Organometallic compounds and organic light-emitting devices containing them, and electronic devices containing organic light-emitting devices

Abstract

To provide a novel organometallic compound, an organic light-emitting device adopting the same, and an electronic device containing the organic light-emitting device.SOLUTION: The organometallic compound is represented by a chemical formula 1 and has a C2 symmetric structure, and a sum of Δ(Ir-N) and Δ(Ir-C) is 0.002 Å or smaller. Ir(L1)2(L2) chemical formula 1. Specifically, for example, compounds 17, 18 and 19 are shown.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to organometallic compounds and organic light-emitting devices containing the same, and more particularly to organometallic compounds and organic light-emitting devices containing the same, and electronic devices containing organic light-emitting devices having excellent outcoupling efficiency, short decay time, and improved horizontal orientation ratio. [Background technology]

[0002] Organic light-emitting devices are self-emitting elements that excel in characteristics such as viewing angle, response time, brightness, driving voltage, and response speed, and can be made multi-colored. For example, an organic light-emitting element includes an anode, a cathode, and an organic layer containing a light-emitting layer, which is positioned between the anode and the cathode. A hole transport region is provided between the anode and the light-emitting layer, and an electron transport region is 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. Holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated as excitons change from an excited state to a ground state.

[0003] For organometallic compounds used in organic layers, including the light-emitting layer of organic light-emitting devices, the development of new organometallic compounds is a challenge, with the goal of continuously improving their quality and performance. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2016-69379 [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] The present invention has been made in view of the problems in the above-described conventional organometallic compounds, and an object of the present invention is to provide a novel organometallic compound, an organic light-emitting device employing the same, and an electronic device including the organic light-emitting device.

Means for Solving the Problems

[0006] The organometallic compound according to the present invention made to achieve the above object has a C2 symmetric structure, is represented by Chemical Formula 1 shown below, and is characterized in that the sum of Δ(Ir-N) and Δ(Ir-C) is 0.002 Å or less. (Chemical Formula 1) Ir(L1)2(L2) ··· Chemical Formula 1 (In the above Chemical Formula 1, L1 is a ligand represented by the following Chemical Formula 2, L2 is a ligand represented by the following Chemical Formula 3, one of the two L1s is a first L1 ligand, and the other is a second L1 ligand, and the first L1 ligand and the second L1 ligand are identical to each other,

Chemical Formula

Chemical Formula

[0007] To achieve the above objective, the present invention provides an organic light-emitting element comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, the organic layer including a light-emitting layer, wherein the organic layer contains one or more organometallic compounds of the present invention.

[0008] In the aforementioned organic layer, the organometallic compound contained in the light-emitting layer can act as a dopant.

[0009] An electronic device made according to the present invention to achieve the above objective is characterized by including an organic light-emitting element of the present invention. [Effects of the Invention]

[0010] According to the organometallic compound, organic light-emitting element containing the same, and electronic device including the organic light-emitting element according to the present invention, the organometallic compound has excellent outcoupling efficiency, short decay time, and improved horizontal orientation ratio, and the organic light-emitting element employing the organometallic compound, and the electronic device including the organic light-emitting element, have the effect of having high luminous efficiency. [Brief explanation of the drawing]

[0011] [Figure 1] This is a simplified perspective view showing an organometallic compound represented by chemical formula 1 laminated on a predetermined film A surface according to an embodiment of the present invention. [Figure 2] Figure 2 is a simplified diagram showing the relationship between the C2 symmetry axis of an organometallic compound represented by chemical formula 1, the transition dipole moment (TDM), the horizontal orientation ratio of the transition dipole moment (TDM) (TDMH), and the vertical orientation ratio of the transition dipole moment (TDM) (TDMV) with respect to a given film A surface. [Figure 3] This is a cross-sectional view showing a schematic configuration of an organic light-emitting element according to one embodiment of the present invention. [Figure 4] This diagram illustrates the groups in compound 1 that are linked to Ir via N and those that are linked to Ir via C. [Modes for carrying out the invention]

[0012] Next, specific examples of embodiments for carrying out the organometallic compound, the organic light-emitting element containing the same, and the electronic device containing the organic light-emitting element according to the present invention will be described with reference to the drawings.

[0013] The organometallic compound of the present invention is represented by the chemical formula 1 shown below. (chemical 1) Ir(L1)2(L2)...Chemical formula 1

[0014] The organometallic compound represented by chemical formula 1 contains one iridium (Ir) atom, and in chemical formula 1, L1 is the ligand represented by chemical formula 2 shown below, and L2 is the ligand represented by chemical formula 3 shown below. [ka] [ka]

[0015] In chemical formula 2, Y1 is N and Y2 is C. For a detailed explanation of chemical formulas 2 and 3, please refer to the relevant section of this specification. One of the two L1 ligands in chemical formula 1 is a first L1 ligand, and the other is a second L1 ligand. The first L1 ligand and the second L1 ligand may be identical to each other. In chemical formula 1, the two L1 ligands (i.e., the first L1 ligand and the second L1 ligand) are identical to each other, and L2 is the ligand represented by chemical formula 3. Therefore, the organometallic compound represented by chemical formula 1 may have a C2 symmetry structure with a C2 symmetry axis.

[0016] The sum of Δ(Ir-N) and Δ(Ir-C) of the organometallic compound represented by chemical formula 1 may be less than or equal to 0.002 Å, 0 Å to 0.002 Å, 0 Å to 0.001 Å, 0 Å to 0.0009 Å, 0 Å to 0.0008 Å, or 0 Å to 0.00072 Å. Here, Δ(Ir-N) is the absolute difference between the distance between Ir and the first L1 ligand Y1 (e.g., the binding distance) and the distance between Ir and the second L1 ligand Y1 in chemical formulas 1 and 2, and the absolute difference between D1(Ir-N) and D2(Ir-N) in chemical formula 1a. Δ(Ir-C) is the absolute difference between the distance between Ir and the first L1 ligand Y2 and the distance between Ir and the second L1 ligand Y2 in chemical formulas 1 and 2, and the absolute difference between D1(Ir-C) and D2(Ir-C) in chemical formula 1a shown below. [ka]

[0017] When the sum of Δ(Ir-N) and Δ(Ir-C) of the organometallic compound represented by chemical formula 1 satisfies the aforementioned range, the S0-level vibrational state of the organometallic compound will have symmetrical properties, and the T1-S0 transition in the excited state of the organometallic compound represented by chemical formula 1 can be reduced. As a result, the full width at half maximum (FWHM) and / or full width at quarter maximum (FWQM) of the PL (photoluminescence) and / or EL (electroluminescence) spectra of the organometallic compound are reduced, and electronic devices employing the organometallic compound represented by chemical formula 1, such as organic light-emitting devices, can have excellent color purity and high luminous efficiency.

[0018] According to other embodiments, L of an organometallic compound represented by chemical formula 1 N / L C This could be 1.45-2.88, 1.45-2.50, 1.46-2.30, 1.47-2.20, 1.48-2.20, or 1.491-2.128. Here, L N This is the chemical formula 2 This is the maximum distance between a non-hydrogen atom in the group represented by TIFF0007843595000006.tif45145 and Ir in chemical formula 1. L C This is the chemical formula 2 This is the maximum distance between a non-hydrogen atom in the group represented by TIFF0007843595000007.tif38145 and Ir in chemical formula 1 (see Figure 1).

[0019] As mentioned above, L N , L C Δ(Ir-N) and Δ(Ir-C) can also be measured by performing DFT (density functional theory) calculations on organometallic compounds of chemical formula 1. For example, DFT calculations can be performed using Gaussian. According to one embodiment, during DFT calculations, the molecular structure optimization of the organometallic compound of chemical formula 1 can be performed using the B3LYP / LanL2DZ function for iridium and the B3LYP / 6-31G(G,P) function for ligands (L1 and L2).

[0020] When an organometallic compound represented by chemical formula 1 is layered on top of film A (Layer A), 1) the two ligands L1 represented by chemical formula 2 are aligned along the surface (xy plane) of film A, 2) A single ligand L2 represented by chemical formula 3 can be aligned in a direction opposite to the surface of membrane A (i.e., towards the vacuum side in the z-axis direction). Here, the C2 symmetry axis of chemical formula 1 and the binding direction between Ir and ligand L2 are parallel to each other, and the transition dipole moment (TDM) of the organometallic compound represented by chemical formula 1 is perpendicular to the C2 symmetry axis (see Figure 2).

[0021] L of organometallic compounds represented by chemical formula 1 N / L C As the aforementioned conditions are satisfied, the angle (θ) between the C2 axis of symmetry in chemical formula 1 and the surface of film A becomes smaller. The transition dipole moment (TDM) of the organometallic compound represented by chemical formula 1 with respect to the surface of film A is: i) The horizontal orientation ratio of the transition dipole moment (TDM), i.e., TDM H and, ii) The vertical orientation ratio of the transition dipole moment (TDM), i.e., TDM V This can be shown by the sum of (see Figure 2), The smaller the angle (θ) between the C2 axis of symmetry in chemical formula 1 and the surface of film A, the more TDM (Thermal Deposition Modeling) H As this increases, the transition dipole moment (TDM) of the organometallic compound becomes substantially horizontal with respect to the surface of film A. For example, the angle between the transition dipole moment (TDM) of an organometallic compound and the surface of film A can be between 0° and 10°.

[0022] Thus, when the transition dipole moment (TDM) of the organometallic compound represented by chemical formula 1 is substantially horizontal to the surface of film A, an electric field is emitted in a direction substantially horizontal to the surface of film A when an electronic device containing the organometallic compound, such as an organic light-emitting device, is driven, and optical loss due to the waveguide mode and / or surface plasmon polariton mode can be reduced. Therefore, as mentioned above, L N / L C Electronic devices employing organometallic compounds represented by chemical formula 1 that satisfy the specified range, such as organic light-emitting devices, can have high out-coupling efficiency and can embody electronic devices (e.g., organic light-emitting devices) with high luminous efficiency.

[0023] On the other hand, the maximum external quantum efficiency of an organic light-emitting device is calculated using Equation 1 shown below. (Math 1) η maxEQE =γΦη S / T η out ...Formula 1 In formula 1, η maxEQE This is the maximum external quantum efficiency, γ represents charge balance, Φ is the quantum efficiency, η S / T This is the single / triplet fraction, η out This is the outcoupling efficiency.

[0024] On the other hand, the external quantum efficiency at target luminance of an organic light-emitting element is calculated using Equation 2 shown below. (Math 2) η EQE =η maxEQE (1-r) ···Formula 2 In equation 2, η EQE This is the external quantum efficiency at the target brightness, r is the roll-off ratio.

[0025] In other words, from equations 1 and 2, in order to improve the luminescence efficiency of an organic light-emitting device, the maximum external quantum efficiency must be increased and the roll-off ratio must be decreased. However, in order to increase the maximum external quantum efficiency, the outcoupling efficiency must be increased. Organometallic compounds are L within the range described above. N / L C When the molecular structure satisfies the above conditions, it can provide high outcoupling efficiency, and organic light-emitting devices employing organometallic compounds can have improved maximum external quantum efficiency, thereby realizing organic light-emitting devices with high luminescence efficiency.

[0026] In chemical formula 2, the ring CY1 can be a polycyclic group in which three or more six-membered rings are fused together. For example, the six-membered ring may be a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, or a pyridazine group. According to one embodiment, in chemical formula 2, the ring CY1 may be a polycyclic group in which three or four six-membered rings are fused together. In chemical formula 2, the ring CY2 is C5-C 30 Carbon ring group or C1-C 30 It can be a heterocyclic group.

[0027] For example, in chemical formula 2, the ring CY2 is i) ring 1, ii) second ring; iii) A condensed ring formed by the condensation of two or more first rings, iv) A fused ring formed by the fusion of two or more second rings, or v) A condensed ring formed by the fusion of one or more first rings and one or more second rings, The first ring is a cyclopentane group, cyclopentadiene group, furan group, thiophene group, pyrrole group, silole group, germol group, borol group, selenofen group, phosphole group, oxazole group, oxadiazole group, oxatriazole group, thiazole group, thiadiazole group, thiatriazole group, pyrazole group, imidazole group, triazole group, tetrazole group, azasilol group, azagermol group, azabolol group, azaselenophen group, or azaphosphorol group. The second ring may be an adamantane group, a norbornane group (bicyclo[2.2.1]heptane 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.

[0028] According to one embodiment, in chemical formula 2, the ring CY2 is a 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, thiophene group, furan group, pyrrole group, cyclopentadiene group, silole group, borol group, phosphole group, selenofen group, germole group, benzothiophene group, benzofuran group, indole group, indene group, benzosilole group, benzoborol group, benzophosphole Azabenzothiophene group, benzogelmole group, dibenzothiophene group, dibenzofuran group, carbazole group, fluorene group, dibenzosilol group, dibenzobolol group, dibenzophosphole group, dibenzoselenophene group, dibenzogelmole group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilol group, azabenzobolol group, azabenzophosphole group, Zabenzoselenophen group, azabenzogermol group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzosilol group, azadibenzobolol group, azadibenzophosphole group, azadibenzoselenophen group, azadibenzogermol 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, quino The group may be a xaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, adamantane group, norbornane group, or norbornene group.

[0029] According to other embodiments, in chemical formula 2, the ring CY2 may be a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a silole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzosilole group.

[0030] In chemical formula 2, T1 is a para Hammett substituent constant (σ) greater than "0" and less than "0.5" (e.g., 0.01 to 0.4 or 0.01 to 0.3). p It may be a base having a value of ). Parahammet substituent constants (σ) greater than "0" and less than "0.5" p Specific examples of groups with the ) value can be found, for example, in "Hansch et al., A Survey of Hammett Subjunction Constants and Resonance and Field Parameters, Chem. Rev. 1991, 91, 165-195".

[0031] According to one embodiment, in chemical formula 2, T1 is a fluoro group (-F) or a cyano group, or Deuterium, fluoro group, cyano group, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 C1-C fluoride substituted or unsubstituted with heterocycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof. 20 Alkyl, fluoride C3-C 10 Cycloalkyl groups, C1-C fluoride 10 Heterocycloalkyl group, fluorinated phenyl group, fluorinated biphenyl group, cyano group-containing C1-C 20 C3-C containing alkyl and cyano groups 10 Cycloalkyl groups, cyano group-containing C1-C 10It may be a heterocycloalkyl group, a cyano group-containing phenyl group, or a cyano group-containing biphenyl group.

[0032] In chemical formula 2, b1 represents the number of T1 atoms and is an integer between 1 and 10. In other words, the ring CY1 in chemical formula 2 is always substituted with at least one T1. If b1 is 2 or greater, the 2 or greater T1s may be the same or different from each other. For example, b1 could be 1, 2, or 3. As mentioned above, because the ring CY1 in chemical formula 2 is always substituted with at least one T1, charge transfer at ligand L1 represented by chemical formula 2 occurs rapidly, and the organometallic compound represented by chemical formula 1 can have a relatively short decay time.

[0033] Increasing the brightness of an organic light-emitting element increases the density of excitons and polarons in the light-emitting layer. This leads to energy transfer between excitons and / or between excitons and polarons, while simultaneously causing quenching, which in turn can result in a roll-off phenomenon. Here, polaron refers to an electrically charged particle. To reduce the exciton quenching phenomenon, it is necessary to either lower the exciton density in the light-emitting layer or shorten the time that excitons exist as excitons, thereby shortening the diffusion distance of the excitons in the light-emitting layer. Here, the time spent as an exciton refers to the time the organometallic compound remains in the triplet state, i.e., the decay time. By having an organometallic compound with a short decay time, the roll-off ratio of the organic light-emitting device employing the organometallic compound is reduced, and as a result, an organic light-emitting device with high luminescence efficiency can be realized. The decay time can also be evaluated from the TRPL (time-resolved photoluminescence) spectrum of a film containing an organometallic compound represented by chemical formula 1.

[0034] In chemical formulas 2 and 3, R1, R2, and R 31 ~R 33 These are, independently of each other, 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 its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl group, substituted or unsubstituted C2-C 60 Alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy group, 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 group, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 It may be 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). For explanations regarding Q1 to Q9, please refer to the respective sections provided in this specification.

[0035] For example, neither R1 nor R2 are hydrogen. For example, in chemical formulas 2 and 3, R1, R2, and R 31 ~R33 They are independent of each other, 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 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, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl alkyl groups, C1-C fluoride 20 Alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group (bicyclo[2.2.1]heptyl 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) norbornanyl 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 20Alkyl)bicyclo[2.2.2]octyl group, siloranyl group, phenyl group, (C1-C 20 C1-C substituted with alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, pyridinyl group, pyrimidinyl group, or any combination thereof. 20 Alkyl 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, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl alkyl groups, C1-C fluoride 20 Alkyl alkyl group, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norborneyl 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) norbornanyl 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 20Alkyl)bicyclo[2.2.2]octyl group, siloranyl 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, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyridinyl group, pyrimidinyl group, pyridadinyl group, isoindolyl group, indolyl group, indazolyl group, prinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolyl group, synnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl Group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, or any combination thereof, substituted or unsubstituted, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norborneyl 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, siloranyl group, phenyl group, (C1-C 20Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, fluorenyl group, phenantrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyridinyl group, pyrimidinyl group, pyridadinyl group, isoindolyl group, indolyl group, indazolyl group, prinyl group, quinolinyl group, isoquinolinyl group, benzox Norinyl group, quinoxalinyl group, quinazolinyl group, synnorinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, or azadibenzothiophenyl group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9) or -P(Q8)(Q9), Questions Q1 through Q9 are independent of each other. -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2, or Deuterium, C1-C 20 The group may be an n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, phenyl group, biphenyl group, or naphthyl group, substituted or unsubstituted with an alkyl group, phenyl group, or any combination thereof.

[0036] According to one embodiment, in chemical formulas 2 and 3, R1, R2, and R 31 ~R 33 These are, independently of each other, hydrogen, deuterium, -F, cyano group, and substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 It may be a heterocycloalkyl group, a phenyl group, a biphenyl group, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5). According to other embodiments, in chemical formulas 2 and 3, R1, R2, and R 31 ~R 33 They are independent of each other, Hydrogen, deuterium, -F, or cyano group, Deuterium, -F, cyano group, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 C1-C14 is a C1-C14 molecule that is substituted or unsubstituted with a heterocycloalkyl group, a phenyl group, a biphenyl group, or any combination thereof. 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, phenyl groups, or biphenyl groups, It may be -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5).

[0037] Furthermore, according to other embodiments, chemical formula 2 may satisfy either condition 1-1 or condition 1-2 shown below. <Condition 1-1> R2 does not contain a fluoro group (-F) or a cyano group. <Condition 1-2> R2 is hydrogen or deuterium. Deuterium, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10C1-C14 is a C1-C14 molecule that is substituted or unsubstituted with a heterocycloalkyl group, a phenyl group, a biphenyl group, or any combination thereof. 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, phenyl groups, or biphenyl groups, It is -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5).

[0038] Furthermore, according to other embodiments, chemical formula 2 may satisfy the following conditions 2-1, 2-2, or 3. <Condition 2-1> a) At least one of the two R2 groups contains a fluoro group (-F), a cyano group, or any combination thereof. <Condition 2-2> Of the two R2s, at least one is Fluorine group (-F) or cyano group, or Deuterium, fluoro group, cyano group, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 C1-C fluoride substituted or unsubstituted with heterocycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof. 20 Alkyl, fluoride C3-C 10 Cycloalkyl groups, C1-C fluoride 10 Heterocycloalkyl group, fluorinated phenyl group, fluorinated biphenyl group, cyano group-containing C1-C 20 C3-C containing alkyl and cyano groups 10 Cycloalkyl groups, cyano group-containing C1-C 10 These are heterocycloalkyl groups, cyano-containing phenyl groups, or cyano-containing biphenyl groups. <Condition 2-3> R2 is hydrogen, deuterium, -F, or a cyano group. Deuterium, -F, cyano group, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10C1-C14 is a C1-C14 molecule that is substituted or unsubstituted with a heterocycloalkyl group, a phenyl group, a biphenyl group, or any combination thereof. 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, phenyl groups, or biphenyl groups, -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), at least one of the two R2s is Fluorine group (-F) or cyano group, or Deuterium, fluoro group, cyano group, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 C1-C fluoride substituted or unsubstituted with heterocycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof. 20 Alkyl, fluoride C3-C 10 Cycloalkyl groups, C1-C fluoride 10 Heterocycloalkyl group, fluorinated phenyl group, fluorinated biphenyl group, cyano group-containing C1-C 20 C3-C containing alkyl and cyano groups 10 Cycloalkyl groups, cyano group-containing C1-C 10 These are heterocycloalkyl groups, cyano-containing phenyl groups, or cyano-containing biphenyl groups.

[0039] In further embodiments, in chemical formula 2, the ring CY2 is not a naphthalene group (for example, in chemical formula 2, the ring CY2 is a benzene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, or a fluorene group), and chemical formula 2 may satisfy either condition 1-1 or condition 1-2. In further embodiments, in chemical formula 2, the ring CY2 is a naphthalene group, and chemical formula 2 may satisfy either condition 1-1 or condition 1-2. In further embodiments, in chemical formula 2, the ring CY2 is a naphthalene group, and chemical formula 2 can satisfy <Condition 2-1>, <Condition 2-2>, or <Condition 2-3>.

[0040] In further embodiments, in chemical formulas 2 and 3, R1, R2, and R 31 ~R 33 They are independent of each other, Hydrogen or deuterium, Deuterium, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 C1-C14 is a C1-C14 molecule that is substituted or unsubstituted with a heterocycloalkyl group, a phenyl group, a biphenyl group, or any combination thereof. 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, phenyl groups, or biphenyl groups, It may be -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5).

[0041] For example, in chemical formulas 2 and 3, R1, R2, and R 31 ~R 33 These are, independently of each other, hydrogen, deuterium, a cyano group, -F, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, and a group represented by one of the chemical formulas 9-1 to 9-39 shown below. A group in which at least one hydrogen atom is substituted with deuterium in one of the chemical formulas 9-1 to 9-39 shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 9-1 to 9-39 shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 9-1 to 9-39 shown below, A group represented by one of the chemical formulas 9-201 to 9-233 shown below, A group in which at least one hydrogen atom is substituted with deuterium in one of the chemical formulas 9-201 to 9-233 shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 9-201 to 9-233 shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 9-201 to 9-233 shown below, A group represented by one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group in which at least one hydrogen atom is substituted with deuterium in one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group represented by one of the chemical formulas 10-201 to 10-343 shown below, A group in which at least one hydrogen atom is substituted with deuterium in one of the chemical formulas 10-201 to 10-343 shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 10-201 to 10-343 shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 10-201 to 10-343 shown below, -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5) (however, for explanations of Q3 to Q5, refer to the respective sections of this specification).

[0042] As yet another example, T1 in chemical formula 2 is -F, -CF3, -CF2H, -CFH2, cyano group, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 9-1 to 9-39 shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 9-1 to 9-39 shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 9-201 to 9-233 shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 9-201 to 9-233 shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 10-201 to 10-343 shown below, Alternatively, it may be a group in which at least one hydrogen atom from one of the chemical formulas 10-201 to 10-343 shown below is substituted with a cyano group.

[0043] As yet another example, R2 in chemical formula 2 can be hydrogen, deuterium, -CH3, -CD3, -CD2H, -CDH2, A group represented by one of the chemical formulas 9-1 to 9-39 shown below, A group in which at least one hydrogen atom is substituted with deuterium in one of the chemical formulas 9-1 to 9-39 shown below, A group represented by one of the chemical formulas 9-201 to 9-233 shown below, A group in which at least one hydrogen atom is substituted with deuterium in one of the chemical formulas 9-201 to 9-233 shown below, A group represented by one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group in which at least one hydrogen atom is substituted with deuterium in one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group represented by one of the chemical formulas 10-201 to 10-343 shown below, A group in which at least one hydrogen atom is substituted with deuterium in one of the chemical formulas 10-201 to 10-343 shown below, -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5) (however, for explanations of Q3 to Q5, refer to the respective sections of this specification).

[0044] As yet another example, in chemical formula 2, R2 is hydrogen, deuterium, cyano group, -F, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, A group represented by one of the chemical formulas 9-1 to 9-39 shown below, A group in which at least one hydrogen atom is substituted with deuterium in one of the chemical formulas 9-1 to 9-39 shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 9-1 to 9-39 shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 9-1 to 9-39 shown below, A group represented by one of the chemical formulas 9-201 to 9-233 shown below, A group in which at least one hydrogen atom is substituted with deuterium in one of the chemical formulas 9-201 to 9-233 shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 9-201 to 9-233 shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 9-201 to 9-233 shown below, A group represented by one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group in which at least one hydrogen atom is substituted with deuterium in one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group represented by one of the chemical formulas 10-201 to 10-343 shown below, A group in which at least one hydrogen atom is substituted with deuterium in one of the chemical formulas 10-201 to 10-343 shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 10-201 to 10-343 shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 10-201 to 10-343 shown below, -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), but at least one of the two R2 groups is -F, -CF3, -CF2H, -CFH2, cyano group, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 9-1 to 9-39 shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 9-1 to 9-39 shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 9-201 to 9-233 shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 9-201 to 9-233 shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group in which at least one hydrogen atom is substituted with a cyano group from one of the chemical formulas 10⁻¹ to 10⁻¹²⁶ shown below, A group in which at least one hydrogen atom is substituted with -F in one of the chemical formulas 10-201 to 10-343 shown below, Alternatively, it may be a group in which at least one hydrogen atom from one of the chemical formulas 10-201 to 10-343 shown below is substituted with a cyano group.

[0045] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0046] In chemical formulas 9-1 to 9-39, 9-201 to 9-233, 10-1 to 10-126, and 10-201 to 10-343, * indicates a bonding site with an adjacent atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group.

[0047] "Groups in which at least one hydrogen atom is substituted with deuterium in chemical formulas 9-1 to 9-39," and "groups in which at least one hydrogen atom is substituted with deuterium in chemical formulas 9-201 to 9-233," may be groups represented, for example, by chemical formulas 9-501 to 9-514 and 9-601 to 9-635 shown below. [ka] [ka] [ka]

[0048] "Groups in which at least one hydrogen atom is substituted with -F in chemical formulas 9-1 to 9-39," and "groups in which at least one hydrogen atom is substituted with -F in chemical formulas 9-201 to 9-233," may be groups represented by chemical formulas 9-701 to 9-710 shown below, for example. [ka]

[0049] "Groups in which at least one hydrogen atom is substituted with deuterium in chemical formulas 10-1 to 10-126," and "groups in which at least one hydrogen atom is substituted with deuterium in chemical formulas 10-201 to 10-343," may be groups represented by chemical formulas 10-501 to 10-553, as shown below. [ka] [ka] [ka]

[0050] "Groups in which at least one hydrogen atom is substituted with -F in chemical formulas 10-1 to 10-126," and "groups in which at least one hydrogen atom is substituted with -F in chemical formulas 10-201 to 10-343," may be groups represented by chemical formulas 10-601 to 10-615, as shown below. [ka]

[0051] In chemical formula 2, a1 and a2 represent the number of R1 and R2 atoms, respectively, and can be integers between 0 and 10, independently of each other. If a1 is 2 or greater, then 2 or greater R1s are either identical or different from each other. If a2 is 2 or greater, then 2 or greater R2s may be either identical or different from each other. For example, in chemical formula 2, a1 is an integer between 0 and 3. As another example, in chemical formula 2, a² is an integer between 0 and 6. According to one embodiment, in chemical formula 2, a2 ​​is either 1 or 2. According to other embodiments, in chemical formula 2, a2 ​​is 1 or 2, and R2 is not hydrogen.

[0052] In chemical formulas 2 and 3, * and *' are the bonding sites with Ir in chemical formula 1, respectively. In further embodiments, the organometallic compound represented by chemical formula 1 may contain at least one deuterium atom. In further embodiments, at least one of the R1 atoms in chemical formula 1 may contain at least one deuterium atom. In further embodiments, at least one of the two R2 atoms in chemical formula 1 may contain deuterium. In another embodiment, at least one of the two R2s in chemical formula 1 is C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 Deuterated C1-C1, substituted or unsubstituted with heterocycloalkyl groups or any combination thereof. 20 Alkyl, deuterated C3-C 10 Cycloalkyl groups, or deuterated C1-C 10 It may be a heterocycloalkyl group.

[0053] In chemical formulas 2 and 3, 1) Two or more of the R1 atoms are selectively bound to each other, and at least one R 1a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 1a Substitute or non-substitute C1-C 30 It can form a heterocyclic group, 2) In two R2s, two or more are selectively bound to each other, and at least one R 1a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 1a Substitute or non-substitute C1-C 30It can form a heterocyclic group, 3) In R1 and R2, two or more are selectively coupled to each other, and at least one R 1a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 1a Substitute or non-substitute C1-C 30 It can form a heterocyclic group, 4) R 31 ~R 33 In this case, 2 or more are selectively coupled to each other, and at least one R 1a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 1a Substitute or non-substitute C1-C 30 It can form heterocyclic groups. R 1a For further explanation, see the explanation for R1 in this specification.

[0054] According to one embodiment, in chemical formula 2, The group represented by TIFF0007843595000034.tif36128 may be a group represented by one of the chemical formulas 2-1 to 2-21 shown below. [ka] [ka] [ka] [ka]

[0055] Chemical formulas 2-1 to 2-21, Y1 is N, X1~X 10 Although each is independently C or N, at least one of X1 to X8 in chemical formulas 2-1 to 2-9 and chemical formula 2-21 is C, and X1 to X in chemical formulas 2-10 to 2-20 10At least one of them is C, * represents the bonding site with Ir in chemical formula 1. * indicates a bonding site with an adjacent atom. For example, X1~X 10 It could be C.

[0056] According to other embodiments, in chemical formula 2, The group represented by TIFF0007843595000039.tif45145 may be a group represented by one of the chemical formulas 2(1) to 2(75) shown below. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0057] Chemical formulas 2(1) to 2(75) Y1 is N, X 11 C(R 11 ) or N, X 12 C(R 12 ) or N, X 13 C(R 13 ) or N, X 14C(R 14 ) or N, X 15 C(R 15 ) or N, X 16 C(R 16 ) or N, X 17 C(R 17 ) or N, X 18 C(R 18 ) or N, X 19 C(R 19 ) or N, X 19a C(R 19a ) or N, R 11 ~R 19 , and R 19a For explanations regarding each of these, please refer to the explanation for R1 in this specification. T 11 and T 12 For further explanations, please refer to the explanation for T1 in this specification. * represents the bonding site with Ir in chemical formula 1. * indicates a bonding site with an adjacent atom.

[0058] Furthermore, according to another embodiment, in chemical formula 2, The group represented by TIFF0007843595000049.tif38145 may be a group represented by one of the chemical formulas CY2-1 to CY2-10 shown below. [ka] [ka]

[0059] Chemical formulas CY2-1 to CY2-10, Y2 is C, X 21 O, S, N(R7), C(R 27 )(R 28 ), or Si(R 27 )(R 28 ) and R 21 ~R28 For further explanations, please refer to the explanation of R2 in this specification. *' represents the bonding site with Ir in chemical formula 1. * represents a bonding site with an adjacent atom in chemical formula 1. For example, in chemical formula 2, The group represented by TIFF0007843595000052.tif38145 may be a group represented by the chemical formula CY2-1 or CY2-8.

[0060] According to other embodiments, in chemical formula 2, The group represented by TIFF0007843595000053.tif38145 may be one of the groups represented by the following chemical formulas: CY2-1(1) to CY2-1(3), and CY2-8(1) to CY2-8(6). [ka]

[0061] for example, i) In chemical formula CY2-1 and chemical formulas CY2-1(1) to CY2-1(3), R 21 and R 23 , and ii) Chemical formulas CY2-8(1) to CY2-8(6), R 23 ~R 28 These are, independently of each other, deuterium, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 C1-C14 is a C1-C14 molecule that is substituted or unsubstituted with a heterocycloalkyl group, a phenyl group, a biphenyl group, or any combination thereof. 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 It is also a heterocycloalkyl group, a phenyl group, or a biphenyl group.

[0062] As another example, i) In chemical formula CY2-1 and chemical formulas CY2-1(1) to CY2-1(3), R 21 and R 23, and ii) Chemical formulas CY2-8(1) to CY2-8(6), R 23 ~R 28 These are, independently of each other, deuterium, C1-C 20 C1-C atoms substituted or unsubstituted with alkyl groups or any combination thereof. 20 It can be an alkyl group.

[0063] As yet another example, in the chemical formula CY2-1, R 22 and R 24 These can be hydrogen or deuterium, independently of each other. As yet another example, in the chemical formulas CY2-1 and CY2-1(1), R 21 and R 23 They can be identical to each other. As yet another example, in the chemical formulas CY2-1 and CY2-1(1), R 21 and R 23 They can be different from one another. As yet another example, in the chemical formulas CY2-1 and CY2-1(1), R 21 and R 23 They are different from each other, R 23 The number of carbon atoms contained in R 21 The number of carbon atoms will be greater than the number of carbon atoms contained in it.

[0064] As yet another example, i) R of chemical formula CY2-1 21 ~R 24 At least one of the following, ii) R of chemical formulas CY2-2 to CY2-7 21 ~R 26 At least one of the following, iii) R of chemical formula CY2-8 23 ~R 28 At least one of the following, iv) R of chemical formula CY2-9 21 , R 24 ~R 28 One of the above, or any combination thereof, v) R of chemical formula CY2-10 21 , R 22 , R 25 ~R28 One of the above, or any combination thereof, vi) Chemical formulas CY2-1(1) to CY2-1(3), R 21 and R 23 , and vii) Chemical formulas CY2-8(1) to CY2-8(6), R 23 ~R 28 These are, independently of each other, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 Deuterated C1-C1 molecules substituted or unsubstituted with heterocycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof. 20 Alkyl, deuterated C3-C 10 Cycloalkyl groups, deuterated C1-C 10 It may be a heterocycloalkyl group or a deuterated phenyl group.

[0065] As yet another example, i) Chemical formula CY2-1, R 21 and R 23 At least one of the following (for example, in chemical formula CY2-1, R 21 and R 23 ), ii) Chemical formulas CY2-1(1) to CY2-1(3), R 21 and R 23 , and iii) Chemical formulas CY2-8(1) to CY2-8(6), R 23 ~R 28 These are, independently of each other, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 Deuterated C1-C1 molecules substituted or unsubstituted with heterocycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof. 20 Alkyl, deuterated C3-C 10 Cycloalkyl groups, deuterated C1-C 10 It may be a heterocycloalkyl group or a deuterated phenyl group.

[0066] As yet another example, i) R of chemical formula CY2-8 23 ~R 28 , ii) R of chemical formula CY2-9 21 , and R 24 ~R 28 , and iii) R of chemical formula CY2-10 21 , R 22 , and R 25 ~R 28 teeth, Independent of each other, Hydrogen or deuterium, Deuterium, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 C1-C14 is a C1-C14 molecule that is substituted or unsubstituted with a heterocycloalkyl group, a phenyl group, a biphenyl group, or any combination thereof. 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, phenyl groups, or biphenyl groups, It may be -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5).

[0067] As yet another example, i) R of chemical formula CY2-8 23 ~R 28 , ii) R of chemical formula CY2-9 21 , and R 24 ~R 28 , and iii) R of chemical formula CY2-10 21 , R 22 , and R 25 ~R 28 teeth, Independent of each other, Hydrogen, deuterium, -F, or cyano group, Deuterium, -F, cyano group, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10C1-C14 is a C1-C14 molecule that is substituted or unsubstituted with a heterocycloalkyl group, a phenyl group, a biphenyl group, or any combination thereof. 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, phenyl groups, or biphenyl groups, -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), i) R of chemical formula CY2-8 23 ~R 28 At least one of the following, ii) R of chemical formula CY2-9 21 , R 24 ~R 28 One of the above, or any combination thereof, and iii) R of chemical formula CY2-10 21 , R 22 , R 25 ~R 28 One of these, or any combination thereof, Independent of each other, Fluorine group (-F) or cyano group, or Deuterium, fluoro group, cyano group, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 C1-C fluoride substituted or unsubstituted with heterocycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof. 20 Alkyl, fluoride C3-C 10 Cycloalkyl groups, C1-C fluoride 10 Heterocycloalkyl group, fluorinated phenyl group, fluorinated biphenyl group, cyano group-containing C1-C 20 C3-C containing alkyl and cyano groups 10 Cycloalkyl groups, cyano group-containing C1-C 10 It may be a heterocycloalkyl group, a cyano group-containing phenyl group, or a cyano group-containing biphenyl group.

[0068] As yet another example, R in chemical formulas CY2-8(1) to CY2-8(6) 23 ~R 28They are independent of each other, Fluorine group (-F) or cyano group, or Deuterium, fluoro group, cyano group, C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C1-C 10 C1-C fluoride substituted or unsubstituted with heterocycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof. 20 Alkyl, fluoride C3-C 10 Cycloalkyl groups, C1-C fluoride 10 Heterocycloalkyl group, fluorinated phenyl group, fluorinated biphenyl group, cyano group-containing C1-C 20 C3-C containing alkyl and cyano groups 10 Cycloalkyl groups, cyano group-containing C1-C 10 It may be a heterocycloalkyl group, a cyano group-containing phenyl group, or a cyano group-containing biphenyl group. In yet another embodiment, R of chemical formula 3 31 and R 32 Each of the carbon atoms contained in it is 4 or more (for example, 5 or more).

[0069] Furthermore, according to other embodiments, the organometallic compound represented by chemical formula 1 may satisfy the following conditions 4 and 5, or a combination thereof. <Condition 4> In chemical formula 3, R 31 This is the group represented by chemical formula 4 shown below. <Condition 5> In chemical formula 3, R 32 This is a group represented by the chemical formula 5 shown below. [ka] [ka] In chemical formulas 4 and 5, A1 to A6 are independent of each other. Hydrogen or deuterium, or Deuterium, C1-C 20 Alkyl, C3-C 10C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, C6-C 60 Aryl group, C1-C 60 It is a heteroaryl group, a phenyl group, or a biphenyl group. * indicates a bonding site with an adjacent atom.

[0070] For example, chemical formula 4 satisfies one of the following conditions 4-1 to 4-6, and / or chemical formula 5 may satisfy one of the following conditions 5-1 to 5-6. <Condition 4-1> A1-A3 are not hydrogen at the same time. <Condition 4-2> A1-A3 are independent of each other, containing deuterium, C1-C 20 Alkyl, C3-C 10 C1-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 4-3> A1 and A2 are independent of each other, deuterium, C1-C 20 Alkyl, C3-C 10 C1-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. A3 is deuterium, C1-C 20 Alkyl, C3-C 10 C2-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 4-4> A1 consists of deuterium and C1-C, which are independent of each other. 20 Alkyl, C3-C 10 C1-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. A2 and A3 are independent of each other, deuterium, C1-C 20 Alkyl, C3-C 10 C2-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 4-5> A1 is hydrogen, deuterium, -CH3, -CH2D, -CHD2, or -CD3. A2 is deuterium, C1-C 20 Alkyl, C3-C 10 C1-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. A3 is deuterium, C1-C 20 Alkyl, C3-C 10 C2-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 4-6> A1 is hydrogen, deuterium, -CH3, -CH2D, -CHD2, or -CD3. A2 and A3 are independent of each other, deuterium, C1-C 20 Alkyl, C3-C 10 C2-C 20 Alkyl, C3-C10 It is a cycloalkyl group, a phenyl group, or a biphenyl group.

[0071] <Condition 5-1> A4-A6 are not hydrogen at the same time. <Condition 5-2> A4-A6 are independent of each other, containing deuterium and C1-C 20 Alkyl, C3-C 10 C1-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 5-3> A4 and A5 are independent of each other, deuterium, C1-C 20 Alkyl, C3-C 10 C1-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. A6 is deuterium, C1-C 20 Alkyl, C3-C 10 C2-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 5-4> A4 consists of deuterium and C1-C, which are independent of each other. 20 Alkyl, C3-C 10 C1-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. A5 and A6 are independent of each other, deuterium, C1-C 20 Alkyl, C3-C 10C2-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 5-5> A4 is hydrogen, deuterium, -CH3, -CH2D, -CHD2, or -CD3. A5 is deuterium, C1-C 20 Alkyl, C3-C 10 C1-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. A6 is deuterium, C1-C 20 Alkyl, C3-C 10 C2-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 5-6> A4 is hydrogen, deuterium, -CH3, -CH2D, -CHD2, or -CD3. A5 and A6 are independent of each other, deuterium, C1-C 20 Alkyl, C3-C 10 C2-C 20 Alkyl, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group.

[0072] In yet another embodiment, R of chemical formula 3 31 ~R 33 At least one of them is independently of each other, deuterium, C1-C 20 Alkyl, C3-C 10 C3-C molecules substituted or unsubstituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof.10 It is also a cycloalkyl group. Furthermore, according to other embodiments, the organometallic compound represented by chemical formula 1 may be one of the compounds 1 to 19 shown below. [ka] [ka]

[0073] According to one embodiment, the FWQM of the emission peak in the emission spectrum or electroluminescence (EL) spectrum of the organometallic compound represented by chemical formula 1 is 100 nm or less. For example, the FWQM of the emission peak in the emission spectrum or electroluminescence spectrum of organometallic compounds is 100 nm or less, 60 nm to 100 nm, 70 nm to 100 nm, 80 nm to 100 nm, or 82 nm to 96 nm. On the other hand, according to another embodiment, the maximum emission wavelength (emission peak wavelength (λ) of the emission spectrum or electroluminescence spectrum of the organometallic compound represented by chemical formula 1 is max The range is 600nm to 660nm, or 615nm to 640nm. For example, the maximum emission wavelength (emission peak wavelength (λ) of the emission spectrum or electroluminescence spectrum of an organometallic compound. max The wavelength range is 615nm to 630nm or 620nm to 630nm.

[0074] The horizontal orientation of the transition dipole moment (TDM) of organometallic compounds represented by chemical formula 1 is 90% to 100%. For example, the horizontal orientation rates of the transition dipole moments (TDM) of organometallic compounds are, for example, 90%~99%, 90%~98%, 90%~97%, 90%~96%, 90%~95%, or 91%~95%. For example, you can refer to Evaluation Example 3 described later for a method of measuring the horizontal orientation of the transition dipole moment (TDM) of organometallic compounds. As mentioned above, because the horizontal orientation of the transition dipole moment (TDM) of organometallic compounds is high, when an organic light-emitting device containing an organometallic compound is driven, an electric field is emitted in a direction substantially horizontal to the film containing the organometallic compound, and optical loss due to waveguide modes and / or surface plasmon polariton modes can be reduced. Because such a mechanism allows for high efficiency in extracting light from electronic elements (i.e., in electronic elements containing a film containing an organometallic compound (e.g., a light-emitting layer described later), such as organic light-emitting devices, electronic elements employing organometallic compounds, such as organic light-emitting devices, can achieve high luminous efficiency.

[0075] The quantum luminescence efficiency (PLQY in film) of an organometallic compound represented by chemical formula 1 is 90% to 100%. For example, the quantum luminescence efficiencies of organometallic compound films are 91%-100%, 92%-100%, 93%-100%, 94%-100%, 95%-100%, 96%-100%, 97%-100%, 98%-100%, 99%-100%, or 100%. According to one embodiment, the quantum luminescence efficiency of the organometallic compound film is 95%~99%, 96%~99%, 97%~99%, and 98%~99%.

[0076] The method for synthesizing the organometallic compound represented by chemical formula 1 can be understood by those skilled in the art by referring to the synthesis examples described later. Accordingly, the organometallic compound represented by chemical formula 1 is suitable for use as a dopant for the light-emitting layer in the organic layer of an organic light-emitting device, for example, in the organic layer. In other aspects, the present invention provides an organic light-emitting device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and containing a light-emitting layer, wherein the organic layer contains at least one organometallic compound represented by chemical formula 1.

[0077] The organic light-emitting element, by comprising an organic layer containing an organometallic compound represented by the aforementioned chemical formula 1, can have a low driving voltage, high external quantum efficiency, a relatively small FWQM, and a long lifespan. The organometallic compound represented by chemical formula 1 is used between a pair of electrodes in an organic light-emitting device. For example, organometallic compounds represented by chemical formula 1 are included in the light-emitting layer. In this case, the organometallic compound acts as a dopant, and the luminescent layer may further contain the 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 can emit red or green light.

[0078] In this specification, "(the organic layer) contains one or more organometallic compounds" is interpreted as "(the organic layer) may contain one organometallic compound belonging to the category of chemical formula 1, or two or more different organometallic compounds belonging to the category of chemical formula 1." For example, the organic layer may contain only compound 1 as an 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 contain compound 1 and compound 2 as organometallic compounds. In this case, compound 1 and compound 2 may exist in the same layer (for example, both compound 1 and compound 2 may exist in the light-emitting layer).

[0079] The first electrode is an anode, which is a hole injection electrode, and the second electrode is a cathode, which is an electron injection electrode, or the first electrode is a cathode, which is an electron injection electrode, and the second electrode is an anode, which is a hole injection electrode. For example, in an organic light-emitting device, the first electrode is an anode, 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. The hole transport region includes a hole injection 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. In this specification, "organic layer" is a term that refers to one and / or more layers disposed between the first electrode and the second electrode in an organic light-emitting device. The "organic layer" may include not only organic compounds but also organometallic complexes containing metals.

[0080] Figure 3 is a cross-sectional view showing a schematic configuration of an organic light-emitting element 10 according to one embodiment of the present invention. The structure and manufacturing method of an organic light-emitting element according to one embodiment of the present invention will be described below with reference to Figure 3. 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 that order.

[0081] A substrate may be additionally placed below the first electrode 11 or above the second electrode 19. While substrates commonly used for organic light-emitting devices can be used, glass substrates or transparent plastic substrates that offer superior mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofing can also be used.

[0082] The first electrode 11 is formed, for example, by providing the material for the first electrode on the upper part of the substrate using a vapor deposition method or a sputtering method. The first electrode 11 is the anode. The material for the first electrode may include a material having a high work function to facilitate hole injection. The first electrode 11 is a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. For the first electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., can be used. Alternatively, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) can be used. The first electrode 11 may have a single-layer structure or a multilayer structure including two or more layers. For example, the first electrode 11 can have a three-layer structure of ITO / Ag / ITO.

[0083] An organic layer 15 is placed on top of the first electrode 11. The organic layer 15 may include a hole transport region, an emissive layer, and an electron transport region. The hole transport region is located between the first electrode 11 and the light-emitting layer. The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof. The hole transport region may consist only of a hole injection layer, or it may consist only of a hole transport layer. Alternatively, the hole transport region may have a structure of hole injection layer / hole transport layer or hole injection layer / hole transport layer / electron blocking layer, stacked sequentially from the first electrode 11. If the hole transport region includes a hole injection layer, the hole injection layer is formed on top of the first electrode 11 using a variety of methods such as vacuum deposition, spin coating, casting, and LB (Langmuir-Blodgett) method.

[0084] 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 desired structure of the hole injection layer, and its thermal properties. For example, the deposition temperature is approximately 100 to 500°C, and the vacuum level is approximately 10°C. -8 ~about 10 -3 Torr is selected from a range of approximately 0.01 to 100 Å / sec for the deposition rate. 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 desired structure of the hole injection layer, and its thermal properties. However, the coating speed is typically between 2,000 rpm and 5,000 rpm, and the heat treatment temperature for solvent removal after coating is selected from a temperature range of approximately 80°C to 200°C.

[0085] The conditions for forming the hole transport layer and electron blocking layer refer to the conditions for forming the hole injection layer. The hole transport region may include, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine) (TCTA), polyaniline / dodecylbenzenesulfonic acid) (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), compounds represented by chemical formula 201 shown below, compounds represented by chemical formula 202 shown below, or any combination thereof. TIFF0007843595000059.tif61163TIFF0007843595000060.tif104154 [ka] [ka]

[0086] Chemical formula 201, Ar 101 and Ar 102 These are, independently of each other, 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, C1-C 60 Alkyl alkyl group, C2-C60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 The group may be a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, or any combination thereof, substituted or unsubstituted, and may be a phenylene group, pentarenylene group, indenylene group, naphthylene group, azurenylene group, heptarenylene group, acenaphthylene group, fluorenylene group, phenalenylene group, phenantrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenyrenylene group, naphthasenylene group, picenylene group, perillenylene group, or pentasenylene group.

[0087] In chemical formula 201, xa and xb are independent integers between 0 and 5, or 0, 1, or 2. For example, xa could be 1 and xb could be 0. In chemical formulas 201 and 202, R 101 ~R 108 , R 111 ~R 119 , and R 121 ~R 124 They are independent of each other, 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, C1-C 10 Alkyl groups (e.g., methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.) or C1-C 10 Alkoxy groups (e.g., methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, etc.), C1-C substituted with 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. 10 Alkyl alkyl group or C1-C 10 Alkoxy group, or 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, C1-C 10 Alkyl alkyl group, C1-C 10 The group may be an alkoxy group, or any combination thereof, substituted or unsubstituted, or a phenyl group, naphthyl group, anthracenyl group, fluorenyl group, or pyrenyl group.

[0088] In chemical formula 201, R 109 This includes 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, C1-C 20 Alkyl alkyl group, C1-C 20 The group may be a phenyl group, naphthyl group, anthracenyl group, pyridinyl group, or any combination thereof, substituted or unsubstituted.

[0089] According to one embodiment, the compound represented by chemical formula 201 can also be represented by chemical formula 201A shown below. [ka] In chemical formula 201A, R 101 , R 111 , R 112 and R 109 For a detailed explanation of this matter, please refer to the section mentioned above.

[0090] For example, the hole transport region may include one of the compounds HT1 to HT21 shown below, or any combination thereof. [ka] [ka] [ka] [ka] [ka]

[0091] The thickness of the hole transport region is approximately 100 Å to 10,000 Å, for example, approximately 100 Å to 1,000 Å. If the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, the thickness of the hole injection layer is approximately 100 Å to approximately 10,000 Å, for example, approximately 100 Å to approximately 1,000 Å, and the thickness of the hole transport layer is approximately 50 Å to approximately 2,000 Å, for example, approximately 100 Å to approximately 1,500 Å. When the hole transport region, hole injection layer, and the thickness of the hole transport layer satisfy the aforementioned range, satisfactory hole transport characteristics can be obtained without a substantial increase in the driving voltage. In addition to the materials mentioned above, the hole transport region may further contain charge-generating materials to improve conductivity. Charge-generating materials can be dispersed uniformly or non-uniformly within the hole transport region.

[0092] Charge-generating materials include, for example, p-dopants. The p-dopant may be a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof. For example, the p-dopant may be a quinone derivative such as tetracyanoquinone dimethane (TCNQ), 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4-TCNQ), F6-TCNNQ, a metal oxide such as tungsten oxide and molybdenum oxide, a cyano group-containing compound such as compound HT-D1 shown below, or any combination thereof. TIFF0007843595000069.tif103128

[0093] The hole transport region may further include a buffer layer. The buffer layer can compensate for the optical resonance distance caused by the wavelength of light emitted from the light-emitting layer, thereby increasing efficiency. On the other hand, 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 as described later, or any combination thereof. For example, if the hole transport region includes an electron blocking layer, the following materials can be used as the electron blocking layer material: mCP, compound HT21, or any combination thereof.

[0094] An emissive layer can be formed on top of the hole transport region using methods such as vacuum deposition, spin coating, casting, or LB (Laser-Blocked) method. When forming an emissive layer by vacuum deposition and spin coating, the deposition and coating conditions vary depending on the compound used, but are generally selected from a range of conditions that are almost the same as those used for forming a hole injection layer. The light-emitting layer comprises a host and a dopant, the dopant may comprise an organometallic compound represented by chemical formula 1 as described herein.

[0095] The host may contain TPBi, TBADN, ADN (also known as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, compound H52, or any combination thereof, as listed below. TIFF0007843595000070.tif96162TIFF0007843595000071.tif82162

[0096] If the organic light-emitting element is a full-color organic light-emitting element, the light-emitting layer is patterned with a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer. Alternatively, the light-emitting layer can be modified in various ways, such as by having a structure in which a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer are laminated together, thereby emitting white light. When the luminescent layer contains a host and a dopant, the dopant content is generally selected from a range of approximately 0.01 to approximately 15 parts by weight, based on approximately 100 parts by weight of the host. The thickness of the luminescent layer is approximately 100 Å to 1,000 Å, for example, approximately 200 Å to 600 Å. When the thickness of the light-emitting layer satisfies the aforementioned range, excellent light-emitting characteristics can be achieved without a substantial increase in the driving voltage.

[0097] Next, an electron transport region is placed above the light-emitting layer. The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure. The electron transport layer may have a single-layer structure or a multilayer structure containing two or more different materials. The formation conditions for the hole blocking layer, electron transport layer, and electron injection layer in the electron transport region refer to the formation conditions for the hole injection layer.

[0098] 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. [ka]

[0099] Alternatively, the hole blocking layer may include a host, an electron transport layer material (described later), an electron injection layer material, or any combination thereof. The thickness of the hole blocking layer is approximately 20 Å to 1,000 Å, for example, approximately 30 Å to 300 Å. If the thickness of the hole blocking layer satisfies the aforementioned range, excellent hole blocking characteristics can be obtained without a substantial increase in the driving voltage.

[0100] The electron transport layer may include BCP, BPhen, Alq3, BAlq, TAZ, NTAZ, or any combination thereof. TIFF0007843595000073.tif88147

[0101] Alternatively, the electron transport layer may include at least one of the compounds ET1 to ET25 shown below and any combination thereof. [ka] [ka] [ka] [ka]

[0102] The thickness of the electron transport layer is approximately 100 Å to 1,000 Å, for example, approximately 150 Å to 500 Å. If the thickness of the electron transport layer satisfies the aforementioned range, satisfactory electron transport characteristics can be obtained without a substantial increase in the driving voltage. The electron transport layer may contain metal-containing materials in addition to the materials mentioned above.

[0103] Metal-containing materials may include Li complexes. The Li complex may include, for example, the compounds ET-D1 or ET-D2 shown below. [ka]

[0104] Furthermore, the electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 19. The electron injection layer may contain LiF, NaCl, CsF, Li2O, BaO, or any combination thereof. The thickness of the electron injection layer is approximately 1 Å to 100 Å, for example, approximately 3 Å to 90 Å. If the thickness of the electron injection layer satisfies the aforementioned range, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0105] A second electrode 19 is positioned on top of the organic layer 15. The second electrode 19 is the cathode. As the material for the second electrode 19, a metal, alloy, electrically conductive compound, or a combination thereof having a relatively low work function can be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag), which can be used as materials for forming the second electrode 19. Alternatively, various modifications are possible, such as using ITO or IZO to form a transmissive second electrode 19 in order to obtain a front-facing light-emitting element.

[0106] The above describes organic light-emitting devices with reference to Figure 3, but they are not the only types of light-emitting devices that exist. Furthermore, from another perspective, organic light-emitting devices can also be included in electronic devices. Therefore, an electronic device including an organic light-emitting element is provided. Electronic devices may include, for example, displays, lighting, sensors, and the like.

[0107] In this specification, C5-C 30A carbocyclic group is a saturated or unsaturated ring group that has only 5 to 30 carbon atoms as ring-forming atoms. C5-C 30 A carbon ring group can be either a monocyclic or polycyclic group. (at least one R 1a (Substituted or not substituted) C5-C 30 A "carbon ring group" is, for example, (at least one R 1a It may contain, substituted or unsubstituted, adamantane group, norbornane group (bicyclo[2.2.1]heptane group), norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane 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, fluorene group, etc.

[0108] In this specification, C1-C 30 A heterocyclic group is a saturated or unsaturated ring group having, in addition to 1 to 30 carbon atoms as ring-forming atoms, at least one heteroatom selected from N, O, P, Si, S, Ge, Se, and B. C1-C 30 A heterocyclic group can be either a monocyclic or polycyclic group. (at least one R 1a A C1-C30 heterocyclic group (substituted or unsubstituted) is, for example, (at least one R 1aSubstituted or unsubstituted, thiophene group, furan group, pyrrole group, silole group, borol group, phosphole group, selenofen group, gelmol group, benzothiophene group, benzofuran group, indole group, benzosilole group, benzoborol group, benzophosphole group, benzoselenophene group, benzogermol group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzosilole group, dibenzoborol group, dibenzophosphole group, dibenzo Azabenzoselenophen group, dibenzogermol group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilol group, azabenzobolol group, azabenzophosphole group, azabenzoselenophene group, azabenzogermol group, azadibenzothiophene group, azadibenzofuran group, azacarb Zole group, azafluorene group, azadibenzosilol group, azadibenzobolol group, azadibenzophosphole group, azadibenzoselenophene group, azadibenzogermole 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, quinoxaline group, quinazoline group, f It may contain an enanthroline group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, etc.

[0109] In this specification, C1-C 60 Alkyl groups refer to linear or branched saturated aliphatic hydrocarbon monovalent groups having 1 to 60 carbon atoms, C1-C 60 The alkylene group is C1-C 60 This refers to a divalent group that has the same structure as an alkyl group. In this specification, C1-C60 Alkyl alkyl group, C1-C 20 Alkyl alkyl groups and / or C1-C 10 Examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, 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, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, or any combination thereof. This may include substituted or unsubstituted methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, isobutyl groups, tert-butyl groups, n-pentyl groups, tert-pentyl groups, neopentyl groups, isopentyl groups, sec-pentyl groups, 3-pentyl groups, sec-isopentyl groups, n-hexyl groups, isohexyl groups, sec-hexyl groups, tert-hexyl groups, n-heptyl groups, isoheptyl groups, sec-heptyl groups, tert-heptyl groups, n-octyl groups, isooctyl groups, sec-octyl groups, tert-octyl groups, n-nonyl groups, isononyl groups, sec-nonyl groups, tert-nonyl groups, n-decyl groups, isodecyl groups, sec-decyl groups, or tert-decyl groups. For example, chemical formula 9-33 is a branched C6 alkyl group, which can be seen as a tert-butyl group substituted with two methyl groups.

[0110] In this specification, C1-C 60 The alkoxy group is -OA 101 (Here, A 101 C1-C 60 This refers to a monovalent group having the chemical formula (which is an alkyl group). In this specification, C1-C 60 Alkoxy group, C1-C 20Alkoxy group, or C1-C 10 Examples of alkoxy groups may include methoxy, ethoxy, propoxy, butoxy, or pentoxy groups. In this specification, C3-C 10 Cycloalkyl groups are C3-C 10 This refers to a monovalent saturated hydrocarbon ring group, C3-C 10 The cycloalkylene group is C3-C 10 This refers to a divalent group having the same structure as a cycloalkyl group. In this specification, C3-C 10 Examples of cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornyl), and bicyclo[2.2.2]octyl.

[0111] In this specification, C1-C 10 A heterocycloalkyl group is a C1-C alkyl group containing at least one heteroatom selected from N, O, P, Si, S, Ge, Se, and B as a ring-forming atom. 10 This refers to a monovalent monocyclic group, C1-C 10 The heterocycloalkylene group is C1-C 10 This refers to a divalent group having the same structure as a heterocycloalkyl group. In this specification, C1-C 10 Examples of heterocycloalkyl groups may include siloranyl, silinanyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, and tetrahydrothiophenyl groups. In this specification, C2-C 60 The alkenyl group is C2-C 60 The alkyl group has a structure containing one or more carbon-carbon double bonds in the middle or terminal, and specific examples of such groups include ethenyl, propenyl, and butenyl groups. In this specification, C2-C 60 The alkenylene group is C2-C 60This refers to a divalent group that has the same structure as an alkenyl group.

[0112] In this specification, C2-C 60 The alkynyl group is C2-C 60 The alkyl group has a structure containing one or more carbon-carbon triple bonds in the middle or terminal, and specific examples include the ethynyl group and the propynyl group. In this specification, C2-C 60 The alkynylene group is C2-C 60 This refers to a divalent group that has the same structure as an alkynyl group. In this specification, C3-C 10 The cycloalkenyl group is C3-C 10 A monovalent monocyclic group is a group that has at least one carbon-carbon double bond within the ring but does not possess aromaticity. Specific examples include the cyclopentenyl group, cyclohexenyl group, and cycloheptenyl group. In this specification, C3-C 10 The cycloalkenylene group is C3-C 10 This refers to a divalent group that has the same structure as a cycloalkenyl group. In this specification, C1-C 10 A heterocycloalkenyl group is a C1-C group containing at least one heteroatom selected from N, O, P, Si, S, Ge, Se, and B as a ring-forming atom. 10 It is a monovalent monocyclic group and has at least one double bond within the ring. C1-C 10 Specific examples of heterocycloalkenyl groups include the 2,3-dihydrofuranyl group and the 2,3-dihydrothiophenyl group. In this specification, C1-C 10 The heterocycloalkenylene group is C1-C 10 This refers to a divalent group that has the same structure as a heterocycloalkenyl group.

[0113] In this specification, C6-C 60 The aryl group is C6-C 60 This refers to a monovalent group having a carbon-ring aromatic system, C6-C 60The arylene group is C6-C 60 This refers to a divalent group having a carbocyclic aromatic system. C6-C 60 Specific examples of aryl groups include phenyl, naphthyl, anthracenyl, phenantrenyl, pyrenyl, and chrysenyl groups. 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 with each other. In this specification, C7-C 60 The alkylaryl group is at least one C1-C 60 C6-C substituted with alkyl group 60 It means an aryl group. In this specification, C1-C 60 A heteroaryl group is a monovalent group having a C1-C60 cyclic aromatic system, containing at least one heteroatom selected from N, O, P, Si, S, Ge, Se, and B as a ring-forming atom. 60 The heteroarylene group contains at least one heteroatom selected from N, O, P, Si, S, Ge, Se, and B as a ring-forming atom, C1-C 60 This refers to a divalent group having a carbocyclic aromatic system. C1-C 60 Specific examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridadinyl, triazinyl, quinolinyl, and isoquinolinyl groups. C1-C 60 Heteroaryl group and C1-C 60 If a heteroarylene group contains two or more rings, these two or more rings can be fused together.

[0114] In this specification, C2-C 60 The alkyl heteroaryl group is at least one C1-C 60 C1-C substituted with alkyl group 60 It means a heteroaryl group. In this specification, C6-C 60 The aryloxy group is -OA 102 (Here, A102 C6-C 60 (It is an aryl group) and C6-C 60 The arylthio group is -SA 103 (Here, A 103 C6-C 60 It indicates that it is an aryl group. In this specification, a monovalent non-aromatic condensed polycyclic group means a monovalent group (for example, having 8 to 60 carbon atoms) in which two or more rings are fused to each other, containing only carbon as the ring-forming atom, and having non-aromaticity as a whole molecule. Specific examples of monovalent non-aromatic condensed polycyclic groups include the fluorenyl group. In this specification, a divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.

[0115] In this specification, a monovalent non-aromatic heterocondensed polycyclic group means a monovalent group (for example, having 1 to 60 carbon atoms) in which two or more rings are fused to each other, and which, in addition to carbon, contains heteroatoms selected from N, O, P, Si, S, Ge, Se, and B as ring-forming atoms, and the entire molecule is non-aromatic. Monovalent non-aromatic heterocondensed polycyclic groups include carbazolyl groups, among others. In this specification, a divalent non-aromatic heterocondensed polycyclic group means a divalent group having the same structure as a monovalent non-aromatic heterocondensed polycyclic group.

[0116] In this specification, substituted C5-C 30 Carbocyclic group, substituted C2-C 30 Heterocyclic group, substituted C1-C 60 Alkyl alkyl group, substituted C2-C 60 Alkenyl group, substituted C2-C 60 Alkynyl group, substituted C1-C 60 Alkoxy group, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocycloalkyl groups, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10Heterocycloalkenyl 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 alkylheteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituents of the substituted monovalent non-aromatic heterocondensed polycyclic group are independent of each other. Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino 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 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, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C7-C 60 Alkylaryl 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 )(Q15 ), -Ge(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ) or any combination thereof, C1-C 60 Alkyl 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, amidino 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 alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C7-C 60 Alkylaryl 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 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 any combination thereof, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C7-C 60 Alkylaryl 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, 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 It could be any combination of those.

[0117] In this specification, Q1 to Q9, Q 11 ~Q 19 Q 21 ~Q 29 , and Q 31 ~Q 39 These are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, deuterium, C1-C 60 Alkyl alkyl group, C6-C 60A C1-C group substituted or unsubstituted with an aryl group, or any combination thereof. 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, deuterium, C1-C 60 Alkyl alkyl group, C6-C 60 C6-C 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 may be a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic heterocondensed polycyclic group.

[0118] For example, in this specification, Q1 to Q9, Q 11 ~Q 19 Q 21 ~Q 29 , and Q 31 ~Q 39 They are independent of each other, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2, or Deuterium, C1-C 10 The group may be an n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, phenyl group, biphenyl group, or naphthyl group, substituted or unsubstituted with an alkyl group, phenyl group, or any combination thereof. In this specification, "Deuterated C1-C 60Alkyl group (or deuterated C1-C 20 Alkyl alkyl groups, deuterated C2-C 20 "Alkyl groups, etc." refers to C1-C atoms substituted with at least one deuterium atom. 60 Alkyl group (or C1-C substituted with at least one deuterium) 20 Alkyl group, C2-C substituted with at least one deuterium 20 This refers to alkyl groups, etc. For example, "deuterated C1 alkyl group (i.e., deuterated methyl group)" includes -CD3, -CD2H, and -CDH2. In this specification, "Deuterated C3-C 10 A "cycloalkyl group" is a C3-C3 alkyl group substituted with at least one deuterium atom. 10 This refers to a cycloalkyl group. Deuterated C3-C 10 For example, one can refer to chemical formula 10-501 above as an example of a "cycloalkyl group".

[0119] In this specification, "C1-C fluoride" 60 Alkyl group (or C1-C fluoride) 20 (Alkyl alkyl groups, etc.), Fluoride C3-C 10 "Cycloalkyl group" and "C1-C fluoride" 10 A heterocycloalkyl group is a C1-C alkyl group, each substituted with at least one fluoro group (-F). 60 Alkyl group (or C1-C 20 (Alkyl alkyl groups, etc.), C3-C 10 Cycloalkyl groups and C1-C 10 This refers to heterocycloalkyl groups. For example, "C1 alkyl fluoride (i.e., methyl fluoride group)" includes -CF3, -CF2H, and -CFH2. "Fluoride C1-C 60 Alkyl group (or C1-C fluoride) 20 (Alkyl alkyl groups, etc.), Fluoride C3-C 10 "Cycloalkyl group" or "C1-C fluoride" 10 "Hypercycloalkyl group" is i) Fully fluorinated C1-C, in which all hydrogen atoms in each group are replaced by fluoro groups. 60 Alkyl alkyl groups (or fully fluorinated C1-C 20 Alkyl alkyl groups, etc.), fully fluorinated C3-C 10 Cycloalkyl groups, or fully fluorinated C1-C 10 It is a heterocycloalkyl group, or ii) Not all hydrogen atoms in each group are replaced by fluoro groups; partially fluorinated C1-C 60 Alkyl group (or partially fluorinated C1-C 20 (Alkyl alkyl groups, etc.), partially fluorinated C3-C 10 Cycloalkyl groups or partially fluorinated C1-C 10 It may be a heterocycloalkyl group.

[0120] In this specification, "(C1-C 20 The alkyl group "X" is at least one C1-C 20 This indicates an "X" group substituted with an alkyl group. For example, in this specification, "(C1-C 20 Alkyl)C3-C 10 A "cycloalkyl group" is defined as a group with at least one C1-C 20 C3-C substituted with alkyl group 10 This indicates a cycloalkyl group, and is defined as "(C1-C 20 A "(alkyl)phenyl group" is defined as at least one C1-C 20 This shows a phenyl group substituted with an alkyl group. An example of a (C1 alkyl)phenyl group is the toluyl group. In this specification, "azaindole group, azabenzoborol group, azabenzophosphole group, azaindene group, azabenzosilol group, azabenzogermol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborol group, azadibenzophosphole group, azafluorene group, azadibenzosilol group, azadibenzogermol group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group" each This refers to a heterocycle that has the same backbone as "indole group, benzoborol group, benzophosphole group, indene group, benzosilol group, benzogermol group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborol group, dibenzophosphole group, fluorene group, dibenzosilol group, dibenzogermole group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group," but in which at least one of the carbon atoms forming the ring is substituted with nitrogen.

[0121] The following describes in more detail a compound and an organic light-emitting element according to one embodiment of the present invention, with reference to synthesis examples and examples. However, the present invention is not limited to the following synthesis examples and examples. In the synthesis example below, the expression "'B' was used instead of 'A'" means that the amount of "B" used and the amount of "A" used are the same on a molar equivalent basis.

[0122] <Examples of compound synthesis> <Synthesis example 1 (compound 1)> [ka]

[0123] [Synthesis of intermediates L1-3] 1.9 g (7.2 mmol) of 2-chloro-4-iodonicotinaldehyde was mixed with 60 ml of acetonitrile and 15 ml of water. Then, 0.4 g (0.5 mmol) of PdCl2(PPh3)2, 1.0 g (7.2 mmol) of 3-fluorophenylboronic acid, and 2.5 g (18.0 mmol) of K2CO3 were added, and the mixture was heated under reflux at 85°C for 16 hours. The resulting product was concentrated under reduced pressure, and the organic layer extracted by adding dichloromethane and water was dried over magnesium sulfate, then distilled under reduced pressure, and purified by liquid chromatography to obtain intermediate L1-3 (1.5 g (87% yield)). LC-MS m / z = 236(M+H) +

[0124] [Synthesis of intermediate L1-2] 5.4 g (15.8 mmol) of (methoxymethyl)triphenylphosphonium chloride was mixed with 50 ml of anhydrous ether, and then 16 ml of 1.0 M potassium tert-butoxide solution was added dropwise, and the mixture was stirred at room temperature for about 1 hour. Subsequently, intermediate L1-3 (1.5 g (6.3 mmol)), which had been mixed with 30 ml of anhydrous tetrahydrofuran (THF), was gradually added dropwise, and the mixture was stirred at room temperature for 18 hours. The resulting product was then extracted by adding water and ethyl acetate, and the resulting organic layer was dried over magnesium sulfate, followed by vacuum distillation and purification by liquid chromatography to obtain intermediate L1-2 (1.6 g (yield 96%)). LC-MS m / z = 264(M+H) +

[0125] [Synthesis of intermediate L1-1] Intermediate L1-2 (1.4 g (5.1 mmol)) was mixed with 40 ml of dichloromethane, and 3.0 ml of methanesulfonic acid was gradually added dropwise. The mixture was then stirred at room temperature for approximately 18 hours. The resulting product was then extracted with a saturated sodium bicarbonate aqueous solution, and the resulting organic layer was dried over magnesium sulfate, followed by vacuum distillation and purification by liquid chromatography to obtain intermediate L1-1 (1.0 g (85% yield)). LC-MS m / z=232(M+H) +

[0126] [Synthesis of intermediate L1] Intermediate L1-1 (1.0 g (4.1 mmol)) was mixed with 40 ml of tetrahydrofuran (THF) and 10 ml of water. 0.9 g (6.2 mmol) of 3,5-dimethylphenylboronic acid, 0.09 g (0.4 mmol) of Pd(OAc)2, 0.35 g (0.82 mmol) of Sphos, and 1.4 g (10.3 mmol) of K2CO3 were added, and the mixture was heated under reflux for one day. The resulting product was extracted with ethyl acetate and water, and the resulting organic layer was dried over magnesium sulfate, then distilled under reduced pressure, and purified by liquid chromatography to obtain intermediate L1 (1.1 g (85% yield)). LC-MS m / z=302(M+H) +

[0127] [Synthesis of intermediate L1 dimer] Intermediate L1 (1.05 g (3.4 mmol)) and iridium chloride (0.6 g (1.6 mmol)) were mixed with 40 mL of ethoxyethanol and 15 mL of distilled water, and then heated under reflux for 24 hours. The resulting product was cooled to room temperature, the resulting solid was filtered, and the mixture was thoroughly washed with water, methanol, and hexane in that order. The resulting solid was then dried in a vacuum oven to obtain the intermediate L1Dimer (1.1 g).

[0128] [Synthesis of Compound 1] The intermediate L1Dimer (1.0 g (0.63 mmol)), 3,7-diethylnonane-4,6-dione (4.5 mmol), and Na2CO3 (0.48 g (4.5 mmol)) were mixed with 40 mL of ethoxyethanol and stirred at 90°C for 24 hours. The resulting product was cooled to room temperature, and the resulting solid was filtered and purified by liquid chromatography to obtain compound 1 (0.6 g (47% yield)). LC-MS m / z = 1007(M+H) +

[0129] <Synthesis example 2 (compound 2)> [ka]

[0130] [Synthesis of intermediate L2-5] After mixing 15 g (130 mmol) of dichloromethyl methyl ether with 200 ml of dichloromethane, 15 ml (130 mmol) of SnCl4 was gradually added at 0°C and the mixture was stirred for approximately 2 hours. 16.5 g (103 mmol) of 1-fluoro-7-methylnaphthalene, mixed with 100 ml of CH2Cl2, was gradually added dropwise, and the mixture was stirred at room temperature for approximately 16 hours. After the reaction was complete, the reaction mixture was placed in 150 ml of ice water, and the extracted organic layer was dried over magnesium sulfate, distilled under reduced pressure, and then purified by liquid chromatography to obtain intermediate L2-5 (12.2 g (yield 63%)). LC-MS m / z = 189(M+H) +

[0131] [Synthesis of intermediate L2-4] Intermediate L2-5 (10 g (53.1 mmol)), 6.7 g (64.2 mmol) of malonic acid, and 6.3 ml (64.2 mmol) of piperidine were mixed with 80 ml of pyridine, and then stirred at 90°C for approximately 18 hours. After the reaction was complete, pyridine was distilled under reduced pressure, and water was added dropwise to the reaction mixture. The resulting product was acidified to approximately pH 4 with a 4N-HCl aqueous solution, and the resulting solid was filtered and washed several times with hexane. The compound obtained therefrom was dried without purification to obtain intermediate L2-4 (11g (75% yield)). LC-MS m / z=231(M+H) +

[0132] [Synthesis of intermediate L2-3] Intermediate L2-4 (11 g (47.8 mmol)) was mixed with 250 ml of dry acetone, then 5.5 ml (57.4 mmol) of ethyl chloroformate was added at room temperature, and 17 ml (119.5 mmol) of triethylamine was gradually added dropwise. The reaction mixture was stirred at room temperature for 2 hours, then 6.2 g (95.6 mmol) of sodium azide mixed with 100 ml of water was gradually added dropwise at 0°C, and the mixture was stirred for approximately 1 hour. After the reaction was complete, the reaction mixture was placed in ice water and stirred. The resulting solid was then filtered to obtain intermediate L2-3 (11g (90% yield)) without any purification steps.

[0133] [Synthesis of intermediate L2-2] After mixing 56 ml of tributylamine with 170 ml of diphenyl ether, intermediate agent L2-3 (5 g (19.6 mmol)) mixed with 170 ml of diphenyl ether was gradually added dropwise, and the mixture was heated and stirred for approximately 6 hours. After the reaction was complete, the mixture was cooled to room temperature, then 300 ml of hexane was added and the mixture was stirred at room temperature for about 1 hour. The resulting solid was filtered, and intermediate L2-2 (2.4 g (55% yield)) was obtained without any further purification steps. LC-MS m / z=228(M+H) +

[0134] [Synthesis of intermediate L2-1] Intermediate L2-2 (2.4g (10.6 mmol)) was dissolved in 380ml of POCl, and then heated and stirred for approximately 18 hours. After the reaction was complete and the mixture was cooled, it was gradually added dropwise to 200 ml of ice water and neutralized with a saturated sodium bicarbonate solution. The organic layer extracted with dichloromethane was dried over magnesium sulfate, then distilled under reduced pressure, and purified by liquid chromatography to obtain intermediate L2-1 (2.0 g (80% yield)). LC-MS m / z = 246(M+H) +

[0135] [Synthesis of intermediate L2] Except for using intermediate L2-1 instead of intermediate L1-1, the same method as the synthesis of intermediate L1 in Synthesis Example 1 was used to obtain intermediate L2 (1.8g (yield 73%)). LC-MS m / z = 316(M+H) +

[0136] [Synthesis of the intermediate L2Dimer] Except for using intermediate L2 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L2Dimer.

[0137] [Synthesis of Compound 2] Except for using intermediate L2Dimer instead of intermediate L1Dimer, the same method as the synthesis of compound 1 in synthesis example 1 was used to obtain compound 2 (0.6g (yield 40%)). LC-MS m / z = 10³⁵(M + H) +

[0138] <Synthesis example 3 (compound 3)> [ka]

[0139] [Synthesis of intermediate L3] Intermediate L1 (2.0 g (6.6 mmol)) was mixed with 80 ml of anhydrous tetrahydrofuran (THF), and then 1.6 M BuLi solution (7.3 mmol) in 4.6 ml of hexane was gradually added at -78°C. After approximately 2 hours, 1.3 ml (9.9 mmol) of chlorotriphenylsilane was gradually added dropwise, and the mixture was stirred at room temperature for 18 hours. After the reaction was complete, the organic layer obtained by extraction with 60 ml of ethyl acetate and water was dried over magnesium sulfate and distilled under reduced pressure. The intermediate L3 (1.1 g (45% yield)) was obtained by purification using liquid chromatography. LC-MS m / z = 374(M+H) +

[0140] [Synthesis of the intermediate L3Dimer] Except for using intermediate L3 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L3Dimer.

[0141] [Synthesis of Compound 3] Compound 3 (0.7g (45% yield)) was obtained using the same method as the synthesis of compound 1 in Synthesis Example 1, except that intermediate L3Dimer was used instead of intermediate L1Dimer. LC-MS m / z=1151(M+H) +

[0142] <Synthesis example 4 (compound 4)> [ka]

[0143] [Synthesis of intermediates L4-6] Except for using (3-bromo-5-(trofluoromethyl)phenyl)boronic acid instead of 3-fluorophenylboronic acid, the same method as the synthesis of intermediates L1-3 in Synthesis Example 1 was used to obtain intermediate L4-6 (6.2g (yield 71%)). LC-MS m / z = 364(M+H) +

[0144] [Synthesis of intermediates L4-5] Except for using intermediate L4-6 instead of intermediate L1-3, the same method as the synthesis of intermediate L1-2 in Synthesis Example 1 was used to obtain intermediate L4-5 (6.5g (yield 98%)). LC-MS m / z=392(M+H) +

[0145] [Synthesis of intermediate L4-4] Except for using intermediate L4-5 instead of intermediate L1-2, the same method as the synthesis of intermediate L1-1 in Synthesis Example 1 was used to obtain intermediate L4-4 (2.1g (yield 35%)). LC-MS m / z = 360(M+H) +

[0146] [Synthesis of intermediate L4-3] Intermediate L4-4 (2.1 g (5.9 mmol)) was mixed with 120 ml of acetonitrile, then 1.1 ml (8.9 mmol) of chlorotrimethylsilane and NaI (1.3 g (8.9 mmol)) were added, and the mixture was heated under reflux at 90°C for 36 hours. After the reaction was complete, the organic layer obtained by extraction with 60 ml of ethyl acetate and saturated sodium sulfate aqueous solution was dried over magnesium sulfate and distilled under reduced pressure. The intermediate L4-3 (2.3g (87% yield)) was obtained by purification using liquid chromatography. LC-MS m / z=452(M+H) +

[0147] [Synthesis of intermediate L4-2] Except for using intermediate L4-3 instead of intermediate L1-1, the same method as the synthesis of intermediate L1 in Synthesis Example 1 was used to obtain intermediate L4-2 (1.8g (80% yield)). LC-MS m / z = 430(M+H) +

[0148] [Synthesis of intermediate L4-1] Intermediate L4-2 (1.8 g (4.2 mmol)) was mixed with 60 ml of tetrahydrofuran (THF) and 15 ml of water. 0.9 g (5.0 mmol) of 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane, 0.1 g (0.4 mmol) of Pd(OAc)2, 0.3 g (0.8 mmol) of Sphos, and 1.5 g (10.5 mmol) of K2CO3 were added, and the mixture was heated under reflux at 80°C for 18 hours. After the reaction was complete, the reaction mixture was extracted with 50 ml of ethyl acetate, and the resulting organic layer was dried over magnesium sulfate, distilled under reduced pressure, and then purified by liquid chromatography to obtain intermediate L4-1 (1.2 g (75% yield)). LC-MS m / z=392(M+H) +

[0149] [Synthesis of intermediate L4] Intermediate L4-1 (1.2 g (3.1 mmol)) was mixed with 60 ml of ethyl alcohol, Pd / C (0.1 g (10 wt%)) was added, hydrogen was injected, and the mixture was stirred at room temperature for 18 hours. After the reaction was complete, the reaction mixture was passed through a Celite pad, concentrated under reduced pressure, and purified by liquid chromatography to obtain intermediate L4 (1.1 g (90% yield)). LC-MS m / z = 394(M+H) +

[0150] [Synthesis of the intermediate L4Dimer] Except for using intermediate L4 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L4Dimer.

[0151] [Synthesis of Compound 4] Except for using intermediate L4Dimer instead of intermediate L1Dimer, the same method as the synthesis of compound 1 in synthesis example 1 was used to obtain compound 4 (0.6g (yield 38%)). LC-MS m / z = 1191(M+H) +

[0152] <Synthesis example 5 (compound 5)> [ka]

[0153] [Synthesis of intermediate L5-3] Except for using 4-(trifluoromethyl)phenylboronic acid instead of 3-fluorophenylboronic acid, the same method as the synthesis of intermediate L1-3 in Synthesis Example 1 was used to obtain intermediate L5-3 (2.2g (yield 75%)). LC-MS m / z = 286(M+H) +

[0154] [Synthesis of intermediate L5-2] Except for using intermediate L5-3 instead of intermediate L1-3, the same method as the synthesis of intermediate L1-2 in Synthesis Example 1 was used to obtain intermediate L5-2 (2.4g (yield (99%))). LC-MS m / z = 314(M+H) +

[0155] [Synthesis of intermediate L5-1] Except for using intermediate L5-2 instead of intermediate L1-2 and trifluoromethanesulfonic acid instead of methanesulfonic acid, the same method as the synthesis of intermediate L1-1 in Synthesis Example 1 was used to obtain intermediate L5-1 (1.0 g (yield 50%)). LC-MS m / z=282(M+H) +

[0156] [Synthesis of intermediate L5] Except for using intermediate L5-1 instead of intermediate L1-1, the same method as the synthesis of intermediate L1 in Synthesis Example 1 was used to obtain intermediate L5 (0.8g (70% yield)). LC-MS m / z=352(M+H) +

[0157] [Synthesis of the intermediate L5Dimer] Except for using intermediate L5 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L5Dimer.

[0158] [Synthesis of Compound 5] Compound 5 (0.3g (40% yield)) was obtained using the same method as the synthesis of compound 1 in Synthesis Example 1, except that intermediate L5Dimer was used instead of intermediate L1Dimer. LC-MS m / z = 1107(M+H) +

[0159] <Synthesis example 6 (compound 6)> [ka]

[0160] [Synthesis of intermediate L6-2] 6.0 g (23.7 mmol) of 2-chloro-4-iodo-3-methylpyridine was mixed with 80 ml of acetonitrile and 20 ml of water. Then, 1.2 g (1.6 mmol) of PdCl2(PPh3)2, 8.4 g (26.1 mmol) of 2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trimethylsilyl)benzaldehyde and 8.2 g (59.2 mmol) of K2CO3 were added, and the mixture was heated under reflux at 85°C for 18 hours. The resulting product was concentrated under reduced pressure, and the organic layer extracted by adding ethyl acetate and water was dried over magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography to obtain intermediate L6-2 (6.1 g (80% yield)). In the case of 2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trimethylsilyl)benzaldehyde, it was obtained by the reaction equation shown above. LC-MS m / z=322(M+H) +

[0161] [Synthesis of intermediate L6-1] Except for using intermediate L6-2 instead of intermediate L1-2, the same method as the synthesis of intermediate L1-1 in Synthesis Example 1 was used to obtain intermediate L6-1 (1.7g (30% yield)). LC-MS m / z = 304(M+H) +

[0162] [Synthesis of intermediate L6] Except for using intermediate L6-1 instead of intermediate L1-1, the same method as the synthesis of intermediate L1 in Synthesis Example 1 was used to obtain intermediate L6 (1.5g (yield 73%)). LC-MS m / z = 374(M+H) +

[0163] [Synthesis of the intermediate L6Dimer] Except for using intermediate L6 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L6Dimer.

[0164] [Synthesis of Compound 6] Compound 6 (0.8g (30% yield)) was obtained using the same method as the synthesis of compound 1 in Synthesis Example 1, except that intermediate L6Dimer was used instead of intermediate L1Dimer. LC-MS m / z = 1180(M+H) +

[0165] <Synthesis example 7 (compound 7)> [ka]

[0166] [Synthesis of intermediate L7-1] Except for using 2-(3-(tert-butyl)-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 3,5-dimethylphenylboronic acid, the same method as the synthesis of intermediate L1 in Synthesis Example 1 was used to obtain intermediate L7-1. LC-MS m / z = 344(M+H) +

[0167] [Synthesis of intermediate L7] Except for using intermediate L7-1 instead of intermediate L1, the same method as the synthesis of intermediate L3 in Synthesis Example 3 was used to obtain intermediate L7 (0.9g (50% yield)). LC-MS m / z = 416(M+H) +

[0168] [Synthesis of the intermediate L7 dimer] Except for using intermediate L7 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L7Dimer.

[0169] [Synthesis of Compound 7] Except for using intermediate L7Dimer instead of intermediate L1Dimer, the same method as the synthesis of compound 1 in synthesis example 1 was used to obtain compound 7 (0.3g (yield 35%)). LC-MS m / z = 1235(M+H) +

[0170] <Synthesis example 8 (compound 8)> [ka]

[0171] [Synthesis of intermediate L8] Except for using chlorotrimethylgermane instead of chlorotrimethylsilane, the same method as the synthesis of intermediate L3 in Synthesis Example 3 was used to obtain intermediate L8 (1.1g (40% yield)). LC-MS m / z=420(M+H )+

[0172] [Synthesis of the intermediate L8Dimer] Except for using intermediate L8 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L8Dimer.

[0173] [Synthesis of Compound 8] Compound 8 (0.5g (46% yield)) was obtained using the same method as the synthesis of compound 1 in Synthesis Example 1, except that intermediate L8Dimer was used instead of intermediate L1Dimer. LC-MS m / z = 1243(M+H) +

[0174] <Synthesis example 9 (compound 9)> [ka]

[0175] [Synthesis of intermediate L9-5] 15 g (64 mmol) of 4-bromo-1-naphthaldehyde was mixed with 100 ml of chloroform, and 10 ml (96 mmol) of aminoacetaldehyde dimethyl acetal was gradually added at room temperature while stirring. After 1 hour, the mixture was heated to 100°C, the solvent was removed, and the resulting reaction mixture was cooled to room temperature. Intermediate L9-5 (20g (99% yield)) was obtained without further purification. LC-MS m / z=322(M+H) +

[0176] [Synthesis of intermediate L9-4] Intermediate L9-5 (20 g (62 mmol)) was mixed with 100 ml of chloroform, and at 0°C, 6 ml (62 mmol) of chloroformate and 9 ml (74 mmol) of trimethyl phosphite were added dropwise in that order. The resulting reaction mixture was stirred at room temperature for approximately 48 hours, and then 1.0 M (TiCl4 (250 ml (250 mmol))) was gradually added dropwise at 0°C, followed by heating under reflux for approximately 48 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, then placed in ice water. The resulting aqueous layer was washed with dichloromethane, then added to 140 g (495 mmol) of tartolate aqueous solution, neutralized with saturated NaHCO3 aqueous solution, and extracted with dichloromethane. The resulting organic layer was purified by liquid chromatography to obtain intermediate L9-4 (5.4 g (yield 34%)). LC-MS m / z=258(M+H) +

[0177] [Synthesis of intermediate L9-3] Intermediate L9-4 (5g (19 mmol)) was mixed with 60 ml of dichloromethane, and then 6.7 g (38 mmol) of metachloroperbenzoic acid (mCPBA) was added dropwise at 0°C. The reaction mixture was stirred at room temperature for approximately 18 hours, and the resulting organic layer was extracted with 6N-KOH aqueous solution. After drying with magnesium sulfate, intermediate L9-3 (5.1 g (99% yield)) was obtained without further purification.

[0178] [Synthesis of intermediate L9-2] Intermediate L9-35g (18 mmol) was mixed with 60 ml of dichloromethane, then POBr3 (6.5g (22 mmol)) was gradually added dropwise at 0°C, followed by the gradual addition of 0.8 ml (9 mmol) of dimethylformamide (DMF), and the mixture was stirred at room temperature for approximately 18 hours. After the reaction was complete, the organic layer was neutralized with saturated NaHCO3 aqueous solution, dried over magnesium sulfate, and then purified by liquid chromatography to obtain intermediate L9-2 (2.2 g (30% yield)). LC-MS m / z = 336(M+H) +

[0179] [Synthesis of intermediate L9-1] Except for using intermediate L9-2 instead of intermediate L1-1, the same method as the synthesis of intermediate L1 in Synthesis Example 1 was used to obtain intermediate L9-1 (1.6g (75% yield)). LC-MS m / z = 362(M+H) +

[0180] [Synthesis of intermediate L9] Intermediate L9-1 (1.5 g (4.1 mmol)) was mixed with 40 ml of tetrahydrofuran (THF), then Pd(PPh3)4 (0.3 g (0.3 mmol)), (4-fluorophenyl)boronic acid 0.7 g (4.9 mmol), K2CO3 (1.4 g (10.2 mmol)), and 10 ml of water were added, and the mixture was heated under reflux at 80°C for approximately 18 hours. After the reaction was complete, the organic layer obtained by extraction with ethyl acetate was dried over magnesium sulfate and then purified by liquid chromatography to obtain intermediate L9 (1.2 g (82% yield)). LC-MS m / z = 378(M+H) +

[0181] [Synthesis of the intermediate L9Dimer] Except for using intermediate L9 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L9Dimer.

[0182] [Synthesis of Compound 9] Compound 9 (0.7g (47% yield)) was obtained using the same method as the synthesis of compound 1 in Synthesis Example 1, except that intermediate L9Dimer was used instead of intermediate L1Dimer. LC-MS m / z = 1159(M+H) +

[0183] <Synthesis example 10 (compound 10)> [ka]

[0184] [Synthesis of intermediate L10-3] 6.0 g (23.7 mmol) of 2-chloro-4-iodo-3-methylpyridine was mixed with 80 ml of acetonitrile and 20 ml of water. Then, 1.2 g (1.6 mmol) of PdCl2(PPh3)2, 4.4 g (26.1 mmol) of 3-fluoro-2-formylphenylboronic acid, and 8.2 g (59.2 mmol) of K2CO3 were added, and the mixture was heated under reflux at 80°C for 18 hours. The resulting product was concentrated under reduced pressure, and the organic layer extracted by adding ethyl acetate and water was dried over magnesium sulfate, then distilled under reduced pressure, and purified by liquid chromatography to obtain intermediate L10-3 (5.0 g (85% yield)). LC-MS m / z = 250(M+H) +

[0185] [Synthesis of intermediate L10-2] Intermediate L10-3 (4.0 g (16.0 mmol)) was dissolved in 150 ml of anhydrous N,N-dimethylformamide, and 19 ml (19.2 mmol) of 1.0 M potassium tert-butoxide solution in tetrahydrofuran (THF) was gradually added dropwise at room temperature, followed by heating at 80°C for 6 hours. After the reaction was complete, the organic layer obtained by extraction with ethyl acetate and water was dried over magnesium sulfate. The reaction mixture was filtered, concentrated under reduced pressure, and then purified by liquid chromatography to obtain intermediate L10-2 (1.3 g (35% yield)). LC-MS m / z=232(M+H) +

[0186] [Synthesis of intermediate L10-1] Except for using intermediate L10-2 instead of intermediate L1-1, the same method as the synthesis of intermediate L1 in Synthesis Example 1 was used to obtain intermediate L10-1 (1.2g (70% yield)). LC-MS m / z=302(M+H) +

[0187] [Synthesis of intermediate L10] Except for using chlorodimethylphenylsilane instead of chlorotrimethylsilane, the same method as the synthesis of intermediate L3 in Synthesis Example 3 was used to obtain intermediate L10 (0.8g (46% yield)). LC-MS m / z = 436(M+H) +

[0188] [Synthesis of the intermediate L10Dimer] Except for using intermediate L10 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L10Dimer.

[0189] [Synthesis of Compound 10] Except for using intermediate L10Dimer instead of intermediate L1Dimer, the same method as the synthesis of compound 1 in Synthesis Example 1 was used to obtain compound 10 (0.35 g (yield 42%)). LC-MS m / z = 1276(M+H) +

[0190] <Synthesis example 11 (compound 11)> [ka]

[0191] [Synthesis of intermediate L11-5] 5.0 g (32.0 mmol) of 1-naphthaldehyde was dissolved in 60 ml of anisole, then Pd(PPh3)4 (2.6 g (2.24 mmol)), bis[2-(diphenylphosphino)phenyl] ether (DPEPhos) 1.7 g (3.2 mmol), K3PO4 (11 g (80 mmol)), 1,1,1-Trifluoro-2-iodoethane 10.6 ml (64 mmol) and 20 ml of water were added, and the mixture was heated at 130°C for 24 hours. After the reaction was complete, the mixture was neutralized with 1N-HCl, then ethyl acetate was added for extraction, and the organic layer was dried over magnesium sulfate. The reaction mixture obtained therefrom was distilled under reduced pressure and then purified by liquid chromatography to obtain intermediate L11-5 (3.9 g (52% yield)). LC-MS m / z=239(M+H) +

[0192] [Synthesis of intermediate L11-4] Except for using intermediate L11-5 instead of 4-bromo-1-naphthaldehyde, the same method as the synthesis of intermediate L9-5 in Synthesis Example 9 was used to obtain intermediate L11-4 (3.8g (yield 73%)). LC-MS m / z=326(M+H) +

[0193] [Synthesis of intermediate L11-3] Except for using intermediate L11-4 instead of intermediate L9-5, the same method as the synthesis of intermediate L9-4 in Synthesis Example 9 was used to obtain intermediate L11-3 (0.9g (yield 28%)). LC-MS m / z=262(M+H) +

[0194] [Synthesis of intermediate L11-2] Except for using intermediate L11-3 instead of intermediate L9-4, the same method as the synthesis of intermediate L9-3 in Synthesis Example 9 was used to obtain intermediate L11-2 (0.9g (yield 99%)).

[0195] [Synthesis of intermediate L11-1] Except for using intermediate L11-2 instead of intermediate L9-3, the same method as the synthesis of intermediate L9-3 in Synthesis Example 9 was used to obtain intermediate L11-1 (0.7g (yield 63%)). LC-MS m / z = 341(M+H) +

[0196] [Synthesis of intermediate L11] Except for using intermediate L11-1 instead of intermediate L1-1, the same method as the synthesis of intermediate L1 in Synthesis Example 1 was used to obtain intermediate L11 (0.6g (85% yield)). LC-MS m / z = 366(M+H) +

[0197] [Synthesis of the intermediate L11Dimer] Except for using intermediate L11 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L11Dimer.

[0198] [Synthesis of Compound 11] Except for using intermediate L11Dimer instead of intermediate L1Dimer, the same method as the synthesis of compound 1 in synthesis example 1 was used to obtain compound 11 (0.25 g (40% yield)). LC-MS m / z = 1135(M+H) +

[0199] <Synthesis example 12 (compound 12)> [ka]

[0200] [Synthesis of intermediate L12-1] Except for using iodine instead of chlorodimethylphenylsilane, the same method as the synthesis of intermediate L10 in Synthesis Example 10 was used to obtain intermediate L12-1 (1.4g (yield 50%)). LC-MS m / z=428(M+H) +

[0201] [Synthesis of intermediate L12] Intermediate L12-1 (1.2 g (2.8 mmol)) was mixed with 40 ml of tetrahydrofuran (THF) and 10 ml of water. 0.4 g (3.4 mmol) of phenylboronic acid, 0.2 g (0.2 mmol) of Pd(PPh3)4, and 1.0 g (7.0 mmol) of K2CO3 were added, and the mixture was heated under reflux at 85°C for 18 hours. After the reaction was complete, the reaction mixture was extracted with 30 ml of ethyl acetate, and the resulting organic layer was dried over magnesium sulfate, distilled under reduced pressure, and then purified by liquid chromatography to obtain intermediate L12 (0.8 g (78% yield)). LC-MS m / z = 378(M+H) +

[0202] [Synthesis of the intermediate L12Dimer] Except for using intermediate L12 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L12Dimer.

[0203] [Synthesis of Compound 12] Except for using intermediate L12Dimer instead of intermediate L1Dimer, the same method as the synthesis of compound 1 in Synthesis Example 1 was used to obtain compound 12 (0.3g (40% yield)). LC-MS m / z = 1159(M+H) +

[0204] <Synthesis example 13 (compound 13)> [ka]

[0205] [Synthesis of intermediate L13-4] 5.0 g (22.2 mmol) of 2-bromo-6-fluoronaphthalene was dissolved in 60 ml of anhydrous tetrahydrofuran (THF), and then 1.6 M BuLi solution (24.4 mmol) in 15 ml of hexane was gradually added at -78°C. After approximately 2 hours, 5.4 ml (26.6 mmol) of 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was gradually added dropwise, and the mixture was stirred at room temperature for 18 hours. After the reaction was complete, the organic layer obtained by extraction with 30 ml of ethyl acetate and water was dried over magnesium sulfate and distilled under reduced pressure. The intermediate L13-4 (5.1 g (85% yield)) was obtained by purification using liquid chromatography. LC-MS m / z = 273(M+H) +

[0206] [Synthesis of intermediate L13-3] Intermediate L13-4 (5.1 g (18.7 mmol)) was mixed with 120 ml of acetonitrile and 30 ml of water. PdCl2(PPh3)2 (0.9 g (1.3 mmol)), 2-chloro-4-iodonicotinaldehyde (5.0 g (18.7 mmol)), and K2CO3 (6.5 g (46.8 mmol)) were added, and the mixture was heated under reflux at 80°C for 24 hours. The resulting product was concentrated under reduced pressure, and the organic layer extracted by adding dichloromethane and water was dried over magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography to obtain intermediate L13-3 (4.4 g (82% yield)). LC-MS m / z = 286(M+H) +

[0207] [Synthesis of intermediate L13-2] 12.0 g (35.0 mmol) of (methoxymethyl)triphenylphosphonium chloride was mixed with 150 ml of anhydrous ether, and then 35 ml of 1.0 M potassium tert-butoxide solution was added dropwise. The mixture was stirred at room temperature for approximately 2 hours. Subsequently, intermediate L13-3 (4.0 g (14.0 mmol)), mixed with 60 ml of anhydrous tetrahydrofuran (THF), was gradually added dropwise, and the mixture was stirred at room temperature for 18 hours. The resulting product was then mixed with water and ethyl acetate to extract the organic layer. The resulting organic layer was dried over magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography to obtain intermediate L13-2 (4.2 g (95% yield)). LC-MS m / z = 314(M+H) +

[0208] [Synthesis of intermediate L13-1] Intermediate L13-2 (4.0 g (12.7 mmol)) was mixed with 250 ml of chloroform, and 5.6 ml (63.5 mmol) of trifluic acid was gradually added dropwise, followed by stirring at 60°C for approximately 4 hours. The resulting product was then extracted with saturated sodium bicarbonate aqueous solution, and the resulting organic layer was dried over magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography to obtain intermediate L13-1 (1.0 g (yield 28%)). LC-MS m / z=282(M+H) +

[0209] [Synthesis of intermediate L13] Except for using intermediate L13-1 instead of intermediate L1-1, the same method as the synthesis of intermediate L1 in Synthesis Example 1 was used to obtain intermediate L13 (1.0 g (82% yield)). LC-MS m / z=352(M+H) +

[0210] [Synthesis of the intermediate L13Dimer] Except for using intermediate L13 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L13Dimer.

[0211] [Synthesis of Compound 13] Except for using intermediate L13Dimer instead of intermediate L1Dimer, the same method as the synthesis of compound 1 in synthesis example 1 was used to obtain compound 13 (0.5g (yield 46%)). LC-MS m / z = 1107(M+H) +

[0212] <Synthesis example 14 (compound 14)> [ka]

[0213] [Synthesis of intermediate L14-5] 4.0 g (20.9 mmol) of 6-chloroisoquinoline-7-carbaldehyde was mixed with 80 ml of tetrahydrofuran (THF) and 20 ml of water. Then, Pd(PPh3)4 (1.6 g (1.4 mmol)), (3-fluoro-4-methylphenyl)boronic acid (25.1 mmol) and K2CO3 (7.2 g (52.3 mmol)) were added, and the mixture was heated under reflux for 18 hours. The resulting product was concentrated under reduced pressure, dissolved in dichloromethane, and the organic layer was extracted by adding water. After drying with magnesium sulfate, the product was distilled under reduced pressure and purified by liquid chromatography to obtain intermediate L14-5 (4.4 g (80% yield)). LC-MS m / z = 266(M+H) +

[0214] [Synthesis of intermediate L14-4] Except for using intermediate L14-5 instead of intermediate L1-3, the same method as the synthesis of intermediate L1-2 in Synthesis Example 1 was used to obtain intermediate L14-4 (4.4g (yield (95%))). LC-MS m / z=294(M+H) +

[0215] [Synthesis of intermediate L14-3] Except for using intermediate L14-4 instead of intermediate L13-2, the same method as the synthesis of intermediate L13-1 in Synthesis Example 13 was used to obtain intermediate L14-3 (1.9g (yield 52%)). LC-MS m / z=262(M+H) +

[0216] [Synthesis of intermediate L14-2] Except for using intermediate L14-3 instead of intermediate L9-4, the same method as the synthesis of intermediate L9-3 in Synthesis Example 9 was used to obtain intermediate L14-2 (0.9g (99% yield)).

[0217] [Synthesis of intermediate L14-1] Except for using intermediate L14-2 instead of intermediate L9-3, the same method as the synthesis method of intermediate L9-2 in Synthesis Example 9 was used to obtain intermediate L14-1 (1.3 g (yield 55%)). LC-MS m / z = 341 (M + H) +

[0218] [Synthesis of Intermediate L14] Except for using intermediate L14-1 instead of intermediate L1-1, the same method as the synthesis method of intermediate L1 in Synthesis Example 1 was used to obtain intermediate L14 (1.1 g (yield 80%)). LC-MS m / z = 366 (M + H) +

[0219] [Synthesis of Intermediate L14 Dimer] Except for using intermediate L14 instead of intermediate L1, the same method as the synthesis method of intermediate L1 Dimer in Synthesis Example 1 was used to obtain intermediate L14 Dimer.

[0220] [Synthesis of Compound 14] Except for using intermediate L14 Dimer instead of intermediate L1 Dimer, the same method as the synthesis method of Compound 1 in Synthesis Example 1 was used to obtain Compound 14 (0.6 g (yield 40%)). LC-MS m / z = 1135 (M + H) +

[0221] [Synthesis Example 15 (Compound 15)] [Chemical Formula]

[0222] [Synthesis of Intermediate L15-5] Except for using 4-bromonicotinaldehyde instead of 6-chloroisoquinoline-7-carbaldehyde, the same method as the synthesis method of intermediate L14-5 in Synthesis Example 14 was used to obtain intermediate L15-5 (2.8 g (yield 85%)). LC-MS m / z = 202 (M + H)+

[0223] [Synthesis of Intermediate L15-4] Except for using Intermediate L15-5 instead of Intermediate L1-3, the same method as the synthesis method of Intermediate L1-2 in Synthesis Example 1 was used to obtain Intermediate L15-4 (3.0 g, yield 95%). LC-MS m / z = 230 (M+H) +

[0224] [Synthesis of Intermediate L15-3] Except for using Intermediate L15-4 instead of Intermediate L13-2, the same method as the synthesis method of Intermediate L13-1 in Synthesis Example 13 was used to obtain Intermediate L15-3 (0.9 g, yield 35%). LC-MS m / z = 198 (M+H) +

[0225] [Synthesis of Intermediate L15-2] Except for using Intermediate L15-3 instead of Intermediate L9-4, the same method as the synthesis method of Intermediate L9-3 in Synthesis Example 9 was used to obtain Intermediate L15-2 (0.9 g, yield 99%).

[0226] [Synthesis of Intermediate L15-1] Except for using Intermediate L15-2 instead of Intermediate L9-3, the same method as the synthesis method of Intermediate L9-2 in Synthesis Example 9 was used to obtain Intermediate L15-1 (0.8 g, yield 70%). LC-MS m / z = 276 (M+H) +

[0227] [Synthesis of Intermediate L15] Except for using Intermediate L15-1 instead of Intermediate L1-1, the same method as the synthesis method of Intermediate L1 in Synthesis Example 1 was used to obtain Intermediate L15 (0.7 g, yield 85%). LC-MS m / z = 302 (M+H) +

[0228] [Synthesis of the intermediate L15Dimer] Except for using intermediate L15 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L15Dimer.

[0229] [Synthesis of Compound 15] Except for using intermediate L15Dimer instead of intermediate L1Dimer, the same method as the synthesis of compound 1 in synthesis example 1 was used to obtain compound 15 (0.2g (yield 40%)). LC-MS m / z = 10³⁵(M + H) +

[0230] <Synthesis example 16 (compound 16)> [ka]

[0231] [Synthesis of intermediate L16-3] Except for using (4-cyanophenyl)boronic acid instead of (4-(trofluoromethyl)phenyl)boronic acid, the same method as the synthesis of intermediate L5-3 in Synthesis Example 5 was used to obtain intermediate L16-3 (2.6g (yield 71%)). LC-MS m / z = 243(M+H) +

[0232] [Synthesis of intermediate L16-2] Except for using intermediate L16-3 instead of intermediate L5-3, the same method as the synthesis of intermediate L5-2 in Synthesis Example 5 was used to obtain intermediate L16-2 (2.7g (yield (95%))). LC-MS m / z=271(M+H) +

[0233] [Synthesis of intermediate L16-1] Except for using intermediate L16-2 instead of intermediate L5-2, the same method as the synthesis of intermediate L15-1 in Synthesis Example 5 was used to obtain intermediate L16-1 (0.6g (yield 25%)). LC-MS m / z=239(M+H) +

[0234] [Synthesis of intermediate L16] Except for using intermediate L16-1 instead of intermediate L1-1, the same method as the synthesis of intermediate L1 in Synthesis Example 1 was used to obtain intermediate L16 (0.6g (85% yield)). LC-MS m / z = 309(M+H) +

[0235] [Synthesis of the intermediate L16Dimer] Except for using intermediate L16 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L16Dimer.

[0236] [Synthesis of Compound 16] Except for using intermediate L16Dimer instead of intermediate L1Dimer, the same method as the synthesis of compound 1 in Synthesis Example 1 was used to obtain compound 16 (0.2g (40% yield)). LC-MS m / z = 1049(M+H) +

[0237] <Synthesis example 17 (compound 17)> [ka]

[0238] [Synthesis of intermediate L17] Except for using (4-(trifluoromethyl)naphthalene-2-hi)boronic acid instead of 3,5-dimethylphenylboronic acid, the same method as the synthesis of intermediate L2 in Synthesis Example 2 was used to obtain intermediate L17 (0.9 g (yield 72%)). LC-MS m / z=352(M+H) +

[0239] [Synthesis of intermediate L17Dimer] Except for using intermediate L17 instead of intermediate L2, the same method as the synthesis method for intermediate L2Dimer in Synthesis Example 2 was used to obtain intermediate L17Dimer.

[0240] [Synthesis of Compound 17] Except for using intermediate L17Dimer instead of intermediate L2Dimer, the same method as the synthesis of compound 2 in synthesis example 2 was used to obtain compound 17 (0.2g (yield 15%)). LC-MS m / z = 1105(M+H) +

[0241] <Synthesis example 18 (compound 18)> [ka]

[0242] [Synthesis of intermediate L18] Except for using (4-methylnaphthalene-2-yl)boronic acid instead of 3,5-dimethylphenylboronic acid, the same method as the synthesis of intermediate L3 in Synthesis Example 3 was used to obtain intermediate L18 (0.7g (80% yield)). LC-MS m / z = 410(M+H) +

[0243] [Synthesis of the intermediate L18 Dimer] Except for using intermediate L18 instead of intermediate L3, the same method as the synthesis method for intermediate L3Dimer in Synthesis Example 3 was used to obtain intermediate L18Dimer.

[0244] [Synthesis of Compound 18] Except for using the intermediate L18Dimer instead of the intermediate L3Dimer, the same method as the synthesis of compound 3 in Synthesis Example 3 was used to obtain compound 18 (0.1g (yield 15%)). LC-MS m / z=1221(M+H) +

[0245] <Synthesis example 19 (compound 19)> [ka]

[0246] [Synthesis of intermediate L19] Except for using (4-methylnaphthalene-2-yl)boronic acid instead of 3,5-dimethylphenylboronic acid, the same method as the synthesis of intermediate L1 in Synthesis Example 1 was used to obtain intermediate L19 (1.2 g (80% yield)). LC-MS m / z = 338(M+H) +

[0247] [Synthesis of the intermediate L19 Dimer] Except for using intermediate L19 instead of intermediate L1, the same method as the synthesis method for intermediate L1Dimer in Synthesis Example 1 was used to obtain intermediate L19Dimer.

[0248] [Synthesis of Compound 19] Except for using intermediate L19Dimer instead of intermediate L1Dimer, the same method as the synthesis of compound 1 in Synthesis Example 1 was used to obtain compound 19 (0.15 g (yield 16%)). LC-MS m / z = 1077(M+H) +

[0249] <<Example of evaluation 1>> The molecular structure of compound 1 was optimized using the B3LYP / LanL2DZ function for Ir contained in compound 1, and the B3LYP / 6-31G(D,P) function for the organic ligand contained in compound 1. Then, by performing DFT (density functional theory) calculations using Gaussian, two distances between Ir and N in compound 1 (D1(Ir-N) and D2(Ir-N)), and two distances between Ir and C (D1(Ir-C) and D2(Ir-C)) were evaluated, and from these, Δ(Ir-N) and Δ(Ir-C) of compound 1 were calculated. This process was repeated for compounds 2-19 and compounds A-C, and the results are summarized in Table 1 below. [Table 1] TIFF0007843595000099.tif67154TIFF0007843595000100.tif108154TIFF0007843595000101.tif32152TIFF0007843595000102.tif26152

[0250] From Table 1, we can confirm that the sum of Δ(Ir-N) and Δ(Ir-C) for compounds 1-19 is 0.002 Å or less, while the sum of Δ(Ir-N) and Δ(Ir-C) for compounds A-C exceeds 0.002 Å.

[0251] <<Example of evaluation 2>> The molecular structure of compound 1 was optimized using the B3LYP / LanL2DZ function for Ir contained in compound 1, and the B3LYP / 6-31G(D,P) function for the organic ligand contained in compound 1. Then, a DFT (density functional theory) calculation using Gaussian was performed to determine the L of compound 1. N and L C Evaluate and then L N / L C I calculated it. L of compound 1 N This is the maximum distance between a non-hydrogen atom in the group bonded to Ir via N and Ir, and is the L of compound 1. C This is the maximum distance between a non-hydrogen atom in a group bonded to Ir via C and Ir, and Ir. Figure 4 illustrates the groups in compound 1 that are linked to Ir via N and the groups that are linked to Ir via C. This process was repeated for compounds 1-19 and compounds A-C, and the results are summarized in Table 2 below. [Table 2]

[0252] From Table 2, the L of compounds 1-19 N / LC The L of compounds A and C is 1.45 or higher. N / L C It can be confirmed that it is less than 1.45.

[0253] <<Evaluation Example 3>> Compound H52 and compound 1 are placed on a quartz substrate in a weight ratio of 98:2, 10 -7 A 50nm thick film was fabricated by co-deposition under a Torr vacuum, and then a sealing glass plate was attached to the film to seal it. Using CoCoLink's Luxol-OLED / analyzer (LOA-100), the PL (luminescence intensity) was measured for the film from -150° to +150°. Then, the horizontal orientation ratio related to compound 1 was calculated using the analyzer's fitting program. This process was repeated for compounds 2-19 and compounds A-C, and the results are summarized in Table 3 below. [Table 3]

[0254] Table 3 confirms that the horizontal orientation ratio of compounds 1-19 is superior to that of compounds A-C.

[0255] The results of Evaluation Example 1 and Evaluation Example 2 are summarized in Table 4 below (○: Satisfied / ×: Unsatisfied). [Table 4]

[0256] <Example 1> As an anode, a glass substrate patterned with ITO was cut to a size of 50mm x 50mm x 0.5mm, ultrasonically cleaned with isopropyl alcohol and pure water for 5 minutes each, then exposed to ozone by ultraviolet light for 30 minutes for further cleaning, and finally placed in a vacuum deposition apparatus. HT3 and F6-TCNNQ were vacuum co-deposited on the upper part of the anode in a weight ratio of 98:2 to form a 100 Å thick hole injection layer, and HT3 was vacuum deposited on top of the hole injection layer to form a 1,350 Å thick hole transport layer. HT21 was vacuum deposited on top of the hole transport layer to form an electron blocking layer with a thickness of 300 Å. Next, H52 (host) and compound 1 (dopant) were co-deposited on the upper part of the electron blocking layer in a weight ratio of 98:2 to form a 400 Å thick luminescent layer. Subsequently, ET3 and ET-D1 were co-deposited on the upper part of the light-emitting layer in a 50:50 volume ratio to form a 350 Å thick electron transport layer, ET-D1 was vacuum-deposited on the upper part of the electron transport layer to form a 10 Å thick electron injection layer, and Al was vacuum-deposited on the upper part of the electron injection layer to form a 1,000 Å thick cathode, thereby fabricating an organic light-emitting device with the structure ITO(1,500 Å) / HT3+F6-TCNNQ(2 wt%)(100 Å) / HT3(1,350 Å) / HT21(300 Å) / H52+compound 1(2 wt%)(400 Å) / ET3+ET-D1(50%)(350 Å) / ET-D1(10 Å) / Al(1,000 Å). TIFF0007843595000106.tif109151

[0257] <Examples 2-19 and Comparative Examples A-C> An organic light-emitting device was fabricated using the same method as in Example 1, except that the compounds listed in Table 5 were used as dopants instead of compound 1 during the formation of the light-emitting layer.

[0258] <<Evaluation Example 4>> For each organic light-emitting element produced in Examples 1-19 and Comparative Examples A-C, the driving voltage (V), maximum external quantum efficiency (Max EQE) (%), FWQM (nm) of the EL spectrum, and lifetime (LT) are specified. 97 The (hr) was evaluated, and the results are shown in Table 5 below. As evaluation equipment, a current / voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used to determine the lifespan (LT). 97The values ​​(at 3,500 nits) represent the time (hr) required to reach 97% of the initial brightness compared to 100%. In Table 5, the drive voltage, maximum external quantum efficiency, and lifetime are expressed as relative values ​​(%). (Number 20) Roll-off ratio = {1 - (Efficiency (at 3,500 nits) / Maximum luminous efficiency)} × 100% [Table 5] TIFF0007843595000108.tif108154TIFF0007843595000109.tif32152TIFF0007843595000110.tif26152

[0259] Table 5 shows that the FWQM of light emitted from the organic light-emitting elements of Examples 1 to 19 is relatively smaller than that of the organic light-emitting elements of Comparative Examples A to C, confirming that the organic light-emitting elements of Examples 1 to 19 have higher color purity than those of Comparative Examples A to C. Furthermore, it can be confirmed that the organic light-emitting devices of Examples 1 to 19 have improved driving voltage, improved external quantum efficiency, and improved lifetime characteristics compared to the organic light-emitting devices of Comparative Examples A to C.

[0260] Furthermore, the present invention is not limited to the embodiments described above. It can be modified and implemented in various ways without departing from the technical scope of the present invention. [Explanation of symbols]

[0261] 10 Organic light-emitting devices 11 1st electrode 15 Organic layer 19 Second electrode

Claims

1. C ２ Having a symmetrical structure, It is represented by the chemical formula 1 shown below, An organometallic compound characterized in that the sum of Δ(Ir-N) and Δ(Ir-C) is 0.002 Å or less. (Chem.1) Ir(L) １ ) ２ (L) ２ Chemical Formula 1 (In the above chemical formula 1, L １ This is a ligand represented by the following chemical formula 2, L ２ This is a ligand represented by the following chemical formula 3, Two Ls １ One of them is the first L １ ligand, and the other one is the second L １ ligand, The first L １ Ligand and the 2L １ The ligands are identical to each other. 【Chemistry 2】 【Transformation 3】 In the aforementioned chemical formula 2, Y １ N is Y ２ C is, In the aforementioned chemical formula 2, 【change】 The group represented is one of the chemical formulas 2-1, 2-3, and 2-6 shown below. 【Chemistry 2-1(2-3)2-6】 In the aforementioned chemical formulas 2-1, 2-3, and 2-6, Y １ N is, X １ or X ８ C is, * represents the bonding site with Ir in chemical formula 1. * indicates CY ２ It is a combined site with, In the aforementioned chemical formula 2, 【change】 The group represented by is one of the chemical formulas CY2-1 and CY2-8 to CY2-10 shown below. 【Chemical CY2-1(CY2-8)-(CY2-10)】 In the aforementioned chemical formulas CY2-1 and CY2-8 to CY2-10, Y ２ C is, R ２１ ~R ２８ For explanations regarding each of these, see R below. ２ This is the same as the explanation given earlier. *' represents the bonding site with Ir in chemical formula 1. * represents the cyclic CY ring in chemical formula 1. １ It is a combined site with, In the aforementioned chemical formula 2, T １ teeth, A fluoro group (-F) or a cyano group, or Deuterium, fluoro group, cyano group, C １ -C ２０ alkyl group, C ３ -C １０ C fluoride substituted or unsubstituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof. １ -C ２０ Alkyl alkyl groups, C fluoride ３ -C １０ Cycloalkyl group, fluorinated phenyl group, fluorinated biphenyl group, cyano group-containing C １ -C ２０ C containing alkyl groups and cyano groups ３ -C １０ This is a cycloalkyl group, a cyano group-containing phenyl group, or a cyano group-containing biphenyl group. In the chemical formula 2, b1 is either 1 or 2, and when b1 is 2, two T １ They are either identical or different from one another. In the aforementioned chemical formulas 2 and 3, R １ , R ２ , and R ３３ They are independent of each other, Hydrogen, deuterium, -F, or cyano group, Deuterium, -F, cyano group, C １ -C ２０ alkyl group, C ３ -C １０ Cycloalkyl group, phenyl group, biphenyl group, -Si(Q ３３ ) (Q ３４ ) (Q ３５ ), or -Ge(Q ３３ ) (Q ３４ ) (Q ３５ ) or any combination thereof, C １ -C ２０ alkyl group, C ３ -C １０ Cycloalkyl groups, phenyl groups, or biphenyl groups or -Si(Q) ３ ) (Q ４ ) (Q ５ ), or -Ge(Q ３ ) (Q ４ ) (Q ５ ) and In the chemical formula 2, a1 is an integer from 0 to 10, and if a1 is 2 or more, then 2 or more R １ They are either identical or different from one another. In chemical formulas 2 and 3, * and *' are, respectively, the bonding sites with Ir in chemical formula 1. The aforementioned Δ(Ir-N) is represented by chemical formulas 1 and 2, and consists of Ir and the first L １ Ligand Y １ The distance to, Ir, and the aforementioned 2L １ Ligand Y １ It is the absolute value of the difference between the distance and the point. The aforementioned Δ(Ir-C) is represented by chemical formulas 1 and 2, where Ir and the first L １ Ligand Y ２ The distance to, Ir, and the aforementioned 2L １ Ligand Y ２ It is the absolute value of the difference between the distance and the point. The molecular structure of the organometallic compound represented by chemical formula 1 is optimized by using the B3LYP / LanL2DZ function for Ir contained in the organometallic compound represented by chemical formula 1, and the B3LYP / 6-31G(D,P) function for the organic ligand contained in the organometallic compound represented by chemical formula 1. Then, by performing DFT (density functional theory) calculations using Gaussian, the two distances between Ir and N in the organometallic compound represented by chemical formula 1 (D1(Ir-N) and D2(Ir-N)), and the two distances between Ir and C (D1(Ir-C) and D2(Ir-C)) are evaluated, and from there, Δ(Ir-N) and Δ(Ir-C) of the organometallic compound represented by chemical formula 1 are calculated. In chemical formula 3, R ３１ This is the group represented by chemical formula 4 below, and in chemical formula 3, R ３２ This is the group represented by the chemical formula 5 below, 【Chemistry 4】 【Transformation 5】 In the aforementioned chemical formulas 4 and 5, A １ ~A ６ They are independent of each other, Hydrogen or deuterium, or Deuterium, C １ -C ２０ C, which is substituted or unsubstituted with an alkyl group, or any combination thereof. １ -C ２０ It is an alkyl group, * is in chemical formula 3, R ３１ and R ３２ These are the bonding sites with the carbon atoms to which they are bonded. The aforementioned chemical formula 4 satisfies one of the following conditions 4-3 to 4-6: The aforementioned chemical formula 5 satisfies one of the following conditions 5-3 to 5-6: <Condition 4-3> A １ and A ２ These are, independently of each other, deuterium, C １ -C ２０ C, which is substituted or unsubstituted with an alkyl group, or any combination thereof. １ -C ２０ It is an alkyl group, A ３ Deuterium, C １ -C ２０ C, which is substituted or unsubstituted with an alkyl group, or any combination thereof. ２ -C ２０ It is an alkyl group, <Condition 4-4> A １ is, independently of each other, deuterium, C １ -C ２０ -alkyl group, or a C １ -C ２０ -alkyl group, which is substituted or unsubstituted with any combination thereof, A ２ and A ３ are, independently of each other, deuterium, C １ -C ２０ an alkyl group, or a C ２ -C ２０ alkyl group which is substituted or unsubstituted with any combination thereof <Condition 4-5> A １ It consists of hydrogen, deuterium, and -CH ３ ien-CH ２ D, -CHD ２ or CD ３ And, A ２ Deuterium, C １ -C ２０ C, which is substituted or unsubstituted with an alkyl group, or any combination thereof. １ -C ２０ It is an alkyl group, A ３ Deuterium, C １ -C ２０ C, which is substituted or unsubstituted with an alkyl group, or any combination thereof. ２ -C ２０ It is an alkyl group, <Condition 4-6> A １ It consists of hydrogen, deuterium, and -CH ３ , -CH2D, -CHD ２ or CD ３ And, A ２ and A ３ These are, independently of each other, deuterium, C １ -C ２０ C, which is substituted or unsubstituted with an alkyl group, or any combination thereof. ２ -C ２０ It is an alkyl group, <Condition 5-3> A ４ and A ５ These are, independently of each other, deuterium, C １ -C ２０ C, which is substituted or unsubstituted with an alkyl group, or any combination thereof. １ -C ２０ It is an alkyl group, A ６ Deuterium, C １ -C ２０ C, which is substituted or unsubstituted with an alkyl group, or any combination thereof. ２ -C ２０ It is an alkyl group, <Condition 5-4> A ４ These are, independently of each other, deuterium, C １ -C ２０ C, which is substituted or unsubstituted with an alkyl group, or any combination thereof. １ -C ２０ It is an alkyl group, A ５ and A ６ These are, independently of each other, deuterium, C １ -C ２０ C, which is substituted or unsubstituted with an alkyl group, or any combination thereof. ２ -C ２０ It is an alkyl group, <Condition 5-5> A ４ It consists of hydrogen, deuterium, and -CH ３ ien-CH ２ D, -CHD ２ or CD ３ And, A ５ Deuterium, C １ -C ２０ C, which is substituted or unsubstituted with an alkyl group, or any combination thereof. １ -C ２０ It is an alkyl group, A ６ Deuterium, C １ -C ２０ C, which is substituted or unsubstituted with an alkyl group, or any combination thereof. ２ -C ２０ It is an alkyl group. <Condition 5-6> A ４ It consists of hydrogen, deuterium, and -CH ３ ien-CH ２ D, -CHD ２ or CD ３ And, A ５ and A ６ These are, independently of each other, deuterium, C １ -C ２０ C, which is substituted or unsubstituted with an alkyl group, or any combination thereof. ２ -C ２０ It is an alkyl group, The above Q ３ ~Q ５ , and Q ３３ ~Q ３５ They are independent of each other, Deuterium, C １ -C ６０ alkyl group, C ６ -C ６０ A carbon atom substituted or unsubstituted with an aryl group, or any combination thereof. １ -C ６０ Alkyl alkyl group, or Deuterium, C １ -C ６０ alkyl group, C ６ -C ６０ A carbon atom substituted or unsubstituted with an aryl group, or any combination thereof. ６ -C ６０ It is an aryl group, However, the organometallic compounds mentioned above are not compounds 1-25, 27-31, or 34-39 listed below. 【Chemistry 1-18】 [Chemistry 19-31] [Chemistry 34-39]

2. In the aforementioned chemical formula 2, 【change】 The organometallic compound according to claim 1, characterized in that the group represented is one of the chemical formulas 2(1) to 2(48) shown below. 【Chemistry 2(1)-2(12)】 【Chemistry 2(13)-2(24)】 【Chemistry 2(25)-2(36)】 【Chemistry 2(37)-2(48)】 (In the above chemical formulas 2(1) to 2(48), Y １ N is, X １１ C(R) １１ ) and X １２ C(R) １２ ) and X １３ C(R) １３ ) and X １４ C(R) １４ ) and X １５ C(R) １５ ) and X １６ C(R) １６ ) and X １７ C(R) １７ ) and X １８ C(R) １８ ) and The aforementioned R １１ ~R １８ The explanations regarding each of these are as follows in claim 1, R １ This is the same as the explanation regarding, T １１ and T １２ The explanations regarding this are as follows in each claim 1: １ This is the same as the explanation regarding, * represents the bonding site with Ir in chemical formula 1. * indicates CY ２ This is a junction site with [another site].

3. In the aforementioned chemical formula CY2-1, R ２１ and R ２３ These are, independently of each other, deuterium, C １ -C ２０ alkyl group, C ３ -C １０ C １ -C ２０ alkyl group, C ３ -C １０ The organometallic compound according to claim 1, characterized in that it is a cycloalkyl group, a phenyl group, or a biphenyl group.

4. First electrode and The second electrode and Displaced between the first electrode and the second electrode, and comprising an organic layer including a light-emitting layer, The organic light-emitting element is characterized in that the organic layer contains one or more organometallic compounds as described in any one of claims 1 to 3.

5. The first electrode is an anode, The second electrode is a cathode, 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. The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof. The organic light-emitting element according to claim 4, characterized in that the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

6. The organic light-emitting element according to claim 4, characterized in that the organometallic compound is included in the light-emitting layer.

7. An electronic device characterized by including an organic light-emitting element according to any one of claims 4 to 6.

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