Organometallic compounds and organic light emitting diode comprising the same

Abstract

The present invention provides a novel organometallic compound comprising a fused ring structure in which the main ligand (LA) includes a thiophene group, and by including this in the dopant material of the phosphorescent light-emitting layer of an organic light-emitting device, the performance of the organic light-emitting device, such as driving voltage, luminous efficiency, and lifespan, can be improved.

Description

Technology Field

[0001] The present invention relates to organometallic compounds, and more specifically, to organometallic compounds having phosphorescent properties and organic light-emitting diodes containing the same. Background Technology

[0003] Interest in display devices is growing as they are applied in various fields. As one of these display devices, the technology of organic light-emitting display devices, including organic light-emitting diodes (OLEDs), is developing rapidly.

[0004] Organic light-emitting diodes (OLEDs) are devices that emit light by injecting charges into a light-emitting layer formed between an anode and a cathode, causing electrons and holes to pair up to form excitons. Compared to conventional display technologies, OLEDs offer several advantages, including low-voltage operation, relatively low power consumption, and excellent color reproduction. Furthermore, they allow for the application of flexible substrates, enabling diverse applications and the ability to freely adjust the size of the display device. The problem to be solved

[0006] Organic light-emitting diodes (OLEDs) have superior viewing angles and contrast ratios compared to liquid crystal displays (LCDs), and because they do not require a backlight, they can be lightweight and ultra-thin. An organic light-emitting diode is formed by arranging a plurality of organic layers, such as a hole injection layer, a hole transport layer, a hole transport assist layer, an electron blocking layer, a light-emitting layer, and an electron transport layer, between a cathode (electron injection electrode) and an anode (hole injection electrode).

[0007] In this organic light-emitting diode structure, when a voltage is applied between the two electrodes, electrons and holes are injected from the cathode and anode, respectively, and excitons generated in the light-emitting layer fall to the ground state and emit light.

[0008] Organic materials used in organic light-emitting diodes (OLEDs) can be broadly classified into light-emitting materials and charge transport materials. Light-emitting materials are a critical factor in determining the luminous efficiency of OLEDs; they must possess high quantum efficiency, excellent electron and hole mobility, and exist uniformly and stably within the light-emitting layer. Light-emitting materials are classified into blue, red, and green types based on the color of the emitted light, and they are used as hosts or dopants to increase color purity and enhance luminous efficiency through energy transfer.

[0009] Recently, there has been a trend of using phosphorescent materials more than fluorescent materials in the emissive layer. This is because, in the case of fluorescent materials, only about 25% of the singlets among the excitons formed in the emissive layer are used to produce light, and 75% of the triplets are mostly lost as heat, whereas phosphorescent materials have a light emission mechanism that converts both singlets and triplets into light.

[0010] Conventionally, organometallic compounds have been used as phosphorescent materials in organic light-emitting diodes, and there is a continuous demand for research and development of phosphorescent materials to solve the problems of their low efficiency and lifespan.

[0011] Accordingly, the objective of the present invention is to provide an organometallic compound capable of improving driving voltage, efficiency, and lifespan, and an organic light-emitting diode in which the same is applied to an organic light-emitting layer.

[0012] The objects of the present invention are not limited to those mentioned above, and other unmentioned objects and advantages of the present invention may be understood from the following description and will be more clearly understood by the embodiments of the present invention. Furthermore, it will be readily apparent that the objects and advantages of the present invention can be realized by the means and combinations thereof set forth in the claims. means of solving the problem

[0015] To solve the above problem, the present invention may provide an organometallic compound having a novel structure represented by the following chemical formula 1, an organic light-emitting element including the same as a light-emitting layer dopant, and an organic light-emitting display device including the organic light-emitting element.

[0016] [Chemical Formula 1] Ir(L A ) m (L B ) n

[0017] In the above chemical formula 1,

[0018] L A may be one selected from the group consisting of the following chemical formulas 2-1 to 2-6, and L B may be a bidentate ligand represented by the following chemical formula 3, m is 1, 2, or 3, n is 0, 1, or 2, and the sum of m and n may be 3, and

[0019] [Chemical Formula 2-1]

[0020] [Chemical Formula 2-2] ,

[0021] [Chemical Formula 2-3] ,

[0022] [Chemical Formula 2-4] ,

[0023] [Chemical Formula 2-5] ,

[0024] [Chemical Formula 2-6] ,

[0025] [Chemical Formula 3]

[0026] In the above chemical formulas 2-1 to 2-6,

[0027] X can each be independently selected from the group consisting of carbon, oxygen, nitrogen, and sulfur, and R 1-1 , R 1-2 , R1-3 , R 1-4 , R 2-1 , R 2-2 , R 3-1 , R 3-2 , R 4-1 and R 4-2 Each may be independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0028] The above R 1-1 , R 1-2, R 1-3 , R 1-4 , R 2-1 , R 2-2 , R 3-1 , R 3-2 , R 4-1 and R 4-2 Two adjacent functional groups can combine to form a ring structure. Effects of the invention

[0030] By applying the organometallic compound according to the present invention to the phosphorescent light-emitting layer dopant of an organic light-emitting device, the driving voltage, efficiency, and lifespan characteristics of the organic light-emitting device can be improved.

[0031] The effects of this specification are not limited to those mentioned above, and other unmentioned effects will be clearly understood by those skilled in the art from the description below. Brief explanation of the drawing

[0033] FIG. 1 is a cross-sectional view schematically illustrating an organic light-emitting device in which an organometallic compound according to an exemplary embodiment of the present invention is applied to a light-emitting layer. FIG. 2 is a cross-sectional view schematically illustrating an organic light-emitting diode having a tandem structure with two light-emitting parts according to an exemplary embodiment of the present invention, and comprising an organometallic compound represented by Formula 1 of the present invention. FIG. 3 is a cross-sectional view schematically illustrating an organic light-emitting diode having a tandem structure with three light-emitting parts according to an exemplary embodiment of the present invention, and comprising an organometallic compound represented by Formula 1 of the present invention. FIG. 4 is a cross-sectional view schematically illustrating an organic light-emitting display device to which an organic light-emitting element according to an exemplary embodiment of the present invention is applied. Specific details for implementing the invention

[0034] The aforementioned objectives, features, and advantages are described in detail below with reference to the attached drawings, thereby enabling those skilled in the art to easily implement the technical concept of the present invention. In describing the present invention, detailed descriptions of known technologies related to the present invention are omitted if it is determined that such descriptions would unnecessarily obscure the essence of the invention. Hereinafter, preferred embodiments according to the present invention will be described in detail with reference to the attached drawings. In the drawings, the same reference numerals are used to indicate the same or similar components.

[0035] In describing this specification, if it is determined that a detailed description of related prior art could unnecessarily obscure the gist of this specification, such detailed description is omitted.

[0036] Where terms such as 'includes,' 'has,' 'consists of,' or 'arranges' are used for components below, other parts may be added unless 'only' is used. Where a component is expressed in the singular, it includes cases where it is in the plural unless specifically stated otherwise.

[0037] In interpreting the components below, they shall be interpreted to include a margin of error even without separate explicit notation.

[0038] In the following, the statement that any configuration is placed on the "upper (or lower)" of a component or on the "upper (or lower)" of a component may mean not only that any configuration is placed in contact with the upper (or lower) surface of said component, but also that another configuration may be interposed between said component and any configuration placed on (or below) said component.

[0039] In this specification, the phrase “adjacent functional groups combine to form a ring structure” means that adjacent functional groups combine to form a substituted or unsubstituted alicyclic ring structure (cycloalkyl group), a substituted or unsubstituted aromatic ring structure (aryl group), or a ring structure having both substituted or unsubstituted aliphatic and aromatic groups (alkylaryl group or arylalkyl group). An “adjacent functional group” may mean a functional group substituted on an atom directly connected to the atom on which the functional group is substituted, a functional group located stereostructurally closest to the substituent, or another functional group substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring structure and two functional groups substituted on the same carbon in an aliphatic ring may be interpreted as “adjacent functional groups.”

[0041] Hereinafter, the structure and preparation examples of an organometallic compound according to the present invention and an organic light-emitting diode containing the same will be described.

[0043] Conventionally, organometallic compounds have been used as dopants for phosphorescent light-emitting layers. For example, 2-phenylpyridine and 2-phenylquinoline structures, in which a condensation ring is introduced to the pyridine portion of the 2-phenylpyridine structure, are known as the main ligand structures of organometallic compounds. However, these conventional light-emitting dopants have limitations in improving the efficiency and lifespan of organic light-emitting devices, so it was necessary to develop novel light-emitting dopant materials. Accordingly, the inventors have derived a light-emitting dopant material capable of further improving the efficiency and lifespan of organic light-emitting devices and have completed the present invention.

[0045] Specifically, an organometallic compound according to one embodiment of the present invention may be represented by the following Chemical Formula 1, wherein L is the main ligand of Chemical Formula 1. A The structure is a fusion ring of thiophene having a sulfur (S) atom in the carbon (C) connected portion of the two rings connected to the central coordination metal Ir (iridium), and depending on the connection position and orientation of the thiophene fusion ring, it can be represented as one of the following chemical formulas 2-1 to 2-6. The inventors have experimentally confirmed that including an organometallic compound represented by chemical formula 1 in the dopant material of the phosphorescent light-emitting layer of an organic light-emitting device has excellent effects in increasing the luminous efficiency and lifespan of the organic light-emitting device and lowering the driving voltage, and have completed the present invention.

[0046] [Chemical Formula 1] Ir(L A ) m (L B ) n

[0047] In the above chemical formula 1,

[0048] L A may be one selected from the group consisting of the following chemical formulas 2-1 to 2-6, and L Bmay be a bidentate ligand represented by the following chemical formula 3, wherein m and n are the number of ligands bound to Ir (iridium), m is 1, 2, or 3, n is 0, 1, or 2, and the sum of m and n may be 3.

[0049] [Chemical Formula 2-1]

[0050] [Chemical Formula 2-2] ,

[0051] [Chemical Formula 2-3] ,

[0052] [Chemical Formula 2-4] ,

[0053] [Chemical Formula 2-5] ,

[0054] [Chemical Formula 2-6] ,

[0055] [Chemical Formula 3]

[0056] In the above chemical formulas 2-1 to 2-6,

[0057] X can each be independently selected from the group consisting of carbon, oxygen, nitrogen, and sulfur, and R 1-1 , R 1-2 , R 1-3 , R 1-4 , R 2-1 , R 2-2 , R 3-1 , R 3-2 , R 4-1 and R 4-2 Each may be independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0058] The above R 1-1 , R 1-2, R 1-3 , R 1-4 , R 2-1 , R 2-2 , R 3-1 , R 3-2 , R 4-1 and R 4-2 Two adjacent functional groups can combine to form a ring structure.

[0060] In an organometallic compound according to one embodiment of the present invention, a bidentate ligand can be applied as an auxiliary ligand to the central coordination metal. The bidentate ligand of the present invention includes an electron donor, thereby increasing the ratio of metal-to-ligand charge transfer (MLCT), and when applied to an organic light-emitting diode, improved luminescence characteristics such as high luminescence efficiency and high external quantum efficiency can be realized.

[0061] A preferred auxiliary ligand of the present invention may be a bidentate ligand represented by the above formula 3, and specifically, may be one selected from the group consisting of the following formulas 4 and 5.

[0062] [Chemical Formula 4] ,

[0063] [Chemical Formula 5] ,

[0064] In the above chemical formula 4, R 5-1 , R 5-2 , R 5-3 , R 5-4 , R 6-1 , R 6-2 , R 6-3 and R 6-4 Each may independently be one selected from the group consisting of hydrogen, deuterium, C1-C5 straight-chain alkyl groups, and C1-C5 branched-chain alkyl groups, and R 5-1 , R 5-2 , R 5-3 , R 5-4 , R6-1 , R 6-2 , R 6-3 and R 6-4 Among them, two adjacent functional groups can combine to form a ring structure, and

[0065] In the above chemical formula 5, R7, R8 and R9 may each be independently selected from the group consisting of hydrogen, deuterium, C1–C5 straight-chain alkyl groups and C1–C5 branched alkyl groups, and R7, R8 and Two adjacent functional groups among R9s can bond with each other to form a ring structure, and

[0066] The above C1-C5 straight-chain alkyl group or C1-C5 branched-chain alkyl group may be substituted with one or more selected from the group consisting of deuterium and halogen elements.

[0068] An organometallic compound according to one embodiment of the present invention may have a heteroleptic or homoleptic structure, for example, a heteroleptic structure in which m is 1 and n is 2 in the above formula 1; a heteroleptic structure in which m is 2 and n is 1; or a homoleptic structure in which m is 3 and n is 0.

[0070] A specific example of the compound represented by Formula 1 of the present invention may be one selected from the group consisting of the following compounds 1 to 540, but is not limited thereto as long as it falls within the definition of Formula 1.

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0099] According to one embodiment of the present invention, the organometallic compound represented by Formula 1 of the present invention can be used as a red phosphorescent material or a green phosphorescent material, and preferably as a green phosphorescent material.

[0101] Referring to FIG. 1 according to one embodiment of the present invention, an organic light-emitting element (100) may be provided, comprising: a first electrode (110); a second electrode (120) facing the first electrode (110); and an organic layer (130) disposed between the first electrode (110) and the second electrode (120). The organic layer (130) comprises a light-emitting layer (160), the light-emitting layer (160) comprises a host (160') and a dopant (160"), and the dopant (160") may comprise an organometallic compound represented by Chemical Formula 1. Additionally, in the organic light-emitting diode (100), the organic layer (130) disposed between the first electrode (110) and the second electrode (120) may have a structure comprising, sequentially from the first electrode (110), a hole injection layer (140, hole injection layer; HIL), a hole transport layer (150, hole transfer layer; HTL), an emission material layer (160, emission material layer, EML), an electron transport layer (170, electron transfer layer; ETL), and an electron injection layer (180, electron injection layer, EIL). The second electrode (120) may be formed on the electron injection layer (180), and a protective film (not shown) may be formed thereon.

[0103] Additionally, although not illustrated in FIG. 1, a hole transport auxiliary layer may be further added between the hole transport layer (150) and the light-emitting layer (160). The hole transport auxiliary layer includes a compound with good hole transport characteristics and controls the hole injection characteristics by reducing the HOMO energy level difference between the hole transport layer (150) and the light-emitting layer (160), thereby reducing the accumulation of holes at the interface between the hole transport auxiliary layer and the light-emitting layer (160) and reducing the quenching phenomenon in which excitons are extinguished by polarons at the interface. Accordingly, the degradation of the device is reduced and the device is stabilized, thereby improving efficiency and lifespan.

[0105] The first electrode (110) may be an anode and may be made of a conductive material such as ITO, IZO, tin oxide, or zinc oxide, which has a relatively large work function value, but is not limited thereto.

[0106] The second electrode (120) may be a negative electrode and may include a conductive material such as Al, Mg, Ca, Ag, or an alloy or combination thereof that has a relatively low work function value, but is not limited thereto.

[0108] The hole injection layer (140) may be located between the first electrode (110) and the hole transport layer (150). The hole injection layer (140) has the function of improving the interface characteristics between the first electrode (110) and the hole transport layer (150) and may be selected from a material having appropriate conductivity. The hole injection layer (140) may include compounds such as MTDATA, CuPc, TCTA, HATCN, TDAPB, PEDOT / PSS, N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine), and preferably may include N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine), but is not limited thereto.

[0110] The hole transport layer (150) is located adjacent to the light-emitting layer between the first electrode (110) and the light-emitting layer (160). The hole transport layer (150) may include compounds such as TPD, NPB, CBP, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl)-4-amine, and preferably may include NPB, but is not limited thereto.

[0112] According to the present invention, the light-emitting layer (160) may be formed by doping an organometallic compound represented by Formula 1 as a dopant (160) to improve the light-emitting efficiency of the host (160') and the device, and the dopant (160) may be used as a material that emits green or red light, and preferably as a green phosphorescent material.

[0113] The doping concentration of the dopant (160) of the present invention can be controlled within a range of 1 to 30 weight% based on the total weight of the host (160'), and is not limited thereto, for example, the doping concentration may be 2 to 20 weight%, for example, 3 to 15 weight%, for example, 5 to 10 weight%, for example, 3 to 8 weight%, for example, 2 to 7 weight%, for example, 5 to 7 weight%, for example, 5 to 6 weight%.

[0115] The light-emitting layer (160) of the present invention may include an organometallic compound represented by Chemical Formula 1 in the dopant (160") material, and may use a host (160') material used in the art field that can achieve the effects of the present invention. For example, in the present invention, a compound containing a carbazole group may be used as the host (160'), and preferably may include host materials such as CBP (carbazole biphenyl) and mCP (1,3-bis(carbazol-9-yl), but is not limited thereto.

[0117] Additionally, an electron transport layer (170) and an electron injection layer (180) may be sequentially stacked between the light-emitting layer (160) and the second electrode (120). The material of the electron transport layer (170) requires high electron mobility, and electrons can be stably supplied to the light-emitting layer through smooth electron transport.

[0119] For example, the material of the electron transport layer (170) is one used in the art, for example, Alq3 (tris(8-hydroxyquinolino)aluminum), Liq (8-hydroxyquinolinolatolithium), PBD (2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), TAZ (3-(4-biphenyl)4-phenyl-5-tert-butylphenyl-1,2,4-triazole), spiro-PBD, BAlq (bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminum), SAlq, TPBi (2,2',2-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole), oxadiazole, triazole, phenanthroline, benzoxazole, It may include compounds such as benzthiazole, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and preferably 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, but is not limited thereto.

[0121] The electron injection layer (180) serves to facilitate the injection of electrons, and the material of the electron injection layer is one used in the field of technology and may include, for example, compounds such as Alq3 (tris(8-hydroxyquinolino)aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq, but is not limited thereto. Alternatively, the electron injection layer (180) may be made of a metal compound, and the metal compound may include, for example, Liq, LiF, NaF, KF, RbF, CsF, FrF, BeF2, MgF2, CaF2, SrF2, BaF2, RaF2, but is not limited thereto.

[0122] The organic light-emitting device of the present invention may be a white organic light-emitting device having a tandem structure. In the case of a tandem organic light-emitting device according to one embodiment of the present invention, a single light-emitting stack (or light-emitting part) may be formed in a structure in which two or more are connected by a charge generation layer (CGL). The organic light-emitting device may include two or more plural light-emitting stacks (light-emitting parts) having a first electrode and a second electrode facing each other on a substrate, and a light-emitting layer stacked between the first and second electrodes that emits light of a specific wavelength range. The plural light-emitting stacks (light-emitting parts) may be applied to emit the same color or different colors. In addition, one light-emitting stack (light-emitting part) may also include one or more light-emitting layers, and the plural light-emitting layers may be light-emitting layers of the same or different colors.

[0123] At this time, one or more of the light-emitting layers included in the plurality of light-emitting parts may include an organometallic compound represented by Formula 1 according to the present invention as a dopant material. The plurality of light-emitting parts in the tandem structure may be connected to a charge generation layer (CGL) composed of an N-type charge generation layer and a P-type charge generation layer.

[0124] FIGS. 2 and FIGS. 3, exemplary embodiments of the present invention, are schematic cross-sectional views illustrating tandem organic light-emitting diodes having two light-emitting parts and three light-emitting parts, respectively.

[0125] As illustrated in FIG. 2, the organic light-emitting device (100) of the present invention comprises a first electrode (110) and a second electrode (120) facing each other, and an organic layer (230) located between the first electrode (110) and the second electrode (120). The organic layer (230) comprises a first light-emitting part (ST1) located between the first electrode (110) and the second electrode (120) and including a first light-emitting layer (261), a second light-emitting part (ST2) located between the first light-emitting part (ST1) and the second electrode (120) and including a second light-emitting layer (262), and a charge-generating layer (CGL) located between the first and second light-emitting parts (ST1 and ST2). The charge-generating layer (CGL) may include an N-type charge-generating layer (291) and a P-type charge-generating layer (292). One or more of the first light-emitting layer (261) and the second light-emitting layer (262) may include an organometallic compound represented by Formula 1 according to the present invention as a dopant. For example, as shown in FIG. 2, an organometallic compound represented by Formula 1 may be included as a dopant (262") together with the host (262') of the second light-emitting layer (262) of the second light-emitting part (ST2). Although not shown in FIG. 2, each of the first and second light-emitting parts (ST1 and ST2) may further include an additional light-emitting layer in addition to the first light-emitting layer (261) and the second light-emitting layer (262).

[0127] As illustrated in FIG. 3, the organic light-emitting element (100) of the present invention comprises a first electrode (110) and a second electrode (120) facing each other, and an organic layer (330) located between the first electrode (110) and the second electrode (120). The organic layer (330) includes a first light-emitting part (ST1) located between the first electrode (110) and the second electrode (120) and comprising a first light-emitting layer (261); a second light-emitting part (ST2) comprising a second light-emitting layer (262); a third light-emitting part (ST3) comprising a third light-emitting layer (263); a first charge-generating layer (CGL1) located between the first and second light-emitting parts (ST1 and ST2); and a second charge-generating layer (CGL2) located between the second and third light-emitting parts (ST2 and ST3). The first and second charge generating layers (CGL1 and CGL2) may each include an N-type charge generating layer (291, 293) and a P-type charge generating layer (292, 294). One or more of the first light-emitting layer (261), the second light-emitting layer (262), and the third light-emitting layer (263) may include an organometallic compound represented by Formula 1 according to the present invention as a dopant. For example, as illustrated in FIG. 3, an organometallic compound represented by Formula 1 may be included as a dopant (262") together with the host (262') of the second light-emitting layer (262) of the second light-emitting part (ST2). Although not illustrated in FIG. 3, each of the first, second, and third light-emitting parts (ST1, ST2, and ST3) may be formed with a plurality of light-emitting layers by including additional light-emitting layers in addition to the first light-emitting layer (261), the second light-emitting layer (262), and the third light-emitting layer (263).

[0129] Furthermore, an organic light-emitting device according to one embodiment of the present invention may include a tandem structure in which four or more light-emitting parts and three or more charge-generating layers are disposed between a first electrode and a second electrode.

[0131] The organic light-emitting element according to the present invention can be utilized in organic light-emitting display devices and lighting devices to which the organic light-emitting element is applied. In one embodiment, FIG. 4 is a cross-sectional view schematically illustrating an organic light-emitting display device to which an organic light-emitting element according to an exemplary embodiment of the present invention is applied.

[0132] As illustrated in FIG. 4, the organic light-emitting display device (3000) may include a substrate (3010), an organic light-emitting element (4000), and an encapsulation film (3900) covering the organic light-emitting element (4000). On the substrate (3010), a driving thin-film transistor (Td), which is a driving element, and an organic light-emitting element (4000) connected to the driving thin-film transistor (Td) are positioned.

[0133] Although not explicitly shown in FIG. 4, on the substrate (3010), gate wiring and data wiring that intersect each other to define pixel regions, power wiring that extends spaced apart parallel to either of the gate wiring and data wiring, switching thin-film transistors connected to the gate wiring and data wiring, and storage capacitors connected to one electrode of the power wiring and switching thin-film transistors are further formed.

[0134] The driving thin-film transistor (Td) is connected to the switching thin-film transistor and includes a semiconductor layer (3100), a gate electrode (3300), a source electrode (3520), and a drain electrode (3540).

[0135] The semiconductor layer (3100) is formed on the substrate (3010) and may be made of an oxide semiconductor material or polycrystalline silicon. If the semiconductor layer (3100) is made of an oxide semiconductor material, a light-blocking pattern (not shown) may be formed on the lower part of the semiconductor layer (3100), and the light-blocking pattern prevents light from being incident on the semiconductor layer (3100) to prevent the semiconductor layer (3100) from deteriorating due to light. Alternatively, the semiconductor layer (3100) may be made of polycrystalline silicon, in which case impurities may be doped on both edges of the semiconductor layer (3100).

[0136] A gate insulating film (3200) made of an insulating material is formed on the front surface of the substrate (3010) on the upper side of the semiconductor layer (3100). The gate insulating film (3200) may be made of an inorganic insulating material such as silicon oxide or silicon nitride.

[0137] A gate electrode (3300) made of a conductive material such as metal is formed on the upper part of the gate insulating film (3200) in correspondence with the center of the semiconductor layer (3100). The gate electrode (3300) is connected to a switching thin-film transistor.

[0138] An interlayer insulating film (3400) made of an insulating material is formed on the front surface of the substrate (3010) above the gate electrode (3300). The interlayer insulating film (3400) may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or of an organic insulating material such as benzocyclobutene or photoacryl.

[0139] The interlayer insulating film (3400) has first and second semiconductor layer contact holes (3420, 3440) that expose both sides of the semiconductor layer (3100). The first and second semiconductor layer contact holes (3420, 3440) are located on both sides of the gate electrode (3300) and spaced apart from the gate electrode (3300).

[0140] A source electrode (3520) and a drain electrode (3540) made of a conductive material such as metal are formed on the interlayer insulating film (3400). The source electrode (3520) and the drain electrode (3540) are spaced apart from the gate electrode (3300) and contact both sides of the semiconductor layer (3100) through the first and second semiconductor layer contact holes (3420, 3440), respectively. The source electrode (3520) is connected to a power wire (not shown).

[0141] A semiconductor layer (3100), a gate electrode (3300), a source electrode (3520), and a drain electrode (3540) form a driving thin-film transistor (Td), and the driving thin-film transistor (Td) has a coplanar structure in which the gate electrode (3300), the source electrode (3520), and the drain electrode (3540) are located on the upper part of the semiconductor layer (3100).

[0142] In contrast, the driving thin-film transistor (Td) may have an inverted staggered structure in which the gate electrode is located at the bottom of the semiconductor layer and the source and drain electrodes are located at the top of the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon. Meanwhile, the switching thin-film transistor (not shown) may have a structure substantially identical to that of the driving thin-film transistor (Td).

[0143] Meanwhile, the organic light-emitting display device (3000) may include a color filter (3600) that absorbs light generated from an organic light-emitting element (4000). For example, the color filter (3600) may absorb red (R), green (G), blue (B), and white (W) light. In this case, the red, green, and blue color filter patterns that absorb light may be formed separately for each pixel area, and each of these color filter patterns may be arranged to overlap with the organic layer (4300) in the organic light-emitting element (4000) that emits light of the wavelength band to be absorbed. By adopting the color filter (3600), the organic light-emitting display device (3000) can achieve full color.

[0144] For example, if the organic light-emitting display device (3000) is of the bottom-emission type, a color filter (3600) that absorbs light may be located on the upper part of the interlayer insulating film (3400) corresponding to the organic light-emitting element (4000). In an exemplary embodiment, if the organic light-emitting display device (3000) is of the top-emission type, the color filter may be located on the upper part of the organic light-emitting element (4000), that is, on the upper part of the second electrode (4200). For example, the color filter (3600) may be formed with a thickness of 2 to 5 μm.

[0145] Meanwhile, a protective layer (3700) having a drain contact hole (3720) that exposes the drain electrode (3540) of the driving thin-film transistor (Td) is formed to cover the driving thin-film transistor (Td).

[0146] On the protective layer (3700), a first electrode (4100) connected to the drain electrode (3540) of the driving thin-film transistor (Td) through the drain contact hole (3720) is formed separately for each pixel area.

[0147] The first electrode (4100) may be an anode and may be made of a conductive material having a relatively large work function value. For example, the first electrode (4100) may be made of a transparent conductive material such as ITO, IZO, or ZnO.

[0148] Meanwhile, if the organic light-emitting display device (3000) is of the top-emission type, a reflective electrode or reflective layer may be further formed below the first electrode (4100). For example, the reflective electrode or reflective layer may be made of any one of aluminum (Al), silver (Ag), nickel (Ni), or aluminum-palladium-copper (APC) alloy.

[0149] A bank layer (3800) covering the edge of the first electrode (4100) is formed on the protective layer (3700). The bank layer (3800) exposes the center of the first electrode (4100) corresponding to the pixel area.

[0150] An organic layer (4300) is formed on the first electrode (4100), and if necessary, the organic light-emitting element (4000) may have a tandem structure, and for the tandem structure, refer to FIGS. 2 to 4 showing exemplary embodiments of the present invention and the above description thereof.

[0151] A second electrode (4200) is formed on the upper surface of a substrate (3010) on which an organic layer (4300) is formed. The second electrode (4200) is located on the front surface of the display area and is made of a conductive material with a relatively small work function value and can be used as a cathode. For example, the second electrode (4200) can be made of any one of aluminum (Al), magnesium (Mg), or an aluminum-magnesium alloy (Al-Mg).

[0152] The first electrode (4100), the organic layer (4300), and the second electrode (4200) form an organic light-emitting element (4000).

[0153] On the second electrode (4200), an encapsulation film (3900) is formed to prevent external moisture from penetrating into the organic light-emitting diode (4000). Although not explicitly shown in FIG. 4, the encapsulation film (3900) may have a triple-layer structure in which a first inorganic layer, an organic layer, and an inorganic layer are sequentially stacked, but is not limited thereto.

[0155] The following describes manufacturing examples and embodiments of the present invention. However, the following embodiments are merely examples of the present invention and are not limited thereto.

[0157] Preparation Example - Preparation of Ligand

[0158] (1) Preparation of ligand A

[0159] Step 1) Preparation of Ligand A-2

[0160]

[0161] Compounds SM-1 (4.58 g, 20 mmol), SM-2 (3.67 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound A-2 (4.72 g, 82%).

[0162] Step 2) Preparation of Ligand A-1

[0163]

[0164] Compound A-2 (5.76 g, 20 mmol), SM-3 (4.28 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound A-1 (6.04 g, 80%).

[0165] Step 3) Preparation of Ligand A

[0166]

[0167] Compound A-1 (7.55 g, 20 mmol) was dissolved in 80 mL of acetic acid and 25 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere, and then tert-butyl nitrite (5 mL, 38 mmol) was added dropwise at 0°C while stirring. After stirring was completed at 0°C for 4 hours, the temperature was raised to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography with dichloromethane and hexane to obtain the above compound A (4.58 g, 64%).

[0169] (2) Preparation of ligand B

[0170] Step 1) Preparation of Ligand B-2

[0171]

[0172] Compound A-2 (5.76 g, 20 mmol), SM-4 (4.56 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound B-2 (6.50 g, 83%).

[0173] Step 2) Preparation of Ligand B-1

[0174]

[0175] Compound B-2 (7.83 g, 20 mmol) was dissolved in 80 mL of acetic acid and 25 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere, and then tert-butyl nitrite (5 mL, 38 mmol) was added dropwise at 0°C while stirring. After stirring was completed at 0°C for 4 hours, the temperature was raised to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography with dichloromethane and hexane to obtain the compound B-1 (5.05 g, 68%).

[0176] Step 3) Preparation of Ligand B

[0177]

[0178] Compound B-1 (7.43 g, 20 mmol) and Sodium tert-butoxide (4 mL, 40 mmol) were placed in 6,100 mL of DMSO in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred at 135°C for 48 hours. After the reaction was complete, the reaction vessel was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and dichloromethane by column chromatography to obtain the above compound B (6.13 g, 82%).

[0180] (3) Preparation of ligand C

[0181] Step 1) Preparation of Ligand C-2

[0182]

[0183] Compounds SM-5 (4.86 g, 20 mmol), SM-2 (3.67 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound C-2 (4.77 g, 79%).

[0184] Step 2) Preparation of Ligand C-1

[0185]

[0186] Compounds C-2 (6.04 g, 20 mmol), SM-3 (4.28 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound C-1 (6.58 g, 84%).

[0187] Step 3) Preparation of Ligand C

[0188]

[0189] Compound C-1 (7.83 g, 20 mmol) was dissolved in 80 mL of acetic acid and 25 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere, and then tert-butyl nitrite (5 mL, 38 mmol) was added dropwise at 0°C while stirring. After stirring was completed at 0°C for 4 hours, the temperature was raised to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography with dichloromethane and hexane to obtain the above compound C (4.83 g, 65%).

[0191] (4) Preparation of ligand D

[0192] Step 1) Preparation of Ligand D-2

[0193]

[0194] Compounds C-2 (6.04 g, 20 mmol), SM-4 (4.56 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound D-2 (6.81 g, 84%).

[0195] Step 2) Preparation of Ligand D-1

[0196]

[0197] Compound D-2 (8.11 g, 20 mmol) was dissolved in 80 mL of acetic acid and 25 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere, and then tert-butyl nitrite (5 mL, 38 mmol) was added dropwise at 0°C while stirring. After stirring was completed at 0°C for 4 hours, the temperature was raised to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography with dichloromethane and hexane to obtain the compound D-1 (6.32 g, 82%).

[0198] Step 3) Preparation of Ligand D

[0199]

[0200] Compound D-1 (7.71 g, 20 mmol) and Sodium tert-butoxide (4 mL, 40 mmol) were placed in 6,100 mL of DMSO-d in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred at 135°C for 48 hours. After the reaction was complete, the reaction vessel was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and dichloromethane by column chromatography to obtain the above compound D (5.43 g, 70%).

[0202] (5) Preparation of ligand E

[0203] Step 1) Preparation of Ligand E-2

[0204]

[0205] Compounds SM-6 (4.58 g, 20 mmol), SM-2 (3.67 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound E-2 (4.90 g, 85%).

[0206] Step 2) Preparation of Ligand E-1

[0207]

[0208] Compounds E-2 (5.76 g, 20 mmol), SM-3 (4.28 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound E-1 (6.42 g, 85%).

[0209] Step 3) Preparation of Ligand E

[0210]

[0211] Compound E-1 (7.55 g, 20 mmol) was dissolved in 80 mL of acetic acid and 25 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere, and then tert-butyl nitrite (5 mL, 38 mmol) was added dropwise at 0°C while stirring. After stirring was completed at 0°C for 4 hours, the temperature was raised to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography with dichloromethane and hexane to obtain the above compound E (4.86 g, 68%).

[0213] (6) Preparation of ligand F

[0214] Step 1) Preparation of Ligand F-2

[0215]

[0216] Compounds E-2 (5.76 g, 20 mmol), SM-4 (4.56 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound F-2 (6.34 g, 81%).

[0217] Step 2) Preparation of Ligand F-1

[0218]

[0219] Compound F-2 (7.83 g, 20 mmol) was dissolved in 80 mL of acetic acid and 25 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere, and then tert-butyl nitrite (5 mL, 38 mmol) was added dropwise at 0°C while stirring. After stirring was completed at 0°C for 4 hours, the temperature was raised to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography with dichloromethane and hexane to obtain the compound F-1 (6.17 g, 83%).

[0220] Step 3) Preparation of Ligand F

[0221]

[0222] Compound F-1 (7.43 g, 20 mmol) and Sodium tert-butoxide (4 mL, 40 mmol) were placed in 6,100 mL of DMSO in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred at 135°C for 48 hours. After the reaction was complete, the reaction vessel was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and dichloromethane by column chromatography to obtain the above compound F (5.01 g, 67%).

[0224] (7) Preparation of ligand G

[0225] Step 1) Preparation of ligand G-2

[0226]

[0227] Compounds SM-7 (4.86 g, 20 mmol), SM-2 (3.67 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound G-2 (4.83 g, 80%).

[0228] Step 2) Preparation of ligand G-1

[0229]

[0230] Compounds G-2 (6.04 g, 20 mmol), SM-3 (4.28 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound G-1 (6.58 g, 84%).

[0231] Step 3) Preparation of Ligand G

[0232]

[0233] Compound G-1 (7.83 g, 20 mmol) was dissolved in 80 mL of acetic acid and 25 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere, and then tert-butyl nitrite (5 mL, 38 mmol) was added dropwise at 0°C while stirring. After stirring was completed at 0°C for 4 hours, the temperature was raised to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography with dichloromethane and hexane to obtain the compound G (4.76 g, 64%).

[0235] (8) Preparation of ligand H

[0236] Step 1) Preparation of ligand H-2

[0237]

[0238] Compounds G-2 (6.04 g, 20 mmol), SM-4 (4.56 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound H-2 (6.65 g, 82%).

[0239] Step 2) Preparation of Ligand H-1

[0240]

[0241] Compound H-2 (8.11 g, 20 mmol) was dissolved in 80 mL of acetic acid and 25 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere, and then tert-butyl nitrite (5 mL, 38 mmol) was added dropwise at 0°C while stirring. After stirring was completed at 0°C for 4 hours, the temperature was raised to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography with dichloromethane and hexane to obtain the compound H-1 (6.25 g, 81%).

[0242] Step 3) Preparation of Ligand H

[0243]

[0244] Compound H-1 (7.71 g, 20 mmol) and Sodium tert-butoxide (4 mL, 40 mmol) were placed in 6100 mL of DMSO in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred at 135°C for 48 hours. After the reaction was complete, the reaction vessel was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and dichloromethane by column chromatography to obtain the compound H-1 (5.19 g, 67%).

[0246] (9) Preparation of Ligand I

[0247] Step 1) Preparation of Ligand I-3

[0248]

[0249] Compounds SM-8 (4.58 g, 20 mmol), SM-2 (3.67 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound I-3 (4.67 g, 81%).

[0250] Step 2) Preparation of Ligand I-2

[0251]

[0252] Compounds I-3 (5.76 g, 20 mmol), SM-4 (4.56 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound I-2 (6.42 g, 82%).

[0253] Step 3) Preparation of Ligand I-1

[0254]

[0255] Compound I-2 (7.83 g, 20 mmol) was dissolved in 80 mL of acetic acid and 25 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere, and then tert-butyl nitrite (5 mL, 38 mmol) was added dropwise at 0°C while stirring. After stirring was completed at 0°C for 4 hours, the temperature was raised to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography with dichloromethane and hexane to obtain the compound I-1 (5.80 g, 78%).

[0256] Step 4) Preparation of Ligand I

[0257]

[0258] Compound I-1 (7.43 g, 20 mmol) and Sodium tert-butoxide (4 mL, 40 mmol) were placed in 6100 mL of DMSO in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred at 135°C for 48 hours. After the reaction was complete, the reaction vessel was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and dichloromethane by column chromatography to obtain the above-mentioned compound I (4.86 g, 65%).

[0260] (10) Preparation of ligand J

[0261] Step 1) Preparation of ligand J-3

[0262]

[0263] Compounds SM-9 (4.86 g, 20 mmol), SM-2 (3.67 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound J-3 (4.71 g, 78%).

[0264] Step 2) Preparation of Ligand J-2

[0265]

[0266] Compounds J-3 (6.04 g, 20 mmol), SM-4 (4.56 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound J-2 (6.49 g, 80%).

[0267] Step 3) Preparation of Ligand J-1

[0268]

[0269] Compound J-2 (8.11 g, 20 mmol) was dissolved in 80 mL of acetic acid and 25 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere, and then tert-butyl nitrite (5 mL, 38 mmol) was added dropwise at 0°C while stirring. After stirring was completed at 0°C for 4 hours, the temperature was raised to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography with dichloromethane and hexane to obtain the compound J-1 (5.09 g, 66%).

[0270] Step 4) Preparation of Ligand J

[0271]

[0272] Compound J-1 (7.71 g, 20 mmol) and Sodium tert-butoxide (4 mL, 40 mmol) were placed in 6100 mL of DMSO in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred at 135°C for 48 hours. After the reaction was complete, the reaction vessel was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and dichloromethane by column chromatography to obtain the above compound J (6.36 g, 82%).

[0274] (11) Preparation of ligand K

[0275] Step 1) Preparation of ligand K-3

[0276]

[0277] Compounds SM-10 (4.58 g, 20 mmol), SM-2 (3.67 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound K-3 (4.44 g, 77%).

[0278] Step 2) Preparation of ligand K-2

[0279]

[0280] Compounds K-3 (5.76 g, 20 mmol), SM-4 (4.56 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound K-2 (6.26 g, 80%).

[0281] Step 3) Preparation of ligand K-1

[0282]

[0283] Compound K-2 (7.83 g, 20 mmol) was dissolved in 80 mL of acetic acid and 25 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere, and then tert-butyl nitrite (5 mL, 38 mmol) was added dropwise at 0°C while stirring. After stirring was completed at 0°C for 4 hours, the temperature was raised to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography with dichloromethane and hexane to obtain the compound K-1 (6.17 g, 83%).

[0284] Step 4) Preparation of Ligand K

[0285]

[0286] Compound K-1 (7.43 g, 20 mmol) and Sodium tert-butoxide (4 mL, 40 mmol) were placed in 6100 mL of DMSO in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred at 135°C for 48 hours. After the reaction was complete, the reaction vessel was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and dichloromethane by column chromatography to obtain the compound K (5.08 g, 68%).

[0288] (12) Preparation of ligand L

[0289] Step 1) Preparation of ligand L-3

[0290]

[0291] Compounds SM-11 (4.86 g, 20 mmol), SM-2 (3.67 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The water was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound L-3 (4.53 g, 75%).

[0292] Step 2) Preparation of ligand L-2

[0293]

[0294] Compounds L-3 (6.04 g, 20 mmol), SM-4 (4.56 g, 20 mmol), Pd(PPh3)4 (2.31 g, 2 mmol), P(t-Bu)3 (0.81 g, 4 mmol), and NaOtBu (7.68 g, 80 mmol) were dissolved in 200 mL of toluene in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred under reflux for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, the organic layer was extracted with dichloromethane, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and hexane by column chromatography to obtain the compound L-2 (6.33 g, 78%).

[0295] Step 3) Preparation of ligand L-1

[0296]

[0297] Compound L-2 (8.11 g, 20 mmol) was dissolved in 80 mL of acetic acid and 25 mL of THF in a 250 mL round-bottom flask under a nitrogen atmosphere, and then tert-butyl nitrite (5 mL, 38 mmol) was added dropwise at 0°C while stirring. After stirring was completed at 0°C for 4 hours, the temperature was raised to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated by column chromatography with dichloromethane and hexane to obtain the compound L-1 (5.01 g, 65%).

[0298] Step 4) Preparation of Ligand L

[0299]

[0300] Compound L-1 (7.71 g, 20 mmol) and Sodium tert-butoxide (4 mL, 40 mmol) were placed in 6100 mL of DMSO in a 250 mL round-bottom flask under a nitrogen atmosphere and heated and stirred at 135°C for 48 hours. After the reaction was complete, the reaction vessel was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the mixture was thoroughly washed with water. The moisture was removed with anhydrous magnesium sulfate, and the filtered solution was concentrated under reduced pressure and separated into ethyl acetate and dichloromethane by column chromatography to obtain the above compound L (6.51 g, 84%).

[0302] Preparation Example - Preparation of a precursor of an iridium compound ('iridium precursor')

[0303] ① Preparation of iridium precursor M'

[0304] Step 1) Preparation of Compound MM

[0305]

[0306] In a nitrogen atmosphere, a solution (Ethoxyethanol:distilled water = 90 mL:30 mL) containing compound M (3.38 g, 20 mmol) and IrCl3 (2.39 g, 8.0 mmol) was placed in a 250 mL round-bottom flask and stirred under reflux for 24 hours. After the reaction was complete, 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 4.24 g (94%) of solid compound MM.

[0307] Step 2) Preparation of iridium precursor M'

[0308]

[0309] Compound MM (4.51 g, 4 mmol) and Silver trifluoromethanesulfonate (AgOTf, 3.02 g, 12 mmol) were dissolved in dichloromethane in a 250 mL round-bottom flask and stirred at room temperature for 24 hours. After the reaction was complete, the solid precipitate was removed by filtering through Celite. The filtrate obtained through the filter was subjected to vacuum distillation to obtain 5.34 g (90%) of the resulting solid compound M'.

[0311] ② Preparation of Iridium Precursor B'

[0312] Step 1) Preparation of Compound BB

[0313]

[0314] In a nitrogen atmosphere, a solution (Ethoxyethanol:distilled water = 90 mL:30 mL) containing compound B (7.47 g, 20 mmol) and IrCl3 (2.39 g, 8.0 mmol) was placed in a 250 mL round-bottom flask and stirred under reflux for 24 hours. After the reaction was complete, 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 7.00 g (90%) of solid compound BB.

[0315] Step 2) Preparation of Iridium Precursor B'

[0316]

[0317] Compound BB (7.78 g, 4 mmol) and Silver trifluoromethanesulfonate (AgOTf, 3.02 g, 12 mmol) were dissolved in dichloromethane in a 250 mL round-bottom flask and stirred at room temperature for 24 hours. After the reaction was complete, the solid precipitate was removed by filtering with Celite. The filtrate obtained through the filter was subjected to vacuum distillation to obtain 3.87 g (84%) of the resulting solid compound B'.

[0319] ③ Preparation of Iridium Precursor D'

[0320] Step 1) Preparation of Compound DD

[0321]

[0322] In a nitrogen atmosphere, a solution (Ethoxyethanol:distilled water = 90 mL:30 mL) containing compound D (7.75 g, 20 mmol) and IrCl3 (2.39 g, 8.0 mmol) was placed in a 250 mL round-bottom flask and stirred under reflux for 24 hours. After the reaction was complete, 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 6.88 g (86%) of solid compound BB.

[0323] Step 2) Preparation of Iridium Precursor D'

[0324]

[0325] Compound DD (8.01 g, 4 mmol) and Silver trifluoromethanesulfonate (AgOTf, 3.02 g, 12 mmol) were dissolved in dichloromethane in a 250 mL round-bottom flask and stirred at room temperature for 24 hours. After the reaction was complete, the solid precipitate was removed by filtering through Celite. The filtrate obtained through the filter was subjected to vacuum distillation to obtain 4.01 g (85%) of the resulting solid compound D'.

[0327] ④ Preparation of iridium precursor F'

[0328] Step 1) Preparation of Compound FF

[0329]

[0330] Compound F (7.47 g, 20 mmol) and IrCl3 (2.39 g, 8.0 mmol) were added to a solution (Ethoxyethanol:distilled water = 90 mL:30 mL) mixed in a 250 mL round-bottom flask under a nitrogen atmosphere, and the mixture was stirred under reflux for 24 hours. After the reaction was complete, 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 6.54 g (84%) of solid compound FF.

[0331] Step 2) Preparation of iridium precursor F'

[0332]

[0333] Compound FF (7.78 g, 4 mmol) and Silver trifluoromethanesulfonate (AgOTf, 3.02 g, 12 mmol) were dissolved in dichloromethane in a 250 mL round-bottom flask and stirred at room temperature for 24 hours. After the reaction was complete, the solid precipitate was removed by filtering through Celite. The filtrate obtained through the filter was subjected to vacuum distillation to obtain 4.05 g (88%) of the resulting solid compound F'.

[0335] Preparation Example - Preparation of Iridium Compounds

[0336] 1. Preparation of Iridium Compound 66

[0337]

[0338] Under a nitrogen atmosphere, iridium precursor M' (1.11 g, 1.5 mmol) and ligand A (1.07 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 25:75 to obtain the following iridium compounds 66 (1.00 g, 75%) was obtained.

[0340] 2. Preparation of Iridium Compound 67

[0341]

[0342] Under a nitrogen atmosphere, iridium precursor M' (1.11 g, 1.5 mmol) and ligand B (1.12 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 25:75 to obtain the following iridium compounds 67 (0.96 g, 71%) was obtained.

[0344] 3. Preparation of Iridium Compound 96

[0345]

[0346] Under a nitrogen atmosphere, iridium precursor M' (1.11 g, 1.5 mmol) and ligand C (1.11 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 25:75 to obtain the following iridium compounds 96 (1.03 g, 76%) was obtained.

[0348] 4. Preparation of Iridium Compound 97

[0349]

[0350] Under a nitrogen atmosphere, iridium precursor M' (1.11 g, 1.5 mmol) and ligand D (1.16 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 25:75 to obtain the following iridium compounds 97 (1.11 g, 81%) was obtained.

[0352] 5. Preparation of Iridium Compound 216

[0353]

[0354] Under a nitrogen atmosphere, iridium precursor M' (1.11 g, 1.5 mmol) and ligand E (1.07 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 25:75 to obtain the following iridium compounds 216 (1.14 g, 86%) was obtained.

[0356] 6. Preparation of Iridium Compound 217

[0357]

[0358] Under a nitrogen atmosphere, iridium precursor M' (1.11 g, 1.5 mmol) and ligand F (1.12 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 25:75 to obtain the following iridium compounds 217 (1.09 g, 81%) was obtained.

[0360] 7. Preparation of Iridium Compound 246

[0361]

[0362] Under a nitrogen atmosphere, iridium precursor M' (1.11 g, 1.5 mmol) and ligand G (1.11 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 25:75 to obtain the following iridium compounds 246 (1.07 g, 79%) was obtained.

[0364] 8. Preparation of Iridium Compound 247

[0365]

[0366] Under a nitrogen atmosphere, iridium precursor M' (1.11 g, 1.5 mmol) and ligand H (1.16 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 25:75 to obtain the following iridium compounds 247 (1.10 g, 80%) was obtained.

[0368] 9. Preparation of Iridium Compound 309

[0369]

[0370] Under a nitrogen atmosphere, iridium precursor M' (1.11 g, 1.5 mmol) and ligand I (1.12 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 25:75 to obtain the following iridium compounds 309 (0.96 g, 71%) was obtained.

[0372] 10. Preparation of Iridium Compound 319

[0373]

[0374] Under a nitrogen atmosphere, iridium precursor M' (1.11 g, 1.5 mmol) and ligand J (1.16 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 25:75 to obtain the following iridium compounds 319 (1.04 g, 76%) was obtained.

[0376] 11. Preparation of Iridium Compound 349

[0377]

[0378] Under a nitrogen atmosphere, iridium precursor M' (1.11 g, 1.5 mmol) and ligand K (1.12 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 25:75 to obtain the following iridium compounds 349 (1.19 g, 88%) was obtained.

[0380] 12. Preparation of Iridium Compound 359

[0381]

[0382] Under a nitrogen atmosphere, iridium precursor M' (1.11 g, 1.5 mmol) and ligand L (1.16 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 25:75 to obtain the following iridium compounds 359 (1.15 g, 84%) was obtained.

[0384] 13. Preparation of Iridium Compound 469

[0385]

[0386] Under a nitrogen atmosphere, iridium precursor B' (1.72 g, 1.5 mmol) and ligand N (0.47 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuuming the filtrate was purified by column chromatography under ethylene acetate:hexane conditions of 50:50 to obtain the following iridium compounds. 469 (1.23 g, 75%) was obtained.

[0388] 14. Preparation of Iridium Compound 470

[0389]

[0390] Under a nitrogen atmosphere, iridium precursor D' (1.76 g, 1.5 mmol) and ligand N (0.47 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuuming the filtrate was purified by column chromatography under ethylene acetate:hexane conditions of 50:50 to obtain the following iridium compounds. 470 (1.21 g, 72%) was obtained.

[0392] 15. Preparation of Iridium Compound 479

[0393]

[0394] Under a nitrogen atmosphere, iridium precursor F' (1.72 g, 1.5 mmol) and ligand N (0.47 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under ethylene acetate:hexane conditions of 50:50 to obtain the following iridium compounds. 479 (1.28 g, 78%) was obtained.

[0396] 16. Preparation of Iridium Compound 509

[0397]

[0398] Under a nitrogen atmosphere, iridium precursor B' (1.72 g, 1.5 mmol) and ligand O (0.73 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuuming the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 40:60 to obtain the following iridium compounds 509 (1.38 g, 80%) was obtained.

[0400] 17. Preparation of Iridium Compound 510

[0401]

[0402] Under a nitrogen atmosphere, iridium precursor D' (1.76 g, 1.5 mmol) and ligand O (0.73 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuum extraction of the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 40:60 to obtain the following iridium compounds 510 (1.39 g, 79%) was obtained.

[0404] 18. Preparation of Iridium Compound 519

[0405]

[0406] Under a nitrogen atmosphere, iridium precursor F' (1.72 g, 1.5 mmol) and ligand O (0.73 g, 3 mmol) were placed in 50 mL of 2-ethoxyethanol and 50 mL of DMF in a 150 mL round-bottom flask and heated and stirred at 130 °C for 24 hours. After the reaction was complete, the temperature was lowered to room temperature, and the organic layer was extracted using dichloromethane and distilled water, while moisture was removed by adding anhydrous magnesium sulfate. The crude product obtained by vacuuming the filtrate was purified by column chromatography under conditions of Ethylacetate:Hexane = 40:60 to obtain the following iridium compounds 519 (1.40 g, 81%) was obtained.

[0408] Examples

[0409] < Example 1 >

[0410] After cleaning a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 Å, it was ultrasonically cleaned with an acetone solvent and dried. On the prepared ITO transparent electrode, HI-1 was thermally vacuum deposited to a thickness of 60 nm as a hole injection material, followed by thermally vacuum depositing NPB to a thickness of 80 nm as a hole transport material. On the transport material, compound 66 was used as the dopant and CBP as the host for the emissive layer, and it was thermally vacuum deposited with a doping concentration of 5 wt% and a thickness of 30 nm. On the emissive layer, ET-1:Liq (1:1) (30 nm) was thermally vacuum deposited as the material for the electron transport layer and electron injection layer, and then a 100 nm thick aluminum layer was deposited to form a cathode, thereby fabricating an organic light-emitting diode that emits green light.

[0411]

[0412]

[0413] The above HI-1 refers to N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine).

[0414] The above ET-1 refers to 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole.

[0416] < Examples 2–18 and Comparative Examples 1–7 >

[0417] Organic light-emitting diodes of Examples 2 to 18 and Comparative Examples 1 to 7 were each fabricated in the same manner as in Example 1, except that the compounds shown in Tables 1 and 2 below were used instead of compound 66 as the dopant in Example 1.

[0419] Performance Evaluation of Organic Light-Emitting Diodes >

[0420] For the organic light-emitting diodes prepared according to Examples 1 to 18 and Comparative Examples 1 to 7 above, 10 mA / cm 2Driving voltage and efficiency characteristics when driven by current, and 22.5 mA / cm² 2 By comparing the accelerated lifetime characteristics, the driving voltage (V), maximum luminous quantum efficiency (%), external quantum efficiency (EQE) (%), and LT95 (%) were measured. The maximum luminous quantum efficiency, EQE, and LT95 were converted into relative values ​​with respect to Comparative Example 1, and the results are shown in Tables 1 and 2 below. LT95 is a lifetime evaluation method that refers to the time required for an organic light-emitting diode to lose 5% of its initial brightness.

[0422] dopant Driving voltage (V) Maximum luminous efficiency (%, relative value) EQE(%, relative value) LT95(%, relative value) Comparative Example 1 Ref-1 4.25 100 100 100 Comparative Example 2 Ref-2 4.26 101 102 101 Comparative Example 3 Ref-3 4.25 95 96 105 Comparative Example 4 Ref-4 4.32 94 90 101 Comparative Example 5 Ref-5 4.30 91 88 104 Comparative Example 6 Ref-6 4.31 95 92 100 Comparative Example 7 Ref-7 4.34 92 90 106

[0424] The structures of Ref-1 to Ref-7, which are the dopant materials of Comparative Examples 1 to 7 in Table 1 above, are as follows.

[0425] , , , ,

[0426] , , .

[0428] dopant Driving voltage (V) Maximum luminous efficiency (%, relative value) EQE(%, relative value) LT95(%, relative value) Example 1 Compound 66 4.22 110 110 127 Example 2 Compound 67 4.21 111 111 129 Example 3 Compound 96 4.22 112 112 130 Example 4 Compound 97 4.21 113 113 132 Example 5 Compound 216 4.23 109 110 124 Example 6 Compound 217 4.24 108 109 125 Example 7 Compound 246 4.22 117 119 127 Example 8 Compound 247 4.23 117 117 129 Example 9 Compound 309 4.24 108 109 124 Example 10 Compound 319 4.23 112 115 127 Example 11 Compound 349 4.24 106 108 126 Example 12 Compound 359 4.22 112 114 129 Example 13 Compound 469 4.23 116 112 126 Example 14 Compound 470 4.21 115 111 128 Example 15 Compound 479 4.22 116 114 126 Example 16 Compound 509 4.22 117 113 127 Example 17 Compound 510 4.23 118 115 126 Example 18 Compound 519 4.24 115 114 124

[0430] As can be seen from the results of Tables 1 and 2 above, the organic light-emitting diodes in which the organometallic compounds used in Examples 1 to 18 of the present invention are applied as dopants in the light-emitting layer have a lower driving voltage and improved maximum luminous efficiency, external quantum efficiency (EQE), and lifetime (LT95) compared to Comparative Examples 1 to 7.

[0432] Although the embodiments of this specification have been described in more detail with reference to the attached drawings, this specification is not necessarily limited to these embodiments and may be modified in various ways within the scope of the technical spirit of this specification. Accordingly, the embodiments disclosed in this specification are intended to explain, not limit, the technical spirit of this specification, and the scope of the technical spirit of this specification is not limited by these embodiments. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive. The scope of protection of this specification shall be interpreted by the claims, and all technical spirits within an equivalent scope shall be interpreted as being included within the scope of rights of this specification. Explanation of the symbols

[0434] 100, 4000 : Organic light-emitting diode 110, 4100: First electrode 120, 4200 : Second electrode 130, 230, 330, 4300 : Organic layer 140 : Hole injection layer 150: Precision Transport Layer, 251: 1st Precision Transport Layer, 252: 2nd Precision Transport Layer, 253: 3rd Precision Transport Layer 160: Emitting layer, 261: First emitting layer, 262: Second emitting layer, 263: Third emitting layer 160', 262' : Host 160", 262" : Dopant 170: Electron transport layer, 271: First hole transport layer, 272: Second hole transport layer, 273: Third hole transport layer 180 : Electron injection layer 3000 : Organic light-emitting display 3010 : Substrate 3100 : Semiconductor layer 3200 : Gate insulating film 3300 : Gate electrode 3400 : Interlayer insulation film 3420, 3440: 1st and 2nd semiconductor layer contact holes 3520 : Source electrode 3540 : Drain electrode 3600 : Color filter 3700 : Protective layer 3720 : Drain contact hole 3800 : Bank layer 3900 : Encapsulation film

Claims

Claim 1 Organometallic compounds selected from the group consisting of the following compounds 216, 217, 246 and 247: ; . Claim 2 delete Claim 3 delete Claim 4 delete Claim 5 delete Claim 6 delete Claim 7 An organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises a light-emitting layer, the light-emitting layer comprises a dopant material, and the dopant material comprises an organometallic compound according to claim 1. Claim 8 In claim 7, the above-mentioned light-emitting layer is a green phosphorescent light-emitting layer, an organic light-emitting device. Claim 9 An organic light-emitting device according to claim 7, wherein the organic layer further comprises one or more selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer. Claim 10 An organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and a first light-emitting part and a second light-emitting part located between the first electrode and the second electrode, wherein the first light-emitting part and the second light-emitting part each comprise one or more light-emitting layers, at least one of the light-emitting layers is a green phosphorescent light-emitting layer, wherein the green phosphorescent light-emitting layer comprises a dopant material, and the dopant material comprises an organometallic compound according to claim 1. Claim 11 An organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and a first light-emitting part, a second light-emitting part, and a third light-emitting part located between the first electrode and the second electrode, wherein the first light-emitting part, the second light-emitting part, and the third light-emitting part each comprise one or more light-emitting layers, and at least one of the light-emitting layers is a green phosphorescent light-emitting layer, wherein the green phosphorescent light-emitting layer comprises a dopant material, and the dopant material comprises an organometallic compound according to claim 1. Claim 12 An organic light-emitting display device comprising: a substrate; a driving element located on the substrate; and an organic light-emitting element according to any one of claims 7 to 11 located on the substrate and connected to the driving element.

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