Organometallic compounds, organic light-emitting devices including the same, and diagnostic compositions including the same.

Abstract

This invention relates to organometallic compounds, organic light-emitting devices including the same, and diagnostic compositions including the same. The organometallic compounds are represented by Formula 1, wherein, in Formulas 1, 1A, and 1B, M1 is a transition metal, Ln1 is a ligand represented by Formula 1A, Ln2 is a ligand represented by Formula 1B, n1 is 0, 1, or 2, n2 is 1, 2, or 3, a1 is 0, 1, 2, or 3, k1 is 1, 2, 3, 4, 5, 6, 7, or 8, and b10 and b20 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and... ＊ and ＊ Each of these represents a binding site with M1, and CY1, CY2, X1, X2, Y1-Y1 represent the binding sites with M1. 10 L1, Ar1, R1, R2, R 10 and R 20 As provided in this article. Equation 1M1(Ln1) n1 (Ln2) n2 Formula 1A Formula 1B

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefits, and all benefits arising therefrom, to Korean Patent Application No. 10-2020-0141568, filed on October 28, 2020, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This disclosure relates to organometallic compounds, organic light-emitting devices including said organometallic compounds, and diagnostic compositions including said organometallic compounds. Background Technology

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

[0005] An OLED comprises an anode, a cathode, and an organic layer located between the anode and cathode, including an emitter layer. Hole transport regions may be located between the anode and the emitter layer, and electron transport regions may be located between the emitter layer and the cathode. Holes supplied from the anode can move towards the emitter layer through the hole transport regions, and electrons supplied from the cathode can move towards the emitter layer through the electron transport regions. Holes and electrons recombine in the emitter layer to generate excitons. These excitons transition from an excited state to the ground state, thereby producing light. Summary of the Invention

[0006] Provided are organometallic compounds, organic light-emitting devices comprising at least one of the organometallic compounds, and diagnostic compositions comprising at least one of the organometallic compounds.

[0007] Other 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 embodiments of this disclosure presented.

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

[0009] Formula 1

[0010] M1(Ln1) n1 (Ln2) n2

[0011] In Equation 1,

[0012] M1 is a transition metal.

[0013] Ln1 is the ligand represented by Equation 1A.

[0014] Ln2 is the ligand represented by Equation 1B.

[0015] n1 is 0, 1, or 2.

[0016] n2 is 1, 2, or 3.

[0017] Formula 1A

[0018]

[0019] Formula 1B

[0020]

[0021] Among them, in equations 1A and 1B,

[0022] X1 is C or N, and X2 is C or N.

[0023] Y1 is C(R) 41 ) or N, Y2 is C(R) 42 ) or N, Y3 is C(R 43 ) or N, Y4 is C(R 44 ) or N, Y5 is C(R) 45 ) or N, Y6 is C(R 46 ) or N, Y7 is C(R 47 ) or N, Y8 is C(R 48 ) or N, Y9 is C(R 49 ) or N, and Y 10 For C(R) 50 ) or N,

[0024] CY1 and CY2 are independently C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups,

[0025] L1 represents substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, or substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0026] a1 is 0, 1, 2, or 3.

[0027] Ar1, R1, R2, R 10 R 20 and R41 -R 50 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q3)(Q1)(Q2), -Ge(Q3)(Q4)(Q5), -N(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9),

[0028] Multiple R 10 At least two of them may be combined to form substituted or unsubstituted C5-C 30 The carbocyclic group may or may not be substituted C1-C 30 Heterocyclic groups,

[0029] Multiple R 20 At least two of them may be combined to form substituted or unsubstituted C5-C 30 The carbocyclic group may or may not be substituted C1-C 30 Heterocyclic groups,

[0030] Ar1, R1, R2, R 10 R20 and R 41 -R 50 At least two adjacent groups may optionally combine to form a substituted or unsubstituted C5-C 30 The carbocyclic group may or may not be substituted C1-C 30 Heterocyclic groups,

[0031] k1 is 1, 2, 3, 4, 5, 6, 7, or 8.

[0032] b10 and b20 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and

[0033] Replacement C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Heteroaryl groups, substituted divalent nonaromatic fused polycyclic groups, substituted divalent nonaromatic fused heterocyclic groups, substituted C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 heteroaryl thiols, substituted C2-C 60 Heteroarylalkyl, substituted C2-C 60 At least one substituent of the alkyl heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group is:

[0034] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy;

[0035] Each of the C1-Cs is replaced by at least one of the following: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroarylalkyl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 ), or -P(=O)(Q 18 (Q) 19 );

[0036] C3-C 10 cycloalkyl, C1-C 10Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroarylalkyl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heterocyclic group;

[0037] Each of the C3-C molecules is replaced by at least one of the following: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroarylalkyl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60heteroaryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroarylalkyl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 ), or -P(=O)(Q 28 (Q) 29 );or

[0038] -Si(Q 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 ), or -P(=O)(Q 38 (Q) 39 ),

[0039] Among them, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic group, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic group.

[0040] According to another aspect of one or more embodiments, an organic light-emitting device includes: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, wherein the organic layer includes an emitting layer and at least one of the organometallic compounds.

[0041] The organometallic compound may be included in the emission layer of the organic layer, and the organometallic compound included in the emission layer may act as a dopant.

[0042] According to another aspect of the embodiment, the diagnostic composition may include at least one organometallic compound represented by Formula 1. Attached Figure Description

[0043] The above and other aspects, features, and advantages of some embodiments of this disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, wherein

[0044] Figure 1 A schematic cross-sectional view is provided to show one aspect of an organic light-emitting device according to one or more embodiments. Detailed Implementation

[0045] Exemplary embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals always refer to the same elements. In this respect, the exemplary embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, exemplary embodiments are described below with reference to the accompanying drawings to illustrate aspects. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. Expressions such as “at least one of” modify the entire list of elements when preceding or following it, without modifying any individual element of the list.

[0046] The terminology used herein is for the purpose of describing one or more exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms “a” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. The term “or” means “and / or”. It will be further understood that the terms “comprising” or “including” as used in this specification indicate the presence of the stated features, regions, integrals, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more additional features, regions, integrals, steps, operations, elements, components, and / or sets thereof.

[0047] It will be understood that although the terms first, second, third, etc., may be used herein to describe various elements, components, regions, layers, and / or portions, these elements, components, regions, layers, and / or portions should not be limited by these terms. These terms are used only to distinguish one element, component, region, layer, or portion from another. Therefore, without departing from the teachings of this embodiment, the first element, component, region, layer, or portion discussed below may be referred to as the second element, component, region, layer, or portion.

[0048] Exemplary embodiments are described herein with reference to cross-sectional views that serve as schematic representations of idealized embodiments. Thus, deviations from the shapes depicted in the figures will be anticipated as a result of, for example, manufacturing techniques and / or tolerances. Therefore, the embodiments described herein should not be construed as limited to the specific shapes of the regions illustrated herein, but rather include deviations in shape caused, for example, by manufacturing processes. For example, regions illustrated or described as flat may typically have rough and / or non-linear characteristics. Furthermore, sharp corners in the figures may be rounded. Therefore, the regions illustrated in the figures are schematic in nature, and their shapes are not intended to illustrate the precise shapes of the regions nor to limit the scope of the claims.

[0049] It will be understood that when an element is referred to as being "on" another element, it may be in direct contact with said other element or there may be an intermediate element between them. Conversely, when an element is referred to as being "directly on" another element, there is no intermediate element.

[0050] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in common dictionaries, should be interpreted as having meanings consistent with their context in the relevant field and in the present disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly defined herein.

[0051] As used herein, “about” or “approximately” includes the stated value and means within an acceptable range of deviations from the specific value, as determined by a person skilled in the art taking into account the measurement in question and the errors associated with the measurement of the specific quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations relative to the stated value, or within ±30%, 20%, 10%, or 5%.

[0052] Organometallic compounds can be represented by Formula 1:

[0053] Formula 1

[0054] M1(Ln1) n1 (Ln2) n2

[0055] In Equation 1, M1 is a transition metal.

[0056] In one or more embodiments, M1 may be a first row of transition metals, a second row of transition metals, or a third row of transition metals.

[0057] In one or more embodiments, M1 may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0058] In one or more embodiments, M1 may be Ir, Pt, Os, or Rh.

[0059] In one or more embodiments, M1 may be Ir.

[0060] In Equation 1, n1 is 1 or 2, and n2 is 1, 2, or 3.

[0061] In one or more implementations, n1+n2 can be 2 or 3.

[0062] In one or more embodiments, M1 can be Ir, and n1+n2 can be 3.

[0063] In one or more embodiments, M1 can be Pt, and n1+n2 can be 2.

[0064] In Equation 1, Ln1 is the ligand represented by Equation 1A:

[0065] Formula 1A

[0066]

[0067] In Equation 1, Ln2 is the ligand represented by Equation 1B:

[0068] Formula 1B

[0069]

[0070] In Equation 1A, X1 is C or N, and X2 is C or N.

[0071] In Equation 1B, Y1 is C(R) 41 ) or N, Y2 is C(R) 42 ) or N, Y3 is C(R 43 ) or N, Y4 is C(R 44 ) or N, Y5 is C(R) 45 ) or N, Y6 is C(R 46 ) or N, Y7 is C(R 47 ) or N, Y8 is C(R 48 ) or N, Y9 is C(R 49 ) or N, and Y 10 For C(R) 50 ) or N.

[0072] In Equation 1A, CY1 and CY2 are each independently C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups.

[0073] In one or more embodiments, CY1 and CY2 may each independently be i) a first ring, ii) a second ring, iii) a fused ring in which at least two first rings are fused, iv) a fused ring in which at least two second rings are fused, or v) a fused ring in which at least one first ring is fused with at least one second ring.

[0074] The first ring may be a cyclopentyl group, a cyclopentadienyl group, a furan group, a thiophene group, a pyrrole group, a thiophene group, an indole group, a benzofuran group, a benzothiophene group, an indole group, or a benzothiophene group. azole group, iso- azole group, diazole group, isodiazole group diazole group, Triazole group, iso Triazole group, thiazole group, isothiazole group, thiadiazole group, isothiazole group, thiatriazole group, isothiazole group, pyrazole group, imidazole group, triazole group, tetraazole group, azathiophene group, diazathiophene group, or triazathiophene group, and

[0075] The second ring may be an adamantyl group, a norbornel group, a cyclohexyl group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0076] In one or more embodiments, CY1 and CY2 may each independently be a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a phenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, etc. Groups, cyclopentadienyl groups, 1,2,3,4-tetrahydronaphthalene groups, thiophene groups, furan groups, indole groups, benzoborane heterocyclopentadienyl groups, benzophosphane heterocyclopentadienyl groups, indene groups, benzothiophene groups, benzogermanium heterocyclopentadienyl groups, benzothiophene groups, benzoselenene groups, benzofuran groups, carbazole groups, dibenzoborane heterocyclopentadienyl groups, dibenzophosphane heterocyclopentadienyl groups, fluorene groups, dibenzothiophene groups, dibenzogermanium heterocyclopentadienyl groups, dibenzothiophene groups, dibenzoselenene groups, dibenzofuran groups, dibenzothiophene 5-oxide groups, 9H-fluorene-9-one groups, dibenzothiophene 5,5-dioxide groups, azidoindole groups, azidobenzoborane heterocyclopentadienyl groups, azidobenzophosphane heterocyclopentadienyl groups, azidoindene groups, azidoindene groups, azidoindole groups Benzothiophene group, azabenzogermanium heterocyclopentadiene group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoboron heterocyclopentadiene group, azadibenzophosphaceropentadiene group, azafluorene group, azadibenzothiophene group, azadibenzogermanium heterocyclopentadiene 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, phenanthrene-rhein group, pyrrole group, pyrazole group, imidazole group, triazole group azole group, iso- azole group, thiazole group, isothiazole group, Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo[] azole group, benzothiazole group, benzo[] The diazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, or 5,6,7,8-tetrahydroquinoline group.

[0077] In one or more embodiments, CY1 and CY2 may each independently be a phenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthrene group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene group, an azirfluorene group, an azircarbazole group, an azirdibenzofuran group, an azirdibenzothiophene group, or an azirdibenzothiophene group.

[0078] In one or more embodiments, CY1 may be a pyridine group, pyrimidine group, pyrazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, or quinazoline group.

[0079] In one or more embodiments, CY2 may be a phenyl group, naphthyl group, pyridine group, pyrimidine group, pyrazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazolinine group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, or dibenzothiophene group.

[0080] In Equation 1B, L1 can be substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hypoaryl, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, or substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0081] In one or more embodiments, L1 may be cyclopentylene, cyclohexylene, phenylene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluoranthylene, benzo[9,10]phenanthrene, pyrene, etc. Perylene, thiophene, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, pyrazolyl, thiazolyl, isothiazolyl, etc. azole group, isopropyl alcohol azole group, thiamethoxamyl group, thiamethoxamyl group Diazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolineyl, isoquinolineyl, benzoquinolineyl, phthalazinyl, naphthidyl, quinoxalinyl, quinoxalinyl, phenanthrene-pyridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl azole group, isobenzoxyl Azolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, or zazacarbazoyl; or

[0082] Each of the following is substituted with at least one of the following: phenylene, naphthylene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[9,10]phenanthrene, pyrene, etc. Perylene, thiophene, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, pyrazolyl, thiazolyl, isothiazolyl, etc. azole group, isopropyl alcohol azole group, thiamethoxamyl group, thiamethoxamyl group Diazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolineyl, isoquinolineyl, benzoquinolineyl, phthalazinyl, naphthidyl, quinoxalinyl, quinoxalinyl, phenanthrene-pyridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl azole group, isobenzoxyl Azolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, or zazacarbazoyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 34 (Q) 35 -C(=O)(Q) 36 -S(=O)2(Q)37 ), or -P(=O)(Q 38 (Q) 39 ).

[0083] In one or more embodiments, L1 may be cyclohexylene, phenylene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, phenanthrene, anthracene, carbazolyl, dibenzofuranyl, dibenzothiophene, benzo[a]carbazolyl, dibenzo[a]carbazolyl, or dibenzothiophene; or

[0084] Each of the following substituted groups is a phenylene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, phenanthrene, anthracene, carbazolyl, dibenzofuranyl, dibenzothiophene, benzo[a]carbazolyl, dibenzo[a]carbazolyl, or dibenzothiophene: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 34 (Q) 35 -C(=O)(Q) 36 -S(=O)2(Q) 37 ), or -P(=O)(Q 38 (Q) 39 ).

[0085] In Equation 1B, a1 is 0, 1, 2, or 3.

[0086] In one or more embodiments, a1 can be 0, 1, or 2. In one or more embodiments, a1 can be 0 or 1.

[0087] In Equation 1B, Ar1, R1, R2, R 10 R 20 and R 41 -R 50 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9).

[0088] In Equation 1B, k1 is 1, 2, 3, 4, 5, 6, 7, or 8.

[0089] In one or more embodiments, k1 can be 1, 2, 3, 4, or 5.

[0090] In one or more embodiments, k1 can be 1, 2, or 3.

[0091] In Equation 1A, b10 and b20 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0092] In one or more embodiments, b10 and b20 may each be independently 1, 2, 3, 4, 5, 6, 7, or 8.

[0093] In one or more embodiments, b10 and b20 may each be 1, 2, 3, or 4 independently.

[0094] In one or more embodiments, b10 and b20 may each be 1 or 2 independently.

[0095] In one or more embodiments, b10 and b20 may each be 1 independently.

[0096] In one or more embodiments, Ar1, R1, R2, R 10 R 20 and R 41 -R 50 Each of these can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 Alkyl, or C1-C 20 Alkoxy;

[0097] Each of the C1-Cs is replaced by at least one of the following: 20 Alkyl or C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, or pyrimidinyl;

[0098] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl;

[0099] Each of the following is substituted with at least one of the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl; or

[0100] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9).

[0101] In one or more embodiments, Ar1, R1, R2, R 10 R 20 and R 41 -R 50 Each of these can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, Cl-C 60 Alkyl, C3-C 10 cycloalkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy group, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5); or

[0102] Groups represented by one of formulas 9-1 to 9-43, 9-201 to 9-237, 10-1 to 10-132, or 10-201 to 10-350:

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] In formulas 9-1 to 9-43, 9-201 to 9-237, 10-1 to 10-132, and 10-201 to 10-350, * can represent a binding site with an adjacent atom, "Ph" represents phenyl, "TMS" represents trimethylsilyl, and "TMG" represents trimethylgermanyl.

[0111] In one or more embodiments, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each can be independently:

[0112] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0113] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0114] Each of the following is replaced by n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or any combination thereof.

[0115] In one or more embodiments, in formula 1A, CY1 can be represented by one of formulas 1-1 to 1-16:

[0116]

[0117] Among them, in equations 1-1 to 1-16,

[0118] R 11 -R 14 Each of these can independently be deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, naphthyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3).

[0119] Where Q1-Q3 can be independently defined as follows:

[0120] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0121] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0122] Each of the following is replaced by n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or any combination thereof, and

[0123] * and *' each represent a binding site with an adjacent atom.

[0124] In one or more embodiments, in formula 1A, CY2 can be represented by one of formulas 2-1 to 2-16:

[0125]

[0126] Among them, in equations 2-1 to 2-16,

[0127] R 21 -R 24 Each of these can independently be deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, naphthyl, -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3).

[0128] Where Q1-Q3 can be independently defined as follows:

[0129] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0130] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0131] Each of the following is substituted by at least one of the following: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl or phenyl, and

[0132] * and *" each represent a binding site with an adjacent atom.

[0133] In one or more embodiments, *-(L1) in Formula 1B a1 -(Ar1) k1It can be expressed by one of equations 3-1 to 3-18:

[0134]

[0135] Among them, in equations 3-1 to 3-18,

[0136] Ar 11 -Ar 15 Each can be understood independently by referring to the description of Ar1 provided in this article, and

[0137] * indicates a binding site with an adjacent atom.

[0138] In one or more embodiments, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each can be independently:

[0139] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0140] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0141] Each of the following is substituted by at least one of the following: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl or phenyl.

[0142] In one or more embodiments, the organometallic compound may be represented by formula 11-1 or formula 11-2:

[0143] Formula 11-1

[0144]

[0145] Formula 11-2

[0146]

[0147] Among them, in equations 11-1 and 11-2,

[0148] M1, n1, n2, L1, a1, Ar1, and k1 can be understood by referring to the descriptions of M1, n1, n2, L1, a1, Ar1, and k1 provided in this document.

[0149] X 11 It can be C(R) 11 ) or N, X 12 It can be C(R) 12 ) or N, X 13 It can be C(R) 13 ) or N, and X 14 It can be C(R) 14 ) or N,

[0150] X 21 It can be C(R) 21 ) or N, X 22 It can be C(R) 22 ) or N, X 23 It can be C(R) 23 ) or N, and X 24 It can be C(R) 24 ) or N,

[0151] X 33 It can be C(R) 33 ) or N, X 34 It can be C(R) 34 ) or N, X 35 It can be C(R) 35 ) or N, and X 36 It can be C(R) 36 ) or N,

[0152] R 11 -R 14 Each can be independently obtained by referring to the R provided in this article. 10 Based on the description,

[0153] R 21 -R 24 Each can be independently obtained by referring to the R provided in this article. 20 Based on the description,

[0154] R 31 -R 36 Each can be understood independently by referring to the description of R1 provided in this article.

[0155] R 11 -R 14 At least two of them may be optionally combined to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Replacement C1-C 30Heterocyclic groups,

[0156] R 21 -R 24 At least two of them may be optionally combined to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0157] R 31 -R 36 At least two of them may be optionally combined to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Replacement C1-C 30 Heterocyclic groups, and

[0158] R 10a You can refer to the R provided in this article 10 Understanding is based on the description.

[0159] In one or more embodiments, "not replaced or by at least one R" 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Replacement C1-C 30 Examples of "heterocyclic groups" include those that are not substituted or are substituted by at least one R. 10a Substituted phenyl groups, naphthyl groups, cyclopentyl groups, cyclopentadienyl groups, cyclohexyl groups, cycloheptyl groups, bicyclic [2.2.1]heptyl groups, furan groups, thiophene groups, pyrrole groups, thiophene groups, indole groups, benzofuran groups, benzothiophene groups, indole groups, or benzothiophene groups. R 10a You can refer to the R provided in this article 10 Understand from the description. C5-C 30 Carbocyclic groups and C1-C 30 Heterocyclic groups can be obtained by referring to the C5-C provided in this article. 30 Carbocyclic groups and C1-C 30 Understanding is achieved through the description of heterocyclic groups.

[0160] In one or more embodiments, the organometallic compound may be a compound represented by any one of formulas 12-1 to 12-6:

[0161] Equation 12-1

[0162]

[0163] Equation 12-2

[0164]

[0165] Equation 12-3

[0166]

[0167] Equation 12-4

[0168]

[0169] Formula 12-5

[0170]

[0171] Formula 12-6

[0172]

[0173] Among them, in equations 12-1 to 12-6,

[0174] M1, n1, n2, L1, a1, Ar1, k1, and R 41 -R 50 This can be achieved by referring to M1, n1, n2, L1, a1, Ar1, k1, and R provided in this article. 41 -R 50 Based on the description,

[0175] R 11 -R 14 Each can be independently obtained by referring to the R provided in this article. 10 Based on the description,

[0176] R 21 -R 24 Each can be independently obtained by referring to the R provided in this article. 20 Understanding based on the description, and

[0177] R 31 -R 36 and R 31a -R 38a Each can be understood independently by referring to the description of R1 provided in this article.

[0178] In one or more embodiments, in formulas 12-1 to 12-6,

[0179] R 11 -R 14 At least two of them may be optionally combined to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10aReplacement C1-C 30 Heterocyclic groups,

[0180] R 21 -R 24 At least two of them may be optionally combined to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Replacement C1-C 30 Heterocyclic groups, and

[0181] R 31 -R 36 and R 31a -R 38a At least two of them may be optionally combined to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Replacement C1-C 30 Heterocyclic groups.

[0182] R 10a You can refer to the R provided in this article 10a Understanding is based on the description.

[0183] R 11 -R 14 R 21 -R 24 R 31 -R 36 and R 31a -R 38a At least two adjacent groups may optionally combine to form a phenyl group or a naphthalene group.

[0184] In one or more embodiments, Ar1, R1, R2, R 10 R 20 and R 41 -R 50 At least one of them may be a substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 60 Aryl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3).

[0185] In one or more embodiments, Ar1, R1, R2, R 10 R 20 and R 41 -R 50At least one of the following can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, biphenyl, C1-C 20 Alkylphenyl, naphthyl, -Si(Q1)(Q2)(Q3), or -Ge(Q1)(Q2)(Q3).

[0186] In one or more embodiments, the organometallic compound may be a compound of compounds 1 to 28:

[0187]

[0188]

[0189] In one or more embodiments, the organometallic compound may be electrically neutral.

[0190] The organometallic compound represented by Formula 1 satisfies the structure of Formula 1 and includes a dicoordinate ligand comprising imidazole and benzo[9,10]phenanthrene. Due to this structure, the organometallic compound represented by Formula 1 can have improved emission properties. In particular, the organometallic compound can be made suitable for use as an emitting material with high color purity by controlling the emission wavelength.

[0191] Furthermore, organometallic compounds represented by Formula 1 can exhibit excellent electron mobility. Therefore, electronic devices including these organometallic compounds, such as organic light-emitting devices, can have low driving voltage, high efficiency, long lifetime, and reduced roll-off.

[0192] Furthermore, organometallic compounds represented by Formula 1 can possess improved photochemical stability. Therefore, electronic devices including said organometallic compounds, such as organic light-emitting devices, can have improved emission efficiency, lifetime, and color purity.

[0193] Some HOMO, LUMO, band gap, S1, and T1 levels of organometallic compounds represented by Equation 1 were evaluated using Gaussian 09 with molecular structure optimization based on density functional theory (DFT) at the B3LYP level. The results are shown in Table 1, where energies are reported as electron volts (eV).

[0194] Table 1

[0195]

[0196]

[0197] Referring to the results in Table 1, it was found that the organometallic compounds represented by Formula 1 have electrical properties suitable for use as dopants in electronic devices such as organic light-emitting devices.

[0198] In one or more embodiments, the half-width (FWHM) of the photoluminescence or electroluminescence spectrum of the organometallic compound may be 75 nanometers (nm) or less. For example, the FWHM of the photoluminescence or electroluminescence spectrum of the organometallic compound may be in the range of about 20 nm to about 72 nm, about 25 nm to about 70 nm, about 30 nm to about 65 nm, about 40 nm to about 63 nm, or about 45 nm to about 62 nm.

[0199] The maximum emission wavelength (emission peak wavelength, λ) in the photoluminescence or electroluminescence spectrum of the organometallic compound. 最大 It can be in the range of approximately 500 nm to approximately 600 nm. For example, λ 最大 It can be about 520nm to about 600nm, or about 510nm to about 590nm, or about 520nm to about 590nm, or about 525nm to about 580nm, or about 520nm to about 580nm.

[0200] The method for synthesizing the organometallic compounds represented by Formula 1 will be clear to those skilled in the art by referring to the synthesis examples provided herein.

[0201] The organometallic compound represented by Formula 1 is suitable for use in the organic layer of an organic light-emitting device, for example as a dopant in the emitting layer of the organic layer. Therefore, according to another aspect, an organic light-emitting device is provided, which may include: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, wherein the organic layer includes an emitting layer and at least one organometallic compound represented by Formula 1.

[0202] Since the organic light-emitting device may include an organic layer comprising an organometallic compound represented by Formula 1, the organic light-emitting device may exhibit excellent driving voltage, current efficiency, power efficiency, external quantum yield, lifetime, and / or color purity characteristics. Furthermore, roll-off can be reduced, and therefore, a relatively narrow FWHM in the electroluminescence (EL) spectrum emission peak can be achieved.

[0203] Organometallic compounds represented by Formula 1 can be used between electrode pairs in organic light-emitting devices. For example, an organometallic compound represented by Formula 1 can be included in the emitting layer. In this embodiment, the organometallic compound can act as a dopant, and the emitting layer can further include a host (i.e., the amount of the organometallic compound represented by Formula 1 in the emitting layer can be less than the amount of the host).

[0204] In one or more embodiments, the emitting layer can emit green light. In one or more embodiments, the emitting layer can emit green light having a maximum emission wavelength in the range of about 500 nanometers (nm) to about 600 nm.

[0205] As used herein, “(e.g., the organic layer) comprises at least one organometallic compound” means “(the organic layer) comprises one organometallic compound of formula 1, or at least two different organometallic compounds of formula 1.”

[0206] For example, only compound 1 may be included in the organic layer as an organometallic compound. In this embodiment, compound 1 may be included in the emitting layer of the organic light-emitting device. In one or more embodiments, compounds 1 and 2 may be included in the organic layer as organometallic compounds. In this embodiment, both compounds 1 and 2 may be included in the same layer (e.g., both compounds 1 and 2 may be included in the emitting layer).

[0207] The first electrode may be the anode of the hole injection electrode, and the second electrode may be the cathode of the electron injection electrode. In one or more embodiments, the first electrode may be the cathode of the electron injection electrode, and the second electrode may be the anode of the hole injection electrode.

[0208] For example, in the organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region located between the first electrode and the emitting layer and an electron transport region located between the emitting layer and the second electrode. The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0209] As used herein, the term "organic layer" refers to a single layer and / or multiple layers located between the first and second electrodes in an organic light-emitting device. "Organic layer" may include not only organic compounds but also organometallic complexes containing metals.

[0210] Figure 1 A schematic cross-sectional view illustrating an organic light-emitting device 10 according to one or more embodiments is shown below. Reference will be made to... Figure 1 The structure of an organic light-emitting device according to one or more embodiments and a method of manufacturing the organic light-emitting device are described. The organic light-emitting device 10 may include a first electrode 11, an organic layer 15, and a second electrode 19, which may be stacked sequentially in the order stated herein.

[0211] The substrate may be additionally disposed below the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in organic light-emitting devices, such as a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0212] The first electrode 11 can be formed by depositing or sputtering a material for forming the first electrode 11 onto a substrate. The first electrode 11 can be an anode. The material used to form the first electrode 11 can be a material with a high work function that facilitates hole injection. The first electrode 11 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. The material used to form the first electrode 11 can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material used to form the first electrode 11 can be a metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0213] The first electrode 11 may have a multilayer structure comprising multiple layers or a single-layer structure. In one or more embodiments, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the embodiments are not limited thereto.

[0214] The organic layer 15 may be on the first electrode 11.

[0215] The organic layer 15 may include a hole transport region, an emitter layer, and an electron transport region.

[0216] The hole transport region may be located between the first electrode 11 and the emitter layer.

[0217] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.

[0218] The hole transport region may include a hole injection layer or a hole transport layer only. In one or more embodiments, the hole transport region may include a hole injection layer and a hole transport layer sequentially stacked on the first electrode 11. In one or more embodiments, the hole transport region may include a hole injection layer, a hole transport layer, and an electron blocking layer sequentially stacked on the first electrode 11.

[0219] When the hole transport region includes a hole injection layer, the hole injection layer can be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, tape casting, and Langmuir-Broguet (LB) deposition.

[0220] When a hole injection layer is formed by vacuum deposition, for example, vacuum deposition can be performed at a deposition temperature in the range of about 100°C to about 500°C. -8 To about 10 -3 At a vacuum level within the Torr range and at approximately 0.01 angstroms per second ( ( / second) to approximately The deposition is carried out at a rate in the range of / second, however the conditions can vary depending on the compound used as the hole injection material and the structure and thermal properties of the desired hole injection layer, but the conditions for vacuum deposition are not limited to this.

[0221] When a hole injection layer is formed by spin coating, the spin coating can be carried out at a coating rate in the range of about 2,000 rpm to about 5,000 rpm and at a temperature in the range of about 80°C to 200°C to promote the removal of solvent after spin coating. However, the conditions can vary depending on the compound used as the hole injection material and the structure and thermal properties of the desired hole injection layer, but the conditions for spin coating are not limited to these.

[0222] The conditions for forming the hole transport layer and the electron blocking layer can be inferred from the conditions for forming the hole injection layer.

[0223] The hole transport region may include at least one of the following: m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-sulfonated styrene) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), (polyaniline) / poly(4-sulfonated styrene) (PANI / PSS), compounds represented by formula 201, and compounds represented by formula 202:

[0224]

[0225] Formula 201

[0226]

[0227] Formula 202

[0228]

[0229] In Equation 201, Ar 101 and Ar 102 Each can be independently:

[0230] Phenylidene, cyclopentadienyl, indene, naphthyl, azulene, heptadienyl, acenaphthene, fluorene, phenenyl, phenanthrene, anthracene, fluoranyl, benzo[9,10]phenanthrene, pyrene, phenylene alkyl, benzotetraphenyl, terephthalyl, perylene, or benzopentaphenyl; and

[0231] Each of the following is substituted with at least one of the following: phenylene, cyclopentadienylene, indene, naphthylene, azurylene, heptadienylene, acenaphthene, fluorene, phenenylene, phenanthrene, anthracene, fluoranthracene, benzo[9,10]phenanthrene, pyrene, etc. alkyl, tetraphenylene, terephthalyl, perylene, or pentaphenylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroarylalkyl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heterocyclic group.

[0232] In Equation 201, xa and xb can each be an integer from 0 to 5 independently. In one or more embodiments, xa and xb can each be an integer from 0 to 2 independently. In one or more embodiments, xa can be 1 and xb can be 0, but the embodiments are not limited thereto.

[0233] In equations 201 and 202, R 101 -R 108 R 111 -R 119 and R 121 -R 124 Each can be independently:

[0234] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, or hexyl), or C1-C 10 Alkyl groups (e.g., methoxy, ethoxy, propoxy, butoxy, or pentoxy);

[0235] Each of the C1-Cs is replaced by at least one of the following: 10 Alkyl or C1-C 10 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, or phosphate group or its salt;

[0236] Phenyl, naphthyl, anthraceneyl, fluorenyl, or pyrene; or

[0237] Each of the following is substituted with at least one of the following: phenyl, naphthyl, anthraceneyl, fluorenyl, or pyrene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, or C1-C 10 Alkoxy groups, but the implementation methods are not limited to this.

[0238] In Equation 201, R 109 Possible forms:

[0239] phenyl, naphthyl, anthraceneyl, or pyridyl; or

[0240] Each of the following is substituted by at least one of the following: phenyl, naphthyl, anthracene, or pyridyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, anthraceneyl, or pyridyl.

[0241] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A, but the embodiments are not limited thereto:

[0242] Formula 201A

[0243]

[0244] In Equation 201A, R 101 R 111 R 112 and R109 You can refer to the R provided in this article respectively. 101 R 111 R 112 and R 109 Understanding is based on the description.

[0245] In one or more embodiments, the compounds represented by formulas 201 and 202 may include compounds HT1 to HT20, but the embodiments are not limited thereto:

[0246]

[0247]

[0248] The thickness of the hole transport region can be approximately 100 angstroms. -about For example, about -about Within the range. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer can be approximately -about For example, about -about Within a certain range, the thickness of the hole transport layer can be approximately -about For example, about -about Within these ranges, excellent hole transport characteristics can be obtained without a significant increase in driving voltage when the thicknesses of the hole transport region, hole injection layer, and hole transport layer are within any of these ranges.

[0249] In addition to the materials mentioned above, the hole transport region may include a charge-generating material to improve the conductivity of the hole transport region. The charge-generating material may be distributed substantially uniformly or non-uniformly in the hole transport region.

[0250] The charge-generating material may include, for example, a p-doper. The p-doper may include one of the following: quinone derivatives, metal oxides, and compounds containing a cyano group, but the embodiments are not limited thereto. For example, non-limiting examples of the p-doper include: quinone derivatives such as tetracyanoquinone dimethyl (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; and compounds containing a cyano group such as compound HT-D1 or compound F12, but the embodiments are not limited thereto.

[0251]

[0252] The hole transport region may further include a buffer layer.

[0253] The buffer layer can compensate for the optical resonant distance depending on the wavelength of the light emitted from the emission layer to improve the efficiency of the organic light-emitting device.

[0254] An emitter layer can be formed on the hole transport region using one or more suitable methods such as vacuum deposition, spin coating, casting, or LB deposition. When the emitter layer is formed by vacuum deposition or spin coating, the vacuum deposition and coating conditions used to form the emitter layer are generally similar to those used to form the hole injection layer; however, these conditions may vary depending on the compound used.

[0255] When the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may be selected from the materials and body materials described herein for forming the hole transport region, but the implementation is not limited thereto. In one or more embodiments, when the hole transport region includes an electron blocking layer, the mCP described herein may be used to form the electron blocking layer.

[0256] The emitter layer may include a host and a dopant, and the dopant may include an organometallic compound represented by Formula 1.

[0257] The main body may include at least one of TPBi, TBADN, ADN (also known as "DNA"), CBP, CDBP, TCP, mCP, compounds H50 and H51, and GH3:

[0258]

[0259] In one or more embodiments, the body may further comprise a compound represented by formula 301:

[0260] Formula 301

[0261]

[0262] In Equation 301, Ar 111 and Ar 112 Each can be independently:

[0263] Phenylidene, naphthylene, phenanthrene, or pyrene; or

[0264] Each of the following is substituted with at least one of the following: phenylene, naphthylene, phenanthrene, or pyrene: phenyl, naphthyl, or anthracene.

[0265] In Equation 301, Ar 113 -Ar 116 Each can be independently:

[0266] C1-C 10Alkyl, phenyl, naphthyl, phenanthrene, or pyrene; or

[0267] Each of the following is substituted with at least one of the following: phenyl, naphthyl, phenanthryl, or pyrene: phenyl, naphthyl, or anthracene.

[0268] In Equation 301, g, h, i, and j can each be an integer from 0 to 4 independently. In one or more embodiments, g, h, i, and j can each be 0, 1, or 2 independently.

[0269] In Equation 301, Ar 113 -Ar 116 Each can be independently:

[0270] C1-C substituted with phenyl, naphthyl, anthracene, or any combination thereof 10 alkyl;

[0271] Phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, or fluoreneyl;

[0272] Each of the following is substituted with at least one of the following: phenyl, naphthyl, anthraceneyl, pyrene, phenanthrene, or fluorenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, or fluoreneyl; or

[0273] Groups represented by the following:

[0274]

[0275] In one or more embodiments, the body may include a compound represented by formula 302:

[0276] Formula 302

[0277]

[0278] In Equation 302, Ar 122 -Ar 125 Each can be independently referred to Ar in Equation 301 provided in this document. 113 Understanding is based on the description.

[0279] In Equation 302, Ar 126 and Ar 127 Each can be independently C1-C 10 Alkyl (e.g., methyl, ethyl, or propyl).

[0280] In Equation 302, k and l can each be independent integers from 0 to 4. In one or more embodiments, k and l can each be 0, 1, or 2.

[0281] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, and a blue emitting layer. In one or more embodiments, the emitting layer may have a structure in which the red emitting layer, the green emitting layer, and / or the blue emitting layer are stacked to emit white light. In one or more embodiments, the structure of the emitting layer may be modified.

[0282] When the emitter layer comprises a substrate and a dopant, the amount of the dopant may be selected from about 0.01 parts by weight to about 15 parts by weight, based on about 100 parts by weight of the substrate, but the implementation is not limited thereto.

[0283] The thickness of the emission layer can be approximately -about and in one or more embodiments -about Within these ranges, improved light emission characteristics can be obtained without a significant increase in driving voltage when the thickness of the emitting layer is within any of these ranges.

[0284] Next, an electron transport region can be formed on the emitter layer.

[0285] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0286] In one or more embodiments, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure, but the embodiments are not limited thereto. The electron transport layer may have a multilayer structure or a single-layer structure comprising two or more different materials.

[0287] Based on the conditions for forming the hole injection layer, the conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer can be deduced.

[0288] When the electron transport region includes a hole blocking layer, the hole blocking layer may include at least one of, for example, BCP, Bphen, and BAlq, but the implementation is not limited thereto:

[0289]

[0290] The thickness of the hole-blocking layer can be approximately -about For example, about -about Within these ranges, excellent hole blocking characteristics can be obtained without a significant increase in driving voltage when the thickness of the hole blocking layer is within any of these ranges.

[0291] The electron transport layer may include at least one of BCP, Bphen, Alq3, BAlq, TAZ, and NTAZ:

[0292]

[0293] In one or more embodiments, the electron transport layer may include at least one of compounds ET1 to ET25, but the embodiments are not limited thereto:

[0294]

[0295]

[0296] The thickness of the electron transport layer can be approximately -about and in one or more embodiments about Within these ranges, excellent electron transport characteristics can be obtained without a significant increase in driving voltage when the thickness of the electron transport layer is within any of these ranges.

[0297] In addition to the materials described above, the electron transport layer may further include a material comprising metal.

[0298] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (LiQ) or compound ET-D2.

[0299]

[0300] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 19.

[0301] The electron injection layer may include at least one of LiF, NaCl, CsF, Li2O, BaO, or combinations thereof.

[0302] The thickness of the electron injection layer can be approximately -about and in one or more embodiments -about Within these ranges, excellent electron injection characteristics can be obtained without a significant increase in driving voltage when the thickness of the electron injection layer is within any of these ranges.

[0303] The second electrode 19 may be on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a material with a relatively low work function, such as a metal, alloy, conductive compound, or mixture thereof. Examples of materials used to form the second electrode 19 may include at least one of the following: lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or combinations thereof. In one or more embodiments, ITO or IZO may be used to form the transmissive second electrode 19 to fabricate a top-emitting light-emitting device. In one or more embodiments, the material used to form the second electrode 19 may be varied.

[0304] In the previous text, it has been referenced Figure 1 Organic light-emitting device 10 has been described, but the implementation is not limited thereto.

[0305] According to another aspect of the embodiment, the diagnostic composition may include at least one organometallic compound represented by Formula 1.

[0306] Since organometallic compounds represented by Formula 1 provide high luminescence efficiency, diagnostic compositions comprising organometallic compounds represented by Formula 1 can have excellent diagnostic efficiency.

[0307] The diagnostic composition can be used in a variety of ways, such as in diagnostic kits, diagnostic reagents, biosensors, or biomarkers.

[0308] As used in this article, the term "C1-C" 60 "Alkyl" refers to a straight-chain or branched monovalent group of a saturated aliphatic hydrocarbon having 1-60 carbon atoms. Examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. The term "C1-C" is used as in this document. 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Divalent groups with the same structure as alkyl groups.

[0309] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups. Examples include methoxy, ethoxy, and isopropoxy.

[0310] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed by the carbon atoms in the C2-C2 group. 60 A group formed by placing at least one carbon-carbon double bond at the middle or end of an alkyl group. Examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used in this context.60 "Alkenyl" refers to a group with a C2-C ratio. 60 Divalent groups with the same structure as alkenyl groups.

[0311] As used in this article, the term "C2-C" 60 "Alkyne" refers to the group formed by the combination of C2-C... 60 A group formed by placing at least one carbon-carbon triple bond at the middle or end of an alkyl group. Examples include ethynyl and propynyl groups. As used herein, the term "C2-C" is used in this context. 60 "Alynyl group" refers to a group with a C2-C group. 60 Divalent groups with the same structure as alkynyl groups.

[0312] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monovalent, monocyclic, saturated hydrocarbon group comprising 3 to 10 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C" is also relevant. 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Divalent groups with the same structure as cycloalkyl groups.

[0313] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated monocyclic group comprising at least one heteroatom of N, O, P, Si, S, B, Ge, and Se replacing a carbon atom as a cyclizing atom and consisting of 1-10 carbon atoms. Examples include tetrahydrofuranyl and tetrahydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with the same structure as heterocyclic alkyl groups.

[0314] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3-10 carbon atoms and at least one carbon-carbon double bond in its ring, wherein the overall molecular structure is non-aromatic. Examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also relevant. 10 "Cyclopentene" refers to a group with a C3-C6 bond structure. 10 A divalent group with the same structure as a cycloalkenyl group.

[0315] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group in which at least one heteroatom of N, O, P, Si, S, B, Ge, or Se replaces a carbon atom as a cyclic atom, consists of 2-10 carbon atoms, and has at least one double bond, and the overall molecular structure is non-aromatic. (C1-C) 10Examples of heterocyclic alkenyl groups include 2,3-dihydrofuranyl and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to a group that has a C1-C2 bond structure. 10 Divalent groups with the same structure as heterocyclic alkenyl groups.

[0316] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group in a carbocyclic aromatic system having 6-60 carbon atoms. For example, the term "C6-C" is used herein. 60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system with 6-60 carbon atoms. (C6-C) 60 Examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and... Base. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises multiple rings, the multiple rings can be fused together. As used herein, the term "C7-C" is relevant to this context. 60 "alkylaryl" refers to an alkyl group formed by at least one C1-C2 group. 54 Alkyl-substituted C6-C 59 Aryl. As used in this text, the term "C7-C" 60 "Arylalkyl" refers to an alkyl group consisting of at least one C6-C2 group. 59 aryl-substituted C1-C 54 alkyl.

[0317] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system in which at least one heteroatom of N, O, P, Si, S, B, Ge, or Se replaces a carbon atom as a cyclizing atom and there are 1-60 carbon atoms. The term "C1-C" is used herein. 60 "Hypo-heteroaryl" refers to a divalent group having a heterocyclic aromatic system in which at least one heteroatom of N, O, P, Si, S, B, Ge, or Se replaces a carbon atom as a cyclizing atom and there are 1-60 carbon atoms. C1-C 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C... 60 heteroaryl and C1-C 60 When each heteroaryl group comprises multiple rings, the multiple rings can be fused together. As used herein, the term "C2-C" is relevant to this context. 60 "alkyl heteroaryl" refers to an alkyl group formed by at least one C1-C2 group. 59 Alkyl-substituted C1-C 59 heteroaryl. As used herein, the term "C2-C" is used in this text. 60"Heteroarylalkyl" refers to an alkyl group consisting of at least one C1-C2 group. 59 heteroaryl-substituted C1-C 59 alkyl.

[0318] As used in this article, the term "C6-C" 60 "Aryloxy group" represents -OA 102 (where A) 102 For C6-C 60 Aryl). As used herein, the term "C6-C" 60 "Arylthio" indicates -SA 103 (where A) 103 For C6-C 60 Aryl).

[0319] As used in this article, the term "C1-C" 60 "Heteroaryloxy" indicates -OA 104 (where A) 104 For C1-C 60 (Heteroaryl). As used herein, the term "C1-C" 60 "Heteroarylsulfonyl" indicates -SA 105 (where A) 105 For C1-C 60 (Miscellaneous aromatic compounds).

[0320] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group having two or more fused rings and having only carbon atoms (e.g., the number of carbon atoms can range from 8 to 60) as cyclic atoms, wherein the molecular structure as a whole is nonaromatic. Examples of such monovalent nonaromatic fused polycyclic groups include the fluorene group. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having a structure substantially the same as that of a monovalent nonaromatic fused polycyclic group.

[0321] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group having two or more fused rings and having heteroatoms selected from N, O, P, Si, S, B, Ge, and Se, as well as carbon atoms (e.g., the number of carbon atoms can range from 1 to 60) as cyclic atoms, wherein the molecular structure as a whole is nonaromatic. Examples of such monovalent nonaromatic fused heterocyclic groups include the carbazole group. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having substantially the same structure as the monovalent nonaromatic fused heterocyclic group.

[0322] As used in this article, the term "C5-C" 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group consisting of only 5-30 carbon atoms as cyclic atoms. (C5-C) 30The carbon ring group can be a monocyclic group or a polycyclic group.

[0323] As used in this article, the term "C1-C" 30 A "heterocyclic group" refers to a saturated or unsaturated cyclic group comprising 1-30 carbon atoms and at least one heteroatom selected from N, O, P, Si, S, B, Ge, and Se as the cyclic atom. C1-C 30 Heterocyclic groups can be monocyclic or polycyclic.

[0324] As used in this paper, “TMS” represents -Si(CH3)3, and “TMG” represents -Ge(CH3)3.

[0325] Replacement C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Heteroaryl groups, substituted divalent nonaromatic fused polycyclic groups, substituted divalent nonaromatic fused heterocyclic groups, substituted C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 heteroaryl thiols, substituted C2-C 60 Heteroarylalkyl, substituted C2-C 60 At least one substituent of the alkyl heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group may be:

[0326] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy;

[0327] Each of the C1-Cs is replaced by at least one of the following: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroarylalkyl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 ), or -P(=O)(Q 18 (Q) 19 );

[0328] C3-C 10 cycloalkyl, C1-C10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroarylalkyl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heterocyclic group;

[0329] Each of the C3-C molecules is replaced by at least one of the following: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroarylalkyl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C2-C 60 Heteroarylalkyl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 ), or -P(=O)(Q 28 (Q) 29 );or

[0330] -Si(Q 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 ), or -P(=O)(Q 38 (Q) 39 ),

[0331] Among them, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 heteroaryl thiols, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic group, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic group.

[0332] The compounds and organic light-emitting devices according to one or more embodiments are described in detail below with reference to synthesis examples and embodiments; however, this disclosure is not limited thereto. The phrase "using B instead of A" used in describing the synthesis examples means using the same molar equivalent of B instead of A.

[0333] Example

[0334] Synthesis Example 1: Synthesis of Compound 1

[0335]

[0336] (1) Synthesis of compound 1A

[0337] 5.0 g (31.9 mmol) of 2-phenylpyridine and 5.0 g (14.2 mmol) of iridium chloride hydrate were mixed with 120 mL of ethoxyethanol and 40 mL of distilled water. The mixture was then stirred under reflux for about 24 hours to allow the reaction to proceed, and the temperature was then lowered to room temperature. A solid was formed, which was then separated by filtration. The solid was thoroughly washed with water, methanol, and hexane in the order stated above, and dried in a vacuum oven to obtain 7.9 g of compound 1A (yield: 89%). The obtained compound 1A was used in subsequent reactions without any further purification.

[0338] (2) Synthesis of compound 1B

[0339] 1.6 g (1.5 mmol) of compound 1A was mixed with 45 mL of dichloromethane (MC), and a solution of 0.8 g (3.1 mmol) of AgCF3SO3 (AgOTf) dissolved in 15 mL of methanol (MeOH) was added. The mixture was then stirred at room temperature for 18 hours while blocking light through an aluminum foil. The result was filtered through diatomaceous earth to remove the resulting solid, and then filtered under reduced pressure to obtain a solid (compound 1B). This solid was used in subsequent reactions without any further purification.

[0340] (3) Synthesis of compound 2A

[0341] Under a nitrogen atmosphere, 2.0 g (5.5 mmol) of 4,4,5,5-tetramethyl-2-(benzo[9,10]phenanthrene-2-yl)-1,3,2-dioxane and 2.0 g (4.6 mmol) of 2-bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole were dissolved in 100 mL of tetrahydrofuran (THF). Then, 1.5 g (13.9 mmol) of potassium carbonate (K₂CO₃) was dissolved in 25 mL of distilled water and added to the resulting mixture. Subsequently, 0.53 g (0.46 mmol) of tetra(triphenylphosphine)palladium(O)(Pd(PPh₃)₄) was added. The resulting mixture was then stirred under reflux at 100 °C. Following extraction, the resulting solid was subjected to column chromatography (using dichloromethane (MC) and hexane as eluent) to yield 2.5 g of 1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-2-(benzo[9,10]phenanthrene-2-yl)-1H-benzo[d]imidazole (yield: 93%). The obtained compound was identified by high-resolution mass spectrometry (HRMS) using matrix-assisted laser desorption / ionization (MALDI) and by high-performance liquid chromatography (HPLC).

[0342] HRMS (MALDI): For C 43 H 36 Calculated value of N2: m / z: 580.29; Measured value: 581.37

[0343] (4) Synthesis of Compound 1

[0344] 100 mL of ethoxyethanol was mixed with 1.5 g (2.1 mmol) of compound 1B and 1.4 g (2.3 mmol) of compound 2A. The mixture was stirred under reflux for 24 hours. Then, the temperature was lowered. The resulting mixture was subjected to extraction with dichloromethane and water to remove the aqueous layer. The result was treated with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. The resulting solid was subjected to column chromatography (eluent: dichloromethane (MC) and hexane) to obtain 0.8 g of compound 1 (yield: 35%). The obtained compounds were identified by analysis using HRMS (MALDI) and HPLC.

[0345] HRMS (MALDI): For C 71 H 54 Calculated value of IrN5O: m / z: 1080.37; Measured value: 1081.33

[0346] Synthesis Example 2: Synthesis of Compound 2

[0347]

[0348] (1) Synthesis of compound 3A

[0349] 2.4 g of 1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-2-(benzo[9,10]phenanthrene-2-yl)-1H-naphtho[1,2-d]imidazole (yield: 92%) was prepared in essentially the same manner as in the synthesis of compound 2A, except that 2.0 g (4.1 mmol) of 2-bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-naphtho[1,2-d]imidazole was used instead of 2-bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole. The obtained compounds were identified by mass spectrometry and HPLC analysis.

[0350] HRMS (MALDI): For C 47 H 38 Calculated value of N2: m / z: 630.30; Measured value: 631.83

[0351] (2) Synthesis of compound 2

[0352] Compound 2 (yield: 31%) was obtained in substantially the same manner as in the synthesis of compound 1, except that 1.5 g (2.3 mmol) of compound 3A and 1.5 g (2.1 mmol) of compound 1B were used. The obtained compounds were identified by mass spectrometry and HPLC analysis.

[0353] HRMS (MALDI): For C69 H 53 Calculated value of IrN4: m / z: 1130.39; Measured value: 1131.43

[0354] Synthesis Example 3: Synthesis of Compound 3

[0355]

[0356] (1) Synthesis of compound 3

[0357] Compound 3 (yield: 34%) was obtained in essentially the same manner as in the synthesis of compound 1, except that 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 2-phenyl-pyridine in the synthesis of compound 1A. The obtained compounds were identified by mass spectrometry and HPLC analysis.

[0358] HRMS (MALDI): For C 79 H 83 Calculated value of IrN4Si2: m / z: 1336.58; Measured value: 1337.95

[0359] Example 1

[0360] A glass substrate with ITO patterned on it as an anode was cut to a size of 50 mm × 50 mm × 0.5 mm, ultrasonically treated in isopropanol and water for 5 minutes each, and cleaned by exposure to ultraviolet light and ozone for 30 minutes. The glass substrate was then mounted on a vacuum deposition apparatus.

[0361] Compound HT3 and compound F12 (p-doper) were co-deposited on the anode in a weight ratio of 98:2 under vacuum to form a structure with... A hole injection layer of a certain thickness is formed. Then, compound HT3 is vacuum-deposited onto the hole injection layer to form a layer with… A hole transport layer of a certain thickness.

[0362] Subsequently, compound GH3 (as the host) and compound 1 (as the dopant) were co-deposited on the hole transport layer at a weight ratio of 92:8 to form a structure with... The thickness of the emission layer.

[0363] Compound ET3 and compound LiQ (n-doper) were co-deposited on the emitter layer in a 50:50 volume ratio to form a structure with... An electron transport layer of a certain thickness is formed by vacuum deposition of the compound LiQ (n-doper) onto the electron transport layer to form an electron transport layer with a thickness of [missing information]. An electron-injected layer of a certain thickness is formed, and Al is vacuum-deposited on the electron-injected layer to form a layer with [missing information]. A cathode of a certain thickness is used to complete the fabrication of organic light-emitting devices.

[0364]

[0365] Examples 2 and 3 and Comparative Examples 1-3

[0366] The organic light-emitting device (OLED) was fabricated in essentially the same manner as in Example 1, except that, when forming the emission layer, the compounds shown in Table 2 were used instead of compound 1 as dopants.

[0367] The driving voltage, external quantum efficiency (EQE, %), and maximum emission wavelength (λ) of the organic light-emitting devices fabricated in Examples 1-3 and Comparative Examples 1-3 were evaluated. 最大 (nm), FWHM (nm), and lifetime (LT) 97 (relative values). The results are shown in Table 2. A Keithley 2400 ammeter / voltmeter and a luminance meter (Minolta Cs-1000A) were used in the evaluation. Lifetime (LT) 97 This refers to the 18,000 candela per square meter (cd / m²) of organic light-emitting devices. 2 The time required for the initial brightness (or nits) to decrease to 97%, and its lifetime report relative to Comparative Example 1.

[0368] Table 2

[0369]

[0370]

[0371]

[0372] Referring to the results in Table 2, it was found that the organic light-emitting devices of Examples 1-3 each possess low driving voltage, small FWHM, and excellent external quantum yield and lifetime characteristics. Furthermore, compared to the organic light-emitting devices of Comparative Examples 1-3, it was found that the organic light-emitting devices of Examples 1-3 have low or similar driving voltage, narrow FWHM, and excellent external quantum yield and lifetime characteristics.

[0373] The organometallic compounds can possess excellent electrical properties and thermal stability. In particular, due to their high glass transition temperature, crystallization of the organometallic compounds can be prevented, and electron mobility can be improved. Therefore, electronic devices including the organometallic compounds, such as organic light-emitting devices, can have low driving voltage, high efficiency, long lifetime, reduced roll-off ratio, and a relatively narrow field of view (FWHM) of emission peaks in the EL spectrum.

[0374] Therefore, organic light-emitting devices with excellent quality can be achieved by using the aforementioned organometallic compounds. Furthermore, diagnostic compositions including the aforementioned organometallic compounds can have high diagnostic efficiency because the organometallic compounds exhibit excellent phosphorescence emission properties.

[0375] It should be understood that the exemplary embodiments described herein are to be considered in the descriptive sense and are not intended for limiting purposes. The descriptions of features or aspects in the various exemplary embodiments should typically be considered applicable to other similar features or aspects in other exemplary embodiments. Although one or more exemplary embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims.

Claims

1. Organometallic compounds represented by formula 12-2 or 12-5: Equation 12-2 Formula 12-5 in, In equations 12-2 and 12-5, M1 is Ir, n1 is 1 or 2. n2 is 1 or 2. The sum of n1 + n2 is 3. -(L1) a1 -(Ar1) k1 Represented by one of equations 3-1 to 3-18: Among them, in equations 3-1 to 3-18, Indicates the binding site with adjacent atoms. Ar 11 -Ar 15 Each independently is: C1-C 20 alkyl; C1-C replaced by at least one of the following 20 Alkyl groups: deuterium, CD3, -CD2H, -CDH2, or C1-C 10 alkyl; phenyl; or A phenyl group substituted with at least one of the following: deuterium, -CD3, -CD2H, -CDH2, or C1-C. 10 alkyl, R 11 -R 14 R 21 -R 24 R 31 -R 36 R 31a -R 38a R 41 -R 49 and R 50 Each independently is: Hydrogen, deuterium, -CD3, -CD2H, -CDH2, or C1-C 20 alkyl; C1-C replaced by at least one of the following 20 Alkyl groups: deuterium, -CD3, -CD2H, -CDH2, or C1-C 10 Alkyl; or -Si(Q1)(Q2)(Q3), Q1-Q3 are each independent of the following: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or Each of the following is substituted by at least one of the following: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl or phenyl.

2. The organometallic compound of claim 1, wherein Ar 11 -Ar 15 Each independently is: -CD3, -CD2H, or -CDH2; or A group represented by one of formulas 9-1 to 9-39, 10-12 to 10-23, 10-38 to 10-58, 10-67 to 10-69, 10-72, 10-99 to 10-101, or 10-105 to 10-114, R 11 -R 14 R 21 -R 24 R 31 -R 36 R 31a -R 38a R 41 -R 49 and R 50 Each independently is: Hydrogen, deuterium, -CD3, -CD2H, or -CDH2; or Groups represented by one of formulas 9-1 to 9-40 or 9-42: in, In equations 9-1 to 9-40, 9-42, 10-12 to 10-23, 10-38 to 10-58, 10-67 to 10-69, 10-72, 10-99 to 10-101, and 10-105 to 10-114, Indicates the binding site with adjacent atoms.

3. The organometallic compound of claim 1, wherein R 11 -R 14 Each can be independently deuterium, -CD3, -CD2H, -CDH2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, or -Si(Q1)(Q2)(Q3). Q1-Q3 are each independent of the following: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or Each of the following is substituted by at least one of the following: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl or phenyl.

4. The organometallic compound of claim 1, wherein R 21 -R 24 Each can be independently deuterium, -CD3, -CD2H, -CDH2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, or -Si(Q1)(Q2)(Q3). Q1-Q3 are each independent of the following: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; Each of the following is substituted by at least one of the following: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl or phenyl.

5. The organometallic compound of claim 1, wherein the organometallic compound is electrically neutral.

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

8. The organic light-emitting device of claim 7, wherein the emitting layer comprises at least one organometallic compound.

9. The organic light-emitting device of claim 8, wherein the emitting layer further comprises a body in an amount greater than the amount of the organometallic compound in the emitting layer.

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

11. The organic light-emitting device of claim 8, wherein... The first electrode is the anode. The second electrode is the cathode. The organic layer further includes a hole transport region located between the first electrode and the emitter layer, and an electron transport region located between the emitter layer and the second electrode. The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

12. A diagnostic composition comprising an organometallic compound as described in any one of claims 1-6.

Images