Organometallic compound, organic light-emitting device including organometallic compound, and electronic device including organic light-emitting device

Abstract

The present invention relates to organometallic compounds, organic light emitting devices including organometallic compounds, and electronic devices including organic light emitting devices. The organometallic compounds are represented by Formula 1, wherein M is a transition metal, L1and L2are ligands as provided herein, n1and n2are each independently 1 or 2, the sum of n1and n2is 2 or 3, and L1is different from L2. Formula 1 M(L1) n1 (L2) n2 .

Description

[0001] Cross-reference to related applications

[0002] This application claims priority to and all rights arising therefrom of Korean Patent Application No. 10-2020-0060898 filed on May 21, 2020 and Korean Patent Application No. 10-2021-0064010 filed on May 18, 2021, 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 electronic devices including said organic light-emitting devices. 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 structure includes an anode, a cathode, and an organic layer located between the anode and cathode, wherein the organic layer typically includes 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 can recombine in the emitter layer to generate excitons. These excitons transition from an excited state to a ground state, thereby producing light, such as visible light. Summary of the Invention

[0006] One or more aspects provide novel organometallic compounds, organic light-emitting devices comprising at least one of the organometallic compounds, and electronic devices comprising the organic light-emitting devices.

[0007] Other aspects will be set forth in part in the detailed description that follows, and will also be apparent in part from the detailed description, or may be learned by practice of the exemplary embodiments presented in this disclosure.

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

[0009] Formula 1

[0010] M(L1) n1 (L2) n2

[0011] In Equation 1,

[0012] M can be a transition metal.

[0013] L1 can be a ligand represented by Equation 2A.

[0014] L2 can be a ligand represented by equation 2B.

[0015] n1 and n2 can each be 1 or 2 independently. When n1 is 2, the two L1 values ​​can be the same or different from each other, and when n2 is 2, the two L2 values ​​can be the same or different from each other.

[0016] The sum of n1 and n2 can be 2 or 3.

[0017] L1 can be different from L2.

[0018]

[0019] Among them, in equations 2A and 2B,

[0020] Y4 is either C or N.

[0021] X1 is either Si or Ge.

[0022] X 21 For O, S, S(=O), N(Z) 29 ), C(Z) 29 (Z) 30 ), or Si(Z) 29 (Z) 30 ),

[0023] T1-T4 are each independently C, N, carbon atoms bonded to ring CY1, or carbon atoms bonded to M in Formula 1, provided that one of T1-T4 is a carbon atom bonded to M in Formula 1, and the other of T1-T4 that is not bonded to M is a carbon atom bonded to ring CY1.

[0024] T5-T8 are each independently C or N.

[0025] The total number of N atoms in T1-T8 is either 0 or 1.

[0026] CY1 and CY 14 Each independently is C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups,

[0027] Ar2 is a ring CY2 that is either unsubstituted or substituted with at least one Z0, wherein the ring CY2 is an unsaturated C5-C ring. 30 Carbocyclic groups or unsaturated C1-C 30 Heterocyclic groups,

[0028] R 21 -R 23 Each independently constitutes its own unsubstituted or substituted C1-C as follows60 Alkyl or C6-C 60 Aryl 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 20 Alkyl, C3-C 10 cycloalkyl, phenyl, or combinations thereof,

[0029] Z0, Z1, Z2, Z 29 Z 30 and R 11 -R 14 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-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 C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60Heteroaryl thiols, 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), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0030] d2 is an integer from 1 to 6, and when d2 is 2 or greater, at least two Ar2 are either the same as or different from each other.

[0031] a1 and b1 are each independent integers from 0 to 20. When a1 is 2 or greater, at least two Z1s are either the same or different from each other, and when b1 is 2 or greater, at least two Rs are equal. 14 Whether they are the same or different,

[0032] a2 is an integer between 0 and 5, and when a2 is 2 or greater, at least two Z2s are either the same as or different from each other.

[0033] Either condition 1 or condition 2 is satisfied:

[0034] Condition 1

[0035] In Equation 2B, X1 represents Si.

[0036] R in Equation 2B 12 It is neither hydrogen nor methyl, and

[0037] In Equation 2A, T1-T8 are not each N, and

[0038] Condition 2

[0039] In Equation 2B, R 12 It is hydrogen, or R 12 It contains 1 carbon atom.

[0040] R 21 -R 23 At least two of them may be combined with each other to form an unsubstituted or R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0041] At least two of a plurality of Z1s may be optionally combined with each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0042] At least two of a plurality of Z2s may be optionally combined with each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0043] R 12 and R 13 Optionally combined with each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0044] Multiple R 14 At least two of them may be combined with each other to form an unsubstituted or R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0045] Z0, Z1, Z2, Z 29 Z 30 and R 11 -R 14 At least two of them may be combined with each other to form an unsubstituted or R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0046] R 10a By referring to the R provided in this article 14 The description and understanding

[0047] In equations 2A and 2B, * and *' respectively represent the binding sites with M in equation 1, and

[0048] Replacement C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10Cycloalkenyl, substituted C2-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 C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 At least one substituent of the heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group is:

[0049] 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, C1-C 60 alkoxy, or C1-C 60 Alkylthio;

[0050] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, 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, C2-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -N(Q) 11 (Q) 12 ), -Si(Q 13 (Q) 14 (Q) 15 -Ge(Q) 13 (Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 -P(Q) 18 (Q) 19 ), or combinations thereof;

[0051] Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, 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, amido, 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 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-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, C2-C 60 Alkyl heteroaryl, C2-C60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -N(Q) 21 (Q) 22 ), -Si(Q 23 (Q) 24 (Q) 25 -Ge(Q) 23 (Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 -P(Q) 28 (Q) 29 ), or combinations thereof;

[0052] -N(Q 31 (Q) 32 ), -Si(Q 33 (Q) 34 (Q) 35 -Ge(Q) 33 (Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q) 38 (Q) 39 ), or -P(Q 38 (Q) 39 );or

[0053] Any combination of them,

[0054] Among them, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each of the following 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; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 aryl, or combined substituted C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy group; C1-C 60Alkylthio group; C3-C 10 cycloalkyl; C1-C 10 Heterocyclic alkyl; C3-C 10 Cycloalkenyl; C2-C 10 Heterocyclic alkenyl groups; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 aryl, or combined substituted C6-C 60 Aryl; C6-C 60 Aryloxy group; C6-C 60 Arylthio; C1-C 60 heteroaryl; C1-C 60 Heteroaryloxy group; C1-C 60 Heteroaryl thio group; monovalent non-aromatic fused polycyclic group; or monovalent non-aromatic fused heterocyclic group.

[0055] According to one or more embodiments, an organic light-emitting device 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 may include an emitting layer, and wherein the organic layer may include at least one organometallic compound as described herein.

[0056] In one or more embodiments, the at least one organometallic compound is included in the emitter layer of the organic layer. In one or more embodiments, the organometallic compound included in the emitter layer can be used as a dopant.

[0057] According to one or more embodiments, the electronic device includes the organic light-emitting device. Attached Figure Description

[0058] The above and other aspects, features, and advantages of one or more embodiments will become more apparent from the following detailed description taken in conjunction with the accompanying drawings, wherein:

[0059] Figure 1 This is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments. Detailed Implementation

[0060] The embodiments will now be described in detail, examples of which are shown in the accompanying drawings, wherein the same reference numerals always refer to the same elements. In this respect, the embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below only by 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.

[0061] 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 exclude the presence or addition of one or more additional features, regions, integrals, steps, operations, elements, components, and / or sets thereof.

[0062] 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.

[0063] Exemplary embodiments are described herein with reference to cross-sectional views that serve as schematic representations of idealized embodiments. Thus, deviations from the shapes shown in the figures will be anticipated as a result of, for example, manufacturing techniques and / or tolerances. Therefore, the embodiments described herein should not be construed as limited to the specific shapes of the regions illustrated herein, but rather include deviations in shape caused, for example, by manufacturing processes. For example, regions illustrated or described as flat may typically have rough and / or non-linear characteristics. Furthermore, sharp corners in the figures may be rounded. Therefore, the regions illustrated in the figures are schematic in nature, and their shapes are not intended to illustrate the precise shapes of the regions nor to limit the scope of the claims.

[0064] 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.

[0065] Unless otherwise defined, all terms used herein (including technical and scientific terms) shall have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, shall be interpreted as having a meaning consistent with their meaning in the context of the relevant field and in the present disclosure, and shall not be interpreted in an idealized or overly formal sense unless clearly defined herein.

[0066] 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%.

[0067] This article presents organometallic compounds represented by Formula 1:

[0068] Formula 1

[0069] M(L1) n1 (L2) n2

[0070] In Equation 1, M is a transition metal.

[0071] In one or more embodiments, M may be a first row of transition metals, a second row of transition metals, or a third row of transition metals.

[0072] In one or more embodiments, M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0073] In one or more embodiments, M may be Ir, Pt, Os, or Rh.

[0074] In Equation 1, L1 is the ligand represented by Equation 2A, and n1 in Equation 1 represents the number of L1 in Equation 1, and n1 is 1 or 2. When n1 is 2, the two L1 are the same or different from each other.

[0075] In Equation 1, L2 is the ligand represented by Equation 2B, and n2 in Equation 1 represents the number of L2 in Equation 1, and n2 is 1 or 2. When n2 is 2, the two L2 are either the same or different from each other.

[0076]

[0077] Equations 2A and 2B can be understood by referring to the descriptions of Equations 2A and 2B provided in this document.

[0078] In Formula 1, L1 and L2 can be different from each other. That is, the organometallic compound represented by Formula 1 can be a heterojunction complex.

[0079] In one or more embodiments, M can be Ir, n1+n2=3; or M can be Pt, n1+n2=2.

[0080] In one or more embodiments, M can be Ir in Equation 1, and i) n1 can be 1 and n2 can be 2; or ii) n1 can be 2 and n2 can be 1.

[0081] In Equation 2B, Y4 can be C or N.

[0082] In one or more embodiments, Y4 in Formula 2B may be C.

[0083] In Equation 2B, X1 is either Si or Ge.

[0084] In Equation 2A, X 21 For O, S, S(=O), N(Z) 29 ), C(Z) 29 (Z) 30 ), or Si(Z) 29 (Z) 30 Z 29 and Z 30 You can refer to Z provided in this article. 29 and Z 30 The description and understanding.

[0085] In one or more embodiments, X in Formula 2A 21 It can be O or S.

[0086] In Formula 2A, T1-T4 are each independently C, N, carbon atoms bonded to ring CY1, or carbon atoms bonded to M in Formula 1, provided that one of T1-T4 is a carbon atom bonded to M in Formula 1, and the other of T1-T4 that is not bonded to M is a carbon atom bonded to ring CY1, and T5-T8 are each independently C or N.

[0087] The total number of N atoms in T1-T8 in Equation 2A is 0 or 1.

[0088] In equations 2A and 2B, ring CY1 and ring CY 14 Each independently is C5-C 30 Carbocyclic groups or C1-C 30 The heterocyclic group, Ar2 in formula 2A, is an unsubstituted or substituted ring CY2, and the ring CY2 is an unsaturated C5-C ring. 30 Carbocyclic groups or unsaturated C1-C 30 Heterocyclic group. Z0 can be understood by referring to the description of Z0 provided in this article.

[0089] In one or more embodiments, in formulas 2A and 2B, ring CY1 and ring CY 14Each group can independently be a cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentene group, cyclohexene group, cycloheptene group, phenyl group, naphthyl group, anthracene group, phenanthrene group, benzo[9,10]phenanthrene group, pyrene group, Groups, cyclopentadienyl groups, 1,2,3,4-tetrahydronaphthalene groups, thiophene groups, furan groups, borocyclopentadienyl groups, phosphacyclopentadienyl groups, thiophene groups, germanium heterocyclopentadienyl groups, selenophene groups, indole groups, benzoboron heterocyclopentadienyl groups, benzophosphacyclopentadienyl groups, indene groups, benzothiophene groups, benzogermanium heterocyclopentadienyl groups, benzothiophene groups, benzoselenophene groups, benzofuran groups Carbazole group, dibenzoborane heterocyclopentadienyl group, dibenzophosphonocyclopentadienyl group, fluorene group, dibenzothiophene group, dibenzogermanium heterocyclopentadienyl group, dibenzothiophene group, dibenzoselenene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azidoindole group, azidobenzoborane heterocyclopentadienyl group, azidobenzene Azaphosphazene group, azidinium group, azibenzothiophene group, azibenzogermanium aziphazene group, azibenzothiophene group, azibenzoselenene group, azibenzofuran group, azicarbazole group, azidibenzoboron aziphazene group, azidibenzophosphazene group, azifluorene group, azidibenzothiophene group, azidibenzogermanium aziphazene group, azidibenzothiophene 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, 5,6,7,8-tetrahydroquinoline group, adamantyl group, norbornene group, or norbornene group.

[0090] In one or more embodiments, ring CY1 and ring CY 14Each group can be independently 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 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.

[0091] In one or more embodiments, in Formula 2A, cycloCY1 may be a pyridine group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

[0092] In one or more embodiments, in formula 2B, ring CY 14 It can be a phenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenanthrene group, a dibenzothiophene group, a dibenzofuran group, or a pyridine group.

[0093] In one or more embodiments, cycloCY2 may be 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, borocyclopentadienyl groups, phosphacyclopentadienyl groups, thiophene groups, germanium heterocyclopentadienyl groups, selenophene groups, indole groups, benzoboron heterocyclopentadienyl groups, benzophosphacyclopentadienyl groups, indene groups, benzothiophene groups, benzogermanium heterocyclopentadienyl groups, benzothiophene groups, benzoselenophene groups, benzofuran groups Carbazole group, dibenzoborane heterocyclopentadienyl group, dibenzophosphonocyclopentadienyl group, fluorene group, dibenzothiophene group, dibenzogermanium heterocyclopentadienyl group, dibenzothiophene group, dibenzoselenene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azidoindole group, azidobenzoborane heterocyclopentadienyl group, azidobenzene Azaphosphazene group, azidinium group, azibenzothiophene group, azibenzogermanium aziphazene group, azibenzothiophene group, azibenzoselenene group, azibenzofuran group, azicarbazole group, azidibenzoboron aziphazene group, azidibenzophosphazene group, azifluorene group, azidibenzothiophene group, azidibenzogermanium aziphazene group, azidibenzothiophene 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.

[0094] In equation 2B, R 21 -R 23 Each can be independently represented as either C1-C that has not been substituted or has been substituted as follows. 60 Alkyl or C6-C 60 Aryl 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 20 Alkyl, C3-C 10 Cycloalkyl, phenyl, or combinations thereof.

[0095] In one or more embodiments, in formula 2B, R 21 -R 23 Each can be independently identified as either unsubstituted or substituted with the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl. 2-Nonyl, tert-Nonyl, n-Decyl, isodecyl, 2-Decyl, tert-Decyl, phenyl, biphenyl, or naphthyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, 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, C3-C 10 Cycloalkyl, phenyl, or combinations thereof.

[0096] In one or more embodiments, in formula 2B, R 21 -R 23 Each can be independently -CH3, -CH2CH3, -CD3, -CD2H, -CDH2, -CH2CD3, or -CD2CH3.

[0097] In one or more embodiments, in formula 2B, R21 -R 23 They can be the same as each other.

[0098] In one or more embodiments, in formula 2B, R 21 -R 23 At least two of them can be different from each other.

[0099] In equations 2A and 2B, Z0, Z1, Z2, Z 29 Z 30 and R 11 -R 14 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-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 C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 The terms include heteroaryl thio groups, 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), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), wherein Q1-Q9 can be understood by referring to the descriptions of Q1-Q9 provided herein.

[0100] In Equation 2A, d2 represents the quantity of Ar2, and d2 can be an integer from 1 to 6. When d2 is 2 or greater, at least two Ar2 can be the same or different from each other. In one or more embodiments, d2 can be 1, 2, or 3. In one or more embodiments, d2 can be 1 or 2.

[0101] In equations 2A and 2B, a1 and b1 can represent Z1 and R, respectively. 14 The number of Z1s, where a1 and b1 can each be independent integers from 0 to 20. When a1 is 2 or greater, at least two Z1s can be the same or different from each other. When b1 is 2 or greater, at least two R1s can be the same or different from each other. 14 They may be the same or different from each other. In one or more implementations, a1 and b1 may each be an integer from 0 to 10 independently.

[0102] In Equation 2A, a2 represents the quantity of Z2, and a2 can be an integer from 0 to 5. When a2 is 2 or greater, at least two Z2 can be the same or different from each other. In one or more embodiments, a2 can be 0, 1, 2, or 3.

[0103] In one or more embodiments, Z1 in Formula 2A and R in Formula 2B 11 -R 13 Each can be independently:

[0104] Hydrogen, deuterium, -F, or cyano;

[0105] C1-C that has not been replaced or has been replaced as follows 20 Alkyl groups: deuterium, -F, cyano, C3-C 10 cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 cycloalkyl, (C1-C 20 Alkyl)C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, deuterated C1-C 10 Heterocyclic alkyl, fluorinated C1-C 10 Heterocyclic alkyl, (C1-C 20 Alkyl) C1-C 10 Heterocyclic alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C) 20 alkyl)biphenyl, or combinations thereof; or

[0106] Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, phenyl, or biphenyl: deuterium, -F, cyano, C1-C20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C1-C 20 Alkoxy, deuterated C1-C 20 Alkoxy, fluorinated C1-C 20 Alkoxy, C3-C 10 cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 cycloalkyl, (C1-C 20 Alkyl)C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, deuterated C1-C 10 Heterocyclic alkyl, fluorinated C1-C 10 Heterocyclic alkyl, (C1-C 20 Alkyl) C1-C 10 Heterocyclic alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C) 20 Alkyl)biphenyl, or combinations thereof.

[0107] In one or more embodiments, Z1 in Formula 2A and R in Formula 2B 11 -R 13 Each can be independently:

[0108] Hydrogen or deuterium;

[0109] C1-C that has not been replaced or has been replaced as follows 20 Alkyl groups: deuterium, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, (C1-C 20 Alkyl)C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, deuterated C1-C 10 Heterocyclic alkyl, (C1-C 20 Alkyl) C1-C 10 Heterocyclic alkyl, phenyl, deuterated phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, (C1-C) 20 alkyl)biphenyl, or combinations thereof; or

[0110] Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, phenyl, or biphenyl: deuterium, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, C1-C20 Alkoxy, deuterated C1-C 20 Alkoxy, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, (C1-C 20 Alkyl)C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, deuterated C1-C 10 Heterocyclic alkyl, (C1-C 20 Alkyl) C1-C 10 Heterocyclic alkyl, phenyl, deuterated phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, (C1-C) 20 Alkyl)biphenyl, or combinations thereof.

[0111] In one or more embodiments, Z0 and Z2 in Formula 2A and R in Formula 2B 14 Each can be independently:

[0112] Hydrogen, deuterium, -F, or cyano;

[0113] C1-C that has not been replaced or has been replaced as follows 20 Alkyl groups: deuterium, -F, cyano, C3-C 10 cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 cycloalkyl, (C1-C 20 Alkyl)C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, deuterated C1-C 10 Heterocyclic alkyl, fluorinated C1-C 10 Heterocyclic alkyl, (C1-C 20 Alkyl) C1-C 10 Heterocyclic alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C) 20 alkyl)biphenyl, or combinations thereof;

[0114] Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, phenyl, or biphenyl: deuterium, -F, cyano, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C1-C 20 Alkoxy, deuterated C1-C 20 Alkoxy, fluorinated C1-C 20Alkoxy, C3-C 10 cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 cycloalkyl, (C1-C 20 Alkyl)C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, deuterated C1-C 10 Heterocyclic alkyl, fluorinated C1-C 10 Heterocyclic alkyl, (C1-C 20 Alkyl) C1-C 10 Heterocyclic alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C1-C) 20 alkyl)biphenyl, or combinations thereof; or

[0115] -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5).

[0116] In one or more embodiments, in formulas 2A and 2B, Z0, Z1, Z2, Z 29 Z 30 and R 11 -R 14 Each can be independently:

[0117] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio;

[0118] Each of the following C1-C is replaced: 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20 alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof;

[0119] Each of the following substituted compounds, either unsubstituted or substituted with: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C1-C... 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, (phenyl) C1-C 10 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20 alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazole, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl, azacarbazole, azadibenzofuranyl, azadibenzothiophenyl, or combinations thereof; or

[0120] -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0121] Q1-Q9 can be independently defined as follows:

[0122] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0123] Each of the following is either unsubstituted or substituted with: n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof.

[0124] In one or more embodiments, R in formulas 2A and 2B 21 -R 23 Z1, Z2, and R 11 -R 14 Silicon (Si) may not be included. Therefore, electronic devices that include organometallic compounds represented by Formula 1, such as organic light-emitting devices, may have improved output coupling (light extraction, out-coupling) characteristics.

[0125] In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of conditions A, B, and C:

[0126] Condition A

[0127] In Equation 2A, Z1 may not be hydrogen, and a1 may not be 0.

[0128] Condition B

[0129] In Equation 2A, Z2 may not be hydrogen, and a2 may be 0.

[0130] Condition C

[0131] R in Equation 2B 14 It can be non-hydrogen, and b1 can be non-0.

[0132] Organometallic compounds represented by Equation 1 satisfy either condition 1 or condition 2:

[0133] Condition 1

[0134] In equation 2B, X1 represents Si.

[0135] R in Equation 2B 12 Not hydrogen and methyl, and

[0136] In Equation 2A, T1-T8 are not each N.

[0137] Condition 2

[0138] In Equation 2B, R 12 It is hydrogen, or R 12 The number of carbon atoms included can be 1 (for example, R in formula 2B). 12 It can be hydrogen, methyl, or deuterated methyl (e.g., -CH2D, -CHD2, or -CD3)).

[0139] In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy condition 1.

[0140] In one or more embodiments, the organometallic compound represented by Formula 1 satisfies condition 1 and R of Formula 2B 12 The number of carbon atoms included can be 2 or more.

[0141] In one or more embodiments, the organometallic compound represented by Formula 1 satisfies condition 1 and R in Formula 2B 12 Possible forms:

[0142] C2-C 20 Alkyl or C2-C 20 Alkoxy;

[0143] Each is replaced by a methyl or methoxy group as follows: C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 14 Aryl, C1-C 14 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, or combinations thereof;

[0144] Each of the following C2-Cs is replaced: 20 Alkyl or C2-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, C1-C 10 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocyclic alkenyl, C6-C 14 Aryl, C7-C 14 Alkyl aryl, C7-C 14 arylalkyl, C1-C 14heteroaryl, C2-C 14 Alkyl heteroaryl, C2-C 14 Heteroarylalkyl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, or combinations thereof; or

[0145] Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocyclic alkenyl, C6-C 14 Aryl, C1-C 14 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, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 20 Alkyl, C1-C 20 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocyclic alkenyl, C6-C 14 Aryl, C7-C 14 Alkyl aryl, C7-C 14 arylalkyl, C1-C 14 heteroaryl, C2-C 14 Alkyl heteroaryl, C2-C 14 Heteroarylalkyl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, or combinations thereof.

[0146] In one or more embodiments, the organometallic compound represented by Formula 1 satisfies condition 1 and R in Formula 2B 12 Possible forms:

[0147] The methyl or methoxy groups substituted with the following: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20Alkyl)norbornel, (C1-C 20 alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof;

[0148] The methyl or methoxy groups substituted with the following: i) cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20 alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 (i) alkyl) phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof, and (ii) at least one deuterium;

[0149] C2-C that was not replaced or was replaced as follows 20 Alkyl or C2-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 20Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20 alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof; or

[0150] Each of the following substituted compounds, either unsubstituted or substituted with: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C1-C... 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20 alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, azadibenzothiophenyl, or combinations thereof.

[0151] In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy condition 2.

[0152] In one or more embodiments, the organometallic compound represented by Formula 1 can satisfy condition 2 as described herein, X1 in Formula 2B can be Si, and the number of N in T1-T8 in Formula 2A can be 0.

[0153] In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy condition 2 as described herein, X1 in Formula 2B may be Ge, and the total number of N atoms in T1-T8 in Formula 2A may be 0.

[0154] In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy condition 2 as described herein, X1 in Formula 2B may be Si, and the total number of N atoms in T1-T8 in Formula 2A may be 1.

[0155] In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy condition 2 as described herein, X1 in Formula 2B may be Ge, and the total number of N atoms in T1-T8 in Formula 2A may be 1.

[0156] In one or more embodiments, the organometallic compound represented by Formula 1 can satisfy condition 2 as described herein, and R in Formula 2B 12 It may include at least one deuterium.

[0157] In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium, at least one fluorine group (-F), at least one cyano group (-CN), or a combination thereof.

[0158] In one or more embodiments, the organometallic compound represented by Formula 1 may include at least one deuterium.

[0159] In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of conditions (1A), (2A), or (3) to (6); or the organometallic compound represented by Formula 1 may satisfy condition (7):

[0160] Condition(1A)

[0161] In Equation 2A, a1 may not be 0, and at least one of Z1 with a quantity of a1 may include deuterium.

[0162] Condition (2A)

[0163] In formula 2A, a2 may not be 0, and at least one of Z2 in quantity a2 may include deuterium, fluorine group (-F), cyano, or a combination thereof.

[0164] Condition (3)

[0165] In Formula 2A, at least one of the Ar2 groups in the quantity d2 may include deuterium, a fluorine group (-F), a cyano group, or a combination thereof.

[0166] Condition (4)

[0167] In Equation 2B, R 21 -R 23 At least one of them may include deuterium,

[0168] Condition (5)

[0169] In Equation 2B, R 12 It may include at least one deuterium,

[0170] Condition (6)

[0171] In Equation 2B, b1 can be non-zero, and the quantity of R is b1. 14 At least one of them may include deuterium, a fluorine group (-F), a cyano group, or a combination thereof, and

[0172] Condition (7)

[0173] Among them, Z1, Z2, and Ar2 in Equation 2A and R in Equation 2B 11 -R 14 and R 21 -R 23 It can be composed of carbon and hydrogen.

[0174] In one or more embodiments, in formulas 2A and 2B, Z0, Z1, Z2, Z 29 Z 30 and R 11 -R 14Each of these can independently be hydrogen, deuterium, -F, cyano, nitro, -SF5, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -OCH3, -OCDH2, -OCD2H, -OCD3, -SCH3, -SCDH2, -SCD2H, -SCD3, a group represented by any one of formulas 9-1 to 9-39, a group represented by any one of formulas 9-1 to 9-39 wherein at least one hydrogen is replaced by deuterium, a group represented by any one of formulas 9-1 to 9-39 wherein at least one hydrogen is replaced by -F, a group represented by any one of formulas 9-201 to 9-230, a group represented by any one of formulas 9-201 to 9-230 wherein at least one hydrogen is replaced by deuterium, or a group represented by any one of formulas 9-201 to 9-230 wherein at least one hydrogen is replaced by -F. The group represented by any one of formulas 9-201 to 9-230, the group represented by any one of formulas 10-1 to 10-145, the group represented by any one of formulas 10-1 to 10-145 wherein at least one hydrogen is replaced by deuterium, the group represented by any one of formulas 10-1 to 10-145 wherein at least one hydrogen is replaced by -F, the group represented by any one of formulas 10-201 to 10-354, the group represented by any one of formulas 10-201 to 10-354 wherein at least one hydrogen is replaced by deuterium, the group represented by any one of formulas 10-201 to 10-354 wherein at least one hydrogen is replaced by -F, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5), wherein Q3-Q5 can be understood by referring to the description of Q3-Q5 provided herein.

[0175] In one or more embodiments, Z1 in Formula 2A and R in Formula 2B 11 -R 13 Each of these can be independently represented by hydrogen, deuterium, -CH3, -CD3, -CD2H, -CDH2, -OCH3, -OCDH2, -OCD2H, -OCD3, -SCH3, -SCDH2, -SCD2H, -SCD3, a group represented by any one of formulas 9-1 to 9-39, a group represented by any one of formulas 9-201 to 9-230, a group represented by any one of formulas 9-201 to 9-230, a group represented by any one of formulas 10-1 to 10-138 and 10-145, or a group represented by any one of formulas 10-1 to 10-138 and 10-145, where at least one hydrogen is replaced by deuterium.

[0176] In one or more embodiments, Ar2 in Formula 2A may be a group represented by any one of Formulas 10-12 to 10-145, a group represented by any one of Formulas 10-12 to 10-145 in which at least one hydrogen is replaced by deuterium, a group represented by any one of Formulas 10-12 to 10-145 in which at least one hydrogen is replaced by -F, a group represented by any one of Formulas 10-201 to 10-354, a group represented by any one of Formulas 10-201 to 10-354 in which at least one hydrogen is replaced by deuterium, or a group represented by any one of Formulas 10-201 to 10-354 in which at least one hydrogen is replaced by -F.

[0177] In one or more embodiments, R in Formula 2B 12 It can be hydrogen, -CH3, -CH2D, -CHD2 or -CD3.

[0178] In one or more embodiments, R in Formula 2B 12 It can be hydrogen or methyl (-CH3).

[0179] In one or more embodiments, R in Formula 2B 12 It can be -CH2D, -CHD2 or -CD3.

[0180] In one or more embodiments, R in Formula 2B 12 It can be a group represented by any one of formulas 9-1 to 9-39, a group represented by any one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium, a group represented by any one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by -F, a group represented by any one of formulas 9-201 to 9-230, a group represented by any one of formulas 9-201 to 9-230 in which at least one hydrogen is replaced by deuterium, a group represented by any one of formulas 9-201 to 9-230 in which at least one hydrogen is replaced by -F, or a group represented by formulas 10-1 to A group represented by any one of formulas 10-145, a group represented by any one of formulas 10-1 to 10-145 in which at least one hydrogen is replaced by deuterium, a group represented by any one of formulas 10-1 to 10-145 in which at least one hydrogen is replaced by -F, a group represented by any one of formulas 10-201 to 10-354, a group represented by any one of formulas 10-201 to 10-354 in which at least one hydrogen is replaced by deuterium, or a group represented by any one of formulas 10-201 to 10-354 in which at least one hydrogen is replaced by -F.

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189] In formulas 9-1 to 9-39, 9-201 to 9-230, 10-1 to 10-145, and 10-201 to 10-354, * indicates a binding site with an adjacent atom, "Ph" represents phenyl, "TMS" represents trimethylsilyl, "TMG" represents trimethylgermanyl, and "OMe" represents methoxy.

[0190] "A group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium" and "a group represented by one of formulas 9-201 to 9-230 in which at least one hydrogen is replaced by deuterium" can each be, for example, a group represented by one of formulas 9-501 to 9-514 and 9-601 to 9-637:

[0191]

[0192] "A group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by -F" and "a group represented by one of formulas 9-201 to 9-230 in which at least one hydrogen is replaced by -F" can each be, for example, a group represented by one of formulas 9-701 to 9-710:

[0193]

[0194] "A group represented by one of formulas 10-1 to 10-145 in which at least one hydrogen is replaced by deuterium" and "a group represented by one of formulas 10-201 to 10-354 in which at least one hydrogen is replaced by deuterium" can each be, for example, a group represented by one of formulas 10-501 to 10-553:

[0195]

[0196]

[0197] "A group represented by one of formulas 10-1 to 10-145, wherein at least one hydrogen atom is replaced by -F" and "a group represented by one of formulas 10-201 to 10-354, wherein at least one hydrogen atom is replaced by -F" can each be, for example, a group represented by formulas 10-601 to 10-636:

[0198]

[0199] In equations 2A and 2B, i)R 21 -R 23 At least two of them may optionally be combined with each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 (ii) At least two of the plurality of Z1 groups may optionally be combined with each other to form an unsubstituted or R-group. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, iii) at least two of a plurality of Z2 groups may optionally be combined with each other to form an unsubstituted or R-group. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, iv)R 12 and R 13 They may optionally combine with each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, v) multiple R 14 At least two of them may optionally be combined with each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, vi) Z0, Z1, Z2, Z 29 Z 30 and R 11 -R 14 At least two of them may optionally be combined with each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups.

[0200] As used in this article, R 10a You can refer to the R provided in this article 14 The description and understanding.

[0201] In Equations 2A and 2B, * and *' each represent the binding site with M in Equation 1.

[0202] In one or more embodiments, in formula 2A, by The group represented can be one of the groups represented by formulas CY1(1) to CY1(16):

[0203]

[0204] Among them, in equations CY1(1) to CY1(16),

[0205] * indicates the binding site with M in Equation 1, and

[0206] * indicates a binding site with one of T1-T4 in Formula 2A.

[0207] In one or more embodiments, in formula 2A, by The group represented can be one of the groups represented by formulas CY1-1 to CY1-28:

[0208]

[0209]

[0210] Among them, in formulas CY1-1 to CY1-28,

[0211] Z 11 -Z 14 Each can be as described in Z1 provided in this article, where Z 11 -Z 14 Each of them is not hydrogen.

[0212] CY 10a C5-C can be substituted or unsubstituted. 30 The carbocyclic group may or may not be substituted C1-C 30 Heterocyclic groups,

[0213] R 10a It may be the same as described in this article.

[0214] aa can be an integer from 0 to 10.

[0215] * indicates the binding site with M in Equation 1, and

[0216] * indicates a binding site with one of T1-T4 in Formula 2A.

[0217] In one or more embodiments, the ring CY 10a It can be a cyclohexyl group, a norcamphenyl group, a phenyl group, or a naphthalene group.

[0218] In one or more embodiments, in formula 2A, by The group represented may be one of the groups represented by the formula CY1-1, CY1-4, CY1-7, CY1-9, CY1-11, CY1-12, and CY1-14 to CY1-24.

[0219] In one or more embodiments, in formula 2A, by The group represented can be one of the groups represented by formulas CY2-1 to CY2-6:

[0220]

[0221] Among them, in equations CY2-1 to CY2-6,

[0222] T1-T8 can each be independently C or N; the number of N in T3-T8 in equations CY2-1 and CY2-6 can be 0 or 1; the number of N in T1, T2, T5, T6, T7, and T8 in equations CY2-2 and CY2-5 can be 0 or 1; and the number of N in T1, T4, T5, T6, T7, and T8 in equations CY2-3 and CY2-4 can be 0 or 1.

[0223] X 21 It may be the same as described in this article.

[0224] * indicates the binding site with ring CY1 in formula 2A, and

[0225] *' indicates the binding site with M in Formula 1.

[0226] In one or more embodiments, the organometallic compound represented by formula 1, wherein formula 2A contains the compound of formula 1. The group represented can be one of the groups represented by formulas CY2-1 to CY2-6.

[0227] a) X1 in Equation 2B can be Si, and R in Equation 2B can be Si. 12 It may not be hydrogen or methyl, and the number of N in T1-T8 of formulas CY2-1 to CY2-6 may be 0.

[0228] b) In equation 2B, X1 can be Si or Ge, and R in equation 2B can be Si or Ge. 12 It can be hydrogen, methyl, or deuterated methyl, and the number of N in T1-T8 of formulas CY2-1 to CY2-6 can be 0.

[0229] c) In equation 2B, X1 can be Si or Ge, and R in equation 2B can be Si or Ge. 12 It can be hydrogen, methyl, or deuterated methyl, and the number of N in T3-T8 in formulas CY2-1 and CY2-6 can be 1.

[0230] d) In equation 2B, X1 can be Si or Ge, and R in equation 2B 12 It can be hydrogen, methyl, or deuterated methyl, and the number of N in T1, T2, T5, T6, T7, and T8 in formulas CY2-2 and CY2-5 can be 1, or

[0231] e) In equation 2B, X1 can be Si or Ge, and R in equation 2B can be Si or Ge. 12 It can be hydrogen, methyl, or deuterated methyl, and the number of N in T1, T4, T5, T6, T7 and T8 in formulas CY2-3 and CY2-4 can be 1.

[0232] In one or more embodiments, in formula 2A, by The group represented can be one of the groups represented by formulas CY2(1) to CY2(6):

[0233]

[0234] In equations CY2(1) to CY2(6),

[0235] T 21 It can be N, C(Z) 21 ), or C(Ar 21 ), T 22 It can be N, C(Z) 22 ), or C(Ar 22 ), T 23 It can be N, C(Z) 23 ), or C(Ar 23 ), T 24 It can be N, C(Z) 24 ), or C(Ar 24 ), T 25 It can be N, C(Z) 25 ), or C(Ar 25 ), T 26 It can be N, C(Z) 26 ), or C(Ar 26 ), T 27 It can be N, C(Z) 27 ), or C(Ar 27 ), and T 28 It can be N, C(Z) 28 ), or C(Ar 28 ),

[0236] In equations CY2-1 and CY2-6, the number of N in T3-T8 can be 0 or 1; in equations CY2-2 and CY2-5, the number of N in T1, T2, T5, T6, T7, and T8 can be 0 or 1; and in equations CY2-3 and CY2-4, the number of N in T1, T4, T5, T6, T7, and T8 can be 0 or 1.

[0237] X 21 It may be the same as described in this article.

[0238] Z 21 -Z 28 Each can be the same as the description of Z2 provided in this article.

[0239] Ar 21 -Ar 28 Each can be the same as the description of Ar2 provided in this article.

[0240] Formulas CY2-1 and CY2-6 may include Ar 23 -Ar 28 At least one of the formulas CY2-2 and CY2-5 may include Ar 21 Ar 22 Ar 25 Ar 26 Ar 27 And Ar 28 At least one of them, and formulas CY2-3 and CY2-4 may include Ar 21 Ar 24 Ar 25 Ar 26 Ar 27 And Ar 28 At least one of them,

[0241] * indicates the binding site with ring CY1 in formula 2A, and

[0242] *' indicates the binding site with M in Formula 1.

[0243] In one or more embodiments, in formula 2A, by The group represented may be one of the groups represented by formulas CY2(1) to CY2(6), and at least one of conditions 1-1 to 1-8 may be satisfied:

[0244] Condition 1-1

[0245] Among them, T in equations CY2(1) to CY2(6) 28 It can be C(Ar) 28 ),

[0246] Conditions 1-2

[0247] Among them, T in equations CY2(1) to CY2(6) 27 It can be C(Ar) 27 ),

[0248] Conditions 1-3

[0249] Among them, T in equations CY2(1) to CY2(6) 26 It can be C(Ar) 26 ),

[0250] Conditions 1-4

[0251] Among them, T in equations CY2(1) to CY2(6) 25 It can be C(Ar) 25 ),

[0252] Conditions 1-5

[0253] Among them, T in equations CY2(1), CY2(3), CY2(4), and CY2(6) 24 It can be C(Ar) 24 ),

[0254] Conditions 1-6

[0255] Among them, T in equations CY2(1) and CY2(6) 23 It can be C(Ar) 23 ),

[0256] Conditions 1-7

[0257] Among them, T in equations CY2(2) and CY2(5) 22 It can be C(Ar) 22 ),

[0258] Conditions 1-8

[0259] Among them, T in equations CY2(2) to CY2(5) 21 It can be C(Ar) 21 ).

[0260] In one or more embodiments, in formula 2A, by The group represented may be one of the groups represented by formulas CY2(1) to CY2(6), and at least one of conditions 2-1 to 2-8 may be satisfied:

[0261] Condition 2-1

[0262] Among them, T in equations CY2(1) to CY2(6) 28 It can be C(Z) 28 ), and Z 28 It may not be hydrogen.

[0263] Condition 2-2

[0264] Among them, T in equations CY2(1) to CY2(6) 27 It can be C(Z) 27 ), and Z 27 It may not be hydrogen.

[0265] Condition 2-3

[0266] Among them, T in equations CY2(1) to CY2(6) 26 It can be C(Z) 26 ), and Z 26 It may not be hydrogen.

[0267] Conditions 2-4

[0268] Among them, T in equations CY2(1) to CY2(6) 25 It can be C(Z) 25 ), and Z 25 It may not be hydrogen.

[0269] Conditions 2-5

[0270] Among them, T in equations CY2(1), CY2(3), CY2(4), and CY2(6) 24 It can be C(Z) 24 ), and Z 24 It may not be hydrogen.

[0271] Conditions 2-6

[0272] Among them, T in equations CY2(1) and CY2(6) 23 It can be C(Z) 23 ), and Z 23 It may not be hydrogen.

[0273] Conditions 2-7

[0274] Among them, T in equations CY2(2) and CY2(5) 22 It can be C(Z) 22 ), and Z 22 It may not be hydrogen.

[0275] Conditions 2-8

[0276] Among them, T in equations CY2(2) to CY2(5) 21 It can be C(Z) 21 ), and Z 21 It may not be hydrogen.

[0277] In one or more embodiments, in formula 2A, by The group represented can be one of the groups represented by formulas CY2(1) to CY2(6), and one of conditions 3-1 to 3-9 can be satisfied:

[0278] Condition 3-1

[0279] T in equations CY2(1) to CY2(6) 21 -T 28 Each can be different from N.

[0280] Condition 3-2

[0281] T in equations CY2(1) to CY2(6) 28 It can be N,

[0282] Condition 3-3

[0283] T in equations CY2(1) to CY2(6) 27 It can be N,

[0284] Conditions 3-4

[0285] T in equations CY2(1) to CY2(6) 26 It can be N,

[0286] Conditions 3-5

[0287] T in equations CY2(1) to CY2(6) 25 It can be N,

[0288] Conditions 3-6

[0289] Among them, T in equations CY2(1), CY2(3), CY2(4), and CY2(6) 24 It can be N,

[0290] Conditions 3-7

[0291] T in equations CY2(1) and CY2(6) 23 It can be N,

[0292] Conditions 3-8

[0293] T in equations CY2(2) and CY2(5) 22 It can be N,

[0294] Conditions 3-9

[0295] T in equations CY2(2) to CY2(5) 21 It can be N

[0296] In one or more embodiments, the group represented by formula CY2(1) may be a group represented by one of formulas CY2(1)-1 to CY2(1)-4, the group represented by formula CY2(2) may be a group represented by one of formulas CY2(2)-1 to CY2(2)-4, the group represented by formula CY2(3) may be a group represented by one of formulas CY2(3)-1 to CY2(3)-3, the group represented by formula CY2(4) may be a group represented by one of formulas CY2(4)-1 to CY2(4)-3, the group represented by formula CY2(5) may be a group represented by one of formulas CY2(5)-1 to CY2(5)-4, and the group represented by formula CY2(6) may be a group represented by one of formulas CY2(6)-1 to CY2(6)-4.

[0297]

[0298]

[0299] Among them, in equations CY2(1)-1 to CY2(1)-4, CY2(2)-1 to CY2(2)-4, CY2(3)-1 to CY2(3)-3, CY2(4)-1 to CY2(4)-3, CY2(5)-1 to CY2(5)-4, and CY2(6)-1 to CY2(6)-4,

[0300] T 21 -T 28 X 21 、*”、 and*’ can be obtained by referring to T in equations CY2(1) to CY2(6) provided in this article. 21 -T 28 X 21 Understanding the descriptions of 、,*, and*'

[0301] CY 20a C5-C can be substituted or unsubstituted. 30 The carbocyclic group may or may not be substituted C1-C 30 Heterocyclic groups,

[0302] R 10a It may be the same as described in this article, and

[0303] aa can be an integer from 0 to 10.

[0304] In one or more embodiments, the ring CY 20a It can be a cyclohexyl group, a norcamphenyl group, a phenyl group, or a naphthalene group.

[0305] In one or more embodiments, in formula 2A, by The group represented may be one of the following: CY2-1-1 to CY2-1-65, CY2-2-1 to CY2-2-65, CY2-3-1 to CY2-3-65, CY2-4-1 to CY2-4-65, CY2-5-1 to CY2-5-65, and CY2-6-1 to CY2-6-65.

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316] Among them, in formulas CY2-1-1 to CY2-1-65, CY2-2-1 to CY2-2-65, CY2-3-1 to CY2-3-65, CY2-4-1 to CY2-4-65, CY2-5-1 to CY2-5-65, and CY2-6-1 to CY2-6-65,

[0317] X 21 It may be the same as described in this article.

[0318] Z 21 -Z 28 Each can be the same as the description of Z2 provided in this article, where Z 21 -Z 28 Each of them is not hydrogen.

[0319] Ar 21 -Ar 28 Each can be the same as the description of Ar2 provided in this article.

[0320] * indicates the binding site with ring CY1 in formula 2A, and

[0321] *' indicates the binding site with M in Formula 1.

[0322] In one or more embodiments, in formula 2B, by The group represented can be one of the groups represented by formulas CY14-1 to CY14-64:

[0323]

[0324]

[0325] Among them, in formulas CY14-1 to CY14-64,

[0326] X 14a It can be O, S, N, C, or Si.

[0327] * indicates the binding site with the carbon atom in the adjacent pyridine ring in Formula 2B, and

[0328] *' indicates the binding site with M in Formula 1.

[0329] Carbon and X in formulas CY14-1 to CY14-64 14a Each can be either unreplaced or R provided in this article. 14 replace.

[0330] In one or more embodiments, in formula 2B, by The group represented can be one of the groups represented by formulas CY14(1) to CY14(63):

[0331]

[0332]

[0333]

[0334] Among them, in equations CY14(1) to CY14(63),

[0335] R 14a -R 14d Each can be compared with the information about R provided in this article. 14 The description is the same, where R 14a -R 14d Each of them is not hydrogen.

[0336] X 14 It can be C(R1)(R2), N(R1), O, S, or Si(R1)(R2).

[0337] R1-R8 can each be compared with the information provided in this article regarding R. 14 The same as described.

[0338] * indicates the binding site with the carbon atom in the adjacent pyridine ring in Formula 2B, and

[0339] *' indicates the binding site with M in Formula 1.

[0340] In one or more embodiments, the number of silicon (Si) atoms in the organometallic compound represented by Formula 1 may be 1 or 2.

[0341] In one or more embodiments, the organometallic compound may be one of compounds 1 to 5140:

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471] In the organometallic compound represented by Formula 1, L1 can be a ligand represented by Formula 2A, n1 (i.e., the number of L1) can be 1 or 2, L2 can be a ligand represented by Formula 2B, n2 (i.e., the number of L2) can be 1 or 2, and L1 and L2 can be different from each other. That is, the organometallic compound can be a heterojunction complex that must include at least one ligand represented by Formula 2A and at least one ligand represented by Formula 2B as ligands bound to the metal M.

[0472] In Equation 1, from *-X1(R) 21 (R) 22 (R) 23 The group represented by ) can bind to the 5' position of the pyridine ring in the ligand represented by Formula 2B (see Formula 2B). Therefore, organometallic compounds including ligands represented by Formula 2B can exhibit excellent heat resistance and resistance to degradation. Consequently, electronic devices including said organometallic compounds, such as organic light-emitting devices, can exhibit excellent stability and long lifespan during manufacturing, storage, and / or operation.

[0473] Ar2 in Equation 2A of Equation 1 can be an unsubstituted or substituted ring CY2, and the ring CY2 can be an unsaturated C5-C ring. 30 Carbocyclic groups or unsaturated C1-C 30 The heterocyclic group, and d2 (i.e., the number of Ar2 groups) can be an integer from 1 to 6. Therefore, the organometallic compound represented by Formula 1 can have improved optical orientation properties, and the organometallic compound represented by Formula 1 can have a relatively narrow half-width (FWHM) of the emission spectrum or electroluminescence spectrum, and therefore, electronic devices including the organometallic compound, such as organic light-emitting devices, can have improved emission efficiency.

[0474] Furthermore, the number of N in T1-T8 of Formula 1 can be 0 or 1. Therefore, the organometallic compound represented by Formula 1 can have stable highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels, which leads to improved lifetime of electronic devices including the organometallic compound, such as organic light-emitting devices.

[0475] Density functional theory (DFT) was used to calculate the highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), lowest excited singlet (S1), and lowest excited triplet (T1) energy levels of the selected organometallic compounds represented by Equation 1, in electron volts (eV), using the Gaussian 09 program with molecular structure optimization at the B3LYP level. The results are shown in Table 1.

[0476] Table 1

[0477]

[0478] Referring to the results in Table 1, it was found that the organometallic compounds represented by Formula 1 have suitable electrical properties for use as dopants in electronic devices, such as organic light-emitting devices.

[0479] The method for synthesizing the organometallic compound represented by Formula 1 will be apparent to those skilled in the art by referring to the synthesis examples provided herein.

[0480] 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 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 and including an emission layer, wherein the organic layer may include at least one organometallic compound represented by Formula 1.

[0481] Since the organic light-emitting device has an organic layer comprising an organometallic compound represented by Formula 1, the organic light-emitting device can have high external quantum efficiency and high lifetime characteristics.

[0482] Organometallic compounds represented by Formula 1 can be used in electrode pairs of 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 be used as a dopant, and the emitting layer may further include a host (i.e., the amount of the organometallic compound represented by Formula 1 may be less than the amount of the host). The emitting layer, for example, can emit green or blue light.

[0483] As used herein, the statement “(organic layer) comprises at least one organometallic compound” can be interpreted as meaning “(organic layer) may comprise one organometallic compound of Formula 1 or two or more different organometallic compounds of Formula 1”.

[0484] For example, compound 1 may be included solely as an organometallic compound in the organic layer. 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 as organometallic compounds in the organic layer. In this embodiment, compounds 1 and 2 may both be included in the same layer (e.g., both compounds 1 and 2 may be included in the emitting layer).

[0485] 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.

[0486] 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 between the first electrode and the emitting layer and an electron transport region 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.

[0487] As used herein, the term "organic layer" refers to one or more layers 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.

[0488] Figure 1 A schematic cross-sectional view illustrating an organic light-emitting device 10 according to one or more embodiments is shown below. Referring 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.

[0489] A substrate may be disposed below the first electrode 11 or above 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 possessing excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water repellency.

[0490] 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 for forming the first electrode 11 can include a material with a high work function for easy hole injection. The first electrode 11 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. The material for forming the first electrode 11 can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 can be a metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc.

[0491] The first electrode 11 may have a single-layer structure or a multi-layer structure including multiple layers. In one or more embodiments, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO.

[0492] The organic layer 15 may be on the first electrode 11.

[0493] The organic layer 15 may include a hole transport region, an emitter layer, and an electron transport region.

[0494] The hole transport region may be located between the first electrode 11 and the emitter layer.

[0495] 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.

[0496] 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.

[0497] 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.

[0498] 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, at a temperature of about 10- 8 To-John 10- 3 Under a vacuum level within the Torr range, and at approximately 0.01 angstroms per second ( / second) - approximately Deposition rates in the range of / second are carried out, although 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.

[0499] 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 about 200°C to promote solvent removal after spin coating, although the conditions may vary depending on the compound used as the hole injection material and the structure and thermal properties of the desired hole injection layer.

[0500] 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.

[0501] The hole transport region may include 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, compounds represented by formula 202, or any combination thereof:

[0502]

[0503] Formula 201

[0504]

[0505] Formula 202

[0506]

[0507] In Equation 201, Ar 101 and Ar 102 Each can be independently an unsubstituted or substituted phenylene, cyclopentadienylene, indenylene, naphthylene, or phenylene. alkyl, heptadeneyl, acenaphthene, fluoreneyl, phenentheneyl, anthraceneyl, fluoreneyl, benzo[9,10]phenentheneyl, pyreneyl, phenentheneyl alkyl, tetraphenyl, phenyl -1, -perylene, -pentaphenylene, or combinations thereof: 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 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C2-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, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups.

[0508] 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.

[0509] In equations 201 and 202, R 101 -R 108 R 111 -R 119 and R 121 -R 124 Each can be independently:

[0510] 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);

[0511] Each of the following C1-Cs was not replaced or was replaced as follows 10 Alkyl or C1-C10 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, or combinations thereof; or

[0512] Each of the following groups—either unsubstituted or substituted with: 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, C1-C 10 Alkoxy groups, or combinations thereof.

[0513] In Equation 201, R 109 It can be phenyl, naphthyl, anthracene, or pyridyl, respectively, either unsubstituted or substituted with the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, anthraceneyl, pyridyl, or combinations thereof.

[0514] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A:

[0515] Formula 201A

[0516]

[0517] In Equation 201A, R 101 R 111 R 112 and R 109 You can refer to the R provided in this article respectively. 101 R 111 R 112 and R 109 The description and understanding.

[0518] In one or more embodiments, the hole transport region may include one or more compounds HT1 to HT20:

[0519]

[0520]

[0521] The thickness of the hole transport region can be approximately 100 angstroms. -about and in one or more embodiments -about Within the range. When the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, the thickness of the hole injection layer can be approximately -about and in one or more embodiments -about Within a certain range, and the thickness of the hole transport layer can be approximately [missing information]. -about and in one or more embodiments -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.

[0522] In addition to the aforementioned materials, 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 substantially uniformly or non-uniformly dispersed in the hole transport region.

[0523] The charge-generating material may include, for example, a p-doper. The p-doper may be a quinone derivative, a metal oxide, a cyano-containing compound, or any combination thereof. In one or more embodiments, the p-doper may be a quinone derivative such as tetracyanoquinone dimethylane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethylane (F4-TCNQ), or F6-TCNNQ; a metal oxide such as tungsten oxide or molybdenum oxide; a cyano-containing compound such as compound HT-D1; or any combination thereof.

[0524]

[0525] The hole transport region may further include a buffer layer.

[0526] 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.

[0527] When the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may include the material used to form the hole transport region, the host material described herein, or a combination thereof. In one or more embodiments, when the hole transport region includes an electron blocking layer, mCP, compounds H-H1, etc., as described herein, may be used to form the electron blocking layer.

[0528] 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 can be substantially similar to those used to form the hole injection layer, although the conditions may vary depending on the compound used.

[0529] The emitter layer may include a host and a dopant, and the dopant may include an organometallic compound represented by Formula 1 as described herein.

[0530] The main body may include TPBi, TBADN, ADN (also known as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, compound H52, compound H-H1, compound H-E43, or combinations thereof:

[0531]

[0532] 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 / or 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 changed.

[0533] When the emitter layer comprises the body and the 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 body.

[0534] 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.

[0535] Next, an electron transmission region can be formed on the emission layer.

[0536] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0537] 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. The electron transport layer may have a multilayer structure or a single-layer structure comprising two or more different materials.

[0538] The conditions for forming the hole blocking layer, electron transport layer, and electron injection layer can be inferred based on the conditions for forming the hole injection layer.

[0539] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, BCP, Bphen, BAlq, or any combination thereof:

[0540]

[0541] The thickness of the hole-blocking layer can be approximately -about and in one or more embodiments -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.

[0542] The electron transport layer may include BCP, Bphen, TPBi, Alq3, BAlq, TAZ, NTAZ, or combinations thereof:

[0543]

[0544] In one or more embodiments, the electron transport layer may include one or more compounds ET1 to ET25:

[0545]

[0546]

[0547]

[0548] 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.

[0549] In addition to the materials described above, the electron transport layer may further include a material containing metal.

[0550] The metal-containing material may include Li complexes. The Li complexes may include, for example, compounds ET-D1 or ET-D2.

[0551]

[0552] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 19.

[0553] The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or combinations thereof.

[0554] The thickness of the electron injection layer can be approximately -about For example, about -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.

[0555] The second electrode 19 may be located 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 any combination thereof. Examples of materials used to form the second electrode 19 may include lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). 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.

[0556] The above text has already referred to Figure 1 Organic light-emitting device 10 has been described, but the implementation is not limited thereto.

[0557] According to another aspect of the embodiment, the electronic device may include the organic light-emitting device. Therefore, an electronic device including the organic light-emitting device can be provided. The electronic device may include, for example, a display, a lighting device, a sensor, etc.

[0558] According to another embodiment, the diagnostic composition may include at least one organometallic compound represented by Formula 1.

[0559] 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.

[0560] The diagnostic composition can be used in a variety of ways, such as in diagnostic kits, diagnostic reagents, biosensors, or biomarkers.

[0561] As used in this article, the term "C1-C" 60 "Alkyl" refers to a straight-chain or branched monovalent group of a saturated aliphatic hydrocarbon having 1-60 carbon atoms, and as used herein, "C1-C..."60 "alkylene" refers to a compound with C1-C2 atoms. 60 Divalent groups with the same structure as alkyl groups.

[0562] As used in this article, C1-C 60 Alkyl, C1-C 20 Alkyl, and / or C1-C 10 Examples of alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert ... Decyl or tert-decyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, or any combination thereof. In one or more embodiments, formula 9-33 may be a branched C6 alkyl group. Formula 9-33 may be a tert-butyl group substituted with two methyl groups.

[0563] 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, propoxy, butoxy, and pentoxy.

[0564] 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 bond structure. 60 Divalent groups with the same structure as alkenyl groups.

[0565] 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... 60 "Alynyl group" refers to a group with a C2-C group.60 Divalent groups with the same structure as alkynyl groups.

[0566] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monovalent cyclic hydrocarbon group having 3-10 carbon atoms. 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.

[0567] C3-C as used in this article 10 Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norcamphenyl (bicyclo[2.2.1]heptyl) group, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl.

[0568] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated cyclic group having 1-10 carbon atoms and at least one heteroatom of N, O, P, Si, S, Se, Ge, or B as a cyclic atom. The term "C1-C" is used herein. 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with the same structure as heterocyclic alkyl groups.

[0569] As used in this article, C1-C 10 Examples of heterocyclic alkyl groups may include silylcyclopentyl, silylcyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, or tetrahydrothiophenyl.

[0570] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent cyclic group having 3-10 carbon atoms and at least one carbon-carbon double bond in its ring, wherein the molecular structure as a whole 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.

[0571] As used in this article, the term "C2-C" 10 "Heterocyclic alkenyl" refers to a monovalent cyclic group whose ring includes at least one heteroatom of N, O, P, Si, S, Se, Ge, or B as a cyclic atom, 2-10 carbon atoms, and at least one carbon-carbon double bond, wherein the molecular structure as a whole is non-aromatic. (C2-C) 10Examples of heterocyclic alkenyl groups include 2,3-dihydrofuranyl and 2,3-dihydrothiophenyl. As used herein, the term "C2-C..." 10 "Heterocyclic alkenyl" refers to a group with a C2-C... 10 Divalent groups with the same structure as heterocyclic alkenyl groups.

[0572] 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.

[0573] As used in this article, the term "C7-C" 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.

[0574] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having the following heterocyclic aromatic system: it has at least one heteroatom of N, O, P, Si, S, Se, Ge, or B as a cyclic atom and 1-60 carbon atoms. The term "C1-C" is used herein. 60 "Hypo-heteroaryl" refers to a divalent group having the following heterocyclic aromatic system: it has at least one heteroatom of N, O, P, Si, S, Se, Ge, or B as a cyclic atom and 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.

[0575] As used in this article, the term "C2-C" 59 "alkyl heteroaryl" refers to an alkyl group formed by at least one C1-C2 group. 59 Alkyl-substituted C1-C 59heteroaryl. As used in this text, the term "C2-C" is used in conjunction with... 60 "Heteroarylalkyl" refers to an alkyl group consisting of at least one C1-C2 group. 59 heteroaryl-substituted C1-C 59 alkyl.

[0576] As used in this article, the term "C6-C" 60 "Aryloxy group" is composed of -OA 102 (where A) 102 For C6-C 60 Aryl) is indicated. As used herein, the term "C6-C" is... 60 "Arylthio" is composed of -SA 103 (where A) 103 For C6-C 60 Aryl) is indicated. As used herein, the term "C1-C" is... 60 "alkylthio" is composed of -SA 104 (where A) 104 For C1-C 60 Alkyl group is used to indicate this.

[0577] 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 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.

[0578] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group having two or more fused rings and having heteroatoms and carbon atoms (e.g., the number of carbon atoms can range from 1 to 60) selected from N, O, P, Si, S, Se, Ge, and B as cyclic atoms, wherein the molecular structure as a whole is nonaromatic. Examples of 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 a structure substantially the same as that of a monovalent nonaromatic fused heterocyclic group.

[0579] 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) 30 The carbocyclic group can be a monocyclic or polycyclic group. The term "(unsubstituted or with at least one R)" is used. 10 (or at least one Z0) substituted C5-C 30 "Carbocyclic groups" may include (each unsubstituted or with at least one R)10 (or at least one Z0-substituted) adamantyl group, norbornene group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group (norbornene group), bicyclo[2.2.2]octyl group, cyclopentyl group, cyclohexyl group, cyclohexene group, phenyl group, naphthyl group, anthracene group, phenanthrene group, benzo[9,10]phenanthrene group, pyrene group, Groups, 1,2,3,4-tetrahydronaphthalene groups, cyclopentadienyl groups, or fluorene groups.

[0580] 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, Se, Ge, and B as the cyclic atom. C1-C 30 Heterocyclic groups can be monocyclic or polycyclic. "(Unsubstituted or substituted with at least one R)" 10 (or at least one Z0) substituted C1-C 30 Examples of "heterocyclic groups" may include (each unsubstituted or substituted by at least one R) 10 (Or at least one Z0-substituted) thiophene group, furan group, pyrrole group, thiophene group, borocyclopentadienyl group, phosphacyclopentadienyl group, selenophene group, germanium heterocyclopentadienyl group, benzothiophene group, benzofuran group, indole group, benzothiophene group, benzoboron heterocyclopentadienyl group, benzophosphacyclopentadienyl group, benzoselenophene group, benzogermanium heterocyclopentadienyl group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzothiophene group, dibenzoboron heterocyclopentadienyl group, dibenzophosphacyclopentadienyl group, dibenzoselenophene group, dibenzogermanium heterocyclopentadienyl group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, aza... Indene group, azirbenzothiophene group, azirbenzoboranecyclopentadiene group, azirbenzophosphacyclopentadiene group, azirbenzoselenophene group, azirbenzogeranecyclopentadiene group, azirdibenzothiophene group, azirdibenzofuran group, azircarbazole group, azirfluorene group, azirdibenzothiophene group, azirdibenzoboranecyclopentadiene group, azirdibenzophosphacyclopentadiene group, azirdibenzoselenophene group, azirdibenzogeranecyclopentadiene group, azirdibenzothiophene 5-oxide group, azir-9H-fluorene-9-one group, azirdibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazolinine group, phenanthrene-rhein group, pyrazole group, imidazole group, triazole group azole group, iso- azole group, thiazole group, isothiazole group, Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo[] azole group, benzothiazole group, benzo[] The diazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, or 5,6,7,8-tetrahydroquinoline group.

[0581] As used in this article, “C5-C” 30 "Carbon ring group" and "C1-C" 30 Examples of "heterocyclic groups" include i) a first ring, ii) a second ring, iii) a fused ring in which at least two first rings are fused, iv) a fused ring in which at least two second rings are fused, or v) a fused ring in which at least one first ring and at least one second ring are fused.

[0582] The first ring may be a cyclopentyl group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a thiophene group, a borocyclopentadiene group, a phosphacyclopentadiene group, a germanium heterocyclopentadiene group, or a selenophene group. azole group, iso- azole group, diazole group, Triazole group, thiazole group, isothiazole group, thiadiazole group, thiatriazole group, pyrazole group, imidazole group, triazole group, tetraazole group, azathiophene group, diazathiophene group, or triazathiophene group, and

[0583] 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.

[0584] As used in this article, the term "fluorinated C1-C" 60 Alkyl (or fluorinated C1-C) 20 Alkyl groups, etc., and fluorinated C3-C groups. 10 "cycloalkyl", "fluorinated C1-C" 10 "Heterocyclic alkyl" and "fluorophenyl" refer to C1-C1 alkyl groups, respectively, that are substituted with at least one fluorine group (-F). 60 Alkyl (or C1-C) 20 Alkyl groups, etc., C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl groups and phenyl groups. Examples of "fluoroC1 alkyl (i.e., fluoromethyl)" may include -CF3, -CF2H, and -CFH2. "Fluorocyclic C1-C 60 Alkyl (or fluorinated C1-C) 20 Alkyl groups, etc., and fluorinated C3-C groups.10 "cycloalkyl", "fluorinated C1-C" 10 "Heterocyclic alkyl" or "fluorophenyl" can be: i) fully fluorinated C1-C 60 Alkyl (or fully fluorinated C1-C) 20 Alkyl groups, etc., and fully fluorinated C3-C groups 10 cycloalkyl, fully fluorinated C1-C 10 Heterocyclic alkyl groups, or fully fluorinated phenyl groups, wherein all hydrogen atoms are replaced by fluorine groups; or ii) partially fluorinated C1-C... 60 Alkyl (or partially fluorinated C1-C) 20 Alkyl groups, etc., and partially fluorinated C3-C groups 10 Cycloalkyl, partially fluorinated C1-C 10 Heterocyclic alkyl or partially fluorinated phenyl groups, wherein some of the hydrogen atoms are replaced by fluorine groups.

[0585] As used in this article, "deuterated C1-C" 60 Alkyl (or deuterated C1-C) 20 Alkyl groups, etc., and deuterated C3-C 10 "Cycloalkyl", "Deuterated C1-C" 10 "Heterocyclic alkyl" and "deuterated phenyl" can be C1-C1 groups, each of which is substituted with at least one deuterium. 60 Alkyl (or C1-C) 20 Alkyl groups, etc., C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl groups and phenyl groups. Examples of "deuterated C1 alkyl groups (i.e., deuterated methyl groups)" may include -CD3, -CD2H, and -CDH2. "Deuterated C3-C..." 10 Examples of "cycloalkyl" may include formula 10-501. "Deuterated C1-C..." 60 Alkyl (or deuterated C1-C) 20 Alkyl groups, etc., and deuterated C3-C 10 "Cycloalkyl", "Deuterated C1-C" 10 "Heterocyclic alkyl" or "deuterated phenyl" can be: i) fully deuterated C1-C 60 Alkyl (or fully deuterated C1-C) 20 Alkyl groups, etc., and fully deuterated C3-C 10 Cycloalkyl, fully deuterated C1-C 10 Heterocyclic alkyl groups, or fully deuterated phenyl groups, wherein all hydrogen atoms are replaced by deuterium atoms; or ii) partially deuterated C1-C 60 Alkyl (or partially deuterated C1-C) 20 Alkyl groups, etc.), and partially deuterated C3-C 10 cycloalkyl, partially deuterated C1-C 10Heterocyclic alkyl groups, or partially deuterated phenyl groups, wherein some of the hydrogen atoms are replaced by deuterium atoms.

[0586] As used in this article, the term "(C1-C" is similar to the term "(C1-C)" 20 "alkyl)'X' group" refers to a group surrounded by at least one C1-C1 group. 20 Alkyl-substituted 'X' groups. For example, as used herein, the term "(C1-C1)" 20 Alkyl)C3-C 10 "Cycloalkyl" refers to a compound formed by at least one C1-C2 group. 20 Alkyl-substituted C3-C 10 Cycloalkyl, and as used herein, “(C1-C 20 "alkyl)phenyl" refers to a compound formed by at least one C1-C2 bond. 20 Alkyl-substituted phenyl groups. Examples of (C1 alkyl)phenyl groups may include tolyl.

[0587] In this specification, "azaindole group, azabenzoboranecyclopentadienyl group, azabenzophosphacyclopentadienyl group, azaindene group, azabenzothiophene group, azabenzogermanium cyclopentadienyl group, azabenzothiophene group, azabenzoselenene group, azabenzofuran group, azacarbazole group, azadibenzoboranecyclopentadienyl group, azadibenzophosphacyclopentadienyl group, azafluorene group, azadibenzothiophene group, azadibenzogermanium cyclopentadienyl group, azadibenzothiophene group, azadibenzoselenene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, and azadibenzothiophene 5,5-di Each "oxide group" refers to a heterocycle in which at least one cyclic carbon atom is replaced by a nitrogen atom and which has the same skeleton as "indole group, benzoborane heterocyclopentadienyl group, benzophosphonocyclopentadienyl group, indene group, benzothiophene group, benzogermanium heterocyclopentadienyl group, benzothiophene group, benzoselenene group, benzofuran group, carbazole group, dibenzoborane heterocyclopentadienyl group, dibenzophosphonocyclopentadienyl group, fluorene group, dibenzothiophene group, dibenzogermanium heterocyclopentadienyl group, dibenzothiophene group, dibenzoselenene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, and dibenzothiophene 5,5-dioxide group".

[0588] Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C1-C 60Alkylthio, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C2-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 At least one substituent of the heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group can each independently be:

[0589] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;

[0590] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -N(Q) 11 (Q) 12 ), -Si(Q 13 (Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 -P(Q) 18 (Q) 19 ), or combinations thereof;

[0591] Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, carboxylic acid 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 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-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, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -N(Q) 21 (Q) 22 ), -Si(Q 23 (Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 -P(Q) 28 (Q) 29 ), or combinations thereof;

[0592] -N(Q 31 (Q) 32 ), -Si(Q 33 (Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q) 38 (Q) 39 ), or -P(Q 38 (Q) 39 );or

[0593] Any combination thereof.

[0594] In this specification, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each of these can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidine; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphate group or its salt; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 aryl, or combined substituted C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy group; C1-C 60 Alkylthio group; C3-C 10cycloalkyl; C1-C 10 Heterocyclic alkyl; C3-C 10 Cycloalkenyl; C2-C 10 Heterocyclic alkenyl groups; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 aryl, or combined substituted C6-C 60 Aryl; C6-C 60 Aryloxy group; C6-C 60 Arylthio; C1-C 60 heteroaryl; C1-C 60 Heteroaryloxy group; C1-C 60 Heteroaryl thio group; monovalent non-aromatic fused polycyclic group; or monovalent non-aromatic fused heterocyclic group.

[0595] For example, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each can be independently:

[0596] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0597] Each of the following is either unsubstituted or substituted with: n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or any combination thereof.

[0598] The compounds and organic light-emitting devices according to one or more embodiments will be described in further 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 that, based on molar equivalents, the amount of B used is the same as the amount of A used.

[0599] Example

[0600] Synthesis Example 1 (Compound 65)

[0601]

[0602] Synthesis of Compound 65A

[0603] 7.9 g (27.8 mmol) of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine and 4.4 g (12.6 mmol) of iridium chloride hydrate were mixed with 120 mL of ethoxyethanol and 40 mL of deionized (DI) water. The mixture was then stirred under reflux for 24 hours and then cooled 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 7.6 g of compound 65A (yield: 76%).

[0604] Synthesis of Compound 65B

[0605] 3.3 g (2.1 mmol) of compound 65A was mixed with 90 mL of dichloromethane, and a solution of 1.1 g (4.1 mmol) of silver trifluoromethanesulfonate (AgOTf) dissolved in 30 mL of methanol was added. The mixture was then stirred at room temperature for 18 hours while using aluminum foil to block light. The result was filtered through diatomaceous earth to remove the solid formed therefrom and then filtered under reduced pressure to obtain the solid (compound 65B). This solid was used in subsequent reactions without any further purification.

[0606] Synthesis of Compound 65

[0607] 4.0 g (4.1 mmol) of compound 65B and 1.7 g (4.5 mmol) of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine were mixed with 40 mL of ethanol and stirred under reflux for 18 hours, followed by cooling. The solvent was removed from the resulting mixture under reduced pressure to obtain a solid, which was subjected to column chromatography (eluent: dichloromethane (MC) and hexane) to obtain 1.8 g of compound 65 (yield: 39%). The obtained compound was confirmed by analysis using mass spectrometry (high resolution mass spectrometry with matrix-assisted laser desorption / ionization, HRMS (MALDI)) and high performance liquid chromatography (HPLC).

[0608] HRMS (MALDI): For C 63 H 70 Calculated value of IrN3OSi2: m / z 1133.4687, measured value: 1133.4681

[0609] Synthesis Example 2 (Compound 206)

[0610]

[0611] Synthesis of compound 206A

[0612] Compound 206A (yield: 72%) was obtained in substantially the same manner as in the synthesis of compound 65A in Synthetic Example 1, except that 4-neopentyl-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0613] Synthesis of compound 206B

[0614] Compound 206B was obtained in substantially the same manner as in the synthesis of compound 65B in Synthetic Example 1, except that compound 206A was used instead of compound 65A. The resulting compound 206B was used in subsequent reactions without any further purification.

[0615] Synthesis of Compound 206

[0616] Compound 206 (yield: 33%) was obtained in substantially the same manner as in the synthesis of compound 65 in Example 1, except that compound 65B was used instead of compound 206B, and 4-neopentyl-2-(8-phenyldibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0617] HRMS (MALDI): For C 66 H 76 Calculated value of IrN3OSi2: m / z 1175.5156, measured value: 1175.5162

[0618] Synthesis Example 3 (Compound 363)

[0619]

[0620] Synthesis of Compound 363A

[0621] Compound 363A (yield: 81%) was obtained in substantially the same manner as in the synthesis of compound 65A in Synthetic Example 1, except that 2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0622] Synthesis of compound 363B

[0623] Compound 363B was obtained in substantially the same manner as in the synthesis of compound 65B in Synthetic Example 1, except that compound 363A was used instead of compound 65A. The resulting compound 363B was used in subsequent reactions without any further purification.

[0624] Synthesis of Compound 363

[0625] Compound 363 (yield: 29%) was obtained in substantially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that compound 65B was used instead of compound 363B, and 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine was used instead of 2-(7-fluorophenyl)dibenzo[b,d]furan-4-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0626] HRMS (MALDI): For C 54 H 51 Calculated value of FIrN3OSi2: m / z 1025.3184, measured value: 1025.3189

[0627] Synthesis Example 4 (Compound 556)

[0628]

[0629] Compound 556 (yield: 36%) was obtained in substantially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that compound 65B was replaced with compound 206B, and 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine was replaced with 5-(methyl-d3)-4-neopentyl-2-(8-phenyldibenzo[b,d]furan-2-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0630] HRMS (MALDI): For C 67 H 75 Calculated value of D3IrN3OSi2: m / z 1192.5501, measured value: 1192.5496

[0631] Synthesis Example 5 (Compound 749)

[0632]

[0633] Compound 749 (yield: 27%) was obtained in substantially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that 4-(cyclohexylmethyl)-2-(7-phenyldibenzo[b,d]thiophene-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0634] HRMS (MALDI): For C 66 H 74 Calculated value of IrN3SSi2: m / z 1189.4771, measured value: 1189.4763

[0635] Synthesis Example 6 (Compound 2350)

[0636]

[0637] Synthesis of Compound 2350A

[0638] Compound 2350A (yield: 88%) was obtained in substantially the same manner as in the synthesis of compound 65A in Synthetic Example 1, except that 4-(methyl-d3)-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine (yield: 88%).

[0639] Synthesis of Compound 2350B

[0640] Compound 2350B was obtained in substantially the same manner as in the synthesis of compound 65B in Synthetic Example 1, except that compound 2350A was used instead of compound 65A. The resulting compound 2350B was used in subsequent reactions without any further purification.

[0641] Synthesis of Compound 2350

[0642] 2.1 g of compound 2350 (yield: 45%) was obtained in substantially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that compound 65B was replaced with compound 2350B, and 2-(7-phenyldibenzo[b,d]furan-4-yl)-4-(phenylmethyl-d2)pyridine was replaced with 2-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0643] HRMS (MALDI): For C 60 H 48Calculated value of D8IrN3OSi2: m / z 1091.4093, measured value: 1091.4090

[0644] Synthesis Example 7 (Compound 2508)

[0645]

[0646] Synthesis of compound 2508A

[0647] Compound 2508A (yield: 67%) was obtained in substantially the same manner as in the synthesis of compound 65A in Synthetic Example 1, except that 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 2-(2-fluoro-4-(methyl-d3)phenyl)-4-(phenylmethyl-d2)-5-(trimethylsilyl)pyridine.

[0648] Synthesis of compound 2508B

[0649] Compound 2508B was obtained in substantially the same manner as in the synthesis of compound 65B in Synthetic Example 1, except that compound 2508A was used instead of compound 65A. The resulting compound 2508B was used in subsequent reactions without further purification.

[0650] Synthesis of Compound 2508

[0651] 1.3 g of compound 2508 (yield: 26%) was obtained in substantially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that compound 65B was replaced with compound 2508B, and 4-(2,2-dimethylpropyl-1,1-d2)-2-(7-(4-(methyl-d3)phenyl)dibenzo[b,d]furan-4-yl)pyridine was replaced with isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0652] HRMS (MALDI): For C 73 H 57 D 15 Calculated value of F2IrN3OSi2: m / z 1308.5753, measured value: 1308.5760

[0653] Synthesis Example 8 (Compound 2566)

[0654]

[0655] Synthesis of Compound 2566A

[0656] Compound 2566A (yield: 83%) was obtained in substantially the same manner as in the synthesis of compound 65A in Synthetic Example 1, except that 2-(4-(methyl-d3)phenyl)-4-(propyl-2-yl-2-d)-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0657] Synthesis of Compound 2566B

[0658] Compound 2566B was obtained in substantially the same manner as in the synthesis of compound 65B in Synthetic Example 1, except that compound 2566A was used instead of compound 65A. The resulting compound 2566B was used in subsequent reactions without any further purification.

[0659] Synthesis of Compound 2566

[0660] Compound 2566 (yield: 34%) was obtained in substantially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that compound 65B was replaced with compound 2566B, and 4-(2,2-dimethylpropyl-1,1-d2)-2-(7-(4-fluorophenyl)dibenzo[b,d]furan-4-yl)pyridine was replaced with 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0661] HRMS (MALDI): For C 64 H 61 D 10 Calculated value of FIrN3OSi2: m / z 1175.5377, measured value: 1175.5383

[0662] Synthesis Example 9 (Compound 2579)

[0663]

[0664] Synthesis of Compound 2579A

[0665] Compound 2579A (yield: 84%) was obtained in substantially the same manner as in the synthesis of compound 65A in Synthetic Example 1, except that 2-([1,1'-biphenyl]-3-yl)-4-(propyl-2-yl-2-d)-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0666] Synthesis of Compound 2579B

[0667] Compound 2579B was obtained in substantially the same manner as in the synthesis of compound 65B in Synthetic Example 1, except that compound 2579A was used instead of compound 65A. The resulting compound 2579B was used in subsequent reactions without any further purification.

[0668] Synthesis of Compound 2579

[0669] 1.1 g of compound 2579 (yield: 25%) was obtained in substantially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that compound 65B was replaced with compound 2579B, and 4-(cyclopentylmethyl-d2)-2-(7-(2,6-dimethylphenyl)dibenzo[b,d]furan-4-yl)pyridine was replaced with 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0670] HRMS (MALDI): For C 77 H 76 Calculated value of D4IrN3OSi2: m / z 1315.5720, measured value: 1315.5711

[0671] Synthesis Example 10 (Compound 2758)

[0672]

[0673] Synthesis of Compound 2758A

[0674] Compound 2758A (yield: 72%) was obtained in substantially the same manner as in the synthesis of compound 65A in Synthetic Example 1, except that 4-(methyl-d3)-2-phenyl-5-(trimethylgermanyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0675] Synthesis of Compound 2758B

[0676] Compound 2758B was obtained in substantially the same manner as in the synthesis of compound 65B in Synthetic Example 1, except that compound 2758A was used instead of compound 65A. The resulting compound 2758B was used in subsequent reactions without any further purification.

[0677] Synthesis of Compound 2758

[0678] Compound 2758 (yield: 37%) was obtained in substantially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that compound 65B was replaced with compound 2758B, and 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine was replaced with 5-(methyl-d3)-4-phenyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0679] HRMS (MALDI): For C 60 H 47 Calculated value of D9Ge2IrN3O: m / z 1184.3041, measured value: 1184.3033

[0680] Synthesis Example 11 (Compound 485)

[0681]

[0682] Compound 485 (yield: 27%) was obtained in essentially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that 2-(1,7-diphenyldibenzo[b,d]furan-4-yl)-4-isobutylpyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0683] HRMS (MALDI): For C 69 H 74 Calculated value of IrN3OSi2: m / z 1209.5000, measured value: 1209.4992

[0684] Synthesis Example 12 (Compound 487)

[0685]

[0686] Compound 487 (yield: 32%) was obtained in substantially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that 2-(7-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-4-yl)-4-isopropylpyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0687] HRMS (MALDI): For C 68 H 72Calculated value of IrN3OSi2: m / z 1195.4843, measured value: 1195.4840

[0688] Synthesis Example 13 (Compound 1703)

[0689]

[0690] Synthesis of Compound 1703A

[0691] Compound 1703A (yield: 65%) was obtained in substantially the same manner as in the synthesis of compound 65A in Synthetic Example 1, except that 2-phenyl-5-(trimethylgermanyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0692] Synthesis of compound 1703B

[0693] Compound 1703B was obtained in substantially the same manner as in the synthesis of compound 65B in Synthetic Example 1, except that compound 1703A was used instead of compound 65A. The resulting compound 1703B was used in subsequent reactions without any further purification.

[0694] Synthesis of Compound 1703

[0695] 2.1 g of compound 1703 (yield: 45%) was obtained in substantially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that compound 65B was replaced with compound 1703B, and 4-isopropyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine was replaced with 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0696] HRMS (MALDI): For C 54 H 52 Calculated value of Ge₂IrN₃O: m / z 1099.2163, measured value: 1099.2156

[0697] Synthesis Example 14 (Compound 2866)

[0698]

[0699] Synthesis of Compound 2866A

[0700] Compound 2866A (yield: 72%) was obtained in substantially the same manner as in the synthesis of compound 65A in Synthetic Example 1, except that 4-neopentyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0701] Synthesis of Compound 2866B

[0702] Compound 2866B was obtained in substantially the same manner as in the synthesis of compound 65B in Synthetic Example 1, except that compound 2866A was used instead of compound 65A. The resulting compound 2866B was used in subsequent reactions without further purification.

[0703] Synthesis of Compound 2866

[0704] Compound 2866 (yield: 24%) was obtained in substantially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that compound 65B was replaced with compound 2866B, and 4-neopentyl-2-phenyl-5-(trimethylsilyl)pyridine was replaced with 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0705] HRMS (MALDI): For C 75 H 74 Calculated value of IrN3O2Si: m / z 1269.5180, measured value: 1269.5188

[0706] Comparative Example 1 (Compound A1)

[0707]

[0708] Compound A1 (yield: 42%) was obtained in substantially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that compound 65B was replaced with compound 363B, and 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine was replaced with 2-(dibenzo[b,d]furan-4-yl)methylpyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0709] HRMS (MALDI): For C 46 H 44 Calculated value of IrN3OSi2: m / z 903.2652, measured value: 903.2645

[0710] Comparative Example 2 (Compound A2)

[0711]

[0712] Synthesis of compound A2A

[0713] Compound A2A (yield: 86%) was obtained in substantially the same manner as in the synthesis of compound 65A in Synthetic Example 1, except that 4-methyl-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0714] Synthesis of compound A2B

[0715] Compound A2B was obtained in substantially the same manner as in the synthesis of compound 65B in Synthetic Example 1, except that compound A2A was used instead of compound 65A. The resulting compound A2B was used in subsequent reactions without further purification.

[0716] Synthesis of compound A2

[0717] Compound A2 (yield: 41%) was obtained in substantially the same manner as in the synthesis of compound 65 in Synthetic Example 1, except that compound A2B was used instead of compound 65B, and 2-(dibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The resulting compound was confirmed by mass spectrometry and HPLC analysis.

[0718] HRMS (MALDI): For C 47 H 46 Calculated value of IrN3OSi2: m / z 917.2809, measured value: 917.2801

[0719] Example 1

[0720] The ITO anode on the patterned glass substrate was cut to dimensions of 50 mm × 50 mm × 0.5 mm, ultrasonically treated with isopropanol and deionized water for 5 minutes each, and cleaned by exposure to ultraviolet light and ozone for 30 minutes. The resulting glass substrate was then mounted on a vacuum deposition apparatus.

[0721] Compounds HT3 and F6-TCNNQ were co-deposited on the anode under vacuum at a weight ratio of 98:2 to form a structure with... A hole injection layer of a certain thickness is formed, and compound HT3 is vacuum-deposited onto the hole injection layer to form a hole injection layer with a thickness of [missing information]. A hole transport layer of a certain thickness is formed, and compound H-H1 is vacuum deposited on the hole transport layer to form a hole transport layer with a certain thickness. An electron blocking layer of a certain thickness.

[0722] Subsequently, compounds H-H1, H-E43, and 65 (dopant) were co-deposited on the electron blocking layer in a weight ratio of 57:38:5 to form a layer with... The thickness of the emission layer.

[0723] Then, compounds ET3 and ET-D1 were co-deposited on the emitter layer at a volume ratio of 50:50 to form a structure with... An electron transport layer of a certain thickness is formed. ET-D1 is vacuum-deposited onto this electron transport layer to form a layer with... An electron-injected layer of a certain thickness is formed. Al is deposited on the electron-injected layer to form a layer with... A cathode of a certain thickness is used to complete the fabrication of organic light-emitting devices.

[0724]

[0725] Examples 2-14 and Comparative Examples A1 and A2

[0726] The organic light-emitting device was fabricated in essentially the same manner as in Example 1, except that the compounds shown in Table 2 were used instead of compound 65 as dopants in the formation of the emitting layer.

[0727] Evaluation Example 1: Evaluation of the characteristics of organic light-emitting devices

[0728] The maximum external quantum efficiency (Max EQE, %) and lifetime (LT) of the organic light-emitting devices fabricated in Examples 1-14 and Comparative Examples A1 and A2 were evaluated. 97 The results are shown in Table 2. A Keithley 2400 ammeter / voltmeter and a Minolta Cs-1000A luminometer were used in the evaluation. Lifetime (T) 97 This refers to the organic light-emitting device's energy density of 16,000 candela per square meter (cd / m²). 2 The time (hr) required for the initial brightness (or nits) to decrease to 97% and expressed as a relative value (%).

[0729] Table 2

[0730]

[0731]

[0732]

[0733] Referring to the results in Table 2, it was found that the organic light-emitting devices of Examples 1-14 have improved external quantum efficiency and lifetime compared with the organic light-emitting devices of Comparative Examples A1 and A2.

[0734] As provided in the preceding detailed description and embodiments, the organometallic compounds can possess excellent electrical properties, and therefore, electronic devices comprising at least one organometallic compound, such as organic light-emitting devices, can exhibit improved external quantum efficiency (EQE) and excellent lifetime characteristics. Thus, by using the at least one organometallic compound, organic light-emitting devices with superior qualities and electronic devices comprising the organic light-emitting devices can be realized.

[0735] It should be understood that one or more exemplary embodiments described herein are to be considered only 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 in further detail 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 1: Formula 1 M(L1) n1 (L2) n2 in, In Equation 1, M is Ir, L1 is the ligand represented by Equation 2A. L2 is the ligand represented by equation 2B. n1 and n2 are each independently 1 or 2. When n1 is 2, the two L1s are either the same or different, and when n2 is 2, the two L2s are either the same or different. The sum of n1 and n2 is 3. L1 is different from L2. Formula 2A Formula 2B Among them, in equations 2A and 2B, Y4 is C, X1 is either Si or Ge. X 21 For O, S, or N (Z) 29 ), T1-T4 are each independently C, N, a carbon atom bonded to ring CY1, or a carbon atom bonded to M in Formula 1, provided that one of T1-T4 is a carbon atom bonded to M in Formula 1, and the other of T1-T4 not bonded to M is a carbon atom bonded to ring CY1. T5-T8 are each independently C or N. The total number of N atoms in T1-T8 is either 0 or 1. Cycle CY1 is a pyridine group, pyrimidine group, pyrazine group, or pyridazine group. CY 14 It is a phenyl group. Ar2 is an unsubstituted or substituted cycloCY2 ring, wherein the cycloCY2 ring is a phenyl group, naphthyl group, anthracene group, phenanthrene group, cyclopentadienyl group, 1,2,3,4-tetrahydronaphthyl group, indene group, or fluorene group. R 21 -R 23 Each of the following is independently represented as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodexyl, sec-decyl, tert-decyl, phenyl, biphenyl, or naphthyl: deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, C3-C 10 cycloalkyl, phenyl, or combinations thereof, Z0, Z1, Z2, and R 11 -R 14 Each independently is: Hydrogen, deuterium, -F, cyano, C1-C 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio; Each of the following C1-C is replaced: 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, or combinations thereof; Each of the following substituted groups—either unsubstituted or substituted with: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, (C1-C) 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, or anthracene: deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 Alkyl, (phenyl) C1-C 10 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, or combinations thereof; or -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), Q3-Q5 are each independent of the following: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or Each of the following is either unsubstituted or substituted with: n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof, Z 29 for: Hydrogen, deuterium, C1-C 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio; or Each of the following C1-C is replaced: 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -CD3, -CD2H, -CDH2, or C1-C 10 alkyl, d2 is an integer from 1 to 6, and when d2 is 2 or greater, at least two Ar2 are either the same as or different from each other. a1 and b1 are each independent integers from 0 to 10. When a1 is 2 or greater, at least two Z1s are either the same or different from each other, and when b1 is 2 or greater, at least two Rs are equal. 14 Whether they are the same or different, a2 is an integer between 0 and 5, and when a2 is 2 or greater, at least two Z2s are either the same as or different from each other. Either condition 1 or condition 2 is satisfied: Condition 1 In equation 2B, X1 represents Si. R in Equation 2B 12 It is neither hydrogen nor methyl, and In Equation 2A, T1-T8 are not each N, and Condition 2 In Equation 2B, R 12 It is hydrogen, or R 12 The number of carbon atoms included is 1, and In Equations 2A and 2B, * and *' each represent the binding site with M in Equation 1.

2. The organometallic compound of claim 1, wherein... n1 is 1 and n2 is 2; or n1 is 2 and n2 is 1.

3. The organometallic compound of claim 1, wherein X in formula 2A 21 It can be O or S.

4. The organometallic compound of claim 1, wherein d2 in formula 2A is 1 or 2.

5. The organometallic compound of claim 1, wherein Z1 in formula 2A and R in formula 2B 11 -R 13 Each independently is: Hydrogen or deuterium; C1-C that has not been replaced or has been replaced as follows 20 Alkyl groups: deuterium, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, (C1-C) 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, or combinations thereof; or Each of the following substituted groups—either unsubstituted or substituted with: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, or biphenyl: deuterium, -F, cyano, C1-C— 20 Alkyl, -CD3, -CD2H, -CDH2, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, or combinations thereof.

6. The organometallic compound of claim 1, wherein Z0 and Z2 in formula 2A and R in formula 2B 14 Each independently is: Hydrogen, deuterium, -F, or cyano; C1-C that has not been replaced or has been replaced as follows 20 Alkyl groups: deuterium, -F, cyano, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, (C1-C) 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, or combinations thereof; Each of the following substituted groups—either unsubstituted or substituted with: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, or biphenyl: deuterium, -F, cyano, C1-C— 20 Alkyl, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, or combinations thereof; or -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5).

7. The organometallic compound of claim 1, wherein the organometallic compound satisfies at least one of conditions A, B, and C: Condition A In Equation 2A, Z1 is not hydrogen, and a1 is not 0. Condition B In equation 2A, Z2 is not hydrogen, and a2 is not 0, and Condition C R in Equation 2B 14 It is not hydrogen, and b1 is not 0.

8. The organometallic compound of claim 1, wherein the organometallic compound represented by formula 1 satisfies condition 1, and R in formula 2B 12 It contains 2 or more carbon atoms.

9. The organometallic compound of claim 1, wherein the organometallic compound represented by formula 1 satisfies condition 2.

10. The organometallic compound of claim 1, wherein the organometallic compound comprises at least one deuterium, at least one fluorine group (-F), at least one cyano group (-CN), or a combination thereof.

11. The organometallic compound of claim 1, wherein at least one of condition (1A), condition (2A), or (3) to (6) is satisfied, or condition (7) is satisfied: Condition(1A) in, In equation 2A, a1 is not 0, and at least one of Z1 with a quantity of a1 includes deuterium. Condition (2A) In formula 2A, a2 is not 0, and at least one of Z2 in quantity a2 includes deuterium, a fluorine group (-F), a cyano group, or a combination thereof. Condition (3) In formula 2A, at least one of the Ar2 groups in the quantity d2 includes deuterium, a fluorine group (-F), a cyano group, or a combination thereof. Condition (4) In Equation 2B, R 21 -R 23 At least one of them includes deuterium, Condition (5) In Equation 2B, R 12 Including at least one deuterium, Condition (6) In Equation 2B, b1 is not 0, and the quantity of R is b1. 14 At least one of them includes deuterium, a fluorine group (-F), a cyano group, or a combination thereof, and Condition (7) Among them, Z1, Z2, and Ar2 in Equation 2A and R in Equation 2B 11 -R 14 and R 21 -R 23 It is composed of carbon and hydrogen.

12. The organometallic compound of claim 1, wherein the compound in formula 2A is composed of... The group represented is one of the groups represented by formulas CY1-1 to CY1-16: in, In equations CY1-1 to CY1-16, Z 11 -Z 14 Each as described in claim 1 with respect to Z1, wherein Z 11 -Z 14 Each is not hydrogen. * indicates the binding site with M in Equation 1, and * indicates a binding site with one of T1-T4 in Formula 2A.

13. The organometallic compound of claim 1, wherein the compound in formula 2A is composed of... The group represented is one of the groups represented by formulas CY2-1 to CY2-6: in, In equations CY2-1 to CY2-6, T1-T8 are each independently C or N. The total number of N atoms in T3-T8 of formulas CY2-1 and CY2-6 is either 0 or 1. In formulas CY2-2 and CY2-5, the total number of N atoms in T1, T2, T5, T6, T7, and T8 is either 0 or 1. In formulas CY2-3 and CY2-4, the total number of N atoms in T1, T4, T5, T6, T7, and T8 is either 0 or 1. X 21 As described in claim 1, * indicates the binding site with ring CY1 in equation 2A, and *' indicates the binding site with M in Equation 1.

14. The organometallic compound of claim 1, wherein in formula 2B, by The group represented is one of the groups represented by formulas CY14(1) to CY14(16): in, In equations CY14(1) to CY14(16), R 14a -R 14d Each of them is related to R in claim 1 14 The description is the same, where R 14a -R 14d Each is not hydrogen. * indicates the binding site with the carbon atom in the adjacent pyridine ring in Formula 2B, and *' indicates the binding site with M in Equation 1.

15. Organic light-emitting devices, including: First electrode; Second electrode; as well as The organic layer located between the first electrode and the second electrode, The organic layer mentioned above includes an emission layer, and The organic layer comprises at least one organometallic compound as described in any one of claims 1-14.

16. The organic light-emitting device of claim 15, 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.

17. The organic light-emitting device of claim 15, wherein the emitting layer comprises the organometallic compound.

18. The organic light-emitting device of claim 17, wherein the emitting layer further comprises a body, and The amount of the main component in the emitter layer is greater than the amount of the organometallic compound in the emitter layer.

19. An electronic device, including an organic light-emitting device as claimed in any one of claims 15-18.

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