Organometallic compound, organic light emitting device including the same and electronic device including the organic light emitting device

Abstract

An organometallic compound represented by the following chemical formula 1, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device are disclosed: M(L1)n1(L2)n2 The descriptions of M, L1, L2, n1, and n2 in Chemical Formula 1 above refer to those described in the present specification.

Description

Technology Field

[0001] An organometallic compound, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device are presented. Background Technology

[0002] Organic light-emitting devices are self-luminous devices that have excellent viewing angle, response time, brightness, driving voltage, and response speed, and can be multicolored.

[0003] According to one example, an organic light-emitting device may include an anode, a cathode, and an organic layer disposed between the anode and the cathode and including a light-emitting layer. A hole transport region may be provided between the anode and the light-emitting layer, and an electron transport region may be provided between the light-emitting layer and the cathode. Holes injected from the anode move to the light-emitting layer via the hole transport region, and electrons injected from the cathode move to the light-emitting layer via the electron transport region. The holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated as these excitons change from an excited state to a ground state. The problem to be solved

[0004] The present invention provides a novel organometallic compound, an organic light-emitting device employing the same, and an electronic device including said organic light-emitting device. means of solving the problem

[0005] According to one aspect, an organometallic compound represented by the following chemical formula 1 is provided:

[0006] <Chemical Formula 1>

[0007] M(L1) n1 (L2) n2

[0008] Among the above chemical formula 1,

[0009] M is a transition metal, and

[0010] L1 is a ligand represented by the following chemical formula 2, and

[0011] n1 is 1, 2, or 3, and if n1 is 2 or greater, 2 or more L1s are identical or different from each other, and

[0012] L2 is a monodentate ligand, bidentate ligand, tridentate ligand, or tetradentate ligand, and

[0013] n2 is 0, 1, 2, 3, or 4, and if n2 is 2 or greater, 2 or more L2s are identical or different from each other, and

[0014] L1 and L2 are different from each other,

[0015] <Chemical Formula 2> <Chemical Formula 3>

[0016]

[0017] X in the above chemical formula 2 11 is C, N, or C(R) bonded to X1 of Chemical Formula 3. 11 ) and, X 12 is C, N, or C(R) bonded to X1 or X2 of Chemical Formula 3. 12 ) and, X 13 C, N, or C(R) bonded to X1 or X2 of Chemical Formula 3 13 ) and, X 14 is C, N, or C(R) bonded to X2 of Chemical Formula 3. 14 ) and,

[0018] Among the above chemical formula 2, i) X 11 is C bonded to X1 of Chemical Formula 3, and X 12 is C bonded to X2 of Chemical Formula 3; ii) X 12 is C bonded to X1 of Chemical Formula 3, and X 13 is C bonded to X2 of Chemical Formula 3; or iii) X 13 is C bonded to X1 of Chemical Formula 3, and X 14is C bonded to X2 of Chemical Formula 3, and

[0019] In Chemical Formula 3, X1 is O, S, Se, B(R 31 ), N(R 31 ), C(R 31 )(R 32 ) or Si(R 31 )(R 32 ) and,

[0020] In Chemical Formula 3, X2 is O, S, Se, B(R 33 ), N(R 33 ), C(R 33 )(R 34 ) or Si(R 33 )(R 34 ) and,

[0021] Y1 is N, Y2 is C or N, and

[0022] Rings CY1 and CY2 are independent of each other, C5-C 30 Carbocyclic group or C1-C 30 It is a heterocyclic group, and

[0023] R1, R2, R 11 to R 14 and R 31 to R 34 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 A heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), wherein R 31 and R 33 It is not hydrogen,

[0024] a1 is an integer from 0 to 10, and if a1 is 2 or greater, 2 or more R1s are identical or different from each other, and

[0025] a2 is an integer from 0 to 20, and if a2 is 2 or greater, 2 or more R2 are identical or different from each other, and

[0026] In Chemical Formula 1, i) n2 is 0, and ii) X1 of Chemical Formula 3 is C(R 31 )(R 32 ) and iii) X2 of chemical formula 3 is C(R 33 )(R 34 Compounds that are ) are excluded,

[0027] Two or more of the multiple R1s are optionally connected to each other, such that at least one R 10a C5-C substituted or unsubstituted 30 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 30 It can form heterocyclic groups,

[0028] Two or more of the plurality of R2s are optionally connected to each other, such that at least one R 10a C5-C substituted or unsubstituted 30Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 30 It can form heterocyclic groups,

[0029] R 10a For an explanation regarding, refer to the explanation for R2 above, and

[0030] * and *' in Chemical Formula 2 are each binding sites with M in Chemical Formula 1, and

[0031] * and *' in Chemical Formula 3 are X in Chemical Formula 2, respectively. 11 To X 14 It is a combined site with 2 of them, and

[0032] The above-mentioned substituted C1-C 60 Alkyl groups, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 Alkoxy group, substituted C3-C 10 Cycloalkyl group, substituted C1-C 10 Heterocycloalkyl group, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C6-C 60 aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 The substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic heterocondensed polycyclic group are independent of each other,

[0033] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group or C1-C60 Alkoxygenation;

[0034] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -Ge(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ), or substituted with any combination thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group or C1-C 60 Alkoxygenation;

[0035] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -Ge(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), -P(Q 28 )(Q 29 ), or substituted or unsubstituted with any combination thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic group;

[0036] -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), -B(Q36 )(Q 37 ), -P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 ); or

[0037] Any combination of these;

[0038] And,

[0039] The above Q1 to Q9, Q 11 to Q 19 , Q 21 to Q 29 and Q 31 to Q 39 are independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; amido group; hydrazine group; hydrazone group; carboxylic acid group or salt thereof; sulfonic acid group or salt thereof; phosphate group or salt thereof; deuterium, C1-C 60 Alkyl group, C6-C 60 C1-C substituted or unsubstituted with an aryl group, or any combination thereof 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; C3-C 10 Cycloalkyl group; C1-C 10 Heterocycloalkyl group; C3-C 10 Cycloalkenyl group; C1-C 10 Heterocycloalkenyl group; deuterium, C1-C 60 Alkyl group, C6-C 60 C6-C6 substituted or unsubstituted with an aryl group, or any combination thereof 60 Aryl group; C6-C 60 Aryloxy group; C6-C 60 Arylthio group; C1-C 60 It is a heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic heterocondensed polycyclic group.

[0040] 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 a light-emitting layer, wherein the organic layer includes one or more organometallic compounds.

[0041] The above organometallic compound may be included in the light-emitting layer, and the organometallic compound included in the light-emitting layer may act as a dopant.

[0042] According to another aspect, an electronic device including the above-mentioned organic light-emitting element is provided. Effects of the invention

[0043] Since the above organometallic compound has excellent electrical properties, an electronic device employing the above organometallic compound, for example, an organic light-emitting device, may have improved driving voltage, current density, efficiency, power, color purity, and / or lifespan characteristics. Brief explanation of the drawing

[0044] FIG. 1 is a cross-sectional view schematically showing an organic light-emitting device according to one embodiment. Specific details for implementing the invention

[0045] The above organometallic compound is represented by the following chemical formula 1:

[0046] <Chemical Formula 1>

[0047] M(L1) n1 (L2) n2

[0048] In the above chemical formula 1, M may be a transition metal.

[0049] For example, the above M may be a first-period transition metal, a second-period transition metal, or a third-period transition metal.

[0050] As another example, the above M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0051] According to one embodiment, the above M may be Ir, Pt, Os, or Rh.

[0052] L1 in the above chemical formula 1 may be a ligand represented by the following chemical formula 2.

[0053] <Chemical Formula 2>

[0054]

[0055] Refer to the detailed description of the above chemical formula 2 as set forth in this specification.

[0056] In the above chemical formula 1, n1 represents the number of L1s and may be 1, 2, or 3. If n1 is 2 or more, the 2 or more L1s may be identical or different from each other. For example, n1 may be 1 or 2.

[0057] L2 in Chemical Formula 1 above may be a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand. For a detailed description of L2, refer to the description in this specification.

[0058] In the above chemical formula 1, n2 represents the number of L2s and may be 0, 1, 2, 3, or 4. If n2 is 2 or more, the 2 or more L2s may be identical or different from each other. For example, n2 may be 1 or 2.

[0059] L1 and L2 in the above chemical time 1 are different from each other.

[0060] According to one embodiment, in the above formula 1, i) M is Ir or Os and n1 + n2 is 3 or 4; or ii) M is Pt and n1 + n2 is 2.

[0061] According to another embodiment, among the above Chemical Formula 1,

[0062] M is Ir, and

[0063] n1 and n2 are independently 1 or 2, and

[0064] n1 + n2 can be 3.

[0065] X in the above chemical formula 2 11 C, N, or C(R) bonded (via a single bond) to X1 of Chemical Formula 3 below. 11 ) and, X 12 is C, N, or C(R) bonded (via a single bond) to X1 or X2 of the following chemical formula 3. 12 ) and, X 13 C, N, or C(R) bonded (via a single bond) to X1 or X2 of the following chemical formula 3. 13 ) and, X 14 is C, N, or C(R) bonded (via a single bond) to X2 of the following chemical formula 3. 14 ) may be. Here, among the above chemical formula 2, i) X 11 is C bonded (via a single bond) to X1 of Chemical Formula 3, and X 12 is C bonded (via a single bond) to X2 of Chemical Formula 3; ii) X 12 is C bonded (via a single bond) to X1 of Chemical Formula 3, and X 13 is C bonded (via a single bond) to X2 of Chemical Formula 3; or iii) X 13 is C bonded to X1 of Chemical Formula 3 (via a single bond), and X 14 can be C bonded to X2 of chemical formula 3 (through a single bond).

[0066] <Chemical Formula 3>

[0067]

[0068] That is, the group represented by the above chemical formula 3 is necessarily condensed into the group represented by the above chemical formula 2.

[0069] In the above chemical formula 3, X1 is O, S, Se, B(R 31), N(R 31 ), C(R 31 )(R 32 ) or Si(R 31 )(R 32 ) and X2 is O, S, Se, B(R 33 ), N(R 33 ), C(R 33 )(R 34 ) or Si(R 33 )(R 34 It can be.

[0070] According to one embodiment, at least one of X1 and X2 of the above chemical formula 3 may be O, S or Se.

[0071] According to another embodiment, X1 and X2 of the above chemical formula 3 may be identical to each other.

[0072] According to another embodiment, X1 and X2 of the above chemical formula 3 may be different from each other.

[0073] According to another embodiment, i) X1 in Chemical Formula 3 above is C(R 31 )(R 32 ) and X2 is O, S, Se, B(R 33 ), N(R 33 ), or Si(R 33 )(R 34 ) or; or ii) X1 is O, S, Se, B(R 31 ), N(R 31 ), or Si(R 31 )(R 32 ) and X2 is C(R 33 )(R 34 It can be.

[0074] In the above chemical formula 2, Y1 is N, and Y2 can be C or N. For example, Y2 in the above chemical formula 2 can be C.

[0075] The above chemical formulas 2 and 3, ring CY1 and ring CY2, are independently C5-C 30 Carbocyclic group or C1-C 30It can be a heterocyclic group.

[0076] For example, in the above chemical formulas 2 and 3, ring CY1 and ring CY2 are independently i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed together, iv) a condensed ring in which two or more second rings are condensed together, or v) a condensed ring in which one or more first rings and one or more second rings are condensed together, and

[0077] The first ring is a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silol group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzocilol group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiazole group, a thiatriazole group, an isothiazole group, a pyrazol group, an imidazole group, a triazole group, a tetrazole group, an azacilol group, a diazcilol group, or a triazcilol group, and

[0078] The second ring above may be an admantane group, a norbornane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0079] For example, the rings CY1 and CY2 in the above formulas 2 and 3 are independently of each other, cyclopentane group, cyclohexane group, cyclohectane group, cyclopentene group, cyclohexene group, cycloheptene group, admantane group, norbornane group, norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.2]octane group, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, 1,2,3,4-tetrahydronaphthalene group, pyrrole group, borol group, phosphol group, cyclopentadiene group, silol group, zemolar group, thiophene group, selenophene group, Furan group, Indole group, Benzobolol group, Benzophosphol group, Indene group, Benzocilol group, Benzogermol group, Benzothiophene group, Benzoselenopene group, Benzofuran group, Carbazole group, Dibenzoborol group, Dibenzophol group, Fluorene group, Dibenzocilol group, Dibenzagermol group, Dibenzothiophen group, Dibenzoselenopene group, Dibenzofuran group, Dibenzothiophen 5-oxide group, 9H-Fluorene-9-one group, Dibenzothiophen 5,5-dioxide group, Azaindole group, Azabenzoborol group, Azabenzophol group, Azaindene group, Azabenzocilol group, Azabenzagermol group, Azabenzothiophen group, Azabenzoselenopene group, Azabenzofuran group, Azacarbazole group, Azadibenzoborol group, Azadibenzophospol group, Azafluoren group, Azadibenzosilol group, Azadibenzozermol group, Azadibenzothiophene group, Azadibenzoselenophene group, Azadibenzofuran group, Azadibenzothiophene 5-oxide group, Aza-9H-fluoren-9-one group, Azadibenzothiophene 5,5-dioxide group, Pyridine group, Pyrimidine group, Pyrazine group, Pyridazine group, Triazine group, Quinoline group, Isoquinoline group, Benzoquinoline group, Benzoisoquinoline group, Quinoxaline group, Quinazoline group,It may be a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an azaborol group, azaphosphor group, azacyclopentadiene group, azacilol group, azazermol group, azaselenopene group, an oxazole group, an isooxazole group, a thiazole group, an isothiaazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiaazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

[0080] According to one embodiment, the ring CY1 of the above chemical formula 3 may be a benzene group, a pyridine group, or a pyrimidine group.

[0081] According to another embodiment, Y2 of the above formula 2 is C, and the ring CY2 of the above formula 2 may be a benzene group, a naphthalene group, a fluorene group, a dibenzofuran group, a dibenzothiophene group, or a carbazole group.

[0082] Among the above chemical formulas 2 and 3, R1, R2, and R 11 to R 14 and R 31 to R 34 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 A heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), wherein R 31 and R 33 It may not be hydrogen. Refer to the descriptions of Q1 to Q9 above as described in this specification.

[0083] For example, the above R1, R2, R 11 to R 14 and R 31 to R 34 are independently of each other,

[0084] Hydrogen, Deuterium, -F, -Cl, -Br, -I, Hydroxyl group, Cyano group, Nitro group, Amino group, Amidino group, Hydrazine group, Hydrazone group, Carboxylic acid group or its salt, Sulfonic acid group or its salt, Phosphate group or its salt, -SF5, C1-C 20 alkyl group or C1-C 20 Alkoxygenation;

[0085] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 20 Alkyl group, deuterated C1-C20 Alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norvonanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C1-C 20 Alkyl)cyclopentyl group, (C1-C 20 Alkyl)cyclohexyl group, (C1-C 20 Alkyl)cycloheptyl group, (C1-C 20 Alkyl)cyclooctyl group, (C1-C 20 Alkyl)adamantanyl group, (C1-C 20 Alkyl)norbonanyl group, (C1-C 20 Alkyl)norborneyl group, (C1-C 20 Alkyl)cyclopentenyl group, (C1-C 20 Alkyl)cyclohexenyl group, (C1-C 20 Alkyl)cycloheptenyl group, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 Substituted with an alkyl phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, pyridinyl group, pyrimidinyl group, or any combination thereof, C1-C 20 alkyl group or C1-C 20 Alkoxygenation;

[0086] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 20 Alkyl group, deuterated C1-C 20 Alkyl group, C1-C 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norvonanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C1-C 20 Alkyl)cyclopentyl group, (C1-C 20 Alkyl)cyclohexyl group, (C1-C 20 Alkyl)cycloheptyl group, (C1-C 20 Alkyl)cyclooctyl group, (C1-C 20 Alkyl)adamantanyl group, (C1-C 20 Alkyl)norbonanyl group, (C1-C 20 Alkyl)norborneyl group, (C1-C 20 Alkyl)cyclopentenyl group, (C1-C 20 Alkyl)cyclohexenyl group, (C1-C 20 Alkyl)cycloheptenyl group, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrroleyl group, thiophenyl group, furanyl group, imidazoleyl group, pyrazolyl group, thiazoleyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indoleyl group, indazoleyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazoleyl group, phenanthrolinyl group, Benzoimidazoleyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazoleyl group, benzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, oxadiazoleyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, imidazopyrimidinyl group, imidazopyrimidinyl group, azacarbazoleyl group, azadibenzofuranyl group, azadibenzothiophenyl group, or any combination thereof substituted or unsubstituted, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norvonanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, cycloheptenyl group, Bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrroleyl group, thiophenyl group, furanyl group, imidazoleyl group, pyrazolyl group, thiazoleyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indoleyl group, indazoleyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazoleyl group, phenanthrolinyl group, Benzimidazoleyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazoleyl group, benzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazoleyl group, oxadiazoleyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, imidazopyridinyl group, imidazopyridinyl group, azacarbazoleyl group, azadibenzofuranyl group or azadibenzothiophenyl group; or

[0087] -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9) or -P(Q8)(Q9);

[0088] And,

[0089] Q1 to Q9 are independent of each other,

[0090] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H or -CD2CDH2; or

[0091] Deuterium, C1-C 20 Substituted or unsubstituted with an alkyl group, a phenyl group, or any combination thereof, n -Propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group,n -Pentyl, tert -Pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -Isopentyl group, phenyl group, biphenyl group, or naphthyl group;

[0092] It could be.

[0093] As another example, the above R1, R2, R 11 to R 14 and R 31 to R 34 are independently hydrogen, deuterium, -F, cyano group, nitro group, -SF5, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by one of the following chemical formulas 9-1 to 9-66, a group in which at least one hydrogen in one of the following chemical formulas 9-1 to 9-66 is substituted with deuterium, a group represented by one of the following chemical formulas 10-1 to 10-118, a group in which at least one hydrogen in one of the following chemical formulas 10-1 to 10-118 is substituted with deuterium, a group represented by one of the following chemical formulas 10-201 to 10-342, a group in which at least one hydrogen in one of the following chemical formulas 10-201 to 10-342 is substituted with deuterium, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5) (the description of Q3 to Q5 is as follows (Refer to what is described in this specification) it may be:

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] In the above chemical formulas 9-1 to 9-66, 10-1 to 10-118 and 10-201 to 10-342, * is a bonding site with an adjacent atom, Ph is a phenyl group, and TMS is a trimethylsilyl group.

[0111] The "group in which at least one hydrogen of chemical formulas 9-1 to 9-66 is substituted with deuterium" may be, for example, a group represented by one of the following chemical formulas 9-501 to 9-514 and 9-601 to 9-638:

[0112]

[0113]

[0114]

[0115] The above "group in which at least one hydrogen of chemical formulas 10-1 to 10-118 is substituted with deuterium" may be, for example, a group represented by one of the following chemical formulas 10-501 to 10-546.

[0116]

[0117]

[0118]

[0119] In the above chemical formula 3, a1 represents the number of R1s and may be an integer from 0 to 10. If a1 is 2 or more, the 2 or more R1s may be identical or different from each other. For example, a1 may be 0, 1, or 2.

[0120] In the above chemical formula 2, a2 ​​represents the number of R2 and may be an integer from 0 to 20. If a2 is 2 or more, the 2 or more R2 may be identical or different from each other. For example, a2 may be an integer from 0 to 10.

[0121] According to one embodiment, L1 in Formula 1 may be a ligand represented by the following Formulas 2-1, 2-2, or 2-3:

[0122]

[0123] Among the above chemical formulas 2-1 to 2-3,

[0124] X 11 is N or C(R 11 ) and, X 12 is N or C(R 12 ) and, X 13 is N or C(R 13 ) and, X 14 is N or C(R 14 ) and,

[0125] X1, X2, Y1, Y2, loop CY1, loop CY2, R1, R2, R 11 to R 14 Descriptions of , a1, a2, * and *' are each referred to as described in this specification.

[0126] According to another embodiment, L1 in Formula 1 is a ligand represented by Formula 2-3, and

[0127] X in the above chemical formula 2-3 12 is C(R 12 ) and,

[0128] The above R 12It can be -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5).

[0129] According to another embodiment, L1 in Formula 1 may be a ligand represented by the following Formulas 2-1(1), 2-2(1), or 2-3(1):

[0130]

[0131] Among the above chemical formulas 2-1(1) to 2-3(1), X1, X2, Y1, Y2, ring CY2, R1, R2, R 11 to R 14 Descriptions of , a1, a2, * and *' are each referred to as described in this specification.

[0132] According to another embodiment, among the above chemical formula 2 The group represented by may be a group represented by one of the following chemical formulas CY2-1 to CY2-31:

[0133]

[0134]

[0135]

[0136]

[0137] Among the above chemical formulas CY2-1 to CY2-31,

[0138] Refer to the descriptions of Y2 and R2 as set forth in this specification, respectively.

[0139] X 22 is C(R 22 )(R 23 ), N(R 22 ), O, S or Si(R 22 )(R 23 ) and,

[0140] R 22 to R 29 For descriptions of each, refer to the description of R2 in this specification, and

[0141] a26 is an integer from 0 to 6, and

[0142] a25 is an integer from 0 to 5, and

[0143] a24 is an integer from 0 to 4, and

[0144] a23 is an integer from 0 to 3, and

[0145] a22 is an integer from 0 to 2, and

[0146] *" is a bonding site with an adjacent atom in Chemical Formula 2, and

[0147] * is the binding site with M in Chemical Formula 1.

[0148] Meanwhile, L2 in the above chemical formula 1 may be a bidentate ligand that is bonded to M of the above chemical formula 1 through O, S, N, C, P, Si, or As.

[0149] According to one embodiment, L2 in the above formula 1 may be a bidentate ligand that is bonded to M of the above formula 1 through N and C, respectively.

[0150] According to another embodiment, L2 in Formula 1 may be a group represented by one of the following Formulas 3A to 3F:

[0151]

[0152] Among the above chemical formulas 3A to 3F,

[0153] Y 13 is O, N, N(Z1), P(Z1)(Z2) or As(Z1)(Z2), and

[0154] Y 14 is O, N, N(Z3), P(Z3)(Z4) or As(Z3)(Z4), and

[0155] T 11 single bond, double bond, *-C(Z 11 )(Z 12 )-*', *-C(Z 11 )=C(Z 12)-*', *=C(Z 11 )-*', *-C(Z 11 )=*', *=C(Z 11 )-C(Z 12 )=C(Z 13 )-*', *-C(Z 11 )=C(Z 12 )-C(Z 13 )=*', *-N(Z 11 )-*' or at least one Z 11 C5-C substituted or unsubstituted 30 It is a cabocyclic group, and

[0156] a11 is an integer from 1 to 10, and if a11 is 2 or more, then 2 or more T 11 They are identical or different from each other,

[0157] Y 11 and Y 12 are independently C or N, and

[0158] T 21 Silver consists of single bonds, double bonds, O, S, and C (Z 11 )(Z 12 ), Si(Z 11 )(Z 12 ) or N(Z 11 ) and,

[0159] Gori CY 11 and ring CY 12 are independently of each other, C5-C 30 Carbocyclic group or C1-C 30 It is a heterocyclic group, and

[0160] A1 is P or As, and

[0161] Z1 to Z4 and Z 11 To Z 13 For descriptions of each, refer to the description of R2 in this specification, and

[0162] d1 and d2 are independently integers from 0 to 10, and

[0163] * and *' are binding sites with M in the above chemical formula 1.

[0164] For example, of the above chemical formula 3D The group represented by is a group represented by one of the following chemical formulas CY11-1 to CY11-34 (or),

[0165] of the above chemical formulas 3C and 3D The group represented by may be a group represented by one of the following chemical formulas CY12-1 to CY12-34:

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174] Among the above chemical formulas CY11-1 to CY11-34 and CY12-1 to CY12-34,

[0175] X 31 is O, S, N(Z 11 ), C(Z 11 )(Z 12 ) or Si(Z 11 )(Z 12 ) and,

[0176] X 41 is O, S, N(Z 21 ), C(Z 21 )(Z 22 ) or Si(Z 21 )(Z 22 ) and,

[0177] Y 11 , Y 12 Descriptions of , Z1 and Z2 refer to those described in this specification, and

[0178] Z 11 To Z 18 and Z 21 To Z 28 For descriptions of each, refer to the description of R1 in this specification, and

[0179] d12 and d22 are independently integers from 0 to 2, and

[0180] d13 and d23 are independently integers from 0 to 3, and

[0181] d14 and d24 are independently integers from 0 to 4, and

[0182] d15 and d25 are independently integers from 0 to 5, and

[0183] d16 and d26 are independently integers from 0 to 6, and

[0184] In the above chemical formulas CY11-1 to CY11-34 and CY12-1 to CY12-34, * and *' are each binding sites with M in Chemical Formula 1, and *" is an adjacent atom in Chemical Formula 3C or T in Chemical Formula 3D. 21 It is a combination site with.

[0185] According to another embodiment, L2 in Formula 1 is a ligand represented by Formula 3D, and at least one of Z1 and Z2 of Formula 3D is independently substituted with deuterium; -Si(Q3)(Q4)(Q5); -Ge(Q3)(Q4)(Q5); or at least one deuterium C1-C 60 It can be an alkyl group.

[0186] According to another embodiment, the L2 may be a ligand represented by one of the following chemical formulas 3-1 and 3-101 to 3-112:

[0187]

[0188]

[0189] Among the above chemical formulas 3-1 and 3-101 to 3-112,

[0190] Y 11 , Y 12 , loop CY 12 , Z1 to Z4, Z 11 To Z 13 Refer to the descriptions of and d2 as set forth in this specification, respectively, and

[0191] Z 14 The description of Z in this specification 11 Refer to the explanation for,

[0192] e2 is an integer from 0 to 2, and

[0193] e3 is an integer from 0 to 3, and

[0194] e4 is an integer from 0 to 4, and

[0195] * and *' are each binding sites with M in Chemical Formula 1.

[0196] For example, Z in the above chemical formula 3-1 12 -Si(Q3)(Q4)(Q5); -Ge(Q3)(Q4)(Q5); or deuteriumized C1-C 60 It can be an alkyl group.

[0197] As another example, Z in the above chemical formula 3-1 12 is -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), and Z 13 It may not be hydrogen and methyl groups.

[0198] According to another embodiment, among the above chemical formula 3-1 The group represented by is a group represented by one of the following chemical formulas 3-1-1 to 3-1-16 (or is a group),

[0199] Among the above chemical formula 3-1 The group represented by may be a group represented by one of the following chemical formulas 3-1(1) to 3-1(16):

[0200]

[0201]

[0202]

[0203]

[0204] Among the above chemical formulas 3-1-1 to 3-1-16 and 3-1(1) to 3-1(16),

[0205] Z 11 To Z 14 For descriptions of each, refer to those described in this specification, and Z 21 To Z 24 The descriptions for each of the following are Z in this specification. 11 Refer to the explanation for Z 11 To Z 14 and Z 21 To Z 24 is not hydrogen,

[0206] * and *' are respectively binding sites with M in Chemical Formula 1, and

[0207] *" is a bonding site with a neighboring atom.

[0208] In Chemical Formula 1, i) n2 is 0, and ii) X1 of Chemical Formula 3 is C(R 31 )(R 32 ) and iii) X2 of chemical formula 3 is C(R 33 )(R 34 Compounds that are ) are excluded.

[0209] In the above Chemical Formula 1, i) at least two of the plurality of R1s are optionally connected to each other, such that at least one R 10a C5-C substituted or unsubstituted 30 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 30 ii) can form a heterocyclic group, and at least two of the plurality of R2 are optionally connected to each other, such that at least one R 10a C5-C substituted or unsubstituted 30Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 30 It can form heterocyclic groups.

[0210] R in this specification 10a For a description of, refer to the description of R2 in this specification.

[0211] * and *' in the above chemical formula 2 are each binding sites with M in chemical formula 1.

[0212] * and *' in the above Chemical Formula 3 are respectively X in Chemical Formula 2 11 To X 14 It is a combined site with 2 of them.

[0213] For example, the organometallic compound represented by the above chemical formula 1 may be one of the following compounds 1 to 289:

[0214]

[0215]

[0216] Compounds 10 to 289 are represented by the above formula 1, wherein M is Ir, L2 is a phenyl-pyridine ligand, and L1, n1, and n2 are compounds as defined in Tables 2 to 9 below, respectively. In Tables 1 to 8 below, Ph is a phenyl group, Me is a methyl group, and TMS is a tri(methyl)silyl group, and CY2-1(1) and CY2-1(2) refer to the following formulas:

[0217]

[0218] In the above chemical formulas CY2-1(1) and CY2-1(2), * is the bonding site with M in chemical formula 1, and *" is the bonding site with an adjacent atom.

[0219] No. L1 n1 n2 화학식 2-1(1) Y1 X1 X2 R1 R 13 , R 14 10 N O O H H CY2-1(1) 1 2 11 N O S H H CY2-1(1) 1 2 12 N O Se H H CY2-1(1) 1 2 13 N O N(Ph) H H CY2-1(1) 1 2 14 N O C(Me)2 H H CY2-1(1) 1 2 15 N O Si(Me)2 H H CY2-1(1) 1 2 16 N S O H H CY2-1(1) 1 2 17 N S S H H CY2-1(1) 1 2 18 N S Se H H CY2-1(1) 1 2 19 N S N(Ph) H H CY2-1(1) 1 2 20 N S C(Me)2 H H CY2-1(1) 1 2 21 N S Si(Me)2 H H CY2-1(1) 1 2 22 N C(Me)2 O H H CY2-1(1) 1 2 23 N C(Me)2 S H H CY2-1(1) 1 2 24 N C(Me)2 Se H H CY2-1(1) 1 2 25 N C(Me)2 N(Ph) H H CY2-1(1) 1 2 26 N C(Me)2 C(Me)2 H H CY2-1(1) 1 2 27 N C(Me)2 Si(Me)2 H H CY2-1(1) 1 2 28 N O O H H CY2-1(2) 1 2 29 N O S H H CY2-1(2) 1 2 30 N O Se H H CY2-1(2) 1 2 31 N O N(Ph) H H CY2-1(2) 1 2 32 N O C(Me)2 H H CY2-1(2) 1 2 33 N O Si(Me)2 H H CY2-1(2) 1 2 34 N S O H H CY2-1(2) 1 2 35 N S S H H CY2-1(2) 1 2 36 N S Se H H CY2-1(2) 1 2 37 N S N(Ph) H H CY2-1(2) 1 2 38 N S C(Me)2 H H CY2-1(2) 1 2 39 N S Si(Me)2 H H CY2-1(2) 1 2 40 N C(Me)2 O H H CY2-1(2) 1 2 41 N C(Me)2 S H H CY2-1(2) 1 2 42 N C(Me)2 Se H H CY2-1(2) 1 2 43 N C(Me)2 N(Ph) H H CY2-1(2) 1 2 44 N C(Me)2 C(Me)2 H H CY2-1(2) 1 2 45 N C(Me)2 Si(Me)2 H H CY2-1(2) 1 2

[0220] No. L1 n1 n2 화학식 2-1(1) Y1 X1 X2 R1 R 13 , R 14 46 N O O H H CY2-1(1) 2 1 47 N O S H H CY2-1(1) 2 1 48 N O Se H H CY2-1(1) 2 1 49 N O N(Ph) H H CY2-1(1) 2 1 50 N O C(Me)2 H H CY2-1(1) 2 1 51 N O Si(Me)2 H H CY2-1(1) 2 1 52 N S O H H CY2-1(1) 2 1 53 N S S H H CY2-1(1) 2 1 54 N S Se H H CY2-1(1) 2 1 55 N S N(Ph) H H CY2-1(1) 2 1 56 N S C(Me)2 H H CY2-1(1) 2 1 57 N S Si(Me)2 H H CY2-1(1) 2 1 58 N C(Me)2 O H H CY2-1(1) 2 1 59 N C(Me)2 S H H CY2-1(1) 2 1 60 N C(Me)2 Se H H CY2-1(1) 2 1 61 N C(Me)2 N(Ph) H H CY2-1(1) 2 1 62 N C(Me)2 C(Me)2 H H CY2-1(1) 2 1 63 N C(Me)2 Si(Me)2 H H CY2-1(1) 2 1 64 N O O H H CY2-1(2) 2 1 65 N O S H H CY2-1(2) 2 1 66 N O Se H H CY2-1(2) 2 1 67 N O N(Ph) H H CY2-1(2) 2 1 68 N O C(Me)2 H H CY2-1(2) 2 1 69 N O Si(Me)2 H H CY2-1(2) 2 1 70 N S O H H CY2-1(2) 2 1 71 N S S H H CY2-1(2) 2 1 72 N S Se H H CY2-1(2) 2 1 73 N S N(Ph) H H CY2-1(2) 2 1 74 N S C(Me)2 H H CY2-1(2) 2 1 75 N S Si(Me)2 H H CY2-1(2) 2 1 76 N C(Me)2 O H H CY2-1(2) 2 1 77 N C(Me)2 S H H CY2-1(2) 2 1 78 N C(Me)2 Se H H CY2-1(2) 2 1 79 N C(Me)2 N(Ph) H H CY2-1(2) 2 1 80 N C(Me)2 C(Me)2 H H CY2-1(2) 2 1 81 N C(Me)2 Si(Me)2 H H CY2-1(2) 2 1

[0221] No. L1 n1 n2 chemistry 2-2(1) Y1 X1 X2 R1 R 11 , R 14 1 N O O H H CY2-1(1) 1 2 82 N O S H H CY2-1(1) 1 2 83 N O See H H CY2-1(1) 1 2 84 N O N(Ph) H H CY2-1(1) 1 2 2 N O C(Me)2 H H CY2-1(1) 1 2 85 N O Si(Me)2 H H CY2-1(1) 1 2 86 N S O H H CY2-1(1) 1 2 87 N S S H H CY2-1(1) 1 2 88 N S See H H CY2-1(1) 1 2 89 N S N(Ph) H H CY2-1(1) 1 2 90 N S C(Me)2 H H CY2-1(1) 1 2 91 N S Si(Me)2 H H CY2-1(1) 1 2 92 N C(Me)2 O H H CY2-1(1) 1 2 93 N C(Me)2 S H H CY2-1(1) 1 2 94 N C(Me)2 See H H CY2-1(1) 1 2 95 N C(Me)2 N(Ph) H H CY2-1(1) 1 2 96 N C(Me)2 C(Me)2 H H CY2-1(1) 1 2 97 N C(Me)2 Si(Me)2 H H CY2-1(1) 1 2 98 N O O H H CY2-1(2) 1 2 99 N O S H H CY2-1(2) 1 2 100 N O See H H CY2-1(2) 1 2 101 N O N(Ph) H H CY2-1(2) 1 2 102 N O C(Me)2 H H CY2-1(2) 1 2 103 N O Si(Me)2 H H CY2-1(2) 1 2 104 N S O H H CY2-1(2) 1 2 105 N S S H H CY2-1(2) 1 2 106 N S See H H CY2-1(2) 1 2 107 N S N(Ph) H H CY2-1(2) 1 2 108 N S C(Me)2 H H CY2-1(2) 1 2 109 N S Si(Me)2 H H CY2-1(2) 1 2 3 N C(Me)2 O H H CY2-1(2) 1 2 110 N C(Me)2 S H H CY2-1(2) 1 2 111 N C(Me)2 See H H CY2-1(2) 1 2 112 N C(Me)2 N(Ph) H H CY2-1(2) 1 2 113 N C(Me)2 C(Me)2 H H CY2-1(2) 1 2 114 N C(Me)2 Si(Me)2 H H CY2-1(2) 1 2

[0222] No. L1 n1 n2 chemistry 2-2(1) Y1 X1 X2 R1 R 11 , R 14 115 N O O H H CY2-1(1) 2 1 116 N O S H H CY2-1(1) 2 1 117 N O See H H CY2-1(1) 2 1 118 N O N(Ph) H H CY2-1(1) 2 1 119 N O C(Me)2 H H CY2-1(1) 2 1 120 N O Si(Me)2 H H CY2-1(1) 2 1 121 N S O H H CY2-1(1) 2 1 122 N S S H H CY2-1(1) 2 1 123 N S See H H CY2-1(1) 2 1 124 N S N(Ph) H H CY2-1(1) 2 1 125 N S C(Me)2 H H CY2-1(1) 2 1 126 N S Si(Me)2 H H CY2-1(1) 2 1 127 N C(Me)2 O H H CY2-1(1) 2 1 128 N C(Me)2 S H H CY2-1(1) 2 1 129 N C(Me)2 See H H CY2-1(1) 2 1 130 N C(Me)2 N(Ph) H H CY2-1(1) 2 1 131 N C(Me)2 C(Me)2 H H CY2-1(1) 2 1 132 N C(Me)2 Si(Me)2 H H CY2-1(1) 2 1 133 N O O H H CY2-1(2) 2 1 134 N O S H H CY2-1(2) 2 1 135 N O See H H CY2-1(2) 2 1 136 N O N(Ph) H H CY2-1(2) 2 1 137 N O C(Me)2 H H CY2-1(2) 2 1 138 N O Si(Me)2 H H CY2-1(2) 2 1 139 N S O H H CY2-1(2) 2 1 140 N S S H H CY2-1(2) 2 1 141 N S See H H CY2-1(2) 2 1 142 N S N(Ph) H H CY2-1(2) 2 1 143 N S C(Me)2 H H CY2-1(2) 2 1 144 N S Si(Me)2 H H CY2-1(2) 2 1 145 N C(Me)2 O H H CY2-1(2) 2 1 146 N C(Me)2 S H H CY2-1(2) 2 1 147 N C(Me)2 See H H CY2-1(2) 2 1 148 N C(Me)2 N(Ph) H H CY2-1(2) 2 1 149 N C(Me)2 C(Me)2 H H CY2-1(2) 2 1 150 N C(Me)2 Si(Me)2 H H CY2-1(2) 2 1

[0223] No. L1 n1 n2 Chemistry 2-3(1) Y1 X1 X2 R1 R 11 , R 12 4 N O O H H CY2-1(1) 1 2 6 N O S H H CY2-1(1) 1 2 151 N O See H H CY2-1(1) 1 2 152 N O N(Ph) H H CY2-1(1) 1 2 153 N O C(Me)2 H H CY2-1(1) 1 2 154 N O Si(Me)2 H H CY2-1(1) 1 2 155 N S O H H CY2-1(1) 1 2 156 N S S H H CY2-1(1) 1 2 157 N S See H H CY2-1(1) 1 2 158 N S N(Ph) H H CY2-1(1) 1 2 159 N S C(Me)2 H H CY2-1(1) 1 2 160 N S Si(Me)2 H H CY2-1(1) 1 2 161 N C(Me)2 O H H CY2-1(1) 1 2 162 N C(Me)2 S H H CY2-1(1) 1 2 163 N C(Me)2 See H H CY2-1(1) 1 2 164 N C(Me)2 N(Ph) H H CY2-1(1) 1 2 165 N C(Me)2 C(Me)2 H H CY2-1(1) 1 2 166 N C(Me)2 Si(Me)2 H H CY2-1(1) 1 2 167 N O O H H CY2-1(2) 1 2 168 N O S H H CY2-1(2) 1 2 169 N O See H H CY2-1(2) 1 2 170 N O N(Ph) H H CY2-1(2) 1 2 171 N O C(Me)2 H H CY2-1(2) 1 2 172 N O Si(Me)2 H H CY2-1(2) 1 2 173 N S O H H CY2-1(2) 1 2 174 N S S H H CY2-1(2) 1 2 175 N S See H H CY2-1(2) 1 2 176 N S N(Ph) H H CY2-1(2) 1 2 177 N S C(Me)2 H H CY2-1(2) 1 2 178 N S Si(Me)2 H H CY2-1(2) 1 2 179 N C(Me)2 O H H CY2-1(2) 1 2 180 N C(Me)2 S H H CY2-1(2) 1 2 181 N C(Me)2 See H H CY2-1(2) 1 2 182 N C(Me)2 N(Ph) H H CY2-1(2) 1 2 183 N C(Me)2 C(Me)2 H H CY2-1(2) 1 2 184 N C(Me)2 Si(Me)2 H H CY2-1(2) 1 2

[0224] No. L1 n1 n2 Chemistry 2-3(1) Y1 X1 X2 R1 R 11 , R 12 5 N O O H H CY2-1(1) 2 1 185 N O S H H CY2-1(1) 2 1 186 N O See H H CY2-1(1) 2 1 187 N O N(Ph) H H CY2-1(1) 2 1 188 N O C(Me)2 H H CY2-1(1) 2 1 189 N O Si(Me)2 H H CY2-1(1) 2 1 190 N S O H H CY2-1(1) 2 1 191 N S S H H CY2-1(1) 2 1 192 N S See H H CY2-1(1) 2 1 193 N S N(Ph) H H CY2-1(1) 2 1 194 N S C(Me)2 H H CY2-1(1) 2 1 195 N S Si(Me)2 H H CY2-1(1) 2 1 196 N C(Me)2 O H H CY2-1(1) 2 1 197 N C(Me)2 S H H CY2-1(1) 2 1 198 N C(Me)2 See H H CY2-1(1) 2 1 199 N C(Me)2 N(Ph) H H CY2-1(1) 2 1 200 N C(Me)2 C(Me)2 H H CY2-1(1) 2 1 201 N C(Me)2 Si(Me)2 H H CY2-1(1) 2 1 202 N O O H H CY2-1(2) 2 1 203 N O S H H CY2-1(2) 2 1 204 N O See H H CY2-1(2) 2 1 205 N O N(Ph) H H CY2-1(2) 2 1 206 N O C(Me)2 H H CY2-1(2) 2 1 207 N O Si(Me)2 H H CY2-1(2) 2 1 208 N S O H H CY2-1(2) 2 1 209 N S S H H CY2-1(2) 2 1 210 N S See H H CY2-1(2) 2 1 211 N S N(Ph) H H CY2-1(2) 2 1 212 N S C(Me)2 H H CY2-1(2) 2 1 213 N S Si(Me)2 H H CY2-1(2) 2 1 214 N C(Me)2 O H H CY2-1(2) 2 1 215 N C(Me)2 S H H CY2-1(2) 2 1 216 N C(Me)2 See H H CY2-1(2) 2 1 217 N C(Me)2 N(Ph) H H CY2-1(2) 2 1 218 N C(Me)2 C(Me)2 H H CY2-1(2) 2 1 219 N C(Me)2 Si(Me)2 H H CY2-1(2) 2 1

[0225] No. L1 n1 n2 Chemistry 2-3(1) Y1 X1 X2 R 12 R1, R 11 7 N O O TMS H CY2-1(1) 1 2 220 N O S TMS H CY2-1(1) 1 2 221 N O Se TMS H CY2-1(1) 1 2 222 N O N(Ph) TMS H CY2-1(1) 1 2 223 N O C(Me)2 TMS H CY2-1(1) 1 2 224 N O Si(Me)2 TMS H CY2-1(1) 1 2 225 N S O TMS H CY2-1(1) 1 2 226 N S S TMS H CY2-1(1) 1 2 227 N S Se TMS H CY2-1(1) 1 2 228 N S N(Ph) TMS H CY2-1(1) 1 2 229 N S C(Me)2 TMS H CY2-1(1) 1 2 230 N S Si(Me)2 TMS H CY2-1(1) 1 2 231 N C(Me)2 O TMS H CY2-1(1) 1 2 232 N C(Me)2 S TMS H CY2-1(1) 1 2 233 N C(Me)2 Se TMS H CY2-1(1) 1 2 234 N C(Me)2 N(Ph) TMS H CY2-1(1) 1 2 235 N C(Me)2 C(Me)2 TMS H CY2-1(1) 1 2 236 N C(Me)2 Si(Me)2 TMS H CY2-1(1) 1 2 237 N O O TMS H CY2-1(2) 1 2 238 N O S TMS H CY2-1(2) 1 2 239 N O Se TMS H CY2-1(2) 1 2 240 N O N(Ph) TMS H CY2-1(2) 1 2 241 N O C(Me)2 TMS H CY2-1(2) 1 2 242 N O Si(Me)2 TMS H CY2-1(2) 1 2 243 N S O TMS H CY2-1(2) 1 2 244 N S S TMS H CY2-1(2) 1 2 245 N S Se TMS H CY2-1(2) 1 2 246 N S N(Ph) TMS H CY2-1(2) 1 2 247 N S C(Me)2 TMS H CY2-1(2) 1 2 248 N S Si(Me)2 TMS H CY2-1(2) 1 2 249 N C(Me)2 O TMS H CY2-1(2) 1 2 250 N C(Me)2 S TMS H CY2-1(2) 1 2 251 N C(Me)2 Se TMS H CY2-1(2) 1 2 252 N C(Me)2 N(Ph) TMS H CY2-1(2) 1 2 253 N C(Me)2 C(Me)2 TMS H CY2-1(2) 1 2 254 N C(Me)2 Si(Me)2 TMS H CY2-1(2) 1 2

[0226] No. L1 n1 n2 화학식 2-3(1) Y1 X1 X2 R 12 R1, R 11 8 N O O TMS H CY2-1(1) 2 1 255 N O S TMS H CY2-1(1) 2 1 256 N O Se TMS H CY2-1(1) 2 1 257 N O N(Ph) TMS H CY2-1(1) 2 1 258 N O C(Me)2 TMS H CY2-1(1) 2 1 259 N O Si(Me)2 TMS H CY2-1(1) 2 1 260 N S O TMS H CY2-1(1) 2 1 261 N S S TMS H CY2-1(1) 2 1 262 N S Se TMS H CY2-1(1) 2 1 263 N S N(Ph) TMS H CY2-1(1) 2 1 264 N S C(Me)2 TMS H CY2-1(1) 2 1 265 N S Si(Me)2 TMS H CY2-1(1) 2 1 266 N C(Me)2 O TMS H CY2-1(1) 2 1 267 N C(Me)2 S TMS H CY2-1(1) 2 1 268 N C(Me)2 Se TMS H CY2-1(1) 2 1 269 N C(Me)2 N(Ph) TMS H CY2-1(1) 2 1 270 N C(Me)2 C(Me)2 TMS H CY2-1(1) 2 1 271 N C(Me)2 Si(Me)2 TMS H CY2-1(1) 2 1 272 N O O TMS H CY2-1(2) 2 1 273 N O S TMS H CY2-1(2) 2 1 274 N O Se TMS H CY2-1(2) 2 1 275 N O N(Ph) TMS H CY2-1(2) 2 1 276 N O C(Me)2 TMS H CY2-1(2) 2 1 277 N O Si(Me)2 TMS H CY2-1(2) 2 1 278 N S O TMS H CY2-1(2) 2 1 279 N S S TMS H CY2-1(2) 2 1 280 N S Se TMS H CY2-1(2) 2 1 281 N S N(Ph) TMS H CY2-1(2) 2 1 282 N S C(Me)2 TMS H CY2-1(2) 2 1 283 N S Si(Me)2 TMS H CY2-1(2) 2 1 284 N C(Me)2 O TMS H CY2-1(2) 2 1 285 N C(Me)2 S TMS H CY2-1(2) 2 1 286 N C(Me)2 Se TMS H CY2-1(2) 2 1 287 N C(Me)2 N(Ph) TMS H CY2-1(2) 2 1 288 N C(Me)2 C(Me)2 TMS H CY2-1(2) 2 1 289 N C(Me)2 Si(Me)2 TMS H CY2-1(2) 2 1

[0227] Among the organometallic compounds represented by Chemical Formula 1, L1 is a ligand represented by Chemical Formula 2, and the number of L1s, n1, is 1, 2, or 3. That is, the organometallic compound is a ligand bonded to metal M and necessarily includes at least one ligand represented by Chemical Formula 2. An electronic device employing such an organometallic compound represented by Chemical Formula 1, for example, an organic light-emitting device, can have an improved driving voltage and an improved external quantum efficiency.

[0228] The results of evaluating the HOMO energy level, LUMO energy level, and T1 energy level of some of the organometallic compounds represented by Chemical Formula 1 above using the Gaussian 09 program, which involves molecular structure optimization based on density functional theory (DFT) based on B3LYP, are as shown in Table 9 below.

[0229] Compound No. HOMO(eV) LUMO(eV) T1(eV) 1 -4.840 -1.238 2.573 2 -4.841 -1.304 2.556 3 -4.809 -1.166 2.632 4 -4.832 -1.208 2.616 5 -4.806 -1.200 2.609 6 -4.865 -1.228 2.592 7 -4.812 -1.246 2.561 8 -4.765 -1.236 2.553 9 -4.823 -1.247 2.583

[0230] From Table 1 above, it can be confirmed that the organometallic compound represented by Chemical Formula 1 has electrical properties suitable for use as a dopant in the light-emitting layer of an electronic device, for example, an organic light-emitting device.

[0231] A method for synthesizing an organometallic compound represented by the above chemical formula 1 can be recognized by those skilled in the art by referring to the synthesis examples described below.

[0232] Accordingly, the organometallic compound represented by the above chemical formula 1 may be suitable for use as a dopant in the organic layer of an organic light-emitting device, for example, in the light-emitting layer among the organic layers. 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 a light-emitting layer, wherein the organic layer comprises at least one organometallic compound represented by the above chemical formula 1.

[0233] The above organic light-emitting device can have low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, low roll-off ratio, and excellent color purity by having an organic layer containing an organometallic compound represented by Chemical Formula 1 as described above.

[0234] The organometallic compound represented by Chemical Formula 1 above can be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Chemical Formula 1 above may be included in the light-emitting layer. In this case, the organometallic compound acts as a dopant, and the light-emitting layer may further include a host (i.e., the content of the organometallic compound represented by Chemical Formula 1 is less than the content of the host). The light-emitting layer may emit red light or green light.

[0235] For example, the organometallic compound represented by the above chemical formula 1 can emit green light having a maximum emission wavelength in the range of 500 nm to 550 nm, for example, 500 nm to 540 nm.

[0236] In this specification, the phrase “(the organic layer) comprises one or more organometallic compounds” may be interpreted as “(the organic layer) may comprise one organometallic compound belonging to the category of Formula 1 or two or more different organometallic compounds belonging to the category of Formula 1.”

[0237] For example, the organic layer may include only compound 1 as the organometallic compound. In this case, compound 1 may be present in the light-emitting layer of the organic light-emitting device. Alternatively, the organic layer may include compound 1 and compound 2 as the organometallic compound. In this case, compound 1 and compound 2 may be present in the same layer (for example, both compound 1 and compound 2 may be present in the light-emitting layer).

[0238] The first electrode is an anode that is a hole injection electrode and the second electrode is a cathode that is an electron injection electrode, or the first electrode is a cathode that is an electron injection electrode and the second electrode is an anode that is a hole injection electrode.

[0239] For example, among the above organic light-emitting devices, the first electrode is an anode and the second electrode is a cathode, and the organic layer further includes a hole transport region disposed between the first electrode and the light-emitting layer and an electron transport region disposed between the light-emitting 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 any combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0240] In this specification, "organic layer" is a term referring to a single and / or multiple layers disposed between a first electrode and a second electrode of an organic light-emitting device. The "organic layer" may include not only organic compounds but also organometallic complexes containing metals.

[0241] FIG. 1 schematically illustrates a cross-sectional view of an organic light-emitting element (10) according to one embodiment of the present invention. Hereinafter, with reference to FIG. 1, the structure and manufacturing method of an organic light-emitting element according to one embodiment of the present invention will be described as follows. The organic light-emitting element (10) has a structure in which a first electrode (11), an organic layer (15), and a second electrode (19) are stacked in sequence.

[0242] A substrate may be additionally disposed on the lower part of the first electrode (11) or on the upper part of the second electrode (19). As the substrate, a substrate used in conventional organic light-emitting diodes may be used, and a glass substrate or a transparent plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance may be used.

[0243] The first electrode (11) may be formed, for example, by providing a material for the first electrode on a substrate using a deposition method or a sputtering method. The first electrode (11) may be an anode. The material for the first electrode may include a material having a high work function to facilitate hole injection. The first electrode (11) may be a reflective electrode, a semi-transparent electrode, or a transparent electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc. may be used. Alternatively, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. may be used.

[0244] The first electrode (11) may have a single layer or a multilayer structure including two or more layers. For example, the first electrode (11) may have a three-layer structure of ITO / Ag / ITO.

[0245] An organic layer (15) is disposed above the first electrode (11).

[0246] The above organic layer (15) may include a hole transport region; an emission layer; and an electron transport region.

[0247] The above hole transport region can be placed between the first electrode (11) and the light-emitting layer.

[0248] The hole transport region above may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0249] The hole transport region may include only a hole injection layer or only a hole transport layer. Alternatively, the hole transport region may have a structure of a hole injection layer / hole transport layer or a hole injection layer / hole transport layer / electron blocking layer stacked sequentially from the first electrode (11).

[0250] If the hole transport region includes a hole injection layer, the hole injection layer (HIL) can be formed on the first electrode (11) using various methods such as vacuum deposition, spin coating, casting, LB method, etc.

[0251] When forming a hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal characteristics of the target hole injection layer, etc., but for example, a deposition temperature of about 100 to about 500°C and a vacuum degree of about 10 -8 to about 10 -3 torr, deposition rate can be selected in the range of about 0.01 to about 100 Å / sec.

[0252] When forming a hole injection layer by spin coating, the coating conditions vary depending on the compound used as the hole injection layer material, the structure and thermal properties of the desired hole injection layer, but a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature for solvent removal after coating can be selected in a temperature range of about 80°C to 200°C.

[0253] The above conditions for forming the hole transport layer and electron blocking layer refer to the conditions for forming the hole injection layer.

[0254] The above hole transport region is, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine)), Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PEDOT / PSS (Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), Pani / CSA (Polyaniline / Camphorsulfonic acid), PANI / PSS (Polyaniline) / Poly(4-styrenesulfonate):Polyaniline) / Poly(4-styrenesulfonate)), may include a compound represented by the following chemical formula 201, a compound represented by the following chemical formula 202, or any combination thereof:

[0255]

[0256]

[0257] <Chemical Formula 201>

[0258]

[0259] <Chemical Formula 202>

[0260]

[0261] In the above chemical formula 201, Ar 101 and Ar 102 are independently, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 It may be a phenylene group, pentarenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, naphthacenylene group, pisenylene group, perylenylene group, or pentacenylene group, substituted or unsubstituted with a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, or any combination thereof.

[0262] In the above chemical formula 201, xa and xb may independently be integers from 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0.

[0263] Among the above chemical formulas 201 and 202, R 101 to R 108 , R 111 to R 119 and R 121 to R 124 are independently of each other,

[0264] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 10 Alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.) or C1-C10 Alkoxy groups (e.g., methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, etc.);

[0265] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, or any combination thereof substituted, C1-C 10 alkyl group or C1-C 10 Alkoxy group; or

[0266] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 10 Alkyl group, C1-C 10 A phenyl group, naphthyl group, anthracenyl group, fluorenyl group, or pyrenyl group substituted or unsubstituted with an alkoxy group, or any combination thereof;

[0267] It could be.

[0268] In the above chemical formula 201, R 109 is, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 20 Alkyl group, C1-C 20 It may be a phenyl group, naphthyl group, anthracenyl group, or pyridinyl group substituted or unsubstituted with an alkoxy group, a phenyl group, a naphthyl group, anthracenyl group, a pyridinyl group, or any combination thereof.

[0269] According to one embodiment, the compound represented by the above chemical formula 201 may be represented by the following chemical formula 201A:

[0270] <Chemical Formula 201A>

[0271]

[0272] In the above chemical formula 201A, R 101 , R 111 , R 112 and R 109 For a detailed explanation of [this], refer to the above.

[0273] For example, the hole transport region may include at least one of the following compounds HT1 to HT20:

[0274]

[0275]

[0276]

[0277]

[0278] The thickness of the hole transport region may be about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. If the hole transport region includes a hole injection layer, a hole transport layer, or a combination thereof, the thickness of the hole injection layer may be about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the ranges described above, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

[0279] In addition to the material described above, the hole transport region may further include a charge-generating material to enhance conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region.

[0280] The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound. For example, non-limiting examples of the p-dopant include quinone derivatives such as tetracyanoquinone dimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4-TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; and cyano group-containing compounds such as the following compound HT-D1.

[0281]

[0282] The above hole transport region may further include a buffer layer.

[0283] The above buffer layer can play a role in increasing efficiency by compensating for the optical resonance distance according to the wavelength of light emitted from the light-emitting layer.

[0284] Meanwhile, if the hole transport region includes an electron blocking layer, the electron blocking layer material may include a material that can be used in the hole transport region as described above, a host material described later, or any combination thereof. For example, if the hole transport region includes an electron blocking layer, the mCP described later may be used as the electron blocking layer material.

[0285] An emissive layer (EML) can be formed on the hole transport region using methods such as vacuum deposition, spin coating, casting, and LB. When forming the emissive layer by vacuum deposition and spin coating, the deposition and coating conditions vary depending on the compound used, but generally, they can be selected from a range of conditions that are almost identical to those for forming the hole injection layer.

[0286] The light-emitting layer may include a host and a dopant, and the dopant includes an organometallic compound represented by the chemical formula 1.

[0287] The above host may include TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, or any combination thereof:

[0288]

[0289]

[0290] When the above organic light-emitting device is a full-color organic light-emitting device, the light-emitting layer may be patterned into a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer. Alternatively, various variations are possible, such as the light-emitting layer having a stacked structure of a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer to emit white light.

[0291] When the above-mentioned light-emitting layer includes a host and a dopant, the content of the dopant can typically be selected in the range of about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host.

[0292] The above dopant may be an organometallic compound represented by Chemical Formula 1 in this specification. For example, the above dopant may be a green phosphorescent dopant.

[0293] The thickness of the light-emitting layer may be about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-emitting layer satisfies the range described above, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.

[0294] Next, an electron transport region can be placed on top of the light-emitting layer.

[0295] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0296] For example, the electron transport region may have a structure of a hole blocking layer / electron transport layer / electron injection layer or an electron transport layer / electron injection layer. The electron transport layer may have a single layer or a multilayer structure including two or more different materials.

[0297] The formation conditions of the hole blocking layer, electron transport layer, and electron injection layer of the above electron transport region refer to the formation conditions of the hole injection layer.

[0298] If the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, BCP, BPhen, BAlq, or any combination thereof.

[0299]

[0300] The thickness of the hole blocking layer may be about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the range described above, excellent hole blocking characteristics can be obtained without a substantial increase in driving voltage.

[0301] The electron transport layer may include BCP, BPhen, Alq3, Balq, TAZ, NTAZ, or any combination thereof.

[0302]

[0303] Alternatively, the electron transport layer may comprise at least one of the following compounds ET1 to ET25 and any combination thereof.

[0304]

[0305]

[0306]

[0307]

[0308] The thickness of the electron transport layer may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

[0309] The electron transport layer described above may further include a metal-containing material in addition to the material described above.

[0310] The metal-containing material may include a Li complex. The Li complex may include, for example, the following compounds ET-D1 (LiQ) or ET-D2.

[0311]

[0312] Additionally, the electron transport region may include an electron injection layer (EIL) that facilitates the injection of electrons from the second electrode (19).

[0313] The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.

[0314] The thickness of the electron injection layer may be about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0315] A second electrode (19) is disposed on the upper portion of the organic layer (15). The second electrode (19) may be a cathode. For the material of the second electrode (19), a metal, alloy, electrically conductive compound, or a combination thereof having a relatively low work function may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc., which may be used as the material for forming the second electrode (19). Alternatively, various modifications are possible, such as forming a transparent second electrode (19) using ITO or IZO to obtain a front-emitting element.

[0316] The above organic light-emitting element has been described with reference to FIG. 1, but is not limited thereto.

[0317] According to another aspect, the organic light-emitting element may be included in an electronic device. Accordingly, an electronic device including the organic light-emitting element is provided. The electronic device may include, for example, a display, lighting, a sensor, etc.

[0318] According to another aspect, a diagnostic composition is provided comprising one or more organometallic compounds represented by the above chemical formula 1.

[0319] Since the organometallic compound represented by the above chemical formula 1 can provide high luminescence efficiency, the diagnostic composition containing the organometallic compound can have high diagnostic efficiency.

[0320] The above diagnostic composition can be applied in various ways to diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc.

[0321] C1-C in this specification 60 The alkyl group refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and C1-C 60 The alkylene group is the C1-C60 It refers to a divalent group having the same structure as an alkyl group.

[0322] C1-C in this specification 60 Alkyl group, C1-C 20 Alkyl groups and / or C1-C 10 Examples of alkyl groups include methyl groups, ethyl groups, n -Propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -Pentyl, tert -Pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -Isopentyl group, n - Hexyl group, isohexyl group, sec -hexyl group, tert -hexyl group, n - heptyl group, isoheptyl group, sec -Heptyl group, tert -Heptyl group, n -Octyl group, iso-octyl group, sec -Octyl group, tert -Octyl group, n -Nonilgi, Isononilgi, sec -Playing, tert -Playing, n - Decyl group, isodecyl group, sec -Desil, tert - A methyl group, ethyl group, substituted or unsubstituted with a decyl group, or any combination thereof, n -Propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -Pentyl, tert -Pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -Isopentyl group, n - Hexyl group, isohexyl group, sec -hexyl group, tert -hexyl group, n - heptyl group, isoheptyl group, sec -Heptyl group, tert -Heptyl group,n -Octyl group, iso-octyl group, sec -Octyl group, tert -Octyl group, n -Nonilgi, Isononilgi, sec -Playing, tert -Playing, n - Decyl group, isodecyl group, sec - Decyl group or tert - Decyl groups, etc. may be included. For example, the above chemical formula 9-33 can be viewed as a branched C6 alkyl group, which is a tert-butyl group substituted with two methyl groups.

[0323] C1-C in this specification 60 The alkoxy group is -OA 101 (Here, A 101 The above C1-C 60 It refers to a monovalent group having the chemical formula of an alkyl group.

[0324] C1-C in this specification 60 Alkoxy group, C1-C 20 Alkoxy group or C1-C 10 Examples of alkoxy groups may include methoxy groups, ethoxy groups, propoxy groups, butoxy groups, or pentoxy groups.

[0325] C1-C in this specification 60 Alkylthio -SA 101 (Here, A 101 The above C1-C 60 It refers to a monovalent group having the chemical formula of an alkyl group.

[0326] C2-C in this specification 60 The alkenyl group is the above C2-C 60 It has a structure comprising one or more carbon-carbon double bonds at the middle or terminal of an alkyl group, specific examples thereof including an ethenyl group, a propenyl group, a butenyl group, etc. In this specification, C2-C 60 The alkenylene group is the above C2-C 60 It refers to a divalent group having the same structure as an alkenyl group.

[0327] C2-C in this specification 60The alkynyl group is the above C2-C 60 It has a structure comprising one or more carbon-carbon triple bonds at the middle or terminal of an alkyl group, specific examples thereof including ethynyl groups, propynyl groups, etc. In this specification, C2-C 60 The alkynylene group is the above C2-C 60 It refers to a divalent group having the same structure as an alkynyl group.

[0328] C3-C in this specification 10 A cycloalkyl group refers to a monocyclic group of a monovalent saturated hydrocarbon having 3 to 10 carbon atoms, and C3-C 10 The cycloalkylene group is the C3-C above. 10 It refers to a divalent group having the same structure as a cycloalkyl group.

[0329] C3-C in this specification 10 Examples of cycloalkyl groups may include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group (norbornanyl group), bicyclo[2.2.2]octyl group, etc.

[0330] C1-C in this specification 10 A heterocycloalkyl group refers to a monovalent monocyclic group having 1 to 10 carbon atoms comprising at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and C1-C 10 The heterocycloalkylene group is the C1-C 10 It refers to a divalent group having the same structure as a heterocycloalkyl group.

[0331] C1-C in this specification 10Examples of heterocycloalkyl groups may include silolanyl, silinanyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, tetrahydrothiophenyl, etc.

[0332] C3-C in this specification 10 A cycloalkenyl group refers to a monovalent monocyclic group having 3 to 10 carbon atoms, having at least one carbon-carbon double bond within the ring, but not having aromaticity; specific examples thereof include cyclopentenyl groups, cyclohexenyl groups, cycloheptenyl groups, etc. In this specification, C3-C 10 The cycloalkenylene group is the above C3-C 10 It refers to a divalent group having the same structure as a cycloalkenyl group.

[0333] C1-C in this specification 10 The heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms, comprising at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and having at least one double bond within the ring. The C1-C 10 Specific examples of heterocycloalkenyl groups include 2,3-dihydrofuranyl groups, 2,3-dihydrothiophenyl groups, etc. In this specification, C1-C 10 The heterocycloalkenylene group is the above C1-C 10 It refers to a divalent group having the same structure as a heterocycloalkenyl group.

[0334] C6-C in this specification 60 An aryl group refers to a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms, and C6-C 60The arylene group refers to a divalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms. The above C6-C 60 Specific examples of aryl groups include phenyl groups, naphthyl groups, anthracenyl groups, phenanthrenyl groups, pyrenyl groups, chrysenyl groups, etc. The above C6-C 60 Aryl group and C6-C 60 If the arylene group contains two or more rings, the two or more rings can be fused together.

[0335] C7-C in this specification 60 The alkylaryl group is at least one C1-C 60 C6-C substituted with alkyl groups 60 It means Arilgi.

[0336] C1-C in this specification 60 A heteroaryl group refers to a monovalent group having a cyclic aromatic system having 1 to 60 carbon atoms, comprising at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and C1-C 60 A heteroarylene group refers to a divalent group having a carbocyclic aromatic system having 1 to 60 carbon atoms, comprising at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom. 60 Specific examples of heteroaryl groups include pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolinyl groups, isoquinolinyl groups, etc. The above C1-C 60 heteroaryl group and C1-C 60 If a heteroarylene group contains two or more rings, the two or more rings can be fused together.

[0337] C2-C in this specification 60 The alkylheteroaryl group is at least one C1-C 60 C1-C substituted with alkyl groups 60 It means a heteroaryl group.

[0338] C6-C in this specification60 The aryloxy group is -OA 102 (Here, A 102 is the above C6-C 60 Pointing to arylgime), and the above C6-C 60 arylthio is -SA 103 (Here, A 103 The above C6-C 60 Pointing to arylgiim), and the above C1-C 60 The alkylthio group is -SA 104 (Here, A 104 is the above C1-C 60 It refers to an alkyl group.

[0339] In this specification, a monovalent non-aromatic condensed polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are condensed together, and the entire molecule contains only carbon as a ring-forming atom and has non-aromaticity. Specific examples of the monovalent non-aromatic condensed polycyclic group include fluorenyl groups, etc. In this specification, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

[0340] In this specification, a monovalent non-aromatic condensed heteropolycyclic group refers to a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are condensed together, and in addition to carbon, a heteroatom selected from N, O, P, Si, Se, Ge, B, and S is included as a ring-forming atom, and the entire molecule has non-aromaticity. The monovalent non-aromatic condensed heteropolycyclic group includes a carbazole group, etc. In this specification, a divalent non-aromatic heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic heteropolycyclic group.

[0341] C5-C in this specification 30 A carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbons as ring-forming atoms. The above C5-C 30 A carbocyclic group can be a monocyclic group or a polycyclic group. "(at least one R 10a C5-C (substituted or unsubstituted) 30 "Carbocyclic group" is, for example, (at least one R 10a It may include adamantane group, norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.1]heptane group (norbornane group), bicyclo[2.2.2]octane group, cyclopentane group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, silol group, fluorene group, etc., which are substituted or unsubstituted.

[0342] C1-C in this specification 30A heterocyclic group refers to a saturated or unsaturated cyclic group having, in addition to 1 to 30 carbons as ring-forming atoms, at least one heteroatom selected from N, O, P, Si, Se, Ge, B, and S. The above C1-C 30 The heterocyclic group may be a monocyclic group or a polycyclic group. The above C1-C 30 A heterocyclic group can be a monocyclic group or a polycyclic group. "(at least one R 10a C1-C (substituted or unsubstituted) 30 "Heterocyclic group" is, for example, (at least one R 10a(Substituted or unsubstituted,) thiophene group, furan group, pyrrole group, silol group, borol group, phosphol group, selenophene group, germol group, benzothiophene group, benzofuran group, indole group, indene group, benzocilol group, benzoborol group, benzophospol group, benzoselenophene group, benzozermol group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzocilol group, dibenzoborol group, dibenzophospol group, dibenzoselenophene group, dibenzozermol group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzicilol group, azabenzoborol group, Azabenzophosphol group, azabenzoselenopene group, azabenzozermol group, azadibenzothiophen group, azadibenzofuran group, azacarbazole group, azafluoren group, azadibenzicilol group, azadibenzovorol group, azadibenzophosphol group, azadibenzoselenopene group, azadibenzozermol group, azadibenzothiophen 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophen 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazolin group, phenanthroline group, pyrazol group, imidazole group, triazole group, oxazole group, isooxazole group, thiazole It may include the group, isothiaazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiaazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, etc.

[0343] In this specification, "deuterated C1-C 60Alkyl group (or, deuterium C1-C 20 alkyl groups, etc.”, “Deuteriumized C3-C 10 cycloalkyl group", "deuterated C1-C 10 The "heterocycloalkyl group" and the "deuterated phenyl group" are each substituted with at least one deuterium, C1-C 60 alkyl group (or, C1-C 20 alkyl groups, etc.), C3-C 10 Cycloalkyl group, C1-C 10 It refers to heterocycloalkyl groups and phenyl groups. For example, "deuterated C1 alkyl group (i.e., deuterated methyl group)" may include -CD3, -CD2H, and -CDH2, and the "deuterated C3-C 10 Examples of "cycloalkyl groups" may refer, for instance, to the above Chemical Formula 10-501. The above "deuterated C1-C 60 Alkyl group (or, deuterium C1-C 20 alkyl groups, etc.”, “Deuterium C3-C 10 "cycloalkyl group", or "deuterated C1-C 10 "Heterocycloalkyl group" is i) a fully deuteriumated C1-C in which all hydrogens included in each group are substituted with deuterium. 60 Alkyl group (or, fully deuteriumized C1-C 20 alkyl groups, etc.), fully deuteriumated C3-C 10 Cycloalkyl groups, or fully deuterated C1-C 10 ii) a heterocycloalkyl group, or ii) a partially deuteriumated C1-C group in which not all hydrogens included in each group are substituted with deuterium. 60 Alkyl group (or, partially deuterium C1-C 20 alkyl groups, etc.), partially deuteriumated C3-C 10 Cycloalkyl groups, or partially deuterium C1-C 10 It can be a heterocycloalkyl group.

[0344] In this specification, "(C1-C 20An "alkyl 'X' group" refers to at least one C1-C 20 It refers to an 'X' group substituted with an alkyl group. For example, in this specification "(C1-C 20 Alkyl)C3-C 10 "Cycloalkyl group" refers to at least one C1-C 20 C3-C substituted with alkyl groups 10 Pointing to a cycloalkyl group, "(C1-C 20 "alkyl)phenyl group" refers to at least one C1-C 20 It refers to a phenyl group substituted with an alkyl group. An example of a (C1-alkyl)phenyl group is the toluyl group.

[0345] In this specification, "azindole group, azabenzoborol group, azabenzophospol group, azaindene group, azabenzicillol group, azabenzozermol group, azabenzothiophene group, azabenzoselenopene group, azabenzofuran group, azacarbazole group, azadibenzoborol group, azadibenzophospol group, azafluoren group, azadibenzicillol group, azadibenzozermol group, azadibenzothiophene group, azadibenzoselenopene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group" each refers to "indole group, benzoborol group, benzophospol group, indene group, benzicillol group, benzozermol group, benzothiophene group, It means a heterocyclic group having the same backbone as the “benzoselenopene group, benzofuran group, carbazole group, dibenzoborol group, dibenzophosphor group, fluorene group, dibenzosilol group, dibenzozermol group, dibenzothiophene group, dibenzoselenopene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group,” wherein at least one of the carbons forming the ring is substituted with nitrogen.

[0346] The above-mentioned substituted C5-C 30 Carbocyclic group, substituted C2-C 30 Heterocyclic group, substituted C1-C60 Alkyl groups, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 Alkoxy group, substituted C1-C 60 Alkylthio group, substituted C3-C 10 Cycloalkyl group, substituted C1-C 10 Heterocycloalkyl group, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C7-C 60 alkylaryl group, substituted C6-C 60 aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 Heteroaryl group, substituted C2-C 60 The substituents of the alkyl heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic heterocondensed polycyclic group are independent of each other,

[0347] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group or C1-C 60 Alkoxygenation;

[0348] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C10 Heterocycloalkenyl group, C6-C 60 Arylgi, C7-C 60 Alkyl aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, C2-C 60 Alkyl heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ), or substituted with any combination thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group or C1-C 60 Alkoxygenation;

[0349] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Arylgi, C7-C 60 Alkyl aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60Heteroaryl group, C2-C 60 Alkyl heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), -P(Q 28 )(Q 29 ), or substituted or unsubstituted with any combination thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Arylgi, C7-C 60 Alkyl aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, C2-C 60 Alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic heterocondensed polycyclic group;

[0350] -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ), -P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 ); or

[0351] Any combination of these;

[0352] It could be.

[0353] Q1 to Q9 in this specification, Q 11 to Q 19 , Q 21 to Q29 and Q 31 to Q 39 are independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; amido group; hydrazine group; hydrazone group; carboxylic acid group or salt thereof; sulfonic acid group or salt thereof; phosphate group or salt thereof; deuterium, C1-C 60 Alkyl group, C6-C 60 C1-C substituted or unsubstituted with an aryl group, or any combination thereof 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; C3-C 10 Cycloalkyl group; C1-C 10 Heterocycloalkyl group; C3-C 10 Cycloalkenyl group; C1-C 10 Heterocycloalkenyl group; deuterium, C1-C 60 Alkyl group, C6-C 60 C6-C6 substituted or unsubstituted with an aryl group, or any combination thereof 60 Aryl group; C6-C 60 Aryloxy group; C6-C 60 Arylthio group; C1-C 60 It is a heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic heterocondensed polycyclic group.

[0354] Hereinafter, compounds and organic light-emitting devices according to one embodiment of the present invention will be described in more detail with reference to synthesis examples and embodiments, but the present invention is not limited to the following synthesis examples and embodiments. In the following synthesis examples, the amount of 'B' used instead of 'A' in the expression "'B' was used instead of 'A'" is the same as the amount of 'A' used in terms of molar equivalents.

[0355] [Example]

[0356] Synthesis Example 1 (Compound 1)

[0357]

[0358] Synthesis of Compounds 1-3

[0359] Compound 1-4 (33.1 mmol) and iridium chloride (5.2 g, 14.7 mmol) were mixed with 120 mL of ethoxyethanol and 40 mL of distilled water, stirred under reflux for 24 hours, and then cooled to room temperature. The resulting solid was separated by filtration and thoroughly washed with water, methanol, and hexane. The obtained solid was dried in a vacuum oven to obtain compound 1-3 (85% yield).

[0360] Synthesis of Compound 1-2

[0361] Compound 1-3 (1.2 mmol) was mixed with 45 mL of methylene chloride, and then AgOTf (0.6 g, 2.3 mmol) was mixed with 15 mL of methanol and added. Afterward, the mixture was stirred at room temperature for 18 hours while blocking light with aluminum foil, and then the resulting solid was removed by Celite filtration. The solid obtained by applying reduced pressure to the filtrate (Compound 1-2) was used in the following reaction without further purification.

[0362] Synthesis of Compound 1

[0363] 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide were mixed with Compound 1-2 (2.3 mmol) and Compound 1-1 (2.8 mmol), and the mixture was refluxed and stirred for 48 hours, after which the temperature was lowered. The mixture obtained therefrom was subjected to column chromatography (eluents: MC (methylene chloride) and hexane) on the resulting solid under reduced pressure to obtain Compound 1 (45% yield). The substance was identified through Mass Spectrometry and HPLC analysis.

[0364] HRMS(MALDI) calcd for C 39 H 26 IrN3O2: m / z 760.86 Found: 761.30

[0365] Synthetic example 2 (Compound 2)

[0366]

[0367] Compound 2 (55% yield) was obtained using the same method as the synthesis method of Compound 1 of Synthesis Example 1, except that Compound 2-1 was used instead of Compound 1-1. The substance was identified through Mass and HPLC analysis.

[0368] HRMS(MALDI) calcd for C 45 H 30 IrN3O2: m / z 836.96 Found: 837.60

[0369] Synthesis Example 3 (Compound 3)

[0370]

[0371] Compound 3 (50% yield) was obtained using the same method as the synthesis method of Compound 1 of Synthesis Example 1, except that Compound 3-1 was used instead of Compound 1-1. The substance was identified through Mass and HPLC analysis.

[0372] HRMS(MALDI) calcd for C 42 H 32 IrN3O2: m / z 787.22 Found: 788.15

[0373] Synthesis Example 4 (Compound 4)

[0374]

[0375] Compound 4 (45% yield) was obtained using the same method as the synthesis method of Compound 1 of Synthesis Example 1, except that Compound 4-1 was used instead of Compound 1-1. The substance was identified through Mass and HPLC analysis.

[0376] HRMS(MALDI) calcd for C 39 H 26IrN3O2: m / z 760.86 Found: 761.35

[0377] Synthesis Example 5 (Compound 5)

[0378]

[0379] Synthesis of Compound 5-3

[0380] Compound 5-3 (50% yield) was obtained using the same method as the synthesis method of Compound 1-3 of Synthesis Example 1, except that Compound 4-1 was used instead of Compound 1-4.

[0381] Synthesis of Compound 5-2

[0382] Compound 5-2 was obtained using the same method as the synthesis method of Compound 1-2 of Synthesis Example 1, except that Compound 5-3 was used instead of Compound 1-3, and was then used in the next reaction without further purification.

[0383] Synthesis of Compound 5

[0384] Compound 5 (50% yield) was obtained using the same method as the synthesis method of Compound 1 of Synthesis Example 1, except that Compound 5-2 and Compound 1-4 were used instead of Compound 1-2 and Compound 1-1, respectively. The substance was identified through Mass and HPLC analysis.

[0385] HRMS(MALDI) calcd for C 45 H 28 IrN3O4: m / z 866.94 Found: 867.23

[0386] Synthesis Example 6 (Compound 6)

[0387]

[0388] Compound 6 (45% yield) was obtained using the same method as the synthesis method of Compound 1 of Synthesis Example 1, except that Compound 6-1 was used instead of Compound 1-1. The substance was identified through Mass and HPLC analysis.

[0389] HRMS(MALDI) calcd for C 39 H 26 IrN3OS: m / z 776.93 Found: 777.56

[0390] Synthesis Example 7 (Compound 7)

[0391]

[0392] Compound 7 (50% yield) was obtained using the same method as the synthesis method of Compound 1 of Synthesis Example 1, except that Compound 7-1 was used instead of Compound 1-1. The substance was identified through Mass and HPLC analysis.

[0393] HRMS(MALDI) calcd for C 42 H 38 IrN3O2Si: m / z 833.04 Found: 833.97

[0394] Synthesis Example 8 (Compound 8)

[0395]

[0396] Synthesis of Compound 8-3

[0397] Compound 8-3 (55% yield) was obtained using the same method as the synthesis method of Compound 1-3 of Synthesis Example 1, except that Compound 8-4 was used instead of Compound 1-4.

[0398] Synthesis of Compound 8-2

[0399] Compound 8-2 was obtained using the same method as the synthesis method of Compound 1-2 of Synthesis Example 1, except that Compound 8-3 was used instead of Compound 1-3, and was then used in the next reaction without further purification.

[0400] Synthesis of Compound 8

[0401] Compound 8 (55% yield) was obtained using the same method as the synthesis method of Compound 1 of Synthesis Example 1, except that Compound 8-2 and Compound 1-4 were used instead of Compound 1-2 and Compound 1-1, respectively. The substance was identified through Mass and HPLC analysis.

[0402] HRMS(MALDI) calcd for C 51 H 44 IrN3O4Si2: m / z 1011.33 Found: 1012.25

[0403] Synthesis Example 9 (Compound 9)

[0404]

[0405] Compound 9 (50% yield) was obtained using the same method as the synthesis method of Compound 1 of Synthesis Example 1, except that Compound 9-1 was used instead of Compound 1-1. The substance was identified through Mass and HPLC analysis.

[0406] HRMS(MALDI) calcd for C 48 H 34 IrN3O2: m / z 911.11 Found: 912.30

[0407] Example 1

[0408] A glass substrate with ITO deposited to a thickness of 1000 Å as an anode was cut into a size of 50 mm x 50 mm x 0.5 mm, ultrasonically cleaned for 5 minutes each using isopropyl alcohol and pure water, then cleaned by irradiating with ultraviolet light for 30 minutes and exposing to ozone, and installed in a vacuum deposition apparatus.

[0409] A hole injection layer with a thickness of 600 Å was formed by vacuum depositing 2-TNATA on the above anode, and a hole transport layer with a thickness of 1350 Å was formed by vacuum depositing 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter NPB) on the above hole injection layer.

[0410] Next, CBP (host) and compound 1 (dopant) were co-deposited on the hole transport layer in a weight ratio of 90:10 to form a 400 Å thick light-emitting layer.

[0411] Afterwards, a hole blocking layer with a thickness of 50 Å was formed by vacuum depositing BCP on the light-emitting layer, and then an electron transport layer with a thickness of 350 Å was formed by vacuum depositing Alq3 on the hole blocking layer, and then an electron injection layer with a thickness of 10 Å was formed by vacuum depositing LiF on the electron transport layer, and then a cathode with a thickness of 1200 Å was formed by depositing Al on the electron injection layer, thereby fabricating an organic light-emitting device.

[0412]

[0413] Examples 2 to 9 and Comparative Examples A to C

[0414] An organic light-emitting device was fabricated using the same method as in Example 1, except that the compounds listed in Table 10 were used as dopants instead of Compound 1 when forming the light-emitting layer.

[0415] Evaluation Example 1: Characteristics evaluation of organic light-emitting diodes

[0416] For each organic light-emitting diode fabricated in Examples 1 to 9 and Comparative Examples A to C, the driving voltage, the maximum value of external quantum efficiency (Max EQE), the full width at half maximum (FWHM) of the main peak of the EL spectrum, and the maximum emission wavelength were evaluated, and the results are shown in Table 10. A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation devices.

[0417] No. of the dopant compound in the light-emitting layer Driving voltage (V) Max EQE(%) Half width (nm) Maximum emission wavelength (nm) Example 1 1 6.5 20 80 505 Example 2 2 6.2 20 82 508 Example 3 3 6.4 20 78 510 Example 4 4 6.1 20 76 516 Example 5 5 6.2 19 77 514 Example 6 6 6.5 20 80 540 Example 7 7 6.4 19 79 521 Example 8 8 6.5 20 80 528 Example 9 9 6.1 20 70 516 Comparative Example A A 6.7 18 76 518 Comparative Example B B 6.6 18 76 565 Comparative Example C C 6.6 19 82 538

[0418]

[0419]

[0420]

[0421] From Table 10 above, it can be seen that the organic light-emitting devices of Examples 1 to 9 emit green light and have improved driving voltage and improved external quantum efficiency compared to the organic light-emitting devices of Comparative Examples A to C. Explanation of the symbols

[0422] 10: Organic light-emitting diode 11: First electrode 15: Organic layer 19: Second electrode

Claims

Claim 1 Organometallic compound represented by the following chemical formula 1: <Chemical Formula 1>M(L1) n1 (L2) n2 In the above Chemical Formula 1, M is Ir, Pt, or Os, L1 is a ligand represented by the following Chemical Formula 2, n1 is 1 or 2, and if n1 is 2 or more, 2 or more L1s are identical or different from each other, L2 is a group represented by the following Chemical Formula 3D, n2 is 1 or 2, and if n2 is 2 or more, 2 or more L2s are identical or different from each other, L1 and L2 are different from each other, <Chemical Formula 2> <Chemical Formula 3> X in the above chemical formula 2 11 is C, N, or C(R) bonded to X1 of Chemical Formula 3. 11 ) and, X 12 is C, N, or C(R) bonded to X1 or X2 of Chemical Formula 3. 12 ) and, X 13 C, N, or C(R) bonded to X1 or X2 of Chemical Formula 3 13 ) and, X 14 is C, N, or C(R) bonded to X2 of Chemical Formula 3. 14 ) and, among the above chemical formula 2, i) X 11 is C bonded to X1 of Chemical Formula 3, and X 12 is C bonded to X2 of Chemical Formula 3; ii) X 12 is C bonded to X1 of Chemical Formula 3, and X 13 is C bonded to X2 of Chemical Formula 3; or iii) X 13 is C bonded to X1 of Chemical Formula 3, and X 14 is C bonded to X2 in Chemical Formula 3, and X1 in Chemical Formula 3 is O, S, Se, B(R 31 ), N(R 31 ), C(R 31 )(R 32 ) or Si(R 31 )(R 32 ) and in Chemical Formula 3, X2 is O, S, Se, B(R 33 ), N(R 33 ), C(R 33 )(R 34 ) or Si(R 33 )(R 34 ) and Y1 is N, Y2 is C, and ring CY1 is C5-C 30 It is a carbocylic group, and ring CY2 is a benzene group, naphthalene group, dibenzofuran group, dibenzothiophene group, or carbazole group, and R1, R2, R 11 to R 14 and R 31 to R 34 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C1-C 60 A heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5), wherein R 31 and R 33 ...is not hydrogen, a1 is an integer from 0 to 10, and if a1 is 2 or more, 2 or more R1s are identical or different from each other, a2 is an integer from 0 to 20, and if a2 is 2 or more, 2 or more R2s are identical or different from each other, * and *' in Chemical Formula 2 are each binding sites with M in Chemical Formula 1, and * and *' in Chemical Formula 3 are each X in Chemical Formula 2 11 To X 14 It is a combined site with 2 of them, and Among the above chemical formula 3D, Y 11 is N, and Y 12 is C, and T 21 Silver consists of single bonds, double bonds, O, S, and C (Z 11 )(Z 12 ), Si(Z 11 )(Z 12 ) or N(Z 11 ) and, ring CY 11 C1-C 30 It is a heterocyclic group, and a ring CY 12 is C5-C 30 It is a carbose click group, Z1, Z2, Z 11 and Z 12 The description for each is the same as the description for R2 above, d1 and d2 are independent integers from 0 to 10, * and *' are binding sites with M in Chemical Formula 1, and the substituted C1-C 60 Alkyl groups, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 Alkoxy group, substituted C3-C 10 Cycloalkyl group, substituted C1-C 10 Heterocycloalkyl group, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C1-C 60 The substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic heterocondensed polycyclic group are independently deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group or C1-C 60 Alkoxy group; deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -Ge(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ), or substituted with any combination thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group or C1-C 60 Alkoxy group; deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -Ge(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), -P(Q 28 )(Q 29 ), or substituted or unsubstituted with any combination thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic group; -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ), -P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 ); or any combination thereof; and above Q1 to Q5, Q 11 to Q 19 , Q 21 to Q 29 and Q 31 to Q 39 are independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; amido group; hydrazine group; hydrazone group; carboxylic acid group or salt thereof; sulfonic acid group or salt thereof; phosphate group or salt thereof; deuterium, C1-C 60 Alkyl group, C6-C 60 C1-C substituted or unsubstituted with an aryl group, or any combination thereof 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; C3-C 10 Cycloalkyl group; C1-C 10 Heterocycloalkyl group; C3-C 10 Cycloalkenyl group; C1-C 10 Heterocycloalkenyl group; deuterium, C1-C 60 Alkyl group, C6-C 60 C6-C6 substituted or unsubstituted with an aryl group, or any combination thereof 60 Aryl group; C6-C 60 Aryloxy group; C6-C 60 Arylthio group; C1-C 60 It is a heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic heterocondensed polycyclic group. Claim 2 delete Claim 3 An organometallic compound according to claim 1, wherein M is Ir or Os and n1 + n2 is 3 or 4; or M is Pt and n1 + n2 is 2. Claim 4 An organometallic compound according to claim 1, wherein at least one of X1 and X2 of the above chemical formula 3 is O, S, or Se. Claim 5 In claim 1, i) X1 in the above chemical formula 3 is C(R 31 )(R 32 ) and X2 is O, S, Se, B(R 33 ), N(R 33 ), or Si(R 33 )(R 34 ) or; or ii) X1 is O, S, Se, B(R 31 ), N(R 31 ), or Si(R 31 )(R 32 ) and X2 is C(R 33 )(R 34 ) Organometallic compound. Claim 6 An organometallic compound according to claim 1, wherein the ring CY1 of the above chemical formula 3 is a benzene group. Claim 7 delete Claim 8 In paragraph 1, the above R1, R2, R 11 to R 14 and R 31 to R 34 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, -SF5, C1-C 20 alkyl group or C1-C 20 Alkoxy group; deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 20 Alkyl group, deuterated C1-C 20 Alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norvonanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C1-C 20 Alkyl)cyclopentyl group, (C1-C 20 Alkyl)cyclohexyl group, (C1-C 20 Alkyl)cycloheptyl group, (C1-C 20 Alkyl)cyclooctyl group, (C1-C 20 Alkyl)adamantanyl group, (C1-C 20 Alkyl)norbonanyl group, (C1-C 20 Alkyl)norborneyl group, (C1-C 20 Alkyl)cyclopentenyl group, (C1-C 20 Alkyl)cyclohexenyl group, (C1-C 20 Alkyl)cycloheptenyl group, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 Substituted with an alkyl phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, pyridinyl group, pyrimidinyl group, or any combination thereof, C1-C 20 alkyl group or C1-C 20 Alkoxy group; deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 20 Alkyl group, deuterated C1-C 20 Alkyl group, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norvonanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C1-C 20 Alkyl)cyclopentyl group, (C1-C 20 Alkyl)cyclohexyl group, (C1-C 20 Alkyl)cycloheptyl group, (C1-C 20 Alkyl)cyclooctyl group, (C1-C 20 Alkyl)adamantanyl group, (C1-C 20 Alkyl)norbonanyl group, (C1-C 20 Alkyl)norborneyl group, (C1-C 20 Alkyl)cyclopentenyl group, (C1-C 20 Alkyl)cyclohexenyl group, (C1-C 20 Alkyl)cycloheptenyl group, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrroleyl group, thiophenyl group, furanyl group, imidazoleyl group, pyrazolyl group, thiazoleyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indoleyl group, indazoleyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazoleyl group, phenanthrolinyl group, Benzoimidazoleyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazoleyl group, benzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, oxadiazoleyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, imidazopyrimidinyl group, imidazopyrimidinyl group, azacarbazoleyl group, azadibenzofuranyl group, azadibenzothiophenyl group, or any combination thereof substituted or unsubstituted, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norvonanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, cycloheptenyl group, Bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrroleyl group, thiophenyl group, furanyl group, imidazoleyl group, pyrazolyl group, thiazoleyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indoleyl group, indazoleyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazoleyl group, phenanthrolinyl group, Benzimidazoleyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazoleyl group, benzoxazoleyl group, isobenzoxazoleyl group, triazoleyl group, tetrazolyl group, oxadiazoleyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazoleyl group, dibenzocarbazoleyl group, imidazopyridinyl group, imidazopyridinyl group, azacarbazoleyl group, azadibenzofuranyl group or azadibenzothiophenyl group; or -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5); and, Q1 to Q5 are independently -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H or -CD2CDH2; or deuterium, C1-C 20 Substituted or unsubstituted with an alkyl group, a phenyl group, or any combination thereof, n -Propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -Pentyl, tert -Pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec - Isopentyl group, phenyl group, biphenyl group or naphthyl group; phosphorus, organometallic compound. Claim 9 An organometallic compound according to claim 1, wherein L1 is a ligand represented by the following chemical formula 2-1, 2-2, or 2-3: Among the above chemical formulas 2-1 to 2-3, X 11 is N or C(R 11 ) and, X 12 is N or C(R 12 ) and, X 13 is N or C(R 13 ) and, X 14 is N or C(R 14 ) and, X1, X2, Y1, Y2, ring CY1, ring CY2, R1, R2, R 11 to R 14 The descriptions for , a1, a2, * and *' are each the same as those described in Paragraph 1. Claim 10 In claim 9, the above L1 is a ligand represented by the above chemical formula 2-3, and X in the above chemical formula 2-3 12 is C(R 12 ) and, the above R 12 is an organometallic compound that is -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5). Claim 11 In claim 1, among the above chemical formula 2 Organometallic compound in which the group represented by is a group represented by one of the following chemical formulas CY2-1, CY2-11, CY2-14, CY2-17 and CY2-20 to CY2-25: Among the above chemical formulas CY2-1, CY2-11, CY2-14, CY2-17, and CY2-20 to CY2-25, the descriptions for Y2 and R2 are each the same as those described in Claim 1, and X 22 is N(R 22 ), O or S and, R 22 The description for each is the same as the description for R2 in claim 1, a26 is an integer from 0 to 6, a24 is an integer from 0 to 4, *" is a bonding site with an adjacent atom in Chemical Formula 2, and * is a bonding site with M in Chemical Formula 1. Claim 12 delete Claim 13 delete Claim 14 In claim 1, an organometallic compound wherein L2 is a ligand represented by the following chemical formula 3-1: In the above chemical formula 3-1, Y 11 , Y 12 , loop CY 12 , Z2, Z 11 , Z 12 The descriptions for and d2 are each the same as those described in Paragraph 1, and Z 13 and Z 14 The explanation regarding Z in Paragraph 1 11 The description is the same as for, and * and *' are the binding sites with M in Chemical Formula 1, respectively. Claim 15 In claim 14, among the above chemical formula 3-1 The group represented by is a group represented by one of the following chemical formulas 3-1-1 to 3-1-16, and among the chemical formula 3-1 Organometallic compound in which the group represented by is a group represented by one of the following chemical formulas 3-1(1) to 3-1(16): Among the above chemical formulas 3-1-1 to 3-1-16 and 3-1(1) to 3-1(16), Z 11 To Z 14 The descriptions for are the same as those set forth in Paragraph 14, and Z 21 To Z 24 The explanation for each is Z in Paragraph 14. 11 Same as the explanation for, but Z 11 To Z 14 and Z 21 To Z 24 is not hydrogen, and * and *' are bonding sites with M in Chemical Formula 1, respectively, and *" is a bonding site with an adjacent atom. Claim 16 In claim 1, an organometallic compound which is one of the following compounds 1 to 9: Claim 17 An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer comprises one or more organometallic compounds according to any one of claims 1, 3 to 6, 8 to 11 and 14 to 16. Claim 18 An organic light-emitting device according to claim 17, wherein the first electrode is an anode and the second electrode is a cathode, and the organic layer further comprises a hole transport region disposed between the first electrode and the light-emitting layer and an electron transport region disposed between the light-emitting layer and the second electrode, wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. Claim 19 In claim 17, an organic light-emitting device in which the organometallic compound is included in the light-emitting layer. Claim 20 An electronic device including the organic light-emitting element of claim 17.

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