Organic metal compound, organic light-emitting device including the organic metal compound, and electronic device including the organic light-emitting device

Abstract

Disclosed are an organic metal compound, an organic light-emitting device including the organic metal compound, and an electronic device including the organic light-emitting device. The organic metal compound is represented by Formula 1, wherein in Formula 1, M, L 1 , L 2 , n1 and n2 can be referred to as M, L respectively disclosed herein 1 , L 2 , n1 and n2 to understand the formula 1M (L 1 ) n1 (L 2 ) n2。

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of and priority to Korean Patent Application No. 10-2020-0007377 filed in the Korean Intellectual Property Office on January 20, 2020, and all rights arising therefrom, the entire contents of which are incorporated herein by reference. Technical Field

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

[0004] Organic light emitting devices (OLEDs) are self-emitting devices that produce full-color images. In addition, OLEDs have a wide viewing angle and exhibit excellent driving voltage and response speed characteristics.

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

[0006] Provided are a novel organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic device including the organic light-emitting device.

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

[0008] According to an aspect of one embodiment, the organometallic compound may be represented by Formula 1:

[0009] Formula 1

[0010] M(L 1 ) n1 (L 2 ) n2

[0011] Among them, in formula 1,

[0012] M may be a transition metal,

[0013] L 1 may be a ligand represented by Formula 2,

[0014] n1 may be 1, 2, or 3, and when n1 is 2 or greater, at least two L 1 The groups may be identical to or different from each other.

[0015] L 2 It can be a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand,

[0016] n2 may be 0, 1, 2, 3, or 4, and when n2 is 2 or greater, at least two L 2 The groups may be identical to or different from each other.

[0017] L 1 Different from L 2 ,

[0018] Formula 2

[0019]

[0020] Among them, in formula 2,

[0021] A 21 -A 24 can be independently N or C,

[0022] X 1 Can be O or S,

[0023] L 13 may be a single bond, unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0024] Cyclo 1 Can be C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0025] R 1 -R 3 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 Heteroarylthio, substituted or unsubstituted C 2 -C 60 heteroarylalkyl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ),

[0026] b1 can be an integer from 0 to 20.

[0027] b2 can be an integer from 0 to 4.

[0028] From multiple R1 At least two of the groups may be optionally combined (bonded) to each other to form a group which is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0029] From multiple R 2 At least two of the groups may be optionally combined together to form a group which is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0030] R 1 and R 2 One and R 3 may optionally be combined with each other to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0031] R 10a By referring to the R 1 description and understand,

[0032] * and *' each represent a binding site with M in Formula 1, and

[0033] Substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 1 -C 60 Alkylthio, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1-C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 7 -C 60 Arylalkyl, substituted C 1 -C 60 Heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 Heteroarylthio, substituted C 2 -C 60 The substituents of the heteroaralkyl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may each independently be:

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

[0035] Each of C is substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60 heteroarylalkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 ), or a combination thereof;

[0036] C each unsubstituted or substituted 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic 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 )、-P(Q 28 )(Q 29 ), or a combination thereof;

[0037] -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

[0038] Its combination,

[0039] Where Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 can be independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphoric acid group or its salt; unsubstituted or substituted with deuterium, C 1 -C 60 Alkyl, C 6 -C 60 Aryl, or a combination thereof substituted C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; C 3 -C 10 Cycloalkyl; C 1 -C 10 Heterocycloalkyl; C 3 -C 10 Cycloalkenyl; C 1 -C 10 Heterocycloalkenyl; unsubstituted or substituted with deuterium, C 1 -C 60 Alkyl, C 6 -C 60 Aryl, or a combination thereof substituted C 6 -C 60 Aryl; C 6 -C 60 Aryloxy; C 6 -C 60 Arylthio; C 7 -C 60 Aralkyl; C 1 -C 60 Heteroaryl; C1 -C 60 Heteroaryloxy; C 1 -C 60 Heteroarylthio; C 2 -C 60 heteroaralkyl; a monovalent non-aromatic fused polycyclic group; or a monovalent non-aromatic fused heteropolycyclic group.

[0040] According to an aspect of another embodiment, an organic light emitting device may include: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer may include at least one organic metal compound represented by Formula 1.

[0041] The organic metal compound may be included in the emission layer, and the organic metal compound included in the emission layer may serve as a dopant.

[0042] According to an aspect of another embodiment, an electronic device may include the organic light emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0043] By combining Figure 1 The above and other aspects, features and advantages of some embodiments of the present disclosure will become more apparent upon consideration of the following description. Figure 1 is a schematic cross-sectional view of an organic light emitting device according to one or more exemplary embodiments. DETAILED DESCRIPTION

[0044] Embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the present embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the following only describes the embodiments to illustrate aspects by reference to the accompanying drawings. As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. Expressions such as "at least one (kind)" when before or after a list of elements modify the entire list of elements and do not modify the individual elements of the list.

[0045] It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with the other element or intervening elements may exist therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements.

[0046] It will be understood that although the terms first, second, third, etc. can be used to describe various elements, components, regions, layers and / or parts in this article, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish an element, component, region, layer or part from another element, component, region, layer or part. Therefore, without departing from the teaching of the present embodiment, the first element, component, region, layer or part discussed below can be referred to as the second element, component, region, layer or part.

[0047] The terms used herein are only for the purpose of describing specific embodiments and are not intended to be limiting. As used herein, the singular forms "a (a) (indefinite article) (a, an)", "said (the)" are also intended to include plural forms, unless the context clearly states otherwise.

[0048] The term "or" means "and / or". It will be further understood that the terms "comprise" or "include" when used in this specification indicate the presence of stated features, regions, integers, steps, operations, elements and / or components, but do not exclude the presence or addition of one or more additional features, regions, integers, steps, operations, elements, components, and / or combinations thereof.

[0049] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of this disclosure and the relevant art, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0050] Exemplary embodiments are described herein with reference to cross-sectional views as schematic diagrams of one or more idealized embodiments. Thus, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are to be expected. Therefore, the embodiments described herein should not be construed as being limited to the specific shapes of the regions as illustrated herein, but rather include deviations in shape caused by, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. Moreover, the illustrated sharp corners may be rounded. Therefore, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shapes of the regions and are not intended to limit the scope of the claims.

[0051] As used herein, "about" or "approximately" is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±10% or 5% relative to the stated value.

[0052] One aspect of the present disclosure provides an organometallic compound represented by Formula 1:

[0053] Formula 1

[0054] M(L 1 ) n1 (L 2 ) n2

[0055] Wherein, in Formula 1, M may be a transition metal.

[0056] In some embodiments, M can be a first row transition metal, a second row transition metal, or a third row transition metal of the periodic table.

[0057] In some embodiments, M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0058] In one embodiment, M may be Ir, Pt, Os, or Rh.

[0059] In formula 1, L 1 It may be a ligand represented by Formula 2:

[0060] Formula 2

[0061]

[0062] Formula 2 can be understood by reference to its description provided herein.

[0063] In formula 1, n1 represents L 1 The number of groups, and n1 can be 1, 2, or 3. When n1 is 2 or greater, at least two L 1 The groups may be the same as or different from each other. In some embodiments, n1 may be 1 or 2.

[0064] L in Formula 1 2 Can be any suitable organic ligand. In some embodiments, L 2 It can be a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand. 2 By referring to the L provided herein 2description and understand.

[0065] In formula 2, n2 represents L 2 The number of groups, and n2 can be 0, 1, 2, 3, or 4. When n2 is 2 or greater, at least two L 2 The groups may be the same or different from each other. In some embodiments, n2 may be 1 or 2.

[0066] In formula 1, L 1 and L 2 Can be different from each other.

[0067] In one embodiment, in Formula 1, M may be Ir or Os, and the sum of n1 and n2 may be 3 or 4; or M may be Pt, and the sum of n1 and n2 may be 2.

[0068] In one or more embodiments, in Formula 1, M may be Ir, and n1 and n2 may each independently be 1 or 2, and the sum of n1 and n2 may be 3.

[0069] In one or more embodiments, in Formula 1, M may be Ir, n1 may be 3, and n2 may be 0. In this embodiment, the three L 1 The groups may be identical to each other.

[0070] In formula 2, A 21 -A 24 Can be N or C independently. In some embodiments, A 21 -A 24 Can each be C.

[0071] In formula 2, X 1 Can be O or S.

[0072] In formula 2, L 13 may be a single bond, unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.

[0073] In some embodiments, L in Formula 2 13 Can be:

[0074] a single key; or

[0075] Each independently is unsubstituted or substituted with at least one R 10a Substituted benzene group, naphthalene group, anthracene group, phenanthrene group, benzo[9,10]phenanthrene group, pyrene group, group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzothioole group, a dibenzothioole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzothioole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, Azole group, iso azole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo Azole group, benzothiazole group, benzo oxadiazole group, or benzothiadiazole group.

[0076] In one embodiment, L in Formula 2 13 Can be:

[0077] a single key; or

[0078] Each is unsubstituted or replaced by at least one R 10a a substituted benzene group, a naphthyl group, a pyridine group, a dibenzofuran group, a dibenzothiophene group, or a carbazole group.

[0079] In Formula 2, ring CY 1 Can be C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.

[0080] In some embodiments, in Formula 2, ring CY 1 may be i) a first ring, ii) a second ring, iii) a fused ring in which at least two first rings are fused to each other, iv) a fused ring in which at least two second rings are fused to each other, or v) a fused ring in which at least one first ring and at least one second ring are fused to each other,

[0081] The first ring can be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, Azole group, iso Azole group, Oxadiazole group, isocyanate Oxadiazole group, Triazole group, iso a triazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiole group, a diazathiole group, or a triazathiole group, and

[0082] The second ring may be an adamantane group, a norbornane group (a bicyclo[2.2.1]heptane group), a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0083] In one embodiment, in Formula 2, ring CY 1 It can be i) the first ring or ii) the second ring.

[0084] In one or more embodiments, in Formula 2, ring CY 1 It may be a condensed ring in which at least two rings are condensed to each other.

[0085] In some embodiments, in Formula 2, ring CY 1 It may be iii) a ring in which at least two first rings are fused to each other, iv) a fused ring in which at least two second rings are fused to each other, or v) a fused ring in which at least one first ring and at least one second ring are fused to each other.

[0086] In some embodiments, in Formula 2, ring CY 1 It may be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, an adamantane group, a norbornane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, 1,2,3,4-tetrahydronaphthalene group, pyrrole group, boroheterocyclopentadiene group, phosphocyclopentadiene group, cyclopentadiene group, thiorrole group, germanocyclopentadiene group, thiophene group, selenophene group, furan group, indole group, benzoborole group, benzophosphocyclopentadiene group, indene group, benzothiorrole group, benzogermanocyclopentadiene group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, diene group, dibenzophosphole group, fluorene group, dibenzosilole group, dibenzogermanol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzosilole group, azabenzogermanol group heterocyclopentadiene group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermanylcyclopentadiene group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group , azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group, azaborole group, azaphosphole group, azacyclopentadiene group, azathiole group, azagermanol group, azaselenophene group, Azole group, iso azole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo Azole group, benzothiazole group, benzo a oxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

[0087] In one or more embodiments, in Formula 2, ring CY 1 It can be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a quinazoline group, or a phenanthroline group.

[0088] In formula 2, R 1 -R 3 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl (e.g., substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl), substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 Heteroarylthio, substituted or unsubstituted C 2 -C 60 heteroarylalkyl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ). Q 1 -Q 9 can be respectively referred to the Q provided in this article 1 -Q 9 description and understand.

[0089] In some embodiments, in Formula 2, R 1 -R 3 Can be independently:

[0090] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF 5 , C 1 -C 20 Alkyl, C 2 -C 20 Alkenyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio;

[0091] Each of C is substituted by 1 -C 20 Alkyl, C 2 -C 20 Alkenyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C 1 -C20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C 1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C 20 Alkyl) norbornyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl)bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, or a combination thereof;

[0092] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, deuterated C 2 -C 20 Alkyl, C 1 -C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C 1 -C 20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C 1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C 20 Alkyl) norbornyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl)bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazole, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or a combination thereof; or

[0093] -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ),

[0094] Where Q 1 -Q 9 Can be independently:

[0095] Deuterium, -F, -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD3 、-CD 2 CD 3 、-CD 2 CD 2 H.-CD 2 CDH 2 , -CF 3 , -CF 2 H, -CFH 2 、-CH 2 CF 3 、-CH 2 CF 2 H, -CH 2 CFH 2 、-CHFCH 3 , -CHFCF 2 H, -CHFCFH 2 , -CHFCF 3 , -CF 2 CF 3 , -CF 2 CF 2 H, or -CF 2 CFH 2 ;or

[0096] n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl, each unsubstituted or substituted with: deuterium, -F, C 1 -C 10 Alkyl, phenyl, or a combination thereof.

[0097] In some embodiments, in Formula 2, R 1 -R 3 can be independently hydrogen, deuterium, -F, -CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 1 -C 10 Alkoxy, C 1 -C 10an alkylthio group, a group represented by one of formulae 9-1 to 9-39, a group represented by one of formulae 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium, a group represented by one of formulae 9-1 to 9-39 in which at least one hydrogen is replaced by -F, a group represented by one of formulae 9-201 to 9-236, a group represented by one of formulae 9-201 to 9-236 in which at least one hydrogen is replaced by deuterium, a group represented by one of formulae 9-201 to 9-236 in which at least one hydrogen is replaced by -F, a group represented by one of formulae 10-1 to 10-1 a group represented by one of the formulae 10-1 to 10-130 in which at least one hydrogen is replaced by deuterium, a group represented by one of the formulae 10-1 to 10-130 in which at least one hydrogen is replaced by -F, a group represented by one of the formulae 10-201 to 10-358, a group represented by one of the formulae 10-201 to 10-358 in which at least one hydrogen is replaced by deuterium, a group represented by one of the formulae 10-201 to 10-358 in which at least one hydrogen is replaced by -F, -Si(Q 3 )(Q 4 )(Q 5 ), or -Ge(Q 3 )(Q 4 )(Q 5 ), where Q 3 -Q 5 can be respectively referred to the Q provided in this article 3 -Q 5 The description is understood:

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106] In Formulae 9-1 to 9-39, 9-201 to 9-236, 10-1 to 10-130, and 10-201 to 10-358, * represents a binding site with an adjacent atom, "Ph" represents a phenyl group, "TMS" and "SiMe 3 " each represents a trimethylsilyl group, and "TMG" and "GeMe3 ” each represents a trimethylgermyl group.

[0107] The “group represented by one of formulae 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium” and the “group represented by one of formulae 9-201 to 9-236 in which at least one hydrogen is replaced by deuterium” may each be, for example, a group represented by one of formulae 9-501 to 9-514 and 9-601 to 9-636:

[0108]

[0109] The “group represented by one of formulae 9-1 to 9-39 in which at least one hydrogen is replaced by —F” and the “group represented by one of formulae 9-201 to 9-236 in which at least one hydrogen is replaced by —F” may each be, for example, a group represented by one of formulae 9-701 to 710:

[0110]

[0111] The “group represented by one of formulae 10-1 to 10-130 in which at least one hydrogen is replaced by deuterium” and the “group represented by one of formulae 10-201 to 10-358 in which at least one hydrogen is replaced by deuterium” may each be, for example, a group represented by one of formulae 10-501 to 553:

[0112]

[0113]

[0114] The “group represented by one of formulae 10-1 to 10-130 in which at least one hydrogen is replaced by —F” and the “group represented by one of formulae 10-201 to 10-358 in which at least one hydrogen is replaced by —F” may each be, for example, a group represented by one of formulae 10-601 to 617:

[0115]

[0116] In some embodiments, in Formula 2,

[0117] R 2 It can be hydrogen, deuterium, -F, cyano, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 3 -C 10 Cycloalkyl, -Si(Q 3 )(Q 4 )(Q 5 ), or -Ge(Q 3 )(Q 4 )(Q 5 ),

[0118] R 3 Can be substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or

[0119] Its combination.

[0120] In formula 2, b1 represents R 1 The number of groups, and b1 can be an integer from 0 to 20. When b1 is an integer of 2 or more, at least two R 1 The groups may be the same as or different from each other. In some embodiments, b1 may be an integer of 0-10.

[0121] In formula 2, b2 represents R 2 The number of groups, and b2 can be an integer from 0 to 4. When b2 is 2 or greater, at least two R 2 The groups may be the same or different from each other. In some embodiments, b2 may be 0, 1, or 2.

[0122] In one embodiment, in Formula 2, The group represented by may be represented by one of formulae 2(1) to 2(31):

[0123]

[0124]

[0125] Wherein, in Formulas 2(1) to 2(31),

[0126] X 1 By referring to the X provided herein 1 description and understand,

[0127] * represents the binding site with M in Formula 1, and

[0128] *" indicates the binding site with the adjacent carbon atom.

[0129] In one or more embodiments, the The group represented by may be represented by one of formulae 2-1 to 2-57:

[0130]

[0131]

[0132]

[0133]

[0134] Among them, in formulas 2-1 to 2-57,

[0135] X 1 By referring to the X provided herein 1 description and understand,

[0136] R 11 -R 16 Each can be obtained by referring to the R 1 The description of R 11 -R 16 Each of them may not be hydrogen,

[0137] * represents the binding site with M in Formula 1, and

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

[0139] In some embodiments, L in Formula 1 2 The bidentate ligand may be bonded to M in Formula 1 via O, S, Se, N, C, P, Si, As, or a combination thereof.

[0140] In some embodiments, L in Formula 1 2 It may be a bidentate ligand that binds to M in Formula 1 via N and C or a bidentate ligand that binds to M in Formula 1 via two O atoms.

[0141] In one or more embodiments, L in Formula 1 2 It may be a group represented by one of Formulae 3A to 3F:

[0142]

[0143] Wherein, in Formulae 3A to 3F,

[0144] Y 13Can be O, N, N(Z 1 )、P(Z 1 )(Z 2 ), or As(Z 1 )(Z 2 ),

[0145] Y 14 Can be O, N, N(Z 3 )、P(Z 3 )(Z 4 ), or As(Z 3 )(Z 4 ),

[0146] T 11 Can be single bond, double bond, *-C(Z 11 )(Z 12 )-*'、*-C(Z 11 )=C(Z 12 )-*'、*=C(Z 11 )-*'、*-C(Z 11 )=*'、*=C(Z 11 )-C(Z 12 )=C(Z 13 )-*'、*-C(Z 11 )=C(Z 12 )-C(Z 13 )=*'、*-N(Z 11 )-*', or is unsubstituted or replaced by at least one Z 11 Substituted C 5 -C 30 Carbocyclic groups,

[0147] a11 may be an integer from 1 to 10, and when a11 is 2 or greater, at least two T 11 The groups may be identical to or different from each other.

[0148] Y 11 and Y 12 can be independently C or N,

[0149] T 21 Can be single bond, double bond, O, S, C(Z 11 )(Z 12 )、Si(Z 11 )(Z 12 ), or N(Z 11 ),

[0150] Cyclo 11 and CY 12 Can be independently C 5 -C 30 Carbocyclic group or C1 -C 30 Heterocyclic groups,

[0151] A 1 Can be P or As,

[0152] Z 1 -Z 4 and Z 11 -Z 13 Each can be obtained by referring to the R 1 description and understand,

[0153] d1 and d2 can each independently be an integer from 0 to 20, and

[0154] * and *' each represent a binding site to M in Formula 1.

[0155] In some embodiments, in Formula 3D, The group represented by may be represented by one of the formulae CY11-1 to CY11-34, and / or,

[0156] In formulas 3C and 3D, The group represented by may be represented by one of the formulas CY12-1 to CY12-34:

[0157]

[0158]

[0159]

[0160] Wherein, in formulas CY11-1 to CY11-34 and CY12-1 to CY12-34,

[0161] X 31 Can be O, S, N (Z 11 )、C(Z 11 )(Z 12 ), or Si(Z 11 )(Z 12 ),

[0162] X 41 Can be O, S, N (Z 21 )、C(Z 21 )(Z 22 ), or Si(Z 21 )(Z 22 ),

[0163] Y 11 , Y 12 , Z 1 , and Z 2 can be respectively referred to the Y provided herein11 , Y 12 , Z 1 , and Z 2 description and understand,

[0164] Z 11 -Z 18 and Z 21 -Z 28 Each can be obtained by referring to the R 1 description and understand,

[0165] d12 and d22 can each independently be an integer from 0 to 2,

[0166] d13 and d23 can each independently be an integer from 0 to 3,

[0167] d14 and d24 can each independently be an integer of 0-4,

[0168] d15 and d25 can each independently be an integer of 0-5,

[0169] d16 and d26 can each independently be an integer of 0-6,

[0170] In formulae CY11-1 to CY11-34 and CY12-1 to CY12-34, * and *' each represent a binding site with M in formula 1, and *" represents a binding site with an adjacent atom in formula 3C or T in formula 3D. 21 binding site.

[0171] In one or more embodiments, L in Formula 1 2 may be a ligand represented by Formula 3D, and Z in Formula 3D 1 and Z 2 At least one of them may be independently deuterium; -Si(Q 3 )(Q 4 )(Q 5 ); -Ge(Q 3 )(Q 4 )(Q 5 ); or C substituted with at least one deuterium 1 -C 60 alkyl.

[0172] In one or more embodiments, L in Formula 1 2 It may be a ligand represented by one of Formulae 3-1 and 3-101 to 3-112:

[0173]

[0174]

[0175] Among them, in formulas 3-1 and 3-101 to 3-112,

[0176] Y 11 , Y 12 CY 12 , Z 1 -Z 4 , Z 11 -Z 13 , and d2 can be respectively obtained by referring to Y provided herein 11 , Y 12 CY 12 , Z 1 -Z 4 , Z 11 -Z 13 , and d2 are described and understood.

[0177] Z 14 By referring to the Z 1 description and understand,

[0178] e2 can be an integer from 0 to 2.

[0179] e3 can be an integer from 0 to 3.

[0180] e4 can be an integer from 0 to 4, and

[0181] * and *' each represent a binding site to M in Formula 1.

[0182] In some embodiments, in Formula 3-1, Y 11 Can be N, and Y 12 Can be C.

[0183] In some embodiments, Z in Formula 3-1 12 Can be -Si(Q 3 )(Q 4 )(Q 5 ); -Ge(Q 3 )(Q 4 )(Q 5 ); or C substituted with at least one deuterium 1 -C 60 alkyl.

[0184] In some embodiments, Z in Formula 3-1 12 Can be -Si(Q 3 )(Q 4 )(Q 5 ) or -Ge(Q 3 )(Q 4 )(Q 5 ), and Z 13 It may not be hydrogen or methyl.

[0185] In some embodiments, in Formula 3-1, The group represented by may be represented by one of formulae 3-1-1 to 3-1-16, and / or

[0186] In formula 3-1, The group represented by may be represented by one of formulae 3-1(1) to 3-1(16):

[0187]

[0188]

[0189] In Formulas 3-1-1 to 3-1-16 and 3-1(1) to 3-1(16),

[0190] Z 11 -Z 14 can be respectively referred to Z provided herein 11 -Z 14 The description of Z 21 -Z 24 Each can be obtained by referring to Z provided herein 2 The description of Z 11 -Z 14 and Z 21 -Z 24 They may not each be hydrogen,

[0191] * and *' each represent a binding site with M in Formula 1, and

[0192] *" indicates the binding site with the adjacent atoms.

[0193] In formula 2, i) comes from multiple R 1 At least two of the groups may be optionally combined to form a group which is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group, ii) from multiple R 2 At least two of the groups may be optionally combined to form a group which is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 heterocyclic group, and / or iii) R 1 and R 2 One and R3 may be optionally combined to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.

[0194] As used here R 10a By referring to the R 1 description and understand.

[0195] In Formula 2, * and *' each represent a binding site with M in Formula 1.

[0196] In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium.

[0197] In some embodiments, L in Formula 1 1 At least one deuterium may be included.

[0198] In some embodiments, in Formula 1, n2 may not be 0, and L 2 At least one deuterium may be included.

[0199] In some embodiments, the organometallic compound represented by Formula 1 may be one of Compounds 1 to 2023:

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263] The group L in the organometallic compound represented by Formula 1 1 It can be a ligand represented by Formula 2, and n1, that is, L 1 The number of the groups may be 1, 2, or 3. That is, the organic metal compound may necessarily include at least one ligand represented by Formula 2 as a ligand that binds to the metal M.

[0264] In the ligand represented by Formula 2, Ring A may be a condensed ring in which a 6-membered ring is condensed with an imidazole ring, and Ring B may be a condensed ring in which Ring CY 1 With including X 1 The 5-membered ring of the present invention is fused to form a condensed ring (see Formula 2' below). By including Ring A having excellent stability and Ring B having a long conjugation length, the organic metal compound represented by Formula 1 may have improved stability, and the organic metal compound represented by Formula 1 may have a relatively small half width (FWHM) of the emission peak of the photoluminescence (PL) spectrum and / or electroluminescence (EL) spectrum. Therefore, an electronic device including the organic metal compound represented by Formula 1, such as an organic light-emitting device, may have an improved lifespan.

[0265] Formula 2'

[0266]

[0267] The highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, S 1 Energy level, and T 1 The results are shown in Table 1.

[0268] Table 1

[0269] Compound No. HOMO(eV) LUMO(eV) <![CDATA[S 1 (eV)]]> <![CDATA[T 1 (eV)]]> 1 -4.592 -1.178 2.797 2.635 2 -4.559 -1.183 2.777 2.642 3 -4.658 -1.209 2.824 2.643 4 -4.618 -1.191 2.809 2.639 5 -4.529 -1.172 2.758 2.636 822 -4.493 -1.134 2.776 2.480 823 -4.642 -1.242 2.784 2.647

[0270] Referring to the results shown in Table 1, it was found that the organometallic compound represented by Formula 1 had suitable electrical characteristics for use as a dopant in an electronic device such as an organic light-emitting device.

[0271] The method of synthesizing the organometallic compound represented by Formula 1 may be apparent to one of ordinary skill in the art by referring to the synthesis examples provided herein.

[0272] The organometallic compound represented by Formula 1 may be suitable for use in an organic layer of an organic light-emitting device, for example, as a dopant in the organic layer. Therefore, according to another aspect, an organic light-emitting device is provided, which may include a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer may include at least one organometallic compound represented by Formula 1.

[0273] Since the organic light emitting device has the organic layer including the organometallic compound represented by Formula 1, the organic light emitting device may have low driving voltage, high external quantum efficiency, and low roll-off ratio.

[0274] The organic metal compound represented by Formula 1 may be used between an electrode pair of an organic light-emitting device. For example, the organic metal compound represented by Formula 1 may be included in the emission layer. In this embodiment, the organic metal compound may be used as a dopant and the emission layer may further include a host (i.e., the amount of the organic metal compound represented by Formula 1 may be less than the amount of the host). The emission layer may emit red light or green light.

[0275] As used herein, the expression “(the organic layer) includes at least one organometallic compound represented by Formula 1” may be interpreted to mean “(the organic layer) may include one organometallic compound having Formula 1 or two different organometallic compounds having Formula 1”.

[0276] For example, the organic layer may include only compound 1 as an organic metal compound. In this embodiment, compound 1 may be included in the emission layer of the organic light-emitting device. In some embodiments, the organic layer may include compounds 1 and 2 as organic metal compounds. In this embodiment, compounds 1 and 2 may both be included in the same layer (for example, compounds 1 and 2 may both be included in the emission layer).

[0277] The first electrode may be an anode as a hole injection electrode, and the second electrode may be a cathode as an electron injection electrode. In some embodiments, the first electrode may be a cathode as an electron injection electrode, and the second electrode may be an anode as a hole injection electrode.

[0278] For example, in the organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0279] The term "organic layer" as used herein refers to a single and / or multiple layers disposed between a first electrode and a second electrode of an organic light emitting device. The "organic layer" may include not only an organic compound but also an organic metal complex including a metal.

[0280] Figure 1 A schematic cross-sectional view of an organic light emitting device 10 according to an embodiment is described. Figure 1 The structure of an organic light emitting device and a method of manufacturing the same according to one or more embodiments are described. The organic light emitting device 10 may include a first electrode 11, an organic layer 15, and a second electrode 19, which may be sequentially stacked in the order of the statements.

[0281] A substrate may be additionally provided under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in an organic light-emitting device, for example, a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, easy handling, and water repellency.

[0282] The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 onto the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may include a material having a high work function for easy hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), or zinc oxide (ZnO). In some embodiments, the material used to form the first electrode 11 may be a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0283] The first electrode 11 may have a single-layer structure or a multi-layer structure including a plurality of layers. In some embodiments, the first electrode 11 may have a triple-layer structure of ITO / Ag / ITO.

[0284] The organic layer 15 may be on the first electrode 11 .

[0285] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0286] The hole transport region may be disposed between the first electrode 11 and the emission layer.

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

[0288] The hole transport region may include only a hole injection layer or only a hole transport layer. In some embodiments, the hole transport region may include a hole injection layer and a hole transport layer sequentially stacked on the first electrode 11. In some embodiments, the hole transport region may include a hole injection layer, a hole transport layer, and an electron blocking layer sequentially stacked on the first electrode 11.

[0289] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB) deposition.

[0290] When the hole injection layer is formed by vacuum deposition, for example, the vacuum deposition may be performed at a temperature in the range of about 100° C. to about 500° C., at a temperature of about 10 -8 Torr - about 10 -3 Torr range, and at about 0.01 angstrom / second ( / second)-approx. The conditions may vary depending on the compound used as the hole injection material and the desired structure and thermal properties of the hole injection layer.

[0291] When the hole injection layer is formed by spin coating, the spin coating can be performed at a speed in the range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and at a temperature in the range of about 80° C. to 200° C. to facilitate removal of the solvent after the spin coating, although the conditions may vary depending on the compound used as the hole injection material and the desired structure and thermal properties of the hole injection layer.

[0292] The conditions for forming the hole transport layer and the electron blocking layer can be inferred from the conditions for forming the hole injection layer.

[0293] The hole transport region may include at least one of m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, a compound represented by Formula 202, or a combination thereof:

[0294]

[0295]

[0296] Formula 201

[0297]

[0298] Formula 202

[0299]

[0300] In formula 201, Ar 101 and Ar 102 and phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthenylene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyren ... fluorenylene, benzo[9,10]phenanthrenylene, a phenylene group, a tetraphenylene group, a perylene group, a perylene group, or a pentphenylene group: a deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or a combination thereof.

[0301] In Formula 201, xa and xb may each independently be an integer from 0 to 5. In some embodiments, xa and xb may each independently be an integer from 0 to 2. In some embodiments, xa may be 1, and xb may be 0.

[0302] In equations 201 and 202, R 101 -R108 , R 111 -R 119 , and R 121 -R 124 Can be independently:

[0303] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, or hexyl), or C 1 -C 10 Alkoxy (eg, methoxy, ethoxy, propoxy, butoxy, or pentoxy);

[0304] Each of C is substituted by 1 -C 10 Alkyl or C 1 -C 10 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, or a combination thereof; or

[0305] phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl, each of which is unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, or a combination thereof.

[0306] In formula 201, R 109 The phenyl, naphthyl, anthracenyl, or pyridyl groups may be unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salts thereof, sulfonic acid or salts thereof, phosphoric acid or salts thereof, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, naphthyl, anthracenyl, pyridyl, or a combination thereof.

[0307] In some embodiments, the compound represented by Formula 201 can be represented by Formula 201A:

[0308] Formula 201A

[0309]

[0310] Wherein, in Formula 201A, R 101 , R 111 , R 112 , and R 109 can be respectively referred to the R provided in this article 101 , R 111 , R 112 , and R 109 description and understand.

[0311] In some embodiments, the hole transport region may include at least one of compounds HT1 to HT20:

[0312]

[0313]

[0314]

[0315] The thickness of the hole transport region may be about 100 angstroms. -about For example, about -about When the hole transport region includes a hole injection layer, a hole transport layer, or a combination thereof, the thickness of the hole injection layer may be about -about For example, about -about In the range of about 1000 Å, the thickness of the hole transport layer may be about 1000 Å. -about For example, about -about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, excellent hole transport characteristics may be obtained without a significant increase in driving voltage.

[0316] The hole transport region may further include a charge generating material in addition to the aforementioned materials to improve the conductive properties of the hole transport region. The charge generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region.

[0317] The charge generating material may include, for example, a p-dopant. The p-dopant may include one of the following: a quinone derivative, a metal oxide, and a compound containing a cyano group. For example, non-limiting examples of the p-dopant include quinone derivatives such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), or F6-TCNNQ; metal oxides such as tungsten oxide or molybdenum oxide; and compounds containing a cyano group such as compound HT-D1:

[0318]

[0319] The hole transport region may further include a buffer layer.

[0320] The buffer layer may compensate for an optical resonance distance depending on a wavelength of light emitted from the emission layer to improve efficiency of an organic light emitting device.

[0321] When the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may include the host material described herein, the material used to form the hole transport region, or a combination thereof. In some embodiments, when the hole transport region includes an electron blocking layer, the mCP described herein may be used to form the electron blocking layer.

[0322] The emission layer can be formed on the hole transport region by using one or more suitable methods such as vacuum deposition, spin coating, casting, or LB deposition. When the emission layer is formed by vacuum deposition or spin coating, the vacuum deposition and coating conditions for forming the emission layer may be generally (substantially) similar to those for forming the hole injection layer, although the conditions may vary depending on the compound used.

[0323] The emission layer may include a host and a dopant, and the dopant may include an organic metal compound represented by Formula 1.

[0324] The host may include TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, or a combination thereof:

[0325]

[0326] When the organic light emitting device 10 is a full-color organic light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer. In some embodiments, the emission layer may have a structure in which a red emission layer, a green emission layer, and / or a blue emission layer are stacked to emit white light. In some embodiments, the structure of the emission layer may be changed.

[0327] When the emission layer includes the host and the dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on about 100 parts by weight of the host.

[0328] The dopant may be an organometallic compound described herein and represented by Formula 1. In some embodiments, the dopant may be a green phosphorescent dopant.

[0329] The thickness of the emission layer may be about -about and in some embodiments about -about When the thickness of the emission layer is within any of these ranges, improved light emitting characteristics may be obtained without a significant increase in driving voltage.

[0330] An electron transport region may be above the emissive layer.

[0331] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0332] In some embodiments, 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 including two or more different materials.

[0333] The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer can be inferred based on the conditions for forming the hole injection layer.

[0334] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, BCP, BPhen, BAlq, or a combination thereof:

[0335]

[0336] The thickness of the hole blocking layer may be about -about For example, about -about When the thickness of the hole blocking layer is within any of these ranges, excellent hole blocking characteristics may be obtained without a significant increase in driving voltage.

[0337] The electron transport layer may include BCP, BPhen, Alq 3 , BAlq, TAZ, NTAZ, or a combination thereof:

[0338]

[0339] In some embodiments, the electron transport layer may include at least one of compounds ET1 to ET25:

[0340]

[0341]

[0342] The thickness of the electron transport layer may be about -about and in some embodiments about -about When the thickness of the electron transport layer is within any of these ranges, excellent electron transport characteristics may be obtained without a significant increase in driving voltage.

[0343] The electron transport layer may further include a material containing a metal in addition to the materials described above.

[0344] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (LiQ) or compound ET-D2:

[0345]

[0346] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 19 .

[0347] The electron injection layer may include LiF, NaCl, CsF, Li 2 O, BaO, or a combination thereof.

[0348] The thickness of the electron injection layer can be about -about and in some embodiments about -about When the thickness of the electron injection layer is within any of these ranges, excellent electron injection characteristics may be obtained without a significant increase in driving voltage.

[0349] The second electrode 19 may be 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 material having a relatively low work function, such as a metal, an alloy, a conductive compound, or a mixture thereof. Examples of materials used to form the second electrode 19 may include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). In some embodiments, ITO or IZO may be used to form a transmissive second electrode 19 to manufacture a top-emitting light-emitting device. In some embodiments, the material used to form the second electrode 19 may be changed.

[0350] In the previous article, reference has been made to Figure 1 The organic light emitting device 10 is described, but the embodiment is not limited thereto.

[0351] According to another aspect of an embodiment, an electronic device including the organic light emitting device may be provided. The electronic device may be used for various purposes such as a display, a lighting device, and a mobile phone.

[0352] According to aspects of yet another embodiment, the diagnostic composition may include at least one organometallic compound represented by Formula 1.

[0353] Since the organometallic compound represented by Formula 1 provides high luminescence efficiency, the diagnostic efficiency of the diagnostic composition including the organometallic compound represented by Formula 1 may be excellent.

[0354] The diagnostic composition can be used in various ways, for example, in a diagnostic kit, a diagnostic reagent, a biosensor, or a biomarker.

[0355] As used herein, the term "C 1 -C 60 "Alkyl" refers to a straight chain or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. As used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 Alkyl is a divalent group of the same structure.

[0356] As used in this article, C 1 -C 60 Alkyl, C 1 -C 20 Alkyl, and / or C 1 -C 10 Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, , secondary decyl or tert-decyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, or a combination thereof. In some embodiments, Formula 9-33 may be a branched C 6 Formula 9-33 may be a tert-butyl group substituted with two methyl groups.

[0357] As used herein, the term "C 1 -C 60 "Alkoxy" refers to a 101 (A 101 C1 -C 60 A monovalent group represented by an alkyl group.

[0358] As used in this article, C 1 -C 60 Alkoxy, C 1 -C 20 Alkoxy, or C 1 -C 10 Examples of the alkoxy group may include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group.

[0359] As used herein, the term "C 2 -C 60 "Alkenyl" refers to a group consisting of 2 -C 60 A group formed by placing at least one carbon-carbon double bond in the middle or at the end of an alkyl group. Examples thereof include ethenyl, propenyl, and butenyl. As used herein, the term "C 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0360] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a 2 -C 60 A group formed by placing at least one carbon-carbon triple bond in the middle or at the end of an alkyl group. Examples thereof include ethynyl and propynyl. As used herein, the term “C 2 -C 60 "Alkyne" refers to a group having a C 2 -C 60 Alkynyl is a divalent group of the same structure.

[0361] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent cyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms. As used herein, the term "C 3 -C 10 "Cycloalkylene" refers to a cycloalkylene having a 3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0362] As used in this article, C 3 -C 10Examples of cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, or bicyclo[2.2.2]octyl.

[0363] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent monocyclic group including at least one heteroatom as a ring atom and 1 to 10 carbon atoms, wherein the heteroatom may be N, O, P, Si, Se, Ge, B, or S. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0364] As used in this article, C 1 -C 10 Examples of the heterocycloalkyl group may include a silacyclopentyl group, a silacyclohexyl group, a tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, or a tetrahydrothienyl group.

[0365] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, wherein the overall molecular structure is non-aromatic. Examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0366] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl" refers to a monovalent monocyclic group including at least one heteroatom as a ring atom, 1 to 10 carbon atoms, and at least one double bond in its ring, wherein the heteroatom is N, O, P, Si, Se, Ge, B, or S. 1 -C 10 Examples of heterocycloalkenyl groups include 2,3-dihydrofuranyl and 2,3-dihydrothienyl. 1 -C 10 "Heterocycloalkylene" refers to a 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0367] As used herein, the term "C6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. As used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include a plurality of rings, the plurality of rings may be fused to each other.

[0368] As used herein, the term "C 7 -C 60 "Alkaryl" refers to a 1 -C 60 Alkyl substituted C 6 -C 60 Aryl. As used herein, the term "C 7 -C 60 "Arylalkyl" refers to a C 6 -C 60 Aryl substituted C 1 -C 60 alkyl.

[0369] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom as a ring atom and 1 to 60 carbon atoms, wherein the heteroatom is N, O, P, Si, Se, Ge, B, or S. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom as a ring atom and 1 to 60 carbon atoms, wherein the heteroatom is N, O, P, Si, Se, Ge, B, or S. 1 -C 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, and isoquinolyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include a plurality of rings, the plurality of rings may be fused to each other.

[0370] As used herein, the term "C 2 -C60 "Alkylheteroaryl" refers to a 1 -C 60 Alkyl substituted C 1 -C 60 Heteroaryl.

[0371] As used herein, the term "C 6 -C 60 Aryloxy" is represented by -OA 102 (A 102 C 6 -C 60 As used herein, the term "C 6 -C 60 Arylthio" is represented by -SA 103 (A 103 C 6 -C 60 As used herein, the term "C 1 -C 60 "Alkylthio" is represented by -SA 104 (A 104 C 1 -C 60 Alkyl) represents.

[0372] As used herein, the term "C 1 -C 60 "Heteroaryloxy" refers to -OA 106 (A 106 C 1 -C 60 Heteroaryl), as used herein, 1 -C 60 "Heteroarylthio" means -SA 107 (A 107 C 1 -C 60 heteroaryl), and as used herein, the term "C 2 -C 60 "Heteroaralkyl" refers to -A 108 A 109 (A 109 C 1 -C 59 heteroaryl, and A 108 C 1 -C 59 alkylene).

[0373] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group having two or more fused rings and having only carbon atoms (e.g., the number of carbon atoms may be in the range of 8-60) as ring-forming atoms, wherein the overall molecular structure is non-aromatic. Examples of monovalent non-aromatic fused polycyclic groups include fluorenyl. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having a structure substantially the same as that of a monovalent non-aromatic fused polycyclic group.

[0374] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group having two or more fused rings and having at least one heteroatom and carbon atom (e.g., the number of carbon atoms may be in the range of 1-60) as ring-forming atoms, the heteroatom being N, O, P, Si, Se, Ge, B, or S, wherein the overall molecular structure is non-aromatic. Examples of monovalent non-aromatic fused heteropolycyclic groups include carbazolyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having a structure substantially the same as a monovalent non-aromatic fused heteropolycyclic group.

[0375] As used herein, the term "C 5 -C 30 The term "carbocyclic group" refers to a saturated or unsaturated cyclic group containing only 5 to 30 carbon atoms as ring atoms. 5 -C 30 The carbocyclic group may be a monocyclic group or a polycyclic group. 10a Replaced by)C 5 -C 30 Examples of the "carbocyclic group" may include (each unsubstituted or substituted by at least one R 10a substituted) adamantane group, norbornene group, norbornane group (bicyclo[2.2.1]heptane group), bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.2]octane group, cyclopentane group, cyclohexane group, cyclohexene group, phenyl group, naphthalene group, anthracene group, phenanthrene group, benzo[9,10]phenanthrene group, pyrene group, group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, a silole group, or a fluorene group.

[0376] As used herein, the term "C 1 -C 30 The term "heterocyclic group" refers to a saturated or unsaturated cyclic group comprising 1 to 30 carbon atoms and at least one heteroatom as a ring atom, wherein the heteroatom is N, O, P, Si, Se, Ge, B, or S. 1 -C 30The heterocyclic group may be a monocyclic group or a polycyclic group. 10a Replaced by)C 1 -C 30 Examples of the "heterocyclic group" may include (each unsubstituted or substituted by at least one R 10a a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzothiorrole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermanol group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzothiorrole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermanol group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group , an azabenzothiorrole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermanol group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzothiorrole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermanol group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, Azole group, iso azole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo Azole group, benzothiazole group, benzo a oxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

[0377] As used herein, "deuterated C 1 -C 60 Alkyl (or deuterated C 1 -C 20 Alkyl, deuterated C 2 -C 20 "alkyl, etc.)" refers to a C 1 -C 60Alkyl (or C 1 -C 20 Alkyl, C substituted with at least one deuterium 2 -C 20 alkyl, etc.) "deuterated C 1 Examples of "alkyl (e.g., deuterated methyl)" include -CD 3 、-CD 2 H, and -CDH 2 .

[0378] As used herein, "deuterated C 3 -C 10 "Cycloalkyl" refers to a C 3 -C 10 Cycloalkyl. "Deuterated C 3 -C 10 Examples of "cycloalkyl" include formula 10-501.

[0379] As used herein, "fluorinated" 1 -C 60 Alkyl (or fluorinated C 1 -C 20 Alkyl, etc.)", "Fluorinated C 3 -C 10 Cycloalkyl", "fluoro-C 1 -C 10 "Heterocycloalkyl" and "fluorophenyl" may be C 1 -C 60 Alkyl (or C 1 -C 20 Alkyl, etc.), C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, and phenyl. "Fluoro C 1 Examples of "alkyl (i.e., fluoromethyl)" may include -CF 3 , -CF 2 H, and -CFH 2 . "Fluoro-C 1 -C 60 Alkyl (or fluorinated C 1 -C 20 Alkyl, etc.)", "Fluorinated C 3 -C 10 Cycloalkyl" or "fluoro-C 1 -C 10 The "heterocycloalkyl" may be: i) a fully fluorinated C 1 -C 60 Alkyl (or fully fluorinated C1 -C 20 alkyl, etc.), fully fluorinated C 3 -C 10 Cycloalkyl, or fully fluorinated C 1 -C 10 or ii) a partially fluorinated C 1 -C 60 Alkyl (or partially fluorinated C 1 -C 20 alkyl, etc.), partially fluorinated C 3 -C 10 Cycloalkyl or partially fluorinated C 1 -C 10 Heterocycloalkyl.

[0380] “(C 1 -C 20 Alkyl)'X' group" refers to a 1 -C 20 Alkyl substituted 'X' group. For example, as used herein, "(C 1 -C 20 Alkyl)C 3 -C 10 "Cycloalkyl" refers to a cycloalkyl group consisting of at least one C 1 -C 20 Alkyl substituted C 3 -C 10 Cycloalkyl, and as used herein, "(C 1 -C 20 "Alkyl)phenyl" refers to a 1 -C 20 Alkyl substituted phenyl. (C 1 -C 20 Examples of the alkyl)phenyl group may include tolyl.

[0381] As used herein, the “azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzosilole group, azabenzogermanol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermanol group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, and azadibenzothiophene 5,5-dione group” may be used herein. The “oxide group” each refers to a heterocyclic ring in which at least one ring-forming carbon atom is replaced by a nitrogen atom and has the same skeleton as the “indole group, benzoborole group, benzophosphole group, indene group, benzosilole group, benzogermanol group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzosilole group, dibenzogermanol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, and dibenzothiophene 5,5-dioxide group”, respectively.

[0382] Substituted C 5 -C 30 Carbocyclic groups, substituted C 2 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 1 -C 60 Alkylthio, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Alkaryl, substituted C 6 -C 60Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 At least one substituent of the alkylheteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may each independently be:

[0383] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy;

[0384] Each of C is substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C60 Alkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 2 -C 60 Heteroarylalkyl, C 2 -C 60 alkylheteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 ), or a combination thereof;

[0385] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 an alkylheteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group;

[0386] Each of C is substituted by 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 alkylheteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 ), or a combination thereof;

[0387] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 );or

[0388] Its combination.

[0389] In the formulae of the present disclosure, Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphoric acid group or its salt; unsubstituted or substituted with deuterium, C 1 -C 60 Alkyl, C 6 -C 60 Aryl, or a combination thereof substituted C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; C 3 -C 10 Cycloalkyl; C 1 -C 10 Heterocycloalkyl; C 3 -C 10 Cycloalkenyl; C 1 -C 10 Heterocycloalkenyl; unsubstituted or substituted with deuterium, C 1 -C 60Alkyl, C 6 -C 60 Aryl, or a combination thereof substituted C 6 -C 60 Aryl; C 6 -C 60 Aryloxy; C 6 -C 60 Arylthio; C 7 -C 60 Aralkyl, C 1 -C 60 Heteroaryl; C 1 -C 60 Heteroaryloxy; C 1 -C 60 Heteroarylthio; C 2 -C 60 heteroaralkyl; a monovalent non-aromatic fused polycyclic group; or a monovalent non-aromatic fused heteropolycyclic group.

[0390] Hereinafter, exemplary compounds and exemplary organic light-emitting devices according to one or more embodiments will be described in detail with reference to Synthesis Examples and Examples. However, the present disclosure is not limited thereto. The phrase "using compound B instead of compound A" used in describing a Synthesis Example means that, based on molar equivalents, the amount of compound B used is the same as the amount of compound A used, wherein compounds A and B are not the same.

[0391] Example

[0392] Synthesis Example 1 (Synthesis of Compound 1)

[0393] The synthesis of compound 1 is shown in Scheme 1.

[0394] Solution 1

[0395]

[0396] Synthesis of Compound 1-2

[0397] 10 grams (g) (35.33 millimoles, mmol) of compound 1-1 and 6.17g (17.50mmol) of iridium chloride were mixed with 90 milliliters (mL) of ethoxyethanol and 30mL of distilled water. Then, the mixture was stirred under reflux for 24 hours, and then the temperature was lowered to room temperature. A solid was formed therefrom and the solid was separated by filtration. The solid was fully washed with water, methanol, and hexane in the order stated and dried in a vacuum oven to obtain 11.5g of compound 1-2 (83%).

[0398] Synthesis of Compounds 1-3

[0399] 45mL of dichloromethane (MC) is mixed with 5.00g (3.16mmol) of compound 1-2, and 1.70g (6.62mmol) of silver trifluoromethanesulfonate (AgOTf) and 15mL of methanol are added thereto.Then, by using aluminum foil to block light, the mixture is stirred at room temperature for about 18 hours.The gained is filtered using diatomite to remove the solid formed therefrom and remove the solvent in the gained filtrate under reduced pressure, so as to obtain solid (compound 1-3).The solid is used in the reaction below without any further purification.

[0400] Synthesis of Compounds 1-4

[0401] 10 g (23.07 mmol) of 2-bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole), 6.33 g (23.07 mmol) of 4,4,5,5-tetramethyl-2-(5-methylbenzo[b]thiophen-3-yl)-1,3,2-dioxaborolane, 0.80 g (0.69 mmol) of Pd(PPh 3 ) 4 , and 15.94 g (117.27 mmol) of K 2 CO 3 The mixture was mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water. The mixture was then stirred under reflux for 18 hours. Once the temperature was lowered to room temperature, the organic layer was extracted with MC, and anhydrous magnesium sulfate (MgSO 4 ) to dry the organic layer. The resultant was filtered, and the solvent in the filtrate was removed under reduced pressure. The residue was purified by column chromatography using ethyl acetate (EA) and hexane in a ratio of 1:3 (volume ratio, the same below) to obtain 10.51 g of compound 1-4 (91%).

[0402] Synthesis of compound 1

[0403] 5.00 g (5.15 mmol) of compound 1-3 and 2.84 g (5.67 mmol) of compound 1-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N, N-dimethylformamide. Then, the mixture was stirred at 120 ° C under reflux for 18 hours to react. Then, the temperature was lowered. The resulting mixture was filtered to obtain a solid. Then, the solid was fully washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane in a ratio of 1:50 to obtain 2.20 g of compound 1 (31%). The resulting compound was confirmed by using mass spectrometry and high performance liquid chromatography (HPLC) analysis. HRMS (MALDI): For C 70H 79 Ir 4 SSi 2 Calculated value: m / z 1256.5193, found: 1256.5198.

[0404] Synthesis Example 2 (Synthesis of Compound 2)

[0405] The synthesis of compound 2 is shown in Scheme 2.

[0406] Solution 2

[0407]

[0408] Synthesis of Compound 2-4

[0409] 10 g (23.07 mmol) of 2-bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole), 3.74 g (23.07 mmol) of benzofuran-3-ylboronic acid, 0.80 g (0.69 mmol) of Pd(PPh 3 ) 4 , and 15.94 g (117.27 mmol) of K 2 CO 3 The mixture was mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water. The mixture was then stirred under reflux for 18 hours. Once the temperature was lowered to room temperature, the organic layer was extracted with MC, and anhydrous magnesium sulfate (MgSO 4 ) to dry the organic layer. The resultant was filtered, and the solvent in the obtained filtrate was removed under reduced pressure. The residue was purified by column chromatography using EA and hexane at a ratio of 1:3 to obtain 8.69 g of compound 2-4 (80%).

[0410] Synthesis of compound 2

[0411] 3.00 g (3.09 mmol) of compound 1-3 and 1.60 g (3.40 mmol) of compound 2-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N, N-dimethylformamide. Then, the mixture was stirred at 120 ° C under reflux for 18 hours to react. Then, the temperature was lowered. The resulting mixture was filtered to obtain a solid. Then, the solid was fully washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane in a ratio of 1:50 to obtain 1.06 g of compound 2 (28%). The resulting compound was confirmed by using mass spectrometry and high performance liquid chromatography (HPLC) analysis. HRMS (MALDI): For C 69 H 77 Ir4 OSi 2 Calculated for m / z 1226.5265, found 1226.5269.

[0412] Synthesis Example 3 (Synthesis of Compound 3)

[0413] The synthesis of compound 3 is shown in Scheme 3.

[0414] Solution 3

[0415]

[0416] Synthesis of Compound 3-4

[0417] 5 g (11.54 mmol) of 2-bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole), 2.93 g (11.54 mmol) of 5-phenylbenzothiophen-3-ylboronic acid, 0.40 g (0.35 mmol) of Pd(PPh 3 ) 4 , and 7.97 g (58.63 mmol) of K 2 CO 3 The mixture was mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water. The mixture was then stirred under reflux for 18 hours. Once the temperature was lowered to room temperature, the organic layer was extracted with MC, and anhydrous magnesium sulfate (MgSO 4 ) to dry the organic layer. The resultant was filtered, and the solvent in the obtained filtrate was removed under reduced pressure. The residue was purified by column chromatography using EA and hexane at a ratio of 1:3 to obtain 5.46 g of compound 3-4 (84%).

[0418] Synthesis of compound 3

[0419] 2.20 g (2.27 mmol) of compound 1-3 and 1.41 g (2.50 mmol) of compound 3-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N, N-dimethylformamide. Then, the mixture was stirred at 120 ° C under reflux for 18 hours to react. Then, the temperature was lowered. The resulting mixture was filtered to obtain a solid. Then, the solid was fully washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane in a ratio of 1:50 to obtain 0.87 g of compound 3 (29%). The resulting compound was confirmed by using mass spectrometry and high performance liquid chromatography (HPLC) analysis. HRMS (MALDI): For C 75 H 81 Ir 4 SSi2 Calculated value: m / z 1318.5350, found value: 1318.5352

[0420] Synthesis Example 4 (Synthesis of Compound 4)

[0421] The synthesis of compound 4 is shown in Scheme 4.

[0422] Solution 4

[0423]

[0424] Synthesis of compound 4-4

[0425] 6.32 g (14.59 mmol) of 2-bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole), 3.80 g (14.59 mmol) of 2-(benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.42 g (0.36 mmol) of Pd(PPh 3 ) 4 , and 10.08 g (72.95 mmol) of K 2 CO 3 The mixture was mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water. The mixture was then stirred under reflux for 18 hours. Once the temperature was lowered to room temperature, the organic layer was extracted with MC, and anhydrous magnesium sulfate (MgSO 4 ) to dry the organic layer. The resultant was filtered, and the solvent in the obtained filtrate was removed under reduced pressure. The residue was purified by column chromatography using EA and hexane at a ratio of 1:3 to obtain 5.33 g of compound 4-4 (75%).

[0426] Synthesis of compound 4

[0427] 1.50 g (1.55 mmol) of compound 1-3 and 0.75 g (1.55 mmol) of compound 4-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N, N-dimethylformamide. Then, the mixture was stirred at 120 ° C under reflux for 18 hours to react. Then, the temperature was lowered. The resulting mixture was filtered to obtain a solid. Then, the solid was fully washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane in a ratio of 1:50 to obtain 0.40 g of compound 4 (21%). The resulting compound was confirmed by using mass spectrometry and HPLC analysis. HRMS (MALDI): For C 69 H 77 Ir 4 SSi2 Calculated value: m / z 1242.5037, found: 1242.5041

[0428] Synthesis Example 5 (Synthesis of Compound 5)

[0429] The synthesis of compound 5 is shown in Scheme 5.

[0430] Solution 5

[0431]

[0432] Synthesis of compound 5-4

[0433] 3.00 g (6.92 mmol) of 2-bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole), 1.22 g (6.92 mmol) of (5-methylbenzofuran-3-yl)boronic acid, 0.16 g (0.14 mmol) of Pd(PPh 3 ) 4 , and 4.78 g (34.60 mmol) of K 2 CO 3 The mixture was mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water. The mixture was then stirred under reflux for 18 hours. Once the temperature was lowered to room temperature, the organic layer was extracted with MC, and anhydrous magnesium sulfate (MgSO 4 ) to dry the organic layer. The resultant was filtered, and the solvent in the obtained filtrate was removed under reduced pressure. The residue was purified by column chromatography using EA and hexane at a ratio of 1:3 to obtain 2.92 g of compound 5-4 (87%).

[0434] Synthesis of compound 5

[0435] 2.00 g (2.06 mmol) of compound 1-3 and 1.10 g (2.27 mmol) of compound 5-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N, N-dimethylformamide. Then, the mixture was stirred at 120 ° C under reflux for 18 hours to react. Then, the temperature was lowered. The resulting mixture was filtered to obtain a solid. Then, the solid was fully washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane in a ratio of 1:50 to obtain 0.89 g of compound 5 (35%). The resulting compound was confirmed by using mass spectrometry and HPLC analysis. HRMS (MALDI): For C 70 H 79 Ir 4 OSi 2Calculated value: m / z 1240.5422, Found: 1240.5422

[0436] Synthesis Example 6 (Synthesis of Compound 821)

[0437] The synthesis of compound 821 is shown in Scheme 6.

[0438] Solution 6

[0439]

[0440] Synthesis of Compound 821-2

[0441] 10 g (52.83 mmol) of compound 821-1 (5-(methyl-d3)-2-(4-(methyl-d3)phenyl)pyridine) and 8.47 g (24.01 mmol) of iridium chloride were mixed with 90 mL of ethoxyethanol and 30 mL of distilled water. Then, the mixture was stirred under reflux for 24 hours to react, and then the temperature was lowered to room temperature. A solid was formed therefrom and the solid was separated by filtration. The solid was fully washed with water, methanol, and hexane in the order stated and dried in a vacuum oven to obtain 12.04 g of compound 821-2 (83%).

[0442] Synthesis of Compound 821-3

[0443] 45mL of MC is mixed with the compound 821-2 of 3.00g (2.48mmol), and the solution in the methanol of 15mL of which the AgOTf of 1.40g (5.46mmol) is dissolved is added thereto.Then, at room temperature, the mixture is stirred for about 18 hours to react while blocking light by using aluminum foil.The gained is filtered using diatomite to remove the solid formed therefrom and remove the solvent in the gained filtrate under reduced pressure, so as to obtain a solid (compound 821-3).The solid is used in the reaction below without any further purification.

[0444] Synthesis of Compound 821-4

[0445] 3 g (10.98 mmol) of 2-bromo-1-phenyl-1H-benzo[d]imidazole, 2.33 g (10.98 mmol) of 4-naphtho[2,1-b]furan-1-ylboronic acid, 0.25 g (0.22 mmol) of Pd(PPh 3 ) 4 , and 7.59 g (54.90 mmol) of K 2 CO 3The mixture was mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water. The mixture was then stirred under reflux for 18 hours. Once the temperature was lowered to room temperature, the organic layer was extracted with MC, and anhydrous magnesium sulfate (MgSO 4 ) to dry the organic layer. The resultant was filtered, and the solvent in the obtained filtrate was removed under reduced pressure. The residue was purified by column chromatography using EA and hexane at a ratio of 1:3 to obtain 2.57 g of compound 821-4 (65%).

[0446] Synthesis of compound 821

[0447] 3 g (2.56 mmol) of compound 821-3 and 1.02 g (2.82 mmol) of compound 821-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N, N-dimethylformamide. Then, the mixture was stirred at 120 ° C under reflux for 18 hours to react. Then, the temperature was lowered. The resulting mixture was filtered to obtain a solid. Then, the solid was fully washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane in a ratio of 1:50 to obtain 0.74 g of compound 821 (31%). The resulting compound was confirmed by using mass spectrometry and HPLC analysis. HRMS (MALDI): for C 51 H 27 D 12 Ir 4 Calculated for O: m / z 928.3506, found: 928.3504.

[0448] Synthesis Example 7 (Synthesis of Compound 822)

[0449] The synthesis of compound 822 is shown in Scheme 7.

[0450] Solution 7

[0451]

[0452] Synthesis of Compound 822-2

[0453] 5 g (32.22 mmol) of compound 822-1 (2-phenylpyridine) and 5.17 g (14.65 mmol) of iridium chloride were mixed with 90 mL of ethoxyethanol and 30 mL of distilled water. Then, the mixture was stirred for about 24 hours while refluxing to react, and then the temperature was lowered to room temperature. A solid was formed therefrom and the solid was separated by filtration. The solid was fully washed with water, methanol, and hexane in the order stated and dried in a vacuum oven to obtain 5.50 g of compound 822-2 (70%).

[0454] Synthesis of Compound 822-3

[0455] 45mL of MC is mixed with 3.00g (2.80mmol) of compound 822-2, and to it is added a solution in which 1.29g (5.02mmol) of AgOTf is dissolved in 15mL of methanol. Then, at room temperature, the mixture is stirred for about 18 hours to react while blocking light by using aluminum foil. Gains are filtered using diatomite to remove the solid formed therefrom and remove the solvent in the obtained filtrate under reduced pressure, so as to obtain a solid (compound 822-3). The solid is used in the reaction below without any further purification.

[0456] Synthesis of compound 822

[0457] 2 g (2.80 mmol) of compound 822-3 and 1.45 g (3.08 mmol) of compound 2-4 were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N, N-dimethylformamide. Then, the mixture was stirred at 120 ° C under reflux for 18 hours to react. Then, the temperature was lowered. The resulting mixture was filtered to obtain a solid. Then, the solid was fully washed with ethanol and hexane. Then, the solid was purified by column chromatography using EA and hexane in a ratio of 1:50 to obtain 0.54 g of compound 822 (20%). The resulting compound was confirmed by using mass spectrometry and HPLC analysis. HRMS (MALDI): for C 55 H 45 Ir 4 Calculated for O: m / z 970.3223, found: 970.3227.

[0458] Synthesis Example 8 (Synthesis of Compound 767)

[0459] The synthesis of compound 767 is shown in Scheme 8.

[0460] Solution 8

[0461]

[0462] Synthesis of Compound 767-2

[0463] 5g (9.99mmol) of compound 1-4 and 1.76g (5.00mmol) of iridium chloride were mixed with 90mL of ethoxyethanol and 30mL of distilled water. Then, the mixture was stirred under reflux for 24 hours to react, and the temperature was then lowered to room temperature. Solid was formed therefrom and the solid was separated by filtration. The solid was fully washed with water, methanol and hexane in the order stated and dried in a vacuum oven, thereby obtaining 4.91g of compound 767-2 (80%).

[0464] Synthesis of compound 767

[0465] 4 g (1.63 mmol) of compound 767-2, 1.80 g (18 mmol) of acetylacetone, and 2.49 g (18 mmol) of K 2 CO 3 Added to 60 mL of 2-ethoxyethanol, followed by stirring at room temperature for 24 hours. The obtained solid product was removed therefrom by filtration, followed by column chromatography using ethyl acetate and hexane, thereby obtaining 0.63 g of compound 767 (30%). The obtained compound was confirmed by using mass spectrometry and HPLC analysis. HRMS (MALDI): for C 73 H 71 Ir 4 O 2 S 2 Calculated value: m / z 1292.4648, found: 1292.4644.

[0466] Example 1

[0467] The glass substrate on which ITO was patterned as an anode was cut into a size of 50 millimeters (mm)×50 mm×0.5 mm, ultrasonically treated in isopropyl alcohol and water for 5 minutes each, and cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Subsequently, the glass substrate was mounted on a vacuum deposition apparatus.

[0468] Compound HT3 and compound F6-TCNNQ were co-deposited on the anode in a weight ratio of 98:2 to form a Then, compound HT3 is vacuum deposited on the hole injection layer to form a hole injection layer having a thickness of The hole transport layer has a thickness of .

[0469] Subsequently, compound CBP (as a host) and compound 1 (as a dopant) were co-deposited on the hole transport layer at a weight ratio of 95:5 to form a The thickness of the emission layer.

[0470] Compound ET3 and compound ET-D1 were co-deposited on the emission layer at a volume ratio of 50:50 to form a The electron transport layer is formed by depositing compound ET-D1 on the electron transport layer to form a An electron injection layer having a thickness of , and Al is vacuum deposited on the electron injection layer to form a A cathode with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.

[0471]

[0472] Examples 2-7 and Comparative Example A

[0473] An organic light emitting device was manufactured in substantially the same manner as in Example 1, except that in the formation of the emission layer, the compound shown in Table 2 was used as a dopant instead of Compound 1.

[0474] Evaluation Example 1

[0475] The driving voltage (V), maximum external quantum efficiency (Max EQE, %), and roll-off ratio (%) of the organic light-emitting devices manufactured in Examples 1-7 and Comparative Example A were evaluated. The evaluation results are shown in Table 2. A Keithley 2400 current voltage meter and a luminance meter (Minolta Cs-1000A) were used in the evaluation. The roll-off ratio was calculated by Equation 20. The Max EQE in Table 2 is shown as a relative value (%).

[0476] Equation 20

[0477] Roll-off ratio = {1-((Efficiency at 8,000 nits) / Maximum luminous efficiency)}×100%

[0478] Table 2

[0479]

[0480]

[0481] Referring to Table 2, it was found that compared with the organic light emitting device of Comparative Example A, the organic light emitting devices of Examples 1 to 7 had improved driving voltage, improved external quantum efficiency, and improved roll-off ratio.

[0482] Example 8 and Comparative Example B

[0483] An organic light emitting device was manufactured in substantially the same manner as in Example 1, except that in the formation of the emission layer, a compound shown in Table 3 was used instead of Compound 1 as a dopant.

[0484] Evaluation Example 2

[0485] The driving voltage (V), Max EQE (%), and roll-off ratio (%) of the organic light emitting devices manufactured in Example 8 and Comparative Example B were evaluated in substantially the same manner as in Evaluation Example 1. The evaluation results are shown in Table 3. The Max EQE in Table 3 is shown as a relative value (%).

[0486] Table 3

[0487]

[0488]

[0489] Referring to Table 3, it was found that compared with the organic light emitting device of Comparative Example B, the organic light emitting device of Example 8 had improved driving voltage, improved external quantum efficiency, and improved roll-off ratio.

[0490] As is clear from the foregoing description, the organometallic compound may have excellent electrical characteristics, and thus, an electronic device including the organometallic compound, such as an organic light-emitting device, may have improved driving voltage, improved external quantum efficiency, and / or improved roll-off ratio characteristics.

[0491] It should be understood that the exemplary embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each exemplary embodiment should be considered as usable features or aspects of other exemplary embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that various changes in form and detail may be made therein without departing from the spirit and scope as defined by the appended claims.

Claims

1. An organometallic compound represented by formula 1: Formula 1 M(L1) n1 (L2) n2 in, In formula 1, M is iridium (Ir), L1 is a ligand represented by formula 2, n1 is 1 or 2, and when n1 is 2, the two L1 groups are the same as or different from each other, L2 is a bidentate ligand, n2 is 1 or 2, and when n2 is 2, the two L2 groups are the same as or different from each other, The sum of n1 and n2 is 3, L1 is different from L2. Formula 2 Among them, in formula 2, A 21 -A 24 Each independently is C, X1 is O or S, L 13 is unsubstituted or replaced by at least one R 10a Substituted phenyl groups, R1 is independently Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, or C1-C 20 Alkoxy; C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 10 Alkyl, or a combination thereof; or cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, or naphthyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, deuterated C2-C 20 Alkyl, C1-C 20 Alkoxy, or a combination thereof, R2 and R 10a Each independently Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, or C1-C 20 alkoxy; or C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 10 Alkyl, or a combination thereof, R3 is unsubstituted or substituted phenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, deuterated C2-C 20 Alkyl, C1-C 20 Alkoxy, or a combination thereof, b1 is an integer from 0 to 10, b2 is an integer from 0 to 4, In formula 2, The group represented by formula 2(1) is represented by: Wherein, in formula 2(1), X1 is as defined above, L2 is a ligand represented by formula 3-1: Among them, in formula 3-1, Y 11 For N, Z 11 -Z 14 and Z2 are each independently: Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, or C1-C 20 Alkoxy; C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 10 Alkyl, or a combination thereof; or -Si(Q3)(Q4)(Q5) or Ge(Q3)(Q4)(Q5), Where Q3-Q5 are each independently: deuterium, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, or sec-isopentyl, each unsubstituted or substituted with deuterium, C1-C 10 Alkyl, or a combination thereof, In formula 3-1, The group represented by is represented by one of formulae 3-1(1) to 3-1(16): Among them, in 3-1(1) to 3-1(16), Z 21 -Z 24 Each is understood by reference to Z2, wherein Z 21 -Z 24 Not hydrogen, In the above formulas, * and *' each represent a binding site with M in Formula 1, and *" indicates the binding site with the adjacent atoms.

2. The organometallic compound according to claim 1, wherein R2 is Hydrogen, deuterium, -F, cyano, C1-C 20 Alkyl, or C1-C 20 alkoxy; or C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 10 alkyl, or a combination thereof.

3. The organometallic compound according to claim 1, wherein the The group represented by is represented by one of formulae 2-1 to 2-16: in, In formulas 2-1 to 2-16, X1 is understood by referring to the description of X1 in claim 1, R 11 -R 14 Each is understood by referring to the description of R1 in claim 1, wherein R 11 -R 14 Each is not hydrogen, * represents the binding site with M in Formula 1, and *" indicates the binding site with the adjacent carbon atom.

4. The organometallic compound according to claim 1, wherein Z in Formula 3-1 11 -Z 14 and Z2 are each independently deuterated; -Si(Q3)(Q4)(Q5); -Ge(Q3)(Q4)(Q5); or C1-C 20 alkyl.

5. The organometallic compound according to claim 1, wherein Z in Formula 3-1 12 -Si(Q3)(Q4)(Q5); -Ge(Q3)(Q4)(Q5); or C1-C 20 alkyl.

6. The organometallic compound according to claim 1, wherein Z in Formula 3-1 12 is -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), and Z 13 Not hydrogen or methyl.

7. The organometallic compound according to claim 1, wherein the The group represented by is represented by one of formulae 3-1-1 to 3-1-16: in, In formulas 3-1-1 to 3-1-16, Z 11 -Z 14 By referring to Z in claim 1 11 -Z 14 And understand, among them Z 11 -Z 14 Not hydrogen, * and *' each represent a binding site with M in Formula 1, and *" indicates the binding site with the adjacent atoms.

8. The organometallic compound according to claim 1, comprising: At least one deuterium atom.

9. The organometallic compound according to claim 1, wherein the organometallic compound is one of the following compounds:

10. An organic light emitting device comprising: a first electrode; a second electrode; as well as an organic layer disposed between the first electrode and the second electrode and including an emission layer; The organic layer comprises at least one organic metal compound as claimed in any one of claims 1 to 9. The organic light emitting device of claim 10 , wherein the emission layer comprises the organic metal compound.

12. An electronic device comprising the organic light emitting device according to any one of claims 10 and 11.

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