Organometallic compounds, organic light-emitting diodes containing the same, and organic light-emitting devices.

Abstract

To provide a novel organometallic compound that improves limitations in emission efficiency and lifespan of a dopant, and an organic light emitting diode and an organic light emitting display device including the same in an emission material layer.SOLUTION: For example, an organometallic compound represented by the following chemical formula 238 is illustrated.SELECTED DRAWING: Figure 3

Description

Technical Field

[0001] The present invention relates to metal compounds, and more particularly, to an organometallic compound having improved luminous efficiency and luminous lifetime, an organic light emitting diode containing the same, and an organic light emitting device.

Background Art

[0002] Recently, with the increase in the size of display devices, the demand for flat display elements that occupy less space has been increasing. As one of such flat display elements, there is an organic light emitting diode, and the technology of an organic light emitting display (OLED) device, also called an organic electroluminescent device, has been developing rapidly.

[0003] An organic light emitting diode is formed between an electron injection electrode (negative electrode) and a hole injection electrode (positive electrode), and includes an organic light emitting layer containing a host and a dopant. When charges are injected into the organic light emitting layer, electrons and holes pair up and then emit light while disappearing. The device can be formed not only on a flexible transparent substrate such as plastic, but also can be driven at a low voltage, has relatively low power consumption, and has an advantage of excellent color purity. Dopants are classified into fluorescent substances and phosphorescent substances.

[0004] In conventional general fluorescent substances, only singlet excitons participate in light emission, so the luminous efficiency is low. Phosphorescent substances in which triplet excitons also participate in light emission have higher luminous efficiency than fluorescent substances. However, an organometallic compound, which is a typical phosphorescent substance, has a short luminous lifetime and has limitations in commercialization. Therefore, it is necessary to develop a compound with improved luminous efficiency and luminous lifetime.

Summary of the Invention

Problems to be Solved by the Invention

[0006] To solve the above-mentioned problems, the present invention is represented by the following chemical formula 1, [ka] In chemical formula 1, n is an integer from 0 to 2, and each of Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 is independently C, CR2, or N, and one of Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 is C, R1 is selected from the group consisting of hydrogen, deuterium, and substituted or unsubstituted C1-C20 alkyl groups, and R2 is hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, The group consists of substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, acyl groups, carbonyl groups, carboxylate groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, and phosphino groups, and X and Y are independently selected from C, N, and O, and the W ring has one of the structures shown in chemical formula 1a-1, chemical formula 1a-2, and chemical formula 1a-3. [ka] [ka] [ka] In chemical formulas 1a-1 and 1a-2, X1, X2, X3, and X4 are independently CR4 or N, and R4 is hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C1-C20 alkylamino group, or substituted or unsubstituted C1-C20 a Selected from the group consisting of a lucylsilyl group, a substituted or unsubstituted C6-C30 allyloxy group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C6-C30 arylsilyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group, In chemical formula 1a-2, X5, X6, X7, and X8 are independently CR5 or N, with at least two of them being CR5, and R5 being either a bonding site or hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, or substituted or unsubstituted C6-C30 ali groups. Selected from the group consisting of a luoxy group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C6-C30 arylsilyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, an acyl group, a carbonyl group, a carboxylate group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group. In chemical formula 1a-3, X9 is O or S, a1 is an integer from 0 to 4, and R6 is deuterium, halide, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C1-C20 alkylamino group, substituted or unsubstituted C1-C20 alkylsilyl group, substituted or unsubstituted C2-C20 alkenyl group, or substituted or unsubstituted C2-C20 alkynyl group. The present invention provides organometallic compounds selected from the group consisting of substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, acyl groups, carbonyl groups, carboxylate groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, and phosphino groups.

[0007] In one embodiment of the present invention, "XY" in chemical formula 1 is represented by one of the following chemical formulas 1b-1, 1b-2, and 1b-3. [ka] [ka] [ka] In chemical formula 1b-1, each of R7-1, R7-2, R7-3, R7-4, R7-5, R7-6, R7-7, and R7-8 is independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1-C5 alkyl groups, or substituted or unsubstituted C6-C30 aryl groups, or two adjacent R7-1, R7-2, R7-3, and R7-4 or two adjacent R7-5, R7-6, R7-7, and R7-8 are bonded to each other to form a ring. In chemical formula 1b-2, each of R8-1, R8-2, R8-3, R8-4, R8-5, and R8-6 is independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1-C5 alkyl groups, or substituted or unsubstituted C6-C30 aryl groups, or two adjacent R8-1, R8-2, R8-3, R8-4, R8-5, and R8-6 are bonded to each other to form a ring, and R8-7 is hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, or substituted or unsubstituted C1-C20 alkyl aryl groups. Selected from the group consisting of no groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, acyl groups, carbonyl groups, carboxylate groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, and phosphino groups. In chemical formula 1b-3, each of R9-1, R9-2, and R9-3 is independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1-C5 alkyl groups, or substituted or unsubstituted C6-C30 aryl groups, or two adjacent R9-1, R9-2, and R9-3 are bonded to each other to form a ring.

[0008] In one embodiment of the present invention, the chemical formula 1 is represented by one of the following chemical formulas 2-1 to 2-3, [ka] [ka] [ka] In each of the chemical formulas 2-1 to 2-3, n is an integer between 0 and 2, n1 is 0 or 1, R1 is selected from the group consisting of hydrogen, deuterium, unsubstituted or deuterium-substituted C1-C20 alkyl groups, i) each of Y1-Y4 is independently CR2 or N, or ii) one of Y1-Y4 is N and the rest are CR2, one of R3-1-R3-4 is a bonding site, and each of R2 and the remaining R3-1-R3-4 is independently hydrogen, an unsubstituted or deuterium-substituted C1-C20 alkyl group, substituted or unsubstituted Selected from the group consisting of substituted C6-C30 aryl groups, where each of X1, X2, X3, and X4 is independently CR4 or N, and R4 is hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted Selected from the group consisting of substituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups, where X5, X6, X7, and X8 are independently CR5 or N, two of which are CR5, and R5 is either a binding site or hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or This is selected from the group consisting of unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups. In Chemical Formula 2-1, each of R7-2, R7-3, R7-6, and R7-7 is independently selected from the group consisting of hydrogen, deuterium, a C1-C5 alkyl group which is unsubstituted or substituted with deuterium, and a substituted or unsubstituted C6-C30 aryl group. In Chemical Formula 2-2, each of R8-1 and R8-2 is independently selected from the group consisting of hydrogen or a C1-C20 alkyl group which is unsubstituted or substituted with deuterium, or they can be bonded to each other to form an aromatic ring. R8-5 is selected from the group consisting of hydrogen or a C1-C20 alkyl group which is unsubstituted or substituted with deuterium. R8-7 is selected from the group consisting of hydrogen or a C1-C20 alkyl group which is unsubstituted or substituted with deuterium, and a C6-C30 aryl group which is unsubstituted or substituted with at least one of a C1-C20 alkyl group and a C1-C20 alkyl group hydrogenated with deuterium. In Chemical Formula 2-3, each of R9-1 and R9-3 is independently selected from the group consisting of hydrogen or a C1-C20 alkyl group which is unsubstituted or substituted with deuterium, which is characterized.

[0009] In one embodiment of the present invention, the Chemical Formula above is represented by one of the following Chemical Formulas 2-4 to 2-6.

Chemical Formula

Chemical Formula

Chemical Formula

[0010] In another embodiment, the present invention provides an organic light-emitting diode comprising a first electrode, a second electrode facing the first electrode, and a first light-emitting unit located between the first electrode and the second electrode and including a first light-emitting material layer, wherein the first light-emitting material layer includes the organometallic compound described above.

[0011] In the organic light-emitting diode of the present invention, the first light-emitting material layer comprises a first host and a first dopant, wherein the first dopant is the organometallic compound.

[0012] The organic light-emitting diode of the present invention is characterized by further comprising a second light-emitting material layer, a second light-emitting unit located between the first light-emitting unit and the first electrode, and a first charge generation layer located between the first light-emitting unit and the second light-emitting unit.

[0013] The present invention relates to an organic light-emitting diode in which the second light-emitting material layer contains a blue dopant.

[0014] The organic light-emitting diode of the present invention is characterized in that the first light-emitting unit further includes a third light-emitting material layer located below or above the first light-emitting material layer.

[0015] In the organic light-emitting diode of the present invention, the third light-emitting material layer is characterized by containing a red dopant.

[0016] The organic light-emitting diode of the present invention is characterized by further comprising a third light-emitting unit located between the first light-emitting unit and the second electrode and including a third light-emitting material layer, and a second charge generation layer located between the first light-emitting unit and the third light-emitting unit.

[0017] In the organic light-emitting diode of the present invention, the third light-emitting material layer is characterized by containing a red dopant.

[0018] The organic light-emitting diode of the present invention further comprises a third light-emitting unit located between the first light-emitting unit and the second electrode and including a third light-emitting material layer, and a second charge generation layer located between the first light-emitting unit and the third light-emitting unit, wherein the first light-emitting unit further comprises a fourth light-emitting material layer located below or above the first light-emitting material layer.

[0019] The present invention relates to an organic light-emitting diode characterized in that the third light-emitting material layer contains a blue dopant, and the fourth light-emitting material layer contains a green dopant.

[0020] In yet another embodiment, the present invention provides an organic light-emitting device comprising: a substrate; an organic light-emitting diode comprising: a substrate; a first electrode located on the upper part of the substrate and facing the first electrode; a first light-emitting unit located between the first electrode and the second electrode and comprising a first light-emitting material layer; and a thin-film transistor located between the substrate and the organic light-emitting diode and connected to the organic light-emitting diode, wherein the first light-emitting material layer comprises the organometallic compound described above. [Effects of the Invention]

[0021] The organometallic compound of the present invention is an iridium complex having a specific structure (chemical formula 1), exhibiting excellent luminescence properties, improved luminescence efficiency, and increased lifespan due to stable photophysical characteristics. Therefore, the luminescence efficiency and lifespan of organic light-emitting diodes and organic light-emitting devices containing the organometallic compound are improved, and low-power operation is possible.

[0022] Furthermore, the organic light-emitting diode of the present invention comprises a first green light-emitting unit containing a first green light-emitting material layer and a second green light-emitting unit containing a second green light-emitting material layer, and has a multi-stack structure, wherein at least one of the first and second green light-emitting material layers contains the organometallic compound of the present invention, which is an iridium complex having a specific structure (chemical formula 1). Therefore, the luminous efficiency and lifespan are improved in the organic light-emitting diode of the present invention and the organic light-emitting device containing the same.

[0023] Furthermore, the organic light-emitting diode of the present invention includes a first red light-emitting unit containing a first red light-emitting material layer and a second red light-emitting unit containing a second red light-emitting material layer, and has a multi-stack structure, wherein at least one of the first and second red light-emitting material layers contains the organometallic compound of the present invention, which is an iridium complex having a specific structure (chemical formula 1). Therefore, the luminous efficiency and lifespan are improved in the organic light-emitting diode of the present invention and the organic light-emitting device containing the same.

[0024] Furthermore, the present invention provides a white organic light-emitting diode with a multi-stack structure including a red light-emitting material layer and a green light-emitting material layer, wherein at least one of the red light-emitting material layer and the green light-emitting material layer contains the organometallic compound of the present invention, which is an iridium complex having a specific structure (chemical formula 1). Therefore, in the organic light-emitting diode of the present invention and the organic light-emitting device containing the same, the driving voltage is reduced, and the luminous efficiency and lifespan are improved. [Brief explanation of the drawing]

[0025] [Figure 1] Figure 1 is a schematic circuit diagram of the organic light-emitting display device according to the present invention. [Figure 2] Figure 2 is a schematic cross-sectional view of an organic light-emitting display device according to a first embodiment of the present invention. [Figure 3] Figure 3 is a schematic cross-sectional view of an organic light-emitting diode according to a second embodiment of the present invention. [Figure 4] Figure 4 is a schematic cross-sectional view of an organic light-emitting diode according to a third embodiment of the present invention. [Figure 5] Figure 5 is a schematic cross-sectional view of an organic light-emitting display device according to a fourth embodiment of the present invention. [Figure 6] Figure 6 is a schematic cross-sectional view of an organic light-emitting diode according to a fifth embodiment of the present invention. [Figure 7] Figure 7 is a schematic cross-sectional view of an organic light-emitting diode according to a sixth embodiment of the present invention. [Figure 8] Figure 8 is a schematic cross-sectional view of an organic light-emitting diode according to the seventh embodiment of the present invention. [Modes for carrying out the invention]

[0026] The advantages and features of the present invention, and the methods for achieving them, will become clearer with reference to the embodiments described below in detail with the accompanying drawings. However, the present invention is not limited to the embodiments disclosed below and may consist of a variety of different forms, provided that these embodiments complete the disclosure of the present invention and fully inform those skilled in the art of the invention of its scope, and the present invention is defined solely by the claims.

[0027] The shapes, sizes, proportions, angles, numbers, etc. disclosed in the drawings illustrating embodiments of the present invention are illustrative, and the present invention is not limited to those shown. Throughout the specification, the same reference numerals refer to the same components.

[0028] Furthermore, in describing the present invention, if it is determined that a specific explanation of related prior art may unnecessarily obscure the gist of the invention, such detailed explanation will be omitted. Wherever "includes," "has," "becomes," etc., are used as described herein, other parts may be added unless "only" is used. When a component is expressed singly, it includes cases where multiple components are included unless otherwise explicitly stated.

[0029] In interpreting the constituent elements, they shall be interpreted as including a margin of error, even if not explicitly stated otherwise.

[0030] When describing spatial relationships, for example, if the relationship between two parts is described using phrases like "on top," "above," "below," or "beside," then, unless "immediately" or "directly" is used, it is permissible for one or more other parts to be located between the two parts.

[0031] When describing temporal relationships, for example, when a temporal sequence is described using phrases like "after," "following," "next," or "before," it can include cases that are not continuous unless "immediately" or "directly" is used.

[0032] While terms such as "first," "second," etc., are used to describe various components, these components are not limited by these terms. These terms are simply used to distinguish one component from another. Therefore, the first component mentioned below may be the second component within the technical concept of the present invention.

[0033] Each of the various embodiments of the present invention is partially or entirely combinable or combined with one another, enabling a variety of technically diverse interlocking and driving processes. Each embodiment may be implemented independently of the others or in correlation with one another.

[0034] Preferred embodiments of the present invention will be described below with reference to the drawings. The organometallic compound according to the present invention has improved luminescence efficiency and luminescence lifetime. The organometallic compound according to the present invention is represented by the following chemical formula 1. [ka] In chemical formula 1, n is an integer between 0 and 2, and each of Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 is independently C, CR2, or N, and one of Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 is C. R1 is selected from the group consisting of hydrogen, deuterium, and substituted or unsubstituted C1-C20 alkyl groups, and R2 is selected from the group consisting of hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, and substituted or unsubstituted C Selected from the group consisting of 2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, acyl groups, carbonyl groups, carboxylate groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, and phosphino groups, X and Y are independently selected from C, N, and O. The W ring has one of the structures shown in chemical formula 1a-1, chemical formula 1a-2, or chemical formula 1a-3. [ka] [ka] [ka] In chemical formulas 1a-1 and 1a-2, X1, X2, X3, and X4 are independently CR4 or N, and R4 is hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C1-C20 alkylamino group, or substituted or unsubstituted C1-C20 a Selected from the group consisting of a lucylsilyl group, a substituted or unsubstituted C6-C30 allyloxy group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C6-C30 arylsilyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group, In chemical formula 1a-2, X5, X6, X7, and X8 are independently CR5 or N, with at least two of them being CR5, and R5 being either a bonding site or hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, or substituted or unsubstituted C6-C30 ali groups. Selected from the group consisting of a luoxy group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C6-C30 arylsilyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, an acyl group, a carbonyl group, a carboxylate group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group. In chemical formula 1a-3, X9 is O or S, a1 is an integer from 0 to 4, and R6 is deuterium, halide, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C1-C20 alkylamino group, substituted or unsubstituted C1-C20 alkylsilyl group, substituted or unsubstituted C2-C20 alkenyl group, substituted or unsubstituted C2-C20 The group is selected from the group consisting of alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, acyl groups, carbonyl groups, carboxylate groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, and phosphino groups.

[0035] In the chemical formulas described in the specification of this invention, the asterisk (*) indicates a bonding site. For example, in chemical formula 1a-1, the portion indicated by the asterisk (*) is bonded to the iridium and pyridine in chemical formula 1.

[0036] For example, when an alkyl group, alkoxy group, cycloalkyl group, alkylamino group, alkylsilyl group, alkenyl group, alkynyl group, arylamino group, arylsilyl group, aryloxy group, aryl group, or heteroaryl group is substituted, the substituent can be selected from deuterium, halogen, cyano group, carboxyl group, carbonyl group, amine group, alkylamine group, nitro group, hydrazyl group, sulfonic acid group, unsubstituted alkyl group or alkyl group substituted with at least one of deuterium and halogen, unsubstituted alkoxy group or alkylsilyl group substituted with at least one of deuterium and halogen, unsubstituted cycloalkylsilyl group or alkylsilyl group substituted with at least one of deuterium and halogen, unsubstituted arylsilyl group or alkyl group substituted with at least one of deuterium and halogen, or unsubstituted heteroaryl group substituted with at least one of deuterium and halogen.

[0037] In the present invention, unless otherwise stated, alkyl groups may include linear alkyl groups and branched alkyl groups. For example, alkyl groups can be selected from the group consisting of methyl, ethyl, propyl, butyl, and tert-butyl.

[0038] In the present invention, unless otherwise stated, the ring formed by the bonding of two adjacent substituents may be one of the following: a substituted or unsubstituted C3-C30 alicyclic ring, a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C3-C30 aromatic heterocycle.

[0039] In the present invention, unless otherwise stated, the C6-C30 aryl group can be selected from the group consisting of phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, pentarenyl group, indenyl group, indenoindenyl group, heptarenyl group, biphenylenyl group, indacenyl group, phenalenyl group, phenantrenyl group, benzophenantrenyl group, dibenzophenantrenyl group, azulenyl group, pyrenyl group, fluoranthenyl group, triphenylenyl group, chrysenyl group, tetraphenyl group, tetracenyl group, pleiadenyl group, picenyl group, pentaphenyl group, pentacenyl group, fluorenyl group, indenofluorenyl group, and spirofluorenyl group.

[0040] Furthermore, in the present invention, unless otherwise stated, C3-C30 heteroaryl groups are pyrrolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridadinyl group, triazinyl group, tetradinyl group, imidazolyl group, pyrazolyl group, indolyl group, isoindolyl group, indazolyl group, indolidinyl group, pyrrolidinyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, indenocarbazolyl group, benzoflocarbazolyl group, benzothienocarbazolyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cinolinyl group, quinazolinyl group, quinozolinyl group, quinolidinyl group, prinyl group, phthalazinyl group, quinoxalinyl group, benzoquinolinyl group, benzoisoquinolinyl group, You can choose from the group consisting of benzoquinazolinyl group, benzoquinoxalinyl group, acridinyl group, phenanthrolinyl group, perimidinyl group, phenanthrezinyl group, pteridinyl group, synnolinyl group, naphthalidinyl group, furanyl group, pyranyl group, oxazinyl group, oxazolyl group, oxadiazolyl group, triazolyl group, dioxynyl group, benzofuranyl group, dibenzofuranyl group, thiopyranyl group, xanthenyl group, clomenyl group, isoclomenyl group, thioazinyl group, thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, difluoropyradinyl group, benzoflodifronyl group, benzothienobenzothiophenyl group, benzothienodibenzothiophenyl group, benzothienobenzofuranyl group, and benzothienodibenzofuranyl group.

[0041] In one embodiment of the present invention, one of Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 may be C, and the rest may be CR2.

[0042] In one embodiment of the present invention, one of Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 is C, one of the other Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 is N, and the rest may be CR2.

[0043] In chemical formula 1, the ring containing Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8 is linked to the pyridine ring via one of the carbon atoms Z1, Z2, Z3, Z4, Z5, Z6, Z7, and Z8.

[0044] In one embodiment of the present invention, R1 may be an unsubstituted or deuterium-substituted C1-C20 alkyl group. For example, R1 may be methyl, tert-butyl, or CD3.

[0045] In one embodiment of the present invention, R2 can be selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl groups, and substituted or unsubstituted C6-C30 aryl groups. For example, R2 can be selected from hydrogen, unsubstituted or deuterium-substituted C1-C20 alkyl groups (e.g., methyl or tert-butyl), and unsubstituted or C6-C30 aryl groups substituted with at least one of methyl, tert-butyl, or CD3 (e.g., phenyl).

[0046] In one embodiment of the present invention, the auxiliary ligand "XY" can be represented by one of the chemical formulas 1b-1, 1b-2, and 1b-3. [ka] [ka] [ka] In chemical formula 1b-1, each of R7-1, R7-2, R7-3, R7-4, R7-5, R7-6, R7-7, and R7-8 is independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1-C5 alkyl groups, or substituted or unsubstituted C6-C30 aryl groups, or two adjacent R7-1, R7-2, R7-3, and R7-4, or two adjacent R7-5, R7-6, R7-7, and R7-8, are bonded to each other to form a ring.

[0047] In chemical formula 1b-2, each of R8-1, R8-2, R8-3, R8-4, R8-5, and R8-6 is independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1-C5 alkyl groups, or substituted or unsubstituted C6-C30 aryl groups, or two adjacent R8-1, R8-2, R8-3, R8-4, R8-5, and R8-6 are bonded to each other to form a ring, and R8-7 is hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, or substituted or unsubstituted C1-C20 alkyl aryl groups. The group is selected from the group consisting of no groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, acyl groups, carbonyl groups, carboxylate groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, and phosphino groups.

[0048] In chemical formula 1b-3, each of R9-1, R9-2, and R9-3 is independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1-C5 alkyl groups, or substituted or unsubstituted C6-C30 aryl groups, or two adjacent R9-1, R9-2, and R9-3 are bonded to each other to form a ring.

[0049] In one embodiment of the present invention, "XY" in chemical formula 1 is represented by chemical formula 1b-1, and each of R7-1, R7-2, R7-3, R7-4, R7-5, R7-6, R7-7, and R7-8 can be independently selected from the group consisting of hydrogen, methyl, CD3, tert-butyl, unsubstituted, or phenyl groups substituted with methyl or CD3.

[0050] In one embodiment of the present invention, "XY" in chemical formula 1 is represented by chemical formula 1b-2, and i) each of R8-1, R8-2, R8-3, R8-4, R8-5, and R8-6 is independently selected from the group consisting of hydrogen, methyl, and CD3, or ii) each of R8-3, R8-4, R8-5, and R8-6 is independently selected from the group consisting of hydrogen, methyl, and CD3, and R8-1 and R8-2 can bond to each other to form a benzene ring.

[0051] In one embodiment of the present invention, "XY" in chemical formula 1 is represented by chemical formula 1b-2, and R8-7 can be selected from the group consisting of methyl, CD3, unsubstituted, or deuterium-substituted tert-butyl groups.

[0052] In one embodiment of the present invention, "XY" in chemical formula 1 is represented by chemical formula 1b-3, and each of R9-1, R9-2, and R9-3 can be independently selected from the group consisting of hydrogen, methyl, tert-butyl, and pentyl.

[0053] In one embodiment of the present invention, in chemical formula 1a-1 which is a W ring, i) all of X1, X2, X3, and X4 may be CR4, or ii) one of X1, X2, X3, and X4 may be N and the rest may be CR4. In this case, R4 can be selected from the group consisting of hydrogen, methyl, CD3, and phenyl.

[0054] In one embodiment of the present invention, in the W ring of chemical formula 1a-2, i) all of X1, X2, X3, and X4 may be CR4, or ii) one of X1, X2, X3, and X4 may be N and the rest may be CR4. Alternatively, i) all of X5, X6, X7, and X8 may be CR5, or ii) one of X5, X6, X7, and X8 may be N and the rest may be CR5. In this case, R4 and R5 can be independently selected from the group consisting of hydrogen, methyl, CD3, tert-butyl, methyl, CD3, and tert-butyl-substituted phenyl compounds.

[0055] In one embodiment of the present invention, in chemical formula 1a-3, which is a W ring, R6 may be methyl or CD3.

[0056] In one embodiment of the present invention, the W ring can be selected from chemical formulas 1a-4. [ka] [ka] [ka] [ka] [ka]

[0057] In chemical formula 1a-4, R4 is selected from the group consisting of deuterium, unsubstituted or deuterium-substituted C1-C20 alkyl groups.

[0058] As mentioned above, in chemical formula 1, the W ring has one of the structures shown in chemical formula 1a-1, chemical formula 1a-2, or chemical formula 1a-3, and the auxiliary ligand "XY" can be represented by one of chemical formulas 1b-1, 1b-2, or 1b-3. For example, the organometallic compound of chemical formula 1 can be represented by one of chemical formulas 1c-1 to 1c-9. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0059] In each of the chemical formulas 1c-1 to 1c-9, Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, n, R1, and R2 are the same as those defined in chemical formula 1; X1, X2, X3, X4, X5, X6, X7, X8, R4, R5, X9, a1, and R6 are the same as those defined in chemical formulas 1a-1 to 1a-3; and R7-1, R7-2, R7-3, R7-4, R7-5, R7-6, R7-7, R7-8, R8-1, R8-2, R8-3, R8-4, R8-5, R8-6, R8-7, R9-1, R9-2, and R9-3 are the same as those defined in chemical formulas 1b-1 to 1b-3.

[0060] In one embodiment of the present invention, i) all of Z1 to Z8 in chemical formula 1 may be carbon, or ii) one of Z1 to Z8 in chemical formula 1 may be nitrogen and the rest may be carbon. Furthermore, the auxiliary ligand "XY" structure can be identified. For example, the organometallic compound of chemical formula 1 may be represented by one of chemical formulas 2-1 to 2-3. [ka] [ka] [ka]

[0061] In each of the chemical formulas 2-1 to 2-3, n is an integer from 0 to 2, n1 is 0 or 1, R1 is selected from the group consisting of hydrogen, deuterium, unsubstituted or deuterium-substituted C1-C20 alkyl groups, i) each of Y1-Y4 is independently CR2 or N, or ii) one of Y1-Y4 is N and the rest are CR2, one of R3-1 to R3-4 is a bonding site, R2 and the remaining R3-1 to R3-4 are independently selected from the group consisting of hydrogen, unsubstituted or deuterium-substituted C1-C20 alkyl groups, and substituted or unsubstituted C6-C30 aryl groups, X1, X2, X3, and X4 are independently CR4 or N, and R4 is Selected from the group consisting of hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups, Each of X5, X6, X7, and X8 is independently either CR5 or N, two of which are CR5, and R5 is either a binding site or selected from the group consisting of hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C3-C30 heteroaryl groups.

[0062] In chemical formula 2-1, R7-2, R7-3, R7-6, and R7-7 are each independently selected from the group consisting of hydrogen, deuterium, unsubstituted or deuterium-substituted C1-C5 alkyl groups, and substituted or unsubstituted C6-C30 aryl groups.

[0063] In chemical formula 2-2, R8-1 and R8-2 are independently selected from the group consisting of hydrogen or unsubstituted or deuterium-substituted C1-C20 alkyl groups, or can be bonded to each other to form an aromatic ring; R8-5 is selected from the group consisting of hydrogen or unsubstituted or deuterium-substituted C1-C20 alkyl groups; and R8-7 is selected from the group consisting of hydrogen or unsubstituted or deuterium-substituted C1-C20 alkyl groups, or C6-C30 aryl groups substituted with at least one of an unsubstituted or C1-C20 alkyl group and a deuterated C1-C20 alkyl group.

[0064] In chemical formula 2-3, R9-1 and R9-3 are independently selected from the group consisting of hydrogen or unsubstituted or deuterium-substituted C1-C20 alkyl groups.

[0065] In one embodiment of the present invention, R1 may be an unsubstituted or deuterium-substituted C1-C20 alkyl group (for example, methyl or CD3).

[0066] In one embodiment of the present invention, all of the multiple R2s may be hydrogen.

[0067] In one embodiment of the present invention, one of the plurality of R2 is an unsubstituted or deuterium-substituted C1-C20 alkyl group (e.g., methyl, tert-butyl, or CD3) or a C6-C30 aryl group (e.g., phenyl) substituted with at least one of an unsubstituted or C1-C20 alkyl group (e.g., methyl or tert-butyl) and a deuterium-substituted alkyl group (e.g., CD3), and the remainder may be hydrogen.

[0068] In one embodiment of the present invention, n1 is 0, one of X1, X2, X3, and X4 is N, and the rest may be CR4.

[0069] In one embodiment of the present invention, n1 is 0, and X1, X2, X3, and X4 may all be CR4.

[0070] In one embodiment of the present invention, n1 is 1, one of X1, X2, X3, and X4 is N, the rest are CR4, and X5, X6, X7, and X8 may all be CR5.

[0071] In this case, R4 and R5 can be independently selected from hydrogen, methyl, unsubstituted, or deuterium-substituted C1-C20 alkyl groups (e.g., methyl or CD3).

[0072] In one embodiment of the present invention, R7-2, R7-3, and R7-7 can each be independently selected from unsubstituted or deuterium-substituted C1-C20 alkyl groups (e.g., methyl or CD3).

[0073] In one embodiment of the present invention, each of R7-6 can be selected from the group consisting of hydrogen, substituted or unsubstituted C6-C30 aryl groups (e.g., phenyl).

[0074] In one embodiment of the present invention, i) in chemical formula 1, all of Z1 to Z8 may be carbon, or ii) in chemical formula 1, one of Z1 to Z8 may be nitrogen and the rest may be carbon. Furthermore, the bonding position of the Z1 to Z8-containing ring and the substituent positions of the Z1 to Z8-containing ring can be identified. In addition, the auxiliary ligand "XY" structure can be identified. For example, the organometallic compound of chemical formula 1 may be represented by one of chemical formulas 2-4 to 2-6. [ka] [ka] [ka] In each of the chemical formulas 2-4 to 2-6, n is an integer from 0 to 2, n1 is 0 or 1, X10 is CR10 or N, R1 is selected from the group consisting of hydrogen, deuterium, unsubstituted or deuterium-substituted C1-C20 alkyl groups, R2-1, R2-2, and R10 are each independently selected from the group consisting of hydrogen, deuterium, unsubstituted or deuterium-substituted C1-C20 alkyl groups, and substituted or unsubstituted C6-C30 aryl groups, and X1, X2, X3, and X4 are each independently selected from the group consisting of CR4 R4 is N, and R4 is hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C1-C20 alkylamino group, substituted or unsubstituted C1-C20 alkylsilyl group, substituted or unsubstituted C6-C30 allyloxy group, substituted or unsubstituted C2-C20 alkenyl group, substituted or unsubstituted C2-C20 alkynyl group, substituted or unsubstituted C6-C30 allyl X5, X6, X7, and X8 are each independently CR5 or N, of which two are CR5, and R5 is either a binding site or hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, or substituted or unsubstituted C3-C30 cycloalkyl groups. Selected from the group consisting of a C1-C20 alkylamino group, a C1-C20 alkylsilyl group, a C6-C30 allyloxy group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C30 arylamino group, a C6-C30 arylsilyl group, a C6-C30 aryl group, or a C3-C30 heteroaryl group.

[0075] In chemical formula 2-4, R7-2, R7-3, R7-6, and R7-7 are each independently selected from the group consisting of hydrogen, deuterium, unsubstituted or deuterium-substituted C1-C5 alkyl groups, and substituted or unsubstituted C6-C30 aryl groups.

[0076] In chemical formula 2-5, R8-1 and R8-2 are independently selected from the group consisting of hydrogen or unsubstituted or deuterium-substituted C1-C20 alkyl groups, or they can bond to each other to form an aromatic ring. R8-5 is selected from the group consisting of hydrogen or unsubstituted or deuterium-substituted C1-C20 alkyl groups, and R8-7 is selected from the group consisting of hydrogen or unsubstituted or deuterium-substituted C1-C20 alkyl groups, or C6-C30 aryl groups substituted with at least one of an unsubstituted or C1-C20 alkyl group and a deuterated C1-C20 alkyl group.

[0077] In chemical formula 2-6, R9-1 and R9-3 are independently selected from the group consisting of hydrogen or unsubstituted or deuterium-substituted C1-C20 alkyl groups.

[0078] In one embodiment of the present invention, R1 may be an unsubstituted or deuterium-substituted C1-C20 alkyl group (for example, methyl or CD3).

[0079] In one embodiment of the present invention, R2-1 may be an unsubstituted or deuterium-substituted C1-C20 alkyl group (for example, methyl or CD3).

[0080] In one embodiment of the present invention, R2-2 may be a C1-C20 alkyl group (e.g., methyl, tert-butyl, or CD3) substituted with hydrogen, an unsubstituted, or deuterium-substituted group, or a C6-C30 aryl group (e.g., phenyl) substituted with at least one of an unsubstituted or C1-C20 alkyl group (e.g., methyl or tert-butyl) and a deuterium-substituted alkyl group (e.g., CD3).

[0081] In one embodiment of the present invention, n1 is 0, one of X1, X2, X3, and X4 is N, and the rest may be CR4.

[0082] In one embodiment of the present invention, n1 is 0, and X1, X2, X3, and X4 may all be CR4.

[0083] In one embodiment of the present invention, n1 is 1, one of X1, X2, X3, and X4 is N, the rest are CR4, and X5, X6, X7, and X8 may all be CR5.

[0084] In this case, R4 and R5 can be independently selected from hydrogen, methyl, unsubstituted, or deuterium-substituted C1-C20 alkyl groups (e.g., methyl or CD3).

[0085] In one embodiment of the present invention, R7-2, R7-3, and R7-7 can each be independently selected from unsubstituted or deuterium-substituted C1-C20 alkyl groups (e.g., methyl or CD3).

[0086] In one embodiment of the present invention, each of R7-6 can be selected from the group consisting of hydrogen, substituted or unsubstituted C6-C30 aryl groups (e.g., phenyl).

[0087] In one embodiment of the present invention, R8-1 and R8-2 can independently be hydrogen atoms or bond with each other to form an aromatic ring.

[0088] In one embodiment of the present invention, R8-5 may be an unsubstituted or deuterium-substituted C1-C20 alkyl group (for example, methyl or CD3).

[0089] In one embodiment of the present invention, R8-7 can be selected from the group consisting of hydrogen or a C6-C30 aryl group (e.g., phenyl) substituted with one of an unsubstituted or C1-C20 alkyl group (e.g., methyl) and a deuterated C1-C20 alkyl group (e.g., CH2D).

[0090] In one embodiment of the present invention, R9-1 and R9-3 can each be independently selected from C1-C20 alkyl groups (e.g., methyl, tert-butyl, or pentyl).

[0091] In one embodiment of the present invention, in chemical formula 2, n is 2, n1 is 0, X10, X1 to X4 are CH, R1 and R2-1 are independently unsubstituted or deuterium-substituted C1 to C20 alkyl groups (e.g., CH3 or CD3), and R2-2 may be a substituted or unsubstituted C6 to C30 aryl group (e.g., phenyl).

[0092] In one embodiment of the present invention, n is 2, n1 is 0, X10 and X1 are N, X2 is CR4 (R4 = CH3 or CD3), X3 and X4 are CH, and R1, R2-1, and R2-2 may each be an unsubstituted or deuterium-substituted C1-C20 alkyl group (e.g., CH3 or CD3).

[0093] In one embodiment of the present invention, the organometallic compound is a compound represented by chemical formula 2-4, where n is 1 or 2, n1 is 0 or 1, X10 is CR10 or N; R1 is selected from hydrogen, deuterium, unsubstituted or deuterium-substituted C1-C20 alkyl groups, R2-1, R2-2, and R10 are each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, and propyl; one of X1-X4 is N, and the rest are CR4, where R4 is hydrogen, deuterium, halide, or substituted or unsubstituted C1-C20 alkyl groups substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted Selected from the group consisting of C3-C30 heteroaryl groups, each of X5-X8 is independently CR5 or N, of which two are CR5, and R5 is either a binding site or hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, substituted or unsubstituted R7-2, R7-3, R7-6, and R7-7 can each be independently selected from the group consisting of hydrogen, deuterium, unsubstituted or deuterium-substituted C1-C5 alkyl groups, or substituted or unsubstituted C6-C30 aryl groups.

[0094] In one embodiment of the present invention, the organometallic compound is a compound represented by chemical formula 2-5, where n is 1 or 2, n1 is 0 or 1, X10 is CR10 or N, R1 is selected from hydrogen, deuterium, unsubstituted or deuterium-substituted C1-C20 alkyl groups, R2-1, R2-2, and R10 are each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, and propyl, one of X1-X4 is N, and the rest are CR4, where R4 is hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3- Selected from the group consisting of C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups, where each of X5-X8 is independently CR5 or N, and two of these are CR5;R5 is either a binding site, or hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted Alternatively, R8-1 and R8-2 may be selected from the group consisting of unsubstituted C3-C30 heteroaryl groups, and each of them may be independently selected from the group consisting of hydrogen or unsubstituted or deuterium-substituted C1-C20 alkyl groups, or they may be bonded to each other to form an aromatic ring; R8-5 may be selected from the group consisting of hydrogen or unsubstituted or deuterium-substituted C1-C20 alkyl groups; and R8-7 may be selected from the group consisting of hydrogen or unsubstituted or deuterium-substituted C1-C20 alkyl groups, or C6-C30 aryl groups substituted with at least one of an unsubstituted or C1-C20 alkyl group and a deuterated C1-C20 alkyl group.

[0095] In one embodiment of the present invention, the organometallic compound is a compound represented by chemical formula 2-6, where n is 1 or 2, n1 is 0 or 1, X10 is CR10 or N, R1 is selected from hydrogen, deuterium, unsubstituted or deuterium-substituted C1-C20 alkyl groups, R2-1, R2-2, and R10 are each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, and propyl, one of X1-X4 is N and the rest are CR4, and R4 is hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups 20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 allyloxy groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C Selected from the group consisting of 30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups, where each of X5-X8 is independently CR5 or N, of which two are CR5, and R5 is either a binding site or hydrogen, deuterium, halide, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C1-C20 alkylamino groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted R9-1 and R9-3 can each be independently selected from the group consisting of substituted C6-C30 allyloxy groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C2-C20 alkynyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups.

[0096] In one embodiment of the present invention, the organometallic compound of chemical formula 1 may be one of the compounds of chemical formula 3. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0097] Organometallic compounds having the structure of chemical formula 1 have a main ligand formed by the condensation of numerous aromatic rings and aromatic heterocycles. This results in a narrow full-width at half maximum (FWHM) in the emission spectrum. In particular, because they have a robust chemical structure, the rotation of the chemical structure is not freely controlled during the emission process, allowing for the stable maintenance of a good emission lifetime. Since the emission of excitons can restrict the emission spectrum of the organometallic compounds according to the present invention to a specific range, the color purity is improved.

[0098] Furthermore, the organometallic compounds of the present invention may be heterolytic metal complex compounds in which different primary and auxiliary ligands bind to a central metal (iridium). Therefore, the emission color purity and emission wavelength range can be easily adjusted.

[0099] Organometallic compounds having the structure of chemical formula 1 may have emission wavelengths ranging from green to red. For example, an organometallic compound having the structure of chemical formula 1 can be used as at least one of a green dopant, a yellow-green dopant, and a red dopant.

[0100] The organometallic compound of the present invention, which is represented by one of chemical formulas 1 or 2 and selected from the compounds of chemical formula 3, emits light with wavelengths ranging from green to red, and is used in the light-emitting material layer of an organic light-emitting diode, thereby improving the luminous efficiency and lifespan of the organic light-emitting diode.

[0101] [Example of combination] 1. Synthesis of intermediate A (1) Intermediate A-2 [ka] A mixture of SM_A (13.0 g, 70.0 mmol), 4-bromo-2-chloro-5-methylpyridine (16.5 g, 80.0 mmol), Pd(PPh3)4 (2.3 g, 2.0 mmol), and calcium carbonate (22.1 g, 160.0 mmol) was added to a solvent (500 ml) of tetrahydrofuran and water, and refluxed overnight. After removing the unpurified solvent mixture, 14.2 g (76%, 53.2 mmol) of substance A-2 was obtained by silica gel column chromatography.

[0102] (2) Intermediate A-1 [ka] A mixture of compound SM_B (15.5 g, 50.0 mmol), intermediate A-2 (13.9 g, 52.0 mmol), Pd(PPh3)4 (1.2 g, 1.0 mmol), and sodium carbonate (15.9 g, 150.0 mmol) was added to a solvent (500 ml) of toluene, ethanol, and water, and refluxed overnight. After removing the unpurified solvent mixture, 13.8 g (64%, 33.3 mmol) of substance A-1 was obtained by silica gel column chromatography.

[0103] (3) Intermediate A [ka] A mixture of intermediate A-1 (12.4 g, 30.0 mmol) and sodium ethoxide (13.6 g, 200.0 mmol) was added to DMSO-d6 (300 ml), stirred at 70°C for 48 hours, and then the solvent was removed. After repeating this process, 10.5 g (83%, 24.9 mmol) of intermediate A was obtained by silica gel column chromatography.

[0104] 2. Synthesis of intermediate B (1) Intermediate B-2 [ka] A mixture of compound SM_C (18.3g, 70.0 mmol), 4-bromo-2-chloro-5-methylpyridine (16.5g, 80.0 mmol), Pd(PPh3)4 (2.3g, 2.0 mmol), and calcium carbonate (22.1g, 160.0 mmol) was added to a solvent (600 ml) of tetrahydrofuran and water, and refluxed overnight. After removing the unpurified solvent mixture, 17.3 g (72%, 50.4 mmol) of substance B-2 was obtained by silica gel column chromatography.

[0105] (2) Intermediate B-1 [ka] A mixture of compounds SM_B (13.9g, 45.0 mmol), B-2 (16.7g, 48.5 mmol), Pd(PPh3)4 (1.2g, 1.0 mmol), and sodium carbonate (14.8g, 140.0 mmol) was added to a solvent (500 ml) of toluene, ethanol, and water, and refluxed overnight. After removing the unpurified solvent mixture, 15.7 g (66%, 32.0 mmol) of substance B-1 was obtained by silica gel column chromatography.

[0106] (3) Intermediate B [ka] A solution of intermediate B-1 (14.7 g, 30.0 mmol) and sodium ethoxide (13.6 g, 200.0 mmol) was added to DMSO-d6 (300 ml), stirred at 70°C for 48 hours, and then the solvent was removed. After repeating this process, 12.0 g (80%, 24.0 mmol) of the desired intermediate B was obtained by silica gel column chromatography.

[0107] 3. Synthesis of intermediate C (1) Intermediate C-1 [ka] A mixture of compound SM_D (13.2g, 45.0 mmol), intermediate B-2 (17.2g, 50.0 mmol), Pd(PPh3)4 (1.2g, 1.0 mmol), and sodium carbonate (14.8g, 140.0 mmol) was added to a solvent (500 ml) of toluene, ethanol, and water, and refluxed overnight. After removing the unpurified solvent mixture, 16.6 g (70%, 35.0 mmol) of substance C-1 was obtained by silica gel column chromatography.

[0108] (2) Intermediate C [ka] A solution of intermediate C-1 (14.3 g, 30.0 mmol) and sodium ethoxide (13.6 g, 200.0 mmol) was added to DMSO-d6 (300 ml), stirred at 70°C for 48 hours, and then the solvent was removed. After repeating this process, 11.4 g (79%, 23.7 mmol) of intermediate C was obtained by silica gel column chromatography.

[0109] 4. Synthesis of intermediate D (1) Intermediate D-1 [ka] A mixture of compound SM_E (16.2g, 45.0 mmol), intermediate B-2 (17.2g, 50.0 mmol), Pd(PPh3)4 (1.2g, 1.0 mmol), and sodium carbonate (14.8g, 140.0 mmol) was added to a solvent (500 ml) of toluene, ethanol, and water, and refluxed overnight. After removing the unpurified solvent mixture, 16.5 g (61%, 30.5 mmol) of substance D-1 was obtained by silica gel column chromatography.

[0110] (2) Intermediate D [ka] A solution of intermediate D-1 (15.7 g, 29.0 mmol) and sodium ethoxide (13.3 g, 195.0 mmol) was added to DMSO-d6 (300 ml), stirred at 70°C for 48 hours, and then the solvent was removed. After repeating this process, 11.8 g (74%, 21.5 mmol) of intermediate D was obtained by silica gel column chromatography.

[0111] 5. Synthesis of intermediate E (1) Intermediate E-2 [ka] A mixture of compound SM_E (19.8 g, 70.0 mmol), 4-bromo-2-chloro-5-methylpyridine (16.5 g, 80.0 mmol), Pd(PPh3)4 (2.3 g, 2.0 mmol), and calcium carbonate (22.1 g, 160.0 mmol) was added to a solvent (600 ml) of tetrahydrofuran and water, and refluxed overnight. After removing the unpurified solvent mixture, 12.9 g (65%, 45.5 mmol) of substance E-2 was obtained by silica gel column chromatography.

[0112] (2) Intermediate E-1 [ka] A mixture of compound SM_B (13.9 g, 45.0 mmol), intermediate E-2 (12.4 g, 44.0 mmol), Pd(PPh3)4 (1.2 g, 1.0 mmol), and sodium carbonate (14.8 g, 140.0 mmol) was added to a solvent (500 ml) of toluene, ethanol, and water, and refluxed overnight. After removing the unpurified solvent mixture, 13.0 g (69%, 30.4 mmol) of substance E-1 was obtained by silica gel column chromatography.

[0113] (3) Intermediate E [ka] A solution of intermediate E-1 (12.9 g, 30.0 mmol) and sodium ethoxide (13.6 g, 200.0 mmol) was added to DMSO-d6 (300 ml), stirred at 70°C for 48 hours, and then the solvent was removed. After repeating this process, 9.8 g (74%, 22.2 mmol) of intermediate E was obtained by silica gel column chromatography.

[0114] 6. Synthesis of intermediate FF [ka] A mixture of 100 ml of ethoxyethanol and 30 ml of distilled water was mixed with a solution of compound F (7.3 g, 40.0 mmol) and IrCl3 (4.8 g, 16.0 mmol), and the mixture was stirred under reflux for 24 hours. The temperature was then lowered to room temperature, and the resulting solid was separated by vacuum filtration. After thoroughly washing the filtered solid with water and cold methanol, the vacuum filtration process was repeated several times to obtain 11.3 g (95%, 9.5 mmol) of the intermediate FF.

[0115] 7. Synthesis of intermediate GG [ka] A solution of compound G (7.6 g, 40.0 mmol) and IrCl3 (4.8 g, 16.0 mmol) was added to 100 ml of ethoxyethanol and 30 ml of distilled water, and the mixture was stirred under reflux for 24 hours. The temperature was then lowered to room temperature, and the resulting solid was separated by vacuum filtration. After thoroughly washing the filtered solid with water and cold methanol, the vacuum filtration process was repeated several times to obtain 11.4 g (94%, 9.4 mmol) of intermediate GG.

[0116] 8. Synthesis of intermediate HH [ka] A solution of compound H (7.9 g, 40.0 mmol) and IrCl3 (4.8 g, 16.0 mmol) was added to 100 ml of ethoxyethanol and 30 ml of distilled water, and the mixture was stirred under reflux for 24 hours. The temperature was then lowered to room temperature, and the resulting solid was separated by vacuum filtration. After thoroughly washing the filtered solid with water and cold methanol, the vacuum filtration process was repeated several times to obtain 10.2 g (82%, 8.2 mmol) of the intermediate HH.

[0117] 9. Synthesis of Intermediate II [ka] A solution of compound I (8.3 g, 40 mmol) and IrCl3 (4.8 g, 16.0 mmol) was added to 100 ml of ethoxyethanol and 30 ml of distilled water, and the mixture was stirred under reflux for 24 hours. The temperature was then lowered to room temperature, and the resulting solid was separated by vacuum filtration. After thoroughly washing the filtered solid with water and cold methanol, the vacuum filtration process was repeated several times to obtain 10.6 g (83%, 8.3 mmol) of intermediate II.

[0118] 10. Synthesis of intermediate JJ [ka] A solution of compound J (10.9 g, 40.0 mmol) and IrCl3 (4.8 g, 16.0 mmol) was added to 100 ml of ethoxyethanol and 30 ml of distilled water, and the mixture was stirred under reflux for 24 hours. After that, the temperature was lowered to room temperature, and the resulting solid was separated by vacuum filtration. The solid filtered through the filter was thoroughly washed with water and cold methanol, and the vacuum filtration process was repeated several times to obtain 12.5 g (81%, 8.1 mmol) of the intermediate JJ.

[0119] 11. Synthesis of intermediate KK [ka] A solution of compound K (11.3 g, 40 mmol) and IrCl3 (4.8 g, 16.0 mmol) was added to 100 ml of ethoxyethanol and 30 ml of distilled water, and the mixture was stirred under reflux for 24 hours. The temperature was then lowered to room temperature, and the resulting solid was separated by vacuum filtration. After thoroughly washing the filtered solid with water and cold methanol, the vacuum filtration process was repeated several times to obtain 12.5 g (79%, 7.9 mmol) of the intermediate KK.

[0120] 12. Synthesis of the intermediate FFF [ka] A solution containing compound FF (11.3 g, 9.5 mmol) and silver trifluoromethanesulfonate (6.9 g, 27.0 mmol) was added to dichloromethane (150 ml) and methanol (150 ml) and stirred overnight at room temperature. After the reaction was complete, the solid precipitate was removed by filtration through Celite. The filtrate filtered through the filter was subjected to vacuum filtration several times to obtain 13.9 g (95%, 18.1 mmol) of the intermediate FFF.

[0121] 13. Synthesis of intermediate GGG [ka] A solution containing compound GG (11.4 g, 9.4 mmol) and silver trifluoromethanesulfonate (6.9 g, 27.0 mmol) was added to dichloromethane (150 ml) and methanol (150 ml) and stirred overnight at room temperature. After the reaction was complete, the solid precipitate was removed by filtration through Celite. The filtrate filtered through the filter was subjected to vacuum filtration several times to obtain 13.5 g (92%, 17.3 mmol) of the intermediate GGG.

[0122] 14. Synthesis of intermediate HHH [ka] A solution containing compound HH (10.2 g, 8.2 mmol) and silver trifluoromethanesulfonate (6.9 g, 27.0 mmol) was added to dichloromethane (150 ml) and methanol (150 ml) and stirred overnight at room temperature. After the reaction was complete, the solid precipitate was removed by filtration through Celite. The filtrate filtered through the filter was subjected to vacuum filtration several times to obtain 12.4 g (95%, 15.6 mmol) of the intermediate HHH.

[0123] 15. Synthesis of Intermediate III [ka] A solution obtained by adding compound II (10.6 g, 8.3 mmol) and silver trifluoromethanesulfonate (6.9 g, 27.0 mmol) to dichloromethane (150 ml) and methanol (150 ml) was stirred overnight at room temperature. After completion of the reaction, it was filtered through celite to remove the precipitate in the solid state. The process of filtering the filtrate through the filter under reduced pressure was repeated several times to obtain 12.9 g (95%, 15.8 mmol) of intermediate III.

[0124] 16. Synthesis of Intermediate JJJ

Chemical formula

[0125] <00​​​​​​​​​​​​​​​​​​Intermediate A-1 (4.1 g, 10.0 mmol) and intermediate HHH (9.6 g, 12.0 mmol) were added to a mixed solution of 2-ethoxyethanol (180 ml) and DMF (180 ml), and the mixture was stirred at 135°C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic phase was separated using dichloromethane and distilled water. The water was removed by adding anhydrous magnesium sulfate. The solution obtained by filtration was reduced in pressure, and the residue was purified by silica gel column chromatography to obtain 6.5 g (65%, 6.7 mmol) of iridium compound 238.

[0127] 19. Synthesis of Compound 247 [ka] Intermediate A (4.2 g, 10.0 mmol) and intermediate III (9.8 g, 12.0 mmol) were added to a mixed solution of 2-ethoxyethanol (180 ml) and DMF (180 ml), and the mixture was stirred at 135°C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic phase was separated using dichloromethane and distilled water. The water was removed by adding anhydrous magnesium sulfate. The solution obtained by filtration was reduced in pressure, and the residue was purified by silica gel column chromatography to obtain 6.8 g (67%, 6.7 mmol) of iridium compound 247.

[0128] 20. Synthesis of Compound 310 [ka] Intermediate A-1 (4.1 g, 10.0 mmol) and intermediate JJJ (11.4 g, 12.0 mmol) were added to a mixed solution of 2-ethoxyethanol (180 ml) and DMF (180 ml), and the mixture was stirred at 135°C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic phase was separated using dichloromethane and distilled water. The water was removed by adding anhydrous magnesium sulfate. The solution obtained by filtration was reduced in pressure, and the residue was purified by silica gel column chromatography to obtain 8.0 g (69%, 6.9 mmol) of iridium compound 310.

[0129] 21. Synthesis of Compound 319 [ka] Intermediate A (4.2 g, 10.0 mmol) and intermediate KKK (11.6 g, 12.0 mmol) were added to a mixed solution of 2-ethoxyethanol (180 ml) and DMF (180 ml), and the mixture was stirred at 135°C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic phase was separated using dichloromethane and distilled water. Water was removed by adding anhydrous magnesium sulfate. The solution obtained by filtration was reduced in pressure, and the residue was purified by silica gel column chromatography to obtain 7.5 g (64%, 6.4 mmol) of iridium compound 319.

[0130] 22. Synthesis of Compound 243 [ka] To a mixed solution of 2-ethoxyethanol (180 ml) and DMF (180 ml), intermediate B-1 (4.9 g, 10.0 mmol) and intermediate HHH (9.6 g, 12.0 mmol) were added, and the mixture was stirred at 135 °C for 24 hours. After completion of the reaction, the temperature was lowered to room temperature, and the organic phase was separated using dichloromethane and distilled water. The water was removed by adding anhydrous magnesium sulfate. The residue obtained by concentrating the solution obtained through filtration under reduced pressure was purified by silica gel column chromatography to obtain 7.1 g (66%, 6.6 mmol) of iridium compound 243.

[0131] Synthesis of Compound 252

Chemical Structure

[0132] Synthesis of Compound 315

Chemical Structure

[0133] 25. Synthesis of Compound 324 [ka] Intermediate B (5.0 g, 10.0 mmol) and intermediate KKK (11.6 g, 12.0 mmol) were added to a mixed solution of 2-ethoxyethanol (180 ml) and DMF (180 ml), and the mixture was stirred at 135°C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic phase was separated using dichloromethane and distilled water. The water was removed by adding anhydrous magnesium sulfate. The solution obtained by filtration was reduced in pressure, and the residue was purified by silica gel column chromatography to obtain 8.1 g (65%, 6.5 mmol) of iridium compound 324.

[0134] 26. Synthesis of Compound 580 [ka] Intermediate C-1 (4.8 g, 10.0 mmol) and intermediate FFF (9.2 g, 12.0 mmol) were added to a mixed solution of 2-ethoxyethanol (180 ml) and DMF (180 ml), and the mixture was stirred at 135°C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic phase was separated using dichloromethane and distilled water. The water was removed by adding anhydrous magnesium sulfate. The solution obtained by filtration was reduced in pressure, and the residue was purified by silica gel column chromatography to obtain 6.7 g (65%, 6.5 mmol) of iridium compound 580.

[0135] 27. Synthesis of Compound 589 [ka] Intermediate C (4.8 g, 10.0 mmol) and intermediate GGG (9.4 g, 12.0 mmol) were added to a mixed solution of 2-ethoxyethanol (180 ml) and DMF (180 ml), and the mixture was stirred at 135°C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic phase was separated using dichloromethane and distilled water. Water was removed by adding anhydrous magnesium sulfate. The solution obtained by filtration was reduced in pressure, and the residue was purified by silica gel column chromatography to obtain 6.6 g (63%, 6.3 mmol) of iridium compound 589.

[0136] 28. Synthesis of Compound 582 [ka] Intermediate D-1 (5.4 g, 10.0 mmol) and intermediate FFF (9.2 g, 12.0 mmol) were added to a mixed solution of 2-ethoxyethanol (180 ml) and DMF (180 ml), and the mixture was stirred at 135°C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic phase was separated using dichloromethane and distilled water. Water was removed by adding anhydrous magnesium sulfate. The solution obtained by filtration was reduced in pressure, and the residue was purified by silica gel column chromatography to obtain 7.0 g (64%, 6.4 mmol) of iridium compound 582.

[0137] 29. Synthesis of Compound 591 [ka] Intermediate D (5.5 g, 10.0 mmol) and intermediate GGG (9.4 g, 12.0 mmol) were added to a mixed solution of 2-ethoxyethanol (180 ml) and DMF (180 ml), and the mixture was stirred at 135°C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic phase was separated using dichloromethane and distilled water. The water was removed by adding anhydrous magnesium sulfate. The solution obtained by filtration was reduced in pressure, and the residue was purified by silica gel column chromatography to obtain 6.9 g (62%, 6.2 mmol) of iridium compound 591.

[0138] 30. Synthesis of Compound 546 [ka] Intermediate E-1 (4.3 g, 10.0 mmol) and intermediate FFF (9.2 g, 12.0 mmol) were added to a mixed solution of 2-ethoxyethanol (180 ml) and DMF (180 ml), and the mixture was stirred at 135°C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic phase was separated using dichloromethane and distilled water. Water was removed by adding anhydrous magnesium sulfate. The solution obtained by filtration was reduced in pressure, and the residue was purified by silica gel column chromatography to obtain 6.8 g (69%, 6.9 mmol) of iridium compound 546.

[0139] 31. Synthesis of Compound 555 [ka] Intermediate E (4.4 g, 10.0 mmol) and intermediate GGG (9.4 g, 12.0 mmol) were added to a mixed solution of 2-ethoxyethanol (180 ml) and DMF (180 ml), and the mixture was stirred at 135°C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic phase was separated using dichloromethane and distilled water. The water was removed by adding anhydrous magnesium sulfate. The solution obtained by filtration was reduced in pressure, and the residue was purified by silica gel column chromatography to obtain 7.1 g (70%, 7.0 mmol) of iridium compound 555.

[0140] The present invention relates to an organic light-emitting diode (LED) and an organic light-emitting device containing an organic light-emitting diode, wherein an organometallic compound represented by chemical formula 1 is contained within a light-emitting material layer. For example, the organic light-emitting device may be an organic light-emitting display device or an organic light-emitting illumination device. As an example, the description will focus on an organic light-emitting display device, which is a display device containing the organic light-emitting diode of the present invention.

[0141] Figure 1 is a schematic circuit diagram of the organic light-emitting display device according to the present invention.

[0142] As shown in Figure 1, the organic light-emitting display device has gate wiring GL that intersect with each other and define a pixel region P, as well as data wiring DL and power wiring PL. A switching thin-film transistor Ts, a driving thin-film transistor Td, a storage capacitor Cst, and an organic light-emitting diode D are formed in the pixel region P. The pixel region P may include a red pixel region, a green pixel region, and a blue pixel region.

[0143] The switching thin-film transistor Ts is connected to the gate wiring GL and data wiring DL, while the driving thin-film transistor Td and storage capacitor Cst are connected between the switching thin-film transistor Ts and the power wiring PL. The organic light-emitting diode D is connected to the driving thin-film transistor Td.

[0144] In such an organic light-emitting display device, when a gate signal applied to the gate wiring GL turns on the switching thin-film transistor Ts, the data signal applied to the data wiring DL is applied via the switching thin-film transistor Ts to the gate electrode of the driving thin-film transistor Td and one electrode of the storage capacitor Cst.

[0145] The driving thin-film transistor Td is turned on by a data signal applied to its gate electrode. As a result, a current proportional to the data signal flows from the power wiring PL through the driving thin-film transistor Td to the organic light-emitting diode D, and the organic light-emitting diode D emits light with a brightness proportional to the current flowing through the driving thin-film transistor Td.

[0146] In this process, the storage capacitor Cst is charged with a voltage proportional to the data signal, maintaining a constant voltage at the gate electrode of the drive thin-film transistor Td during one frame.

[0147] Therefore, the organic light-emitting display device can display a desired image.

[0148] Figure 2 is a schematic cross-sectional view of an organic light-emitting display device according to a first embodiment of the present invention.

[0149] As shown in Figure 2, the organic light-emitting display device 100 includes a substrate 110, a thin-film transistor Tr located on the upper part of the substrate 110, and an organic light-emitting diode D located on the planarization layer 150 and connected to the thin-film transistor Tr.

[0150] The substrate 110 may be a glass substrate or a flexible substrate. For example, the substrate 110 may be any one of the following: a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylene naphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, or a polycarbonate (PC) substrate.

[0151] A buffer layer 122 is formed on the substrate 110, and a thin-film transistor Tr is formed on the buffer layer 122. The buffer layer 122 may be omitted.

[0152] A semiconductor layer 120 is formed on top of the buffer layer 122. For example, the semiconductor layer 120 may be made of an oxide semiconductor material. If the semiconductor layer 120 is made of an oxide semiconductor material, a light-shielding pattern (not shown) may be formed on the bottom of the semiconductor layer 120. The light-shielding pattern prevents light from entering the semiconductor layer 120 and prevents the semiconductor layer 120 from degrading due to light. Selectively, the semiconductor layer 120 may be made of polycrystalline silicon, in which case impurities may be doped at both ends of the semiconductor layer.

[0153] A gate insulating film 124 made of an insulating material is formed on the front surface of the substrate 110 above the semiconductor layer 120. The gate insulating film 124 may be made of an inorganic insulating material such as silicon oxide (SiOx) or silicon nitride (SiNx).

[0154] A gate electrode 130, made of a conductive material such as metal, is formed on top of the gate insulating film 124, corresponding to the center of the semiconductor layer 120. In Figure 2, the gate insulating film 122 is formed on the front surface of the substrate 110, but the gate insulating film 122 may be patterned in the same shape as the gate electrode 130.

[0155] An interlayer insulating film 132 made of an insulating material is formed on the front surface of the substrate 110 above the gate electrode 130. The interlayer insulating film 132 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or it may be formed of an organic insulating material such as benzocyclobutene or photo-acrylic.

[0156] The interlayer insulating film 132 has first and second semiconductor layer contact holes 134 and 136 that expose the surfaces on both sides of the semiconductor layer 120. The first and second semiconductor layer contact holes 134 and 136 are located on both sides of the gate electrode 130, spaced apart from the gate electrode 130. In Figure 2, the first and second semiconductor layer contact holes 134 and 136 are formed in the interlayer insulating film 132 and the gate insulating film 122. Alternatively, if the gate insulating film 122 is patterned with the same shape as the gate electrode 130, the first and second semiconductor layer contact holes 134 and 136 may be formed only within the interlayer insulating film 132.

[0157] A source electrode 144 and a drain electrode 146 made of a conductive material such as metal are formed on the upper part of the interlayer insulating film 132. The source electrode 144 and the drain electrode 146 are located spaced apart from the gate electrode 130 and contact both sides of the semiconductor layer 120 via the first and second semiconductor layer contact holes 134 and 136, respectively.

[0158] The semiconductor layer 120, gate electrode 130, source electrode 144, and drain electrode 146 form a thin-film transistor Tr, which functions as a driving element. In other words, the thin-film transistor Tr is the driving thin-film transistor Td in Figure 1.

[0159] In Figure 2, the thin-film transistor Tr has a coplanar structure in which the gate electrode 130, source electrode 144, and drain electrode 146 are located on the upper part of the semiconductor layer 120. Alternatively, the thin-film transistor Tr may have an inverted staggered structure in which the gate electrode is located on the lower part of the semiconductor layer and the source electrode and drain electrode are located on the upper part of the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon.

[0160] Although not shown in the diagram, gate wiring and data wiring intersect to define the pixel region, and switching thin-film transistors, which are switching elements connected to the gate wiring and data wiring, are further formed. The switching elements are connected to the thin-film transistor Tr, which acts as a driving element. Power wiring may also be formed parallel to or separated from the data wiring, and a storage capacitor may be further configured to maintain a constant voltage at the gate electrode of the thin-film transistor Tr during one frame.

[0161] A planarization layer 150 is formed on the front surface of the substrate 110 above the source electrode 144 and the drain electrode 146. The planarization layer 150 has a flat upper surface and has drain contact holes 152 that expose the drain electrode 146 of the thin-film transistor Tr.

[0162] The organic light-emitting diode D includes a first electrode 210 located on the planarization layer 150 and connected to the drain electrode 146 of the thin-film transistor Tr, and a light-emitting layer 220 and a second electrode 230 sequentially stacked on the first electrode 210. The organic light-emitting diode D is located in the red pixel region, green pixel region, and blue pixel region, respectively, and can emit red, green, and blue light, respectively.

[0163] The first electrode 210 is formed separately for each pixel region. The first electrode 210 may be anode and may be made of a conductive material with a relatively large work function value, such as transparent conductive oxide (TCO). Specifically, the first electrode 210 may be made of indium-tin oxide (ITO), indium-zinc oxide (IZO), indium-tin-zinc oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium-copper oxide (ICO), and aluminum:zinc oxide (Al:ZnO;AZO).

[0164] In the case of the organic light-emitting device 100 of the present invention being a bottom-emission type, the first electrode 210 may have a single-layer structure of a transparent conductive oxide layer. In contrast, in the case of the organic light-emitting device 100 of the present invention being a top-emission type, the first electrode 210 may further include a reflective layer and have a double-layer or triple-layer structure. For example, the reflective layer may be made of silver or an aluminum-palladium-copper (APC) alloy. In the top-emission type organic light-emitting diode D, the first electrode 210 may have a double-layer structure of Ag / ITO or APC / ITO, or a triple-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0165] Furthermore, a bank layer 160 is formed on the planarization layer 150, covering the edges of the first electrode 210. The bank layer 160 corresponds to the pixel region and exposes the center of the first electrode 210.

[0166] An organic light-emitting layer 220 is formed on the first electrode 210. The light-emitting layer 220 may have a single-layer structure of an emitting material layer (EML). Alternatively, the organic light-emitting layer 220 may have a multilayer structure, further including at least one of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a hole blocking layer (HBL), an electron transport layer (ETL), or an electron injection layer (EIL). Furthermore, the organic light-emitting diode D can have a tandem structure by arranging two or more emitting material layers spaced apart from each other.

[0167] In at least one of the red pixel region or the green pixel region, the organic light-emitting layer 220 of the organic light-emitting diode D contains the organometallic compound of the present invention, thereby greatly improving the luminous efficiency and light-emitting lifetime of the organic light-emitting diode D and the organic light-emitting display device 100.

[0168] A second electrode 230 is formed on the upper part of the substrate 110 on which the organic light-emitting layer 220 is formed. The second electrode 230 is located in front of the display area, is made of a conductive material with a relatively small work function value, and can be used as a negative electrode (cathode). For example, the second electrode 230 may be made of a material with good reflective properties such as aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), or alloys or combinations thereof. If the organic light-emitting display device 100 is an upper light-emitting type, the second electrode 230 has a thin thickness and has light-transmitting (semi-transmitting) properties.

[0169] An encapsulation layer (or encapsulation film) 170 is formed on the second electrode 230 to prevent external moisture from penetrating the organic light-emitting diode D. The encapsulation layer 170 may have, but is not limited to, a laminated structure of a first inorganic insulating layer 172, an organic insulating layer 174, and a second inorganic insulating layer 176.

[0170] Although not shown in the figures, the organic light-emitting display device 100 may include color filter layers corresponding to red, green, and blue pixel regions. The color filter layers may include red color filters, green color filters, and blue color filters corresponding to the red, green, and blue pixel regions, respectively. When the organic light-emitting display device 100 includes color filter layers, the color purity of the organic light-emitting display device 100 can be improved.

[0171] If the organic light-emitting device 100 is a bottom-emitting type, the color filter layer may be located between the organic light-emitting diode D and the substrate 110, for example, between the interlayer insulating film 132 and the planarization layer 150. Alternatively, if the organic light-emitting device 100 is a top-emitting type, the color filter layer may be located above the organic light-emitting diode D, i.e., above the second electrode 230. For example, the color filter layer may be formed on the encapsulation layer 170.

[0172] If the organic light-emitting display device 100 is a bottom-emitting type, a metal plate (not shown) may be further provided on top of the encapsulation layer 170.

[0173] The organic light-emitting display device 100 may further include a polarizing plate (not shown) for reducing reflection of external light. For example, the polarizing plate (not shown) may be a circular polarizing plate. If the organic light-emitting display device 100 is a bottom-emitting type, the polarizing plate may be located at the bottom of the substrate 110. If the organic light-emitting display device 100 of the present invention is an top-emitting type, the polarizing plate may be located at the top of the encapsulation layer 170.

[0174] Furthermore, in the top-emitting type organic light-emitting display device 100, a cover window (not shown) may be attached to the encapsulation layer 170. In this case, if the substrate 110 and the cover window (not shown) are made of a flexible material, a flexible display device can be constructed.

[0175] Figure 3 is a schematic cross-sectional view of an organic light-emitting diode according to a second embodiment of the present invention.

[0176] As shown in Figure 3, the organic light-emitting diode D1 of the present invention includes a first electrode 210 and a second electrode 230 facing each other, and an organic light-emitting layer 220 located between the first and second electrodes 210 and 230.

[0177] The organic light-emitting display device 100 includes a red pixel region, a green pixel region, and a blue pixel region. The organic light-emitting display device 100 may also further include a white pixel region. The organic light-emitting diode D1 may be located in at least one of the red pixel region and the green pixel region. For example, the organic light-emitting diode D1 may be located in the green pixel region.

[0178] The first electrode 210 may be a positive electrode, and the second electrode 230 may be a negative electrode. One of the first electrode 210 and the second electrode 230 is a transmission electrode, and the other of the first electrode 210 and the second electrode 230 is a reflection electrode.

[0179] The organic light-emitting layer 220 includes an emitting material layer (EML) 260.

[0180] Furthermore, the organic light-emitting layer 220 may further include at least one of the following: a hole transporting layer (HTL) 250 located between the first electrode 210 and the light-emitting material layer 260, and an electron transporting layer (ETL) 270 located between the light-emitting material layer 260 and the second electrode 230.

[0181] Furthermore, the organic light-emitting layer 220 may further include at least one of the following: a hole injection layer (HIL) 240 located between the first electrode 210 and the hole transport layer 250, and an electron injection layer (EIL) 280 located between the second electrode 230 and the electron transport layer 270.

[0182] Furthermore, the organic light-emitting layer 220 may further include at least one of the following: an electron blocking layer (EBL) 255 located between the hole transport layer 250 and the light-emitting material layer 260, and a hole blocking layer (HBL) 275 located between the light-emitting material layer 260 and the electron transport layer 270.

[0183] In other words, the organic light-emitting diode D1 according to the second embodiment of the present invention has a single light-emitting unit.

[0184] The hole injection layer 240 contains 4,4',4”-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4”-tris(N,N-diphenyl-amino)triphenylamine (NATA), and 4,4',4”-tris(N-(naphthalen-1-yl)-N-phenyl -amino)triphenylamine (4,4',4”-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine; 1T-NATA), 4,4',4”-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (4,4',4”-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine; 2T-NATA), phthalocyanine copper phthalocyanine (CuPc), tris(4-carbazoyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4”-diamine (NPB or NPD), 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiphene)polystyrene sulfonate;The hole injection material may include, but is not limited to, any one of the following: PEDOT / PSS, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, or N,N'-diphenyl-N,N'-di-[4-(N,N-diphenyl-amino)phenyl]benzidine (NPNPB). For example, the hole injection material in the hole injection layer 340 may include the compound of the following chemical formula 4. The hole injection layer 240 may have a thickness of 5 to 100 nm. ;

[0185] The hole transport layer 250 contains N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), NPB (NPD), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)-benzidine] (Poly-TPD), poly[ (9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))](poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))], TFB), di-[4-(N,N-di-p-tolyl-amino)phenyl]cyclohexane(di-[4-(N,N-di-p-tolyl-amino)-phenyl]cyclohexane; TAPC), 3,5-di(9H-carbazol-9-yl)-N,N-diphenylaniline(3,5-di(9H-carbazol-9-yl)-N,N-diphenylaniline;DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine (N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine), N-(biphenyl]-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl)-4-amine (N-(biphenyl-4-yl)-N-(4-(9-ph The hole transporter may contain, but is not limited to, one of the following: ([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine. For example, the hole transporter in the hole transporter layer 250 may contain the compound of chemical formula 5. The hole transporter layer 250 may have a thickness of 50 nm to 150 nm, preferably 50 nm to 120 nm.

[0186] The electron transport layer 270 contains tris-(8-hydroxyquinoline)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-t-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, and lithium quinolate (lithium quinolate (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalene-2-yl)4,7-diphenyl-1,10-phenanthroline (2,9-Bis(naphthalene-2-yl)4,7-diphenyl-1,10-phenanthroline (Phen) nanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3-(4-Biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tri(p-pyrid-3-yl-phenyl)benzene (Tri(p-pyrid-3-yl-phenyl)benzene;TpPyPB), 2,4,6-Tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), Poly[(9,9-bis(3'-((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene)-alt-2,7-(9,9-dioctylfluorene)](Poly[9,9-bi The electron transport material may be one of the following: s(3'-((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alt-2,7-(9,9-dioctylfluorene)];PFNBr), tris(phenylquinoxaline;TPQ), diphenyl-4-triphenylsilyl-phenylphosphine oxide;TSPO1, 2-[4-(9,10-Di-2-naphthalen2-yl-anthracen-2-yl)phenyl]-1-phenyl-1H-benzimidazole (ZADN). For example, the electron transport material of the electron transport layer 270 may include, but is not limited to, the compound of chemical formula 7 and the compound of chemical formula 8. The electron transport layer 270 may have a thickness of 10 to 50 nm, preferably 15 to 40 nm.

[0187] The electron injection layer 280 may contain an electron injection material which is one of the following: LiF, CsF, NaF, BaF2, Liq (lithium quinolate), lithium benzoate, or sodium stearate. The electron injection layer 280 may have a thickness of 0.1 to 10 nm, preferably 0.5 to 5 nm.

[0188] In Figure 3, the electron transport layer 270 and the electron injection layer 280 are formed separately. Alternatively, a single-layer electron transport-injection layer that performs both electron transport and electron injection roles can be formed. In this case, the electron transport-injection layer may contain an electron transport material and an electron injection material, and may have a thickness of 10 to 50 nm. For example, the electron transport-injection layer may contain a compound of chemical formula 7 and a compound of chemical formula 8. In this case, the weight ratio of the compound of chemical formula 7 and the weight ratio of the compound of chemical formula 8 in the electron transport-injection layer may be the same.

[0189] The electron barrier layer 255, located between the light-emitting material layer 260 and the hole transport layer 250, which prevents electron transfer from the light-emitting material layer 260 to the hole transport layer 250, is composed of TCTA, tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, TAPC, MTDATA, 1,3-bis(carbazol-9-yl)benzene(mCP), 3, The electron-blocking material may include, but is not limited to, one of the following: 3'-bis(N-carbazolyl)-1,1'-biphenyl (mCBP), CuPc, N,N'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD), TDAPB, DCDPA, or 2,8-bis(9-phenyl-9H-carbazol-3-yl)dibenzo[b,d]thiophene). For example, the electron-blocking material of the electron-blocking layer 255 may include the compound of chemical formula 6. The electron-blocking layer 255 may have a thickness of 1 to 30 nm.

[0190] The hole-blocking layer 275, located between the light-emitting material layer 260 and the electron transport layer 270, which prevents hole movement from the light-emitting material layer 260 to the electron transport layer 270, may be made of the same material as the electron transport layer 270 described above. For example, the hole-blocking layer 275 may contain, but is not limited to, one of the following hole-blocking materials: BCP, BAlq, Alq3, PBD, spiro-PBD, Liq, bis-4,6-(3,5-di-3-pyridylphenyl)-2-methylpyrimidine (B3PYMPM), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 9-(6-9H-carbazol-9-yl)pyridine-3-yl)-9H-3,9'-bicarbazole, or TSPO1. For example, the hole-blocking material of the hole-blocking layer 275 may contain the compound of chemical formula 8. The hole-blocking layer 275 may have a thickness of 1 to 30 nm.

[0191] The light-emitting material layer 260 may have a thickness of 10 to 100 nm, preferably 20 to 50 nm.

[0192] In at least one of the red pixel region and the green pixel region, the light-emitting material layer 260 contains a first compound 262, which is an organometallic compound of the present invention. The first compound 262 acts as a dopant (light-emitting body). The light-emitting material layer 260 may further contain a second compound (not shown) which is a host. In the light-emitting material layer 260, the first compound 262 has a smaller weight ratio than the second compound. For example, in the light-emitting material layer 260, the first compound 262 may be present in an amount of 1 to 40% by weight, preferably 1 to 20% by weight, and more preferably 1 to 10% by weight.

[0193] If the light-emitting material layer 260 contains the first compound 262, which is an organometallic compound of the present invention, in all of the red and green pixel regions, the first compound 262 (red dopant) in the light-emitting material layer 260 of the red pixel region and the first compound 262 (green dopant) in the light-emitting material layer 260 of the green pixel region have differences in the auxiliary ligand of chemical formula 1 and emit light of different wavelengths.

[0194] For example, when a voltage is applied to the first electrode 210 and the second electrode 230, holes from the first electrode 210 and electrons from the second electrode 230 are transferred to the light-emitting material layer 260, and excitons are generated in the second compound. The generated excitons are transferred to the first compound 262, and light is emitted from the first compound 262.

[0195] If the light-emitting material layer 260 in the green pixel region contains a first compound 262 which is an organometallic compound of chemical formula 1, the light-emitting material layer 260 in the green pixel region may further contain a second compound which is a green host.

[0196] For example, the second compound (green host) is 9-(3-(9H-carbazol-9-yl)phenyl)-9H-carbazol-3-carbonitrile (mCP-CN), CBP, 3,3'-bis(N-carbazolyl)-1,1'-biphenyl (mCBP), 1,3-bis(carbazol-9-yl)benzene (1,3-Bis(carbazol-9-yl)benzene; mCP), DPEPO, 2,8-bis(diphenylphosphoryl)dibenzothiophene (2,8-bis(diphenylphosphoryl)dibenzothiophene; PPT), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene (1,3,5-Tri[(3-pyridyl)-phen-3-yl]benzene; TmPyPB), 2,6-di(9H-carbazol-9-yl)pyridine (2,6-Di (9H-carbazol-9-yl)pyridine; PYD-2Cz), 2,8-di(9H-carbazol-9-yl)dibenzothiophene; DCzDBT, 3',5'-di(carbazol-9-yl)-[1,1'-biphenyl]-3,5-dicarbonitrile; DCzTPA, 4' -(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile (4'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile; pCzB-2CN), 3'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile (3'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile;The green host substance may be, but is not limited to, one of the following: mCzB-2CN, TSPO1, or 9-(9-phenyl-9H-carbazol-6-yl)-9H-carbazole (CCP).

[0197] If the light-emitting material layer 260 in the red pixel region contains a first compound 262 which is an organometallic compound of chemical formula 1, the light-emitting material layer 260 in the red pixel region may further contain a second compound which is a red host.

[0198] For example, the second compound (red host) is 9-(3-(9H-carbazol-9-yl)phenyl)-9H-carbazol-3-carbonitrile (mCP-CN), CBP, 3,3'-bis(N-carbazolyl)-1,1'-biphenyl (mCBP), 1,3-bis(carbazol-9-yl)benzene (1,3-Bis(carbazol-9-yl)benzene; mCP), DPEPO, 2,8-bis(diphenylphosphoryl)dibenzothiophene (2,8-bis(diphenylphosphoryl)dibenzothiophene; PPT), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene (1,3,5-Tri[(3-pyridyl)-phen-3-yl]benzene; TmPyPB), 2,6-di(9H-carbazol-9-yl)pyridine (2,6-Di (9H-carbazol-9-yl)pyridine; PYD-2Cz), 2,8-di(9H-carbazol-9-yl)dibenzothiophene; DCzDBT, 3',5'-di(carbazol-9-yl)-[1,1'-biphenyl]-3,5-dicarbonitrile; DCzTPA, 4' -(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile (4'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile; pCzB-2CN), 3'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile (3'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile;mCzB-2CN), TSPO1, 9-(9-phenyl-9H-carbazol-6-yl)-9H-carbazole (CCP), 4-(3-(triphenylen-2-yl)phenyl)dibenzo[b,d]thiophene, 9-(4-(9H-carbazol-9-yl)phenyl)-9H-3,9' -bicarbazole(9-(4-(9H-carbazol-9-yl)phenyl)-9H-3,9'-bicarbazole), 9-(3-(9H-carbazol-9-yl)phenyl)-9H-3,9'-bicarbazole(9-(3-(9H-carbazol-9-yl)phenyl)-9H-3,9'-bicarbazole), 9-(6-(9H-carbazol-9-yl)pyridine-3-yl)-9H-3,9'-bicarbazole(9-(6-(9H-carbazol-9-yl) Pyridin-3-yl)-9H-3,9'-bicabazole), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), 1,3,5-Tris(carbazole-9-yl)benzene (TCP), TCTA, 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (4,4'-Bis(c arbazole-9-yl)-2,2'-dimethylbipheyl (CDBP), 2,7-bis(carbazole-9-yl)-9,9-dimethylfluorene (2,7-Bis(carbazole-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,2',7,7'-tetrakis(carbazole-9-yl)-9,9-spirobifluorene (2,2',7,7'-Tetrakis(carbazole-9-yl)-9,9-spirofluorene;It may be any one of the following: Spiro-CBP), 3,6-Bis(carbazole-9-yl)-9-(2-ethyl-hexyl)-9H-carbazole (TCz1), bis(2-hydroxylphenyl)-pyridine)beryllium (Bepp2), bis(10-hydroxylbenzo[h]quinolinato)beryllium (Bebq2), or 1,3,5-tris(1-pyrenyl)benzene (TPB3).

[0199] In contrast, the luminescent material layer 260 in the red pixel region may contain a red dopant instead of an organometallic compound of chemical formula 1. In this case, the red dopant may contain at least one of a red phosphorescent substance, a red fluorescent substance, and a red delayed fluorescent substance. For example, the red dopant may be [Bis(2-(4,6-dimethyl)phenylquinoline)](2,2,6,6-tetramethylheptane-3,5-dionate)iridium(III) ([Bis(2-(4,6-dimethyl)phenylquinoline)](2,2,6,6-tetramethylheptane-3,5-dionate)iridium(III) (Bis[2-(4-n-hexylphenyl)quinoline](acetylacetonate)iridium(III) (Bis [2-(4-n-hexylphenyl)quinoline](acetylacetonate)iridium(III);Hex-Ir(phq)2(acac)), Tris[2-(4-n-hexylphenyl)quinoline]iridium(III) (Tris[2-(4-n-hexylphenyl)quinoline]iridium(III,Hex-Ir(phq)3), Tris[2-phenyl-4-methylquinoline]iridium(III) (Tris[2-pheny l-4-methylquinoline]iridium(III), Ir(Mphq)3), bis(2-phenylquinoline)(2,2,6,6-tetramethylheptane-3,5-dionate)iridium(III), Ir(dpm)PQ2), bis(phenylisoquinoline)(2,2,6,6-tetramethylheptane-3 ,5-dione)iridium(III)(Bis(phenylisoquinoline)(2,2,6,6-tetramethylheptane-3,5-dionate)iridium(III), Ir(dpm)(piq)2), bis[(4-n-hexylphenyl)isoquinoline](acetylacetonate)iridium(III)(Bis[(4-n-hexylphenyl)isoquinoline](acetylacetonate)iridium(III);Hex-Ir(piq)2(acac)), Tris[2-(4-n-hexylphenyl)quinoline]iridium(III), Hex-Ir(piq)3, Tris(2-(3-methylphenyl)-7-methyl-quinolato)iridium;Ir(dmpq)3, Bis[2-(2-methylphenyl)-7-methyl-quinoline](acetylacetonate)iridium The group consisting of (III)(Bis[2-(2-methylphenyl)-7-methyl-quinoline](acetylacetonate)iridium(III);Ir(dmpq)2(acac)) and bis[2-(3,5-dimethylphenyl)-4-methyl-quinoline](acetylacetonate)iridium(III)(Bis[2-(3,5-dimethylphenyl)-4-methyl-quinoline](acetylacetonate)iridium(III);Ir(mphmq)2(acac)) can be selected.

[0200] The organometallic compound of the present invention is an iridium complex having the structure of chemical formula 1, and is included in the light-emitting material layer 260 of the organic light-emitting diode D1, thereby improving the luminous efficiency and lifespan of the organic light-emitting diode D1 and the organic light-emitting display device 100.

[0201] [Organic Light-Emitting Diode] A green organic light-emitting diode was formed by sequentially depositing a hole injection layer (chemical formula 4 compound (HI-1), 60 nm), a hole transport layer (chemical formula 5 compound (NPB), 80 nm), a light-emitting material layer (host (chemical formula 6 compound (CBP), 95 wt%), dopant (5 wt%), 30 nm), an electron transport-injection layer (chemical formula 7 compound (ET-1) + chemical formula 8 compound (Liq) (weight ratio = 1:1), 30 nm), and a negative electrode (Al, 15 nm) onto a glass substrate coated with a positive electrode (ITO, 100 nm). [ka] [ka] [ka] [ka] [ka]

[0202] 1. Comparative Example (1) Comparative Example 1 (Ref1) Compound Ref1, with chemical formula 9, was used as the dopant. (2) Comparative Example 2 (Ref2) Compound Ref2, with chemical formula 9, was used as the dopant. (3) Comparative Example 3 (Ref3) Compound Ref3, with chemical formula 9, was used as the dopant. (4) Comparative Example 4 (Ref4) Compound Ref4, with chemical formula 9, was used as the dopant. (5) Comparative Example 5 (Ref5) Compound Ref5, with chemical formula 9, was used as the dopant. [ka]

[0203] 2. Experimental Examples (1) Experimental Example 1 (Ex1) Compound 238, with chemical formula 3, was used as the dopant. (2) Experimental Example 2 (Ex2) Compound 247, with chemical formula 3, was used as the dopant. (3) Experimental Example 3 (Ex3) Compound 243, with chemical formula 3, was used as the dopant. (4) Experimental Example 4 (Ex4) Compound 252, with chemical formula 3, was used as the dopant. (5) Experimental Example 5 (Ex5) Compound 310, with chemical formula 3, was used as the dopant. (6) Experimental Example 6 (Ex6) Compound 319, with chemical formula 3, was used as the dopant. (7) Experimental Example 7 (Ex7) Compound 315, with chemical formula 3, was used as the dopant. (8) Experimental Example 8 (Ex8) Compound 324, with chemical formula 3, was used as the dopant. (9) Experimental Example 9 (Ex9) Compound 472, with chemical formula 3, was used as the dopant. (10) Experimental Example 10 (Ex10) Compound 481, with chemical formula 3, was used as the dopant. (11) Experimental Example 11 (Ex11) Compound 477, with chemical formula 3, was used as the dopant. (12) Experimental Example 12 (Ex12) Compound 486, with chemical formula 3, was used as the dopant. (13) Experimental Example 13 (Ex13) Compound 580, with chemical formula 3, was used as the dopant. (14) Experimental Example 14 (Ex14) Compound 589, with chemical formula 3, was used as the dopant. (15) Experimental Example 15 (Ex15) Compound 582, with chemical formula 3, was used as the dopant. (16) Experimental Example 16 (Ex16) Compound 591, with chemical formula 3, was used as the dopant. (17) Experimental Example 17 (Ex17) Compound 546, with chemical formula 3, was used as the dopant. (18) Experimental Example 18 (Ex18) Compound 555, with chemical formula 3, was used as the dopant.

[0204] The characteristics of the organic light-emitting diodes fabricated in Comparative Examples 1 to 5 and Experimental Examples 1 to 18 (drive voltage (V), external quantum efficiency (EQE), and lifetime (LT95)) were measured and are listed in Table 1. (The characteristics of the organic light-emitting diodes were measured at room temperature using a current source (KEITHLEY) and a photometer (PR650), and the external quantum efficiency and lifetime are relative values ​​to Comparative Example 1.)

[0205] [Table 1]

[0206] As can be seen from Table 1, the driving voltage is reduced and the luminous efficiency and lifespan are increased in the organic light-emitting diodes of Experimental Examples 1 to 18 compared to the organic light-emitting diodes of Comparative Examples 1 to 5.

[0207] For example, compared to Comparative Example 1, which uses compound Ref1 in which the pyridylmoiate of the pyridyl-dibenzothiophene ligand is not substituted, and Comparative Example 3, which uses compound Ref3 in which the pyridylmoiate of the pyridyl-azadibenzothiophene ligand is not substituted, the luminous efficiency and lifetime of the organic light-emitting diodes in Experimental Examples 1 to 18, which use the organic compounds of the present invention in which the pyridylmoiate of the pyridyl-dibenzothiophene ligand or the pyridylmoiate of the pyridyl-azadibenzothiophene ligand is substituted with an aryl group, are increased.

[0208] Furthermore, compared to Comparative Example 2, which uses compound Ref2 in which the pyridylmoyate of the pyridyl-dibenzothiophene ligand is substituted with a phenyl group; Comparative Example 4, which uses compound Ref4 in which the pyridylmoyate of the pyridyl-azadibenzothiophene ligand is substituted with a phenyl group; and Comparative Example 5, which uses compound Ref5 in which the pyridylmoyate of the pyridyl-azadibenzothiophene ligand is substituted with a biphenyl group, the lifetime of the organic light-emitting diodes in Experimental Examples 1 to 18 using the organic compounds of the present invention in which the pyridylmoyate of the pyridyl-dibenzothiophene ligand or the pyridylmoyate of the pyridyl-azadibenzothiophene ligand is substituted with a naphthyl group is significantly increased.

[0209] Furthermore, compared to Experimental Examples 1, 3, 5, 7, 9, 11, 13, 15, and 17, the lifetime of organic light-emitting diodes in Experimental Examples 2, 4, 6, 8, 10, 12, 14, 16, and 18, which use compounds 247, 252, 319, 324, 481, 486, 589, 591, and 555 containing deuterium-substituted alkyl groups (CD3), is further increased.

[0210] Furthermore, in chemical formula 2, n is 2, n1 is 0, X10, X1-X4 are CH, R1 and R2-1 are independently unsubstituted or deuterium-substituted C1-C20 alkyl groups (e.g., CH3 or CD3), and R2-2 is a substituted or unsubstituted C6-C30 aryl group (e.g., phenyl). The lifetime of the organic light-emitting diodes in Experimental Examples 13 and 14 using compounds 580 and 589 is further increased.

[0211] Furthermore, in chemical formula 2, n is 2, n1 is 0, X10 and N, X2 is CR4 (R4 = CH3 or CD3), X3 and X4 are CH, and R1, R2-1, and R2-2 are independently unsubstituted or deuterium-substituted C1-C20 alkyl groups (e.g., CH3 or CD3). The lifetime of the organic light-emitting diodes in Experimental Examples 17 and 18, using compounds 546 and 555, is further increased.

[0212] Figure 4 is a schematic cross-sectional view of an organic light-emitting diode according to a third embodiment of the present invention.

[0213] As shown in Figure 4, the organic light-emitting diode D2 includes a first electrode 210 and a second electrode 230 facing each other, and an organic light-emitting layer 220 located between the first and second electrodes 210 and 230.

[0214] The organic light-emitting display device (100 in Figure 2) includes a red pixel region, a green pixel region, and a blue pixel region. The organic light-emitting display device 100 may also further include a white pixel region. The organic light-emitting diode D2 may be located in at least one of the red pixel region and the green pixel region. For example, the organic light-emitting diode D2 may be located in the green pixel region.

[0215] The first electrode 210 may be a positive electrode, and the second electrode 230 may be a negative electrode. One of the first electrode 210 and the second electrode 230 is a transmission electrode, and the other of the first electrode 210 and the second electrode 230 is a reflection electrode.

[0216] The organic light-emitting layer 320 includes a first light-emitting unit 340 containing a first light-emitting material layer 350, and a second light-emitting unit 360 containing a second light-emitting material layer 370. The organic light-emitting layer 320 may further include a charge-generating layer 380 located between the first light-emitting unit 340 and the second light-emitting unit 360.

[0217] The charge generation layer 380 is located between the first and second light-emitting units 340 and 360, and the first light-emitting unit 340, the charge generation layer 380, and the second light-emitting unit 360 are sequentially stacked on the first electrode 210. That is, the first light-emitting unit 340 is located between the first electrode 210 and the charge generation layer 380, and the second light-emitting unit 360 is located between the second electrode 230 and the charge generation layer 380.

[0218] The first light-emitting unit 340 may further include at least one of the following: a first hole transport layer 340b located between the first electrode 210 and the first light-emitting material layer 350; a hole injection layer 340a located between the first electrode 210 and the first hole transport layer 340b; and a first electron transport layer 340e located between the first light-emitting material layer 350 and the charge generation layer 380.

[0219] Furthermore, the first light-emitting unit 340 may further include at least one of the following: a first electron-blocking layer 340c located between the first hole transport layer 340b and the first light-emitting material layer 350, and a first hole-blocking layer 340d located between the first light-emitting material layer 350 and the first electron transport layer 340e.

[0220] The second light-emitting unit 360 may further include at least one of the following: a second hole transport layer 360a located between the charge generation layer 380 and the second light-emitting material layer 370; a second electron transport layer 360d located between the second light-emitting material layer 370 and the second electrode 230; and an electron injection layer 360e located between the second electron transport layer 360d and the second electrode 230.

[0221] Furthermore, the second light-emitting unit 360 may further include at least one of the following: a second electron-blocking layer 360b located between the second hole transport layer 360a and the second light-emitting material layer 370, and a second hole-blocking layer 360c located between the second light-emitting material layer 370 and the second electron transport layer 360d.

[0222] The hole injection layer 340a may contain the aforementioned hole injection material. For example, the hole injection layer 340a may have a thickness of 10 to 100 nm.

[0223] The first and second hole transport layers 340b and 360a may each contain the aforementioned hole transport material. For example, the first and second hole transport layers 340b and 360a may each have a thickness of 30 nm to 150 nm, preferably 50 nm to 120 nm.

[0224] The first and second electron transport layers 340e and 360d may each contain the electron transport material described above. For example, the first and second electron transport layers 340e and 360d may each have a thickness of 10 nm to 100 nm, preferably 10 nm to 50 nm.

[0225] The electron injection layer 360e may contain the electron injection material described above. For example, the electron injection layer 360e may have a thickness of 0.1 to 10 nm, preferably 0.5 to 5 nm.

[0226] In Figure 4, the second electron transport layer 360d and the electron injection layer 360e are formed separately. Alternatively, a single-layer electron transport-injection layer that performs both electron transport and electron injection roles can be formed. In this case, the electron transport-injection layer may contain an electron transport material and an electron injection material, and may have a thickness of 10 to 50 nm. For example, the electron transport-injection layer may contain a compound of chemical formula 7 and a compound of chemical formula 8. In this case, the weight ratio of the compound of chemical formula 7 and the weight ratio of the compound of chemical formula 8 in the electron transport-injection layer may be the same.

[0227] The first and second electron-blocking layers 340c and 360b may each contain the aforementioned electron-blocking material. For example, the first and second electron-blocking layers 340c and 360b may each have a thickness of 1 to 30 nm.

[0228] The first and second hole-blocking layers 340d and 360c may each contain the aforementioned hole-blocking material. For example, the first and second hole-blocking layers 340d and 360c may each have a thickness of 1 to 30 nm.

[0229] The charge generation layer 380 is located between the first light-emitting unit 340 and the second light-emitting unit 360. That is, the first light-emitting unit 340 and the second light-emitting unit 360 are connected by the charge generation layer 380. The charge generation layer 380 may be a PN junction charge generation layer in which an N-type charge generation layer 382 and a P-type charge generation layer 384 are joined together.

[0230] The N-type charge generation layer 382 is located between the first electron transport layer 340e and the second hole transport layer 360a, and the P-type charge generation layer 384 is located between the N-type charge generation layer 382 and the second hole transport layer 360a. The N-type charge generation layer 382 transfers electrons to the first light-emitting material layer 350 of the first light-emitting unit 340, and the P-type charge generation layer 384 transfers holes to the second light-emitting material layer 370 of the second light-emitting unit 360.

[0231] The N-type charge generation layer 382 may be an organic layer doped with alkali metals such as Li, Na, K, and Cs and / or alkaline earth metals such as Mg, Sr, Ba, and Ra. For example, the N-type charge generation layer 382 may consist of an N-type charge generating material comprising a host which is an organic substance such as 4,7-diphenyl-1,10-phenanthroline (Bphen) or MTDATA, and a dopant which is an alkali metal or alkaline earth metal, and the dopant may be doped in an amount of 0.01 to 30% by weight.

[0232] The P-type charge generation layer 384 may consist of a P-type charge generation material comprising at least one of the following: an inorganic substance selected from the group consisting of tungsten oxide (WOx), molybdenum oxide (MoOx), beryllium oxide (Be2O3), vanadium oxide (V2O5), and combinations thereof; or an organic substance selected from the group consisting of NPD, HAT-CN, F4TCNQ, TPD, TNB, TCTA, N,N'-dioctyl-3,4,9,10-perylenedicarboximide (PTCDI-C8), and combinations thereof.

[0233] The first luminescent material layer 350 and the second luminescent material layer 370 may be green luminescent material layers. At least one of the first luminescent material layer 350 and the second luminescent material layer 370 contains a first compound which is an organometallic compound represented by chemical formula 1. The first luminescent material layer 350 and the second luminescent material layer 370 may further contain a second compound which is a green host. The first compound may be present in an amount of 1 to 40% by weight, preferably 1 to 20% by weight, and more preferably 1 to 10% by weight.

[0234] The second compound (green host) may be the green host substance described above.

[0235] For example, both the first luminescent material layer 350 and the second luminescent material layer 370 may contain a first compound which is an organometallic compound represented by chemical formula 1 and a second compound which is a green host. In this case, the first compound in the first luminescent material layer 350 and the first compound in the second luminescent material layer 370 may be the same or different from each other. Also, the second compound in the first luminescent material layer 350 and the second compound in the second luminescent material layer 370 may be the same or different from each other.

[0236] In contrast, one of the first luminescent material layer 350 and the second luminescent material layer 370 may contain a first compound (first green dopant) which is an organometallic compound represented by chemical formula 1 and a second compound (first green host) which is a green host, and the other of the first luminescent material layer 350 and the second luminescent material layer 370 may contain a green dopant (second green dopant) which is a phosphorescent compound, a fluorescent compound or a delayed fluorescent compound and a green host (second green host). In this case, the second green dopant may be, but is not limited to, one of [Bis(2-phenylpyridine)](pyridyl-2-benzofuro[2,3-b]pyridine)iridium), Ir(ppy)3, fac-Ir(ppy)3, Ir(ppy)2(acac), Ir(mppy)3, Ir(npy)2(acac), Ir(3mppy)3, or TEG.

[0237] The first luminescent material layer 350 and the second luminescent material layer 370 may be red luminescent material layers. At least one of the first luminescent material layer 350 and the second luminescent material layer 370 contains a first compound which is an organometallic compound represented by chemical formula 1. The first luminescent material layer 350 and the second luminescent material layer 370 may further contain a second compound which is a red host. The first compound may be present in an amount of 1 to 40% by weight, preferably 1 to 20% by weight, and more preferably 1 to 10% by weight.

[0238] The second compound (red host) may be the red host substance described above.

[0239] For example, in the red pixel region, the entirety of the first light-emitting material layer 350 and the second light-emitting material layer 370 may contain a first compound, which is an organometallic compound represented by chemical formula 1, and a second compound, which is a red host. In this case, the first compound in the first light-emitting material layer 350 and the first compound in the second light-emitting material layer 370 may be the same or different from each other. Also, the second compound in the first light-emitting material layer 350 and the second compound in the second light-emitting material layer 370 may be the same or different from each other.

[0240] In contrast, one of the first luminescent material layer 350 and the second luminescent material layer 370 may contain a first compound (first red dopant) which is an organometallic compound represented by chemical formula 1 and a second compound (first red host) which is a red host, while the other of the first luminescent material layer 350 and the second luminescent material layer 370 may contain a red dopant (second red dopant) instead of an organometallic compound of chemical formula 1. In this case, the second red dopant may contain at least one of a phosphorescent compound, a fluorescent compound, and a delayed fluorescent compound. For example, the red dopant may be the red host substance described above.

[0241] The organometallic compound of the present invention is an iridium complex having the structure of chemical formula 1, and is included in at least one of the first and second light-emitting material layers 350 and 370 of the organic light-emitting diode D2, thereby improving the luminous efficiency and lifespan of the organic light-emitting diode D2 and the organic light-emitting display device 100.

[0242] Furthermore, since the organic light-emitting diode D2 has a double-stack structure of either a green light-emitting material layer or a double-stack structure of a red light-emitting material layer, the color perception of the organic light-emitting diode D2 is improved and the luminous efficiency is optimized.

[0243] Figure 5 is a schematic cross-sectional view of an organic light-emitting display device according to a fourth embodiment of the present invention.

[0244] As shown in Figure 5, the organic light-emitting display device 500 according to the fourth embodiment of the present invention includes a first substrate 502 in which a red pixel region RP, a green pixel region GP, ​​and a blue pixel region BP are defined, a second substrate 504 facing the first substrate 502, an organic light-emitting diode D located between the first substrate 502 and the second substrate 504 and emitting white light, and a color filter layer 580 located between the organic light-emitting diode D and the second substrate 504.

[0245] The first substrate 502 and the second substrate 504 may each be a glass substrate or a plastic substrate. For example, the first and second substrates 502 and 504 may each be one of the following: a PI substrate, a PES substrate, a PEN substrate, a PET substrate, and a PC substrate.

[0246] A buffer layer 506 is formed on the first substrate 502, and thin-film transistors Tr are formed on the buffer layer 506 corresponding to the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP, respectively. The buffer layer 506 may be omitted. The thin-film transistors Tr may also be driving thin-film transistors.

[0247] A semiconductor layer 510 is formed on the buffer layer 506. For example, the semiconductor layer 510 may be made of an oxide semiconductor material or polycrystalline silicon.

[0248] A gate insulating film 520 made of an insulating material, such as an inorganic insulating material like silicon oxide or silicon nitride, is formed on the upper part of the semiconductor layer 510.

[0249] On top of the gate insulating film 520, a gate electrode 530 made of a conductive material such as metal is formed corresponding to the center of the semiconductor layer 510.

[0250] An interlayer insulating film 540 is formed on the upper part of the gate electrode 530, consisting of an insulating material, an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or photo-acrylic.

[0251] The interlayer insulating film 540 has first and second semiconductor layer contact holes 542 and 544 that expose the surfaces on both sides of the semiconductor layer 510. The first and second semiconductor layer contact holes 542 and 544 are located on both sides of the gate electrode 530, spaced apart from the gate electrode 530.

[0252] A source electrode 552 and a drain electrode 554 made of a conductive material such as metal are formed on the upper part of the interlayer insulating film 540. The source electrode 552 and the drain electrode 554 are located spaced apart from the gate electrode 530 and contact both sides of the semiconductor layer 510 via the first and second semiconductor layer contact holes 542 and 544, respectively.

[0253] The semiconductor layer 510, gate electrode 530, source electrode 552, and drain electrode 554 constitute a thin-film transistor Tr.

[0254] A planarization layer 560 is formed on the front surface of the first substrate 502, covering the thin-film transistor Tr above the source electrode 552 and the drain electrode 554. The planarization layer 560 has drain contact holes 562 that expose the drain electrode 554 of the thin-film transistor Tr.

[0255] An organic light-emitting diode D is located on the planarization layer 560. The organic light-emitting diode D includes a first electrode 610 connected to the drain electrode 554 of a thin-film transistor Tr, a second electrode 620 facing the first electrode 610, and an organic light-emitting layer 615 located between the first and second electrodes 610 and 620.

[0256] The first electrode 610 is positioned separately for each pixel region and may be a positive electrode (anode). The first electrode 610 includes a transparent conductive oxide layer.

[0257] A bank layer 564 is formed on the planarization layer 560, covering the edges of the first electrode 610. The bank layer 564 exposes the center of the first electrode 610, corresponding to the pixel regions RP, GP, and BP. Since the organic light-emitting diode D emits white light in the red, green, and blue pixel regions RP, GP, and BP, the organic light-emitting layer 615 does not need to be separated from the red, green, and blue pixel regions RP, GP, and BP and may be formed as a common layer. The bank layer 564 is formed to prevent current leakage at the edges of the first electrode 610, and the bank layer 564 may be omitted.

[0258] The organic light-emitting layer 615 is formed on the first electrode 610 and includes two or more light-emitting units, as described later. That is, the organic light-emitting diode D has a tandem structure. For example, as shown in Figures 6 to 8, the organic light-emitting layer 615 may include a number of light-emitting units 630, 730, 830, 930, 1030, 1130, 1230, 1330 and one or more charge generation layers 690, 890, 990, 1190, 1290. Each light-emitting unit includes a light-emitting material layer, and the charge generation layer is located between adjacent light-emitting units.

[0259] A second electrode 620 is formed on the upper part of the first substrate 502 on which the organic light-emitting layer 615 is formed. The second electrode 620 is located in front of the display area and may be a negative electrode (cathode).

[0260] In the organic light-emitting display device 500, light emitted from the organic light-emitting layer 6150 is incident on the color filter layer 580 via the second electrode 620, so the second electrode 620 has a thin thickness to allow light to pass through. In addition, a reflective layer may be located below the first electrode 610.

[0261] The color filter layer 580 is located on top of the organic light-emitting diode D and includes a red color filter 582, a green color filter 584, and a blue color filter 586, corresponding to the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP, respectively. The red color filter 582 may contain at least one of a red dye and a red pigment, the green color filter 584 may contain at least one of a green dye and a green pigment, and the blue color filter 586 may contain at least one of a blue dye and a blue pigment.

[0262] Although not shown in the diagram, the color filter layer 580 may be attached to the organic light-emitting diode D by an adhesive layer. Alternatively, the color filter layer 580 may be formed directly on the organic light-emitting diode D.

[0263] Furthermore, an encapsulation layer is formed to cover the organic light-emitting diode D, and the color filter layer 580 can also be formed on the encapsulation layer.

[0264] In Figure 5, the light emitted from the organic light-emitting layer 615 passes through the second electrode 620, and the color filter layer 580 is positioned above the organic light-emitting diode D. Alternatively, the light from the organic light-emitting layer 615 could pass through the first electrode 610, and the color filter layer 580 could be positioned between the organic light-emitting diode D and the first substrate 502.

[0265] Furthermore, a color conversion layer (not shown) may be provided between the organic light-emitting diode D and the color filter layer 580. The color conversion layer includes a red color conversion layer, a green color conversion layer, and a blue color conversion layer corresponding to each pixel region, and can convert the white light emitted from the organic light-emitting diode D into red, green, and blue light, respectively.

[0266] As described above, the white light emitted from the organic light-emitting diode D passes through the red color filter 582, green color filter 584, and blue color filter 586, which correspond to the red pixel region RP, green pixel region GP, ​​and blue pixel region BP, respectively, resulting in the display of red, green, and blue light in the red pixel region RP, green pixel region GP, ​​and blue pixel region BP.

[0267] Figure 6 is a schematic cross-sectional view of an organic light-emitting diode according to a fifth embodiment of the present invention.

[0268] As shown in Figure 6, the organic light-emitting diode D3 according to the fifth embodiment of the present invention includes a first electrode 610 and a second electrode 620 facing each other, and an organic light-emitting layer 615 located between the first electrode 610 and the second electrode 620, wherein the organic light-emitting layer 615 includes a first light-emitting unit 630 located between the first electrode 610 and the second electrode 620, and a second light-emitting unit 730 located between the first light-emitting unit 630 and the second electrode 620. The organic light-emitting diode D3 may further include a charge-generating layer 690 located between the first and second light-emitting units 630 and 730.

[0269] The organic light-emitting display device 500 includes a red pixel region RP, a green pixel region GP, ​​and a blue pixel region BP, and the organic light-emitting diode D3 is located in the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP.

[0270] The first electrode 610 may be a positive electrode, and the second electrode 620 may be a negative electrode. The first electrode 610 may be a reflective electrode, and the second electrode 620 may be a transmissive electrode.

[0271] The first light-emitting unit 630 includes a first light-emitting material layer 660.

[0272] Furthermore, the first light-emitting unit 630 may further include at least one of the first hole transport layer (lower hole transport layer) 650 located below the first light-emitting material layer 660 and the first electron transport layer (lower electron transport layer) 670 located above the first light-emitting material layer 660.

[0273] Furthermore, the first light-emitting unit 630 may further include a hole injection layer 640 located below the first hole transport layer 650. Also, the first light-emitting unit 630 may further include at least one of the following: a first electron-blocking layer (lower electron-blocking layer) 655 located between the first hole transport layer 650 and the first light-emitting material layer 660, and a first hole-blocking layer (lower hole-blocking layer) 675 located between the first light-emitting material layer 660 and the first electron transport layer 670.

[0274] The second light-emitting unit 730 includes a second light-emitting material layer 760. The second light-emitting material layer 760 includes a lower light-emitting material layer 762 located between the second electron-blocking layer 755 and the second hole-blocking layer 775, and an upper light-emitting material layer 764 located between the lower light-emitting material layer 762 and the second hole-blocking layer 775. One of the upper and lower light-emitting material layers 762, 764 is a red light-emitting material layer, and the other of the upper and lower light-emitting material layers 762, 764 is a green light-emitting material layer. For example, the upper light-emitting material layer 764 may be a red light-emitting material layer.

[0275] Furthermore, the second light-emitting unit 730 may further include at least one of the second hole transport layer (upper hole transport layer) 750 located below the second light-emitting material layer 760 and the second electron transport layer (upper electron transport layer) 770 located above the second light-emitting material layer 760.

[0276] Furthermore, the second light-emitting unit 730 may further include an electron injection layer 780 above the second electron transport layer 770. In this case, the electron injection layer 780 is located between the second electrode 620 and the second electron transport layer 770.

[0277] Furthermore, the second light-emitting unit 730 may further include at least one of the following: a second electron-blocking layer (upper electron-blocking layer) 755 located between the second hole transport layer 750 and the second light-emitting material layer 760, and a second hole-blocking layer (upper hole-blocking layer) 775 located between the second light-emitting material layer 760 and the second electron transport layer 770.

[0278] The hole injection layer 640 may contain the aforementioned hole injection material and may have a thickness of 10 to 100 nm. The first and second hole transport layers 650 and 750, respectively, may contain the aforementioned hole transport material and may have a thickness of 30 nm to 150 nm, preferably 50 nm to 120 nm.

[0279] The first and second electron transport layers 680 and 770, respectively, may contain the aforementioned electron transport material and may have a thickness of 10 nm to 100 nm, preferably 10 nm to 50 nm.

[0280] The electron injection layer 780 may contain the aforementioned electron injection material and may have a thickness of 0.1 to 10 nm, preferably 0.5 to 5 nm.

[0281] In Figure 6, the second electron transport layer 770 and the electron injection layer 780 are formed separately. Alternatively, a single-layer electron transport-injection layer that performs both electron transport and electron injection roles can be formed. In this case, the electron transport-injection layer may contain an electron transport material and an electron injection material, and may have a thickness of 10 to 50 nm. For example, the electron transport-injection layer may contain a compound of chemical formula 7 and a compound of chemical formula 8. In this case, the weight ratio of the compound of chemical formula 7 and the weight ratio of the compound of chemical formula 8 in the electron transport-injection layer may be the same.

[0282] The first and second electron-blocking layers 655 and 755 may each contain the aforementioned electron-blocking material, and the first and second hole-blocking layers 675 and 775 may each contain the aforementioned hole-blocking material.

[0283] The charge generation layer (CGL) 690 is located between the first light-emitting unit 630 and the second light-emitting unit 730. The charge generation layer 690 includes an N-type charge generation layer (N-CGL) 710 located adjacent to the first light-emitting unit 630 and a P-type charge generation layer (P-CGL) 720 located adjacent to the second light-emitting unit 730. The N-type charge generation layer 710 injects electrons into the first light-emitting unit 630, and the P-type charge generation layer 720 injects holes into the second light-emitting unit 730.

[0284] The N-type charge generation layer 710 may be made of the aforementioned N-type charge generation material, and the P-type charge generation layer 720 may be made of the aforementioned P-type charge generation material.

[0285] The first luminescent material layer 660 may be a blue (B) luminescent material layer. The first luminescent material layer 660 may contain a blue host and a blue dopant. For example, in the first luminescent material layer 660, the blue dopant may be present in an amount of 1 to 40% by weight, preferably 1 to 20% by weight, and more preferably 1 to 10% by weight.

[0286] The blue host is mCP, mCP-CN, mCBP, CBP-CN, CBP, 9-(3-(9H-carbazol-9-yl)phenyl)-3-(diphenylphosphoryl)-9H-carbazole (9-(3-(9H-Carbazol-9-yl)phenyl)-3-(diphenylphosphoryl)-9H-carbazole, mCPPO1), 3,5-di(9H-carbazol-9-yl)biphenyl (3,5-Di(9H-carbazol-9-yl)biphenyl; Ph-mCP), TSPO1, 9-(3'-(9H-carbazol-9-yl-[1,1'-biphenyl]-3-yl)-9H-pyrido[2,3-b]indole (9-(3'-(9H-carbazol-9- yl)-[1,1'-biphenyl]-3-yl)-9H-pyrido[2,3-b]indole (CzBPCb), bis(2-methylphenyl)diphenylsilane (UGH-1), 1,4-bis(triphenylsilyl)benzene (UGH-2), 1,3-bis(triphenylsilyl)benzene (UGH-3), 9,9-spirobifluoren-2-yl-diphenylphosphine oxide The blue host substance may be any one of the following: oxide (SPPO1), 9,9'-(5-triphenylsilyl)-1,3-phenylene)bis(9H-carbazole); SimCP.

[0287] Additionally, the blue dopants are perylene, 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), and 4,4'-bis[4-(di-p-tolylamino)styryl]stilbene. 4,4'-Bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 2,5,8,11-Tetra-tert-butylperylene (TBPe), Bepp2, 9-(9-Phenylcarbazole-3-yl)-10-(naphthalene-1-yl)anthracene (9-(9-Phenylcarbazole-3-yl)-10-(naphthalene-1-yl)a nthracene (PCAN), mer-Tris(1-phenyl-3-methylimidazolin-2-yllidene-C,C(2)'iridium(III), mer-Ir(pmi)3), fac-Tris(1,3-diphenyl-benziimidazolin-2-yllidene-C,C(2)'iridium(III)(fac-Tris(1,3-diphenyl-benzi midazolin-2-ylidene-C,C(2)'iridium(III), fac-Ir(dpbic)3), bis(3,4,5-trifluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III);Ir(tfpd)2pic), tris(2-(4,6-difluorophenyl)pyridine)iridium(III);The blue dopant material may be, but is not limited to, one of the following: Ir(Fppy)3) or bis[2-(4,6-difluorophenyl)pyridinato-C2,N](picolinato)iridium(III); Firpic.

[0288] In one embodiment, the blue light-emitting material layer may contain a host which is an anthracene derivative and a dopant which is a boron derivative.

[0289] At least one of the lower light-emitting material layer 762 and the upper light-emitting material layer 764 of the second light-emitting material layer 760 contains a first compound which is an organometallic compound represented by chemical formula 1.

[0290] For example, the upper luminescent material layer 764, which is a red luminescent material layer, may contain a first compound (red dopant) which is an organometallic compound represented by chemical formula 1. The upper luminescent material layer 764 may further contain a second compound which is a red host. In the upper luminescent material layer 764, which is a red luminescent material layer, the first compound has a smaller weight ratio than the second compound. For example, in the upper luminescent material layer 764, which is a red luminescent material layer, the first compound may be present in an amount of 1 to 40% by weight, preferably 1 to 20% by weight, and more preferably 1 to 10% by weight.

[0291] The second compound (red host) may be, but is not limited to, the aforementioned red host substance.

[0292] For example, the lower luminescent material layer 762, which is a green luminescent material layer, may contain a first compound (green dopant) which is an organometallic compound represented by chemical formula 1. The lower luminescent material layer 762, which is a green luminescent material layer, may further contain a second compound which is a green host. In the lower luminescent material layer 762, which is a green luminescent material layer, the first compound has a smaller weight ratio than the second compound. For example, in the lower luminescent material layer 762, which is a green luminescent material layer, the first compound may be present in an amount of 1 to 40% by weight, preferably 1 to 20% by weight, and more preferably 1 to 10% by weight.

[0293] The second compound (green host) may be, but is not limited to, the aforementioned green host substance.

[0294] When both the lower light-emitting material layer 762, which is a green light-emitting material layer, and the upper light-emitting material layer 764, which is a red light-emitting material layer, contain the first compound, which is an organometallic compound of the present invention, the first compound in the lower light-emitting material layer 762 (green dopant) and the first compound in the upper light-emitting material layer 764 (red dopant) have differences in the auxiliary ligand of chemical formula 1 and emit light of different wavelengths.

[0295] In contrast, the upper luminescent material layer 764, which is a red luminescent material layer, may contain a red dopant instead of the organometallic compound of chemical formula 1. In this case, the red dopant may contain at least one of a red phosphorescent material, a red fluorescent material, and a red delayed fluorescent material. For example, the red dopant may be, but is not limited to, the red dopant material described above.

[0296] Figure 6 shows that the first light-emitting unit 630 includes a blue light-emitting material layer, and the second light-emitting unit 730 includes a red light-emitting material layer and a green light-emitting material layer. Alternatively, the first light-emitting unit 630 may include a red light-emitting material layer and a green light-emitting material layer, and the second light-emitting unit 730 may include a blue light-emitting material layer.

[0297] In Figure 6, the second light-emitting material layer 760 has a double-layer structure consisting of a lower light-emitting material layer 762, which is one of the red or green light-emitting material layers, and a green light-emitting material layer 764, which is the other of the red or green light-emitting material layers. Alternatively, the second light-emitting material layer 760 may further include a yellow-green light-emitting material layer located between the lower light-emitting material layer 762 and the upper light-emitting material layer 764, thus having a triple-layer structure.

[0298] In Figure 6, the organic light-emitting layer 615 has a double-stack structure including a first light-emitting unit 630 which includes a first light-emitting material layer 660 which is a blue light-emitting material layer, and a second light-emitting unit 730 which includes a lower light-emitting material layer 762 which is one of the red or green light-emitting material layers, and a green light-emitting material layer 764 which is the other of the red or green light-emitting material layers. Alternatively, the organic light-emitting layer 615 may have a triple-stack structure, further including a third light-emitting unit which includes a blue light-emitting material layer and is located between the second light-emitting unit 730 and the second electrode 620. In this case, a charge generation layer is included between the second light-emitting unit 730 and the third light-emitting unit. Furthermore, the second light-emitting material layer 760 may have a triple-layer structure, further including a yellow-green light-emitting material layer located between the lower light-emitting material layer 762 which is one of the red or green light-emitting material layers, and the green light-emitting material layer 764 which is the other of the red or green light-emitting material layers.

[0299] As described above, the organic light-emitting diode D3 includes a first light-emitting unit 630 containing a first light-emitting material layer 660 which is a blue light-emitting material layer, and a second light-emitting unit 730 containing a red light-emitting material layer and a green light-emitting material layer. Therefore, the organic light-emitting diode D3 can realize white (W) light emission. The organic light-emitting diode D3 can be used in an organic light-emitting display device 500 which includes a color filter layer 580 to realize color images.

[0300] In the organic light-emitting diode D3 of the present invention, at least one of the lower and upper light-emitting material layers 762 and 764 of the second light-emitting material layer 760 contains the organometallic compound of the present invention. Therefore, the luminous efficiency and lifespan of the organic light-emitting diode D3 are improved.

[0301] Figure 7 is a schematic cross-sectional view of an organic light-emitting diode according to a sixth embodiment of the present invention.

[0302] As shown in Figure 7, the organic light-emitting diode D4 according to the sixth embodiment of the present invention includes a first electrode 610 and a second electrode 620 facing each other, and an organic light-emitting layer 615 located between the first electrode 610 and the second electrode 620. The organic light-emitting layer 615 includes a first light-emitting unit 830 located between the first electrode 610 and the second electrode 620, a second light-emitting unit 930 located between the first light-emitting unit 830 and the second electrode 620, and a third light-emitting unit 1030 located between the second light-emitting unit 930 and the second electrode 620. The organic light-emitting diode D4 may further include a first charge generation layer 890 located between the first and second light-emitting units 830 and 930, and a second charge generation layer 990 located between the second and third light-emitting units 930 and 1030.

[0303] The organic light-emitting display device 500 includes a red pixel region RP, a green pixel region GP, ​​and a blue pixel region BP, and the organic light-emitting diode D4 is located in the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP.

[0304] The first electrode 610 may be a positive electrode, and the second electrode 620 may be a negative electrode. The first electrode 610 may be a reflective electrode, and the second electrode 620 may be a transmissive electrode.

[0305] The first light-emitting unit 830 includes a first light-emitting material layer 860.

[0306] Furthermore, the first light-emitting unit 830 may further include at least one of the first hole transport layer 850 located below the first light-emitting material layer 860 and the first electron transport layer 870 located above the first light-emitting material layer 860.

[0307] Furthermore, the first light-emitting unit 830 may further include a hole injection layer 840 located below the first hole transport layer 850. The first light-emitting unit 830 may also further include at least one of a first electron-blocking layer 855 located between the first hole transport layer 850 and the first light-emitting material layer 860, and a first hole-blocking layer 875 located between the first light-emitting material layer 860 and the first electron transport layer 870.

[0308] The second light-emitting unit 930 includes a second light-emitting material layer 960.

[0309] Furthermore, the second light-emitting unit 930 may further include at least one of a second hole transport layer 950 located below the second light-emitting material layer 960 and a second electron transport layer 970 located above the second light-emitting material layer 960.

[0310] Furthermore, the second light-emitting unit 930 may further include at least one of the following: a second electron-blocking layer 955 located between the second hole transport layer 950 and the second light-emitting material layer 960, and a second hole-blocking layer 975 located between the second light-emitting material layer 960 and the second electron transport layer 970.

[0311] The third light-emitting unit 1030 includes a third light-emitting material layer 1060.

[0312] Furthermore, the third light-emitting unit 1030 may further include a third hole transport layer 1050 located below the third light-emitting material layer 1060, and a third electron transport layer 1070 located above the third light-emitting material layer 1060.

[0313] Furthermore, the third light-emitting unit 1030 may further include an electron injection layer 1080 located above the third electron transport layer 1070. Additionally, the third light-emitting unit 1030 may further include at least one of the following: a third electron barrier layer 1055 located between the third hole transport layer 1050 and the third light-emitting material layer 1060, and a third hole barrier layer 1075 located between the third light-emitting material layer 1060 and the third electron transport layer 1070.

[0314] The hole injection layer 840 may contain the aforementioned hole injection material, and the first to third hole transport layers 850, 950, and 1050 may each contain the aforementioned hole transport material.

[0315] The first to third electron transport layers 870, 970, and 1070 may each contain the aforementioned electron transport material, and the electron injection layer 1080 may also contain the aforementioned electron injection material.

[0316] The first to third electron-blocking layers 855, 955, and 1055 may each contain the aforementioned electron-blocking material, and the first to third hole-blocking layers 875, 975, and 1075 may each contain the aforementioned hole-blocking material.

[0317] The first charge generation layer 890 is located between the first light-emitting unit 830 and the second light-emitting unit 930, and the second charge generation layer 990 is located between the second light-emitting unit 930 and the third light-emitting unit 1030. The first charge generation layer 890 includes a first N-type charge generation layer 910 located adjacent to the first light-emitting unit 830 and a first P-type charge generation layer 920 located adjacent to the second light-emitting unit 930. The second charge generation layer 990 includes a second N-type charge generation layer 1010 located close to the second light-emitting unit 930 and a second P-type charge generation layer 1020 located adjacent to the third light-emitting unit 1030. In this process, the first and second N-type charge generation layers 910 and 1010 inject electrons into the first and second light-emitting units 830 and 930, respectively, while the first and second P-type charge generation layers 920 and 1020 inject holes into the second and third light-emitting units 930 and 1030, respectively.

[0318] The first and second N-type charge generation layers 910 and 1010 may each contain the aforementioned N-type charge generation material, and the first and second P-type charge generation layers 920 and 1020 may each contain the aforementioned P-type charge generation material.

[0319] One of the first to third light-emitting material layers 860, 960, and 1060 is a red light-emitting material layer, another of the first to third light-emitting material layers 860, 960, and 1060 is a green light-emitting material layer, and the remaining one of the first to third light-emitting material layers 860, 960, and 1060 is a blue light-emitting material layer. Therefore, the organic light-emitting diode 500 can achieve white (W) light emission.

[0320] For example, the first light-emitting material layer 860 may be a red light-emitting material layer, the second light-emitting material layer 960 may be a green light-emitting material layer, and the third light-emitting material layer 1060 may be a blue light-emitting material layer.

[0321] In this case, at least one of the first luminescent material layer 860 and the second luminescent material layer 960 contains an organometallic compound represented by chemical formula 1.

[0322] For example, the first luminescent material layer 860, which is a red luminescent material layer, may contain a first compound red dopant, which is an organometallic compound represented by chemical formula 1. The first luminescent material layer 860 may further contain a second compound, which is a red host. In the first luminescent material layer 860, the first compound has a smaller weight ratio than the second compound. For example, in the first luminescent material layer 860, the first compound may be present in an amount of 1 to 40% by weight, preferably 1 to 20% by weight, and more preferably 1 to 10% by weight.

[0323] The second compound (red host) may be the red host substance described above.

[0324] The second luminescent material layer 960, which is a green luminescent material layer, may contain a first compound (green dopant) which is an organometallic compound represented by chemical formula 1. The second luminescent material layer 960 may further contain a second compound which is a green host. In the second luminescent material layer 960, the first compound has a smaller weight ratio than the second compound. For example, in the second luminescent material layer 960, the first compound may be present in an amount of 1 to 40% by weight, preferably 1 to 20% by weight, and more preferably 1 to 10% by weight.

[0325] The second compound (green host) may be the green host substance described above.

[0326] When both the first luminescent material layer 860, which is a red luminescent material layer, and the second luminescent material layer 960, which is a green luminescent material layer, contain the first compound, which is an organometallic compound of the present invention, the first compound (red dopant) in the first luminescent material layer 860 and the first compound (green dopant) in the second luminescent material layer 960 have differences in the auxiliary ligand of chemical formula 1 and emit light of different wavelengths.

[0327] In contrast, the second luminescent material layer 860, which is a red luminescent material layer, may contain a red dopant instead of the organometallic compound of chemical formula 1. In this case, the red dopant may contain at least one of a red phosphorescent material, a red fluorescent material, and a red delayed fluorescent material. For example, the red dopant may be the red dopant material described above.

[0328] The third light-emitting material layer 1060 may be a blue (B) light-emitting material layer. The third light-emitting material layer 1060 may contain a blue host and a blue dopant. For example, in the third light-emitting material layer 1060, the amount of blue dopant may be 1 to 40% by weight, preferably 1 to 20% by weight, and more preferably 1 to 10% by weight.

[0329] The blue host may be the blue host substance described above, and the blue dopant may be the blue dopant substance described above.

[0330] As described above, the organic light-emitting diode D4 includes a first light-emitting unit 830 containing a first light-emitting material layer 860 which is a red light-emitting material layer, a second light-emitting unit 930 containing a second light-emitting material layer 960 which is a green light-emitting material layer, and a third light-emitting unit 1030 containing a third light-emitting material layer 1060 which is a blue light-emitting material layer. Therefore, the organic light-emitting diode D4 can achieve white (W) light emission. The organic light-emitting diode D4 can be used in an organic light-emitting display device 500 which includes a color filter layer 580 to realize color images.

[0331] In the organic light-emitting diode D4 of the present invention, at least one of the first light-emitting material layer 860 and the second light-emitting material layer 960 contains the organometallic compound of the present invention. Therefore, the luminous efficiency and lifespan of the organic light-emitting diode D5 are improved.

[0332] Figure 8 is a schematic cross-sectional view of an organic light-emitting diode according to the seventh embodiment of the present invention.

[0333] As shown in Figure 8, the organic light-emitting diode D5 according to the eighth embodiment of the present invention includes a first electrode 610 and a second electrode 620 facing each other, and an organic light-emitting layer 615 located between the first electrode 610 and the second electrode 620, wherein the organic light-emitting layer 615 includes a first light-emitting unit 1130 located between the first electrode 610 and the second electrode 620, a second light-emitting unit 1230 located between the first light-emitting unit 1130 and the second electrode 620, and a third light-emitting unit 1330 located between the second light-emitting unit 1230 and the second electrode 620. The organic light-emitting diode D5 may further include a first charge generation layer 1190 located between the first and second light-emitting units 1130 and 1230, and a second charge generation layer 1290 located between the second and third light-emitting units 1230 and 1330.

[0334] The organic light-emitting display device 500 includes a red pixel region RP, a green pixel region GP, ​​and a blue pixel region BP, and the organic light-emitting diode D5 is located in the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP.

[0335] The first electrode 610 may be a positive electrode, and the second electrode 620 may be a negative electrode. The first electrode 610 may be a reflective electrode, and the second electrode 620 may be a transmissive electrode.

[0336] The first light-emitting unit 830 includes a first light-emitting material layer 860.

[0337] Furthermore, the first light-emitting unit 1130 may further include at least one of the first hole transport layer 1150 located below the first light-emitting material layer 1160 and the first electron transport layer 1170 located above the first light-emitting material layer 1160.

[0338] Furthermore, the first light-emitting unit 1130 may further include a hole injection layer 1140 located below the first hole transport layer 1150. The first light-emitting unit 1130 may also further include at least one of the following: a first electron-blocking layer 1155 located between the first hole transport layer 1150 and the first light-emitting material layer 1160, and a first hole-blocking layer 1175 located between the first light-emitting material layer 1160 and the first electron transport layer 1170.

[0339] The second light-emitting unit 1230 includes a second light-emitting material layer 1260.

[0340] Furthermore, the second light-emitting unit 1230 may further include at least one of a second hole transport layer 1250 located below the second light-emitting material layer 1260 and a second electron transport layer 1270 located above the second light-emitting material layer 1260.

[0341] Furthermore, the second light-emitting unit 1230 may further include at least one of the following: a second electron-blocking layer 1255 located between the second hole transport layer 1250 and the second light-emitting material layer 1260, and a second hole-blocking layer 1275 located between the second light-emitting material layer 1260 and the second electron transport layer 1270.

[0342] The third light-emitting unit 1330 includes a third light-emitting material layer 1360.

[0343] Furthermore, the third light-emitting unit 1330 may further include a third hole transport layer 1350 located below the third light-emitting material layer 1360, and a third electron transport layer 1370 located above the third light-emitting material layer 1360.

[0344] Furthermore, the third light-emitting unit 1330 may further include an electron injection layer 1380 located above the third electron transport layer 1370. Additionally, the third light-emitting unit 1330 may further include at least one of the following: a third electron barrier layer 1355 located between the third hole transport layer 1350 and the third light-emitting material layer 1360, and a third hole barrier layer 1375 located between the third light-emitting material layer 1360 and the third electron transport layer 1370.

[0345] The hole injection layer 1140 may contain the aforementioned hole injection material, and the first to third hole transport layers 1150, 1250, and 1350 may each contain the aforementioned hole transport material.

[0346] The first to third electron transport layers 1170, 1270, and 1370 may each contain the aforementioned electron transport material, and the electron injection layer 1380 may also contain the aforementioned electron injection material.

[0347] Each of the first to third electron-blocking layers 1155, 1255, and 1355 may contain the aforementioned electron-blocking material, and each of the first to third hole-blocking layers 1175, 1275, and 1375 may contain the aforementioned hole-blocking material.

[0348] The first charge generation layer 1190 is located between the first light-emitting unit 1130 and the second light-emitting unit 1230, and the second charge generation layer 1290 is located between the second light-emitting unit 1230 and the third light-emitting unit 1330. The first charge generation layer 1190 includes a first N-type charge generation layer 1210 located adjacent to the first light-emitting unit 1130 and a first P-type charge generation layer 1220 located adjacent to the second light-emitting unit 1230. The second charge generation layer 1290 includes a second N-type charge generation layer 1310 located close to the second light-emitting unit 1230 and a second P-type charge generation layer 1320 located adjacent to the third light-emitting unit 1330. In this process, the first and second N-type charge generation layers 1210 and 1310 inject electrons into the first and second light-emitting units 1130 and 1230, respectively, while the first and second P-type charge generation layers 1220 and 1320 inject holes into the second and third light-emitting units 1230 and 1330, respectively.

[0349] The first and second N-type charge generation layers 1210 and 1310 may each contain the aforementioned N-type charge generation material, and the first and second P-type charge generation layers 1220 and 1320 may each contain the aforementioned P-type charge generation material.

[0350] The first luminescent material layer 1160 and the third luminescent material layer 1360 may each be a blue luminescent material layer. The first luminescent material layer 1160 and the third luminescent material layer 1360 may each contain a blue host and a blue dopant. The blue host of the first luminescent material layer 1160 and the blue host of the third luminescent material layer 1360 may be the same or different, and the blue dopant of the first luminescent material layer 1160 and the blue dopant of the third luminescent material layer 1360 may be the same or different. For example, in the first luminescent material layer 1160 and the third luminescent material layer 1360, the blue dopant may be present in an amount of 1 to 40% by weight, preferably 1 to 20% by weight, and more preferably 1 to 10% by weight.

[0351] The blue host may be the blue host substance described above, and the blue dopant may be the blue dopant substance described above.

[0352] The second light-emitting material layer 1260 includes a lower light-emitting material layer 1262 located between the second electron-blocking layer 1255 and the second hole-blocking layer 1275, and an upper light-emitting material layer 1264 located between the lower light-emitting material layer 1262 and the second hole-blocking layer 1275. One of the upper and lower light-emitting material layers 1262, 1264 is a red light-emitting material layer, and the other of the upper and lower light-emitting material layers 1262, 1264 is a green light-emitting material layer. For example, the lower light-emitting material layer 1262 may be a red light-emitting material layer.

[0353] At least one of the lower light-emitting material layer 1262 and the upper light-emitting material layer 1264 of the second light-emitting material layer 1260 contains a first compound which is an organometallic compound represented by chemical formula 1.

[0354] For example, the lower luminescent material layer 1262, which is a red luminescent material layer, may contain a first compound (red dopant) which is an organometallic compound represented by chemical formula 1. The lower luminescent material layer 1262 may further contain a second compound which is a red host. In the lower luminescent material layer 1262, which is a red luminescent material layer, the first compound has a smaller weight ratio than the second compound. For example, in the lower luminescent material layer 1262, which is a red luminescent material layer, the first compound may be present in an amount of 1 to 40% by weight, preferably 1 to 20% by weight, and more preferably 1 to 10% by weight.

[0355] The second compound (red host) may be the red host substance described above.

[0356] For example, the upper luminescent material layer 1264, which is a green luminescent material layer, may contain a first compound (green dopant) which is an organometallic compound represented by chemical formula 1. Furthermore, the upper luminescent material layer 1264, which is a green luminescent material layer, may further contain a second compound which is a green host. In the upper luminescent material layer 1264, which is a green luminescent material layer, the first compound has a smaller weight ratio than the second compound. For example, in the upper luminescent material layer 1264, which is a green luminescent material layer, the first compound may be present in an amount of 1 to 40% by weight, preferably 1 to 20% by weight, and more preferably 1 to 10% by weight.

[0357] The second compound (green host) may be the green host substance described above.

[0358] When both the lower light-emitting material layer 1262, which is a red light-emitting material layer, and the upper light-emitting material layer 1264, which is a green light-emitting material layer, contain the first compound, which is an organometallic compound of the present invention, the first compound in the lower light-emitting material layer 1262 (red dopant) and the first compound in the upper light-emitting material layer 1264 (green dopant) have differences in the auxiliary ligand of chemical formula 1 and emit light of different wavelengths.

[0359] In contrast, the lower luminescent material layer 1262, which is the red luminescent material layer, may contain a red dopant instead of the organometallic compound of chemical formula 1. In this case, the red dopant may contain at least one of a red phosphorescent material, a red fluorescent material, and a red delayed fluorescent material. For example, the red dopant may be the red dopant material described above.

[0360] In Figure 8, the second light-emitting material layer 1260 has a double-layer structure consisting of a lower light-emitting material layer 1262 which is a red light-emitting material layer and an upper light-emitting material layer 1264 which is a green light-emitting material layer.

[0361] In contrast, the second light-emitting material layer 1260 may also include a yellow-green light-emitting material layer located between the lower light-emitting material layer 1262 and the upper light-emitting material layer 1264, thus having a triple-layer structure.

[0362] The yellow-green luminescent material layer may contain an organometallic compound represented by chemical formula 1 (yellow-green dopant). The yellow-green luminescent material layer may further contain a yellow-green host. For example, the yellow-green luminescent material layer may contain 1 to 40% by weight, preferably 1 to 20% by weight, and more preferably 1 to 10% by weight of the yellow-green dopant.

[0363] In contrast, the yellow-green luminescent material layer may also contain a yellow-green dopant instead of an organometallic compound of chemical formula 1. In this case, the yellow-green dopant may contain at least one of a yellow-green phosphorescent material, a yellow-green fluorescent material, and a yellow-green delayed fluorescent material.For example, the yellow-green dopants are 5,6,11,12-Tetraphenylnaphthalene (Rubrene), 2,8-Di-tert-butyl-5,11-bis(4-tert-butylphenyl)-6,12-diphenyltetracene (TBRb), and bis(2-phenylbenzothiazo Iridium(III)(acetylacetonate)(Bis(2-phenylbenzothiazolato)(acetylacetonate)irdium(III);Ir(BT)2(acac)), Bis(2-(9,9-diethyl-fluoren-2-yl)-1-phenyl-1H-benzo[d]imdazolato)(acetylacetonate)irdium(III)(Bis(2-(9,9-diethytl-fluoren-2-yl)-1-phenyl-1H-benzo[d]imd iazolato)(acetylacetonate)iridium(III);Ir(fbi)2(acac)), bis(2-phenylpyridine)(3-(pyridine-2-yl)-2H-chromen-2-onate)iridium(III)(Bis(2-phenylpyridine)(3-(pyridine-2-yl)-2H-chromen-2-onate)iridium(III);fac-Ir(ppy)2Pc), bis(2-(2,4-difluorophenyl)quinoline)(picolinate) It may also be one of the following: iridium(III) (Bis(2-(2,4-difluorophenyl)quinoline)(picolinate)iridium(III);FPQIrpic) or bis(4-phenylthieno[3,2-c]pyridinato-N,C2'(acetylacetonate)iridium(III) (Bis(4-phenylthieno[3,2-c]pyridinato-N,C2')(acetylacetonate)iridium(III);PO-01).

[0364] As described above, the organic light-emitting diode D5 includes first and third light-emitting units 1130 and 1330, which include first and third light-emitting material layers 1160 and 1360, which are blue light-emitting material layers, and a second light-emitting unit 1230, which includes a red light-emitting material layer and a green light-emitting material layer. Therefore, the organic light-emitting diode D5 can achieve white (W) light emission. The organic light-emitting diode D5 can be used in an organic light-emitting display device 500 which includes a color filter layer 580 to realize color images.

[0365] In the organic light-emitting diode D5 of the present invention, at least one of the lower and upper light-emitting material layers 1262 and 1264 of the second light-emitting material layer 760 contains the organometallic compound of the present invention. Therefore, the luminous efficiency and lifespan of the organic light-emitting diode D5 are improved.

[0366] Although preferred embodiments of the present invention have been described above with reference to the present invention, a person ordinary in the art will understand that the present invention can be modified and altered in various ways without departing from the technical idea and scope of the present invention as described in the following claims. [Explanation of symbols]

[0367] 100, 500 Organic Light-Emitting Display Devices D1, D2, D3, D4, D5 Organic Light-Emitting Diodes 210, 610 1st electrode 230, 620 2nd electrode 220, 615 Organic light-emitting layer 260, 350, 370, 660, 760, 860, 960, 1060, 1160, 1260, 1360 Luminescent material layer 380, 690, 890, 990, 1190, 1290 charge generation layer

Claims

1. An organometallic compound characterized by being one of the compounds of the following chemical formula 3.

2. First electrode and, A second electrode facing the first electrode, A first light-emitting unit is located between the first electrode and the second electrode and includes a first light-emitting material layer, The first light-emitting material layer comprises an organic light-emitting diode containing the organometallic compound described in claim 1.

3. The first light-emitting material layer comprises a first host and a first dopant. The organic light-emitting diode according to claim 2, characterized in that the first dopant is the organometallic compound.

4. A second light-emitting unit comprising a second light-emitting material layer and located between the first light-emitting unit and the first electrode, The organic light-emitting diode according to claim 3, further comprising a first charge generation layer located between the first light-emitting unit and the second light-emitting unit.

5. The organic light-emitting diode according to claim 4, characterized in that the second light-emitting material layer contains a blue dopant.

6. The organic light-emitting diode according to claim 5, characterized in that the first light-emitting unit further includes a third light-emitting material layer located below or above the first light-emitting material layer.

7. The organic light-emitting diode according to claim 6, characterized in that the third light-emitting material layer contains a red dopant.

8. A third light-emitting unit, located between the first light-emitting unit and the second electrode, and including a third light-emitting material layer; The organic light-emitting diode according to claim 5, further comprising: a second charge generation layer located between the first light-emitting unit and the third light-emitting unit;

9. The organic light-emitting diode according to claim 8, characterized in that the third light-emitting material layer contains a red dopant.

10. A third light-emitting unit is located between the first light-emitting unit and the second electrode and includes a third light-emitting material layer, The present invention further includes a second charge generation layer located between the first light-emitting unit and the third light-emitting unit, The organic light-emitting diode according to claim 5, characterized in that the first light-emitting unit further includes a fourth light-emitting material layer located below or above the first light-emitting material layer.

11. The third luminescent material layer contains a blue dopant, The organic light-emitting diode according to claim 10, characterized in that the fourth light-emitting material layer contains a green dopant.

12. circuit board and Located on the upper part of the substrate, the organic light-emitting diode includes a first electrode, a second electrode facing the first electrode, and a first light-emitting unit located between the first electrode and the second electrode, which includes a first light-emitting material layer. The encapsulation layer covering the organic light-emitting diode is included, The first light-emitting material layer comprises an organometallic compound as described in claim 1, in an organic light-emitting device.

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