Organic metal compound, organic light-emitting diode and organic light emission device with the compound

Abstract

Organic metal compound with the following structure of formula 1: Ir(L A ) m (L B ) n [Formula 1] where L A which has the following structure of Formula 2; L B an auxiliary ligand with the following structure of formula 4 is; where m is an integer from 1 to 3 and n is an integer from 0 to 2, where m + n equals 3; where R1 is unsubstituted or substituted C1-C 20 -Alkyl, an unsubstituted alicyclic C4-C 30 -group or an unsubstituted or substituted aromatic C6-C 30 -group and R2 and R3 are independently hydrogen or deuterium, or R1 is defined above and R2 and R3 are unsubstituted aromatic C6-C 20 -form a ring; and A has the following structure of formula 3: where each of X1 to X4 is independent CR4; X5 to X7 is independent of CR5; X8 to X 11 independent CR6 is; Each R4 to R6 independently contains hydrogen, deuterium, or unsubstituted C1-C 20 -Alkyl is; wherein an imidazole ligand in formula 2 is bonded to a carbon atom forming CR4 from X1 to X4, and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom bonded by the imidazole ligand from X1 to X4, or an imidazole ligand in formula 2 is bonded to a carbon atom forming CR5 from X5 to X7, and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom is bound, which is bound by the imidazole ligand from X5 to X7;

Description

BACKGROUND Technical area

[0001] The present invention relates to an organic metal compound and in particular to an organic metal compound with excellent luminous efficiency and luminous lifetime, an organic light-emitting diode and an organic light emission device comprising the organic metal compound. Discussion of the state of the art

[0002] Organic light-emitting diodes (OLEDs), one of the most widely used flat display devices, have come to prominence as a rapidly replacing liquid crystal displays (LCDs). OLEDs can be formed as thin organic films of less than 2000 Å and can implement unidirectional or bidirectional images through electrode configurations. OLEDs can even be formed on flexible, transparent substrates such as plastics, making it easy to create flexible or foldable displays. Furthermore, OLEDs can be driven at lower voltages and offer higher color purity than LCDs.

[0003] Since fluorescent materials utilize only singlet exciton energy in their luminescence process, state-of-the-art fluorescent materials exhibit low luminescence efficiencies. Phosphorescent materials, in contrast, can exhibit high luminescence efficiencies because they utilize both triplet and singlet exciton energy in their luminescence process. However, metal complexes commonly used as phosphorescent materials have a luminescence lifetime that is too short for commercial applications. Therefore, there remains a need to develop a new compound that can improve both luminescence efficiency and lifetime.

[0004] EP 3 960 747 A1 describes an organic metal compound and an organic light-emitting diode containing this compound.

[0005] CN 109651444 A discloses a phosphorescent iridium complex comprising a ligand with an aromatic amine as a functional group. SUMMARY

[0006] Consequently, it was an object of the present invention to develop a compound, as well as an organic light-emitting diode and an organic light-emitting device comprising the compound, which substantially avoid one or more of the problems in the prior art.

[0007] In particular, one object of the present invention was to provide an organic metal compound with excellent luminous efficiency and luminous lifetime, an organic light-emitting diode and an organic light emission device comprising the compound.

[0008] Additional features and aspects are set out in the following description and are partly evident from the description or can be learned by carrying out the invention concepts provided here. Other features and aspects of the invention concept can be realized and achieved through the structure, which is specifically referred to in the written description or which can be derived from it, and the claims thereto, as well as the accompanying drawings.

[0009] The aforementioned problems underlying the present invention were solved by creating an organic metal compound as defined in independent claim 1, as well as an organic light-emitting diode and an organic light-emitting device comprising the compound. The organic metal compound has the following structure of formula 1: Ir(L A ) m (L B ) n [Formula 1] where L A Formula 2 has the following structure; L B an auxiliary ligand with the following structure of formula 4; m is an integer from 1 to 3 and n is an integer from 0 to 2, where m + n ≥ 3; where R1 is unsubstituted or substituted C1-C 20 -Alkyl, an unsubstituted alicyclic C4-C 30 -group or an unsubstituted or substituted aromatic C6-C 30 -group and R2 and R3 are independent of hydrogen or deuterium, or R1 is as defined above and R2 and R3 are unsubstituted aromatic C6-C 20 -form a ring; and A has the following structure of formula 3: where each from X1 to X4 is independent CR4; X5 to X7 is independent CR5; X8 to X 11 CR6 is independent; each R4 to R6 is independent of hydrogen, deuterium, or unsubstituted C1-C 20 -Alkyl is; wherein an imidazole ligand in formula 2 is bonded to a carbon atom forming CR4 from X1 to X4, and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom bonded by the imidazole ligand from X1 to X4, or an imidazole ligand in formula 2 is bonded to a carbon atom forming CR5 from X5 to X7, and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom bonded by the imidazole ligand from X5 to X7. It can be either a phenylpyridino-based ligand or an acetylacetonate-based ligand.

[0010] In a preferred embodiment, the ligand L A The organic metal compound has the following structure of formula 5: where each is from R1 to R3 and X1 to X 11as defined for formula 2 and formula 3. The imidazole ligand is also preferentially bonded to a carbon atom forming CR4 from X1 to X4, and the atom adjacent to the carbon atom bonded to the imidazole ligand from X1 to X4 is bonded to the iridium atom in formula 1.

[0011] In another preferred embodiment, the ligand L A any of the following structures of Formula 6A to Formula 6F: where each of a, b and c is a number of a substituent and a is an integer from 0 to 2, b is an integer from 0 to 3 and c is an integer from 0 to 4; each from R1 to R3 as defined for formula 2; each of R 11 to R 13 independent of hydrogen, deuterium or unsubstituted C1-C 20 -Alkyl is.

[0012] In particularly preferred embodiments, each of R 11 to R 13independent of hydrogen, deuterium or a C1-C6 alkyl, for example methyl or butyl.

[0013] In another embodiment, the ligand L A in the organic metal compound of the present invention the following structure of formula 7 wherein each R1 to R3 and X1 to X 11 as defined for formula 2 and formula 3. The imidazole ligand is also preferentially bonded to a carbon atom forming CR4 from X1 to X4, and the atom adjacent to the carbon atom bonded by the imidazole ligand from X1 to X4 is bonded to the iridium atom in formula 1.

[0014] In another preferred embodiment, the ligand L A The organic metal compound has the following structure of formula 8A or formula 8B: where each of d, e and f is a number of a substituent and d is an integer from 0 to 1, and each of e and f independently is an integer from 0 to 4; each from R1 to R3 as defined for formula 2; each of R 11 to R 13 independently of each other hydrogen, deuterium or unsubstituted C1-C 20 -Alkyl is.

[0015] Preferably, the auxiliary ligand L B The organic metal compound has the following structure of formula 9A or formula 9B: where each of R 21 , R 22 and R 31 to R 33 independent hydrogen, deuterium, unsubstituted or substituted C1-C 20 -Alkyl, unsubstituted or substituted C1-C 20 -Heteroalkyl, unsubstituted or substituted C2-C 20 -Alkenyl, unsubstituted or substituted C2-C 20 -Heteroalkenyl, unsubstituted or substituted C1-C 20-Alkoxy, a carboxyl group, nitrile, isonitrile, sulfanyl, phosphine, unsubstituted or substituted C1-C 20 -Alkylamino, unsubstituted or substituted C1-C 20 -Alkylsilyl, an unsubstituted or substituted alicyclic C4-C 30 -group, an unsubstituted or substituted heteroalicyclic C3-C 30 -group, an unsubstituted or substituted aromatic C6-C 30 -group or an unsubstituted or substituted heteroaromatic C3-C 30 -group is, or if each of j and k is 2 or more, each of adjacent two of R 31 to R 33 , adjacent two of R 21 and adjacent two of R 23 independently of an unsubstituted or substituted alicyclic C4-C 20 -ring, an unsubstituted or substituted heteroalicyclic C3-C 20 -ring, an unsubstituted or substituted aromatic C6-C 30-ring or an unsubstituted or substituted heteroaromatic C3-C 30 -ring forms. In a particularly preferred embodiment, each of R 21 , R 22 and R 31 to R 33 independent of hydrogen, deuterium or C1-C4 alkyl, for example methyl.

[0016] Preferably, m in formula 1 and n in formula 1 are both 1 or 2, provided that m + n = 3.

[0017] Alternatively, m in Formula 1 can be 3 and n in Formula 1 can be 0.

[0018] The organic metal compound preferably corresponds to one of the compounds in formula 10. The compounds covered by this formula are described in detail, but form part of the general disclosure.

[0019] In another preferred embodiment, the organic metal compound corresponds to one of the compounds in formula 11. The compounds covered by this formula are described in detail, but form part of the general disclosure.

[0020] The present invention further provides an organic light-emitting diode comprising a first electrode; a second electrode facing the first electrode; and an emission layer arranged between the first and second electrodes and comprising at least one emission material layer, wherein the at least one emission material layer comprises the organic metal compound as described above.

[0021] For example, the organic metal compound can be included as a doping material in at least one emission material layer.

[0022] Apart from the at least one emission material layer, the emission layer may comprise at least one hole transport layer and at least one electron transport layer arranged on opposite sides of the at least one emission material layer, wherein the at least one hole transport layer comprises or consists of N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4"-diamine (NPB; NPD) and the at least one electron transport layer comprises or consists of 2-[4-(9,10-Di-2-naphthalen-2-yl-2-anthracen-2-yl)phenyl] 1-phenyl-1H-benzimidazole (ZADN).

[0023] The at least one emission material layer can comprise a host and a dopant material, wherein the dopant material preferably comprises the organic metal compound as described above. Preferably, the dopant material is present in a concentration of 1 wt.% to 50 wt.%, more preferably in a concentration of 2.5 wt.% to 10.0 wt.%. The emission layer can have a single emission part or multiple emission parts to form a tandem structure. Furthermore, the emission layer of the organic light-emitting diode according to the present invention can comprise a first emission part arranged between the first and the second electrode, a second emission part arranged between the first emission part and the second electrode, and a first charge-generating layer arranged between the first and the second emission part.The first emission part can comprise a first emission material layer, and the second emission part can comprise a second emission material layer, and the first and / or second emission material layer can contain the organic metal compound.

[0024] Preferably, the second emission material layer comprises a lower emission material layer arranged between the first charge-generating layer and the second electrode, and an upper emission material layer arranged between the lower emission material layer and the second electrode. The lower emission material layer and the upper emission material layer may comprise the organic metal compound.

[0025] The emission layer can further comprise a third emission part, which is arranged between the second emission part and the second electrode. The third emission part can comprise a third emission material layer and a second charge generation layer, which is arranged between the second and third emission parts.

[0026] In yet another aspect, the present invention provides an organic light-emitting device, for example, an organic light-emitting display device or an organic light-emitting illumination device. The device comprises a substrate and the organic light-emitting diode, as described above. Preferably, the organic light-emitting diode is located in the device above the substrate. In this case, the organic light-emitting diode can be arranged on a substrate. In other words, the organic light-emitting diode can be arranged or located "above" or "above" the substrate, assuming that the emitted light propagates towards the top of the device.

[0027] It should be self-evident that both the preceding general description and the following detailed description are exemplary and explanatory and are intended to provide a further explanation of the invention concepts as claimed. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] The accompanying drawings, which are included to provide a further understanding of the invention, are incorporated into this application and form a part of it, represent embodiments of the invention and, together with the description, serve to explain the principles of the invention. Fig. Figure 1 is a schematic circuit diagram representing an organic light emission indicator device according to the present invention. Fig. Figure 2 is a cross-sectional view showing an organic light emission indicator device as an example of an organic light emission device according to an exemplary aspect of the present invention. Fig. Figure 3 is a cross-sectional view showing an organic light-emitting diode with a single emission part according to an exemplary aspect of the present invention. Fig. Figure 4 is a cross-sectional view showing an organic light emission indicator device according to another exemplary aspect of the present invention. Fig. Figure 5 is a cross-sectional view showing an organic light-emitting diode with a double-stack structure according to yet another exemplary aspect of the present invention. Fig. Figure 6 is a cross-sectional view showing an organic light-emitting diode with a triple-stack structure according to yet another exemplary aspect of the present invention. DETAILED DESCRIPTION

[0029] Now, specific aspects of the invention will be discussed, examples of which are shown in the accompanying drawings. [Organic metal compound]

[0030] The luminescent material in an organic light-emitting diode (OLED) should exhibit excellent luminous efficiency and lifetime. An organic metal compound according to the present invention has a rigid chemical conformation, such that it exhibits excellent luminous efficiency and lifetime. The organic metal compound of the present invention can have the following structure of formula 1: Ir(L A ) m (L B ) n [Formula 1] where L AFormula 2 has the following structure; L B an auxiliary ligand with the following structure of formula 4; m is an integer from 1 to 3 and n is an integer from 0 to 2, where m + n ≥ 3; where R1 is unsubstituted or substituted C1-C 20 -Alkyl, an unsubstituted alicyclic C4-C 30 -group or an unsubstituted or substituted aromatic C6-C 30 -group and R2 and R3 are independent hydrogen, deuterium, or R1 is as defined above and R2 and R3 are unsubstituted aromatic C6-C 20 -form a ring; and A has the following structure of formula 3: where each from X1 to X4 is independent CR4; X5 to X7 is independent CR5; X8 to X 11 CR6 is independent; each R4 to R6 is independent of hydrogen, deuterium, or unsubstituted C1-C 20-alkyl; wherein an imidazole ligand in formula 2 is bonded to a carbon atom forming CR4 from X1 to X4, and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom bonded by the imidazole ligand from X1 to X4, or an imidazole ligand in formula 2 is bonded to a carbon atom forming CR5 from X5 to X7, and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom bonded by the imidazole ligand from X5 to X7;

[0031] As used here, the term 'unsubstituted' means that hydrogen is bound, and in this case hydrogen includes hydrogen, deuterium, and tritium.

[0032] As used here, a substituent in the term "substituted" includes unsubstituted or deuterium- or halogen-substituted C1-C 20 -Alkyl, unsubstituted or deuterium or halogen-substituted C1-C 20-Alkoxy, halogen, cyano, -CF3, a hydroxyl group, a carboxyl group, a carbonyl group, an amino group, a C1-C 10 -Alkylamino group, a C6-C 30 -Arylamino group, a C3-C 30 -Heteroarylamino group, a C6-C 30 -Aryl group, a C3-C 30 -Heteroaryl group, a nitro group, a hydracyl group, a sulfonate group, a C1-C 20 -Alkylsilyl group, a C6-C 30 -A-rylsilyl group and a C3-C 30 -Heteroarylsilyl group, but is not limited to that.

[0033] As used here, the term "hetero" in such terms as "heteroalkyl", "heteroalkenyl", "a heteroalicyclic group", "a heteroaromatic group", "a heterocycloalkylene group", "a heteroarylene group", "a heteroarylalkylene group", "a heteroaryloxylene group", "a heterocycloalkyl group", "a heteroaryl group", "a heteroarylalkyl group", "a heteroaryloxy group", "a heteroaryllamino group" means that at least one carbon atom, for example 1-5 carbon atoms, forming an aliphatic chain, an alicyclic group or an alicyclic ring, or an aromatic group or an aromatic ring, is substituted with at least one heteroatom selected from the group consisting of N, O, S, P and combinations thereof.

[0034] In one exemplary aspect, if R1 in formula 2 is an aromatic C6-C 30 -group is, R1 a C6-C 30 -Aryl group, a C7-C 30-Arylalkyl group, a C6-C 30 -Aryloxy group and a C6-C 30 It can be an -arylamine group, but this is not limited to that. For example, if R1 is a C6-C 30 -aryl group, R1 is an unfused or fused aryl group, such as phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pentalenyl, indenyl, indeno-indenyl, heptalenyl, biphenylenyl, indacenyl, phenalenyl, phenanthrenyl, benzo-phenanthrenyl, dibenzo-phenanthrenyl, azulenyl, pyrenyl, fluoranthenyl, triphenylenyl, chrysenyl, tetraphenylenyl, tetracenyl, pleiadenyl, picenyl, pentaphenylenyl, pentacenyl, fluorenyl, indeno-fluorenyl and spiro-fluorenyl, but is not limited to.

[0035] As an example, the aromatic group of R1 in formula 2 can consist of one to three aromatic rings. If the number of aromatic rings in R1 exceeds four, the conjugated structure within the entire molecule becomes too long, consequently the organic metal compound may exhibit an excessively narrow energy band gap. For example, each of the aryl groups of R 1 It may include, but is not limited to, phenyl, biphenyl, naphthyl and / or anthracenyl.

[0036] Furthermore, an unsubstituted alicyclic C4-C 30 -Group of R1 in formula 2 independently an unsubstituted cyclic C4-C 30 -Alkyl group and an unsubstituted cyclic C4-C 30 -Alkenyl group, but is not limited to that.

[0037] In one exemplary aspect, each of the alkyl or aromatic groups of R1 can be independently unsubstituted or with at least one of halogen, C1-C 10-Alkyl, an alicyclic C4-C 20 -group, a heteroalicyclic C3-C 20 -group, an aromatic C6-C 20 -group and a heteroaromatic C3-C 20 -group be substituted.

[0038] Alternatively, each of R2 and R3 can independently form an unsubstituted aromatic C6-C 20 -ring. The aromatic rings formed by each of R2 and R3 are not limited to specific rings. The aromatic ring formed by these groups can, for example, include a benzene ring, but is not limited to one that is unsubstituted.

[0039] The organic metal compound with the structure of formula 1 features a heteroaromatic ligand consisting of at least five rings. Because the organic metal compound exhibits a rigid chemical conformation, preventing conformational rotation during the luminescence process, it can maintain a good luminescence lifetime. The organic metal compound also exhibits specific regions of photoluminescence emission, thus improving its color purity.

[0040] In one exemplary aspect, each of m and n in Formula 1 can be 1 or 2, provided that m + n equals 3. If the organic metal compound is a heteroleptic metal complex with two different bidentate ligands coordinated to the central metal atom, the photoluminescence color purity and emission colors of the organic metal compound can be easily controlled by combining two different bidentate ligands. Furthermore, it is possible to control the color purity and emission peaks of the organic metal compound by introducing different substituents to each of the ligands. Alternatively, in Formula 1, m can be 3 and n can be 0. For example, the organic metal compound with the structure of Formula 1 emits green light and can improve the luminous efficiency of an organic light-emitting diode.

[0041] Each from X1 to X4 is independent CR4, each from X5 to X7 is independent CR5, and each from X8 to X 11 is independent of CR6. That means each from X1 to X 11 can be either an unsubstituted or substituted carbon atom.

[0042] In one exemplary aspect, the fused heteroaromatic ligand with the structure of formula 3 can be bound to the central iridium atom and the imidazole ligand via the ring with X1 to X4 as the nuclear atom. A major ligand L A With a bonding structure, the following structure of formula 5 can be observed: where each is from R1 to R3 and X1 to X 11 the same as defined in Formula 2 and Formula 3.

[0043] For example, the main ligan L A the structure of formula 5 includes any of the following structures of formulas 6A to 6F: where each of R1 to R3 is defined in the same way as in formula 2; each of R 11to R 13 independent of hydrogen, deuterium or unsubstituted C1-C 20 -Alkyl is.

[0044] In another exemplary aspect, the fused heteroaromatic ligand with the structure of formula 3 can be bound to the central iridium atom and the imidazole ligand via the ring with X5 to X7 as the nuclear atom. A major ligand L A With such a bonding structure, the following structure of formula 7 can be observed: where each from R1 to R3 and X1 to X 11 the same as defined in Formula 2 and Formula 3.

[0045] For example, the main ligan L A with the structure of formula 7 exhibit any of the following structures of formula 8A or formula 8B: where each of R1 to R3 is defined in the same way as in formula 2; each of R 11 to R 13 independent of hydrogen, deuterium or unsubstituted C1-C 20 -Alkyl is.

[0046] In yet another exemplary aspect, L B The auxiliary ligand can be a phenylpyridino-based ligand or an acetylacetonate-based ligand. For example, L B The following structure of Formula 9A or Formula 9B is not limited to this: where each of R 21 , R 22 and R 31 to R 33 independent hydrogen, deuterium, unsubstituted or substituted C1-C 20 -Alkyl, unsubstituted or substituted C1-C 20 -Heteroalkyl, unsubstituted or substituted C2-C 20 -Alkenyl, unsubstituted or substituted C2-C 20 -Heteroalkenyl, unsubstituted or substituted C1-C 20 -Alkoxy, a carboxyl group, nitrile, isonitrile, sulfanyl, phosphine, unsubstituted or substituted C1-C 20 -Alkylamino, unsubstituted or substituted C1-C 20-Alkylsilyl, an unsubstituted or substituted alicyclic C4-C 30 -group, an unsubstituted or substituted heteroalicyclic C3-C 30 -group, an unsubstituted or substituted aromatic C6-C 30 -group or an unsubstituted or substituted heteroaromatic C3-C 30 -group is, or each of adjacent two of R 31 to R 33 , adjacent two of R 21 and adjacent two of R 23 independently of an unsubstituted or substituted alicyclic C4-C 20 -ring, an unsubstituted or substituted heteroalicyclic C3-C 20 -ring, an unsubstituted or substituted aromatic C6-C 30 -ring or an unsubstituted or substituted heteroaromatic C3-C 30 A ring is formed if each of j and k is 2 or more.

[0047] The substituents of R 21 to R 22 and R 31 to R33 or the ring that is through R 21 to R 22 and R 31 to R 33 The group formed can be identical to the substituents or the ring as described in formulas 2 and 3. Furthermore, any of the alkyl, heteroalkyl, alkenyl, heteroalkenyl, alkoxy, alkylamino, alkylsilyl, alicyclic, heteroalicyclic, aromatic, and heteroaromatic groups of R can be formed. 21 to R 33 in formulas 9A to 9B independently unsubstituted or with at least one of halogen, C1-C 10 -Alkyl, an alicyclic C4-C 20 -group, a heteroalicyclic C3-C 20 -group, an aromatic C6-C 20 -group and a heteroaromatic C3-C 20 -group can be substituted. Furthermore, any of the alicyclic C4-C can be substituted. 20 -ring, of the heteroalicyclic C3-C 20 -Rings, of the aromatic C6-C 30-ring and the heteroaromatic C3-C 30 -Rings, which are divided by each of adjacent two of R 21 , adjacent two of R 22 and adjacent two of R 31 to R 33 are formed, independently unsubstituted or with at least one C1-C 10 -alkyl group substituted.

[0048] In one exemplary aspect, the organic metal compound can have the structure of formulas 1 to 4, where, for example, L A the structure of formula 5 may be selected from the following organic metal compounds of formula 10, but is not limited to:

[0049] In another exemplary aspect, the organic metal compound can have the structure of formulas 1 to 4, where, for example, L A the structure of formula 7 may be selected from the following organic metal compounds of formula 11, but is not limited to:

[0050] The organic metal compound with any of the structures from formula 5 to formula 11 comprises a heteroaromatic ligand consisting of at least 5 rings, thus exhibiting a rigid chemical conformation. This organic metal compound can improve its color purity and luminous lifetime because it maintains its stable chemical conformation during the emission process. Furthermore, since the organic metal compound can be a metal complex with bidentate ligands, it is possible to easily control the emission color purity and emission colors. Consequently, an organic light-emitting diode with excellent luminous efficiency is obtained by applying the organic metal compound with any of the structures from formulas 1 to 11 in an emission layer. [Organic light emission device and organic light-emitting diode]

[0051] It is possible to realize an OLED with reduced drive voltage, excellent luminous efficacy, and improved lifetime by applying the organic compound with the structure of formulas 1 to 11 in an emission layer, for example, an emission material layer of the OLED. The OLED of the present invention can be applied to an organic light-emitting device, such as an organic light-emitting display device or an organic light-emitting illumination device. An organic light-emitting display device incorporating the OLED is described.

[0052] Fig. Figure 1 is a schematic circuit diagram representing an organic light emission indicator device according to an exemplary aspect of the present invention. As shown in Fig. Figure 1 shows a gate line GL, a data line DL, and a power line PL, all intersecting to define a pixel area P in the organic light emission display device. A switching thin-film transistor Ts, a drive thin-film transistor Td, a storage capacitor Cst, and an organic light-emitting diode D are formed within the pixel area P. The pixel area P can include a red (R) pixel area, a green (G) pixel area, and a blue (B) pixel area.

[0053] The switching thin-film transistor Ts is connected to the gate line GL and the data line DL, and the driver thin-film transistor Td and the storage capacitor Cst are connected between the switching thin-film transistor Ts and the power line PL. The organic light-emitting diode D is connected to the driver thin-film transistor Td. When the switching thin-film transistor Ts is switched on by a gate signal applied to the gate line GL, a data signal applied to the data line DL is applied to a gate electrode of the driver thin-film transistor Td and to an electrode of the storage capacitor Cst via the switching thin-film transistor Ts.

[0054] The driver thin-film transistor Td is switched on by the data signal applied to its gate electrode, so that a current proportional to the data signal is supplied from the power line PL to the organic light-emitting diode D through the driver thin-film transistor Td. The organic light-emitting diode D then emits light with a luminance proportional to the current flowing through the driver thin-film transistor Td. In this case, the storage capacitor Cst is charged with a voltage proportional to the data signal, so that the voltage at the gate electrode of the driver thin-film transistor Td is kept constant during a frame. Therefore, the organic light emission display device can display a desired image.

[0055] Fig. Figure 2 is a schematic cross-sectional view illustrating an organic light emission indicator device according to an exemplary aspect of the present invention. As shown in Fig. As shown in Figure 2, the organic light emission indicator device 100 comprises a substrate 102, a thin-film transistor Tr over the substrate 102, and an organic light-emitting diode D connected to the thin-film transistor Tr. For example, the substrate 102 defines a red pixel area, a green pixel area, and a blue pixel area, and the organic light-emitting diode D is positioned in each pixel area. In other words, the organic light-emitting diode D, each emitting red, green, or blue light, is positioned accordingly in the red pixel area, the green pixel area, and the blue pixel area.

[0056] Substrate 102 can comprise, but is not limited to, glass, a thin flexible material, and / or polymer plastic. The flexible material can be selected, for example, from the group consisting of polyimide (PI), polyethersulfone (PES), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), polycarbonate (PC), and combinations thereof, but is not limited to these. Substrate 102, on top of which the thin-film transistor Tr and the organic light-emitting diode D are arranged, forms a matrix substrate.

[0057] A buffer layer 106 can be arranged over the substrate 102, and the thin-film transistor Tr is arranged over the buffer layer 106. However, the buffer layer 106 can also be omitted.

[0058] A semiconductor layer 110 is arranged above the buffer layer 106. In one exemplary aspect, the semiconductor layer 110 can comprise, but is not limited to, oxide semiconductor materials. In this case, a light-shielding pattern can be arranged beneath the semiconductor layer 110, and the light-shielding pattern can prevent light from entering the semiconductor layer 110, thereby preventing light degradation of the semiconductor layer 110. Alternatively, the semiconductor layer 110 can comprise polycrystalline silicon. In this case, opposite edges of the semiconductor layer 110 can be doped with impurities.

[0059] A gate insulating layer 120 with an insulating material is arranged on the semiconductor layer 110. The gate insulating layer 120 can be an inorganic insulating material such as silicon dioxide (SiO₂). x ) or silicon nitride (SiN x ) include, but is not limited to.

[0060] A gate electrode 130, made of an electrically conductive material such as a metal, is positioned above the gate insulating layer 120 such that it corresponds to the center of the semiconductor layer 110. Although the gate insulating layer 120 extends over an entire area of ​​the substrate 102 in Fig. 2 is arranged, the gate insulation layer 120 can be structured in the same way as the gate electrode 130.

[0061] An intermediate insulating layer 140 with an insulating material is arranged on the gate electrode 130, covering an entire surface of the substrate 102. The intermediate insulating layer 140 can be an inorganic insulating material such as silicon dioxide (SiO₂). x ) or silicon nitride (SiN x ) or an organic insulating material such as benzocyclobutene or photoacrylic.

[0062] The intermediate insulating layer 140 has a first and a second semiconductor layer contact hole 142 and 144, which expose both sides of the semiconductor layer 110. The first and the second semiconductor layer contact holes 142 and 144 are arranged over opposite sides of the gate electrode 130 at a distance from the gate electrode 130. The first and the second semiconductor layer contact holes 142 and 144 are located within the gate insulating layer 120. Fig. 2 formed. Alternatively, the first and second semiconductor layer contact holes 142 and 144 are formed only within the intermediate layer insulation layer 140 if the gate insulation layer 120 is structured identically to the gate electrode 130.

[0063] A source electrode 152 and a drain electrode 154, made of an electrically conductive material such as a metal, are arranged on the intermediate insulating layer 140. The source electrode 152 and the drain electrode 154 are spaced apart from each other with respect to the gate electrode 130 and contact both sides of the semiconductor layer 110 through the first and second semiconductor layer contact holes 142 and 144, respectively.

[0064] The semiconductor layer 110, the gate electrode 130, the source electrode 152, and the drain electrode 154 form the thin-film transistor Tr, which acts as a control element. The thin-film transistor Tr in Fig. 2 has a coplanar structure in which the gate electrode 130, the source electrode 152, and the drain electrode 154 are arranged above the semiconductor layer 110. Alternatively, the thin-film transistor Tr can have an inverted staggered structure in which a gate electrode is arranged below a semiconductor layer and a source and a drain electrode are arranged above the semiconductor layer. In this case, the semiconductor layer can comprise amorphous silicon.

[0065] Although in Fig. Not shown in Figure 2, a gate line and a data line, which cross to define a pixel area, and a switching element connected to the gate line and the data line, can further be formed within the pixel area. The switching element is connected to the thin-film transistor Tr, which is a driver element. Additionally, a power line is spaced parallel to or spaced apart from the gate line or the data line, and the thin-film transistor Tr can further include a storage capacitor configured to maintain a constant gate electrode voltage for a frame.

[0066] A passivation layer 160 is arranged on the source and drain electrodes 152 and 154, covering the entire substrate 102 of the thin-film transistor Tr. The passivation layer 160 has a flat top surface and a drain contact hole 162 that exposes the drain electrode 154 of the thin-film transistor Tr. Although the drain contact hole 162 is located on top of the second semiconductor layer contact hole 144, it may be spaced apart from it.

[0067] The organic light-emitting diode (OLED) D comprises a first electrode 210, which is arranged on the passivation layer 160 and is connected to the drain electrode 154 of the thin-film transistor Tr. The organic light-emitting diode D further comprises an emission layer 230 and a second electrode 220, each of which is arranged sequentially on the first electrode 210.

[0068] The first electrode 210 is located in each pixel area. The first electrode 210 can be an anode and comprise an electrically conductive material with a relatively high work function value. For example, the first electrode 210 can comprise, but is not limited to, a transparent conductive oxide (TCO) such as indium tin oxide (ITO), indium zinc oxide (IZO), indium tin-zinc oxide (ITZO), SnO, ZnO, indium cerium oxide (ICO), or aluminum-doped zinc oxide (AZO).

[0069] In one exemplary aspect, if the organic light emission display device 100 is a bottom-emission type, the first electrode 210 can have a single-layer structure of TCO. Alternatively, if the organic light emission display device 100 is a top-emission type, a reflective electrode or a reflective layer can be arranged beneath the first electrode 210. The reflective electrode or reflective layer can, for example, comprise silver (Ag) or an aluminum-palladium-copper (APC) alloy, but is not limited to these materials. In the top-emission type OLED D, the first electrode 210 can have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0070] Furthermore, a bank layer 164 is arranged on the passivation layer 160 to cover edges of the first electrode 210. The bank layer 164 exposes a center of the first electrode 210 that corresponds to each pixel area. However, the bank layer 164 can also be omitted.

[0071] An emission layer 230 is arranged on the first electrode 210. As an example, the emission layer 230 can have a single-layer structure of an emission material layer (EML). Alternatively, the emission layer 230 can have a multi-layer structure of a hole injection layer (HIL), a hole transport layer (HTL), an electron barrier layer (EBL), an EML, a hole barrier layer (HBL), an electron transport layer (ETL), and / or an electron injection layer (EIL) (see Fig. 3, Fig. 5 and Fig. 6) In one aspect, the emission layer 230 can have a single emission component. Alternatively, the emission layer 230 can have multiple emission components to form a tandem structure.

[0072] The emission layer 230 can comprise the organic metal compound with the structure of formulas 1 to 11. The emission layer 230 with the organic metal compound enables the OLED D and the organic light emission device 100 to significantly improve their luminous efficiency and luminous lifetime.

[0073] The second electrode 220 is arranged above the substrate 102, above which the emission layer 230 is arranged. The second electrode 220 can be arranged over an entire display area and can comprise an electrically conductive material with a relatively low work function value compared to the first electrode 210, and can be a cathode. The second electrode 220 can, for example, comprise aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), an alloy thereof, or combinations thereof, such as an aluminum-magnesium alloy (Al-Mg), but is not limited to these. If the organic light emission display device 100 is a top-emission type, the second electrode 220 is so thin that it has a translucent (semi-transparent) property.

[0074] Furthermore, an encapsulation film 170 can be arranged over the second electrode 220 to prevent external moisture from penetrating the organic light-emitting diode D. The encapsulation film 170 can have, but is not limited to, a laminated structure of a first inorganic insulating film 172, an organic insulating film 174, and a second inorganic insulating film 176. The encapsulation film 170 can also be omitted.

[0075] A polarizing plate can be attached to the encapsulation film to reduce the reflection of external light. The polarizing plate can, for example, be a circular polarizing plate. If the organic light emission indicator 100 is a bottom-emission type, the polarizer can be located below the substrate 100. If the organic light emission indicator 100 is a top-emission type, the polarizer can alternatively be located above the encapsulation film 170. Additionally, a cover window can be attached to the encapsulation film 170 or to the polarizer. In this case, the substrate 110 and the cover window can be flexible, thus the organic light emission indicator 100 can be a flexible indicator.

[0076] Next, we will describe the OLED D with the organic metal compound in more detail. Fig. Figure 3 is a schematic cross-sectional view showing an organic light-emitting diode with a single emission component according to an exemplary embodiment of the present invention. As in Fig. Figure 3 shows that the organic light-emitting diode (OLED) D1 according to the present invention comprises a first and a second electrode 210 and 220 facing each other, and an emission layer 230 arranged between the first and the second electrode 210 and 220. The organic light emission display device 100 comprises a red pixel area, a green pixel area, and a blue pixel area, and the OLED D1 can be arranged in the green pixel area.

[0077] In an exemplary embodiment, the emission layer 230 comprises an emission material layer (EML) 340 arranged between the first and second electrodes 210 and 220. The emission layer 230 may also comprise a high-temperature layer (HTL) 320 arranged between the first electrode 210 and the EML 340, and / or an emission material layer (ETL) 360 arranged between the second electrode 220 and the EML 340. Furthermore, the emission layer 230 may also comprise a high-temperature layer (HIL) 310 arranged between the first electrode 210 and the HTL 320, and / or an emission material layer (EIL) 370 arranged between the second electrode 220 and the ETL 360. Alternatively, the emission layer 320 can further comprise a first exciton barrier layer, i.e. an EBL 330, arranged between the HTL 320 and the EML 340, and / or a second exciton barrier layer, i.e. an HBL 350, arranged between the EML 340 and the ETL 360.

[0078] The first electrode 210 can be an anode providing a hole in the EML 340. The first electrode 210 can comprise an electrically conductive material with a relatively high work function value, for example, a transparent conductive oxide (TCO). In an exemplary embodiment, the first electrode 210 can comprise, but is not limited to, ITO, IZO, ITZO, SnO, ZnO, ICO, or AZO.

[0079] The second electrode 220 can be a cathode that supplies an electron to the EML 340. The second electrode 220 can comprise an electrically conductive material with relatively low work function values, i.e., a highly reflective material such as Al, Mg, Ca, Ag, an alloy thereof, or combinations thereof, such as Al-Mg.

[0080] The HIL 310 is positioned between the first electrode 210 and the HTL 320 and improves the interface properties between the inorganic first electrode 210 and the organic HTL 320.In an exemplary embodiment, HIL 310 can be 4,4'4"-Tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-Tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4"-Tris(N-(naphthalen-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-Tris(N-(naphthalen-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), Tris(4-carbazoyl-9-yl-phenyl)amine (TCTA), N,N'-Diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4"-diamine (NPB; NPD), 1,4,5,8,9,11-Hexaazatriphenylenhexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile; HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), Poly(3,4-ethylenedioxythiophene)polystyrene sulfonate (PEDOT / PSS), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), N-(Biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, N,N'-Diphenyl-N,N'-di[4-(N,N'-diphenyl-amino)phenyl]benzidine (NPNPB) and combinations thereof, but is not limited to this.Preferably, the HIL 310 comprises or consists of NPNPB. The HIL 310 can be omitted according to the properties of the OLED D1.

[0081] The HTL 320 is located adjacent to the EML 340, between the first electrode 210 and the EML 340.In an exemplary embodiment, HTL 320 can be N,N'-Diphenyl-N,N'-bis(3-methylphenyl-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (designated as NPB or NPD), N,N'-Bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD), 4,4'-Bis(N-carbazolyl)-1,1'-biphenyl (CBP), Poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (Poly-TPD), Poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))] (TFB), 1,1-bis(4-(N,N'-di(p-tolyl)amino)phenyl)cyclohexane (TAPC), 3,5-Di(9H-carbazol-9-yl)-N,N-diphenylaniline (DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, N-(Biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine, N-([1,1'-Biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine and combinations thereof, but is not limited to these.Preferably, the HTL 320 NPB comprises or consists of.

[0082] The EML 340 can comprise a host (first host) and a dopant (first dopant) 342. For example, the EML 340 can emit green light. The organic metal compound with the structure of formulas 1 to 11 can, for example, be used as the dopant 342 in the EML 340. Furthermore, in a preferred example, 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP) is used as the host in the EML 340. The weight ratio of the host to the dopant in the EML 340 is preferably 70:30 to 99:1, more preferably 90:10 to 98:2.

[0083] The ETL 360 and the EIL 370 can be sequentially laminated between the EML 340 and the second electrode 220. The ETL 360 incorporates a material with high electron mobility to stably deliver electrons to the EML 340 via rapid electron transport.

[0084] As one example, the ETL 360 may include, but is not limited to, oxadiazole-based compounds, triazole-based compounds, phenanthroline-based compounds, benzoxazole-based compounds, benzothiazole-based compounds, benzimidazole-based compounds and / or triazine-based compounds.

[0085] Als Beispiel kann die ETL 360 Tris-(8-hydroxychinolin)aluminium (Alq3), Bis(2-methyl-8-chinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminium (BAlq), Lithiumchinolat (Liq), 2-Biphenyl-4-yl-5-(4-t-butylphenyl)-1,3,4-oxadiazol (PBD), Spiro-PBD, 1,3,5-Tris(N-phenylbenzimidazol-2-yl)benzol (TPBi), 4,7-Diphenyl-1,10-phenanthrolin (Bphen), 2,9-Bis(naphthalin-2-yl)-4,7-diphenyl-1,10-phenanthrolin (NBphen), 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthrolin (BCP), 3-(4-Biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazol (TAZ), 4-(Naphthalin-1-yl)-3,5-diphenyl-4H-1,2,4-triazol (NTAZ), 1,3,5-Tri(p-pyrid-3-yl-phenyl)benzol (TpPyPB), 2,4,6-Tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazin (TmPPPyTz), Poly[9,9-bis(3'-(N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluoren]-alt-2,7-(9,9-dioctylfluoren)] (PFNBr), Tris(phenylchinoxalin) (TPQ), Diphenyl-4-triphenysilyl-phenylphosphinoxid (TSPO1), 2-[4-(9,10-di-2-naphthalen-2-yl-2-anthracene-2-yl)phenyl]1-phenyl-1H-benzimidazole (ZADN) and combinations thereof, but is not limited to. Preferably, ETL 360 comprises or consists of ZADN.

[0086] The EIL 370 is positioned between the second electrode 220 and the ETL 360 and can improve the physical properties of the second electrode 220, thereby extending the lifetime of the OLED D1. By way of example, the EIL 370 can comprise, but is not limited to, an alkali metal halide or an alkaline earth metal halide, such as LiF, CsF, NaF, or BaF₂, and / or an organic metal compound such as Liq, lithium benzoate, or sodium stearate. The EIL 370 preferably comprises or consists of Liq. Alternatively, the EIL 370 can be omitted.

[0087] Alternatively, the electron transport material and the electron injection material can be mixed to form a single ETL-EIL. The electron transport material and the electron injection material can be present in a weight ratio of 4:1 to 1:4, particularly in a ratio of 2:1 to 1:2.

[0088] If holes are transferred to the second electrode 220 via the EML 340 and / or electrons are transferred to the first electrode 210 via the EML 340, the OLED D1 may exhibit a short lifetime and reduced luminous efficiency. To prevent these phenomena, the OLED D1 may, according to this aspect of the present invention, have at least one exciton barrier layer adjacent to the EML 340.

[0089] The OLED D1 can, for example, include the EBL 330 between the HTL 320 and the EML 340 to control and prevent electron transfers. As one example, EBL 330 may include TCTA, Tris[4-(diethylamino)phenyl]amine, N-(Biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, TAPC, MTDATA, 1,3-Bis(carbazol-9-yl)benzene (mCP), 3,3'-Bis(N-carbazolyl)-1,1'-biphenyl (mCBP), CuPc, N,N'-Bis[4-(bis(3-methylphenyl)amino)phenyl]-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD), TDAPB, DCDPA, 2,8-Bis(9-phenyl-9H-carbazol-3-yl)dibenzo[b,d]thiophene and combinations thereof, but is not limited to it. limited.

[0090] Furthermore, the OLED D1 can also include the HBL 350 as a second exciton barrier layer between the EML 340 and the ETL 360, preventing hole transfer from the EML 340 to the ETL 360. As an example, the HBL 350 can include, but is not limited to, oxadiazole-based, triazole-based, phenanthroline-based, benzoxazole-based, benzothiazole-based, benzimidazole-based, and / or triazine-based compounds, any of which can be used in the ETL 360.

[0091] HBL 350, for example, can include a compound with a relatively low HOMO energy level compared to the luminescent materials in EML 340. HBL 350 can include, but is not limited to, Alq3, BAlq, Liq, PBD, Spiro-PBD, BCP, Bis-4,5-(3,5-di-3-pyridylphenyl)-2-methylpyrimidine (B3PYMPM), Bis(2-(diphenylphosphino)phenyl)ether oxide (DPEPO), 9-(6-(9H-carbazol-9-yl)pyridin-3-yl)-9H-3,9'-bicarbazole, TSPO1, and combinations thereof.

[0092] As described above, EML 340 can comprise the host and the doping material 342. The doping material 342 can comprise the organic metal compound with the structures of formulas 1 to 11.

[0093] Der mit dem Dotierungsmaterial 342 verwendete Wirt kann 9-(3-(9H-Carbazol-9-yl)phenyl)-9H-carbazol-3-carbonitril (mCP-CN), CBP, mCBP, mCP, DPEPO, 2,8-Bis(diphenylphosphoryl)dibenzothiophen (PPT), 1,3,5-Tri[(3-pyridyl)-phen-3-yl]benzol (TmPyPB), 2,6-Di(9H-carbazol-9-yl)pyridin (PYD-2Cz), 2,8-Di(9H-carbazol-9-yl)dibenzothiophen (DCzDBT), 3',5'-Di(carbazol-9-yl)-[1,1'-biphenyl]-3,5-dicarbonitril (DCzTPA), 4'-(9H-Carbazol-9-yl)biphenyl-3,5-dicarbonitril(4'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitril (pCzB-2CN), 3'-(9H-Carbazol-9-yl)biphenyl-3,5-dicarbonitril (mCzB-2CN), TSPO1, 9-(9-Phenyl-9H-carbazol-6-yl)-9H-carbazol (CCP), 4-(3-(Triphe-nylen-2-yl)phenyl)dibenzo[b,d]thiophen, 9-(4-(9H-Carbazol-9-yl)phenyl)-9H-3,9'-bi-carbazol, 9-(3-(9H-Carbazol-9-yl)phenyl)-9H-3,9'-bicarbazol, 9-(6-(9H-Carbazol-9-yl)pyridin-3-yl)-9H-3,9'-bicarbazol, 9,9'-Diphenyl-9H,9'H-3,3'-bicarbazol (BCzPh), 1,3,5-Tris(carbazol-9-yl)benzol (TCP), TCTA, 4,4'-Bis(carbazol-9-yl)-2,2'-dimethyl-biphenyl (CDBP), 2,The host material may include, but is not limited to, 7-bis(carbazol-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,2',7,7'-tetrakis(carbazol-9-yl)-9,9-spirofluorene (Spiro-CBP), 3,6-bis(carbazol-9-yl)-9-(2-ethylhexyl)-9H-carbazole (TCz1). Preferably, the host material comprises or consists of CBP. The levels of the doping material 342 in the EML 340 may, for example, be between 1 wt% and 50 wt%, preferably between 1 wt% and 30 wt%, and in particular between 2.5 wt% and 10.0 wt%.

[0094] As described above, since the organic metal compound with the structures of formulas 1 to 11 exhibits a rigid chemical conformation, it can display excellent color purity and luminescence lifetime while maintaining its stable chemical conformation during the luminescence process. Changing the structure of the bidentate ligands and substituents allows the organic metal compound to control its luminescence color. Consequently, the OLED D1 can reduce its drive voltage and improve its luminescence efficiency and lifetime.

[0095] In the first example above, the OLED and the organic light emission display device comprise a single emission component that emits green light. Alternatively, the OLED can have multiple emission components (see Fig. 5) comprise, each of which includes an emission material layer with the organic metal compound having the structure of formulas 1 to 11.

[0096] In another exemplary aspect, an organic light emission display device can implement a full color, including white. Fig. Figure 4 is a schematic cross-sectional view representing an organic light emission indicator device according to another exemplary aspect of the present invention.

[0097] As in Fig. As shown in Figure 4, the organic light emission indicator device 400 comprises a first substrate 402 defining each of a red pixel area RP, a green pixel area GP and a blue pixel area BP, a second substrate 404 facing the first substrate 402, a thin-film transistor Tr over the first substrate 402, an organic light-emitting diode D positioned between the first and second substrates 402 and 404 emitting white (W) light, and a color filter layer 480 positioned between the organic light-emitting diode D and the second substrate 404.

[0098] Each of the first and second substrates 402 and 404 can comprise, but is not limited to, glass, a flexible material, and / or polymer plastic. For example, each of the first and second substrates 402 and 404 can consist of PI, PES, PEN, PET, PC, and combinations thereof. The first substrate 402, over which a thin-film transistor Tr and an organic light-emitting diode D are arranged, forms a matrix substrate.

[0099] A buffer layer 406 can be arranged above the first substrate 402, and the thin-film transistor Tr is arranged above the buffer layer 406 corresponding to each of the red pixel areas RP, the green pixel areas GP, and the blue pixel areas BP. However, the buffer layer 406 can also be omitted.

[0100] A semiconductor layer 410 is arranged above the buffer layer 406. The semiconductor layer 410 can consist of an oxide semiconductor material or polycrystalline silicon.

[0101] A gate insulation layer 420 with an insulating material, for example an inorganic insulating material such as silicon dioxide (SiO₂). x ) or silicon nitride (SiN x ), is located on semiconductor layer 410.

[0102] A gate electrode 430, made of an electrically conductive material such as a metal, is arranged above the gate insulating layer 420 such that it corresponds to a center of the semiconductor layer 410. An intermediate insulating layer 440 with an insulating material, for example an inorganic insulating material such as silicon dioxide (SiO₂), is also present. x ) or silicon nitride (SiN x ) or an organic insulating material such as benzocyclobutene or photoacrylic, is arranged on the gate electrode 430.

[0103] The intermediate insulating layer 440 has a first and a second semiconductor layer contact hole 442 and 444, which expose both sides of the semiconductor layer 410. The first and the second semiconductor layer contact holes 442 and 444 are arranged above opposite sides of the gate electrode 430 at a distance from the gate electrode 430.

[0104] A source electrode 452 and a drain electrode 454, made of an electrically conductive material such as a metal, are arranged on the intermediate insulating layer 440. The source electrode 452 and the drain electrode 454 are spaced apart from each other with respect to the gate electrode 430 and contact both sides of the semiconductor layer 410 through the first and second semiconductor layer contact holes 442 and 444, respectively.

[0105] The semiconductor layer 410, the gate electrode 430, the source electrode 452 and the drain electrode 454 form the thin-film transistor Tr, which acts as a control element.

[0106] Although in Fig. Figure 4 (not shown) shows that a gate line and a data line, which intersect to define a pixel area, and a switching element connected to the gate line and the data line, can further be formed within the pixel area. The switching element is connected to the thin-film transistor Tr, which is a driver element. Additionally, a power line is spaced parallel to or spaced from the gate line or the data line, and the thin-film transistor Tr can further include a storage capacitor configured to maintain a constant gate electrode voltage for a frame.

[0107] A passivation layer 460 is arranged on the source and drain electrodes 452 and 454, covering the entire first substrate 402 of the thin-film transistor Tr. The passivation layer 460 has a drain contact hole 462 that exposes the drain electrode 454 of the thin-film transistor Tr.

[0108] The organic light-emitting diode (OLED) D is arranged above the passivation layer 460. The OLED D comprises a first electrode 510, which is connected to the drain electrode 454 of the thin-film transistor Tr, a second electrode 520, which faces the first electrode 510, and an emission layer 530, which is arranged between the first and second electrodes 510 and 520.

[0109] The first electrode 510, configured for each pixel area, can be an anode and can comprise an electrically conductive material with a relatively high work function value. For example, the first electrode 510 can comprise ITO, IZO, ITZO, SnO, ZnO, ICO, and / or AZO. Alternatively, a reflective electrode or reflective layer can be arranged beneath the first electrode 510. The reflective electrode or reflective layer can comprise, for example, Ag or an APC alloy, but is not limited to these materials.

[0110] A bench layer 464 is arranged on the passivation layer 460 to cover edges of the first electrode 510. The bench layer 464 exposes a center of the first electrode 510 corresponding to each of the red pixel RP, the green pixel GP, and the blue pixel BP. However, the bench layer 464 can also be omitted.

[0111] An emission layer 530, which can comprise several emission parts, is arranged on the first electrode 510. As in Fig. 5 and Fig. As shown in Figure 6, the emission layer 530 can comprise several emission parts 600, 700, 700A and 800 and at least one charge generation layer 680 and 780. Each of the emission parts 600, 700, 700A and 800 comprises at least one emission material layer and can further comprise a hole injection layer, a hole transport layer, an electron barrier layer, a hole barrier layer, an electron transport layer and / or an electron injection layer.

[0112] The second electrode 520 is arranged above the first substrate 402 and between the emission layer 530 and the second substrate 404. The second electrode 520 can be arranged over an entire display area and can comprise an electrically conductive material with a relatively low work function value compared to the first electrode 510, and can be a cathode. The second electrode 520 can, for example, comprise Al, Mg, Ca, Ag, an alloy thereof, or combinations thereof, such as Al-Mg, but is not limited to these materials.

[0113] Since the light emitted by the emission layer 530 falls onto the color filter layer 480 through the second electrode 520 in the organic light emission indicator device 400 according to the second embodiment of the present invention, the second electrode 520 has a thin thickness so that the light can pass through.

[0114] The color filter layer 480 is arranged above the OLED D and comprises a red color filter 482, a green color filter 484, and a blue color filter 486, each of which is arranged according to the red pixel RP, the green pixel GP, and the blue pixel BP, respectively. Although in Fig. Not shown in Figure 4, the color filter layer 480 can be attached to the OLED D by an adhesive layer. Alternatively, the color filter layer 480 can be arranged directly on the OLED D.

[0115] Furthermore, an encapsulation film can be arranged over the second electrode 520 to prevent external moisture from penetrating the OLED D. The encapsulation film can have, but is not limited to, a laminated structure of a first inorganic insulating film, an organic insulating film, and a second inorganic insulating film (see 170 in Fig. 2) In addition, a polarizing plate can be attached to the second substrate 404 to reduce the reflection of external light. The polarizing plate can, for example, be a circular polarizing plate.

[0116] In Fig. 4. The light emitted by the OLED D is transmitted through the second electrode 520 and the color filter layer 480, which is arranged above the OLED D. Alternatively, the light emitted by the OLED D is transmitted through the first electrode 510, and the color filter layer 480 can be arranged between the OLED D and the first substrate 402. Furthermore, a color conversion layer can be formed between the OLED D and the color filter layer 480. The color conversion layer can comprise a red color conversion layer, a green color conversion layer, and a blue color conversion layer, each arranged according to each pixel (RP, GP, and BP) to convert the white (W) light into red, green, and blue light, respectively. The organic light emission display device 400 can also include the color conversion film instead of the color filter layer 480.

[0117] As described above, the white (W) light emitted by the OLED D is passed through the red color filter 482, the green color filter 484 and the blue color filter 486, each of which is arranged according to the red pixel area RP, the green pixel area GP and the blue pixel area BP respectively, so that red, green and blue light is displayed in the red pixel area RP, in the green pixel area GP and in the blue pixel area BP.

[0118] Fig. Figure 5 is a schematic cross-sectional view representing an organic light-emitting diode with a tandem structure of two emission parts. As shown in Fig. Figure 5 shows that the organic light-emitting diode (OLED) D2, according to the exemplary embodiment, comprises a first and a second electrode 510 and 520 facing each other, and an emission layer 530 arranged between the first and second electrodes 510 and 520. The emission layer 530 comprises a first emission part 600 arranged between the first and second electrodes 510 and 520, a second emission part 700 arranged between the first emission part 600 and the second electrode 520, and a charge generation layer (CGL) 680 arranged between the first and second emission parts 600 and 700.

[0119] The first electrode 510 can be an anode and can comprise an electrically conductive material with a relatively high work function value. For example, the first electrode 510 can comprise ITO, IZO, ITZO, SnO, ZnO, ICO, and / or AZO. The second electrode 520 can be a cathode and can comprise an electrically conductive material with a relatively low work function value. The second electrode 520 can comprise, for example, Al, Mg, Ca, Ag, an alloy thereof, or combinations thereof, such as Al-Mg, but is not limited to these.

[0120] The first emission part 600 comprises a first EML (EML1) 640. The first emission part 600 may further comprise a HIL 610 arranged between the first electrode 510 and the EML1 640, a first HTL (HTL1) 620 arranged between the HIL 610 and the EML1 640, and / or a first ETL (ETL1) 660 arranged between the EML1 640 and the CGL 680. Alternatively, the first emission part 600 may further comprise a first EBL (EBL1) 630 arranged between the HTL1 620 and the EML1 640, and / or a first HBL (HBL1) 650 arranged between the EML1 640 and the ETL1 660.

[0121] The second emission part 700 comprises a second EML (EML2) 740. The second emission part 700 may further comprise a second HTL (HTL2) 720 arranged between the CGL 680 and the EML2 740, a second ETL (ETL2) 760 arranged between the second electrode 520 and the EML2 740, and / or an EIL 770 arranged between the second electrode 520 and the ETL2 760. Alternatively, the second emission part 700 may further comprise a second EBL (EBL2) 730 arranged between the HTL2 720 and the EML2 740, and / or a second HBL (HBL2) 750 arranged between the EML2 740 and the ETL2 760.

[0122] The EML1 640 and / or the EML2 740 can comprise the organic metal compound with the structure of formulas 1 to 11 to emit a green color. The other EML1 640 and the EML2 740 can emit a blue color, enabling the OLED D2 to achieve white (W) emission. The OLED D2, in which the EML2 740 comprises the organic metal compound with the structure of formulas 1 to 11, is described in detail below.

[0123] The HIL 610 is arranged between the first electrode 510 and the HTL1 620 and improves an interfacial property between the inorganic first electrode 510 and the organic HTL1 620. In an exemplary embodiment, the HIL 610 can comprise, but is not limited to, MTDATA, NATA, 1T-NATA, 2T-NATA, CuPc, TCTA, NPB (NPD), HAT-CN, TDAPB, PEDOT / PSS, F4TCNQ, N-(Biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, NPNPB, and combinations thereof. The HIL 610 can be omitted according to the properties of the OLED D2.

[0124] Each of the HTL1 620 and the HTL2 720 may include, but is not limited to, TPD, NPB (NPD), DNTPD, CBP, Poly-TPD, TFB, TAPC, DCDPA, N-(Biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carba-zol-3-yl)phenyl)-9H-fluoren-2-amine, N-(Biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine, N-([1,1'-Biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine or combinations thereof.

[0125] Each of the ETL1 660 and the ETL2 760 facilitates electron transport in each of the first emission part 600 and the second emission part 700, respectively. For example, each of the ETL1 660 and the ETL2 760 can independently include, but is not limited to, oxadiazole-based compounds, triazole-based compounds, phenanthroline-based compounds, benzoxazole-based compounds, benzothiazole-based compounds, benzimidazole-based compounds, and triazine-based compounds. For example, each of the ETL1 660 and the ETL2 770 can include, but is not limited to, Alq3, BAlq, Liq, PBD, Spiro-PBD, TPBi, Bphen, NBphen, BCP, TAZ, NTAZ, TpPyPB, TmPPPyTz, PFNBr, TPQ, TSPO1, ZADN, or combinations thereof.

[0126] The EIL 770 is positioned between the second electrode 520 and the ETL2 760 and can improve the physical properties of the second electrode 520, thereby extending the lifetime of the OLED D2. By way of example, the EIL 770 can comprise, but is not limited to, an alkali metal halide or an alkaline earth metal halide such as LiF, CsF, NaF, or BaF2, and / or an organic metal compound such as Liq, lithium benzoate, or sodium stearate.

[0127] Each of the EBL1 630 and the EBL2 730 may independently include, but is not limited to, TCTA, Tris[4-(diethyla-mino)phenyl]amine, N-(Biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, TAPC, MTDATA, mCP, mCBP, CuPc, DNTPD, TDAPB, DCDPA, 2,8-Bis(9-phenyl-9H-carbazol-3-yl)dibenzo[b,d]thiophene or combinations thereof.

[0128] Each of HBL1 650 and HBL2 750 may include oxadiazole-based compounds, triazole-based compounds, phenanthroline-based compounds, benzoxazole-based compounds, benzothiazole-based compounds, benzimidazole-based compounds, and / or triazine-based compounds, any of which may be used in ETL1 660 and ETL2 760, respectively, but are not limited to them. For example, each of HBL1 650 and HBL2 750 may independently include, but are not limited to, Alq3, BAlq, Liq, PBD, Spiro-PBD, BCP, B3PYMPM, DPEPO, 9-(6-(9H-carbazol-9-yl)pyridin-3-yl)-9H-3,9'-bicarbazole, TSPO1, or combinations thereof.

[0129] The CGL 680 is located between the first emission part 600 and the second emission part 700. The CGL 680 comprises an N-type CGL (N-CGL) 685, located adjacent to the first emission part 600, and a P-type CGL (P-CGL) 690, located adjacent to the second emission part 700. The N-CGL 685 transports electrons to the EML1 640 of the first emission part 600, and the P-CGL 690 transports holes to the EML2 740 of the second emission part 700.

[0130] N-CGL 685 can be an organic layer doped with an alkali metal such as Li, Na, K, and Cs and / or an alkaline earth metal such as Mg, Sr, Ba, and Ra. The host in N-CGL 685 can include, but is not limited to, Bphen and MTDATA. The concentrations of the alkali metal or alkaline earth metal in N-CGL 685 can range from 0.01 wt% to 30 wt%.

[0131] The P-CGL 690 can be an inorganic material selected from the group consisting of WO x , MoO x , V2O5 and combinations thereof, and / or an organic material selected from the group consisting of NPD, HAT-CN, F4TCNQ, TPD, N,N,N',N'-tetranaphthalenyl benzidine (TNB), TCTA, N,N'-dioctyl-3,4,9,10-perylenedi-carboximide (PTCDI-C8) and combinations thereof, but is not limited to.

[0132] The EML1 640 can be a blue EML. In this case, the EML1 640 can be a blue EML, a sky-blue EML, or a deep-blue EML. The EML1 640 can comprise a host and a blue dopant material. The host can be identical to the first host, and the blue dopant material can be a blue phosphorescent material, a blue fluorescent material, and / or a blue delayed-fluorescence material.

[0133] The EML2 740 can comprise a lower EML 740A, positioned between the EBL2 730 and the HBL2 750, and an upper EML 740B, also positioned between the lower EML 740A and the HBL2 750. One of the lower EML 740A and the upper EML 740B can emit red color, and the other can emit green color. The EML2 740, in which the lower EML 740A emits green color and the upper EML 740B emits red color, is described in detail below.

[0134] The lower EML 740A comprises a first host and a first doping material 742. The first host can be mCP-CN, CBP, mCBP, mCP, DPEPO, PPT, TmPyPB, PYD-2Cz, DCzDBT, DCzTPA, pCzB-2CN, mCzB-2CN, TSPO1, CCP, 4-(3-(Triphenylen-2-yl)phenyl)dibenzo[b,d]thiophene, 9-(4-(9H-Carbazol-9-yl)phenyl)-9H-3,9'-bicarbazole, 9-(3-(9H-Carbazol-9-yl)phenyl)-9H-3,9'-bicarbazole, 9-(6-(9H-Carbazol-9-yl)pyridin-3-yl)-9H-3,9'-bicarbazole, BCzPh, TCP, TCTA, The first dopant material 742 may include, but is not limited to, CDBP, DMFL-CBP, Spiro-CBP, TCz1, and combinations thereof. It may comprise the organic metal compound with the structure of formulas 1 to 11 to emit a green color. The concentrations of the first dopant material 742 in the lower EML 740A may, for example, be between 1 wt% and 50 wt%, preferably between 1 wt% and 30 wt%, and particularly between 2.5 wt% and 10.0 wt%.

[0135] The upper EML 740B comprises a host and a red dopant material. The host can be identical to the first host, and the red dopant material can be a red phosphorescent material, a red fluorescent material, and / or a red material with delayed fluorescence.

[0136] The OLED D2, according to this aspect, has a tandem structure and comprises the organic metal compound with the structure of formulas 1 to 11. The OLED D2 with the organic metal compound, featuring excellent thermal properties, a rigid chemical conformation, and adjustable luminescence colors, can lower its drive voltage and improve its luminous efficiency and luminous lifespan.

[0137] The OLED can have three or more emission parts to form a tandem structure. Fig. Figure 6 is a schematic cross-sectional view representing an organic light-emitting diode according to yet another exemplary aspect of the present invention. As in Fig. As shown in Figure 6, the organic light-emitting diode (OLED) D3 comprises a first and a second electrode 510 and 520 facing each other, and an emission layer 530A positioned between the first and the second electrode 510 and 520. The emission layer 530A comprises a first emission part 600, which is arranged between the first and the second electrode 510 and 520, a second emission part 700A, which is arranged between the first emission part 600 and the second electrode 520, a third emission part 800, which is arranged between the second emission part 700A and the second electrode 520, a first charge generation layer (CGL1) 680, which is arranged between the first and the second emission part 600 and 700A, and a second charge generation layer (CGL2) 780, which is arranged between the second and the third emission part 700A and 800.

[0138] The first emission part 600 comprises a first EML (EML1) 640. The first emission part 600 may further comprise a HIL 610 arranged between the first electrode 510 and the EML1 640, a first HTL (HTL1) 620 arranged between the HIL 610 and the EML1 640, and / or a first ETL (ETL1) 660 arranged between the EML1 640 and the first CGL1 680. Alternatively, the first emission part 600 may further comprise a first EBL (EBL1) 630 arranged between the HTL1 620 and the EML1 640, and / or a first HBL (HBL1) 650 arranged between the EML1 640 and the ETL1 660.

[0139] The second emission part 700A comprises a second EML (EML2) 740. The second emission part 700A may further comprise a second HTL (HTL2) 720, arranged between the CGL1 680 and the EML2 740, and / or a second ETL (ETL2) 760, arranged between the second electrode 520 and the EML2 740. Alternatively, the second emission part 700A may further comprise a second EBL (EBL2) 730, arranged between the HTL2 720 and the EML2 740, and / or a second HBL (HBL2) 750, arranged between the EML2 740 and the ETL2 760.

[0140] The third emission part 800 comprises a third EML (EML3) 840. The third emission part 800 may further comprise a third HTL (HTL3) 820 arranged between the CGL2 780 and the EML3 840, a third ETL (ETL3) 860 arranged between the second electrode 520 and the EML3 840, and / or an EIL 870 arranged between the second electrode 520 and the ETL3 860. Alternatively, the third emission part 800 may further comprise a third EBL (EBL3) 830 arranged between the HTL3 820 and the EML3 840, and / or a third HBL (HBL3) 850 arranged between the EML3 840 and the ETL3 860.

[0141] The EML1 640, the EML2 740, and / or the EML3 840 can comprise the organic metal compound with the structure of formulas 1 to 11. For example, one of the EML1 640, the EML2 740, and the EML3 840 can emit green light. Furthermore, at least one other of the EML1 640, the EML2 740, and the EML3 840 can emit blue light. If a red light-emitting material is also included in one of the EML1 640, the EML2 740, and the EML3 840, the OLED D3 can achieve white emission. The OLED in which the EML2 740 comprises the organic metal compound with the structure of formulas 1 to 11 to emit green light, and each of the EML1 640 and the EML3 840 emits blue light, is described in detail below.

[0142] CGL1 680 is located between the first emission part 600 and the second emission part 700A, and CGL2 780 is located between the second emission part 700A and the third emission part 800. CGL1 680 comprises a first N-type CGL (N-CGL1) 685 located adjacent to the first emission part 600 and a first P-type CGL (P-CGL1) 690 located adjacent to the second emission part 700A. CGL2 780 comprises a second N-type CGL (N-CGL2) 785 located adjacent to the second emission part 700A and a second P-type CGL (P-CGL2) 790 located adjacent to the third emission part 800. Each of the N-CGL1 685 and the N-CGL2 785 transports electrons to the EML1 640 of the first emission part 600 and to the EML2 740 of the second emission part 700A respectively, and each of the P-CGL1 690 and the P-CGL2 790 transports holes to the EML2 740 of the second emission part 700A and to the EML3 840 of the third emission part 800 respectively.

[0143] Each of the EML1 640 and the EML3 840 can independently be a blue EML. In this case, each of the EML1 640 and the EML3 840 can independently be a blue EML, a sky-blue EM, or a deep-blue EML. Each of the EML1 640 and the EML3 840 can independently comprise a host and a blue dopant material. The host can be identical to the first host, and the blue dopant material can be a blue phosphorescent material, a blue fluorescent material, and / or a blue delayed-fluorescence material. As an example, the blue dopant material in the EML1 640 can have a different color and luminescence efficiency than the blue dopant material in the EML3 840.

[0144] The EML2 740 can comprise a lower EML 740A, positioned between the EBL2 730 and the HBL2 750, and an upper EML 740B, also positioned between the lower EML 740A and the HBL2 750. One of the lower EML 740A and the upper EML 740B can emit red color, and the other can emit green color. The EML2 740, in which the lower EML 740A emits green color and the upper EML 740B emits red color, is described in detail below.

[0145] The lower EML 740A can comprise a first host and a first dopant material 742. As an example, the first dopant material 742 comprises the organic metal compound with the structure of formulas 1 to 11 to emit a green color. The concentrations of the dopant material 742 in the lower EML 740A can be, for example, between 1 wt% and 50 wt%, preferably between 1 wt% and 30 wt%, and particularly between 2.5 wt% and 10.0 wt%.

[0146] The upper EML 740B comprises a host and a red dopant material. The host can be identical to the first host, and the red dopant material can be a red phosphorescent material, a red fluorescent material, and / or a red material with delayed fluorescence.

[0147] The OLED D3, according to this aspect, comprises the organic metal compound with the structure of formulas 1 to 6 in at least one emission material layer. The organic metal compound can maintain its stable chemical conformations during the luminescence process. The OLED with the organic metal compound and three emission components can achieve white luminescence with improved luminous efficacy, color purity, and luminous lifetime. Synthesis Example 1: Synthesis of Compound 5(1) Synthesis of Intermediate A-2

[0148] Compounds SM-1 (31.9 g, 0.10 mol), SM-2 (13.61 g, 0.20 mol), (1R,2R)-cyclohexane-1,2-diamine (22.83 g, 0.20 mol), CuI(I) (1.90 g, 0.01 mol), and Cs₂CO₃ (97.75 g, 0.30 mol), dissolved in DMF (500 mL), were placed in a 1 L round-bottom flask under a nitrogen atmosphere. The solution was heated overnight with stirring. After the reaction was complete, the reaction vessel was cooled to room temperature (25 °C). The solution was filtered through a Celite mat filter, and the organic layer was extracted and separated using ethyl acetate and distilled water. The water in the organic layer was removed with anhydrous MgSO₄, and the organic layer was then filtered and concentrated under reduced pressure. The crude product was recrystallized with ethyl acetate and hexane to give the intermediate product A-2 (19.96 g, yield: 65%). (2) Synthesis of intermediate A-1

[0149] The intermediate A-2 (15.36 g, 0.05 mol), dissolved in acetonitrile (250 ml), was transferred to a 500 ml round-bottom flask under a nitrogen atmosphere. Iodomethane (42.58 g, 0.03 mol) was added to the reaction solution, and the solution was stirred at room temperature for 24 hours. After the reaction was complete, the solution was filtered and concentrated under reduced pressure to give the intermediate A-1 (23.42 g, yield: 95%). (3) Synthesis of intermediate A

[0150] The intermediate A-1 (24.66 g, 0.05 mol) and silver oxide (5.80 g, 0.025 mol), dissolved in acetonitrile (250 ml), were placed in a 500 ml round-bottom flask under a nitrogen atmosphere, and the solution was then stirred at room temperature for 24 hours. After the reaction was complete, the solution was concentrated under reduced pressure to give intermediate A (24.16 g, yield: 98%) without further purification for the next reaction. (4) Synthesis of compound 5

[0151] The iridium precursor M1 (1.64 g, 1.5 mmol) and the intermediate A (1.66 g, 3 mmol), dissolved in o-xylene (150 mL), were placed in a 150 mL round-bottom flask under a nitrogen atmosphere. The solution was then heated under reflux with stirring for 18 hours. After the reaction was complete, the solution was cooled to room temperature. The organic layer was then extracted with dichloromethane and distilled water, and the water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate : hexane = 25:75) to give compound 5 (1.13 g, yield: 92%). Synthesis Example 2: Synthesis of Compound 6(1) Synthesis of Intermediate B-2

[0152] Compounds SM-1 (31.9 g, 0.10 mol), SM-3 (23.61 g, 0.20 mol), (1R,2R)-cyclohexane-1,2-diamine (22.83 g, 0.20 mol), CuI(I) (1.90 g, 0.01 mol), and Cs₂CO₃ (97.75 g, 0.30 mol), dissolved in DMF (500 mL), were placed in a 1 L round-bottom flask under a nitrogen atmosphere. The solution was heated overnight with stirring. After the reaction was complete, the reaction vessel was cooled to room temperature. The solution was filtered through a Celite mat filter, and the organic layer was extracted and separated using ethyl acetate and distilled water. The water in the organic layer was removed with anhydrous MgSO₄, and the organic layer was then filtered and concentrated under reduced pressure. The crude product was recrystallized with ethyl acetate and hexane to give intermediate product B-2 (18.57 g, yield: 52%). (2) Synthesis of intermediate B-1

[0153] The intermediate B-2 (17.86 g, 0.05 mol), dissolved in acetonitrile (250 ml), was placed in a 500 ml round-bottom flask under a nitrogen atmosphere. Iodomethane (42.58 g, 0.03 mol) was added to the reaction solution, and the solution was stirred at room temperature for 24 hours. After the reaction was complete, the solution was filtered and concentrated under reduced pressure to give the intermediate B-1 (26.61 g, yield: 98%). (3) Synthesis of intermediate B

[0154] The intermediate B-1 (27.16 g, 0.05 mol) and silver oxide (5.80 g, 0.025 mol), dissolved in acetonitrile (250 ml), were placed in a 500 ml round-bottom flask under a nitrogen atmosphere, and the solution was then stirred at room temperature for 24 hours. After the reaction was complete, the solution was concentrated under reduced pressure to give intermediate B (25.53 g, yield: 94%) without further purification for the next reaction. (4) Synthesis of compound 6

[0155] The iridium precursor M1 (1.64 g, 1.5 mmol) and the intermediate B (1.82 g, 3 mmol), dissolved in o-xylene (150 mL), were placed in a 150 mL round-bottom flask under a nitrogen atmosphere. The solution was then heated under reflux with stirring for 18 hours. After the reaction was complete, the solution was cooled to room temperature. The organic layer was then extracted with dichloromethane and distilled water, and the water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate : hexane = 25:75) to give compound 6 (1.15 g, yield: 88%). Synthesis Example 3: Synthesis of Compound 50(1) Synthesis of Intermediate C-1

[0156] The intermediate A-2 (15.36 g, 0.05 mol), dissolved in acetonitrile (250 ml), was transferred to a 500 ml round-bottom flask under a nitrogen atmosphere. 2-Iodopropane (51.00 g, 0.03 mol) was added to the reaction solution, and the solution was stirred at room temperature for 24 minutes. After the reaction was complete, the solution was filtered and concentrated under reduced pressure to give the intermediate C-1 (24.00 g, yield: 92%). (2) Synthesis of intermediate C

[0157] The intermediate C-1 (26.06 g, 0.05 mol) and silver oxide (5.80 g, 0.025 mol), dissolved in acetonitrile (250 ml), were placed in a 500 ml round-bottom flask under a nitrogen atmosphere, and the solution was then stirred at room temperature for 24 hours. After the reaction was complete, the solution was concentrated under reduced pressure to give the intermediate C (23.97 g, yield: 92%) without further purification for the next reaction. (3) Synthesis of compound 50

[0158] The iridium precursor M1 (1.64 g, 1.5 mmol) and the intermediate C (1.74 g, 3 mmol), dissolved in o-xylene (150 mL), were placed in a 150 mL round-bottom flask under a nitrogen atmosphere. The solution was then heated under reflux with stirring for 18 hours. After the reaction was complete, the solution was cooled to room temperature. The organic layer was then extracted with dichloromethane and distilled water, and the water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate : hexane = 25:75) to give compound 50 (1.04 g, yield: 82%). Synthesis Example 4: Synthesis of Compound 51(1) Synthesis of Intermediate D-1

[0159] The intermediate B-2 (17.86 g, 0.05 mol), dissolved in acetonitrile (250 ml), was transferred to a 500 ml round-bottom flask under a nitrogen atmosphere. 2-Iodopropane (51.00 g, 0.03 mol) was added to the reaction solution, and the solution was stirred at room temperature for 24 hours. After the reaction was complete, the solution was filtered and concentrated under reduced pressure to give the intermediate D-1 (27.42 g, yield: 96%). (2) Synthesis of intermediate D

[0160] The intermediate D-1 (28.56 g, 0.05 mol) and silver oxide (5.80 g, 0.025 mol), dissolved in acetonitrile (250 ml), were placed in a 500 ml round-bottom flask under a nitrogen atmosphere, and the solution was stirred at room temperature for 24 hours. After the reaction was complete, the solution was concentrated under reduced pressure to give the intermediate D (27.42 g, yield: 96%) without further purification for the next reaction. (3) Synthesis of compound 51

[0161] The iridium precursor M1 (1.64 g, 1.5 mmol) and the intermediate D (1.90 g, 3 mmol), dissolved in o-xylene (150 mL), were placed in a 150 mL round-bottom flask under a nitrogen atmosphere. The solution was then heated under reflux with stirring for 18 hours. After the reaction was complete, the solution was cooled to room temperature. The organic layer was then extracted with dichloromethane and distilled water, and the water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate : hexane = 25:75) to give compound 51 (1.04 g, yield: 87%). Synthesis example 5: Synthesis of compound 65

[0162] The iridium precursor M2 (1.69 g, 1.5 mmol) and the intermediate C (1.74 g, 3 mmol), dissolved in o-xylene (150 mL), were placed in a 150 mL round-bottom flask under a nitrogen atmosphere. The solution was then heated under reflux with stirring for 18 hours. After the reaction was complete, the solution was cooled to room temperature. The organic layer was then extracted with dichloromethane and distilled water, and the water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate : hexane = 25:75) to give compound 65 (1.10 g, yield: 83%). Synthesis example 6: Synthesis of compound 66

[0163] The iridium precursor M2 (1.69 g, 1.5 mmol) and the intermediate D (1.90 g, 3 mmol), dissolved in o-xylene (150 mL), were placed in a 150 mL round-bottom flask under a nitrogen atmosphere. The solution was then heated under reflux with stirring for 18 hours. After the reaction was complete, the solution was cooled to room temperature. The organic layer was then extracted with dichloromethane and distilled water, and the water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate : hexane = 25:75) to give compound 66 (1.11 g, yield: 80%). Synthesis Example 7: Synthesis of Compound 95(1) Synthesis of Intermediate E-1

[0164] The intermediate A-2 (15.36 g, 0.05 mol), dissolved in acetonitrile (250 ml), was transferred to a 500 ml round-bottom flask under a nitrogen atmosphere. 1-Iodobutane (55.21 g, 0.03 mol) was added to the reaction solution, and the solution was stirred at room temperature for 24 hours. After the reaction was complete, the solution was filtered and concentrated under reduced pressure to give the intermediate E-1 (24.88 g, yield: 36%). (2) Synthesis of intermediate E

[0165] The intermediate E-1 (26.76 g, 0.05 mol) and silver oxide (5.80 g, 0.025 mol), dissolved in acetonitrile (250 ml), were placed in a 500 ml round-bottom flask under a nitrogen atmosphere, and the solution was then stirred at room temperature for 24 hours. After the reaction was complete, the solution was concentrated under reduced pressure to give the intermediate E (24.88 g, yield: 93%) without further purification for the next reaction. (3) Synthesis of compound 95

[0166] The iridium precursor M1 (1.64 g, 1.5 mmol) and the intermediate E (1.80 g, 3 mmol), dissolved in o-xylene (150 mL), were placed in a 150 mL round-bottom flask under a nitrogen atmosphere. The solution was then heated under reflux with stirring for 18 hours. After the reaction was complete, the solution was cooled to room temperature. The organic layer was then extracted with dichloromethane and distilled water, and the water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate : hexane = 25:75) to give compound 95 (1.11 g, yield: 86%). Synthesis Example 8: Synthesis of Compound 96(1) Synthesis of Intermediate F-1

[0167] The intermediate B-2 (17.86 g, 0.05 mol), dissolved in acetonitrile (250 ml), was transferred to a 500 ml round-bottom flask under a nitrogen atmosphere. 1-Iodobutane (55.21 g, 0.03 mol) was added to the reaction solution, and the solution was stirred at room temperature for 24 hours. After the reaction was complete, the solution was filtered and concentrated under reduced pressure to give the intermediate F-1 (25.75 g, yield: 88%). (2) Synthesis of intermediate F

[0168] The intermediate F-1 (29.26 g, 0.05 mol) and silver oxide (5.80 g, 0.025 mol), dissolved in acetonitrile (250 ml), were placed in a 500 ml round-bottom flask under a nitrogen atmosphere, and the solution was then stirred at room temperature for 24 hours. After the reaction was complete, the solution was concentrated under reduced pressure to give the intermediate F (26.04 g, yield: 89%) without further purification for the next reaction. (3) Synthesis of compound 96

[0169] The iridium precursor M1 (1.64 g, 1.5 mmol) and the intermediate F (1.94 g, 3 mmol), dissolved in o-xylene (150 mL), were placed in a 150 mL round-bottom flask under a nitrogen atmosphere. The solution was then heated under reflux with stirring for 18 hours. After the reaction was complete, the solution was cooled to room temperature. The organic layer was then extracted with dichloromethane and distilled water, and the water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate : hexane = 25:75) to give compound 96 (1.07 g, yield: 78%). Synthesis example 9: Synthesis of compound 110

[0170] The iridium precursor M2 (1.69 g, 1.5 mmol) and the intermediate E (1.80 g, 3 mmol), dissolved in o-xylene (150 mL), were placed in a 150 mL round-bottom flask under a nitrogen atmosphere. The solution was then heated under reflux with stirring for 18 hours. After the reaction was complete, the solution was cooled to room temperature. The organic layer was then extracted with dichloromethane and distilled water, and the water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate : hexane = 25:75) to give compound 110 (1.14 g, yield: 85%). Synthesis example 10: Synthesis of compound 111

[0171] The iridium precursor M2 (1.69 g, 1.5 mmol) and the intermediate F (1.94 g, 3 mmol), dissolved in o-xylene (150 mL), were placed in a 150 mL round-bottom flask under a nitrogen atmosphere. The solution was then heated under reflux with stirring for 18 hours. After the reaction was complete, the solution was cooled to room temperature. The organic layer was then extracted with dichloromethane and distilled water, and the water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate : hexane = 25:75) to give compound 111 (1.07 g, yield: 76%). Synthesis Example 11: Synthesis of Compound 226(1) Synthesis of the Iridium Precursor M3

[0172] Iridium(III) trichloride hydrate (2.60 g, 8.7 mmol) and intermediate A (19.37 g, 34.9 mmol), dissolved in 2-(2-methoxyethoxy)ethanol (300 mL), were placed in a 500 mL round-bottom flask under a nitrogen atmosphere. The solution was heated to 185 °C and stirred for 18 hours. After the reaction was complete, the solution was cooled to room temperature and filtered with Celite. The solution was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate : hexane = 25:75) to give the iridium precursor M3 (8.46 g, yield: 56%). (2) Synthesis of compound 226

[0173] The iridium precursor M3 (2.60 g, 1.5 mmol) and compound L1 (0.47 g, 3 mmol), dissolved in toluene (100 mL), were placed in a 250 mL round-bottom flask under a nitrogen atmosphere. The solution was then heated under reflux with stirring for 24 hours. After the reaction was complete, the solution was cooled to room temperature. The organic layer was then extracted with dichloromethane and distilled water, and the water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: toluene:hexane = 1:1) to give compound 226 (1.32 g, yield: 89%). Synthesis example 12: Synthesis of compound 228

[0174] The iridium precursor M3 (2.60 g, 1.5 mmol) and compound L2 (0.30 g, 3 mmol), dissolved in a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL), were placed in a 150 mL round-bottom flask under a nitrogen atmosphere, and the solution was stirred at 135 °C for 24 hours. After the reaction was complete, the solution was cooled to room temperature, and the organic layer was extracted with dichloromethane and distilled water. The water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: toluene:hexane = 1:3) to give compound 228 (1.66 g, yield: 92%). Synthesis Example 13: Synthesis of Compound 230(1) Synthesis of the Iridium Precursor M4

[0175] Iridium(III) trichloride hydrate (2.60 g, 8.7 mmol) and intermediate C (20.35 g, 34.9 mmol), dissolved in 2-(2-methoxyethoxy)ethanol (300 mL), were placed in a 500 mL round-bottom flask under a nitrogen atmosphere. The solution was heated to 185 °C and stirred for 18 hours. After the reaction was complete, the solution was cooled to room temperature and filtered with Celite. The solution was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate : hexane = 25:75) to give the iridium precursor M4 (8.36 g, yield: 52%). (2) Synthesis of compound 230

[0176] The iridium precursor M4 (2.77 g, 1.5 mmol) and compound L1 (0.47 g, 3 mmol), dissolved in toluene (100 mL), were placed in a 250 mL round-bottom flask under a nitrogen atmosphere. The solution was then heated under reflux with stirring for 24 hours. After the reaction was complete, the solution was cooled to room temperature. The organic layer was then extracted with dichloromethane and distilled water, and the water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: toluene:hexane = 1:1) to give compound 230 (1.35 g, yield: 86%). Synthesis example 14: Synthesis of compound 232

[0177] The iridium precursor M4 (2.77 g, 1.5 mmol) and compound L2 (0.30 g, 3 mmol), dissolved in a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL), were placed in a 150 mL round-bottom flask under a nitrogen atmosphere, and the solution was stirred at 135 °C for 24 hours. After the reaction was complete, the solution was cooled to room temperature, and the organic layer was extracted with dichloromethane and distilled water. The water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: toluene:hexane = 1:3) to give compound 232 (1.30 g, yield: 88%). Synthesis Example 15: Synthesis of Compound 234(1) Synthesis of the Iridium Precursor M5

[0178] Iridium(III) trichloride hydrate (2.60 g, 8.7 mmol) and intermediate E (20.83 g, 34.9 mmol), dissolved in 2-(2-methoxyethoxy)ethanol (300 mL), were placed in a 500 mL round-bottom flask under a nitrogen atmosphere. The solution was heated to 185 °C and stirred for 18 hours. After the reaction was complete, the solution was cooled to room temperature and filtered with Celite. The solution was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate : hexane = 25:75) to give the iridium precursor M5 (8.91 g, yield: 53%). (2) Synthesis of compound 234

[0179] The iridium precursor M5 (2.86 g, 1.5 mmol) and compound L1 (0.47 g, 3 mmol), dissolved in toluene (100 mL), were placed in a 250 mL round-bottom flask under a nitrogen atmosphere. The solution was then heated under reflux with stirring for 24 hours. After the reaction was complete, the solution was cooled to room temperature. The organic layer was then extracted with dichloromethane and distilled water, and the water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: toluene:hexane = 1:1) to give compound 234 (1.37 g, yield: 85%). Synthesis example 16: Synthesis of compound 236

[0180] The iridium precursor M5 (2.86 g, 1.5 mmol) and compound L2 (0.30 g, 3 mmol), dissolved in a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL), were placed in a 150 mL round-bottom flask under a nitrogen atmosphere, and the solution was stirred at 135 °C for 24 hours. After the reaction was complete, the solution was cooled to room temperature, and the organic layer was extracted with dichloromethane and distilled water. The water in the organic layer was removed with anhydrous MgSO4. The organic layer was filtered, and the filtrate was treated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: toluene:hexane = 1:3) to give compound 236 (1.23 g, yield: 81%). Example 1: (Ex. 1): Manufacturing an OLED

[0181] An organic light-emitting diode (OLED) was synthesized using compound 5, as obtained in Synthesis Example 1, as a dopant in an emission material layer (EML). A glass substrate onto which ITO (100 nm) was deposited as a thin film was washed and ultrasonically purified with a solvent such as isopropyl alcohol or acetone, and then oven-dried at 100 °C. The substrate was transferred to a vacuum chamber for the deposition of an emission layer. Subsequently, an emission layer and a cathode were evaporated using a heating boat at approximately 5–7 °C. -7 Torr was deposited with a settling rate of 1 Å / s in the following order:

[0182] A HIL (based on HI-1 (NPNPB), 60 nm); an HTL (NPB, 80 nm); an EML (host (CBP, 95 wt%), a doping material (Compound 5, 5 wt%), 30 nm); an ETL-EIL (based on ET-1 (2-[4-(9,10-Di-2-naphthalenyl-2-anthrace-nyl)phenyl]-1-phenyl-1H-benzimidazole, ZADN, 50 wt%), Liq (50 wt%), 30 nm); and a cathode (Al, 100 nm).

[0183] A cover layer (CPL) was then deposited over the cathode, and the device was encapsulated with glass. After deposition of the emissive layer and the cathode, the OLED was transferred from the deposition chamber to a drying oven for film formation, followed by encapsulation using UV-curable epoxy and a moisture trap. The HIL material, HTL material, host in the EML, and ETL material are shown below: Examples 2-10 (Ex. 2-10): Manufacturing of OLEDs

[0184] An OLED was fabricated using the same procedure and material as in Example 1, except for compound 6 (Ex. 2), compound 50 (Ex. 3), compound 51 (Ex. 4), compound 65 (Ex. 5), compound 66 (Ex. 6), compound 95 (Ex. 7), compound 96 (Ex. 8), compound 110 (Ex. 9) or compound 111 (Ex. 10) as doping material in the EML instead of compound 1. Comparative example 1-7 (Ref. 1-8): Manufacturing of OLEDs

[0185] An OLED was fabricated using the same procedure and material as in Example 1, except for the following Ref-1 (Ref. 1), Ref-2 (Ref. 2), Ref-3 (Ref. 3), Ref-4 (Ref. 4), Ref-5 (Ref. 5), Ref-6 (Ref. 6), Ref-7 (Ref. 7) and Ref-8 (Ref. 8) as doping material in the EML instead of compound 5. Experiment 1: Measuring the luminous properties of OLEDs

[0186] Each of the OLEDs with 9 mm 2The emission area fabricated in Examples 1 to 10 and Comparison Examples 1 to 8 was connected to an external power source, and then the luminescence characteristics of all OLEDs were evaluated using a constant current source (KEITHLEY) and a PR650 photometer at room temperature (25 °C). Specifically, the drive voltage (V) and the maximum external quantum efficiency (EQE) were determined. max , relative value), the external quantum efficiency (EQE, relative value) and the time duration (LT) 95 , relative value), in which the luminance was reduced to 95% of the initial luminance, at a current density of 10 mA / cm² 2 measured. The measurement results are given in Table 1 below. Table 1: Lighting properties of OLEDs Probe Dotierungsmaterial Spannung(V) EQE max (%, relative) EQE(%, relativ) LT 95 (%, relative) Ref. 1 Ref-1 4,25 100 100 100 Ref. 2 Ref-2 4,26 112 114 115 Ref. 3 Ref-3 4,42 105 103 98 Ref. 4 Ref-4 4,49 106 108 91 Ref. 5 Ref-5 4,44 109 108 91 Ref. 6 Ref-6 4,45 101 100 97 Ref. 7 Ref- 7 4,54 108 101 95 Ref. 8 Ref-8 4,48 110 107 86 Bsp. 1 5 4,25 126 120 132 Bsp. 2 6 4,23 128 123 134 Bsp. 3 50 4,22 131 126 128 Bsp. 4 51 4,24 135 130 132 Bsp. 5 65 4,21 134 128 127 Bsp. 6 66 4,25 136 129 130 Bsp. 7 95 4,22 132 126 125 Bsp. 8 96 4,21 134 128 128 Bsp. 9 110 4,23 133 126 124 Bsp. 10 111 4,30 135 129 126

[0187] As shown in Table 1, compared to the OLEDs produced in the comparison examples, the OLEDs produced according to the examples of the invention, which were manufactured by incorporating the organic metal compound according to the present invention into the EML as a doping material, showed an identical or slightly reduced drive voltage and improved their EQE. max EQE and LT 95 significant. Examples 11-16 (Ex. 11-16): Manufacturing of OLEDs

[0188] An OLED was fabricated using the same procedure and material as in Example 1, except for compound 226 (Ex. 11), compound 228 (Ex. 12), compound 230 (Ex. 13), compound 232 (Ex. 14), compound 234 (Ex. 15) or compound 236 (Ex. 16), as the doping material in the EML instead of compound 5. Comparative example 9-13 (Ref. 9-13): Production of OLEDs

[0189] An OLED was fabricated using the same procedure and material as in Example 1, except for the following Ref-9 (Ref. 9), Ref-10 (Ref. 9), Ref-11 (Ref. 11), Ref-12 (Ref. 12) and Ref-13 (Ref. 13) as doping material in the EML instead of compound 5. Experiment 2: Measuring the luminous properties of OLEDs

[0190] The luminous properties of each of the OLEDs produced in Examples 11 to 16 and Comparison Examples 9 to 13 were measured using the same procedure as Experiment 1. The measurement results are given in Table 2 below. Table 2: Lighting properties of OLEDs Probe Dotierungsmaterial Spannung(V) EQE max (%, relative) EQE(%, relativ) LT 95 (%, relative) Ref. 9 Ref-9 4,25 100 100 100 Ref. 10 Ref-10 4,25 105 103 112 Ref. 11 Ref-11 4,54 108 107 80 Ref. 12 Ref-12 4,55 103 100 84 Ref. 13 Ref-13 4,55 104 105 79 Bsp. 11 226 4,25 120 115 128 Bsp. 12 228 4,21 122 118 132 Bsp. 13 230 4,24 125 121 125 Bsp. 14 232 4,23 127 123 128 Bsp. 15 234 4,26 126 120 132 Bsp. 16 236 4,22 129 125 124

[0191] As shown in Table 2, compared to the OLED produced in the comparison examples, the OLEDs of the invention examples produced by incorporating the organic metal compound according to the present invention into the EML as a doping material showed an identical or slightly reduced drive voltage and improved their EQE. max EQE and LT 95 significant.

[0192] Taking into account the results in Tables 1 and 2, it is possible to realize an OLED with lower drive voltage as well as excellent luminous efficiency and luminous lifetime by introducing the organic metal compound into an emission layer.

Claims

[1] Organic metal compound with the following structure of formula 1: Ir(L A ) m (L B ) n [Formula 1] where L A which has the following structure of Formula 2; L B an auxiliary ligand with the following structure of formula 4 is; where m is an integer from 1 to 3 and n is an integer from 0 to 2, where m + n equals 3; where R1 is unsubstituted or substituted C1-C 20 -Alkyl, an unsubstituted alicyclic C4-C 30 -group or an unsubstituted or substituted aromatic C6-C 30 -group and R2 and R3 are independently hydrogen or deuterium, or R1 is defined above and R2 and R3 are unsubstituted aromatic C6-C 20 -form a ring; and A has the following structure of formula 3: where each of X1 to X4 is independent CR4; X5 to X7 is independent of CR5; X8 to X 11 independent CR6 is; Each R4 to R6 independently contains hydrogen, deuterium, or unsubstituted C1-C 20 -Alkyl is; wherein an imidazole ligand in formula 2 is bonded to a carbon atom forming CR4 from X1 to X4, and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom bonded by the imidazole ligand from X1 to X4, or an imidazole ligand in formula 2 is bonded to a carbon atom forming CR5 from X5 to X7, and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom is bound, which is bound by the imidazole ligand from X5 to X7; [2] Organic metal compound according to claim 1, wherein L A Formula 5 has the following structure: where each is from R1 to R3 and X1 to X 11 as defined for Formula 2 and Formula 3. [3] Organic metal compound according to claim 1, wherein L A exhibits any of the following structures of Formula 6A to Formula 6F: where each of a, b and c is a number of a substituent. each from R1 to R3 as defined for formula 2; each of R 11 to R 13 independent of hydrogen, deuterium or unsubstituted C1-C 20 -Alkyl is. [4] Organic metal compound according to claim 1, wherein L A Formula 7 has the following structure: where each is from R1 to R3 and X1 to X 11 as defined for Formula 2 and Formula 3. [5] Organic metal compound according to claim 1, wherein L A Formula 8A or 8B has the following structure: where each of d, e and f is a number of a substituent. each from R1 to R3 as defined for formula 2; each of R 11 to R 13independently of each other hydrogen, deuterium or unsubstituted C1-C 20 -Alkyl is. [6] Organic metal compound according to any one of the preceding claims, wherein the auxiliary ligand L B Formula 9A or Formula 9B has the following structure: where each of R 21 , R 22 and R 31 to R 33 independent hydrogen, deuterium, unsubstituted or substituted C1-C 20 -Alkyl, unsubstituted or substituted C1-C 20 -Heteroalkyl, unsubstituted or substituted C2-C 20 -Alkenyl, unsubstituted or substituted C2-C 20 -Heteroalkenyl, unsubstituted or substituted C1-C 20 -Alkoxy, Amino, a carboxyl group, nitrile, isonitrile, sulfanyl, phosphine, unsubstituted or substituted C1-C 20 -Alkylamino, unsubstituted or substituted C1-C 20-Alkylsilyl, an unsubstituted or substituted alicyclic C4-C 30 -group, an unsubstituted or substituted heteroalicyclic C3-C 30 -group, an unsubstituted or substituted aromatic C6-C 30 -group or an unsubstituted or substituted heteroaromatic C3-C 30 -group is, or if each of j and k is 2 or more, each of adjacent two of R 31 to R 33 , adjacent two of R 21 and adjacent two of R 23 independently of an unsubstituted or substituted alicyclic C4-C 20 -ring, an unsubstituted or substituted heteroalicyclic C3-C 20 -ring, an unsubstituted or substituted aromatic C6-C 30 -ring or an unsubstituted or substituted heteroaromatic C3-C 30 - forms a ring. [7] Organic metal compound according to claim 1, wherein the organic metal compound is selected from the following compounds of formula 10: [8] Organic metal compound according to claim 1, wherein the organic metal compound is selected from the following compounds of formula 11: [9] Organic light-emitting diode, which includes: a first electrode; a second electrode facing the first electrode; and an emission layer arranged between the first and second electrodes and comprising at least one emission material layer, wherein the at least one emission material layer comprises the organic metal compound according to one of the preceding claims. [10] Organic light-emitting diode according to claim 9, wherein the at least one emission material layer comprises a host and a doping material and wherein the doping material comprises the organic metal compound. [11] Organic light-emitting diode according to claim 9, wherein the emission layer comprises a first emission part arranged between the first and the second electrode, and a second emission part arranged between the first emission part and the second electrode, and a first charge generation layer arranged between the first and the second emission part, wherein the first emission part comprises a first emission material layer and the second emission part comprises a second emission material layer, and wherein the first and / or the second emission material layer comprises the organic metal compound. [12] Organic light emission device comprising: a substrate; and the organic light-emitting diode according to any one of claims 9 to 11.

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