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

Abstract

Disclosed are an organic metal compound, an organic light-emitting device and a diagnostic composition comprising the same. The organic metal compound is represented by Formula 1, wherein in Formula 1, M, L 1 , L 2 , n1, and n2 are each independently the same as described herein. 1 ) n1 (L 2 ) n2。

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefits of Korean Patent Application No. 10-2019-0044480 filed on April 16, 2019 in the Korean Intellectual Property Office and all rights arising therefrom, the contents of which are incorporated herein by reference in their entirety. Technical Field

[0003] Embodiments relate to organometallic compounds, organic light emitting devices including the organometallic compounds, and diagnostic compositions including the organometallic compounds. Background Art

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

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

[0006] Luminescent compounds can be used to monitor, sense or detect a variety of biological materials, including cells and proteins. Examples of such luminescent compounds are phosphorescent luminescent compounds. Summary of the invention

[0007] Aspects of the present disclosure provide novel organometallic compounds, organic light-emitting devices including the same, and diagnostic compositions including the novel organometallic compounds.

[0008] Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments.

[0009] One aspect of the present disclosure provides an organometallic compound represented by the following Formula 1:

[0010] Formula 1

[0011] M(L 1 ) n1 (L 2 ) n2 .

[0012] In formula 1,

[0013] M may be a transition metal,

[0014] L 1 may be a ligand represented by Formula 2,

[0015] n1 can be 1, 2, or 3, wherein when n1 is 2 or greater, two or more L 1 may be the same or different from each other,

[0016] L 2 It can be a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand,

[0017] n2 can be 0, 1, 2, 3, or 4, wherein when n2 is 2 or greater, two or more L 2 may be the same as or different from each other, and

[0018] L 1 and L 2 Can be different from each other:

[0019] Formula 2

[0020]

[0021] In formula 2,

[0022] X 1 Can be C, N, Si, or P,

[0023] X 21 Can be C or N,

[0024] Cyclo 1 and CY 21 Can be independently C 5 -C 30 Carbocyclic group or C 2 -C 30 Heterocyclic groups,

[0025] X 2 and X 3 can be independently O, S, Se, or C(R 2 ), where X 2 or X 3 It can be O, S, or Se,

[0026] X 4 Can be N or C(R 4 ),

[0027] X 5 Can be N or C(R 5 ),

[0028] R 1 , R 2 , R 4 , R5 , and R 21 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 3 -C 10 Cycloalkyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 7 -C 60 Arylalkyl (e.g. substituted or unsubstituted phenyl (C 1 -C 20 alkyl) group), substituted or unsubstituted C 1 -C 60 Heteroaryl, 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 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ),

[0029] a1 and a21 can each independently be an integer of 0-20,

[0030] Cyclo 1 and R 2 may not be connected to each other, and R 1 and R 2 They may not be connected to each other.

[0031] L 11 may be unsubstituted or substituted with at least one R 10a C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a C 2 -C 30 Heterocyclic groups,

[0032] b11 can be an integer from 0 to 10, wherein when b11 is 0, *-(L 11 ) b11 The group represented by -*' may be a single bond, and when b11 is 2 or more, two or more L 11 may be the same or different from each other,

[0033] Multiple adjacent R 21 Two or more of may be optionally linked to form an unsubstituted or substituted R 10a C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a C 2 -C 30 Heterocyclic groups,

[0034] R 10a Can be related to R 21 The same as defined,

[0035] * and *' each represent a binding site with M in Formula 1,

[0036] 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 3 -C 10Cycloalkyl, substituted C 2 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 2 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 7 -C 60 Arylalkyl (e.g. substituted phenyl (C 1 -C 20 alkyl) group), substituted C 2 -C 60 Heteroaralkyl, substituted C 1 -C 60 The substituent(s) of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be:

[0037] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy;

[0038] 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 , -CF2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 2 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl (e.g. phenyl (C 1 -C 20 Alkyl) group), C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 ), or any combination thereof;

[0039] C 3 -C 10 Cycloalkyl, C 2 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl (e.g. phenyl (C 1 -C 20 Alkyl) group), C 1 -C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group;

[0040] Each of C is substituted by 3 -C 10 Cycloalkyl, C 2 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl (e.g. phenyl (C 1 -C 20 Alkyl) group), C 1 -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, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 2 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl (e.g. phenyl (C 1 -C 20 Alkyl) group), C1 -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 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 ), or any combination thereof;

[0041] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 ), or -P(=O)(Q 38 )(Q 39 );or

[0042] Any combination of these, and

[0043] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 may be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, 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 2 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Alkyl, C 6-C 60 Aryl, or any combination thereof substituted C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl (e.g. phenyl (C 1 -C 20 Alkyl) group), C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group.

[0044] Another aspect of the present disclosure provides an organic light emitting device including: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one organic metal compound represented by Formula 1.

[0045] The organic metal compound represented by Formula 1 may be included in the emission layer of the organic layer and may serve as a dopant.

[0046] Another aspect of the present disclosure provides a diagnostic composition comprising at least one organometallic compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0047] By combining Figure 1 These and / or other aspects will become clear and more readily understood from the following description of the embodiments contemplated herein. Figure 1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment. DETAILED DESCRIPTION

[0048] Embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the present embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the following description of the embodiments is provided only by reference to the accompanying drawings to illustrate aspects of the present description. As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. Expressions such as "at least one (kind)", when before or after a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

[0049] It will be understood that when an element is referred to as being “on” another element, it can be directly on the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.

[0050] It will be understood that although the terms "first", "second", "third", etc. may be used herein to describe various elements, components, regions, layers and / or parts, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or part from another element, component, region, layer or part. Therefore, without departing from the teachings herein, the first element, component, region, layer or part discussed below may be referred to as a second element, component, region, layer or part.

[0051] The terms used herein are only for the purpose of describing specific embodiments and are not intended to be restrictive. As used herein, the singular forms "one (kind)" and "the (the)" are intended to include plural forms, including "at least one (kind)", unless the content clearly indicates otherwise. "At least one (kind)" will not be interpreted as limiting "one" or "a kind". "Or" means "and / or". As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. It will be further understood that the term "include" or "comprising" when used in this specification indicates that there are stated features, regions, wholes, steps, operations, elements, and / or components, but does not exclude the presence or addition of other features, regions, wholes, steps, operations, elements, components, and / or their collections.

[0052] In addition, relative terms such as "lower" or "bottom" and "upper" or "top" may be used herein to describe the relationship of one element to another element as shown in the figure. It will be understood that, in addition to the orientation depicted in the figure, relative terms are also intended to include different orientations of the device. For example, if the device in one of the figures is turned over, the element described as being on the "lower" side of the other element will be oriented on the "upper" side of the other element. Therefore, depending on the specific orientation of the figure, the exemplary term "lower" may include both "lower" and "upper" orientations. Similarly, if the device in one of the figures is turned over, the element described as "below" or "below" the other element will be oriented "above" the other element. Therefore, the exemplary terms "below..." or "below..." may include both "above..." and "below..." orientations.

[0053] As used herein, "about" or "approximately" includes the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" may mean that the deviation from the stated value is within one or more standard deviations, or within ±10%, or 5%.

[0054] Unless otherwise defined, all terms (including technical and scientific terms) used in this article have the same meaning as commonly understood by ordinary technicians in the field to which the present disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as their meanings consistent with their meanings in the context of the present disclosure and the relevant art, and will not be interpreted in an idealized or excessive formal sense unless clearly defined in this article.

[0055] Exemplary embodiments are described herein with reference to cross-sectional views as schematic diagrams of idealized embodiments. Thus, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are expected. Therefore, the embodiments described herein should not be construed as being limited to the specific shapes of the regions as shown herein, but rather include deviations in shape resulting from, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. In addition, the illustrated sharp corners may be rounded. Therefore, the regions shown 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.

[0056] One aspect of the present disclosure provides an organometallic compound represented by the following Formula 1:

[0057] Formula 1

[0058] M(L 1 ) n1 (L 2 ) n2 .

[0059] M in Formula 1 may be a transition metal.

[0060] For example, M can be a first row transition metal, a second row transition metal, or a third row transition metal of the periodic table.

[0061] In one embodiment, M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0062] In one embodiment, M may be Ir, Pt, Os, or Rh, but embodiments of the present disclosure are not limited thereto.

[0063] L in Formula 1 1 may be a ligand represented by Formula 2, and n1 in Formula 1 represents L in Formula 1 1 The number of L can be 1, 2, or 3. When n1 is 2 or greater, two or more L 1 Can be the same or different from each other:

[0064] Formula 2

[0065]

[0066] Formula 2 may be the same as described below.

[0067] For example, n1 may be 1 or 2.

[0068] L in Formula 1 2 It can be a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand, and n2 in Formula 1 represents L 2 The number of L can be 0, 1, 2, 3, or 4. When n2 is 2 or greater, two or more L 2 They may be the same or different from each other. 2 May be the same as described below.

[0069] For example, n2 in Formula 1 may be 1 or 2.

[0070] In formula 1, L 1 and L 2 Can be different from each other.

[0071] In one embodiment, 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.

[0072] In formula 2, X 1 can be C, N, Si, or P, and X 21 Can be C or N.

[0073] For example, in Formula 2, X 21 Can be C.

[0074] In Formula 2, ring CY 1 and CY 21 Can be independently C 5 -C 30 Carbocyclic group or C 2 -C 30 Heterocyclic group.

[0075] For example, CY 1 and CY 21 Each may independently 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.

[0076] The first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, Azole group, iso Azole group, Oxadiazole group, isocyanate Oxadiazole group, Triazole group, iso a triazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothitriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiole group, a diazathiole group, or a triazathiole group.

[0077] The second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0078] In one embodiment, cycloCY 1 and CY 21 can be independently a cyclopentene group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, Azabenzophosphoside group, azaindene group, azabenzosilole group, azabenzogermanol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborol group, azadibenzophosphoside group, azafluorene group, azadibenzosilole group, azadibenzogermanol group, azadibenzothiophene group , azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, Azole group, iso azole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo Azole group, benzothiazole group, benzo A oxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group, but the embodiments of the present disclosure are not limited thereto.

[0079] In one embodiment, cycloCY 1 It may be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, an adamantane group, a norbornane group, a norbornene group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a phenyl group, a naphthalene group, a fluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, group, pyrrole group, thiophene group, furan group, imidazole group, pyrazole group, thiazole group, isothiazole group, Azole group, iso azole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, isoindole group, indole group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, quinoxaline group, quinazoline group, cinnoline group, carbazole group, phenanthroline group, benzimidazole group, benzofuran group, benzothiophene group, isobenzothiazole group, benzo Azole group, isobenzo Azole group, triazole group, tetrazole group, A oxadiazole group, a triazine group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a benzocarbazole group, a dibenzocarbazole group, an imidazopyridine group, or an imidazopyrimidine group, but embodiments of the present disclosure are not limited thereto.

[0080] In formula 2, X 2 and X 3 can be independently O, S, Se, or C(R 2 ), where X 2 or X 3 It can be O, S, or Se.

[0081] For example, in Formula 2, i)X 2 can be O, S, or Se, and X 3 Can be C(R 2 ); or ii) X 2 Can be C(R 2 ), and X 3 It can be O, S, or Se.

[0082] In formula 2, X 4 Can be N or C(R4 ), and X 5 Can be N or C(R 5 ).

[0083] For example, X 4 Can be C(R 4 ), and X 5 Can be C(R 5 ).

[0084] In formula 2, R 1 , R 2 , R 4 , R 5 , R 21 , and R 10a 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 3 -C 10 Cycloalkyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 7 -C 60 Arylalkyl (e.g. substituted or unsubstituted phenyl (C 1 -C 20 alkyl) group), substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60heteroarylalkyl, 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 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ), where Q 1 -Q 9 Each is the same as described above.

[0085] For example, R 1 , R 2 , R 4 , R 5 , R 21 , and R 10a Can be independently:

[0086] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF 5 , C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy;

[0087] Each of C is substituted by 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof;

[0088] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, each unsubstituted or substituted yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, Oxazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -Si(Q 33 )(Q 34 )(Q 35 ), or any combination thereof; or

[0089] -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ),and

[0090] Q 1 -Q 9 and Q 33 -Q 35 Can be independently:

[0091] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;or

[0092] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each unsubstituted or substituted with: deuterium, C 1 -C10 An alkyl group, a phenyl group, or any combination thereof, but the embodiments of the present disclosure are not limited thereto.

[0093] In Formula 2, a1 and a21 each represent R 1 The number and R 21 When a1 is 2 or more, two or more R 1 may be the same as or different from each other, and when a21 is 2 or greater, two or more R 21 Can be the same as or different from each other.

[0094] In Formula 2, ring CY 1 and R 2 are not connected to each other, and R 1 and R 2 Not connected to each other.

[0095] In one embodiment, in Formula 2, The groups represented by may be each unsubstituted or substituted with a1 number of R 1 Substituted C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 30 Aryl, C 2 -C 30 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group,

[0096] In formula 2, R 1 and R 2 Can be independently:

[0097] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, or -SF 5 ;or

[0098] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 2 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, or C 2 -C 10 Heterocycloalkenyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano, C 1 -C 20 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof, and

[0099] a1 can be an integer from 0 to 10.

[0100] a1, R 1 , C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 2 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 30 Aryl, C 2 -C 30 The detailed description of the heteroaryl group, the monovalent non-aromatic condensed polycyclic group, and the monovalent non-aromatic condensed heteropolycyclic group is the same as described above.

[0101] In one embodiment, in Formula 2, The groups represented by may be each unsubstituted or substituted with a1 number of R 1 Substituted phenyl, biphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl,

[0102] In formula 2, R 1 and R 2 Can be independently:

[0103] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, or -SF 5 ;or

[0104] each unsubstituted or substituted with the following methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl (n-nonyl), isononyl (isononyl), sec-nonyl (sec-nonyl), tert-nonyl (tert-nonyl), n-decyl, isodecyl, sec-decyl, tert-decyl, C 1 -C 10 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, or cycloheptenyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano, C 1 -C 20 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof, and

[0105] a1 may be an integer of 0-5, but the embodiments of the present disclosure are not limited thereto.

[0106] In one embodiment, in Formula 2, The group represented may be a group represented by one of formulae 10-13(1) to 10-13(18) or 10-13:

[0107]

[0108] In Formulas 10-13(1) to 10-13(18) and 10-13, R 1a -R 1e Each independently and with respect to R 1 The same as defined above, where R 1a -R 1e Each is not hydrogen, and * indicates a bonding site with an adjacent atom (eg, a carbon atom).

[0109] For example, in Formula 2, The group represented by may be a group represented by one of formulas 10-13 to 10-240, wherein R 1 , R 2 , R 4 , R 5 , R 21 , and R 10a can be independently hydrogen, deuterium, -F, cyano, nitro, -SF 5 、-CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , a group represented by one of formulae 9-1 to 9-19, a group represented by one of formulae 10-1 to 10-240, or -Si(Q 3 )(Q 4 )(Q 5 )(where Q 3 -Q 5 Same as described above), but the embodiments of the present disclosure are not limited thereto:

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116] In formulae 9-1 to 9-19 and 10-1 to 10-240, * represents a bonding site with an adjacent atom, Ph represents a phenyl group, and TMS represents a trimethylsilyl group.

[0117] In formula 2, L 11 may be 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 2 -C 30 A heterocyclic group, wherein R 10a Same as described above.

[0118] For example, L11 may be each unsubstituted or substituted with at least one R 10a substituted phenyl group, naphthalene group, anthracene group, phenanthrene group, benzo[9,10]phenanthrene group, pyrene group, group, a cyclopentadiene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzothiorrole group, a benzogermanol group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzothiorrole group, a dibenzogermanol group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzothiorrole group, an azabenzogermanol group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborol group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermanol group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran 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 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 A oxadiazole group, or a benzothiadiazole group, but the embodiments of the present disclosure are not limited thereto.

[0119] In formula 2, b11 represents L 11 The number of, and can be an integer of 0-10, wherein, when b11 is 0, by *-(L 11 ) b11 The group represented by -*' may be a single bond, and when b11 is 2 or more, two or more L 11 For example, b11 may be 0, 1, 2, or 3, but the embodiments of the present disclosure are not limited thereto.

[0120] In formula 2, multiple adjacent R 21Two or more of may be optionally linked to form an unsubstituted or substituted R 10a C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a C 2 -C 30 Heterocyclic groups (eg, each unsubstituted or substituted with at least one R 10a substituted phenyl group, cyclopentane group, cyclopentadienyl group, furan group, thiophene group, pyrrole group, silole group, indene group, benzofuran group, benzothiophene group, indole group, or benzosilole group), wherein R 10a About R 21 Same as defined in C 5 -C 30 Carbocyclic groups and C 2 -C 30 The detailed description of the heterocyclic group is the same as described above.

[0121] In Formula 2, * and *' each represent a binding site with M in Formula 1.

[0122] In one embodiment, in Formula 2, The group represented may be a group represented by one of the formulae CY21-1 to CY21-25:

[0123]

[0124]

[0125] In formulas CY21-1 to CY21-25,

[0126] X 21 and R 21 may each independently be the same as described herein,

[0127] X 22 Can be C(R 22 )(R 23 )、N(R 22 ), O, S, or Si (R 22 )(R 23 ),

[0128] R 22 -R 29 Can be independently related to R 21 The same as defined,

[0129] a26 can be an integer from 0 to 6.

[0130] a24 can be an integer from 0 to 4.

[0131] a23 can be an integer from 0 to 3.

[0132] a22 can be an integer from 0 to 2.

[0133] *" represents the binding site with the carbon atom of the adjacent 6-membered ring in Formula 2, and

[0134] * represents the binding site with M in Formula 1.

[0135] In one embodiment, in Formula 2, The group represented may be a group represented by one of the formulae CY21(1) to CY21(56) or a group represented by one of the formulae CY21-20 to CY21-25:

[0136]

[0137]

[0138] In formulas CY21(1) to CY21(56),

[0139] X 21 and R 21 may each independently be the same as described herein,

[0140] R 21a -R 21d Can be independently related to R 21 The same as defined above, where R 21 and R 21a -R 21d Each is not hydrogen,

[0141] *" represents the binding site with the carbon atom of the adjacent 6-membered ring in Formula 2, and

[0142] * represents the binding site with M in Formula 1.

[0143] In one embodiment, in Formula 2, The group represented by may be a group represented by one of the formulas CY21(1), CY21(3), or CY21(10) or a group represented by one of the formulas CY21-20 to CY21-25, but the embodiments of the present disclosure are not limited thereto. For example, in the formula CY21(10), R 21a and R 21b can be the same or different from each other. In one embodiment, in formula CY21 (10), R 21a and R 21b can be different from each other, and R 21a The number of carbon atoms included in R 21b The number of carbon atoms included in .

[0144] In one embodiment, in Formula 1, L 1 It may be a ligand represented by Formula 2A or 2B, but the embodiments of the present disclosure are not limited thereto:

[0145]

[0146] In Formulas 2A and 2B, X 1 , X 21 CY 1 CY 21 , X 4 , X 5 , R 1 , R 2 , R 21 、a1、a21、L 11 , b11, *, and *' may each independently be the same as described herein, wherein X 2 and X 3 Each independently may be O, S, or Se.

[0147] In formula 1, L 2 It may be a bidentate ligand connected to M of Formula 1 via O, S, N, C, P, Si, or As.

[0148] In one embodiment, in Formula 1, L 2 It may be a bidentate ligand represented by Formula 3:

[0149] Formula 3

[0150]

[0151] In formula 3,

[0152] X 31 and X 32 may be each independently O, S, N, C, P, Si, or As,

[0153] Indicates that X 31 and X 32 any groups of atoms connected to each other, and

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

[0155] For example, in Formula 3, i)X 31 and X 32 Each of them can be O; ii) X 31 Can be O, and X 32 Can be N, or iii) X 31 Can be N, and X 32It may be C, but the embodiments of the present disclosure are not limited thereto.

[0156] In one embodiment, in Formula 1, L 2 It can be a monodentate ligand, for example, I - Br - , Cl - , sulfide (sulfur), nitrate, azide (azide), hydroxide, cyanate, isocyanate, thiocyanate, water, acetonitrile, pyridine, ammonia, carbon monoxide, P(Ph) 3 、P(Ph) 2 CH 3 PPh(CH 3 ) 2 , P(CH 3 ) 3 , or any combination thereof, but the embodiments of the present disclosure are not limited thereto.

[0157] In one or more embodiments, in Formula 1, L 2 The ligand may be a bidentate ligand, for example, oxalate, acetylacetonate, picolinic acid, 1,2-bis(diphenylphosphino)ethane, 1,1-bis(diphenylphosphino)methane, glycinate, ethylenediamine, or any combination thereof, but the embodiments of the present disclosure are not limited thereto.

[0158] In one or more embodiments, in Formula 1, L 2 It may be a group represented by one of Formulae 3A-3F:

[0159]

[0160] In Formulas 3A-3F,

[0161] Y 13 Can be O, N, N(Z 1 )、P(Z 1 )(Z 2 ), or As(Z 1 )(Z 2 ),

[0162] Y 14 Can be O, N, N(Z 3 )、P(Z 3 )(Z 4 ), or As(Z 3 )(Z 4 ),

[0163] T 11 can be independently a single bond, a 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 unsubstituted or replaced by at least one Z 11 C 5 -C 30 Carbocyclic groups,

[0164] a11 can be an integer from 1 to 10.

[0165] Y 11 and Y 12 can be independently C or N,

[0166] T 21 Can be single bond, double bond, O, S, C(Z 11 )(Z 12 )、Si(Z 11 )(Z 12 ), or N(Z 11 ),

[0167] Cyclo 11 and CY 12 Can be independently C 5 -C 30 Carbocyclic group or C 2 -C 30 Heterocyclic groups,

[0168] A 1 Can be P or As,

[0169] Z 1 -Z 4 and Z 11 -Z 13 Can be independently related to R 21 The same as defined,

[0170] d1 and d2 can each independently be an integer from 0 to 10, and

[0171] * and *' each represent a binding site to M in Formula 1.

[0172] In Formulae 3A-3F, the C 5 -C 30 The carbocyclic group and the C 2 -C30 The heterocyclic groups may be independently 21 The same as defined.

[0173] For example, in Eq. 3D, The moiety represented by may be a group represented by one of the formulae CY11-1 to CY11-34, and / or

[0174] In formula 3C and 3D, The moiety represented by may be a group represented by one of the formulae CY12-1 to CY12-34:

[0175]

[0176]

[0177]

[0178] In formulas CY11-1 to CY11-34 and CY12-1 to CY12-34,

[0179] X 31 Can be O, S, N (Z 11 )、C(Z 11 )(Z 12 ), or Si(Z 11 )(Z 12 ),

[0180] X 41 Can be O, S, N (Z 21 )、C(Z 21 )(Z 22 ), or Si(Z 21 )(Z 22 ),

[0181] Y 11 , Y 12 , Z 1 , and Z 2 may each independently be the same as described herein,

[0182] Z 11 -Z 18 and Z 21 -Z 28 Can be independently related to R 21 The same as defined,

[0183] d12 and d22 can each independently be an integer from 0 to 2,

[0184] d13 and d23 can each independently be an integer from 0 to 3,

[0185] d14 and d24 can each independently be an integer of 0-4,

[0186] d15 and d25 can each independently be an integer of 0-5,

[0187] d16 and d26 can each independently be an integer from 0 to 6, and

[0188] In formulas 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 with T in formula 3D. 21 binding site.

[0189] In one embodiment, in Formula 1, L 2 It may be a group represented by one of Formulae 3-1(1) to 3-1(66) or one of Formulae 3-1(301) to 3-1(309), but the embodiments of the present disclosure are not limited thereto:

[0190]

[0191]

[0192]

[0193]

[0194]

[0195] In Formulas 3-1(1) to 3-1(66) and 3-1(301) to 3-1(309),

[0196] X 41 Can be O, S, N (Z 21 )、C(Z 21 )(Z 22 ), or Si(Z 21 )(Z 22 ),

[0197] Z 1 -Z 4 , Z 1a , Z 1b , Z 1c , Z 1d , Z 2a , Z 2b , Z 2c , Z 2d , Z 11 -Z 14 , and Z 21 -Z 22 Can be independently related to R21 The same as defined,

[0198] d14 can be an integer from 0 to 4.

[0199] d26 can be an integer from 0 to 6, and

[0200] * and *' each represent a binding site to M in Formula 1.

[0201] In one embodiment, the organometallic compound represented by Formula 1 may emit red light or green light. In one embodiment, the organometallic compound represented by Formula 1 may emit red light or green light each having a maximum emission wavelength of about 500 nm or more, for example, about 500 nm or more and about 650 nm or less.

[0202] As used herein, the term “azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzosilole group, azabenzogermanol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermanol group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, and azadibenzothiophene 5,5-dione” may be used. The “oxide group” each refers to a heterocyclic group having 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”, wherein at least one carbon atom constituting the cyclic group is substituted by N.

[0203] In one embodiment, the organometallic compound represented by Formula 1 may be one of Compounds 1 to 420, but embodiments of the present disclosure are not limited thereto:

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220] L of the organometallic compound represented by Formula 1 1 may be a ligand represented by Formula 2, and represents L 1 The number n1 may be 1, 2, or 3. That is, the organic metal compound must include at least one ligand represented by Formula 2 as a ligand bonded to the metal M.

[0221] X in the ligand represented by Formula 2 2 and X 3 are each independently O, S, Se, or C(R 2 ), where X 2 and X 3 One of them is O, S, or Se. That is, in Formula 2, the 5-membered ring (see Formula 2') does not include *=N-*' (* and *' each represent a binding site with an adjacent atom) as a ring-forming atom, and includes one of O, S, or Se. In addition, in Formula 2, the 5-membered ring and the 6-membered ring are fused to each other while sharing carbon 1 and carbon 2 (see Formula 2'). Therefore, the reduction of the intermolecular binding force of the organometallic compound represented by Formula 1 can be prevented. Therefore, the reduction of the life of an electronic device such as an organic light-emitting device including the organometallic compound represented by Formula 1 can be prevented.

[0222] Formula 2′

[0223]

[0224] The ligand represented by Formula 2 includes "Cyclo 1 ”. Therefore, the transition dipole moment in the orientation axis direction of Formula 1 increases, and the orientation (alignment) of the organic metal compound represented by Formula 1 can be improved, thereby improving the luminous efficiency of electronic devices including the organic metal compound represented by Formula 1, such as organic light-emitting devices.

[0225] At the same time, in Formula 2, ring CY 1 and R 2 are not connected to each other, and R 1 and R 2 Therefore, the transition dipole moment of Formula 1 can be prevented from deviating to a direction different from the orientation axis direction of Formula 1, thereby improving the light emission efficiency of an electronic device including the organometallic compound represented by Formula 1, such as an organic light emitting device.

[0226] The highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, and triplet state (T) energy level of some compounds of the organometallic compound represented by Formula 1 were evaluated by density functional theory (DFT) accompanied by Gaussian program based on B3LYP molecular structure optimization. 1 ) levels, and the results are shown in Table 1.

[0227] Table 1

[0228] Compound No. HOMO(eV) LUMO(eV) <![CDATA[T 1 (eV)]]> 16 -4.542 -1.694 2.008 101 -4.749 -1.682 2.177 116 -4.600 -1.671 2.081 146 -4.687 -1.651 2.150 216 -4.576 -1.747 2.075 316 -4.633 -1.747 2.116

[0229]

[0230] Referring to Table 1, it was confirmed that the organometallic compound represented by Formula 1 had such electrical characteristics as to be suitable for use as a dopant in an electronic device such as an organic light emitting device.

[0231] The synthesis method of the organometallic compound represented by Formula 1 can be understood by one of ordinary skill in the art by referring to the synthesis examples provided below.

[0232] Therefore, the organometallic compound represented by Formula 1 can be suitable for use in an organic layer of an organic light-emitting device, for example, as a dopant in an emission layer of the organic layer. Another aspect of the present disclosure provides an organic light-emitting device, comprising: a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer comprises at least one organometallic compound represented by Formula 1.

[0233] Due to including the organic layer including the organometallic compound represented by Formula 1, the organic light emitting device may have low driving voltage, high external quantum luminescence efficiency, low roll-off ratio, and long lifespan.

[0234] The organic metal compound represented by Formula 1 can be used between the electrode pairs of the organic light-emitting device. For example, the organic metal compound represented by Formula 1 can be included in the emission layer. In this regard, the organic metal compound can act as a dopant, and the emission layer can further include a host (that is, the amount of the organic metal compound represented by Formula 1 is less than the amount of the host). The emission layer can emit, for example, green light or red light.

[0235] As used herein, the expression “(the organic layer) includes the organic metal compound represented by Formula 1” may include the case where “(the organic layer) includes the same organic metal compound represented by Formula 1” and the case where “(the organic layer) includes two or more different organic metal compounds represented by Formula 1”.

[0236] For example, the organic layer may include only Compound 1 as the organic metal compound represented by Formula 1. In this regard, Compound 1 may be present only in the emission layer of the organic light-emitting device. In one embodiment, the organic layer may include Compound 1 and Compound 2 as the organic metal compound represented by Formula 1. In this regard, Compound 1 and Compound 2 may be present in the same layer (for example, Compound 1 and Compound 2 may all be present in the emission layer).

[0237] The first electrode may be an anode as a hole injection electrode, and the second electrode may be a cathode as an electron injection electrode; or the first electrode may be a cathode as an electron injection electrode, and the second electrode may be an anode as a hole injection electrode.

[0238] For example, in the organic light-emitting device, the first electrode is an anode, and the second electrode is a cathode, and the organic layer further includes a hole transport region arranged between the first electrode and the emission layer and an electron transport region arranged between the emission layer and the second electrode, and the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0239] The term "organic layer" as used herein refers to a single layer and / or a plurality of layers disposed between a first electrode and a second electrode of an organic light emitting device. The "organic layer" may further include an organic metal complex including a metal in addition to an organic compound.

[0240] Figure 1 FIG. 1 is a schematic diagram of an organic light emitting device 10 according to an embodiment. Figure 1The structure of an organic light emitting device according to an embodiment and a method of manufacturing the organic light emitting device according to an embodiment are described. The organic light emitting device 10 includes a first electrode 11 , an organic layer 15 , and a second electrode 19 , which are sequentially stacked.

[0241] A substrate may be additionally provided below the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate used in the field of organic light-emitting devices may be used, and the substrate may be a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, easy handling, and water resistance.

[0242] The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be a material having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-reflective electrode, or a transmissive electrode. The material for forming the first electrode may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), or zinc oxide (ZnO). In one embodiment, the material used to form the first electrode 11 may be a metal or a metal alloy, for example, magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0243] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.

[0244] The organic layer 15 is provided on the first electrode 11 .

[0245] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0246] The hole transport region may be disposed between the first electrode 11 and the emission layer.

[0247] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0248] The hole transport region may include only a hole injection layer or a hole transport layer. In one embodiment, the hole transport region may have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, which are sequentially stacked in this stated order starting from the first electrode 11.

[0249] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using a suitable method such as vacuum deposition, spin coating, casting, and / or Langmuir-Blodgett (LB) deposition.

[0250] When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a ... -8 Torr - about 10 -3 Torr vacuum pressure, and about / second - approx. However, the deposition conditions are not limited thereto.

[0251] When the hole injection layer is formed using spin coating, the coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, the coating speed may be about 2,000 rpm to about 5,000 rpm, and the temperature of heat treatment after coating to remove the solvent may be about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

[0252] By referring to the conditions for forming the hole injection layer, the conditions for forming the hole transport layer and the electron blocking layer can be understood.

[0253] The hole transport region may include, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by the following Formula 201, a compound represented by the following Formula 202, or any combination thereof:

[0254]

[0255] Formula 201

[0256]

[0257] Formula 202

[0258]

[0259] In formula 201, Ar 101and Ar 102 may be each independently unsubstituted or substituted phenylene, pentalene, indenylene, naphthylene, 1-Heptalenyl, 1-Heptalenyl, 1-Acenaphthenylidene, 1-Fluorenyl, 1-Phenanthrenyl, 1-Anthracenyl, 1-Fluoranthenyl, 1-Benzo[9,10]phenanthrenyl, 1-Pyrenyl, 1-Phenanth ... 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 2 -C 10 Heterocycloalkyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl (e.g. phenyl (C 1 -C 20 Alkyl) group), C 1 -C 60 Heteroaryl, C 2 -C 60 a heteroaralkyl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof.

[0260] In Formula 201, xa and xb may each independently be an integer of 0 to 5, or may be 0, 1, or 2. For example, xa may be 1, and xb may be 0, but embodiments of the present disclosure are not limited thereto.

[0261] In equations 201 and 202, R 101 -R 108 , R 111 -R 119 , and R 121 -R 124 Can be independently:

[0262] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), or C 1 -C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);

[0263] 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 any combination thereof; or

[0264] phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl, each 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 any combination thereof,

[0265] However, the implementation of the present disclosure is not limited thereto.

[0266] 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 any combination thereof.

[0267] In one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A, but embodiments of the present disclosure are not limited thereto:

[0268] Formula 201A

[0269]

[0270] R in Formula 201A 101, R 111 , R 112 , and R 109 The detailed description is the same as described above.

[0271] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include compounds HT1 to HT20, but are not limited thereto:

[0272]

[0273]

[0274]

[0275] The thickness of the hole transport region may be about -about For example, about -about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about -about For example, about -about In the range of, and the thickness of the hole transport layer may be about -about For example, about -about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics may be obtained without a significant increase in driving voltage.

[0276] In addition to these materials, the hole transport region may further include a charge generating material for improving conductive properties. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0277] The charge generating material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a compound containing a cyano group, or any combination thereof, but the embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are quinone derivatives such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and compounds containing a cyano group such as the following compound HT-D1, but are not limited thereto:

[0278]

[0279] The hole transport region may include a buffer layer.

[0280] Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of the formed organic light emitting device may be improved.

[0281] Meanwhile, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be the material for the hole transport region described above, the material for the host to be described later, or any combination thereof. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be mCP, which will be described later.

[0282] Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emission layer is formed by vacuum deposition or spin coating, although the deposition or coating conditions may vary depending on the compound used to form the emission layer, the deposition or coating conditions may be similar to those applied when forming the hole injection layer.

[0283] The emission layer may include a host and a dopant, and the dopant may include an organic metal compound represented by Formula 1.

[0284] The host may include TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, one of compounds H50 to H52, or any combination thereof:

[0285]

[0286] When the organic light emitting device is a full-color organic light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer. In one embodiment, due to the stacked structure including the red emission layer, the green emission layer, and / or the blue emission layer, the emission layer may emit white light.

[0287] When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.

[0288] The thickness of the emission layer may be about -about For example, about -about When the thickness of the emission layer is within this range, excellent light emitting characteristics can be obtained without a significant increase in driving voltage.

[0289] Then, an electron transport region may be disposed on the emission layer.

[0290] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0291] For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure, or an electron transport layer / electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a multilayer structure or a single layer structure including two or more different materials.

[0292] The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region may be understood by referring to the conditions for forming the hole injection layer.

[0293] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, BCP, Bphen, BAlq, or any combination thereof, but embodiments of the present disclosure are not limited thereto:

[0294]

[0295] The thickness of the hole blocking layer may be about -about For example, about -about When the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking characteristics without a significant increase in driving voltage.

[0296] The electron transport layer may include BCP, Bphen, Alq 3 , BAlq, TAZ, NTAZ, or any combination thereof:

[0297]

[0298] In one embodiment, the electron transport layer may include one of ET1 to ET25, but embodiments of the present disclosure are not limited thereto:

[0299]

[0300]

[0301] The thickness of the electron transport layer may be about -about For example, about -about When the thickness of the electron transport layer is within the above-described range, the electron transport layer may have satisfactory electron transport characteristics without a significant increase in driving voltage.

[0302] Also, the electron transport layer may further include a material including a metal in addition to the materials described above.

[0303] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (LiQ), ET-D2, or any combination thereof:

[0304]

[0305] The electron transport region may include an electron injection layer that facilitates the flow of electrons from the second electrode 19 thereinto.

[0306] The electron injection layer may include LiF, NaCl, CsF, Li 2 O, BaO, or any combination thereof.

[0307] The thickness of the electron injection layer may be about -about For example, about -about When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a significant increase in driving voltage.

[0308] The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. The material for forming the second electrode 19 may be a metal, an alloy, a conductive compound, or any combination thereof having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as a material for forming the second electrode 19. In order to manufacture a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0309] In the previous article, we have already discussed Figure 1 An organic light emitting device according to an embodiment is described.

[0310] Another aspect of the present disclosure provides a diagnostic composition comprising at least one organometallic compound represented by Formula 1.

[0311] The organometallic compound represented by Formula 1 provides high luminescence efficiency. Therefore, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.

[0312] The diagnostic compositions can be used in a variety of applications including diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0313] As used herein, the term "C 1 -C 60 "Alkyl" refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include methyl, ethyl, n-propyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, and hexyl. As used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 Alkyl is a divalent group of the same structure.

[0314] As used herein, the term "C 1 -C 60 "Alkoxy" refers to a 101 (A 101 C 1 -C 60 An alkyl group is a monovalent group represented by an alkyl group, and examples thereof include a methoxy group, an ethoxy group, and an isopropoxy group.

[0315] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having a carbon-carbon double bond in the middle or at the terminal of the alkyl group, and examples thereof include vinyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0316] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having a carbon-carbon triple bond in the middle or at the terminal of the alkyl group, and examples thereof include ethynyl, and propynyl. 2 -C 60 "Alkyne" refers to a group having a C 2 -C 60 Alkynyl is a divalent group of the same structure.

[0317] As used herein, the term "C 3 -C 10"Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. 3 -C 10 "Cycloalkylene" refers to a cycloalkylene having a 3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0318] As used herein, the term "C 2 -C 10 "Heterocycloalkyl" refers to a monovalent saturated monocyclic group having N, O, P, Si, Se, S, or a combination thereof and 2 to 10 carbon atoms as ring atoms, and non-limiting examples thereof include tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C 2 -C 10 "Heterocycloalkylene" refers to a group having a C 2 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0319] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and a carbon-carbon double bond in its ring and not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0320] As used herein, the term "C 2 -C 10 The term "heterocycloalkenyl" refers to a monovalent monocyclic group having N, O, P, Si, Se, S, or any combination thereof and 2 to 10 carbon atoms as ring atoms and a double bond in its ring. 2 -C 10 Examples of heterocycloalkenyl are 2,3-dihydrofuranyl and 2,3-dihydrothienyl. 2 -C 10 "Heterocycloalkenylene" refers to a 2 -C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0321] As used herein, the term "C 6 -C 60"Aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.

[0322] As used herein, the term "C 7 -C 60 "Arylalkyl" refers to a C 6 -C 59 Aryl substituted C 1 -C 54 Alkylene. C 7 -C 60 Non-limiting examples of aralkyl groups include -CH 2 -phenyl (i.e., benzyl) groups and -CH 2 -naphthyl.

[0323] As used herein, the term "phenyl (C 1 -C 20 "alkyl) group" refers to a C 1 -C 20 Alkylene. Phenyl (C 1 -C 20 Non-limiting examples of alkyl) groups include -CH 2 -phenyl (i.e., benzyl) groups and -(CH 2 ) 3 -phenyl.

[0324] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having N, O, P, Si, Se, S, or a combination thereof and 1 to 60 carbon atoms as ring atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic system having N, O, P, Si, Se, S, or any combination thereof and 1 to 60 carbon atoms as ring atoms. 1 -C 60Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.

[0325] As used herein, the term "C 2 -C 60 "Heteroaralkyl" refers to a C 1 -C 59 Heteroaryl-substituted C 1 -C 59 Alkylene. C 2 -C 60 Non-limiting examples of heteroarylalkyl groups include -CH 2 -pyridyl.

[0326] As used herein, the term "C 6 -C 60 "Aryloxy" means -OA 102 (A 102 C 6 -C 60 aryl), and as used herein, the term "C 6 -C 60 "Arylthio" means -SA 103 (A 103 C 6 -C 60 aryl).

[0327] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8-60 carbon atoms) having two or more rings fused to each other, having only carbon atoms as ring-forming atoms, and not having aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic fused polycyclic group include fluorenyl. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.

[0328] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 2-60 carbon atoms) having two or more rings fused to each other, having heteroatoms selected from N, O, P, Si, and S as ring-forming atoms in addition to carbon atoms, and having no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic group include carbazolyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.

[0329] As used herein, the term "C 5 -C 30 The term "carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring atoms. 5 -C 30 The carbocyclic group may be a monocyclic group or a polycyclic group.

[0330] As used herein, the term "C 2 -C 30 The term "heterocyclic group" refers to a saturated or unsaturated cyclic group having N, O, Si, P, Se, S, or any combination thereof and 1 to 30 carbon atoms as ring atoms. 2 -C 3 The heterocyclic group may be a monocyclic group or a polycyclic group.

[0331] 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 3 -C 10 Cycloalkyl, substituted C 2 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 2 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C60 Arylthio, substituted C 7 -C 60 Arylalkyl (e.g. substituted phenyl (C 1 -C 20 alkyl) group), substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 The substituents of the heteroaralkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

[0332] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy;

[0333] 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, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 2 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl (e.g. phenyl (C 1 -C 20 Alkyl) group), C 1 -C 60 Heteroaryl, C 2 -C 60 heteroarylalkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 ), or any combination thereof;

[0334] C 3 -C 10 Cycloalkyl, C 2 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Arylalkyl (e.g. phenyl (C 1 -C 20 Alkyl) group), C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 a heteroaralkyl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group;

[0335] Each of C is substituted by 3 -C 10 Cycloalkyl, C 2 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2-C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl (e.g. phenyl (C 1 -C 20 Alkyl) group), C 1 -C 60 Heteroaryl, C 2 -C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 2 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Arylalkyl (e.g. phenyl (C 1 -C 20 Alkyl) group), C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 heteroarylalkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 ), or any combination thereof;

[0336] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 ), or -P(=O)(Q 38 )(Q 39 );or

[0337] Any combination thereof.

[0338] In this manual, Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 may be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, 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 2 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Alkyl, C 6 -C 60 Aryl, or any combination thereof substituted C 6 -C 60 Aryl, C6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl (e.g. phenyl (C 1 -C 20 Alkyl) group), C 1 -C 60 Heteroaryl, C 2 -C 60 heteroaralkyl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof.

[0339] Hereinafter, the compound and the organic light-emitting device according to the embodiment are described in detail with reference to the synthesis examples and the examples. However, the organic light-emitting device is not limited thereto. The phrase "using B instead of A" used in describing the synthesis examples means that the amount of B used is the same as the amount of A used in terms of molar equivalents.

[0340] Example

[0341] Synthesis Example 1 (Compound 1)

[0342]

[0343] Synthesis of intermediate L1

[0344] 6-Chloro-2-phenylfuro[2,3-b]pyridine (2.55 g, 11.1 mmol), phenylboronic acid (2.603 g, 16.64 mmol), Pd(PPh 3 ) 4 (1.03 g, 0.89 mmol), and K 2 CO 3 (3.83 g, 27.7 mmol) was mixed with 60 mL of tetrahydrofuran and 30 mL of distilled water, stirred at 90° C. for 18 hours, and then cooled to room temperature. An organic layer was extracted from the resultant obtained therefrom using ethyl acetate, and the organic layer was washed with anhydrous magnesium sulfate (MgSO 4 ) was dried, and filtered to obtain a filtrate. The filtrate was concentrated to obtain a residue. The residue was purified by column chromatography using ethyl acetate:hexane=1:2 (v / v) as an eluent to obtain intermediate L1 (2.85 g, 83%).

[0345] LC-MS m / z=272(M+H) + .

[0346] Synthesis of intermediate L1-dimer

[0347] Intermediate L1 (1.99g, 7.32mmol) and iridium chloride hydrate (1.15g, 3.25mmol) are mixed with 21mL 2-ethoxyethanol and 7mL distilled water, stirred at 120 ℃ temperature for 24 hours under reflux, then cooled to room temperature.The solid obtained by it is filtered, separated, and fully washed with the order of water / methanol / hexane.Solid is dried in a vacuum oven to obtain intermediate L1-dimer (1.95g, 78%).The compound obtained is used in the next reaction without additional purification.

[0348] Synthesis of compound 1

[0349] 30 mL of 2-ethoxyethanol was added to the intermediate L1-dimer (1.94 g, 1.26 mmol), acetylacetone (1.26 g, 12.6 mmol), and Na 2 CO 3 (1.33 g, 12.6 mmol), and stirred at room temperature for 12 hours. An organic layer was extracted from the resultant obtained therefrom using ethyl acetate, and the organic layer was washed with anhydrous magnesium sulfate (MgSO 4 ) was dried and filtered to obtain a filtrate. The filtrate was concentrated to obtain a residue. The residue was purified by column chromatography using dichloromethane: hexane = 1: 4 (volume / volume) as an eluent to obtain compound 1 (0.451 g, 22%). The obtained compound was confirmed by mass spectrometry (MS) and HPLC analysis.

[0350] HRMS (MALDI-TOF): For C 43 H 31 Ir 2 O 4 Calculated value: m / z 832.1913, found value: 832.1913.

[0351] Synthesis Example 2 (Compound 16)

[0352]

[0353] Synthesis of intermediate L16

[0354] 6-Chloro-2-phenylfuro[2,3-b]pyridine (2.69 g, 11.71 mmol), (3,5-dimethylphenyl)boronic acid (2.64 g, 17.56 mmol), Pd(PPh 3 ) 4 (1.08 g, 0.94 mmol), and K 2 CO 3(4.05 g, 29.3 mmol) was mixed with 60 mL of tetrahydrofuran and 30 mL of distilled water, stirred at 90° C. for 18 hours, and then cooled to room temperature. An organic layer was extracted from the resultant obtained therefrom using ethyl acetate, and the organic layer was washed with anhydrous magnesium sulfate (MgSO 4 ) was dried and filtered to obtain a filtrate. The filtrate was concentrated to obtain a residue. The residue was purified by column chromatography using ethyl acetate:hexane=1:2 (v / v) as an eluent to obtain intermediate L16 (1.97 g, 56%).

[0355] LC-MS m / z=300(M+H) + .

[0356] Synthesis of intermediate L16-dimer

[0357] Intermediate L16 (1.97g, 6.82mmol) and iridium chloride hydrate (1.07g, 3.03mmol) are mixed with 21mL ethoxyethanol and 7mL distilled water, stirred at 120 ℃ temperature for 24 hours under reflux, then cooled to room temperature.The solid obtained by it is filtered, separated, and fully washed with the order of water / methanol / hexane.Solid is dried in a vacuum oven to obtain intermediate L16-dimer (2.16g, 86%).The compound obtained is used in the next reaction without additional purification.

[0358] Synthesis of compound 16

[0359] 30 mL of 2-ethoxyethanol was added to the intermediate L16-dimer (2.15 g, 1.31 mmol), acetylacetone (1.31 g, 13.1 mmol), and Na 2 CO 3 (1.38 g, 13.1 mmol), and stirred at room temperature for 12 hours. An organic layer was extracted from the resultant obtained therefrom using ethyl acetate, and the organic layer was washed with anhydrous magnesium sulfate (MgSO 4 ) was dried and filtered to obtain a filtrate. The filtrate was concentrated to obtain a residue. The residue was purified by column chromatography using dichloromethane: hexane = 1: 4 as an eluent to obtain compound 16 (0.47 g, 20%). The obtained compound was confirmed by MS and HPLC analysis.

[0360] HRMS (MALDI-TOF): For C 47 H 39 Ir 2 O 4 Calculated value: m / z 888.2539, found: 888.2538.

[0361] Synthesis Example 3 (Compound 101)

[0362]

[0363] Synthesis of intermediate L101

[0364] Intermediate L101 (2.08 g, 59%) was obtained in the same manner as in the synthesis of intermediate L1 of Synthesis Example 1, except that 6-chloro-2-phenylthieno[2,3-b]pyridine (2.99 g, 12.2 mmol) was used instead of 6-chloro-2-phenylfurano[2,3-b]pyridine (2.55 g, 11.1 mmol).

[0365] LC-MS m / z=288(M+H) + .

[0366] Synthesis of intermediate L101-dimer

[0367] Intermediate L101-dimer (2.16 g, 86%) was obtained in the same manner as in the synthesis of Intermediate L1-dimer of Synthesis Example 1, except that Intermediate L101 (1.97 g, 7.03 mmol) was used instead of Intermediate L1.

[0368] Synthesis of compound 101

[0369] Compound 101 (0.47 g, 22%) was obtained in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate L101-Dimer (1.95 g, 1.22 mmol) was used instead of Intermediate L1-Dimer. The obtained compound was confirmed by MS and HPLC analysis.

[0370] HRMS (MALDI-TOF): For C 43 H 30 Ir 2 O 2 S 2 Calculated for m / z 863.1378, found 863.1377.

[0371] Synthesis Example 4 (Compound 116)

[0372]

[0373] Synthesis of intermediate L116

[0374] Intermediate L116 (3.00 g, 86%) was obtained in the same manner as in the synthesis of intermediate L16 of Synthesis Example 2, except that 6-chloro-2-phenylthieno[2,3-b]pyridine (2.73 g, 11.1 mmol) was used instead of 6-chloro-2-phenylfurano[2,3-b]pyridine (2.69 g, 11.71 mmol).

[0375] LC-MS m / z=316(M+H) + .

[0376] Synthesis of intermediate L116-dimer

[0377] Intermediate L116-dimer (2.16 g, 72%) was obtained in the same manner as in the synthesis of intermediate L16-dimer of Synthesis Example 2, except that intermediate L116 (2.48 g, 7.88 mmol) was used instead of intermediate L16.

[0378] Synthesis of compound 116

[0379] Compound 116 (0.47 g, 21%) was obtained in the same manner as in the synthesis of Compound 16 of Synthesis Example 2, except that Intermediate L116-Dimer (2.04 g, 1.19 mmol) was used instead of Intermediate L16-Dimer. The obtained compound was confirmed by MS and HPLC analysis.

[0380] HRMS (MALDI-TOF): For C 47 H 39 Ir 2 O 2 S 2 Calculated for m / z 920.2082, found 920.2080.

[0381] Synthesis Example 5 (Compound 146)

[0382]

[0383] Synthesis of intermediate L146

[0384] Intermediate L146 (3.30 g, 83%) was obtained in the same manner as in the synthesis of intermediate L116 of Synthesis Example 4, except that (3-(tert-butyl)-5-methylphenyl)boric acid (3.23 g, 16.8 mmol) was used instead of (3,5-dimethylphenyl)boric acid (2.64 g, 17.56 mmol).

[0385] LC-MS m / z=358(M+H) + .

[0386] Synthesis of intermediate L146-dimer

[0387] Intermediate L146-dimer (2.60 g, 74%) was obtained in the same manner as in the synthesis of intermediate L116-dimer of Synthesis Example 4, except that intermediate L146 (2.99 g, 8.37 mmol) was used instead of intermediate L116.

[0388] Synthesis of compound 146

[0389] Compound 146 (0.48 g, 20%) was obtained in the same manner as in the synthesis of Compound 116 of Synthesis Example 4, except that Intermediate L146-Dimer (2.04 g, 1.19 mmol) was used instead of Intermediate L116-Dimer. The obtained compound was confirmed by MS and HPLC analysis.

[0390] HRMS (MALDI-TOF): For C 47 H 38 Ir 2 O 2 S 2 Calculated for m / z 919.2004, found 919.2003.

[0391] Synthesis Example 6 (Compound 216)

[0392]

[0393] Synthesis of intermediate L216

[0394] Intermediate L216 (3.00 g, 86%) was obtained in the same manner as in the synthesis of intermediate L16 of Synthesis Example 2, except that 5-chloro-2-phenylfuro[3,2-b]pyridine (2.69 g, 11.71 mmol) was used instead of 6-chloro-2-phenylfuro[2,3-b]pyridine (2.69 g, 11.71 mmol).

[0395] LC-MS m / z=300(M+H) + .

[0396] Synthesis of intermediate L216-dimer

[0397] Intermediate L216-dimer (3.2 g, 91%) was obtained in the same manner as in the synthesis of intermediate L16-dimer of Synthesis Example 2, except that intermediate L216 (2.86 g, 9.55 mmol) was used instead of intermediate L16. The obtained compound was used in the next reaction without additional purification.

[0398] Synthesis of compound 216

[0399] Compound 216 (0.75 g, 34%) was obtained in the same manner as in the synthesis of Compound 16 of Synthesis Example 2, except that Intermediate L216-Dimer (2.04 g, 1.24 mmol) was used instead of Intermediate L16-Dimer. The obtained compound was confirmed by MS and HPLC analysis.

[0400] HRMS (MALDI-TOF): For C 47 H 39 Ir 2 O 4 Calculated for m / z 888.2539, found: 888.2539.

[0401] Synthesis Example 7 (Compound 316)

[0402]

[0403] Synthesis of intermediate L316

[0404] Intermediate L316 (3.01 g, 76%) was obtained in the same manner as in the synthesis of intermediate L16 of Synthesis Example 2, except that 5-chloro-2-phenylthieno[3,2-b]pyridine (3.12 g, 12.7 mmol) was used instead of 5-chloro-2-phenylfurano[2,3-c]pyridine (2.69 g, 11.71 mmol).

[0405] LC-MS m / z=316(M+H) + .

[0406] Synthesis of intermediate L316-dimer

[0407] Intermediate L316-dimer (2.60 g, 74%) was obtained in the same manner as in the synthesis of Intermediate L16-dimer of Synthesis Example 2, except that Intermediate L316 (2.89 g, 9.19 mmol) was used instead of Intermediate L16.

[0408] Synthesis of compound 316

[0409] Compound 316 (0.49 g, 20%) was obtained in the same manner as in the synthesis of Compound 16 of Synthesis Example 2, except that Intermediate L316-Dimer (2.23 g, 1.30 mmol) was used instead of Intermediate L16-Dimer. The obtained compound was confirmed by MS and HPLC analysis.

[0410] HRMS (MALDI-TOF): For C47 H 39 Ir 2 O 2 S 2 Calculated for m / z 920.2082, found 920.2080.

[0411] Evaluation Example 1: Evaluation of Radiation Attenuation Rate

[0412] CBP and compound 16 were mixed at a weight ratio of 9:1 in 10 -7 The films were co-deposited under a vacuum pressure of 2000 torr to produce a film having a thickness of 40 nm.

[0413] The PL spectrum of the film was evaluated at room temperature by using a PicoQuant TRPL measurement system FluoTime 300 and a PicoQuant pump light source PLS340 (excitation wavelength = 340 nm, spectrum width = 20 nm), the wavelength of the main peak of the spectrum was determined, and PLS340 repeatedly measured the number of photons emitted from the film at the wavelength of the main peak due to a photon pulse (pulse width = 500 ps) applied to the film over time based on time-correlated single photon counting (TCSPC), thereby obtaining a fully fittable TRPL curve. The decay time T of the film was obtained by fitting one or more exponential decay functions to the results obtained therefrom. 衰减 The function for fitting is represented by Equation 10, and the maximum value among the values ​​obtained by each exponential decay function for fitting is taken as T 衰减 At this time, a baseline or background signal curve is obtained by repeating the same measurement again in a dark state (a state in which a pump signal applied to a predetermined film is blocked) for the same measurement time as that used to obtain the TRPL curve, and fitting is performed using the baseline or background signal curve as a baseline.

[0414] Equation 10

[0415]

[0416] Then, the quantum efficiency of the film was measured by using a Hamamatsu Quantaurus-QY absolute PL quantum yield spectrometer (equipped with a xenon lamp light source, a monochromator, a photon multichannel analyzer, and an integrating sphere and using PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). When measuring the quantum efficiency, the excitation wavelength was measured while scanning at intervals of 10 nm from 320 nm to 380 nm, and the maximum value was taken as the quantum efficiency (Φ).

[0417] By adding T 衰减Substituting Φ into Equation 11, the radiation decay rate (k r ), and the results are shown in Table 2.

[0418] Equation 11

[0419] k r =Φ / T 衰减 .

[0420] The measurement of the radiation decay rate was repeated for compounds 101, 116, 146, 216, 316, A1, A2, B, C1, C2 and D, and the results are shown in Table 2.

[0421] Table 2

[0422] Compound No. <![CDATA[Radiation attenuation rate (s -1 )]]> 16 <![CDATA[4.72×10 5 ]]> 101 <![CDATA[5.68×10 5 ]]> 116 <![CDATA[7.09×10 5 ]]> 146 <![CDATA[6.72×10 5 ]]> 216 <![CDATA[1.22×10 6 ]]> 316 <![CDATA[1.56×10 6 ]]> A1 <![CDATA[4.08×10 5 ]]> A2 <![CDATA[4.15×10 5 ]]> B <![CDATA[4.62×10 5 ]]> C1 <![CDATA[1.85×10 5 ]]> C2 <![CDATA[3.52×10 5 ]]> D <![CDATA[2.13×10 5 ]]>

[0423]

[0424] From Table 2, it was confirmed that Compounds 16, 101, 116, 146, 216, and 316 had high radiation decay rates compared to those of Compounds A1, A2, B, C1, C2, and D.

[0425] Example 1

[0426] ITO / Ag / ITO is deposited on it. The glass substrate as an anode was cut into a size of 50 mm×50 mm×0.5 mm, ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the glass substrate was provided to a vacuum deposition apparatus.

[0427] 2-TNATA is vacuum deposited on the anode to form a A hole injection layer having a thickness of 1000 Å was formed, and 4,4′-di[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum-deposited on the hole injection layer to form a The hole transport layer has a thickness of .

[0428] Then, CBP (host) and compound 16 (dopant) were co-deposited on the hole transport layer at a weight ratio of 98:2 to form a The thickness of the emission layer.

[0429] Then, BCP is vacuum deposited on the emission layer to form a The thickness of the hole blocking layer is Alq 3 Vacuum deposition is performed on the hole blocking layer to form a An electron transport layer having a thickness of , LiF is vacuum deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Mg and Ag are co-deposited on the electron injection layer at a weight ratio of 90:10 to form a A cathode with a thickness of is formed, thereby completing the manufacture of an organic light-emitting device (which emits red light).

[0430]

[0431] Examples 2-6 and Comparative Examples A1, A2, B, C1, C2, and D

[0432] An organic light-emitting device was manufactured in the same manner as in Example 1, except that in forming the emission layer, the compounds shown in Table 3 were each used as a dopant instead of Compound 16.

[0433] Evaluation Example 2: Evaluation of Characteristics of Organic Light-Emitting Device

[0434] The driving voltage, maximum value of external quantum efficiency (Max EQE), roll-off ratio, maximum emission wavelength of the main peak of EL spectrum, and lifetime (T 97 ), and the results are shown in Table 3. A current-voltage meter (Keithley 2400) and a brightness meter (MinoltCs-1000A) were used as measurement equipment, and the lifespan (T 97 ) (at 3,500 nits) represents the amount of time that has elapsed when the brightness is 97% of the initial brightness (100%).

[0435] The roll-off ratio is calculated using Equation 20:

[0436] Equation 20

[0437] Roll-off ratio = {1-(efficiency (at 3,500 nits) / maximum luminous efficiency)}×100%

[0438] Table 3

[0439]

[0440]

[0441]

[0442] From Table 3, it is confirmed that the organic light-emitting devices of Examples 1-6 emit red light and have improved driving voltage, improved external quantum efficiency, improved roll-off ratio, and improved lifespan characteristics compared to those of the organic light-emitting devices of Comparative Examples A1, A2, B, C1, C2, and D.

[0443] Since the organometallic compound has a high radiation decay rate, an electronic device such as an organic light-emitting device including the organometallic compound represented by Formula 1 may have improved driving voltage, improved external quantum luminescence efficiency, improved roll-off ratio, and improved lifespan characteristics. In addition, since the organometallic compound has excellent phosphorescent luminescence characteristics, a diagnostic composition with high diagnostic efficiency can be provided by using the organometallic compound.

[0444] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects in each embodiment should typically be considered as available for other similar features or aspects in other embodiments.

[0445] Although embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.

Claims

1. An organometallic compound represented by formula 1: Formula 1 M(L1) n1 (L2) n2 , in, In formula 1, M is Ir, L1 is a ligand represented by formula 2, n1 is 1 or 2, wherein when n1 is 2, the two L1s are the same as or different from each other, L2 is a group represented by formula 3-1 (301), n2 is 1 or 2, wherein when n2 is 2, the two L2 are the same as or different from each other, and The sum of n1 and n2 is 3: Among them, in formula 2, X1 is C, X 21 For C, One of X2 and X3 is C(R2), and the other is O or S, X4 is C(R4), X5 is C(R5), R1, R2, R4, R5, and R 21 Each independently is: Hydrogen, Deuterium, C1-C 20 Alkyl, or C1-C 20 alkoxy; or C1-C 20 Alkyl or C1-C 20 Alkoxy: deuterium, -CD3, -CD2H, -CDH2, C1-C 10 Alkyl, or any combination thereof, Ring CY1 and R2 are not connected to each other, and R1 and R2 are not connected to each other, By *-(L 11 ) b11 The group represented by -*' is a single bond, * and *' in Formula 2 each represent a binding site with M in Formula 1, In formula 2, The group represented is a phenyl group which is unsubstituted or substituted by a1 number of R1, where a1 is an integer of 0-5, In formula 2, The group represented is a group represented by the formula CY21-1: Among them, in formula CY21-1, X 21 and R 21 Same as described above, a24 is an integer from 0 to 4. *" represents the binding site with the carbon atom of the adjacent 6-membered ring in Formula 2, and * represents the binding site with M in Formula 1, Among them, in formula 3-1 (301), Z 12 is hydrogen or deuterium, Z 11 and Z 13 Each independently and with respect to R 21 The same as defined, and * and *' each represent a binding site to M in Formula 1.

2. The organometallic compound according to claim 1, wherein R1 and R2 are each independently: hydrogen or deuterium; or each unsubstituted or substituted by methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 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 C1-C2-6 10 Alkoxy: deuterium, -CD3, -CD2H, -CDH2, C1-C 10 alkyl, or any combination thereof.

3. The organometallic compound according to claim 1, wherein Depend on The group represented is a group represented by one of formulas 10-13(1) to 10-13(18) or 10-13: in, In Formulas 10-13(1) to 10-13(18) and 10-13, R 1a -R 1e Each independently is the same as defined in claim 1 with respect to R1, wherein R 1a -R 1e Each is not hydrogen, and * indicates a bonding site with an adjacent atom.

4. The organometallic compound according to claim 1, wherein In formula 2, The group represented is a group represented by one of the formulae CY21(1) to CY21(16): in, In formulas CY21(1) to CY21(16), X 21 and R 21 Each independently the same as described in claim 1, R 21a -R 21d Each independently of the above in claim 1 with respect to R 21 The same as defined above, where R 21 and R 21a -R 21d Each is not hydrogen, *" represents the binding site with the carbon atom of the adjacent 6-membered ring in Formula 2, and * indicates the binding site with M in Formula 1.

5. The organometallic compound according to claim 1, wherein L1 is a ligand represented by Formula 2A: in, In Formula 2A, X1, X 21 , CY1, CY 21 , X4, X5, R1, R2, R 21 、a1、a21、L 11 , b11, *, and *' are each independently the same as described in claim 1, wherein X2 is O or S.

6. The organometallic compound according to claim 1, wherein L1 is a ligand represented by Formula 2B: in, In Formula 2B, X1, X 21 , CY1, CY 21 , X4, X5, R1, R2, R 21 、a1、a21、L 11 , b11, *, and *' are each independently the same as described in claim 1, wherein X3 is O or S.

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

8. 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 7.

9. The organic light emitting device according to claim 8, wherein The first electrode is an anode, The second electrode is a cathode, The organic layer further includes a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

10. The organic light emitting device according to claim 8, wherein The emission layer includes the organic metal compound.

11. The organic light emitting device according to claim 10, wherein The emission layer further includes a host, and an amount of the host is greater than an amount of the organic metal compound.

Images