R 10 R 20 R 30 and R 40 Each can be independently represented by a group of one of formulas 9-1 to 9-43, 9-201 to 9-237, 10-1 to 10-129, or 10-201 to 10-350:

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116] In formulas 9-1 to 9-43, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, * indicates a binding site with an adjacent atom, Ph is phenyl, TMS is trimethylsilyl, and TMG is trimethylgermanyl.

[0117] In Equation 1A, when A1 is a phenyl group, (i) the number of R is b20. 20 At least one of them may be a substituted or unsubstituted C1-C 60 Alkyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3), and / or (ii) R1 or R2 may be groups represented by formula 1-1.

[0118] In Equation 1-1, * represents the binding site with the adjacent atom in Equation 1.

[0119] In one or more embodiments, R 20 It can be hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 Alkylphenyl, naphthyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3).

[0120] In Equation 1A, * and *' each represent a binding site with an adjacent atom.

[0121] In equations 1A and 1-1, R 10 R 20 R 30 and R 40 At least two adjacent groups may optionally be linked together to form a substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0122] In one or more embodiments, R 10 R 20 R 30 and R 40 At least two adjacent groups may optionally be linked together via a single bond, a double bond, or a first linking group to form an unsubstituted or linked group with at least one R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30Heterocyclic groups (e.g., each unsubstituted or with at least one R) 10a Substituted fluorene groups, thallium groups, acridine groups, etc.), wherein R 10a Can be related to R 10 The same as described, except for R 10a Not other than hydrogen.

[0123] The first linking group may be *-N(R8)-*', *-B(R8)-*', *-P(R8)-*', *-C(R8)(R9)-*', *-Si(R8)(R9)-*', *-Ge(R8)(R9)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R8)=*', *=C(R8)-*', *-C(R8)=C(R9)-*', *-C(=S)-*', or *-C≡C-*', wherein R8 and R9 may each be linked with respect to R 10 The descriptions are identical, and * and *' each represent a binding site with an adjacent atom.

[0124] In one or more embodiments, Ln1 may be represented by one of Equations 8-1 to 8-12, or in one or more embodiments, Ln1 may be represented by Equation 5:

[0125]

[0126] Formula 5

[0127]

[0128] In Equation 5,

[0129] A5 and A6 can each be independently classified as C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups,

[0130] Y5 can be C or N, and Y6 can be C or N.

[0131] R 50 and R 60 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroalkyl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), wherein Q1-Q3 and Q6-Q9 are the same as described above.

[0132] b50 and b60 can each be an integer from 1 to 10 independently, and

[0133] * and *' each represent a binding site with an adjacent atom.

[0134] In one or more embodiments, A5 may be a pyridine group, pyrimidine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthrene-rhein group, pyrazole group, triazole group, imidazole group, indole group, benzopyrazole group, or benzimidazole group.

[0135] In one or more embodiments, A6 may be a phenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a benzothiophene group, a benzofuran group, an indole group, an indole group, a benzothiophene group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzothiophene group.

[0136] In one or more embodiments, Y5 can be N, and Y6 can be C.

[0137] The key between M1 and Y5 can be a coordinate key, and

[0138] The bond between M1 and Y6 can be a covalent bond.

[0139] In one or more embodiments, R 50 and R 60 Each can be independently related to R 10 R 20 R 30 、or R 40 The description is the same.

[0140] In one or more embodiments, Ln1 may be one of Equations 5-1 to 5-116:

[0141]

[0142]

[0143]

[0144]

[0145] Among them, in equations 5-1 to 5-116,

[0146] R 51 -R 53 Each of these groups can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 Alkyl, or C1-C 20 Alkoxy;

[0147] Each of the C1-Cs is replaced by one or more of the following: 20 Alkyl or C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 20 Alkylphenyl, naphthyl, pyridyl, or pyrimidinyl;

[0148] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 20Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl;

[0149] Each of the following substituted groups is cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 20 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 20Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, Triazinyl, Dibenzofuranyl, Dibenzothiophenyl, Dibenzothiophenyl, Benzocarbazoyl, Dibenzocarbazoyl, Imidazolylpyridyl, Imidazolylpyrimidinyl, -Si(Q) 11 (Q) 12 (Q) 13 -B(Q) 16 (Q) 17 ), or -N(Q 14 (Q) 15 );or

[0150] -Si(Q1)(Q2)(Q3), -B(Q6)(Q7), or -N(Q4)(Q5),

[0151] Among them, Q1-Q7 and Q 11 -Q 17 Each can be independently:

[0152] Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 alkylphenyl, or naphthyl; and

[0153] Each of the following is a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, or naphthyl group, each substituted with one or more of deuterium or phenyl groups.

[0154] In equations 5-1 to 5-116, b51 and b54 can each be 1 or 2 independently;

[0155] b53 and b55 can each be 1, 2, or 3 independently;

[0156] b52 can be 1, 2, 3, or 4;

[0157] Ph can be phenyl;

[0158] Ph-d5 could be a phenyl group in which each hydrogen atom is replaced by deuterium; and

[0159] * and *' each represent a binding site with an adjacent atom.

[0160] In one or more embodiments, the organometallic compound may be a compound represented by one of formulas 11-1 to 11-3:

[0161] Formula 11-1

[0162]

[0163] Formula 11-2

[0164]

[0165] Formula 11-3

[0166]

[0167] Among them, in equations 11-1 to 11-3,

[0168] M1, n1, A2, R1, R2, R3, R 10 R 20 b10 and b20 can each be the same as those described in this article.

[0169] A 11 It can be a phenyl group, an indole group, a benzofuran group, a benzothiophene group, or a benzothiophene group.

[0170] b11 can be 1, 2, 3, 4, 5, or 6.

[0171] R 11 and R 12 Each can be independently related to R 10 The same as described.

[0172] A5 and A6 can each be independently classified as C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups,

[0173] R 50 and R 60 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroalkyl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), wherein Q1-Q3 and Q6-Q9 are the same as described above, and

[0174] b50 and b60 can each be an integer from 1 to 10 independently.

[0175] In equations 11-1 and 11-2, (i) the number of R is b20. 20 At least one of them may be a substituted or unsubstituted C1-C 60 Alkyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3), and / or (ii) R1 or R2 may be groups represented by formula 1-1.

[0176] In one or more embodiments, the organometallic compound may be represented by formula 12-1:

[0177] Equation 12-1

[0178]

[0179] In Equation 12-1,

[0180] M1, n1, A1, R1, R2, R3, R 10 b10 and b20 can each be the same as those described in this article.

[0181] R 21 -R 24 Each can be independently related to R 20 The same as described.

[0182] A5 and A6 can each be independently classified as C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups,

[0183] R 50 and R 60 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroalkyl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), wherein Q1-Q3 and Q6-Q9 are the same as described above, and

[0184] b50 and b60 can each be an integer from 1 to 10 independently.

[0185] In Equation 12-1, when A1 is a phenyl group, (i)R 21 -R 24 At least one of them may be a substituted or unsubstituted C1-C 60 Alkyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3), and / or (ii) R1 or R2 may be groups represented by formula 1-1.

[0186] In one or more embodiments, in formula 12-1, when A1 is a phenyl group, (i)R 22 and R 23 At least one of them may be a substituted or unsubstituted C1-C 60 Alkyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3), and / or (ii) R1 or R2 may be groups represented by formula 1-1.

[0187] In one or more embodiments, the organometallic compound may be represented by one of formulas 21-1 to 21-5:

[0188]

[0189] Among them, in equations 21-1 to 21-5,

[0190] M1, n1, and R1-R3 can each be the same as those described in this paper.

[0191] X1 can be O, S, N(R) 15 ), C(R 15 (R) 16 ), or Si(R) 15 (R) 16 ),

[0192] R 11 -R 16 Each can be independently related to R 10 The same as described.

[0193] R 21 -R 24 Each can be independently related to R 20 The same as described.

[0194] R 51 -R 54 Each can be independently related to R 50 The same as described, and

[0195] R 61 -R64 Each can be independently related to R 60 The description is the same.

[0196] In equations 21-1 and 21-2, (i)R 21 -R 24 At least one of (e.g., R) 22 and R 23 At least one of them may be substituted or unsubstituted C1-C 60 Alkyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3), and / or (ii) R1 or R2 may be groups represented by formula 1-1.

[0197] In one or more embodiments, in formulas 21-3 to 21-5, R1 or R2 may be a group represented by formula 1-1.

[0198] In one or more embodiments, each ligand Ln2 in Formula 1 can be independently represented by one of Formulas 2-1 to 2-27:

[0199]

[0200]

[0201] Among them, in equations 2-1 to 2-27,

[0202] X1 can be O, S, N(R) 15 ), C(R 15 (R) 16 ), or Si(R) 15 (R) 16 ),

[0203] R 15 and R 16 Each can be independently related to R 10 The same as described.

[0204] R 22 and R 23 Each can be independently C1-C 20 Alkyl, -Si(Q) 51 (Q) 52 (Q) 53 ), or -Ge(Q 51 (Q) 52 (Q) 53 ),

[0205] Q 51 -Q 53 Each can be independently C1-C 20 alkyl,

[0206] R31 -R 34 Each can be independently related to R 30 The same as described.

[0207] R 41 -R 44 Each can be independently related to R 40 The same as described, and

[0208] * and *' each represent the binding site with M1.

[0209] In one or more embodiments, the organometallic compound may not include an amine group.

[0210] While not wishing to be bound by specific theories, the electron-donating effect is enhanced when an amine group is substituted into A2, which is the portion relating to the lowest unoccupied molecular orbital (LUMO) energy level of the organometallic compound represented by Formula 1. Consequently, the emission wavelength of the organometallic compound can become longer, making it difficult to exhibit the desired emission wavelength with high color purity (e.g., a pure green emission wavelength). Furthermore, since the amine group exhibits melting properties during the deposition process of the organometallic compound, such a material can be very easily degraded, leading to a deterioration in the characteristics of the formed organic light-emitting device.

[0211] In this specification, TMS stands for *-Si(CH3)3, and TMG stands for *-Ge(CH3)3.

[0212] In one or more embodiments, the organometallic compound represented by Formula 1 may be one of compounds 1 to 36:

[0213]

[0214]

[0215] In Formula 1, at least one of R1, R2, and R3 can be a group represented by Formula 1-1. Additionally, when A1 in Formula 1A is a phenyl group, (i) the number of R groups is b20. 20 At least one of them may be a substituted or unsubstituted C1-C 60 Alkyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3), and / or (ii) R1 or R2 may be groups represented by formula 1-1.

[0216] Without being bound by theory, by introducing a heterogroup (e.g., a carbazole group) represented by Formula 1-1 into an organometallic compound represented by Formula 1, the heterogroup (e.g., a carbazole group) can supply a large number of π electrons to A1 (which is the part of the ligand represented by Formula 1A involving the highest occupied molecular orbital (HOMO) energy level), and organic light-emitting devices using the organometallic compound can have high luminous efficiency and excellent thermal stability.

[0217] Therefore, electronic devices, including organometallic compounds represented by Formula 1, such as organic light-emitting devices, can exhibit low driving voltage, high efficiency, long lifetime, and reduced roll-off.

[0218] The HOMO (electron volts, eV), LUMO (eV), S1 (eV), and T1 (eV) levels of some organometallic compounds represented by Equation 1 were evaluated using the Gaussian 09 program, which is accompanied by molecular structure optimization obtained through density functional theory (DFT) based on B3LYP. The results are shown in Table 1.

[0219] Table 1

[0220] Compound No. HOMO (eV) LUMO (eV) [S1 (eV)] [T1 (eV)] Compound 1 -4.868 -1.341 2.883 2.563 Compound 3 -4.942 -1.398 2.850 2.487 Compound 4 -4.938 -1.402 2.836 2.476 Compound 20 -4.946 -1.365 2.882 2.504 Compound C -4.866 -1.607 2.800 2.535 Compound D -4.896 -1.502 2.829 2.553

[0221]

[0222] Table 1 confirms that the organometallic compounds represented by Formula 1 possess electrical properties suitable for use as dopants in electronic devices such as organic light-emitting devices.

[0223] In one or more embodiments, the half-width (FWHM) of the emission peak of the emission spectrum or electroluminescence spectrum of the organometallic compound may be equal to or less than about 55 nanometers (nm). For example, the FWHM of the emission peak of the emission spectrum or electroluminescence spectrum of the organometallic compound may be about 30 nm to about 55 nm, about 40 nm to about 53 nm, or about 45 nm to about 52 nm.

[0224] In one or more embodiments, the maximum emission wavelength (emission peak wavelength, λ) of the emission spectrum or electroluminescence spectrum of the organometallic compound is... 最大 The wavelength can be approximately 500nm to approximately 600nm.

[0225] The method for synthesizing the organometallic compound represented by Formula 1, as described in the following synthetic examples, is readily apparent to those skilled in the art.

[0226] In this regard, organometallic compounds represented by Formula 1 are suitable for use in the organic layer of an organic light-emitting device, for example, as dopants in the emitting layer of the organic layer. Therefore, another aspect of this disclosure 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 emitting layer, wherein the organic layer comprises at least one organometallic compound represented by Formula 1.

[0227] Since the organic light-emitting device has an organic layer comprising an organometallic compound represented by Formula 1 as described above, it can obtain excellent characteristics in terms of driving voltage, current efficiency, external quantum efficiency, roll-off ratio and lifetime, and the FWHM of the emission peak of the EL spectrum can be relatively narrow.

[0228] The organometallic compound of Formula 1 can be used between the electrode pairs of the organic light-emitting device. For example, the organometallic compound represented by Formula 1 can be included in the emitting layer. In this respect, the organometallic compound can act as a dopant, and the emitting layer can further include a host (i.e., the amount of the organometallic compound represented by Formula 1 in the emitting layer is less than the amount of the host).

[0229] In one or more embodiments, the emitting layer may emit green light. For example, the emitting layer may emit green light having a maximum emission wavelength of about 500 nm to about 600 nm.

[0230] As used herein, the expression “(organic layer) comprises at least one organometallic compound represented by Formula 1” can include cases where “(organic layer) comprises the same organometallic compound represented by Formula 1” and cases where “(organic layer) comprises two or more different organometallic compounds represented by Formula 1”.

[0231] In one or more embodiments, the organic layer may include only compound 1 as the organometallic compound. In this embodiment, compound 1 may be included in the emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may include both compound 1 and compound 2 as the organometallic compound. In this embodiment, compound 1 and compound 2 may exist in the same layer (e.g., both compound 1 and compound 2 may be present in the emitting layer).

[0232] The first electrode may be the anode of the hole injection electrode and the second electrode may be the cathode of the electron injection electrode; or the first electrode may be the cathode of the electron injection electrode and the second electrode may be the anode of the hole injection electrode.

[0233] For example, in the organic light-emitting device, the first electrode may be an anode and the second electrode may be a cathode, and the organic layer may further include a hole transport region between the first electrode and the emitting layer and an electron transport region between the emitting layer and the second electrode, wherein 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, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0234] As used herein, the term "organic layer" refers to a single layer or multiple layers between the first and second electrodes of an organic light-emitting device. In addition to organic compounds, the "organic layer" may also include organometallic complexes containing metals.

[0235] Figure 1 This is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Hereinafter, regarding... Figure 1 The present disclosure describes the structure of an organic light-emitting device according to one or more embodiments and a method for manufacturing an organic light-emitting device according to one or more embodiments. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19 sequentially stacked.

[0236] A substrate may be disposed below the first electrode 11 or above the second electrode 19. For the substrate used, any substrate available in the art for use in organic light-emitting devices may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each possessing excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0237] In one or more embodiments, the first electrode 11 can be formed by depositing or sputtering a material for forming the first electrode 11 onto the substrate. The first electrode 11 can be an anode. The material for forming the first electrode 11 can include a material having a high work function to facilitate hole injection. The first electrode 11 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. In one or more embodiments, the material for forming the first electrode 11 can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 can be a metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0238] The first electrode 11 may have a single-layer structure or a multi-layer structure comprising two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO.

[0239] The organic layer 15 is disposed on the first electrode 11.

[0240] The organic layer 15 may include a hole transport region, an emitter layer, and an electron transport region.

[0241] The hole transport region can be arranged between the first electrode 11 and the emitter layer.

[0242] 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.

[0243] In one or more embodiments, the hole transport region may include a hole injection layer only or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the layers in each structure are stacked sequentially from the first electrode 11 in the order stated herein.

[0244] When the hole transport region includes a hole injection layer, the hole injection layer can be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, tape casting, and / or Langmuir-Broguet (LB) deposition.

[0245] When a hole injection layer is formed by vacuum deposition, the deposition conditions can be varied depending on the compound used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer. For example, deposition conditions may include a deposition temperature in the range of about 100°C to about 500°C, and a deposition temperature in the range of about 10°C. -8 To-10 -3 Vacuum pressure within the range of Torr, and in The deposition rate is within a certain range. However, deposition conditions are not limited to this.

[0246] When the hole injection layer is formed by spin coating, the coating conditions can be varied depending on the compound used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer. For example, coating conditions may include a coating speed in the range of about 2,000 rpm to about 5,000 rpm, and a temperature for heat treatment after coating to remove the solvent in the range of about 80°C to about 200°C. However, the coating conditions are not limited to these.

[0247] By referring to the conditions used to form the hole injection layer, the conditions used to form the hole transport layer and the electron blocking layer can be understood.

[0248] The hole transport region may include, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-sulfonylstyrene) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-sulfonylstyrene) (PANI / PSS), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(4,4′-(N-(4-sec-butylphenyl)diphenylamine)] (TFB), compounds represented by Formula 201, compounds represented by Formula 202, or any combination thereof:

[0249]

[0250]

[0251] Formula 201

[0252]

[0253] Formula 202

[0254]

[0255] In Equation 201, Ar 101 and Ar 102 Each can be independently substituted or substituted with one or more of the following: phenylene, cyclopentadienylene, indenylene, naphthylene, azuleylene, heptadienylene, acenaphtheylene, fluoreneylene, phenenylene, phenanthrene, anthraceneylene, fluoranthraceneylene, benzo[9,10]phenanthrene, pyreneylene, etc. alkyl, tetraphenylene, terephthalyl, perylene, or pentaphenylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60Arylthio, C7-C 60 Aryl alkyl, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heterocyclic group.

[0256] In Equation 201, xa and xb can each be an integer from 0 to 5, or 0, 1, or 2. For example, xa can be 1 and xb can be 0, but the implementation is not limited to this.

[0257] In equations 201 and 202, R 101 -R 108 R 111 -R 119 and R 121 -R 124 Each can be independently:

[0258] 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, phosphate group or its salt, C1-C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), or C1-C 10 Alkyl groups (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);

[0259] Each of the C1-Cs that has not been replaced or has been replaced by one or more of the following: 10 Alkyl or C1-C 10 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, or phosphate group or its salt; or

[0260] Each of the following groups—either unsubstituted or substituted with one or more of the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, or C1-C 10 Alkyl group.

[0261] In Equation 201, R 109It can be phenyl, naphthyl, anthracene, or pyridyl, respectively, either unsubstituted or substituted with the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, anthraceneyl, pyridyl, or any combination thereof.

[0262] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A:

[0263] Formula 201A

[0264]

[0265] In Equation 201A, R 101 R 111 R 112 and R 109 Each can be the same as described in this article.

[0266] For example, the hole transport region may include one of compounds HT1 to HT21, or any combination thereof:

[0267]

[0268]

[0269]

[0270] The thickness of the hole transport region can be For example Within the range. When the hole transport region includes at least one hole injection layer and a hole transport layer, the thickness of the hole injection layer can be within the range of... For example Within the range, and the thickness of the hole transport layer can be For example Within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage when the hole transport region, hole injection layer, and thickness of the hole transport layer are within these ranges.

[0271] In addition to these materials, the hole transport region may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0272] The charge-generating material may be, for example, a p-doper. The p-doper may include quinone derivatives, metal oxides, compounds containing a cyano group, or any combination thereof, but embodiments of this disclosure are not limited thereto. For example, the p-doper may be: quinone derivatives such as tetracyanoquinone dimethylane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethylane (F4-TCNQ), or F6-TCNNQ; metal oxides such as tungsten oxide and molybdenum oxide; compounds containing a cyano group such as compound HT-D1 or F12; or any combination thereof.

[0273]

[0274]

[0275] The hole transport region may include a buffer layer.

[0276] Furthermore, the buffer layer can compensate for the optical resonance distance according to the wavelength of the light emitted from the emission layer, and thus the efficiency of the formed organic light-emitting device can be improved.

[0277] Meanwhile, when the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may include the material for the hole transport region as described above, the host material as described below, or any combination thereof. For example, when the hole transport region includes an electron blocking layer, mCP, compound HT21, or any combination thereof may be used as the material for forming the electron blocking layer.

[0278] The emitter layer can then be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emitter layer is formed by vacuum deposition or spin coating, although the deposition or coating conditions may vary depending on the material used to form the emitter layer, the deposition or coating conditions may be similar to those applied when forming the hole injection layer.

[0279] The emitter layer may include a host and a dopant, and the dopant may include an organometallic compound represented by Formula 1 as described herein.

[0280] The main body may include TPBi, TBADN, ADN (also known as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, compound H52, compound 53, compound 54, or any combination thereof:

[0281]

[0282]

[0283] In one or more embodiments, when the organic light-emitting device is a full-color organic light-emitting device, the emitting layer may be patterned as a red emitting layer, a green emitting layer, and / or a blue emitting layer. In one or more embodiments, due to the stacked structure including red, green, and / or blue emitting layers, the emitting layer can emit white light.

[0284] When the emitter layer comprises a substrate and a dopant, the amount of the dopant may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the substrate, but the embodiments of this disclosure are not limited thereto.

[0285] The thickness of the emission layer can be For example Within these ranges, excellent light-emitting characteristics can be obtained without a significant increase in driving voltage when the thickness of the emitting layer is within these ranges.

[0286] Then, the electron transmission region can be arranged on the emission layer.

[0287] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0288] 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. The electron transport layer may have a multilayer structure or a single-layer structure comprising two or more different materials.

[0289] By referring to the conditions for forming the hole injection layer, the conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region can be understood.

[0290] When the electron transport region includes a hole blocking layer, the hole blocking layer may include at least one of, for example, BCP, Bphen, and BAlq.

[0291]

[0292] The hole blocking layer may include the main body, a material for forming an electron injection layer (described later), a material for forming an electron transport layer, or any combination thereof.

[0293] The thickness of the hole-blocking layer can be... For example Within these ranges, excellent hole blocking characteristics can be obtained without a significant increase in driving voltage when the thickness of the hole blocking layer is within these ranges.

[0294] In one or more embodiments, the electron transport layer may include BCP, Bphen, TPBi, Alq3, BAlq, TAZ, NTAZ, or any combination thereof:

[0295]

[0296] In one or more embodiments, the electron transport layer may include one of compounds ET1 to ET25, or any combination thereof:

[0297]

[0298]

[0299] The thickness of the electron transport layer can be For example Within these ranges, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage when the thickness of the electron transport layer is within these ranges.

[0300] Furthermore, in addition to the materials described above, the electron transport layer may further include a material comprising metal.

[0301] The metal-containing material may include a Li complex. The Li complex may include, for example, compounds ET-D1 or ET-D2.

[0302]

[0303] Additionally, the electron transport region may include an electron injection layer that facilitates the inflow of electrons from the second electrode 19 therein.

[0304] The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.

[0305] The thickness of the electron injection layer can be For example Within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage when the thickness of the electron injection layer is within these ranges.

[0306] The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a metal, alloy, conductive compound, or a combination thereof having a relatively low work function. For example, the material used to form the second electrode 19 may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag). For the fabrication of a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the material for forming the second electrode 19.

[0307] In the previous text, it has been referenced Figure 1 Organic light-emitting devices have been described, but embodiments of the present disclosure are not limited thereto.

[0308] In one or more embodiments, the organic light-emitting device may be included in an electronic device. Therefore, another aspect of this disclosure provides an electronic device including the organic light-emitting device. The electronic device may include, for example, a display, a lighting device, a sensor, etc.

[0309] Another aspect of this disclosure provides a diagnostic composition comprising at least one organometallic compound represented by Formula 1.

[0310] Organometallic compounds represented by Formula 1 provide high luminescence efficiency. Therefore, diagnostic compositions comprising said organometallic compounds can have high diagnostic efficiency.

[0311] The diagnostic composition can be used in a variety of applications, including diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0312] As used in this article, the term "C1-C" 60 "Alkyl" refers to a straight-chain or branched monovalent group of a saturated aliphatic hydrocarbon having 1-60 carbon atoms, and as used herein in the term "C1-C". 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Divalent groups with the same structure as alkyl groups.

[0313] C1-C 60 Alkyl, C1-C 20 Alkyl, and / or C1-C 10 Examples of alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl alkyl, or tert-decyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, or any combination thereof. For example, formula 9-33 is a branched C6 alkyl group, such as tert-butyl substituted with two methyl groups.

[0314] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and examples of them are methoxy, ethoxy, propoxy, butoxy, and pentoxy.

[0315] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed by the carbon atoms in the C2-C2 group. 60 A hydrocarbon group formed by substituting at least one carbon-carbon double bond into the middle or end of an alkyl group, examples of which are vinyl, propenyl, and butenyl. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to a group with a C2-C ratio. 60 Divalent groups with the same structure as alkenyl groups.

[0316] As used in this article, the term "C2-C" 60 "Alkyne" refers to the group formed by the combination of C2-C... 60 A hydrocarbon group formed by substituting at least one carbon-carbon triple bond into the middle or end of an alkyl group, examples of which are ethynyl and propynyl. As used herein, the term "C2-C" is used in this context. 60 "Alynyl group" refers to a group with a C2-C group. 60 Divalent groups with the same structure as alkynyl groups.

[0317] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3-10 carbon atoms, and as used herein, "C3-C" 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Divalent groups with the same structure as cycloalkyl groups.

[0318] C3-C 10 Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornel), bicyclo[2.2.2]octyl, etc.

[0319] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monocyclic group comprising at least one heteroatom selected from N, O, P, Si, and S as a cyclic atom and 1-10 carbon atoms, and as used herein by the term "C1-C". 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with the same structure as heterocyclic alkyl groups.

[0320] C1-C10 Examples of heterocyclic alkyl groups are silylcyclopentyl, silylcyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, and tetrahydrothiophenyl.

[0321] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3-10 carbon atoms and at least one carbon-carbon double bond in its ring and lacking aromaticity, and examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also relevant. 10 "Cyclopentene" refers to a group with a C3-C6 bond structure. 10 A divalent group with the same structure as a cycloalkenyl group.

[0322] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, P, Si, and S as a cyclic atom, 1-10 carbon atoms, and at least one carbon-carbon double bond in its ring. C1-C 10 Examples of heterocyclic alkenyl groups are 2,3-dihydrofuranyl and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to a group that has a C1-C2 bond structure. 10 Divalent groups with the same structure as heterocyclic alkenyl groups.

[0323] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system with 6-60 carbon atoms, and as used herein, "C6-C". 60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system with 6-60 carbon atoms. (C6-C) 60 Examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and... Base. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the two or more rings may be fused together.

[0324] As used in this article, the term "C7-C" 60 "Alkyl" refers to an aryl group formed by at least one C1-C2 group. 59 Alkyl-substituted C6-C 59 Aryl.

[0325] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a cyclic aromatic system having at least one heteroatom selected from N, O, P, Si, and S as a cyclic atom and 1-60 carbon atoms, and as used herein by the term "C1-C".60 "Hypo-heteroaryl" refers to a divalent group having the following cyclic aromatic system: the cyclic aromatic system has at least one heteroatom selected from N, O, P, Si, and S as the cyclic atom and 1-60 carbon atoms. C1-C 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C6-C... 60 heteroaryl and C6-C 60 When each heteroaryl group comprises two or more rings, the two or more rings may fused together.

[0326] The term "C2-C" used in this article 60 "alkyl heteroaryl" refers to an alkyl group formed by at least one C1-C2 group. 59 Alkyl-substituted C1-C 59 Mixed aromatic compounds.

[0327] As used in this article, the term "C6-C" 60 "Aryloxy group" represents -OA 102 (where A) 102 Indicates C6-C 60 Aryl), as used herein by the term "C6-C 60 "Arylthio" indicates -SA 103 (where A) 103 Indicates C6-C 60 Aryl), and as used herein, the term "C1-C 60 "alkylthio" indicates -SA 104 (where A) 104 Indicates C1-C 60 alkyl).

[0328] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8-60 carbon atoms) that has two or more rings fused together, has only carbon atoms as cyclic atoms, and is not aromatic in its overall molecular structure. An example of a monovalent nonaromatic fused polycyclic group is the fluorene group. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.

[0329] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 2-60 carbon atoms) that has two or more rings fused together, has at least one heteroatom selected from N, O, P, Si, and S as a cyclic atom in addition to the carbon atoms, and is not aromatic in its overall molecular structure. An example of a monovalent nonaromatic fused heterocyclic group is the carbazoyl group. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused heterocyclic group.

[0330] As used in this article, the term "C5-C" 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group with only 5-30 carbon atoms as cyclic atoms. (C5-C) 30 The carbocyclic group can be a monocyclic or polycyclic group. "(Unsubstituted or substituted with at least one R)" 1a (Replacement) C5-C 30 Examples of "carbocyclic groups" are (each unsubstituted or substituted by at least one R) 1a Substituted) adamantyl group, norbornene group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptane (norbornene) group, bicyclo[2.2.2]octyl group, cyclopentyl group, cyclohexyl group, cyclohexene group, phenyl group, naphthyl group, anthracene group, phenanthrene group, benzo[9,10]phenanthrene group, pyrene group, Groups, 1,2,3,4-tetrahydronaphthalene group, cyclopentadienyl group, and fluorene group.

[0331] As used in this article, the term "C1-C" 30 A "heterocyclic group" refers to a saturated or unsaturated cyclic group that has at least one heteroatom selected from N, O, P, Si, Se, Ge, B, and S as a cyclic atom in addition to 1-30 carbon atoms. (C1-C) 30 Heterocyclic groups can be monocyclic or polycyclic. "(Unsubstituted or substituted with at least one R)" 1a (Replacement) C1-C 30 Examples of "heterocyclic groups" are (each unsubstituted or substituted by at least one R) 1aSubstituted thiophene group, furan group, pyrrole group, thiophene group, borocyclopentadien group, phosphacyclopentadien group, selenophene group, germanium heterocyclopentadien group, benzothiophene group, benzofuran group, indole group, benzothiophene group, benzoboron heterocyclopentadien group, benzophosphacyclopentadien group, benzoselenophene group, benzogermanium heterocyclopentadien group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzothiophene group, dibenzoboron heterocyclopentadien group, dibenzophosphacyclopentadien group, dibenzoselenophene group, dibenzogermanium heterocyclopentadien group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, nitrogen The following groups are listed: benzothiophene group, azibabenzoborane group, azibabenzophosphacyclopentadiene group, azibabenzoselenophene group, azibabenzogeranecyclopentadiene group, azibadibenzothiophene group, azibadibenzofuran group, azibacarbazole group, azibafluorene group, azibadibenzothiophene group, azibadibenzoboranecyclopentadiene group, azibadibenzophosphacyclopentadiene group, azibadibenzoselenophene group, azibadibenzogeranecyclopentadiene group, azibadibenzothiophene 5-oxide group, aziba-9H-fluorene-9-one group, azibadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazolinine group, phenanthrene-rhein group, pyrazole group, imidazole group, triazole group. azole group, iso- azole group, thiazole group, isothiazole group, Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo[] azole group, benzothiazole group, benzo[] The diazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, and 5,6,7,8-tetrahydroquinoline group.

[0332] The term "fluorinated C1-C" 60 Alkyl (or fluorinated C1-C) 20 Alkyl groups, etc.; Fluorinated C3-C 10 "Cycloalkyl", "Fluorinated C1-C" 10 "Heterocyclic alkyl" and "fluorinated phenyl" respectively represent C1-C1 alkyl groups substituted with at least one fluorine group (-F). 60 Alkyl (or C1-C) 20 Alkyl groups, etc., C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl groups and phenyl groups. For example, "fluorinated C1 alkyl (i.e., fluorinated methyl)" may include -CF3, -CF2H, and -CFH2. "Fluorinated C1-C60 Alkyl (or fluorinated C1-C) 20 Alkyl groups, etc.; Fluorinated C3-C 10 "Cycloalkyl", "Fluorinated C1-C" 10 "Heterocyclic alkyl" or "fluorinated phenyl" can be: i) fully fluorinated C1-C 60 Alkyl (or fully fluorinated C1-C) 20 Alkyl groups, etc., and fully fluorinated C3-C 10 cycloalkyl, fully fluorinated C1-C 10 Heterocyclic alkyl groups, or fully fluorinated phenyl groups, wherein all hydrogens in each group are replaced by fluorine groups, or ii) partially fluorinated C1-C 60 Alkyl (or partially fluorinated C1-C) 20 Alkyl groups, etc., and partially fluorinated C3-C 10 cycloalkyl, partially fluorinated C1-C 10 Heterocyclic alkyl groups, or partially fluorinated phenyl groups, wherein some, but not all, of the hydrogen atoms in each group are replaced by fluorine groups.

[0333] The term "deuterated C1-C" 60 Alkyl (or deuterated C1-C) 20 Alkyl groups, etc., and deuterated C3-C 10 "Cycloalkyl", "Deuterated C1-C" 10 "Heterocyclic alkyl" and "deuterated phenyl" respectively represent C1-C alkyl groups substituted with at least one deuterium. 60 Alkyl (or C1-C) 20 Alkyl groups, etc., C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl groups and phenyl groups. For example, "deuterated C1 alkyl (i.e., deuterated methyl)" may include -CD3, -CD2H, and -CDH2, and "deuterated C3-C 10 Examples of "cycloalkyl" are, for example, formula 10-501, etc. "Deuterated C1-C..." 60 Alkyl (or deuterated C1-C) 20 Alkyl groups, etc., and deuterated C3-C 10 "Cycloalkyl", "Deuterated C1-C" 10 "Heterocyclic alkyl" or "deuterated phenyl" can be: i) fully deuterated C1-C 60 Alkyl (or fully deuterated C1-C) 20 Alkyl groups, etc., and fully deuterated C3-C 10 Cycloalkyl, fully deuterated C1-C 10 Heterocyclic alkyl groups, or fully deuterated phenyl groups, wherein all hydrogens in each group are replaced by deuterium, or ii) partially deuterated C1-C 60Alkyl (or partially deuterated C1-C) 20 Alkyl groups, etc.), and partially deuterated C3-C 10 cycloalkyl, partially deuterated C1-C 10 Heterocyclic alkyl groups, or partially deuterated phenyl groups, wherein some, but not all, of the hydrogen atoms in each group are replaced by deuterium.

[0334] As used in this article, the term "(C1-C" is similar to the term "(C1-C)" 20 "alkyl)'X' group" refers to a group consisting of at least one C1-C1 group. 20 Alkyl-substituted 'X' groups. For example, as used herein, the term "(C1-C1)" 20 Alkyl)C3-C 10 "Cycloalkyl" refers to a compound formed by at least one C1-C2 group. 20 Alkyl-substituted C3-C 10 Cycloalkyl, and as used herein by the term "(C1-C1)". 20 "alkyl)phenyl" refers to a compound formed by at least one C1-C2 bond. 20 Alkyl-substituted phenyl groups. An example of (C1 alkyl)phenyl is tolyl.

[0335] As used herein, the terms "azaindole group, azabenzoboranecyclopentadienyl group, azabenzophosphacyclopentadienyl group, azaindene group, azabenzothiophene group, azabenzogeraniumcyclopentadienyl group, azabenzothiophene group, azabenzofuran group, azacarbazole group, azadibenzoboranecyclopentadienyl group, azadibenzophosphacyclopentadienyl group, azafluorene group, azadibenzothiophene group, azadibenzogeraniumcyclopentadienyl group, azadibenzothiophene group, azadibenzoselenene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, or azadibenzothiophene 5,5-dioxane group" are used in this document. "Chemical group" refers to a heterocyclic group having the same skeleton as "indole group, benzoborane heterocyclopentadienyl group, benzophoshexacyclopentadienyl group, indene group, benzothiophene group, benzogermanium heterocyclopentadienyl group, benzothiophene group, benzoselenene group, benzofuran group, carbazole group, dibenzoborane heterocyclopentadienyl group, dibenzophoshexacyclopentadienyl group, fluorene group, dibenzothiophene group, dibenzogermanium heterocyclopentadienyl group, dibenzothiophene group, dibenzoselenene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, or dibenzothiophene 5,5-dioxide group".

[0336] Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C7-C 60 Aryl groups, substituted C1-C 60 heteroaryl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 heteroaryl thiols, substituted C2-C 60 Heteroalkyl, substituted C2-C 60 At least one substituent of the alkyl heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group can each independently be:

[0337] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;

[0338] C1-C replaced by one or more of the following 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -N(Q 11 (Q) 12 ), -Si(Q 13 (Q) 14 (Q) 15 -Ge(Q) 13 (Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 ), or -P(Q 18 (Q) 19 );

[0339] Each of the following C3-Cs that has not been replaced or has been replaced by one or more of the following: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -N(Q 21 (Q) 22 ), -Si(Q 23 (Q) 24 (Q) 25 -Ge(Q) 23 (Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 ), or -P(Q 28 (Q) 29 );

[0340] -N(Q 31 (Q) 32 ), -Si(Q 33 (Q) 34 (Q) 35 -Ge(Q) 33 (Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q) 38 (Q) 39 ), or -P(Q 38 (Q) 39 );or

[0341] Any combination thereof.

[0342] In this specification, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each of these can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidine; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphate group or its salt; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 C1-C substituted with aryl or any combination thereof 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy group; C1-C 60 Alkylthio group; C3-C 10 cycloalkyl; C1-C 10 Heterocyclic alkyl; C3-C 10 Cycloalkenyl; C1-C 10 Heterocyclic alkenyl groups; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 C6-C substituted with aryl or any combination thereof 60 Aryl; C6-C 60 Aryloxy group; C6-C 60 Arylthio; C7-C 60 Aryl group; C1-C 60 heteroaryl; C1-C 60 Heteroaryloxy group; C1-C 60 heteroaryl thio; C2-C 60 Heteroalkyl; C2-C 60 Alkyl heteroaryl; monovalent non-aromatic fused polycyclic group; or monovalent non-aromatic fused heterocyclic group.

[0343] For example, Q1-Q9 and Q described in this article 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each can be independently:

[0344] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0345] Each of the following is either unsubstituted or substituted with: 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: deuterium, C1-C 10 Alkyl or phenyl; or

[0346] Any combination thereof.

[0347] The compounds and organic light-emitting devices according to the embodiments will be described in detail below with reference to the synthesis examples and examples. However, this disclosure is not limited thereto. The phrase "using B instead of A" used in describing the synthesis examples means that, in molar equivalents, the amount of A used is the same as the amount of B used.

[0348] Example

[0349] Synthesis Example 1: (Synthesis of Compound 1)

[0350]

[0351] (1) Synthesis of compound 1A

[0352] 2-Phenylacetylene (5.2 g, 33.1 mmol) and iridium chloride trihydrate (IrCl3(H2O)) were prepared. n Compound 1A (n=3) (5.2 g, 14.7 mmol) was mixed with 120 mL of ethoxyethanol and 40 mL of deionized water (DI water), and the resulting mixture was stirred under reflux for 24 hours. The reaction temperature was then lowered to room temperature. The resulting solid was separated by filtration, thoroughly washed with water / methanol / hexane in the order stated herein, and dried in a vacuum oven to obtain 8.2 g (92% yield) of compound 1A. Compound 1A was used in the next reaction without any further purification.

[0353] (2) Synthesis of compound 1B

[0354] Compound 1A (1.6 g, 1.5 mmol) was mixed with 45 mL of dichloromethane (MC), and a mixture of silver trifluoromethanesulfonate (AgOTf) (0.8 g, 3.1 mmol) and 15 mL of methanol (MeOH) was added. The resulting mixture was then stirred for 18 hours while blocking light with aluminum foil, and then filtered through diatomaceous earth to remove the resulting solid. The filtrate was evaporated under reduced pressure to obtain a solid (compound 1B), which was used in the next reaction without any further purification.

[0355] (3) Synthesis of compound 2A

[0356] Under a nitrogen atmosphere, 9-(4-bromophenyl)-9H-carbazole (1.5 g, 4.66 mmol), bis(pinacolyl)diboron (1.54 g, 6.05 mmol), [1,1-bis(diphenylphosphino)-ferrocene]palladium(II) dichloride (PdCl2(DPPF)) (0.34 g, 0.47 mmol), and potassium acetate (KOAc) (1.37 g, 13.97 mmol) were added to a 1,4-dioxane / toluene solvent (1:1 volume ratio) and stirred. The mixture was stirred in an oil bath under reflux at 120 °C for 17 hours. After the reaction was complete, the reaction temperature was lowered to room temperature, the solvent was removed, and the obtained solid was subjected to column chromatography (eluent: dichloromethane (MC) and hexane) to obtain 1.6 g (93% yield) of 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)phenyl)-9H-carbazole. The obtained material was confirmed by high-resolution mass spectrometry (HRMS) and high-performance liquid chromatography (HPLC).

[0357] High-resolution mass spectrometry (MRMS (MALDI)): for C 24 H 24 Calculated value of BNO2: m / z: 369.19, measured value: 370.23

[0358] (4) Synthesis of compound 2B

[0359] In a nitrogen atmosphere, 2-bromo-4-isobutyl-5-(trimethylsilyl)pyridine (1.5 g, 5.24 mmol) was dissolved in 100 mL of tetrahydrofuran, and 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)phenyl)-9H-carbazole (compound 2A) (2.1 g, 5.76 mmol) was added. Potassium carbonate (K₂CO₃) (1.7 g, 15.72 mmol) was dissolved in 25 mL of DI water and added to the reaction mixture. Then, palladium catalyst (Pd(PPh₃)₄) (0.6 g, 0.52 mmol) was added. The resulting reaction mixture was then stirred under reflux at 80 °C. Following the extraction process, the obtained solid was subjected to column chromatography (eluent: MC and hexane) to obtain 1.91 g (92% yield) of 9-(4-(4-isobutyl-5-(trimethylsilyl)pyridin-2-yl)phenyl)-9H-carbazole. The obtained material was confirmed by HRMS and HPLC analysis.

[0360] HRMS (MALDI): For C 30 H 32Calculated value of N₂Si: m / z: 448.23, measured value: 449.69

[0361] (5) Synthesis of Compound 1

[0362] Compound 1B (1.5 g, 2.10 mmol) and 9-(4-(4-isobutyl-5-(trimethylsilyl)pyridin-2-yl)phenyl)-9H-carbazole (compound 2B) (1.0 g, 2.31 mmol) were mixed with 40 mL of 2-ethoxyethanol, and the resulting mixture was stirred under reflux at 110 °C for 24 h. The reaction temperature was then lowered. The resulting mixture was evaporated under reduced pressure, and the obtained solid was subjected to column chromatography (eluent: dichloromethane and hexane) to obtain 0.93 g (47% yield) of compound 1. The obtained material was confirmed by HRMS and HPLC analysis.

[0363] HRMS (MALDI): For C 52 H 47 Calculated value of IrN4Si: m / z: 948.32; Measured value: 949.28

[0364] Synthesis Example 2: (Synthesis of Compound 3)

[0365]

[0366] (1) Synthesis of compound 3A

[0367] In a nitrogen atmosphere, (1-chlorodibenzo[b,d]furan-4-yl)boronic acid (3.0 g, 10.5 mmol) and 2-bromo-4-isobutyl-5-(trimethylsilyl)pyridine (3.1 g, 12.6 mmol) were dissolved in 200 mL of tetrahydrofuran. K₂CO₃ (3.3 g, 31.4 mmol) was dissolved in 50 mL of DI water and added to the reaction mixture. Then, palladium catalyst (Pd(PPh₃)₄) (1.2 g, 1.05 mmol) was added. The resulting reaction mixture was then stirred under reflux at 100 °C. After extraction, the obtained solid was subjected to column chromatography (eluent: MC and hexane) to obtain 3.9 g (95% yield) of 2-(1-chlorodibenzo[b,d]furan-4-yl)-4-isobutyl-5-(trimethylsilyl)pyridine. The obtained materials were confirmed by HRMS and HPLC analysis.

[0368] HRMS (MALDI): For C 24 H 26 Calculated value of ClNOSi: m / z: 407.15, measured value: 409.20

[0369] (2) Synthesis of compound 3B

[0370] Compound 3A (6.1 g, 14.9 mmol), 9H-carbazole (1.0 g, 6.0 mmol), sodium tert-butoxide (NaOt-Bu) (1.2 g, 11.9 mmol), and bis(tri-tert-butylphosphine)palladium(O) (610 mg, 1.2 mmol) were added to 50 mL of toluene under a nitrogen atmosphere and stirred under reflux. After the reaction was complete, the reaction temperature was lowered to room temperature, and the extraction process was performed using dichloromethane and water. After treatment with anhydrous magnesium sulfate, the resulting product was filtered and concentrated under reduced pressure. Following the extraction process, the obtained solid was subjected to column chromatography (eluent: dichloromethane and hexane) to obtain 2.7 g (84% yield) of 9-(4-(4-isobutyl-5-(trimethylsilyl)pyridin-2-yl)dibenzo[b,d]furan-1-yl)-9H-carbazole. The obtained material was confirmed by HRMS and HPLC analysis.

[0371] HRMS (MALDI): For C 36 H 34 Calculated N2OSi value: m / z: 538.24, measured value: 539.78

[0372] (3) Synthesis of compound 3

[0373] Compound 1B (1.5 g, 2.1 mmol) and compound 3B (1.3 g, 2.3 mmol) were combined with 20 mL of 2-ethoxyethanol and 20 mL of N,N-dimethylformamide, and the resulting mixture was stirred under reflux at 110 °C for 24 h. The reaction temperature was then lowered. Extraction was performed using dichloromethane and water. After treatment with anhydrous magnesium sulfate, the resulting product was filtered and concentrated under reduced pressure. Following extraction, the obtained solid was subjected to column chromatography (eluent: dichloromethane and hexane) to obtain 0.8 g (38% yield) of compound 3. The obtained material was confirmed by HRMS and HPLC analysis.

[0374] HRMS (MALDI): For C 58 H 49 Calculated value of IrN4OSi: m / z: 1038.33, measured value: 1039.40

[0375] Synthesis Example 3: (Synthesis of Compound 4)

[0376]

[0377] Compound 4 was obtained in the same manner as in the synthesis of compound 3, except that (1-chlorodibenzo[b,d]thiophene-4-yl)boronic acid was used instead of (1-chlorodibenzo[b,d]furan-4-yl)boronic acid as a starting material to synthesize compound 4A. The obtained material was confirmed by HRMS and HPLC analysis.

[0378] HRMS (MALDI): For C 58 H 49 Calculated value of IrN4SSi: m / z: 1054.31, measured value: 1055.48

[0379] Synthesis Example 4: (Synthesis of Compound 5)

[0380]

[0381] Compound 5 was obtained in the same manner as in the synthesis of compound 3, except that 2-bromo-4-isopropylpyridine was used instead of 2-bromo-4-isobutyl-5-(trimethylsilyl)pyridine as a starting material to synthesize compound 5A. The obtained material was confirmed by HRMS and HPLC analysis.

[0382] HRMS (MALDI): For C 54 H 39 Calculated value of IrN4O: m / z: 952.28, measured value: 953.15

[0383] Example 1

[0384] ITO (as anode) patterned glass substrates were cut to dimensions of 50mm × 50mm × 0.5mm, ultrasonically treated with isopropanol and DI water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The resulting glass substrates were then loaded onto a vacuum deposition apparatus.

[0385] Compounds HT3 and F12 (p-doper) were vacuum co-deposited on the anode at a weight ratio of 98:2 to form a structure with... A hole injection layer of a certain thickness is formed, and compound HT3 is vacuum deposited on the hole injection layer to form a layer with [missing information]. A hole transport layer of a certain thickness.

[0386] Subsequently, compound GH3 (the host) and compound 1 (the dopant) were co-deposited on the hole transport layer at a weight ratio of 92:8 to form a structure with... The thickness of the emission layer.

[0387] Next, compound ET3 and LiQ (n-doper) were co-deposited on the emitter layer at a volume ratio of 50:50 to form a structure with... An electron transport layer of a certain thickness is formed by vacuum deposition of LiQ on the electron transport layer to form an electron transport layer with a thickness of [missing information]. An electron-injected layer of a certain thickness is formed, and Al is vacuum-deposited on the electron-injected layer to form a layer with [missing information]. A cathode of a certain thickness is used to complete the fabrication of organic light-emitting devices.

[0388]

[0389] Example 2 and Comparative Examples 1-4

[0390] The organic light-emitting device was manufactured in the same manner as in Example 1, except that, when forming the emission layer, the compounds shown in Table 2 were used instead of compound 1 as dopants.

[0391] Evaluation Example: Characterization of Organic Light-Emitting Devices

[0392] For each organic light-emitting device fabricated in Examples 1 and 2 and Comparative Examples 1-4, the maximum external quantum efficiency (maximum EQE), roll-off ratio (%), and driving voltage (V) were evaluated, and the results are shown in Table 2. A current-voltmeter (KEITHLEY 2400) and a luminance meter (MINOLTA Cs-1000A) were used as evaluation equipment. The roll-off ratio was calculated according to Equation 20:

[0393] Equation 20

[0394] Roll-off ratio = {1 - (emission efficiency (at 3500 nits) / maximum emission efficiency)} × 100%

[0395] Table 2

[0396]

[0397]

[0398] Referring to Table 2, it is confirmed that the organic light-emitting devices of Examples 1 and 2 exhibit improved characteristics, such as lower driving voltage, higher EQE, and lower roll-off ratio. Furthermore, it is also confirmed that, compared to the organic light-emitting devices of Comparative Examples 1-4, the organic light-emitting devices of Examples 1 and 2 simultaneously exhibit a reduced roll-off ratio and excellent EQE and driving voltage characteristics.

[0399] According to one or more embodiments, organometallic compounds possess excellent electrical properties and stability. Therefore, electronic devices including said organometallic compounds, such as organic light-emitting devices, can have low driving voltage, high efficiency, long lifetime, low roll-off ratio, and a relatively narrow field-whole diameter (FWHM) of the emission peak in the EL spectrum. Thus, the use of said organometallic compounds enables the realization of high-quality organic light-emitting devices and electronic devices incorporating them.

[0400] It should be understood that the embodiments described herein are to be considered in the descriptive sense only and are not intended for limiting purposes. The descriptions of features or aspects in the various embodiments should be typically considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims.

Claims

1. Organometallic compounds, represented by formula 21-1 or 21-4: Equation 21-1 Equation 21-4 Equation 1-1 in, In equations 21-1, 21-4, and 1-1, M1 is Ir, n1 is 1 or 2. A3 and A4 are each independently phenyl groups. X1 represents O, S, N(R) 15 ), C(R 15 (R) 16 ), or Si(R) 15 (R) 16 ), R2 is a group represented by formula 1-1. R1 and R3 are independent of each other: Groups represented by Formula 1-1; Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C2-C 20 alkenyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio; Each of the C1-Cs is replaced by one or more of the following: 20 Alkyl, C2-C 20 alkenyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 10 Alkyl, phenyl, (C1-C) 20 Alkyl)phenyl, biphenyl, terphenyl, or naphthyl; or Each of the following phenyl groups that are not substituted or are substituted with one or more of the following: (C1-C) 20 Alkyl)phenyl, biphenyl, terphenyl, or naphthyl: deuterium, -F, -Cl, -Br, -I, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, or C1-C 20 Alkoxy R 22 It can be -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3). R 23 For C1-C 20 Alkyl groups or C1-C molecules substituted with one or more of the following: 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, or C1-C 10 alkyl, R 11 -R 16 R 21 R 24 R 30 R 40 R 51 -R 54 and R 61 -R 64 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C2-C 20 alkenyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio; or Each of the C1-Cs is replaced by one or more of the following: 20 Alkyl, C2-C 20 alkenyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, or C1-C 10 alkyl, b30 and b40 are each independent integers from 1 to 10. and Each represents a binding site with an adjacent atom. Q1-Q3 are each independent of the following: Deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, - OR Each of the following groups, either unsubstituted or substituted with one or more of the following: 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: deuterium, -F, C1-C 10 Alkyl or phenyl.

2. The organometallic compound of claim 1, wherein the deuterated C1-C 20 The alkyl group is -CD3, -CD2H, or -CDH2.

3. The organometallic compound of claim 1, wherein... R1 and R3 are each independently a group represented by Formula 1-1, hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 Alkylphenyl or naphthyl.

4. The organometallic compound of claim 1, wherein... R1 and R3 are both hydrogen.

5. The organometallic compound of claim 1, wherein... R 11 -R 16 R 21 R 23 R 24 R 30 R 40 R 51 -R 54 and R 61 -R 64 Each is independently a group represented by one of formulas 9-1 to 9-39, and R 22 For groups represented by one of formulas 9-40 to 9-43: in, In equations 9-1 to 9-43, Indicates the binding site with adjacent atoms.

6. The organometallic compound of claim 1, wherein... The organometallic compound is one of compounds 1, 3, 4, 21, 27, and 30: 。 7. Organic light-emitting devices, including: First electrode; Second electrode; as well as An organic layer comprising an emission layer is disposed between the first electrode and the second electrode, wherein The organic layer comprises at least one organometallic compound as described in any one of claims 1-6.

8. The organic light-emitting device as claimed in claim 7, wherein... The emitter layer includes at least one organometallic compound.

9. The organic light-emitting device as claimed in claim 8, wherein... The emitter layer further includes a body, and the amount of the body is greater than the amount of the at least one organometallic compound in the emitter layer.

10. The organic light-emitting device of claim 9, wherein... The emission layer emits green light with a maximum emission wavelength of 500 to 600 nanometers.

11. The organic light-emitting device of claim 10, wherein... The first electrode is the anode. The second electrode is a cathode. The organic layer further includes a hole transport region between the first electrode and the emitter layer, and an electron transport region between the emitter 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.

12. An electronic device, including an organic light-emitting device as claimed in any one of claims 7-11.

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