Organometal compound, organic light emitting device including organometal compound, and electronic

Abstract

Provided are an organometallic compound represented by Formula 1: wherein M1 is a transition metal, Ln1 is a ligand represented by Formula 1A and Ln2 is a ligand represented by Formula 1B, and other groups and various variables are as described in the detailed description, an organic light-emitting device including the organometallic compound, and an electronic device including the organic light-emitting device. Formula 1M1 (Ln1) n1 (Ln2) n2

Description

[0001] Cross-reference to related applications

[0002] This application is based on and claims priority to Korean Patent Application No. 10-2024-0136794 filed on October 8, 2024 and Korean Patent Application No. 10-2025-0131127 filed on September 12, 2025, both filed with the Korean Intellectual Property Office, and all the 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 with excellent characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed. In addition, OLEDs can produce full-color images.

[0005] In this example, the organic light-emitting device includes an anode, a cathode, and an organic layer disposed between the anode and cathode, including an emission layer. A hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode. Holes supplied from the anode move towards the emission layer through the hole transport region, and electrons supplied from the cathode move towards the emission layer through the electron transport region. Holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to the ground state, thereby producing light. Summary of the Invention

[0006] The invention provides novel organometallic compounds, organic light-emitting devices comprising said organometallic compounds, and electronic devices comprising said organic light-emitting devices.

[0007] Other aspects will be set forth in part in the description which follows, and in part will be apparent from the description, or may be learned through practice of the exemplary embodiments presented herein.

[0008] According to one aspect, organometallic compounds represented by Formula 1 are provided:

[0009] Formula 1

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

[0011] In Equation 1,

[0012] M1 can be a transition metal.

[0013] Ln1 can be a ligand represented by Equation 1A.

[0014] Ln2 can be a ligand represented by Equation 1B.

[0015] n1 can be 1 or 2.

[0016] n2 can be 1 or 2.

[0017]

[0018] Among them, in equations 1A and 1B,

[0019] CY1 and CY2 can each be independently C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups,

[0020] X1 can be C, CH, or N, and X2 can be C, CH, or N.

[0021] Y1 can be O, S, Se, C(R3)(R4), or N(R3).

[0022] Y2 can be C(R5) or N.

[0023] Z1 can be -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3).

[0024] a1 can be 1, 2, 3, or 4.

[0025] R1 to R5, R 10 R 20 R 31 To R 34 and R 41 To R 47 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 C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9),

[0026] Two or more R 10 They can optionally combine with each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,

[0027] Two or more R 20 They can optionally combine with each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,

[0028] R1 to R5, R 10 R 20 R 31 To R 34 and R 41 To R 47 Two or more adjacent C5-C molecules may optionally combine with each other to form substituted or unsubstituted C5-C molecules. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,

[0029] b10 and b20 can each independently be 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0030] * and *' each represent the binding site with M1.

[0031] Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 heteroaryl, 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 may be:

[0032] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy

[0033] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q)15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 ), or a combination thereof,

[0034] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups,

[0035] Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 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, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 ), or a combination thereof, or

[0036] -Si(Q 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 ), or -P(=O)(Q 38 (Q) 39 ),and

[0037] Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

[0038] According to another aspect, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer may include at least one organometallic compound represented by Formula 1. The at least one organometallic compound represented by Formula 1 may be included in the emission layer and may act as a dopant.

[0039] According to another aspect, an electronic device including the organic light-emitting device is provided. Attached Figure Description

[0040] By combination Figure 1 The above and other aspects, features and advantages of some embodiments of this disclosure will become clearer from the following description. Figure 1 This is a schematic cross-sectional view of an organic light-emitting device according to an embodiment. Detailed Implementation

[0041] Various embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the specification. In this respect, the embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, embodiments are described below only with reference to the accompanying drawings to illustrate aspects. As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one” when preceding or following a list of elements modify the entire list of elements and do not modify any individual element of that list. It will be further understood that the terms “comprising” or “including” when 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 other features, regions, integrals, steps, operations, elements, components, and / or collections thereof.

[0042] 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 one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the specific quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations relative to the stated value, or within ±10%, ±5%, or ±3%.

[0043] Organometallic compounds according to one or more embodiments can be represented by Formula 1:

[0044] Formula 1

[0045] M1(Ln1) n1 (Ln2) n2

[0046] In Equation 1, M1 can be a transition metal.

[0047] For example, M1 can be a transition metal in the first row, the second row, or the third row of the periodic table.

[0048] In the implementation, M1 may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0049] In the implementation, M1 can be Ir, Pt, Os, or Rh.

[0050] In the implementation, M1 can be Ir.

[0051] In Equation 1, n1 can be 1 or 2, and n2 can be 1 or 2.

[0052] In the implementation, the sum of n1 and n2 can be 2 or 3.

[0053] In the implementation, M1 can be Ir, and the sum of n1 and n2 can be 3.

[0054] In the implementation, M1 can be Pt, and the sum of n1 and n2 can be 2.

[0055] In the implementation, M1 can be Ir, n1 can be 2, and n2 can be 1.

[0056] In Equation 1, Ln1 can be a ligand represented by Equation 1A:

[0057] Formula 1A

[0058]

[0059] In Equation 1A, X1 can be C, CH, or N, and X2 can be C, CH, or N.

[0060] In the implementation, X1 can be N.

[0061] In the implementation, X2 can be C.

[0062] In Equation 1A, CY1 and CY2 can each be independently C5-C. 30Carbocyclic groups or C1-C 30 Heterocyclic groups.

[0063] In the implementation, CY1 and CY2 can each independently be i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused together, iv) a fused ring in which two or more second rings are fused together, or v) a fused ring in which one or more first rings and one or more second rings are fused together.

[0064] The first ring can be a cyclopentyl group, a cyclopentadienyl group, a furan group, a thiophene group, a pyrrole group, a thiophene group, an indole group, a benzofuran group, a benzothiophene group, an indole group, a benzothiophene group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxtriazole group, an isoxtriazole group, a thiazole group, an isothiazole group, a thiazolidinyl group, an isothiazole group, an isothiazole group, an isothiazole group, an isothiazole group, an isothiazole group, a pyrazole group, an imidazole group, a triazole group, a tetraazole group, an azathiophene group, a diazathiophene group, or a triazathiophene group.

[0065] The second ring can be an adamantyl group, norbornel group, norbornene group, cyclohexyl group, cyclohexene group, phenyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group.

[0066] In the embodiments, CY1 and CY2 may each independently be a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a phenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, etc. Groups, cyclopentadienyl groups, 1,2,3,4-tetrahydronaphthalene groups, thiophene groups, furan groups, indole groups, benzoborane heterocyclopentadienyl groups, benzophosphonane heterocyclopentadienyl groups, indene groups, benzothiophene groups, benzogermanium heterocyclopentadienyl groups, benzothiophene groups, benzoselenene groups, benzofuran groups, carbazole groups, dibenzoborane heterocyclopentadienyl groups, dibenzophosphonane heterocyclopentadienyl groups, fluorene groups, dibenzothiophene groups, dibenzogermanium heterocyclopentadienyl groups, di... Benzothiophene group, dibenzoselenene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborone cyclopentadiene group, azabenzophosphacyclopentadiene group, azaindene group, azabenzothiophene group, azabenzogerium cyclopentadiene group, azabenzothiophene group, azabenzoselenene group, azabenzofuran group, azacarbazole group, nitrogen The following groups are listed: dibenzoboron heterocyclopentadienyl group, azidibenzophosphonocyclopentadienyl group, azidifluorene group, azidibenzothiophene group, azidibenzogermanium heterocyclopentadienyl group, azidibenzothiophene group, azidibenzoselenene group, azidibenzofuran group, azidibenzothiophene 5-oxide group, azi-9H-fluorene-9-one group, azidibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group. Quinoline group, isoquinoline group, quinoxaloline group, quinazoline group, phenanthrene-rhein group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzooxazole group, benzothiazole group, benzooxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, or 5,6,7,8-tetrahydroquinoline group.

[0067] In the embodiments, CY1 and CY2 may each independently be a phenyl group, a naphthol group, a 1,2,3,4-tetrahydronaphthol group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthrene group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene group, an azirfluorene group, an azircarbazole group, an azirdibenzofuran group, an azirdibenzothiophene group, or an azirdibenzothiophene group.

[0068] In the embodiments, CY1 and CY2 may each independently be a phenyl group, naphthyl group, pyridine group, pyrimidine group, pyrazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, or dibenzothiophene group.

[0069] In the implementation method, by The represented part can be any of the groups represented by formulas 1-1 to 1-32:

[0070]

[0071]

[0072] Among them, in equations 1-1 to 1-32,

[0073] R 11 To R 14 Each can be independent, such as for R 10 The described, and each cannot be hydrogen,

[0074] Z1 can be as previously defined.

[0075] * indicates the binding site with M1, and

[0076] * indicates a binding site with an adjacent atom.

[0077] In the implementation method, by The represented part can be any of the groups represented by formulas 2-1 to 2-16:

[0078]

[0079]

[0080] Among them, in equations 2-1 to 2-16,

[0081] R 21 To R 24 Each can be independent, such as for R 20 As described, and R 21 To R 24 Neither of them can be hydrogen.

[0082] *' indicates the binding site with M1, and

[0083] * indicates a binding site with an adjacent atom.

[0084] In Equation 1A, Z1 can be -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3).

[0085] In the implementation, Z1 may not be -SiH3.

[0086] In the implementation method, Q1 to Q3 in Z1 can each be independently:

[0087] Deuterium, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0088] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0089] Each of the following is replaced by n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof.

[0090] For example, Q1 to Q3 in Z1 can each be -CH3, -CD3, -CD2H, or -CDH2.

[0091] In Equation 1A, a1 can be 1, 2, 3, or 4.

[0092] In the implementation, a1 can be 1.

[0093] In Formula 1A, * and *' each represent a binding site with an adjacent atom (i.e., M1).

[0094] In Equation 1, Ln2 can be a ligand represented by Equation 1B:

[0095] Formula 1B

[0096]

[0097] In Equation 1B, Y1 can be O, S, Se, C(R3)(R4), or N(R3).

[0098] In the implementation, Y1 can be O or S.

[0099] In the implementation method, Y1 can be 0.

[0100] In Equation 1B, Y2 can be C(R5) or N.

[0101] In Formula 1B, * and *' each represent a binding site with an adjacent atom (i.e., M1).

[0102] In equations 1A and 1B, R1 to R5, R 10 R 20 R 31 To R 34 and R 41 To R 47Each 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 C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9).

[0103] In the implementation method, R1 to R5, R 10 R 20 R 31 To R 34 and R 41 To R 47 Each of these can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 Alkyl, or C1-C 20 Alkoxy;

[0104] Each of the following C1-C is replaced: 20 Alkyl or C1-C 20Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof;

[0105] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroloyl, thiophenolyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, inzolyl, purinel, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxolinyl, quinazolinyl, cinolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophenolyl, benzoisothiazolyl, benzooxazolyl, benzoisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenolyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, or imidazopyrimidinyl;

[0106] Each of the following substituted groups is replaced by: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrrolyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, inzolyl, purine, quinolinyl, isoquinolinyl, benzo[a]quinolinyl, quinoxolinyl, quinazolinyl, carbazoleyl, phenanthrololyl, benzimidazolyl, benzofuranyl, benzo[a]thiophenyl, benziisothiazolyl, benzo[a]oxazolyl, benziisooxazolyl, triazolyl Tetraazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indoleyl, inzolyl, purinel, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxolinyl, quinazolinyl, cinolinyl, carbazoleyl, phenanthrololinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzoisothiazolyl, benzooxazolyl, benzoisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, imidazopyridyl, imidazopyrimidinyl, or combinations thereof; or

[0107] Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9).

[0108] In the implementation method, R1 to R5, R 10 R 20 R 31 To R 34 and R 41 To R 47 Each can be independently:

[0109] Hydrogen, deuterium, -F, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, or Cl-C 10 Alkyl; or

[0110] Groups represented by one of formulas 9-1 to 9-67, 9-101 to 9-114, 10-1 to 10-154, 10-201 to 10-350, and 10-601 to 10-636:

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] In formulas 9-1 to 9-67, 9-101 to 9-114, 10-1 to 10-154, 10-201 to 10-350, and 10-601 to 10-636, * indicates a binding site with an adjacent atom, Ph represents phenyl, TMS represents trimethylsilyl, and TMG represents trimethylgermanyl.

[0122] In Equation 1A, b10 and b20 can each be 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 independently.

[0123] Two or more substituents R on adjacent carbon atoms in Formula 1A 10 They can optionally combine with each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0124] Two or more substituents R on adjacent carbon atoms in Formula 1A 20 They can optionally combine with each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0125] In the implementation, two or more R 10 ; and / or two or more R 20 They may optionally be linked together via single bonds, double bonds, or a first linking group to form unsubstituted or linked groups with at least one R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups (e.g., each unsubstituted or with at least one R) 10a Substituted fluorene groups, xanthine groups, acridine groups, etc.). C5-C 30 Carbocyclic groups and C1-C 30 Heterocyclic groups may be as described herein. R 10a However, as in this article regarding R... 10 As described.

[0126] In the implementation, "not replaced or by at least one R" 10a Replacement C5-C30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Examples of "heterocyclic groups" may include those that are not substituted or are substituted with at least one R 10a Substituted phenyl groups, naphthyl groups, cyclopentyl groups, cyclopentadienyl groups, cyclohexyl groups, cycloheptyl groups, bicyclo[2.2.1]heptyl groups, furan groups, thiophene groups, pyrrole groups, thiophene groups, indole groups, benzofuran groups, benzothiophene groups, indole groups, or benzothiophene groups. R 10a However, as in this article regarding R... 10 As described.

[0127] The first linker group can be *-N(R8)-*', *-B(R8)-*', *-P(R8)-*', *-C(R8)(R9)-*', *-Si(R8)(R9)-*', *-Ge(R8)(R9)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R8)=*', *=C(R8)-*', *-C(R8)=C(R9)-*', *-C(=S)-*', or *-C≡C-*', where R8 and R9 can each be as described in this paper for R 10 As described, * and *' each represent a binding site with an adjacent atom.

[0128] In equations 1A and 1B, R1 to R5, R 10 R 20 R 31 To R 34 and R 41 To R 47 Two or more adjacent C5-C molecules may optionally combine with each other to form substituted or unsubstituted C5-C molecules. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0129] In the implementation method, Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each can be independently:

[0130] Deuterium, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0131] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0132] Each of the following is replaced by n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof.

[0133] In Equation 1B, R 31 To R 34 At least one of them may not be hydrogen.

[0134] In Equation 1B, R 31 To R 34 At least one of (e.g., R) 32 and / or R 33 It can be deuterium, -F, -Cl, -Br, I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, or unsubstituted Cl-C. 60 (For example, C1-C) 20 )alkyl, or deuterated C1-C 60 (For example, C1-C) 20 )alkyl.

[0135] In Equation 1B, R 31 To R 34 At least one of (e.g., R) 33 It can be a straight-chain C2-C 60 (For example, C2-C) 20 Alkyl, branched C3-C 60 (For example, C3-C) 20 Alkyl groups, deuterated straight-chain C2-C 60 (For example, C2-C) 20 )alkyl, or deuterated branched C3-C 60 (For example, C3-C) 20 )alkyl.

[0136] In an embodiment, the organometallic compound may be represented by Formula 11:

[0137] Formula 11

[0138]

[0139] In Equation 11,

[0140] M1, n1, n2, R1, R2, R 31 To R 34 R 41 To R 47 Y1 and Y2 can be defined as in Equations 1 and 1B, respectively.

[0141] In Equation 11, X 11 It can be C(Z1), C(R) 11 ), or N; X 12 It can be C(Z1), C(R) 12 ), or N; X 13 It can be C(Z1), C(R) 13 ), or N; X 14 It can be C(Z1), C(R) 14 ), or N; and X 11 To X 14 At least one of them can be C(Z1), where Z1 is as previously defined in Equation 1A, and R 11 To R 14 Each can be independent, as previously shown in Equation 1A for R. 10 As defined.

[0142] In Equation 11, X 21 It can be C(R) 21 ) or N, X 22 It can be C(R) 22 ) or N, X 23 It can be C(R) 23 ) or N, and X 24 It can be C(R) 24 ) or N, where R 21 To R 24 Each can be independent, as previously shown in Equation 1A for R. 20 As defined.

[0143] In Equation 11, R 11 To R 14 Two or more may optionally combine with each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, and R 21 To R 24 Two or more may optionally combine with each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0144] In an embodiment, the organometallic compound may be represented by any one of formulas 21-1 to 21-4:

[0145] Equation 21-1

[0146] Equation 21-2

[0147] Equation 21-3

[0148] Equation 21-4

[0149] Among them, in equations 21-1 to 21-4,

[0150] M1, n1, n2, R1, R2, R 31 To R 34 R 41 To R 47 Y1, Y2, and Z1 can each be defined as in equations 1, 1A, and 1B,

[0151] R 11 To R 14 Each can be independent, such as for R 10 As described,

[0152] R 21 To R 24 Each can be independent, such as for R 20 As described,

[0153] R 11 To R 14 Two or more may optionally combine with each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, and

[0154] R 21 To R 24 Two or more may optionally combine with each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0155] In some embodiments, the organometallic compound may be electrically neutral.

[0156] In an embodiment, the organometallic compound may be any one of compounds 1 to 84:

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164] The organometallic compound represented by Formula 1 satisfies the structure of Formula 1, wherein the Ln1 ligand is represented by Formula 1A and the Ln2 ligand is represented by Formula 1B. With this structure, the organometallic compound represented by Formula 1 can have improved structural stability, and therefore can have excellent lifetime characteristics, excellent luminescence properties, reduced roll-off, and properties suitable for use as a high-purity luminescent material through a controlled emission wavelength range.

[0165] Furthermore, the organometallic compounds represented by Formula 1 can have excellent electromobility, and therefore, electronic devices including the organometallic compounds, such as organic light-emitting devices including the organometallic compounds, can exhibit low driving voltage, high efficiency, long lifetime, and reduced roll-off.

[0166] Furthermore, the photochemical stability of the organometallic compound represented by Formula 1 can be improved, and therefore, electronic devices including the organometallic compound, such as organic light-emitting devices including the organometallic compound, can exhibit high luminous efficiency, long lifetime, and high color purity.

[0167] In the embodiment, the maximum emission wavelength (emission peak wavelength, λ) of the emission spectrum or EL spectrum of the organometallic compound is... max It can be in the range of about 490nm to about 580nm or in the range of about 500nm to about 600nm.

[0168] In embodiments, the half-width at half-maximum (FWHM) of the emission peak in the emission spectrum or electroluminescence (EL) spectrum of the organometallic compound may be 70 nm or less. For example, the FWHM of the emission peak in the emission spectrum or EL spectrum of the organometallic compound may be in the range of about 30 nm to about 65 nm, about 40 nm to about 63 nm, or about 45 nm to about 62 nm.

[0169] Due to the emission wavelength and FWHM, the organometallic compound represented by Formula 1 is suitable for use in the organic layer of an organic light-emitting device, for example, suitable as a dopant in the emission layer of the organic layer. Therefore, another aspect of this disclosure provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer disposed between the first and second electrodes and including an emission layer, wherein the organic layer comprises at least one organometallic compound represented by Formula 1.

[0170] Because of the organic layer comprising an organometallic compound represented by Formula 1, organic light-emitting devices can exhibit excellent characteristics in terms of driving voltage, current efficiency, power efficiency, external quantum efficiency, lifetime, and / or color purity. Furthermore, such organic light-emitting devices can have reduced roll-off and a relatively narrow FWHM (field-to-weight ratio) for the emission peak in the EL spectrum.

[0171] The organometallic compound represented by Formula 1 can be used between electrode pairs in organic light-emitting devices. For example, the organometallic compound represented by Formula 1 can be included in the emitting layer. In this respect, the organometallic compound can act as a dopant, and the emitting layer can further include a host (i.e., the amount of the organometallic compound represented by Formula 1 in the emitting layer can be less than the amount of the host included in the emitting layer by weight).

[0172] In this embodiment, the emitting layer or organic light-emitting device may emit green light. For example, the emitting layer or organic light-emitting device may have a maximum emission wavelength in the range of about 490 nm to about 580 nm, or about 500 nm to about 600 nm.

[0173] In an embodiment, the field-wide emission height (FWHM) of the emission peak of the EL spectrum of the emitting layer or organic light-emitting device may be 70 nm or less. For example, the FWHM of the emission peak of the EL spectrum of the emitting layer or organic light-emitting device may be in the range of about 30 nm to about 65 nm, about 40 nm to about 63 nm, or about 45 nm to about 62 nm.

[0174] As used herein, the expression “(organic layer) comprises at least one organometallic compound” can be interpreted as “(organic layer) may comprise one organometallic compound of formula 1 or at least two different organometallic compounds of formula 1”.

[0175] For example, the organic layer may comprise only compound 1 as the organometallic compound. In this respect, compound 1 may be included in the emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may comprise both compound 1 and compound 2 as the organometallic compound. In this respect, compound 1 and compound 2 may exist in the same layer (e.g., both compound 1 and compound 2 may exist in the emitting layer).

[0176] The first electrode can be the anode of the hole injection electrode and the second electrode can be the cathode of the electron injection electrode, or the first electrode can be the cathode of the electron injection electrode and the second electrode can be the anode of the hole injection electrode.

[0177] For example, in an organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region disposed between the first electrode and the emitting layer and an electron transport region disposed 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.

[0178] As used herein, the term "organic layer" refers to one or more layers disposed between the first and second electrodes of an organic light-emitting device. In addition to organic compounds, "organic layer" may also include organometallic complexes containing metals.

[0179] Figure 1 This is a schematic cross-sectional view of the organic light-emitting device 10 according to an embodiment. Figure 1 This is a cross-sectional schematic diagram of an exemplary embodiment. Thus, variations in the shape of the figure will be anticipated due to, 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 shown herein, but rather include deviations in shape due to, for example, manufacturing processes. For example, regions illustrated or described as flat may typically have rough and / or non-linear characteristics. Furthermore, sharp corners in the illustrations may be rounded. Therefore, the regions shown in the figures are schematic in nature, and their shapes are not intended to illustrate the precise shapes of the regions and are not intended to limit the scope of the claims.

[0180] The following text will refer to Figure 1 The structure and manufacturing method of an organic light-emitting device 10 according to an embodiment are described. The organic light-emitting device 10 may have a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are sequentially stacked.

[0181] A substrate may be further disposed below the first electrode 11 or on the second electrode 19. The substrate may be a substrate commonly used in organic light-emitting devices, such as a glass substrate or a transparent plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0182] The first electrode 11 can be formed, for example, by depositing or sputtering a material for forming the first electrode 11 onto a substrate. The first electrode 11 can be an anode. The material used to form the first electrode 11 can be a material with a high work function to facilitate hole injection. The first electrode 11 can be a reflective electrode, a semi-transparent semi-reflective electrode, or a transmissive electrode. The material used to form the first electrode can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material used to form the first electrode can be a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0183] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 11 is not limited to this.

[0184] The organic layer 15 can be disposed on the first electrode 11.

[0185] The organic layer 15 may include an emission layer and may further include a hole transport region and an electron transport region.

[0186] The hole transport region can be arranged between the first electrode 11 and the emitter layer.

[0187] 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.

[0188] The hole transport region may consist of only a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer / hole transport layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the constituent layers are stacked sequentially from the first electrode 11 in the order stated herein.

[0189] When the hole transport region includes a hole injection layer, the hole injection layer can be formed on the first electrode 11 by using various methods such as vacuum deposition, spin coating, tape casting, and / or Langmuir-Broguet (LB) deposition.

[0190] When a hole injection layer is formed by vacuum deposition, the deposition conditions can vary depending on the compound used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer to be formed, and can include a deposition temperature of about 100°C to about 500°C, and about 10 -8 To about 10 -3 The vacuum degree of Tor and the approximation / seconds to approximately The deposition rate is 1 / s. However, the deposition conditions are not limited to this.

[0191] When a hole injection layer is formed by spin coating, the coating conditions may vary depending on the compound used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer, and may include a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to about 200°C for removing the solvent after coating. However, the coating conditions are not limited to these.

[0192] The conditions for forming the hole transport layer and the electron blocking layer can be found in the description provided for the conditions for forming the hole injection layer.

[0193] The hole transport region may include, for example, at least one of the following: m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-sulfonated styrene) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-sulfonated styrene) (PANI / PSS), compounds represented by formula 201, and compounds represented by formula 202:

[0194]

[0195]

[0196] Formula 201

[0197] Formula 202

[0198] In Equation 201, Ar 101 and Ar 102 Each can be independently:

[0199] Phenylidene, cyclopentadienyl, indene, naphthyl, azulene, heptadienyl, acenaphthene, fluorene, phenenyl, phenanthrene, anthracene, fluoranyl, benzo[9,10]phenanthrene, pyrene, phenylene alkyl, tetraphenylene, terephthalyl, perylene, or pentaphenylene; or

[0200] Each of the following substituted groups is phenylene, cyclopentadienylene, indene, naphthylene, azulene, heptadienylene, acenaphthene, fluorene, phenenylene, phenanthrene, anthracene, fluorenylene, benzo[9,10]phenanthrene, pyrene, etc. alkyl, tetraphenylene, terephthalyl, perylene, or pentaphenylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, or combinations thereof.

[0201] In Equation 201, xa and xb can each be an integer from 0 to 5, or each can be 0, 1, or 2. For example, xa can be 1 and xb can be 0, but xa and xb are not limited to these values.

[0202] In equations 201 and 202, R 101 To R 108 R 111 To R 119 and R 121 To R 124 Each can be independently:

[0203] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), or C1-C 10 Alkyl groups (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);

[0204] Each of the following C1-C is replaced: 10 Alkyl or C1-C 10 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, or combinations thereof;

[0205] Phenyl, naphthyl, anthraceneyl, fluorenyl, or pyrene; or

[0206] Each of the following substituted groups is phenyl, naphthyl, anthraceneyl, fluorenyl, or pyrene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, C1-C 10 Alkoxy groups, or combinations thereof, but the implementation methods are not limited thereto.

[0207] In Equation 201, R 109 Possible forms:

[0208] phenyl, naphthyl, anthraceneyl, or pyridyl; or

[0209] Each of the following substituted groups is phenyl, naphthyl, anthracene, or pyridyl: 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.

[0210] In some embodiments, the compound represented by formula 201 may be represented by formula 201A, but the embodiments are not limited thereto:

[0211] Formula 201A

[0212]

[0213] In Equation 201A, R 101 R 111 R 112 and R 109 Each can be as described in this article.

[0214] For example, the compounds represented by formula 201 and the compounds represented by formula 202 may include compounds HT1 to HT20, but the implementation is not limited thereto:

[0215]

[0216]

[0217] The thickness of the hole transport region can be approximately to approximately For example, about to approximately Within the range. When the hole transport region includes at least one hole injection layer and a hole transport layer, the thickness of the hole injection layer can be approximately... to approximately For example, about to approximately Within a certain range, and the thickness of the hole transport layer can be approximately... to approximately For example, about to approximately Within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage when the hole transport region, hole injection layer, and hole transport layer thickness are within these ranges.

[0218] In addition to the materials described above, the hole transport region may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0219] The charge-generating material can be, for example, a p-doper. The p-doper can be, but is not limited to, one of the following: a quinone derivative, a metal oxide, and a cyano-containing compound. Non-limiting examples of p-dopers include: quinone derivatives, such as tetracyanoquinone dimethyl ether (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl ether (F4-TCNQ); metal oxides, such as tungsten oxide or molybdenum oxide; and cyano-containing compounds, such as, but not limited to, compounds HT-D1 or F12.

[0220]

[0221] Hole transport regions may include buffer layers.

[0222] The buffer layer can compensate for the optical resonant distance according to the wavelength of the light emitted from the emitting layer, thereby improving efficiency.

[0223] When the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer can be one or more of the materials described above for forming the hole transport region and the main material described below, but the implementation is not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer can be mCP, which will be described below.

[0224] The emitter layer can be formed on the hole transport region by vacuum deposition, spin coating, tape casting, LB deposition, etc. When the emitter layer is formed by vacuum deposition or spin coating, the deposition or coating conditions can be similar to those used when forming the hole injection layer, although the deposition or coating conditions may vary depending on the compound to be used.

[0225] The emitter layer may include a host and a dopant, and the dopant may include an organometallic compound represented by Formula 1.

[0226] The main component may include at least one of TPBi, TBADN, ADN (also known as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, and compound GH3:

[0227]

[0228] In an embodiment, the main body may further include a compound represented by formula 301:

[0229] Formula 301

[0230]

[0231] In Equation 301, Ar 111 and Ar 112 Each can be independently:

[0232] Phenylidene, naphthylene, phenanthrene, or pyrene; or phenylene, naphthylene, phenanthrene, or pyrene, each substituted with phenyl, naphthyl, anthracene, or a combination thereof.

[0233] In Equation 301, Ar 113 To Ar 116 Each can be independently:

[0234] C1-C 10 Alkyl, phenyl, naphthyl, phenanthrene, or pyrene; or

[0235] The phenyl, naphthyl, phenanthryl, or pyrene groups, each substituted with phenyl, naphthyl, anthracene, or a combination thereof.

[0236] In Equation 301, g, h, i, and j can each be an integer from 0 to 4, and can each be, for example, 0, 1, or 2.

[0237] In Equation 301, Ar 113 To Ar 116 Each can be independently:

[0238] C1-C substituted with phenyl, naphthyl, anthracene, or a combination thereof 10 alkyl;

[0239] Phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, or fluoreneyl;

[0240] Each of the following substituted groups is phenyl, naphthyl, anthraceneyl, pyrene, phenanthrene, or fluorenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, fluorenyl, or combinations thereof; or

[0241]

[0242] In one or more embodiments, the body may include a compound represented by formula 302:

[0243] Formula 302

[0244]

[0245] In Equation 302, Ar 122 To Ar 125 Each can be like Ar of Equation 301 113 As defined.

[0246] In Equation 302, Ar 126 and Ar 127 Each can be independently C1-C 10 Alkyl (e.g., methyl, ethyl, or propyl).

[0247] In Equation 302, k and l can each be independent integers from 0 to 4. For example, k and l can be 0, 1, or 2.

[0248] When the organic light-emitting device is a full-color organic light-emitting device, the emitting layer can be patterned into a red emitting layer, a green emitting layer, and a blue emitting layer. In one or more embodiments, the emitting layer can emit white light due to the structure in which red, green, and / or blue emitting layers are stacked.

[0249] When the emitter layer comprises a host and a dopant, the amount of dopant may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but the implementation is not limited thereto.

[0250] The thickness of the emission layer can be approximately to approximately For example, about to approximately Within the range described above, excellent light-emitting characteristics can be obtained without a significant increase in driving voltage when the thickness of the emitting layer is within the range described above.

[0251] Next, an electronic transmission area can be arranged on the emission layer.

[0252] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0253] For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure, or an electron transport layer / electron injection layer structure, and the structure of the electron transport region is not limited to these. The electron transport layer may have a multilayer structure or a single-layer structure comprising two or more different materials.

[0254] The conditions for forming the hole blocking layer, electron transport layer, and electron injection layer that constitute the electron transport region can be found in the description provided for the conditions for forming the hole injection layer.

[0255] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAlq, but the implementation is not limited thereto:

[0256]

[0257] The thickness of the hole-blocking layer can be approximately to approximately For example, about to approximately Within these ranges, excellent hole blocking characteristics can be obtained without a significant increase in driving voltage when the thickness of the hole blocking layer is within these ranges.

[0258] The electron transport layer may include at least one of BCP, Bphen, Alq3, BAlq, TAZ, and NTAZ:

[0259]

[0260] In one or more embodiments, the electron transport layer may include at least one compound ET1 to ET25, but the embodiments are not limited thereto:

[0261]

[0262]

[0263] The thickness of the electron transport layer can be approximately to approximately For example, about to approximately Within these ranges, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage when the thickness of the electron transport layer is within these ranges.

[0264] In addition to the materials described above, the electron transport layer may further include a metallic material.

[0265] Metal-containing materials may include Li complexes. Li complexes may include, for example, compounds ET-D1 (lithium 8-hydroxyquinoline, LiQ) or ET-D2:

[0266]

[0267] The electron transport region may also include an electron injection layer that facilitates the injection of electrons from the second electrode 19.

[0268] The electron-injected layer may include LiQ, LiF, NaCl, CsF, Li2O, BaO, or combinations thereof.

[0269] The thickness of the electron injection layer can be approximately to approximately For example, about to approximately Within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage when the thickness of the electron injection layer is within these ranges.

[0270] The second electrode 19 may be disposed on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a metal, alloy, conductive compound, or combination thereof having a relatively low work function. For example, lithium (Li), Mg, Al, Al-Li, Ca, Mg-In, or Mg-Ag may be used as the material for forming the second electrode 19. In one or more embodiments, for the fabrication of a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0271] Already referenced Figure 1 Organic light-emitting devices are described, but implementation methods are not limited thereto.

[0272] Another aspect of this disclosure provides diagnostic compositions comprising at least one organometallic compound represented by Formula 1.

[0273] Organometallic compounds represented by Formula 1 can provide high luminescence efficiency, and therefore, diagnostic compositions including said organometallic compounds can have high diagnostic efficiency.

[0274] Diagnostic compositions can be used in a variety of applications, including diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0275] When used to describe chemical groups containing carbon atoms, it has the form "C". x -C y The expression “” means that the unsubstituted form of the chemical group has x to y carbon atoms, including the endpoints x and y. For example, C1-C 50 Alkyl groups are alkyl groups in their unsubstituted form having 1 to 50 carbon atoms. In some embodiments and general structures, some chemical groups may be replaced by one or more substituents, such as R. S Replace. Use the expression "C" x -C y "R of the defined chemical group" S The substituted form can contain more than y carbon atoms, depending on any group R. S The identity (characteristics). For example, being identified by exactly one group R. SReplacement of "C1-C" 50 Alkyl (where R) S A phenyl group (-C6H5) can contain 7 to 56 carbon atoms. Therefore, typically, when using "C..." x -C y "The chemical group defined in the expression is substituent for one or more carbon atoms R." S When substituted, the minimum and maximum total number of carbon atoms in the chemical group are determined by the substituent R from all carbon-containing groups. S The sum of the number of carbon atoms is added to both x and y to determine the value.

[0276] As used in this article, the term "C1-C" 60 "Alkyl" refers to a monovalent group in a straight-chain or branched saturated aliphatic hydrocarbon having 1 to 60 carbon atoms. In this article, C1-C... 60 Alkyl groups can be C1-C 20 Alkyl groups, such as C1-C 10 Alkyl or C1-C6 alkyl. These alkyl groups can each be straight-chain or branched. In the case of branched alkyl groups, the lower limit of the carbon number range for each alkyl group becomes 3. C1-C 60 Non-limiting examples of alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, hexyl, etc. As used herein, the term "C1-C" is similar. 60 "Alkylene" refers to a straight-chain or branched divalent group of a saturated aliphatic hydrocarbon having 1 to 60 carbon atoms, wherein the valence can be on two carbon atoms.

[0277] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 It is C1-C 60 The monovalent group (alkyl) may include methoxy, ethoxy, isopropoxy, etc. as examples of which are not limited.

[0278] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C... 60 A structure containing at least one carbon-carbon double bond at the middle or end of an alkyl group, and non-limiting examples may include vinyl, propenyl, butenyl, etc. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to the group formed at C2-C... 60 The alkyl group has at least one divalent group with a carbon-carbon double bond at the middle or end.

[0279] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60An alkyl group contains at least one carbon-carbon triple bond at its middle or end, and non-limiting examples may include ethynyl, propynyl, etc. As used herein, the term "C2-C" is used... 60 "Immyneyl" refers to a group with a C2-C... 60 The alkyl group contains at least one divalent group with a carbon-carbon triple bond structure at the middle or end.

[0280] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms as cyclic atoms, and non-limiting examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc. The term "C3-C" is used herein. 10 "Cycloalkylene" refers to a divalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms as cyclic atoms.

[0281] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated cyclic group having at least one heteroatom, such as N, O, P, Si, or S, as a cyclic atom and 1 to 10 carbon atoms as cyclic atoms. The valence can be on either the heteroatom or the carbon atom. "C1-C" 10 Non-limiting examples of "heterocyclic alkyl" may include tetrahydrofuranyl, tetrahydrothiophenyl, etc., as used herein with the term "C1-C". 10 "Hypocyclic alkyl" refers to a divalent saturated cyclic group having at least one heteroatom, such as N, O, P, Si or S, as a cyclic atom and 1 to 10 carbon atoms as cyclic atoms, wherein each valence may be on a heteroatom or a carbon atom, or two valences may be on the same atom.

[0282] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent hydrocarbon cyclic group having 3 to 10 carbon atoms as cyclic atoms and at least one carbon-carbon double bond in its ring and not being aromatic, and non-limiting examples may include cyclopentenyl, cyclohexenyl, cycloheptenyl, etc. As used herein, the term "C3-C" is also used. 10 "Biopylene alkenyl" refers to a divalent hydrocarbon cyclic group that has 3 to 10 carbon atoms as cyclic atoms and at least one carbon-carbon double bond in its ring and is not aromatic.

[0283] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent cyclic group that has at least one heteroatom (e.g., N, O, P, Si, or S) as a cyclic atom, 1 to 10 carbon atoms as cyclic atoms, and at least one carbon-carbon double bond, and is not aromatic. C1-C 10Non-limiting examples of heterocyclic alkenyl groups may include 2,3-dihydrofuranyl, 2,3-dihydrothiophenyl, etc., as used herein with the term "C1-C". 10 "Heterocyclic alkenyl" refers to a divalent cyclic group that has at least one heteroatom such as N, O, P, Si or S as a cyclic atom, 1 to 10 carbon atoms as cyclic atoms, and at least one carbon-carbon double bond and is not aromatic.

[0284] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group in a carbocyclic aromatic system having 6 to 60 carbon atoms as cyclic atoms, and as used herein in the term "C6-C". 60 "Arylene" refers to a divalent group in a carbocyclic aromatic system with 6 to 60 carbon atoms as cyclic atoms. (C6-C) 60 Non-limiting examples of aryl groups may include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, Base, etc. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the rings can be fused together. The terms "fused" and "condensed" are used interchangeably and refer to two or more cyclic structures sharing one or more atoms within the ring structure. Non-limiting examples of fused ring (fused ring) systems include naphthalene, anthracene, and centrocyclic alkenes. C7-C 60 Alkyl aryl refers to an alkyl group consisting of at least one C1-C2 group. 54 Alkyl-substituted C6-C 59 Aryl.

[0285] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a cyclic aromatic system having at least one heteroatom, such as N, O, P, Si, or S, as a cyclic atom and 1 to 60 carbon atoms as cyclic atoms. The term "C1-C" is used herein. 60 "Hypo-heteroaryl" refers to a divalent group having a cyclic aromatic system in which at least one heteroatom, such as N, O, P, Si, or S, is a cyclic atom and 1 to 60 carbon atoms are cyclic atoms. C1-C 60 Non-limiting examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, etc. When C1-C 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the rings can fused together. C2-C 60 Alkyl heteroaryl refers to a compound formed by at least one C1-C2 group. 59 Alkyl-substituted C1-C59 Mixed aromatic compounds.

[0286] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 It is C6-C 60 Aryl), and as used herein, the term "C6-C" 60 "Arylthio" refers to -SA 103 (where A) 103 It is C6-C 60 Aryl).

[0287] As used in this article, the term "C1-C" 60 "Heteroaryloxy" refers to -OA 104 (where A) 104 It is C1-C 60 (Heteroaryl), and as used herein, the term "C1-C 60 "Heteroary sulfide" refers to -SA 105 (where A) 105 It is C1-C 60 (Miscellaneous aromatics).

[0288] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) that has two or more fused rings, has only carbon atoms as cyclic atoms, and is not aromatic in its entire structure. Non-limiting examples of monovalent nonaromatic fused polycyclic groups may include fluorene groups, etc. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group that has two or more fused rings, has only carbon atoms as cyclic atoms, and is not aromatic in its entire structure.

[0289] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms) that has two or more fused rings, has heteroatoms such as N, O, P, Si, or S as cyclic atoms in addition to carbon atoms, and is not aromatic in its entire structure. Non-limiting examples of monovalent nonaromatic fused heterocyclic groups may include carbazole groups, etc. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group that has two or more fused rings, has heteroatoms such as N, O, P, Si, or S as cyclic atoms in addition to carbon atoms, and is not aromatic in its entire structure.

[0290] As used in this article, the term "C5-C" 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as cyclic atoms. (C5-C)30 The carbon ring group can be a monocyclic group or a polycyclic group.

[0291] As used in this article, the term "C1-C" 30 A "heterocyclic group" refers to a saturated or unsaturated cyclic group that has at least one heteroatom, such as N, O, P, Si, or S, as a cyclic atom in addition to 1 to 30 carbon atoms. (C1-C) 30 Heterocyclic groups can be monocyclic or polycyclic.

[0292] In this specification, TMS stands for *-Si(CH3)3, and TMG stands for *-Ge(CH3)3.

[0293] Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 heteroaryl, 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 may be:

[0294] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy;

[0295] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 ), or combinations thereof;

[0296] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups;

[0297] Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C60 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, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 ), or a combination thereof; or

[0298] -Si(Q 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 ), or -P(=O)(Q 38 (Q) 39 ),and

[0299] Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

[0300] By referring to the synthesis examples, the method for synthesizing the organometallic compound represented by Formula 1 is as can be recognized by those skilled in the art.

[0301] The compounds and organic light-emitting devices according to the embodiments are described in detail with reference to the synthesis examples and embodiments. However, the following synthesis examples and embodiments are not intended to limit the scope of this disclosure. 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.

[0302] Example

[0303] Synthesis Example 1: Synthesis of Compound 7

[0304]

[0305] (1) Synthesis of compound 7A(1)

[0306] 2-Phenylacetyl-5-(trimethylsilyl)pyridine (2.1 g, 9.24 mmol) and iridium chloride trihydrate (IrCl3(H2O)) were prepared. n , n=3)(1.55 g, 4.40 mmol) was mixed with 60 mL of 2-ethoxyethanol and 20 mL of distilled water, stirred under reflux for 24 hours, and then cooled to room temperature. The resulting solid was separated by filtration and washed thoroughly in sequence with water, methanol, and n-hexane. The obtained solid was dried in a vacuum oven to obtain 2.18 g (73% yield) of compound 7A (1).

[0307] (2) Synthesis of compound 7A

[0308] Compound 7A(1) (2.18 g, 1.60 mmol) was mixed with 75 mL of dichloromethane (DCM), and then silver trifluoromethanesulfonate (AgOTf) (0.86 g, 3.36 mmol) mixed with 25 mL of methanol (MeOH) was added. The mixture was then stirred at room temperature for 18 hours while blocking light with aluminum foil. The mixture was filtered through diatomaceous earth to remove the solids formed, and the filtrate was evaporated under reduced pressure to obtain the solid (compound 7A), which was used in the next reaction without further purification.

[0309] (3) Synthesis of compound 7B

[0310] Under a nitrogen atmosphere, 2-chloro-4-(2,2-dimethylpropyl-1,1-d2)-5-(methyl-d3)pyridine (2.5 g, 12.33 mmol) and 4,4,5,5-tetramethyl-2-(phenanthrene[3,4-b]benzofuran-10-yl)-1,3,2-dioxane (5.35 g, 13.56 mmol) were dissolved in 120 mL of 1,4-dioxane. Then, potassium carbonate (K2CO3) (5.11 g, 36.99 mmol) dissolved in 40 mL of distilled water (DI water) was added to the reaction mixture, followed by the addition of palladium catalyst (Pd(PPh3)4) (1.0 g, 0.86 mmol). The reaction mixture was then stirred under reflux at 100 °C. Following extraction, the obtained solid was subjected to column chromatography (eluent: n-hexane and ethyl acetate) to obtain 4.21 g (79% yield) of compound 7B. The obtained compound was confirmed by MS and HPLC analysis.

[0311] HRMS (MALDI): For C 31 H 22 Calculated value of D5NO: m / z 434.2406, measured value: 434.2401

[0312] (4) Synthesis of compound 7

[0313] Compound 7A (1.87 g, 2.18 mmol) and compound 7B (0.95 g, 2.18 mmol) were mixed in 22 mL of 2-ethoxyethanol and 22 mL of N,N-dimethylformamide (DMF) and stirred under reflux for 24 hours, then the temperature was lowered. The resulting mixture was evaporated under reduced pressure, and the solid was subjected to column chromatography (eluent: n-hexane and dichloromethane) to obtain 0.82 g (35% yield) of compound 7. The obtained compound was confirmed by MS and HPLC analysis.

[0314] HRMS (MALDI): For C 59 H 53 Calculated value of D5IrN3OSi2: m / z 1078.4061, measured value: 1078.4067

[0315] Synthesis Example 2: Synthesis of Compound 14

[0316]

[0317] (1) Synthesis of compound 14B

[0318] Under a nitrogen atmosphere, 2-chloro-4-(2,2-dimethylpropyl-1,1-d2)-5-(methyl-d3)pyridine (2.50 g, 12.33 mmol) and 10-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)benzo[2,3]benzofurano[5,4-h]quinoline (5.36 g, 13.56 mmol) were dissolved in 120 mL of 1,4-dioxane. Then, potassium carbonate (K2CO3) (5.11 g, 36.99 mmol) dissolved in 40 mL of distilled water (DI water) was added to the reaction mixture, followed by the addition of palladium catalyst (Pd(PPh3)4) (1.0 g, 0.86 mmol). The reaction mixture was then stirred under reflux at 100 °C. Following extraction, the obtained solid was subjected to column chromatography (eluent: n-hexane and ethyl acetate) to obtain 3.96 g (74% yield) of compound 14B. The obtained compound was confirmed by MS and HPLC analysis.

[0319] HRMS (MALDI): For C 30 H 21 Calculated value of D5N2O: m / z 435.2359, measured value: 435.2352

[0320] (2) Synthesis of compound 14

[0321] Except that compound 14B (0.95 g, 2.18 mmol) was used instead of compound 7B, 0.77 g (33% yield) of compound 14 was obtained using the same method as that used to synthesize compound 7 in Synthetic Example 1. The obtained compound was confirmed by MS and HPLC analysis.

[0322] HRMS (MALDI): For C 58 H 52 Calculated value of D5IrN4OSi2: m / z 1079.4014, measured value: 1079.4019

[0323] Synthesis Example 3: Synthesis of Compound 21

[0324]

[0325] (1) Synthesis of compound 21A(1)

[0326] 2-Phenyl-5-(trimethylgermanyl)pyridine (2.1 g, 7.72 mmol) and iridium chloride trihydrate (1.30 g, 3.68 mmol) were mixed with 60 mL of 2-ethoxyethanol and 20 mL of distilled water and stirred under reflux for 24 hours, then cooled to room temperature. The resulting solid was separated by filtration and thoroughly washed in sequence with water, methanol, and n-hexane. The obtained solid was dried in a vacuum oven to obtain 2.18 g (77% yield) of compound 21A (1).

[0327] (2) Synthesis of compound 21A

[0328] Compound 21A(1) (2.18 g, 1.42 mmol) was mixed with 75 mL of dichloromethane, and then AgOTf (0.76 g, 2.97 mmol) mixed with 25 mL of methanol was added. The mixture was then stirred at room temperature for 18 hours while blocking light with aluminum foil. The mixture was filtered through diatomaceous earth to remove the solids formed, and the filtrate was evaporated under reduced pressure to obtain the solid (compound 21A), which was used in the next reaction without further purification.

[0329] (3) Synthesis of compound 21

[0330] Except that compound 21A (1.82 g, 1.92 mmol) was used instead of compound 7A, 0.74 g (33% yield) of compound 21 was obtained using the same method as that used to synthesize compound 7 in Example 1. The obtained compound was confirmed by MS and HPLC analysis.

[0331] HRMS (MALDI): For C 59 H 53Calculated value of D5Ge2IrN3O: m / z 1170.2947, measured value: 1170.2941

[0332] Synthesis Example 4: Synthesis of Compound 28

[0333]

[0334] Except that compound 21A (1.82 g, 1.92 mmol) was used instead of compound 7A and compound 14B (0.84 g, 1.92 mmol) was used instead of compound 7B, 0.69 g (31% yield) of compound 28 was obtained using the same method as that used to synthesize compound 7 in synthetic example 1. The obtained compound was confirmed by MS and HPLC analysis.

[0335] HRMS (MALDI): For C 58 H 52 Calculated value of D5Ge2IrN4O: m / z 1171.2899, measured value: 1171.2892

[0336] Example 1

[0337] ITO (as anode) patterned glass substrates were cut to dimensions of 50mm × 50mm × 0.5mm, ultrasonically treated with isopropanol and pure water for 5 minutes each, and then cleaned by UV irradiation and ozone exposure for 30 minutes. The resulting glass substrates were then loaded onto a vacuum deposition apparatus.

[0338] Compounds HT3 and F12 (p-doper) were vacuum co-deposited on the anode at a weight ratio of 98:2 to form a structure with... A hole injection layer of a certain thickness was formed, and compound HT3 was vacuum deposited on the hole injection layer to form a hole injection layer with a certain thickness. A hole transport layer of a certain thickness.

[0339] Subsequently, compound GH3 (host) and compound 7 (dopant) were vacuum co-deposited on the hole transport layer at a weight ratio of 92:8 to form a structure with... The thickness of the emission layer.

[0340] Then, compound ET3 and LiQ (n-doper) were vacuum co-deposited on the emitter layer at a volume ratio of 50:50 to form a structure with... An electron transport layer of a certain thickness is formed by vacuum deposition of LiQ on the electron transport layer to create an electron transport layer with a certain thickness. An electron-injected layer of a certain thickness is formed, and Al is vacuum-deposited onto the electron-injected layer to form a layer with [missing information]. A cathode of a certain thickness is used to complete the fabrication of organic light-emitting devices.

[0341]

[0342] Examples 2 to 4 and Comparative Examples 1 and 2

[0343] The organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of compound 7 as dopants when forming the emission layer.

[0344] For each of the organic light-emitting devices fabricated in Examples 1 to 4 and Comparative Examples 1 and 2, the driving voltage, maximum external quantum efficiency (Max EQE), and maximum emission wavelength (λ) of the emission spectrum were evaluated. max ), roll-off ratio, and lifetime characteristics (LT) 97 (At 6,000 nits), and the results are shown in Table 1. An ammeter-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation equipment. Lifetime characteristics (LT) 97 The time required for the brightness to reach 97% of the initial brightness (100%) is measured and listed in Table 1 as a relative value with respect to Comparative Example 1. The roll-off ratio is calculated according to Equation 20.

[0345] Equation 20

[0346] Roll-off ratio = {1 - (luminous efficacy (at 6,000 nits) / maximum luminous efficacy)} × 100%

[0347] Table 1

[0348]

[0349]

[0350] As shown in Table 1 above, the organic light-emitting devices of Examples 1 to 4 exhibit low driving voltage, high external quantum efficiency, low roll-off ratio, and long lifetime. Furthermore, compared to the organic light-emitting devices of Comparative Examples 1 and 2, the organic light-emitting devices of Examples 1 to 4 demonstrate even lower driving voltage and roll-off ratio, higher external quantum efficiency, and significantly superior lifetime characteristics.

[0351] The organometallic compounds possess excellent electrical properties and thermal stability. Therefore, electronic devices using these organometallic compounds, such as organic light-emitting devices, can exhibit low driving voltage, high efficiency, long lifetime, and low roll-off ratio.

[0352] Therefore, high-quality organic light-emitting devices can be achieved through the use of the aforementioned organometallic compounds. Furthermore, electronic devices incorporating the aforementioned organic light-emitting devices can be provided.

[0353] It should be understood that the embodiments described herein are to be considered in a descriptive sense only and are not intended for limiting purposes. The descriptions of features or aspects in each embodiment should typically be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims.

Claims

1. Organometallic compounds, represented by Formula 1: Formula 1 M1(Ln1) n1 (Ln2) n2 in, In Equation 1, M1 is a transition metal. Ln1 is the ligand represented by Equation 1A. Ln2 is the ligand represented by Equation 1B. n1 is 1 or 2. n2 is 1 or 2. Among them, in equations 1A and 1B, CY1 and CY2 are each independently C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups, where X1 is C, CH, or N, and X2 is C, CH, or N. Y1 is O, S, Se, C(R3)(R4), or N(R3). Y2 is C(R5) or N. Z1 is either -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3). a1 is 1, 2, 3, or 4. R1 to R5, R 10 R 20 R 31 To R 34 and R 41 To R 47 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 C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9), Two or more R 10 Optionally, they combine to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, Two or more R 20 Optionally, they combine to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, R1 to R5, R 10 R 20 R 31 To R 34 and R 41 To R 47 Two or more adjacent C5-C molecules may optionally combine with each other to form substituted or unsubstituted C5-C molecules. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, b10 and b20 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. * and *' each represent the binding site with M1. Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthio, substituted C1-C 60 heteroaryl, 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: Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy; Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 ), or combinations thereof; C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups; Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 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 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, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 ), -P(=O)(Q 28 (Q) 29 ), or a combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、or -P(=O)(Q 38 (Q) 39 ),and Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

2. The organometallic compound according to claim 1, M1 is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

3. The organometallic compound according to claim 1, Where M1 is Ir, and The sum of n1 and n2 is 3.

4. The organometallic compound according to claim 1, Where Y1 is O.

5. The organometallic compound according to claim 1, Wherein CY1 and CY2 are independently i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused together, iv) a fused ring in which two or more second rings are fused together, or v) a fused ring in which one or more first rings and one or more second rings are fused together. The first ring is a cyclopentyl group, cyclopentadienyl group, furan group, thiophene group, pyrrole group, thiophene group, indene group, benzofuran group, benzothiophene group, indole group, benzothiophene group, oxazole group, isoxazole group, oxadiazole group, isoxadiazole group, oxtriazole group, isoxtriazole group, thiazole group, isothiazole group, thiadiazole group, isothiazole group, thiatriazole group, isothiazole group, pyrazole group, imidazole group, triazole group, tetraazole group, azathiophene group, diazathiophene group, or triazathiophene group, and The second ring is an adamantyl group, norbornel group, norbornene group, cyclohexyl group, cyclohexene group, phenyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group.

6. The organometallic compound according to claim 1, CY1 and CY2 are each independently a phenyl group, a naphthol group, a 1,2,3,4-tetrahydronaphthol group, a phenanthrene group, a pyridine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthrene group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene group, an azirfluorene group, an azircarbazole group, an azirdibenzofuran group, an azirdibenzothiophene group, or an azirdibenzothiophene group.

7. The organometallic compound according to claim 1, Among them, by The part represented is any one of the groups represented by formulas 1-1 to 1-32: in, In equations 1-1 to 1-32, R 11 To R 14 Each independently as described in claim 1 for R 10 The described, and each is not hydrogen, Z1 is as described in claim 1. * indicates the binding site with M1, and * indicates a binding site with an adjacent atom.

8. The organometallic compound according to claim 1, Among them, by The represented part is any one of the groups represented by formulas 2-1 to 2-16: in, In equations 2-1 to 2-16, R 21 To R 24 Each independently as described in claim 1 for R 20 The described, and each is not hydrogen, *' indicates the binding site with M1, and * indicates a binding site with an adjacent atom.

9. The organometallic compound according to claim 1, Among them, R1 to R5, R 10 R 20 R 31 To R 34 and R 41 To R 47 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 Alkyl, or C1-C 20 Alkoxy; Each of the following C1-C is replaced: 20 Alkyl or C1-C 20 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof; Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroloyl, thiophenolyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, inzolyl, purinel, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxolinyl, quinazolinyl, cinolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophenolyl, benzoisothiazolyl, benzooxazolyl, benzoisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenolyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, or imidazopyrimidinyl; Each of the following substituted groups is replaced by: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrrolyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, inzolyl, purine, quinolinyl, isoquinolinyl, benzo[a]quinolinyl, quinoxolinyl, quinazolinyl, carbazoleyl, phenanthrololyl, benzimidazolyl, benzofuranyl, benzo[a]thiophenyl, benziisothiazolyl, benzo[a]oxazolyl, benziisooxazolyl, triazolyl Tetraazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indoleyl, inzolyl, purinel, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxolinyl, quinazolinyl, cinolinyl, carbazoleyl, phenanthrololinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzoisothiazolyl, benzooxazolyl, benzoisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, imidazopyridyl, imidazopyrimidinyl, or combinations thereof; or -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9), and Q1 through Q9 are each independent of the following: Deuterium, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or Each of the following is replaced by n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof.

10. The organometallic compound according to claim 1, Where R 31 To R 34 At least one of them is not hydrogen.

11. The organometallic compound according to claim 1, Where R 31 To R 34 At least one of the following is deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, Cl-C 60 Alkyl groups, or C1-C groups substituted with deuterium 60 alkyl.

12. The organometallic compound according to claim 1, The organometallic compound mentioned above is a compound represented by Formula 11: Formula 11 in, In Equation 11, M1, n1, n2, R1, R2, R 31 To R 34 R 41 To R 47 Y1 and Y2 are each as defined in claim 1. X 11 For C(Z1), C(R) 11 ), or N, X 12 For C(Z1), C(R) 12 ), or N, X 13 For C(Z1), C(R) 13 ), or N, and X 14 For C(Z1), C(R) 14 ), or N, X 11 To X 14 At least one of them is C(Z1), and Z1 is as defined in claim 1. R 11 To R 14 Each independently as described in claim 1 for R 10 Defined X 21 For C(R) 21 ) or N, X 22 For C(R) 22 ) or N, X 23 For C(R) 23 ) or N, and X 24 For C(R) 24 ) or N, R 21 To R 24 Each independently as described in claim 1 for R 20 Defined R 11 To R 14 Two or more of these may optionally combine with each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, and R 21 To R 24 Two or more of these may optionally combine with each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

13. The organometallic compound according to claim 1, The organometallic compound mentioned therein is a compound represented by any one of formulas 21-1 to 21-4: Equation 21-1 Equation 21-2 Equation 21-3 Equation 21-4 in, In equations 21-1 to 21-4, M1, n1, n2, R1, R2, R 31 To R 34 R 41 To R 47 Y1, Y2, and Z1 are each as defined in claim 1. R 11 To R 14 Each independently as described in claim 1 for R 10 Defined R 21 To R 24 Each independently as described in claim 1 for R 20 Defined R 11 To R 14 Two or more of these may optionally combine with each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, and R 21 To R 24 Two or more of these may optionally combine with each other to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

14. The organometallic compound according to claim 1, The organometallic compound mentioned above is any one of compounds 1 to 84:

15. Organic light-emitting devices, including: First electrode; Second electrode; as well as An organic layer, comprising an emission layer, is disposed between the first electrode and the second electrode. The organic layer comprises at least one organometallic compound according to any one of claims 1 to 14.

16. The organic light-emitting device according to claim 15, The at least one organometallic compound is included in the emitter layer.

17. The organic light-emitting device according to claim 16, The emitter layer further includes a body, and the amount of the body is greater than the amount of the at least one organometallic compound by weight.

18. The organic light-emitting device according to claim 16, The emitting layer emits green light with a maximum emission wavelength of 500 nm to 600 nm.

19. The organic light-emitting device according to claim 16, The first electrode is the anode. The second electrode is a cathode, and The organic layer further includes a hole transport region disposed between the first electrode and the emitter layer, and an electron transport region disposed between the emitter layer and the second electrode, wherein 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.

20. An electronic device, including an organic light-emitting device according to any one of claims 15 to 19.

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