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

Abstract

To provide an organometallic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.SOLUTION: The organometallic compound has a charge capture ability (CCA) of about 4.0 to about 10.5, and includes a transition metal and n ligands linked to the transition metal, where n is an integer from 1 to 6, and where the n ligands include at least one ligand linked to the transition metal through carbon, nitrogen or a combination thereof and do not include any ligand linked to the transition metal through two oxygen atoms.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to organometallic compounds, organic light-emitting devices containing the same, and electronic devices including organic light-emitting devices. [Background technology]

[0002] Organic light-emitting devices are self-emitting elements that excel in viewing angle, response time, brightness, driving voltage, and response speed, and can be made multi-colored.

[0003] For example, an organic light-emitting device includes an anode, a cathode, and an organic layer containing a light-emitting layer, 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. The holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated as the excitons change from the excited state to the ground state. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2017-39713 [Overview of the project] [Problems that the invention aims to solve]

[0005] The present invention has been made in view of the above-mentioned prior art, and the object of the present invention is to provide a novel organometallic compound, an organic light-emitting element employing the same, and an electronic device including an organic light-emitting element. [Means for solving the problem]

[0006] To achieve the above objective, an organometallic compound according to one aspect of the present invention is: It has a charge capture ability (CCA) of 4.0 to 10.5. The aforementioned charge trapping ability (CCA) is expressed by the following <Equation 1>, The material comprises a transition metal and n ligands bonded to the transition metal, The aforementioned n is an integer between 1 and 6. The n ligands include at least one ligand bonded to the transition metal via carbon, nitrogen, or a combination thereof. The n ligands do not include ligands bonded to the transition metal via two oxygen atoms. [Mathematics 1] Charge capture ability (CCA)=5×10 -9 ×DM×PD In the above <Equation 1>, DM is the dipole moment of the organometallic compound, evaluated by density functional theory (DFT) calculations based on Hartree atomic units. PD is the polarization determinant of the organometallic compound, evaluated by density functional theory (DFT) calculations based on Hartree atomic units.

[0007] In other aspects, an organic light-emitting device is provided, comprising a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer contains one or more organometallic compounds.

[0008] The aforementioned organometallic compound is contained in the light-emitting layer, and the organometallic compound contained in the light-emitting layer acts as a dopant.

[0009] In another aspect, an electronic device including the organic light-emitting element is provided. [Effects of the Invention]

[0010] According to the present invention, by using organometallic compounds as dopants in the light-emitting layer of an organic light-emitting device, it is possible to realize an organic light-emitting device with a long lifespan even with relatively low doping concentrations. Therefore, by utilizing organometallic compounds, it is possible to mass-produce organic light-emitting devices with a long lifespan at low cost. [Brief explanation of the drawing]

[0011] [Figure 1] This is a schematic cross-sectional view showing an example of an organic light-emitting element. [Figure 2] The figures in Tables 2 and 3 are contour plots showing the data, with the x-axis representing charge trapping ability (CCA), the y-axis representing dopant content (mol%) per 100 mol% of the light-emitting layer, and the z-axis showing the relative lifetime (%) of an organic light-emitting device having a light-emitting layer containing a dopant with charge trapping ability (CCA) as represented by the y-axis content (mol%). [Modes for carrying out the invention]

[0012] Organometallic compounds have a charge capture ability (CCA) of 4.0 to 10.5.

[0013] For example, organometallic compounds have a charge trapping ability (CCA) of 4.30 to 10.25.

[0014] Charge trapping ability (CCA) represents the charge trapping properties of organometallic compounds and is expressed by the following <Equation 1>.

[0015] [Mathematics 1] Charge capture ability (CCA)=5×10 -9 ×DM×PD

[0016] In the above formula 1, DM is the dipole moment of an organometallic compound, evaluated by density functional theory (DFT) calculations based on Hartree atomic units. PD is the polarization determinant of organometallic compounds, evaluated by density functional theory (DFT) calculations based on Hartree atomic units.

[0017] On the other hand, the constant "5 × 10" introduced in the above <Equation 1> -9 This constant is arbitrarily introduced to adjust the magnitude of the charge trapping ability (CCA).

[0018] The Hartree atomic unit, also known as the atomic unit system (au or au), is a widely known system of natural units of measurement in the fields of atomic physics and computational chemistry calculations. The Hartree atomic unit is distinct from the Rydberg atomic unit and atomic mass unit, and is a system of units focused on electronic properties. For this reason, in the Hartree atomic unit, four fundamental physical constants—1) electron mass, 2) elementary charge, 3) reduced Planck constant, and 4) inverse Coulomb constant—are all defined as "1". The DM and PM in <Equation 1> calculated based on such Hartree atomic units do not have a unit of measurement like Debye, which is readily apparent to those skilled in the art.

[0019] Density functional calculations are performed using a variety of quantum mechanical calculation programs. For example, quantum mechanical calculation programs include Gaussian, Games, Psi4, etc.

[0020] According to one embodiment, the density functional calculation is performed using a Gaussian program, for example, the Gaussian09 program.

[0021] According to another embodiment, when using the Gaussian program, for the metals contained in the DM and PM measurement target compounds, the B3LYP / LanL2DZ function is used, and for the organic ligands contained in the DM and PM measurement target compounds, the B3LYP / 6-31G(D,P) function is used to optimize the molecular structure of the DM and PM measurement target compounds.

[0022] According to yet another embodiment, the DM calculation process of the above <Equation 1> using the Gaussian program includes: 1) calculating the dipole moment in Debye units shown by "Dipole moment (field-independent basis, Debye): X, Y, Z, Tot", and 2) applying the formula "1 Debye = 0.3934 a.u." to the Debye unit dipole moment value to convert it to the DM of the above <Equation 1> based on Hartree atomic units.

[0023] According to yet another embodiment, the PM calculation process of the above <Equation 1> using the Gaussian program includes: 1) calculating the polarizability shown by "Exact polarizability: α xx , α xy , α yy , α xz , α yz , α zz ", and 2) calculating the polarizability determinant (PD) according to the following <Equation 1A> for the polarizability and converting it to the PM of the above <Equation 1> based on Hartree atomic units.

[0024]

Number

[0025] Although not limited by any particular theory, organometallic compounds contained in the emission layer of an organic light-emitting device have the property of capturing charges (holes and / or electrons) injected from a pair of electrodes.

[0026] If the amount of charge trapping by organometallic compounds in the light-emitting layer is excessive, charge transfer within the light-emitting layer becomes less smooth, and excessively localized hole and electron recombination zones are formed. As a result, the concentration of excitons in the recombination zones becomes excessively high, increasing triplet-triplet annihilation and / or triplet-polaron quenching, which reduces the lifetime of the organic light-emitting device.

[0027] On the other hand, if the amount of charge trapping by the organometallic compound contained in the light-emitting layer is excessively small, the recombination region will be excessively large due to the active movement of charge in the light-emitting layer, and unrecombined charges will accumulate at both interfaces of the light-emitting layer, resulting in a reduced lifespan for the organic light-emitting device.

[0028] As a result, the inventors have demonstrated that by controlling the amount of charge trapping by the organometallic compound, the lifespan of an organic light-emitting device employing an organometallic compound can be dramatically improved, and that the control of the amount of charge trapping by the organometallic compound with respect to the lifespan of the organic light-emitting device can be achieved by controlling the dipole moment (i.e., DM in <Equation 1> above) and the polarization determinant (i.e., PM in <Equation 1> above) of the organometallic compound.

[0029] Specifically, the dipole moment of an organometallic compound is a parameter related to its charge capture radius, and the polarization determinant of an organometallic compound is a parameter related to the induced dipole moment generated by the electric field when an organic light-emitting device is driven. By considering both the dipole moment and the polarization determinant, the charge capture characteristics of the organometallic compound can be effectively controlled.

[0030] Organometallic compounds emit green light.

[0031] According to one example, organometallic compounds emit light with a maximum emission wavelength of 490 nm to 550 nm.

[0032] For example, the maximum emission wavelength of the PL and / or EL spectra of organometallic compounds is 490 nm to 550 nm.

[0033] On the other hand, organometallic compounds contain a transition metal and n ligands bonded to the transition metal.

[0034] For example, transition metals are 1-period transition metals, 2-period transition metals, or 3-period transition metals.

[0035] Other examples of transition metals include iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), or rhenium (Re).

[0036] According to one example, organometallic compounds contain one transition metal.

[0037] n is an integer between 1 and 6. For example, n is either 2 or 3.

[0038] Each of the n ligands includes at least one ligand bonded to the transition metal via carbon, nitrogen, or a combination thereof, but does not include any ligands bonded to the transition metal via two oxygen atoms (e.g., a bidentate ligand bonded to the transition metal via two oxygen atoms).

[0039] According to one example, in organometallic compounds, The transition metals are iridium, osmium, rhodium, or rhenium. n is 3, Each of the n ligands is a bidentate ligand bonded to a transition metal via carbon, nitrogen, or a combination thereof.

[0040] According to other examples, organometallic compounds are represented by the following chemical formulas 1 or 2. [Cation 1] M1(L1) n1 (L2) n2 [Cation 2] M2(L1)(L 11 )

[0041] In the above chemical formula 1, M1 is iridium, osmium, rhodium, or rhenium.

[0042] In the above chemical formula 1, n1 and n2 are independently 1 or 2, but n1 + n2 is 3.

[0043] In the above chemical formula 2, M2 is platinum, palladium, or gold.

[0044] In the above chemical formulas 1 and 2, L1 and L2 are bidentate ligands bonded to a transition metal via carbon, nitrogen, or a combination thereof, and in the above chemical formula 2, L 11 is any bidentate ligand.

[0045] In the above chemical formula 1, i) L1 and L2 are identical, or ii) L1 and L2 are different.

[0046] In the above chemical formula 1, i) when n1 is 2, the two L1 atoms are identical; ii) when n1 is 2, the two L1 atoms are different; iii) when n2 is 2, the two L2 atoms are identical; or iv) when n2 is 2, the two L2 atoms are different.

[0047] In the above chemical formula 2, i) L1 and L 11 ii) L1 and L 11 These are different from each other.

[0048] Of the n1 L1 and n2 L2 in the above chemical formula 1, two or more are selectively linked to each other via a first linking group, forming a tetradentate ligand or a hexadentate ligand, and L1 and L2 in the above chemical formula 2 11 These molecules are selectively linked to each other via the first linking group, forming a tetradentate ligand. For an explanation of the first linking group, refer to the explanation of T1 in Chemical Formula 3-1, which will be discussed later.

[0049] According to one example, the organometallic compound is represented by the above chemical formula 1, and in the above chemical formula 1, L1 and L2 are different from each other.

[0050] In other concrete examples, in the above chemical formulas 1 and 2, L1 is the ligand represented by the following chemical formula 3-1, and in the above chemical formula 1, L2 is the ligand represented by the following chemical formula 3-2.

[0051] [ka] [ka]

[0052] In the above chemical formulas 3-1 and 3-2, * and *' are, respectively, the bonding sites with M1 in chemical formula 1 or the bonding sites with M2 in chemical formula 2.

[0053] In the chemical formulas 3-1 and 3-2 above, Y1 to Y4 are each independently either N or C.

[0054] For example, in the chemical formulas 3-1 and 3-2 above, Y1 and Y3 are N, and Y2 and Y4 are C.

[0055] The bond between M1 in Chemical Formula 1 and M2 in Chemical Formula 2 and Y1 in Chemical Formula 3-1 is a coordinate bond; the bond between M1 in Chemical Formula 1 and M2 in Chemical Formula 2 and Y2 in Chemical Formula 3-1 is a covalent bond; the bond between M1 in Chemical Formula 1 and Y3 in Chemical Formula 3-2 is a coordinate bond; and the bond between M1 in Chemical Formula 1 and Y4 in Chemical Formula 3-2 is a covalent bond. Therefore, the organometallic compound represented by Chemical Formula 1 is electrically neutral.

[0056] In the above chemical formulas 3-1 and 3-2, rings CY1 to CY4 are each independently C5-C 30 Carbon ring group or C2-C 30 It is a heterocyclic group.

[0057] For example, in the above chemical formulas 3-1 and 3-2, each of the rings CY1 to CY4 is independently i) a primary ring, ii) a secondary ring, iii) a condensed ring formed by the fusion of two or more primary rings, iv) a condensed ring formed by the fusion of two or more secondary rings, or v) a condensed ring formed by the fusion of one or more primary rings and one or more secondary rings. The first ring is a cyclopentane group, cyclopentadiene group, furan group, thiophene group, pyrrole group, silole group, germol group, borol 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, azaboro-l group, or azaphosphorol group. The second ring is 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.

[0058] According to one example, in the above chemical formulas 3-1 and 3-2, rings CY1 to CY4 are independently a cyclopentene group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzobolol group, a benzophosphole group, an indene group, a benzosilol group, a benzogermol group, a benzothiophene group, and a benzoselenophene group. Azaindole group, benzofuran group, carbazole group, dibenzobolol group, dibenzophosphole group, fluorene group, dibenzosilol group, dibenzogermol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzobolol group, azabenzophosphole group, azaindene group, azabenzosilol group, azabenzogermol group, azabenzothiophene group, azabenzoselenophene Azadibenzofuran group, azacarbazole group, azadibenzobolol group, azadibenzophosphorus 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, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, ki The group is a nazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, 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.

[0059] According to another embodiment, in Chemical Formulas 3-1 and 3-2, Y1 and Y3 are N, and ring CY1 and ring CY3 are each, independently of the other, a group represented by one of the following Chemical Formulas CYN-1 to CYN-52. In Chemical Formulas 3-1 and 3-2, Y2 and Y4 are C, and ring CY2 and ring CY4 are each, independently of the other, a group represented by one of the following Chemical Formulas CYC-1 to CYC-65.

[0060] [Chemical Formula]

[0061] [Chemical Formula] [Chemical Formula]

[0062] In Chemical Formulas CYN-1 to CYN-52, X1 is O, S, N, C, or Si, *’ is a bonding site with M1 of Chemical Formula 1 or M2 of Chemical Formula 2, and *” is a bonding site with T1 or T3 of Chemical Formulas 3-1 and 3-2. In Chemical Formulas CYC-1 to CYC-65, X2 is O, S, N, C, or Si, * is a bonding site with M1 of Chemical Formula 1 or M2 of Chemical Formula 2, and *” is a bonding site with T1 or T3 of Chemical Formulas 3-1 and 3-2. [[ID=--]]At least one of N, C, and Si which are ring-forming atoms of Chemical Formulas CYN-1 to CYN-52 and CYC-1 to CYC-65 may be selectively bonded to a group represented by -(A1) b1 -R1, a group represented by -(A2) b2 -R2, a group represented by -(A3) b3 -R3, and / or a group represented by -(A4) b4 -R4. This can be recognized by those skilled in the art by referring to Chemical Formulas 3-1 and 3-2.

[0063] According to still another embodiment, In the above chemical formula 3-1, ring CY1 is a pyridine group or a pyrimidine group, and / or In the above chemical formula 3-1, the ring CY2 is a benzene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzosilole group, and / or In the above chemical formula 3-2, the ring CY3 is a benzimidazole group, a pyridoimidazole group, a pyridine group, or a pyrimidine group, and / or In the above chemical formula 3-2, the ring CY4 is a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, azadibenzofuran group, azadibenzothiophene group, azacarbazole group, azafluorene group, or azadibenzosilole group.

[0064] In the chemical formulas 3-1 and 3-2 above, T1 and T3 are, independently of each other, a single bond, a double bond, *-N(R7)-*', *-B(R7)-*', *-P(R7)-*', *-C(R7)(R8)-*', *-Si(R7)(R8)-*', *-Ge(R7)(R8)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R7)=*', *=C(R7)-*', *-C(R7)=C(R8)-*', *-C(=S)-*', or *-C≡C-*'. Here, * and *' are bonding sites with adjacent atoms, respectively.

[0065] For example, in the chemical formulas 3-1 and 3-2 above, T1 and T3 are single bonds, respectively.

[0066] In chemical formulas 3-1 and 3-2, A1 to A4 each independently have a single bond, at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substituted or unsubstituted C2-C 30 It is a heterocyclic group.

[0067] For example, in the above chemical formulas 3-1 and 3-2, A1 to A4 are each independent of each other. Single bond; or At least one R 10a Substituted or unsubstituted cyclopentene group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, cyclopentadiene group, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, indole group, benzobolol group, benzophosphole group, indene group, benzosilol group, benzogermol group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzobolol Azaindole group, dibenzophosphole group, fluorene group, dibenzosilol group, dibenzogermol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzobolol group, azabenzophosphole group, azaindene group, azabenzosilol group, azabenzogermol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azaca Luvazole group, azadibenzobolol 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, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phena The group is a thiazole group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, 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.

[0068] In the chemical formulas 3-1 and 3-2 above, b1 to b4 represent the number of A1 to A4, respectively, and each is an integer from 1 to 10 (for example, 1, 2, or 3). If b1 is 2 or more, then 2 or more A1s are either identical or different from each other; if b2 is 2 or more, then 2 or more A2s are either identical or different from each other; if b3 is 2 or more, then 2 or more A3s are either identical or different from each other; and if b4 is 2 or more, then 2 or more A4s are either identical or different from each other.

[0069] In the above chemical formulas 3-1 and 3-2, R1 to R4, R7 and R8 are, independently, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or 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 60These are heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9). For explanations of Q1 to Q9, please refer to the respective sections described herein.

[0070] For example, R1 through R4, R7, and R8 are each 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 10 Alkyl 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 20Alkyl) 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 20 Alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 C1-C substituted with alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl 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 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-C20 Alkyl)cyclohexenyl group, (C1-C 20 Alkyl)cycloheptenyl group, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 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, pyrazinyl 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, benzo Xasazolyl 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, 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, phenyl group, (C1-C 20Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl 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, benzoquinolinyl group, quinoki Salinyl 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; or -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9); Q1 through Q9 are each 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 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 alkyl groups, phenyl groups, or any combination thereof;

[0071] As yet another example, in Chemical Formulas 3-1 and 3-2, R1 to R4, R7, and R8 are each independently hydrogen, deuterium, -F, a cyano group, a nitro group, -SF5, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by one of Chemical Formulas 9-1 to 9-39, a group in which at least one hydrogen of one of Chemical Formulas 9-1 to 9-39 is substituted with deuterium, a group represented by one of Chemical Formulas 9-201 to 9-237, a group in which at least one hydrogen of one of Chemical Formulas 9-201 to 9-237 is substituted with deuterium, a group represented by one of Chemical Formulas 10-1 to 10-129, a group in which at least one hydrogen of one of Chemical Formulas 10-1 to 10-129 is substituted with deuterium, a group represented by one of Chemical Formulas 10-201 to 10-350, a group in which at least one hydrogen of one of Chemical Formulas 10-201 to 10-350 is substituted with deuterium, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5) (however, for the descriptions of Q3 to Q5, refer to the locations described in this specification respectively).

[0072]

Chemical formula

[0073]

Chemical formula

[0074]

Chemical formula

Chemical formula

Chemical formula

[0075]

Chemical formula

Chemical formula

[0076] In the above chemical formulas 9-1 to 9-39, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, * represents a bonding site with an adjacent atom, Ph represents a phenyl group, TMS represents a trimethylsilyl group, and TMG represents a trimethylgermyl group.

[0077] The above-mentioned "groups in which at least one hydrogen atom from chemical formulas 9-1 to 9-39 is substituted with deuterium" and "groups in which at least one hydrogen atom from chemical formulas 9-201 to 9-237 is substituted with deuterium" are, for example, the groups represented by the following chemical formulas 9-501 to 9-514 and 9-601 to 9-636.

[0078] [ka]

[0079] [ka]

[0080] The above-mentioned "groups in which at least one hydrogen atom from chemical formulas 10-1 to 10-129 is substituted with deuterium" and "groups in which at least one hydrogen atom from chemical formulas 10-201 to 10-350 is substituted with deuterium" are, for example, the groups represented by the following chemical formulas 10-501 to 10-553.

[0081] [ka] [ka]

[0082] In the above chemical formulas 3-1 and 3-2, a1 to a4 are *-(A1) b1 -The base represented by R1, *-(A2) b2 -The base represented by R2, *-(A3) b3 -The base represented by R3, and *-(A4) b4 -R4 represents the number of elements, each independently an integer between 0 and 20 (for example, an integer between 0 and 8). If a1 is 2 or greater, then *-(A1) is 2 or greater. b1 -The groups represented by R1 are either identical or different, and if a2 is 2 or more, then 2 or more *-(A2) b2 -The groups represented by R2 are either identical or different from each other, and if a3 is 2 or more, then 2 or more *-(A3) b3 -The bases represented by R3 are either identical or different to each other, and if a4 is 2 or more, then 2 or more *-(A4) b4 The groups represented by -R4 are either identical or different from each other.

[0083] For example, in the chemical formula 3-2 above, R4 is not hydrogen, and a4 is an integer from 1 to 6.

[0084] According to one example, the organometallic compound is represented by the above chemical formula 1, and the above chemical formula 1 includes a group represented by -Si(Q3)(Q4)(Q5), a group represented by -Ge(Q3)(Q4)(Q5), or any combination thereof.

[0085] According to other examples, at least one of the R1 groups a in the above chemical formula 3-1 is a group represented by -Si(Q3)(Q4)(Q5) or a group represented by -Ge(Q3)(Q4)(Q5).

[0086] Furthermore, according to other concrete examples, in the above chemical formula 3-1, [ka] The group represented by is a group represented by one of the following chemical formulas CY1(1) to CY1(25).

[0087]

Chem.

[0088] In the above chemical formulas CY1(1) to CY1(25), Y1 is N, R 11 to R 18 For the descriptions of , refer to the descriptions of R1 in this specification respectively. However, in the above chemical formulas CY1(2) to CY1(16), R 11 to R 14 are not hydrogen respectively, *’ is the bonding site with M1 in the above chemical formula 1 or M2 in the above chemical formula 2, *” is the bonding site with T1 in the above chemical formula 3-1.

[0089] According to another embodiment, in the above chemical formula 3-1,

Chem.

[0090]

Chem.

[0091] In the above chemical formulas CY1-1 to CY1-4, Y1 is N, X 12 is Si or Ge, R 11 to R 18 For the descriptions of , refer to the descriptions of R1 in this specification respectively, For the descriptions of Q3 to Q5, refer to the places described in this specification respectively, *’ is a binding site with M1 of the above chemical formula 1 or M2 of the above chemical formula 2, *” is a binding site with T1 of the above chemical formula 3-1.

[0092] According to another embodiment, a1 R1s of the above chemical formula 3-1 (for example, in the above chemical formulas CY1-1 to CY1-4, R 11 to R 18 being) are each independently hydrogen, deuterium, C1-C 20 alkyl group, deuterated C1-C 20 alkyl group, C3-C 10 cycloalkyl group, or deuterated C3-C 10 cycloalkyl group.

[0093] According to another embodiment, a1 R1s of the above chemical formula 3-1 (for example, in the above chemical formulas CY1-1 to CY1-4, R 11 to R 18 being) are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, substituted or unsubstituted C1-C 60 alkyl group, or substituted or unsubstituted C3-C 10 cycloalkyl group.

[0094] According to another embodiment, a1 R1s of the above chemical formula 3-1 (for example, in the above chemical formulas CY1-1 to CY1-4, R 11 to R 18 being) are each independently hydrogen, deuterium, -F, or cyano group; deuterium, -F, cyano group, C3-C 10 cycloalkyl group, (C1-C 20 alkyl)C3-C 10 cycloalkyl group, or substituted or unsubstituted C1-C 20 alkyl group with any combination thereof; or deuterium, -F, cyano group, C1-C 20 alkyl group, or substituted or unsubstituted C3-C 10 cycloalkyl group with any combination thereof; and is.

[0095] Furthermore, according to other concrete examples, one R1 in the above chemical formula 3-1 (for example, in the above chemical formulas CY1-1 to CY1-4, R 11 ~R 18 These are, each independently, Hydrogen, deuterium, -F, or cyano group; Deuterium, -F, cyano group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group (bicyclo[2.2.1]heptyl group), norbornenyl 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)bicyclo[1.1.1]pentyl group, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 A C1-C group substituted or unsubstituted with an alkyl)bicyclo[2.2.2]octyl group, or any combination thereof. 20 alkyl group; or Deuterium, -F, cyano group, C1-C 20 The groups are alkyl groups, or any combination thereof, substituted or unsubstituted cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, adamantanyl groups, norbornanyl groups, norborneyl groups, bicyclo[1.1.1]pentyl groups, bicyclo[2.1.1]hexyl groups, or bicyclo[2.2.2]octyl groups.

[0096] Furthermore, according to other concrete examples, in the above chemical formula CY1-1, R 11 It is not hydrogen.

[0097] Furthermore, according to other concrete examples, in the above chemical formula CY1-1, R 11 These are not hydrogen or methyl groups.

[0098] Furthermore, according to other concrete examples, in the above chemical formula CY1-1, R 11 These are not hydrogen, methyl groups, or cyano groups.

[0099] Furthermore, according to other concrete examples, in the above chemical formula CY1-1, R 11 It is not hydrogen, but R 12 and R 13 It is hydrogen.

[0100] Furthermore, according to other concrete examples, in the above chemical formula CY1-1, R 11 This is a group containing four or more carbon atoms.

[0101] Furthermore, according to other concrete examples, in the above chemical formula CY1-1, R 11 teeth, Deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, phenyl groups, (C1-C 20 Methyl groups substituted with alkyl)phenyl groups, naphthyl groups, pyridinyl groups, furanyl groups, thiophenyl groups, benzofuranyl groups, benzothiophenyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, or any combination thereof; or Deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, phenyl groups, (C1-C 20C2-C 20 Alkyl, C3-C 10 These are cycloalkyl groups, phenyl groups, naphthyl groups, pyridinyl groups, furanyl groups, thiophenyl groups, benzofuranyl groups, benzothiophenyl groups, dibenzofuranyl groups, or dibenzothiophenyl groups.

[0102] Furthermore, according to other examples, in this specification, Q1 to Q9 (for example, Q3 to Q5 in the above chemical formula CY1-1) are each independently deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 10 C1-C 60 Alkyl alkyl group or C6-C 60 It is an aryl group.

[0103] Furthermore, according to other examples, in this specification, Q1 to Q9 (for example, Q3 to Q5 in the above chemical formula CY1-1) are each independently deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 10The alkyl groups, or any combination thereof, may be substituted or unsubstituted, and include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, phenyl, biphenyl, or naphthyl groups.

[0104] In further examples, in this specification, Q1 to Q9 (for example, Q3 to Q5 in the above chemical formula CY1-1) are each independently -CH3, -CH2CH3, -CD3, -CD2H, -CDH2, -CH2CD3, or -CD2CH3.

[0105] Furthermore, other concrete examples show that in the above chemical formula CY1-1, Q3 to Q5 are either identical or different from each other.

[0106] Furthermore, according to other concrete examples, in the above chemical formula 3-1, [ka] The group represented by is one of the following chemical formulas CY2(1) to CY2(67).

[0107] [ka] [ka] [ka]

[0108] The above chemical formulas CY2(1) to CY2(67) Y2 is C, X 21 O, S, N(R) 27 ), C(R 27 )(R 28 ), or Si(R 27 )(R 28 ) and R 21 ~R 28 The explanations regarding R2 are as described herein, but refer to the explanations regarding R2, for the above chemical formulas CY2(2) to CY2(16), CY2(27) to CY2(32), CY2(34) to CY2(39), CY2(41) to CY2(46), CY2(48) to CY2(53), CY2(55) to CY2(60), and CY2(62) to CY2(67), 21 ~R 26 These are not hydrogen, * represents the bonding site with M1 in the above chemical formula 1, or M2 in the above chemical formula 2. * indicates the bonding site with T1 in the chemical formula 3-1 above.

[0109] Furthermore, according to other concrete examples, in the above chemical formula 3-2, [ka] The group represented by is one of the following chemical formulas CY3(1) to CY3(37).

[0110] [ka] [ka]

[0111] The above chemical formulas CY3(1) to CY3(37) Y3 is N, A 35 For further explanation, please refer to the explanation for A3 in this specification. R 31 ~R 35 For explanations regarding R3, please refer to the explanations regarding R3 in this specification, however, 31 ~R 35 These are not hydrogen, *' represents the bonding site with M1 in the above chemical formula 1. * represents the bonding site with T3 in the chemical formula 3-2 above.

[0112] For example, with the above chemical formulas CY3(17) to CY3(37), A 35 teeth, Single bond; or Deuterium, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl group, phenyl group, (C1-C 20 Alkyl)phenyl group, naphthyl group, (C1-C 20 Alkyl)naphthyl group, phenantrenyl group, (C1-C 20 A benzene group, naphthalene group, phenanthrene group, dibenzofuran group, or dibenzothiophene group, substituted or unsubstituted with an alkyl)phenanthrenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof; R 35 teeth, Hydrogen, deuterium, or C1-C 20 alkyl group; or Deuterium, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl group, phenyl group, (C1-C 20 Alkyl)phenyl group, naphthyl group, (C1-C 20 Alkyl)naphthyl group, phenantrenyl group, (C1-C 20 A phenyl group, naphthyl group, phenantrenyl group, dibenzofuranyl group, or dibenzothiophenyl group, substituted or unsubstituted with an alkyl)phenantrenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof;

[0113] As yet another example, in the above chemical formulas CY3(17) to CY3(37), R 35 is at least one C1-C 20 Alkyl group, and at least one C6-C 20 C6-C substituted with aryl groups 20 It is an aryl group.

[0114] Furthermore, according to other concrete examples, in the above chemical formula 3-2,

[0115] [ka] The group represented by is one of the following chemical formulas CY4(1) to CY4(38).

[0116] [ka] [ka]

[0117] The above chemical formulas CY4(1) to CY4(38) Y4 is C, X 41 O, S, N(R) 47 ), C(R 47 )(R 48 ), or Si(R 47 )(R 48 ) and R 41 ~R 48 For explanations regarding R, please refer to the explanation regarding R4 in this specification. 41 ~R 46 These are not hydrogen, * represents the bonding site with M1 in the above chemical formula 1. * represents the bonding site with T3 in the chemical formula 3-2 above.

[0118] Furthermore, according to other concrete examples, one R1 in the above chemical formula 3-1 (for example, in the above chemical formulas CY1-1 to CY1-4, R 11~R 18 (and the four R4s of the above chemical formula 3-2 (for example, the R of the above chemical formulas CY4(1) to CY4(38)) 41 ~R 46 These are, each independently, Hydrogen, deuterium, -F, or cyano group; or Deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl, C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, phenyl groups, (C1-C 20 C1-C 20 Alkyl, C3-C 10 The group is a cycloalkyl group, phenyl group, naphthyl group, pyridinyl group, furanyl group, thiophenyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, or dibenzothiophenyl group; however, the R of the above chemical formulas CY4(1) to CY4(38) is... 41 ~R 46 These are not hydrogen.

[0119] Furthermore, other examples indicate that organometallic compounds contain at least one deuterium atom.

[0120] In the above chemical formulas 3-1 and 3-2, 1) two or more of the multiple R1s are selectively linked to each other, and at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substituted or unsubstituted C2-C 30 1) A heterocyclic group is formed, and 2) two or more of the multiple R2s are selectively linked to each other, and at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10aSubstituted or unsubstituted C2-C 30 A heterocyclic group is formed, and 3) two or more of the multiple R3s are selectively linked to each other, and at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substituted or unsubstituted C2-C 30 A heterocyclic group is formed, and 4) two or more of the multiple R4s are selectively linked to each other, and at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substituted or unsubstituted C2-C 30 A heterocyclic group is formed, and 5) Two or more of R1 to R4, R7 and R8 are selectively linked to each other, and at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substituted or unsubstituted C2-C 30 It forms a heterocyclic group. In this specification, R 10a For further information, please refer to the explanation regarding R1.

[0121] In this specification, * and *' represent bonding sites with adjacent atoms, respectively, unless otherwise specified.

[0122] A method for synthesizing the organometallic compound represented by the above chemical formula 1 will be recognizable to those skilled in the art by referring to the synthesis examples described later.

[0123] Examples of organometallic compounds include one of the compounds in [Group 1] below, one of the compounds in [Group 2] below, one of the compounds in [Group 3] below, and so on.

[0124] [Group 1]

[0125] [ka] [ka]

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[0126] [グループ2]

[0127]

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[0128] [グループ3]

[0129]

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[0130] The organometallic compounds described above have a charge trapping capacity (CCA) of 4.0 to 10.5. In organic light-emitting devices employing these organometallic compounds, even with low doping concentrations of the organometallic compounds, the charge flow in the layers of the organic light-emitting device (e.g., the light-emitting layer) is effectively controlled, substantially preventing phenomena such as triplet-triplet annihilation, triplet-polaton quenching, or charge accumulation at the light-emitting layer interface, thereby significantly improving the lifespan of the organic light-emitting device. Considering the high cost of the transition metals contained in organometallic compounds, using organometallic compounds with a charge trapping capacity (CCA) of 4.0 to 10.5 allows for the mass production of low-cost, long-life organic light-emitting devices. On the other hand, organic light-emitting devices employing organometallic compounds with a charge trapping capacity (CCA) of less than 4.0 require higher doping concentrations of the organometallic compounds to achieve sufficient charge trapping capacity (CCA), resulting in high costs for producing organic light-emitting devices with equivalent performance. Therefore, using organometallic compounds with a charge trapping capacity (CCA) of less than 4.0 reduces the productivity of organic light-emitting devices.

[0131] Accordingly, the organometallic compound represented by the above chemical formula 1 is suitable for use as a dopant in the organic layer of an organic light-emitting device, for example, as a dopant in the light-emitting layer of the organic layer. In other aspects, an organic light-emitting device is provided having a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer contains one or more organometallic compounds as described herein.

[0132] According to one example, the light-emitting layer contains an organometallic compound.

[0133] In other examples, the light-emitting layer contains an organometallic compound, and the light-emitting layer emits green light. The green light has a maximum emission wavelength of, for example, 490 nm to 550 nm.

[0134] Furthermore, according to other examples, the light-emitting layer further contains a host, and the host content is greater than the organometallic compound content. For example, the organometallic compound content is 4.60 mol% or less, 1.00 mol% to 4.60 mol%, 1.00 mol% to 4.25 mol%, 1.44 mol% to 4.60 mol%, or 1.44 mol% to 4.25 mol% per 100 mol% of the light-emitting layer. Even if the organometallic compound content is selected at a low concentration of 4.6 mol% or less per 100 mol% of the light-emitting layer, the organic light-emitting element can have a long lifespan, and by utilizing organometallic compounds, long-life organic light-emitting elements can be mass-produced at low cost.

[0135] In this specification, "(the organic layer) contains one or more organometallic compounds" is interpreted as "(the organic layer) contains one organometallic compound belonging to the category of organometallic compounds described herein, or two or more different organometallic compounds belonging to the category of organometallic compounds described herein."

[0136] For example, the organic layer contains only compound 1 as an organometallic compound. In this case, compound 1 is present in the light-emitting layer of the organic light-emitting device. Alternatively, the organic layer contains both compound 1 and compound 2 as organometallic compounds. In this case, compound 1 and compound 2 are present in the same layer (for example, both compound 1 and compound 2 are present in the light-emitting layer).

[0137] 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.

[0138] 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 includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0139] In this specification, "organic layer" is a term that refers to one and / or more layers arranged between the first electrode and the second electrode in an organic light-emitting device. The "organic layer" includes not only organic compounds but also organometallic complexes containing metals.

[0140] Figure 1 schematically shows a cross-sectional view 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 1. 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 order.

[0141] A substrate is additionally placed below the first electrode 11 or above the second electrode 19. While a substrate commonly used in organic light-emitting devices can be used, a glass substrate or a transparent plastic substrate with superior mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance is preferred.

[0142] [First electrode 11 in organic light-emitting element 10]

[0143] 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 an anode. The material for the first electrode includes a material with a high work function so that hole injection is easy. The first electrode 11 is a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. As the material for the first electrode, 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.

[0144] The first electrode 11 has a single layer or a multilayer structure including two or more layers. For example, the first electrode 11 has a three-layer structure of ITO / Ag / ITO.

[0145] An organic layer 15 is placed on top of the first electrode 11.

[0146] [Organic layer 15 in organic light-emitting element 10]

[0147] The organic layer 15 includes a hole transport region, an emissive layer, and an electron transport region.

[0148] [Hole transport region in organic layer 15]

[0149] The hole transport region is located between the first electrode 11 and the light-emitting layer.

[0150] The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0151] The hole transport region may consist only of a hole injection layer or 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.

[0152] 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.

[0153] 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, but is not limited to these ranges.

[0154] 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. The coating is performed at a speed of approximately 2,000 rpm to 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, but is not limited to these ranges.

[0155] The formation conditions for the hole transport layer and electron blocking layer refer to the formation conditions for the hole injection layer.

[0156] The hole transport region includes, 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 the following chemical formula 201, compounds represented by the following chemical formula 202, or any combination thereof.

[0157] [ka]

[0158] [ka]

[0159] [ka]

[0160] In the above 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-C 60 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 is a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, or any combination thereof, and is substituted or unsubstituted with 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.

[0161] In the above chemical formula 201, xa and xb are independent integers between 0 and 5, or 0, 1, or 2. For example, xa is 1 and xb is 0, but is not limited to these.

[0162] In the above chemical formulas 201 and 202, R 101 ~R 108 , R 111 ~R 119 , and R 121 ~R 124 Each of them operates independently. Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or 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 (for example, methoxy, ethoxy, propoxy, butoxy, and pentoxy groups); 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, or any combination thereof, C1-C 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 A phenyl group, naphthyl group, anthracenyl group, fluorenyl group, or pyrenyl group, substituted or unsubstituted with an alkoxy group, or any combination thereof;

[0163] In the above chemical formula 201, R 109This 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 A phenyl group, naphthyl group, anthracenyl group, or pyridinyl group, which is substituted or unsubstituted with an alkoxy group, a phenyl group, anthracenyl group, or pyridinyl group, or any combination thereof.

[0164] According to one example, the compound represented by the above chemical formula 201 is represented by the following chemical formula 201A.

[0165] [ka]

[0166] In the above chemical formula 201A, R 101 , R 111 , R 112 , and R 109 For a detailed explanation, please refer to the section mentioned above.

[0167] For example, the hole transport region includes one of the following compounds HT1 to HT21, or any combination thereof.

[0168] [ka] [ka]

[0169] The thickness of the hole transport region is approximately 100 Å to 10,000 Å, for example, approximately 100 Å to 3,000 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 50 Å to 10,000 Å, for example, approximately 100 Å to 1,000 Å, and the thickness of the hole transport layer is approximately 50 Å to 2,000 Å, for example, approximately 100 Å to 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in the driving voltage.

[0170] The hole transport region further includes charge-generating materials in addition to the materials described above to improve conductivity. The charge-generating materials are uniformly or non-uniformly dispersed within the hole transport region.

[0171] Charge-generating substances are, for example, p-dopants. p-dopants are quinone derivatives, metal oxides, cyano group-containing compounds, or any combination thereof. For example, p-dopants are quinone derivatives such as tetracyanoquinone dimethane (TCNQ), 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4-TCNQ), and F6-TCNNQ; metal oxides such as tungsten oxide and molybdenum oxide; cyano group-containing compounds such as the compound HT-D1 below; or any combination thereof.

[0172] [ka]

[0173] The hole transport region further includes a buffer layer.

[0174] The buffer layer compensates for the optical resonance distance caused by the wavelength of light emitted from the light-emitting layer, thereby increasing efficiency.

[0175] On the other hand, if the hole transport region includes an electron blocking layer, the electron blocking layer material includes the substance used in the hole transport region as described above, the host substance described later, or any combination thereof. For example, if the hole transport region includes an electron blocking layer, the mCP described later, compound H21, or any combination thereof can be used as the electron blocking layer material.

[0176] [Emitting layer in organic layer 15]

[0177] An emissive layer can be formed above the hole transport region using methods such as vacuum deposition, spin coating, casting, or LB (Large-Layer) coating. When forming the emissive layer by vacuum deposition or spin coating, the deposition and coating conditions vary depending on the compound used, and are generally selected from a range of conditions that are approximately the same as those used for forming the hole injection layer.

[0178] The light-emitting layer comprises a host and a dopant, the dopant comprising an organometallic compound represented by the above chemical formula 1 as described herein.

[0179] [Host in the luminescent layer]

[0180] The host contains TPBi, TBADN, ADN (also known as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, compound H52, or any combination thereof.

[0181] [ka]

[0182] On the other hand, the host consists of one type of compound, or a mixture of two or more different compounds.

[0183] According to one embodiment, the host includes an electron-transporting host containing at least one electron-transporting moisture, a hole-transporting host not containing an electron-transporting moisture, or any combination thereof.

[0184] In this specification, electron-transporting moiety includes a cyano group, a π-electron-deficient nitrogen-containing ring group, a group represented by one of the following chemical formulas, or any combination thereof.

[0185] [ka]

[0186] In the chemical formula above, *, *', and *'' are bonding sites with any adjacent atom.

[0187] For example, an electron-transporting host includes at least one π-electron-rich ring group and at least one electron-transporting moiety.

[0188] As another example, a hole-transporting host contains at least one π-electron-excess ring group and does not contain an electron-transporting moiety.

[0189] According to other examples, the host includes electron-transporting hosts and hole-transporting hosts, and electron-transporting hosts and hole-transporting hosts are distinct from each other.

[0190] In this specification, "π-electron deficient nitrogen-containing ring group" refers to a ring group having at least one *-N=*' moiety, and examples include imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, sinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, and the like.

[0191] On the other hand, π-electron-rich ring groups are ring groups that do not contain *-N=*' moiety, and examples of such groups include benzene, heptalene, indene, naphthalene, azulene, indacene, acenaphthylene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluorantene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentacene, hexacene, and pentacene groups. Examples include rubicene group, colosene group, ovalen group, pyrrole group, isoindole group, indole group, furan group, thiophene group, benzofuran group, benzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiophenesulfon group, carbazole group, dibenzosilole group, indenocarbazole group, indolocarbazole group, benzoflocarbazole group, benzothienocarbazole group, and triindrobenzene group.

[0192] Furthermore, other examples indicate that electron-transporting hosts include compounds represented by the following chemical formula E-1.

[0193] Furthermore, other examples indicate that hole-transporting hosts include compounds represented by the following chemical formula H-1.

[0194] [Cade E-1] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0195] In the above chemical formula E-1, Ar 301 This is at least one R 10a Substitute or non-substitute C5-C 60 A carbon ring group, or at least one R 10a Substitute or non-substitute C1-C 60 It is a heterocyclic group, xb11 is 1, 2, or 3. L 301 Each is independently a single bond, a group represented by one of the following chemical formulas, and at least one R 10a Substitute or non-substitute C5-C 60 A carbon ring group, or a C1-C group substituted or unsubstituted with at least one R10a. 60 It is a heterocyclic group, and in the chemical formula below, *, *', and *'' are bonding sites with any adjacent atom, respectively. [ka] xb1 is an integer between 1 and 5. R 301 C1-C5 is hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, 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, 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 Heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -Si(Q 301 )(Q 302 )(Q 303 ), -N(Q 301 )(Q 302 ), -B(Q301 )(Q 302 ), -C(=O)(Q 301 ), -S(=O)2(Q 301 ), -S(=O)(Q 301 ), -P(=O)(Q 301 )(Q 302 ), or -P(=S)(Q 301 )(Q 302 ) and xb21 is selected from integers between 1 and 5. Q 301 ~Q 303 These are, independently, C1-C 10 Alkyl alkyl group, C1-C 10 It is an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group. R 10a For further explanation, please refer to the explanation regarding R1 in this specification. At least one of the following conditions 1 to 3 must be satisfied.

[0196] <Condition 1>

[0197] Ar of the above chemical formula E-1 301 , L 301 , and R 301 At least one of these independently contains a π-electron-deficient nitrogen-containing ring group.

[0198] <Condition 2>

[0199] L of the above chemical formula E-1 301 It is a group represented by one of the following chemical formulas.

[0200] [ka]

[0201] <Condition 3>

[0202] R in the above chemical formula E-1 301 This is a cyano group, -S(=O)2(Q 301 ), -S(=O)(Q 301), -P(=O)(Q 301 )(Q 302 ), or -P(=S)(Q 301 )(Q 302 )

[0203] [Chemical H-1] Ar 401 -(L 401 ) xd1 -(Ar 402 ) xd11

[0204] [ka]

[0205] [ka]

[0206] In the above chemical formulas H-1, 11, and 12, L 401 teeth, Single bond; or Deuterium, C1-C 10 Alkyl alkyl group, C1-C 10 Alkoxy groups, π-electron-excess ring groups (e.g., phenyl group, naphthyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, triphenylenyl group, biphenyl group, terphenyl group, tetraphenyl group, etc.), -Si(Q 401 )(Q 402 )(Q 403) or any combination thereof, substituted or unsubstituted, π-electron-excess ring groups (e.g., benzene group, heptalene group, indene group, naphthalene group, azulene group, indacene group, acenaphthylene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluorantene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentacene group, hexacene group, rubice These include the following groups: n group, colosene group, ovalen group, pyrrole group, isoindole group, indole group, furan group, thiophene group, benzofuran group, benzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiophenesulfone group, carbazole group, dibenzosilole group, indenocarbazole group, indolocarbazole group, benzoflocarbazole group, benzothienocarbazole group, triindrobenzene group, etc. xd1 is an integer between 1 and 10, and if xd1 is 2 or greater, then L is 2 or greater. 401 They are either identical to each other or different from each other. Ar 401 This is a group represented by the above chemical formula 11, or a group represented by the above chemical formula 12. Ar 402 teeth, The group represented by the above chemical formula 11, or the group represented by the above chemical formula 12; or Deuterium, C1-C 20 Alkyl alkyl group, C1-C 20 Alkoxy groups, π-excess ring groups (e.g., phenyl group, naphthyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, biphenyl group, terphenyl group, triphenylenyl group, etc.), or π-excess ring groups (phenyl group, naphthyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, biphenyl group, terphenyl group, triphenylenyl group, etc.) substituted or unsubstituted with any combination thereof; CY 401 and CY 402These are, independently of each other, π-electron-excess ring groups (for example, benzene group, naphthalene group, fluorene group, carbazole group, benzocarbazole group, indolocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthosilole group, etc.), A 21 This is a single bond, O, S, N(R) 51 ), C(R 51 )(R 52 ), or Si(R 51 )(R 52 ) and A 22 This is a single bond, O, S, N(R) 53 ), C(R 53 )(R 54 ), or Si(R 53 )(R 54 ) and A in the above chemical formula 12 21 and A 22 In this, at least one is not a single bond, R 51 ~R 54 , R 60 and R 70 Each of them operates independently. Hydrogen or deuterium; Deuterium, π-electron excess ring groups (e.g., phenyl group, naphthyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, etc.), or any combination thereof, C1-C 20 Alkyl and C1-C 20 Alkoxy group; Deuterium, C1-C 20 Alkyl alkyl group, C1-C 20Alkoxy groups, π-excess ring groups (e.g., phenyl group, naphthyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, biphenyl group, etc.), or π-excess ring groups substituted or unsubstituted with any combination thereof (e.g., phenyl group, naphthyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, biphenyl group, terphenyl group, triphenylenyl group, etc.); or -4(Q 404 )(Q 405 )(Q 406 ); and e1 and e2 are independent integers between 0 and 10. Q 401 ~Q 406 These are, independently, hydrogen, deuterium, and C1-C 20 Alkyl alkyl group, C1-C 20 These are alkoxy groups or π-electron-excess ring groups (for example, phenyl groups, naphthyl groups, fluorenyl groups, carbazolyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, biphenyl groups, etc.), * indicates a bonding site with an adjacent atom.

[0207] According to one example, in the above chemical formula E-1, Ar 301 Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32), or any combination thereof, substituted or unsubstituted, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluorantene group, triphenylene group, pyrene group, chrysene group, naphthalene group, picene group, perylene group, pentaphene group, indenoanthracene group, dibenzofuran group, or dibenzothiophene group, xb1 piece L 301 At least one of these is independently deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32 ), or any combination thereof, substituted or unsubstituted imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, sinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, or azacarbazole group, R 301These are hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl alkyl group, C1-C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, tetraphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), or -P(=O)(Q 31 )(Q 32 ) and Q 31 ~Q 33 These are, independently, C1-C 10 Alkyl alkyl group, C1-C 10 It is an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0208] According to other concrete examples, R 301 This is a chemical formula represented by one of the following chemical formulas 7-1 to 7-9.

[0209] [ka]

[0210] The electron-transporting host is selected from, for example, the following compounds H-E1 to H-E84.

[0211] [ka] [ka] [ka] [ka] [ka] [ka]

[0212] As another example, the hole-transporting host is selected from the following compounds H-H1 to H-H103.

[0213] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0214] Furthermore, according to other embodiments, the host comprises an electron-transporting host and a hole-transporting host, the electron-transporting host comprises a triphenylene group and a triazine group, and the hole-transporting host comprises a carbazole group.

[0215] The weight ratio of electron-transporting host to hole-transporting host is 1:9 to 9:1, for example, 2:8 to 8:2, and as another example, in the range of 4:6 to 6:4. When the weight ratio of electron-transporting host to hole-transporting host satisfies the above range, a balance of hole transport and electron transport into the light-emitting layer can be achieved.

[0216] When an 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 have a structure in which a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer are stacked to emit white light, and various other modifications are possible.

[0217] The thickness of the light-emitting 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 above range, excellent light emission characteristics can be achieved without a substantial increase in the driving voltage.

[0218] [Electron transport region in the light-emitting layer]

[0219] Next, an electron transport region is placed above the light-emitting layer.

[0220] The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0221] For example, the electron transport region has a hole blocking layer / electron transport layer / electron injection layer structure, or an electron transport layer / electron injection layer structure. The electron transport layer has a single-layer structure or a multilayer structure containing two or more different materials.

[0222] 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.

[0223] If the electron transport region includes a hole blocking layer, the hole blocking layer includes, for example, at least one of the following: BCP, Bphen, and BAlq.

[0224] [ka]

[0225] 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.

[0226] The thickness of the hole blocking layer is approximately 20 Å to 1,000 Å, for example, approximately 30 Å to 600 Å. When the thickness of the hole blocking layer satisfies the above range, excellent hole blocking characteristics can be obtained without a substantial increase in the driving voltage.

[0227] The electron transport layer includes the above BCP, Bphen, TPBi, Alq3, BAlq, TAZ, NTAZ, or any combination thereof.

[0228] [ka]

[0229] Alternatively, the electron transport layer may contain one of the following compounds ET1 to ET25, or any combination thereof.

[0230] [ka] [ka]

[0231] The thickness of the electron transport layer is approximately 100 Å to 1,000 Å, for example, approximately 150 Å to 500 Å. When the thickness of the electron transport layer satisfies the above range, satisfactory electron transport characteristics can be obtained without a substantial increase in the driving voltage.

[0232] The electron transport layer further contains metal-containing materials in addition to the materials mentioned above. Metal-containing substances include Li complexes. Li complexes include, for example, the following compounds ET-D1 or ET-D2.

[0233] [ka]

[0234] Furthermore, the electron transport region includes an electron injection layer that facilitates the injection of electrons from the second electrode 19.

[0235] The electron injection layer contains LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.

[0236] The thickness of the electron injection layer is approximately 1 Å to 100 Å, for example, approximately 3 Å to 90 Å. When the thickness of the electron injection layer satisfies the above range, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0237] A second electrode 19 is placed 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 with a relatively low work function, or any combination thereof can be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc., which 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.

[0238] The above describes organic light-emitting devices with reference to Figure 1, but they are not limited to those described above.

[0239] Further, from another perspective, organic light-emitting elements are included in electronic devices. Therefore, electronic devices containing organic light-emitting elements are provided. These electronic devices include, for example, displays, lighting, sensors, and the like.

[0240] Furthermore, from another perspective, a diagnostic composition is provided that contains one or more organometallic compounds represented by the above chemical formula 1.

[0241] Since the organometallic compound represented by the above chemical formula 1 provides high luminescence efficiency, a diagnostic composition containing the organometallic compound has high diagnostic efficiency.

[0242] Diagnostic compositions are used in a wide variety of applications, including various diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0243] 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.

[0244] In this specification, C1-C 60 Alkyl alkyl group, C1-C 20 Alkyl alkyl groups, and / or C1-C 10Examples 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 includes mixed-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, the above chemical formula 9-33 is a branched C6 alkyl group, which can be seen as a tert-butyl group substituted with two methyl groups.

[0245] 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).

[0246] In this specification, C1-C 60 Alkoxy group, C1-C 20 Alkoxy group, or C1-C 10Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, and pentoxy groups.

[0247] In this specification, C2-C 60 The alkenyl group is C2-C 60 A structure having one or more carbon-carbon double bonds in the middle or terminal of an alkyl group, specific examples of which include ethenyl, propenyl, and butenyl groups. In this specification, C2-C 60 The alkenylene group is C2-C 60 This refers to a divalent group that has the same structure as an alkenyl group.

[0248] In this specification, C2-C 60 The alkynyl group is C2-C 60 A structure having one or more carbon-carbon triple bonds in the middle or terminal of an alkyl group, specific examples of which include an ethynyl group, a propynyl group, etc. 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.

[0249] In this specification, C3-C 10 Cycloalkyl groups are C3-C 10 This refers to a monovalent saturated hydrocarbon monocyclic group, C3-C 10 The cycloalkylene group is the C3-C 10 This refers to a divalent group having the same structure as a cycloalkyl group.

[0250] In this specification, C3-C 10 Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, norbornanyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl.

[0251] In this specification, C1-C 10A 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.

[0252] In this specification, C1-C 10 Examples of heterocycloalkyl groups include siloranil, silinanil, tetrahydrofuranil, tetrahydro-2H-pyranil, and tetrahydrothiophenyl groups.

[0253] 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.

[0254] 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.

[0255] In this specification, C6-C 60The aryl group is C6-C 60 This refers to a monovalent group having a carbon-ring aromatic system, C6-C 60 The arylene group is C6-C 60 This refers to a divalent group having a carbon-ring 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 are fused to each other.

[0256] In this specification, C7-C 60 The alkylaryl group has at least one C1-C 60 C6-C substituted with alkyl group 60 It means an aryl group.

[0257] In this specification, C1-C 60 The heteroaryl group contains at least one heteroatom selected from N, O, P, Si, S, Ge, Se, and B as a ring-forming atom, and C1-C 60 This refers to a monovalent group having a cyclic aromatic system, C1-C 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, and 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, the two or more rings are fused to each other.

[0258] In this specification, C2-C 60 The alkyl heteroaryl group has at least one C1-C 60 C1-C substituted with alkyl group 60 It means a heteroaryl group.

[0259] In this specification, C6-C 60 The aryloxy group is -OA 102 (Here, A 102 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 is an aryl group) and C1-C 60 The alkylthio group is -SA 104 (Here, A 104 C1-C 60 It indicates that it is an alkyl group.

[0260] 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.

[0261] 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 condensed with 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. A monovalent non-aromatic heterocondensed polycyclic group includes a carbazolyl group, etc. 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.

[0262] In this specification, C5-C 30 A carbocyclic group is a saturated or unsaturated ring group having only 5 to 30 carbon atoms as ring-forming atoms. C5-C 30 A carbocyclic group is either a monocyclic or polycyclic group. (At least one R 10a (Substituted or not substituted) C5-C30 A "carbon ring group" is, for example, (at least one R 10a This includes adamantane group, norbornene group, norbornane group (bicyclo[2.2.1]heptane 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, silole group, fluorene group, etc. (substituted or unsubstituted).

[0263] 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, Se, Ge, B, and S. C1-C 30 A heterocyclic group is either a monocyclic or polycyclic group. (At least one R 10a (Substituted or not substituted) C1-C 30 A heterocyclic group is, for example, (at least one R 10aThiophene group, furan group, pyrrole group, silole group, borol group, phosphole group, selenofen group, gelmol group, benzothiophene group, benzofuran group, indole group, indene group, benzosilole group, benzoborol group, benzophosphole group, benzoselenophene group, benzogermol group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzosilole group, dibenzoborol group, dibenzophosphole Azabenzothiophene group, dibenzoselenophene group, dibenzogermole 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, azabenzogermole group, azadibenzothiophene group, azadibenzofuran group, Zacarbazole 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, quinoxaline group, quinazoline This includes groups such as 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, and 5,6,7,8-tetrahydroquinoline group.

[0264] In this specification, "Deuterated C1-C 60 Alkyl group (or deuterated C1-C 20 (Alkyl groups, etc.), Deuterated C3-C 10 Cycloalkyl group, Deuterated C1-C 10The heterocycloalkyl group and the deuterated phenyl group are each C1-C groups substituted with at least one deuterium atom. 60 Alkyl group (or C1-C 20 (Alkyl alkyl groups, etc.), C3-C 10 Cycloalkyl groups, C1-C 10 This refers to heterocycloalkyl groups and phenyl groups. For example, "deuterated C1 alkyl group (i.e., deuterated methyl group)" includes -CD3, -CD2H and -CDH2, and "deuterated C3-C 10 For an example of a "cycloalkyl group," see, for example, chemical formula 10-501 above. 60 Alkyl groups (or deuterated C1-C20 alkyl groups, etc.), deuterated C3-C 10 Cycloalkyl group, Deuterated C1-C 10 "Heterocycloalkyl group" or "deuterated phenyl group" is a fully deuterated C1-C group in which all hydrogen atoms in each group are replaced with deuterium. 60 Alkyl group (or fully deuterated C1-C 20 Alkyl groups, etc.), fully deuterated C3-C 10 Cycloalkyl groups, fully deuterated C1-C 10 ii) a heterocycloalkyl group, or a fully deuterated phenyl group, or a partially deuterated C1-C group in which not all hydrogen atoms in each group are replaced with deuterium. 60 Alkyl group (or partially deuterated C1-C 20 (Alkyl groups, etc.), partially deuterated C3-C 10 Cycloalkyl groups, partially deuterated C1-C 10 It is a heterocycloalkyl group, or a partially deuterated phenyl group.

[0265] In this specification, "(C1-C 20 The alkyl group "X" means 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 having at least one C1-C20 C3-C substituted with alkyl group 10 This indicates a cycloalkyl group, and is defined as "(C1-C 20 A "(alkyl)phenyl group" means 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.

[0266] 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" are, respectively This refers to a heterocycle that shares 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, dibenzogermol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, and dibenzothiophene 5,5-dioxide group," but in which at least one of the carbon atoms forming the ring is substituted with nitrogen.

[0267] The substituted C5-C mentioned above 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 C1-C 60Alkylthio group, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocycloalkyl groups, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C7-C 60 Alkylaryl group, substituted C6-C 60 Aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 heteroaryl group, substituted C2-C 60 The alkyl heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituents of the substituted monovalent non-aromatic heterocondensed polycyclic group are each independently: 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-C60 Alkyl heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ), or 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 ), -B(Q 26 )(Q27 ), -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 ), -B(Q 36 )(Q 37 ), -P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 ); or Any combination of those;

[0268] In this specification, Q1 to Q9, Q 11 ~Q 19 Q 21 ~Q 29 , and Q 31 ~Q 39 These are, independently, 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 60 A C1-C group substituted or unsubstituted with an aryl group, or any combination thereof. 60Alkyl alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; C3-C 10 Cycloalkyl group; C1-C 10 Heterocycloalkyl 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 is a heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic heterocondensed polycyclic group.

[0269] The following describes a compound and an organic light-emitting element according to one embodiment of the present invention, with reference to synthesis examples and embodiments. However, the present invention is not limited to the following synthesis examples and embodiments. In the following synthesis examples, 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.

[0270] [Examples]

[0271] ≪Synthesis example 1 (compound D10)≫

[0272] [ka]

[0273] <Synthesis of compound D10(1)>

[0274] 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine (7.5 g, 26.7 mmol) and iridium chloride (4.1 g, 11.9 mmol) were mixed with 120 mL of ethoxyethanol and 40 mL of distilled water. The mixture was then stirred under reflux for 24 hours and then cooled to room temperature. The resulting solid was filtered and thoroughly washed with water / methanol / hexane in that order. The obtained solid was dried in a vacuum oven to obtain compound D10(1) 7.43 g (79% yield).

[0275] <Synthesis of compound D10(2)>

[0276] Compound D10(1) (3.0 g, 1.91 mmol) was mixed with 60 mL of methylene chloride, and then AgOTf (0.98 g, 3.81 mmol) was added after being mixed with 20 mL of methanol. The mixture was then stirred at room temperature for 18 hours while shielded from light with aluminum foil, and the resulting solid was removed by Celite filtration. The filtrate was then reduced in pressure to obtain a solid (compound D10(2)), which was used in the next reaction without further purification.

[0277] <Synthesis of Compound D10>

[0278] Compound D10(2) (3.68 g, 3.79 mmol) and 2-methyl-8-(1-methyl-1H-benzo[d]imidazol-2-yl)benzofuro[2,3-b]pyridine (4.17 mmol) were mixed with 50 mL of 2-ethoxyethanol and 50 mL of dimethylformamide. The mixture was stirred under reflux at 130°C for 48 hours, after which the temperature was reduced. The resulting mixture was then reduced under reduced pressure to obtain a solid, which was subjected to column chromatography under methylene chloride (MC):hexane conditions to obtain 1.8 g of compound D10 (44% yield). The substance was identified by mass spectrometry and HPLC (high-performance liquid chromatography). HRMS (MALDI) calcd for C 56 H 62 IrN5OSi2:m / z 1069.4122 found:1069.4128

[0279] ≪Synthesis Example 2 (Compound D11)≫

[0280] [ka]

[0281] <Synthesis of compound D11(1)>

[0282] Compound D11(1) was synthesized using the same method as the synthesis method for compound D10(1) in Synthesis Example 1, except that 8-(4-isopropylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0283] <Synthesis of compound D11(2)>

[0284] Compound D11(2) was synthesized using the same method as the synthesis method for compound D10(2) in Synthesis Example 1 above, except that compound D11(1) was used instead of compound D10(1).

[0285] <Synthesis of Compound D11>

[0286] Except for using compound D11(2) and 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine instead of compound D10(2) and 2-methyl-8-(1-methyl-1H-benzo[d]imidazole-2-yl)benzofl[2,3-b]pyridine, the same method as the synthesis of compound D10 in Synthesis Example 1 was used to obtain 0.7 g of compound D11 (32% yield). The substance was identified by analysis of mass spectrum and HPLC. HRMS (MALDI) calcd for C 58 H 58 IrN5O2Si:m / z 1077.3989 found:1077.3995

[0287] <<Synthesis Example 3 (Compound D12)>>

[0288] [ka]

[0289] Compound D12 (0.8 g, 36% yield) was obtained using the same method as the synthesis of compound D10 in Synthesis Example 1 above, except that 8-(4-isobutylpyridin-2-yl)-2-(methyl-d3)-benzofuro[2,3-b]pyridine was used instead of 2-methyl-8-(1-methyl-1H-benzo[d]imidazole-2-yl)benzofuro[2,3-b]pyridine. The substance was identified by mass spectrometry and HPLC analysis. HRMS (MALDI) calcd for C 57 H67 IrN4OSi2:m / z 1072.4483 found:1072.4476

[0290] <<Synthesis Example 4 (Compound D13)>>

[0291] [ka]

[0292] Compound D13 was obtained in 0.7 g (41% yield) using the same method as the synthesis of compound D10 in Synthesis Example 1 above, except that 8-(4-isopropylpyridine-2-yl)-2-methylbenzoflo[2,3-b]pyridine was used instead of 2-methyl-8-(1-methyl-1H-benzo[d]imidazole-2-yl)benzoflo[2,3-b]pyridine. The substance was identified by analysis of mass spectrum and HPLC. HRMS (MALDI) calcd for C 56 H 65 IrN4OSi2:m / z 1058.4326 found:1058.4321

[0293] ≪Synthesis Example 5 (Compound D14)≫

[0294] [ka]

[0295] <Synthesis of compound D14(1)>

[0296] Compound D14(1) was synthesized using the same method as the synthesis method for compound D10(1) in Synthesis Example 1, except that 5-(trimethylsilyl)-2-phenylpyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0297] <Synthesis of compound D14(2)>

[0298] Compound D14(2) was synthesized using the same method as the synthesis method for compound D10(2) in Synthesis Example 1 above, except that compound D14(1) was used instead of compound D10(1).

[0299] <Synthesis of Compound D14>

[0300] Compound D14 was synthesized using the same method as for compound D10 in Synthesis Example 1 above, except that compound D14(2) and 8-(1-(3,5-isobutyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)-4-dibenzofuran) were used instead of compound D10(2) and 2-methyl-8-(1-methyl-1H-benzo[d]imidazol-2-yl)benzofro[2,3-b]pyridine, respectively. 1.2 g of compound D14 (30% yield) was obtained using the same method as for compound D10 in Synthesis Example 1 above. The substance was identified by analysis of mass spectrum and HPLC. HRMS (MALDI) calcd for C 64 H 61 IrN4OSi2:m / z 1150.4013 found:1150.4019

[0301] <<Synthesis Example 6 (Compound D15)>>

[0302] [ka]

[0303] Compound D15, 1.8 g (47% yield), was obtained using the same method as the synthesis of compound D10 in Synthesis Example 1, except that 2-methyl-8-(1-biphenyl-1H-benzo[d]imidazol-2-yl)benzofuro[2,3-b]pyridine was used instead of 2-methyl-8-(1-biphenyl-1H-benzo[d]imidazol-2-yl)benzofuro[2,3-b]pyridine. The substance was identified by mass spectrometry and HPLC analysis. HRMS (MALDI) calcd for C 67 H 68 IrN5OSi2:m / z 1207.4592 found:1207.4585

[0304] ≪Synthesis Example 7 (Compound D16)≫

[0305] [ka]

[0306] Compound D16 was obtained in 1.8 g (47% yield) using the same method as the synthesis of compound D10 in Synthesis Example 1 above, except that 8-(1-(3,5-diisopropyl-[1,1'-biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine) was used instead of 2-methyl-8-(1-methyl-1H-benzo[d]imidazol-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine. The substance was identified by analysis of the mass spectrum and HPLC. HRMS (MALDI) calcd for C 67 H 68IrN5OSi2:m / z 1207.4592 found:1207.4585

[0307] ≪Synthesis Example 8 (Compound D17)≫

[0308] [ka]

[0309] <Synthesis of compound D17(1)>

[0310] Compound D17(1) was synthesized using the same method as the synthesis method for compound D10(1) in Synthesis Example 1, except that 4-(2-methylpropyl-1,1-d2)-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0311] <Synthesis of compound D17(2)>

[0312] Compound D17(2) was synthesized using the same method as the synthesis method for compound D10(2) in Synthesis Example 1 above, except that compound D17(1) was used instead of compound D10(1).

[0313] <Synthesis of Compound D17>

[0314] Compound D17 was synthesized using the same method as for compound D10 in Synthesis Example 1, except that compound D17(2) and 2-(dibenzo[b,d]furan-4-yl)-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole were used instead of compound D10(2) and 2-methyl-8-(1-methyl-1H-benzo[d]imidazole-2-yl)benzofro[2,3-b]pyridine. Compound D17 1.9 g (43% yield) was obtained using the same method as for compound D10 in Synthesis Example 1. The substance was identified by analysis of mass spectrum and HPLC. HRMS (MALDI) calcd for C 73 H 75 IrN4OSi2:m / z 1280.5673 found:1280.5671

[0315] ≪Synthesis Example 9 (Compound D18)≫

[0316] [ka]

[0317] Compound D18 was obtained in 2.5 g (32% yield) using the same method as the synthesis of compound D10 in Synthesis Example 1 above, except that 8-(1-(5'-(tert-butyl)-[1,1':3',1”-terphenyl]-2'-yl)-1H-benzo[d]imidazol-2-yl)-4-dibenzofuran was used instead of 2-methyl-8-(1-methyl-1H-benzo[d]imidazol-2-yl)benzofro[2,3-b]pyridine. The substance was identified by analysis of the mass spectrum and HPLC. HRMS (MALDI) calcd for C 77 H79 IrN4OSi2: m / z 1324.5422 found: 1324.5416

[0318] ≪Evaluation Example 1≫

[0319] The dipole moments (DM) and polarization determinants (PD) of each of Compounds D1 - D8 and Compounds D10 - D18 were evaluated by density functional theory (DFT) calculations based on Hartree atomic units, and from these, the charge capture ability (CCA) of each compound was calculated using <Equation 1> described herein (i.e., 5×10 -9 ×DM×PD) and shown in Table 1 below. Specifically, when evaluating DM and PD, the Gaussian09 program was used. When using the Gaussian09 program, for the metals contained in Compounds D1 - D8 and Compounds D10 - D18, the B3LYP / LanL2DZ function was used, and for the organic ligands contained in Compounds D1 - D8 and Compounds D10 - D18, the B3LYP / 6 - 31G(D,P) function was used to optimize the molecular structure of each compound.

[0320]

Table 1

[0321]

Chemical Structure

[0322] From Table 1 above, it can be confirmed that the charge capture ability (CCA) of Compounds D1 - D⑧ is less than 4.0, while the charge capture ability (CCA) of Compounds D10 - D18 belongs to the range of 4.0 - 10.5.

[0323] <Fabrication of OLED D1 - 1>

[0324] As an anode, a glass substrate with patterned ITO was cut into a size of 50 mm × 50 mm × 0.5 mm, ultrasonically cleaned with isopropyl alcohol and pure water for more than 5 minutes respectively, then irradiated with ultraviolet light for 30 minutes to be exposed to ozone for cleaning, and then installed in a vacuum evaporation apparatus.

[0325] On the top of the anode, compound HT3 and compound F6-TCNNQ were vacuum co-evaporated at a weight ratio of 98:2 to form a 100 Å thick hole injection layer. After compound HT3 was vacuum-evaporated on the top of the hole injection layer to form a 1,350 Å thick hole transport layer, a 300 Å thick electron blocking layer was formed with compound H-H1 on the top of the hole transport layer.

[0326] Next, compound H-H1, compound H-E43, and compound D1 (dopant) were co-evaporated on the electron blocking layer to form a 400 Å thick light-emitting layer. Here, the weight ratio of compound H-H1 to compound H-E43 was 1:1, and the content of compound D1 was adjusted to 2.86 mol% per 100 mol% of the light-emitting layer as described in Table 2 below.

[0327] Thereafter, compound ET3 and compound ET-D1 were co-evaporated at a volume ratio of 50:50 on the top of the light-emitting layer to form a 350 Å thick electron transport layer. Compound ET-D1 was vacuum-evaporated on the top of the electron transport layer to form a 10 Å thick electron injection layer. By vacuum-evaporating Al on the top of the electron injection layer to form a 1,000 Å thick cathode, an organic light-emitting device was fabricated.

[0328]

Chemical formula

[0329] <Fabrication of OLED D1-2 to OLED D8-5 and OLED D10-1 to OLED D18-5>

[0330] OLEDs D1-2 to D8-5 and OLEDs D10-1 to D18-5 were prepared using the same method as for OLED D1-1, except that the compounds used as dopants and / or the dopant content were changed as described in Tables 2 and 3 below, respectively.

[0331] ≪Evaluation Example 2≫

[0332] The lifespan (LT) of each OLED D1-1 to OLED D8-5 and OLED D10-1 to OLED D18-5 (a total of 85 OLEDs) 97 The lifespan (LT) was evaluated and the results are shown in Tables 2 and 3 below. A current / voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation equipment. 97 (At 16,000 nits) The time (hr) required to reach 97% brightness compared to the initial brightness of 100% was evaluated. The lifetime (LT) is shown in Tables 2 and 3 below. 97 The values ​​are given as relative values ​​(%), but here we have the lifetime (LT) of five elements using the same dopant. 97 The longest lifespan of the four elements (LT97) is listed as 100%, and the lifespan of the remaining four elements (LT97) is listed. 97 The lifespan (LT) of the elements employing different dopants is listed as a relative value. 97 Even if the relative value (%) of those elements is listed as 100%, the lifespan (LT) of those elements is still uncertain. 97 The absolute value (hr) of the lifespan (LT) of OLED D1-5 and OLED D2-5 is not necessarily the same. 97 The relative values ​​(%) are all listed as 100%, but the lifespan (LT) of OLED D1-5 and OLED D2-5 is different. 97The absolute values ​​(hr) of ) are different from each other. Figure 2 is a contour plot showing the data from Tables 2 and 3 below, where the x-axis represents charge trapping ability (CCA), the y-axis represents dopant content (mol%) per 100 mol% of the light-emitting layer, and the z-axis is shaded to show the relative lifetime (%) of an organic light-emitting device having a light-emitting layer containing a dopant with charge trapping ability (CCA) as the content (mol%) on the y-axis.

[0333] [Table 2]

[0334] [Table 3]

[0335] From Table 2 and Figure 2 above, in devices employing compounds D1 to D8, each having a charge trapping ability (CCA) of less than 4.0, 100% lifetime (LT) 97 A device with a relative value (%) of ) can be confirmed to be a device in which the dopant content exceeds 4.6 mol% per 100 mol% of the light-emitting layer. Notably, in devices employing each of compounds D1 to D4, the lifetime (LT) of 100% 97 It can be confirmed that a device with a relative value (%) of ) is a device in which the dopant content is 10 mol% or more per 100 mol% of the light-emitting layer. However, from Table 3 and Figure 2 above, in devices employing compounds D10 to D18, each having a charge trapping ability (CCA) of 4.0 or higher, 100% lifetime (LT 97 A device with a relative value (%) of ) can be confirmed to be a device with a dopant content of 4.6 mol% or less.

[0336] From the above, it can be confirmed that when using dopants with a charge capture capacity (CCA) of less than 4.0, a relatively high dopant concentration must be adopted to realize a long-life organic light-emitting device. However, when using dopants with a charge capture capacity (CCA) of 4.0 or higher, a long-life organic light-emitting device can be realized even with a relatively low dopant concentration. Therefore, by using dopants with a charge capture capacity (CCA) of 4.0 or higher, it is possible to mass-produce long-life organic light-emitting devices at low cost.

[0337] Although embodiments of the present invention have been described in detail above, the present invention is not limited to the embodiments described above, and can be modified and implemented in various ways without departing from the technical spirit of the present invention. [Explanation of symbols]

[0338] 10 Organic light-emitting devices 11 1st electrode 15 Organic layer 19 2nd electrode

Claims

1. It has a charge trapping ability (CCA) of 4.0 to 10.5, An organometallic compound characterized by being represented by any of the following compounds D10 to D18. The aforementioned charge trapping ability is expressed by the following equation <Equation 1>, [Mathematics 1] Charge trapping energy (CCA) = 5 × 10 －９ ×DM×PD In the above formula 1, DM is the dipole moment of the organometallic compound, evaluated by density functional theory (DFT) calculations based on Hartree atomic units. PD is the polarization matrix of the organometallic compound, evaluated by density functional theory (DFT) calculations based on Hartree atomic units.

2. The organometallic compound according to claim 1, characterized by having a charge trapping ability (CCA) of 4.30 to 10.

25.

3. The organometallic compound according to claim 1, characterized by emitting green light.

4. The organometallic compound according to claim 1, characterized by emitting light having a maximum emission wavelength of 490 nm to 550 nm.

5. First electrode and A second electrode facing the first electrode, It has an organic layer disposed between the first electrode and the second electrode, which includes 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 4.

6. The light-emitting layer contains the organometallic compound, The organic light-emitting element according to claim 5, characterized in that the light-emitting layer emits green light.

7. The light-emitting layer further includes a host, The organic light-emitting element according to claim 6, characterized in that the host content is greater than the organometallic compound content.

8. The organic light-emitting element according to claim 7, characterized in that the content of the organometallic compound in the light-emitting layer is 4.60% or less of the total number of moles of the host and the organometallic compound.

9. The organic light-emitting element according to claim 7, characterized in that the content of the organometallic compound in the light-emitting layer is 1.00% to 4.25% with respect to the total number of moles of the host and the organometallic compound.

10. The organic light-emitting element according to claim 7, characterized in that the content of the organometallic compound in the light-emitting layer is 1.44% to 4.25% of the total number of moles of the host and the organometallic compound.

11. An electronic device characterized by including the organic light-emitting element described in claim 7.

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