Organometallic compound, organic light-emitting diode having same, and organic light-emitting device

Abstract

The present disclosure relates to an organometallic compound having a structure of the following Chemical Formula 1, an organic light emitting diode (OLED) comprising the organometallic compound, and an organic light emitting device. An OLED and an organic light-emitting device including the organometallic compound may improve their luminous efficiency, emission color purity, and lifespan. [Chemical Formula 1] # imgabs0 #

Description

[0001] This application is a divisional application. The application number of the original application is "202111228407.6", the application date is October 21, 2021, and the name of the invention is "Organometallic compounds, organic light-emitting diodes and organic light-emitting devices having the same".

[0002] CROSS-REFERENCE TO RELATED APPLICATIONS

[0003] This application claims the benefit of priority to Korean Patent Application No. 10-2020-0138457 filed in Korea on October 23, 2020, the entire contents of which are expressly incorporated into this application. Technical Field

[0004] The present disclosure relates to an organic metal compound, and more particularly, to an organic metal compound having excellent luminous efficiency and luminous lifetime, and an organic light emitting diode and an organic light emitting device including the organic metal compound. Background Art

[0005] Among the widely used flat panel display devices, organic light emitting diode (OLED) display devices have attracted much attention as display devices that are rapidly replacing liquid crystal display devices (LCD). OLED can be formed into a thickness of less than Organic thin films can realize unidirectional or bidirectional images through electrode configuration. In addition, OLEDs can even be formed on flexible transparent substrates such as plastic substrates, so that flexible or foldable display devices can be easily realized using OLEDs. In addition, OLEDs can be driven at a lower voltage, and compared with LCDs, OLEDs have excellent high color purity.

[0006] Since fluorescent materials only use singlet exciton energy during the luminescence process, the fluorescent materials of the related art show low luminescence efficiency. On the contrary, since phosphorescent materials use triplet exciton energy and singlet exciton energy during the luminescence process, phosphorescent materials can show high luminescence efficiency. However, as metal complexes of representative phosphorescent materials, they have short luminescence life for commercial use. Therefore, it is still necessary to develop a new compound that can improve luminescence efficiency and luminescence life. Summary of the invention

[0007] Technical issues

[0008] Accordingly, embodiments of the present disclosure are directed to an organic light emitting device that substantially obviates one or more problems due to limitations and disadvantages of the related art.

[0009] One aspect of the present disclosure is to provide an organic metal compound having excellent luminous efficiency and luminous lifetime, and an organic light emitting diode and an organic light emitting device including the compound.

[0010] Additional features and aspects will be set forth in the following description, and will become apparent in part through the description, or may be learned through the practice of the inventive concepts provided herein. Other features and aspects of the inventive concepts may be realized and obtained through the structures specifically pointed out in the written description or their derivative structures, as well as the claims and the accompanying drawings.

[0011] Technical Solution

[0012] To achieve these and other aspects of the inventive concept as embodied and broadly described, in one aspect, the present disclosure provides an organometallic compound having a structure of the following Chemical Formula 1:

[0013] [Chemical formula 1]

[0014]

[0015] in,

[0016] M is molybdenum (Mo), tungsten (W), rhenium (Re), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt) or silver (Ag);

[0017] A and B are each a carbon atom;

[0018] R is unsubstituted or substituted C 1 -C 20 Alkyl, unsubstituted or substituted C 1 -C 20 Alkylsilyl, unsubstituted or substituted C 4 -C 30 Alicyclic, unsubstituted or substituted C 3 -C 30 Heteroalicyclic, unsubstituted or substituted C 6 -C 30 Aryl, or unsubstituted or substituted C 3 -C 30 Heteroaryl; X 1 To X 11 are independently a carbon atom, CR 1 or N;

[0019] With X 3 -X 5 , Y 1 and A ring (a); or having X 8 -X 11 , Y 2 and only one of the rings (b) of B is formed;

[0020] If a ring (a) is formed, then

[0021] X 3 and Y 1 Each is a carbon atom,

[0022] X 6 With X 7 or X 7 With X 8 Forming unsubstituted or substituted C 4 -C 30 Alicyclic, unsubstituted or substituted C 3 -C 30 Heteroalicyclic, unsubstituted or substituted C 6 -C 30 Aromatic ring, or unsubstituted or substituted C 3 -C 30 heteroaromatic ring;

[0023] Y 2 Yes BR 2 , CR 2 R 3 、C=O、SiR 2 R 3 ,GeR 2 R 3 , PR 2 、P=O、O、S、SO 2 ,

[0024] Se, SeO 2 , Te or TeO 2 , or NR a , where R a is unsubstituted or substituted C 1 -C 20 Alkyl, or unsubstituted or substituted C 6 -C 30 Aryl;

[0025] If a ring (b) is formed, then

[0026] X 8 and Y 2 Each is a carbon atom,

[0027] X 1 With X 2 or X 2 With X 3 Forming unsubstituted or substituted C 4 -C 30 Alicyclic, unsubstituted or substituted C 3 -C 30 Heteroalicyclic, unsubstituted or substituted C 6 -C 30 Aromatic ring, or unsubstituted or substituted C 3 -C 30heteroaromatic ring;

[0028] Y 1 Yes BR 2 , CR 2 R 3 、C=O、SiR 2 R 3 ,GeR 2 R 3 , PR 2 、P=O、O、S、SO 2 , Se, SeO 2 , Te or TeO 2 , or NR a , where R a is unsubstituted or substituted C 1 -C 20 Alkyl, or unsubstituted or substituted C 6 -C 30 Aryl,

[0029] R 1 To R 3 are each independently protium, deuterium, tritium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amidine group, a hydrazine group, a hydrazone group, an unsubstituted or substituted C 1 -C 20 Alkyl, unsubstituted or substituted C 2 -C 20 Alkenyl, unsubstituted or substituted C 2 -C 20 Alkynyl, unsubstituted or substituted C 1 -C 20 Alkoxy, amino, unsubstituted or substituted C 1 -C 20 Alkylamino, unsubstituted or substituted C 1 -C 20 Alkylsilyl, carboxyl, nitrile, isonitrile, sulfanyl, phosphino, unsubstituted or substituted C 4 -C 30 Alicyclic, unsubstituted or substituted C 3 -C 30 Heteroalicyclic, unsubstituted or substituted C 6 -C 30 Aryl, or unsubstituted or substituted C 3 -C 30 Heteroaryl,

[0030] Optionally,

[0031] With R 1 Two adjacent carbons connected, and / or

[0032] R 2 With R 3

[0033] Forming unsubstituted or substituted C 4 -C 30 Alicyclic, unsubstituted or substituted C 3 -C 30 Heteroalicyclic, unsubstituted or substituted C 6 -C 30 Aromatic ring, or unsubstituted or substituted C 3 -C 30 heteroaromatic ring;

[0034] It is an auxiliary ligand;

[0035] m is an integer from 1 to 3,

[0036] n is an integer from 0 to 2,

[0037] m+n is the oxidation number of M.

[0038] In another aspect, the present disclosure provides an organic light emitting diode, comprising: a first electrode; a second electrode facing the first electrode; and a light emitting layer disposed between the first electrode and the second electrode and comprising at least one light emitting material layer, wherein the at least one light emitting material layer contains the organic metal compound.

[0039] As an example, the organic metal compound may be included as a dopant in the at least one light emitting material layer.

[0040] The light emitting layer may have a single light emitting portion or a plurality of light emitting portions to form a tandem structure.

[0041] In yet another aspect, the present disclosure provides an organic light emitting device, for example, an organic light emitting display device or an organic light emitting lighting device, including a substrate and an organic light emitting diode over the substrate.

[0042] It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are intended to provide further explanation of the inventive concepts as claimed. BRIEF DESCRIPTION OF THE DRAWINGS

[0043] The present disclosure includes accompanying drawings to provide a further understanding of the present disclosure and are incorporated in and constitute a part of this application. The accompanying drawings illustrate embodiments of the present disclosure and together with the description serve to explain the principle of the present disclosure.

[0044] Figure 1 is a schematic circuit diagram showing an organic light emitting display device according to the present disclosure;

[0045] Figure 2is a cross-sectional view showing an organic light emitting display device as one example of an organic light emitting device according to an exemplary aspect of the present disclosure;

[0046] Figure 3 is a cross-sectional view showing an organic light emitting diode having a single light emitting portion according to an exemplary aspect of the present disclosure;

[0047] Figure 4 is a cross-sectional view showing an organic light emitting display device according to another exemplary aspect of the present disclosure;

[0048] Figure 5 is a cross-sectional view showing an organic light emitting diode having a double-layer stack structure according to still another exemplary aspect of the present disclosure;

[0049] Figure 6 is a cross-sectional view showing an organic light emitting diode having a three-layer stacked structure according to still another exemplary aspect of the present disclosure;

[0050] Figure 7 is a graph showing the photoluminescence (PL) intensity of an organometallic compound synthesized in one example of the present disclosure. DETAILED DESCRIPTION

[0051] Reference will now be made in detail to aspects of the present disclosure, examples of which are illustrated in the accompanying drawings.

[0052] [Organometallic compounds]

[0053] The phosphorescent materials of the prior art exhibit low color purity and low quantum efficiency due to having a wide photoluminescence spectrum when emitting light. The organometallic compound disclosed herein has a rigid chemical conformation, so that it can improve the luminescence efficiency and luminescence lifetime. The organometallic compound disclosed herein may have the structure of the following chemical formula 1:

[0054] [Chemical formula 1]

[0055]

[0056] in,

[0057] M is molybdenum (Mo), tungsten (W), rhenium (Re), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt) or silver (Ag);

[0058] A and B are each a carbon atom;

[0059] R is unsubstituted or substituted C 1 -C 20 Alkyl, unsubstituted or substituted C 1 -C 20 Alkylsilyl, unsubstituted or substituted C4 -C 30 Alicyclic, unsubstituted or substituted C 3 -C 30 Heteroalicyclic, unsubstituted or substituted C 6 -C 30 Aryl, or unsubstituted or substituted C 3 -C 30 heteroaryl;

[0060] X 1 To X 11 are independently a carbon atom, CR 1 or N;

[0061] With X 3 -X 5 , Y 1 and A ring (a); or having X 8 -X 11 , Y 2 and only one of the rings (b) of B is formed;

[0062] If a ring (a) is formed, then

[0063] X 3 and Y 1 Each is a carbon atom,

[0064] X 6 With X 7 or X 7 With X 8 Forming unsubstituted or substituted C 4 -C 30 Alicyclic, unsubstituted or substituted C 3 -C 30 Heteroalicyclic, unsubstituted or substituted C 6 -C 30 Aromatic ring, or unsubstituted or substituted C 3 -C 30 heteroaromatic ring;

[0065] Y 2 Yes BR 2 , CR 2 R 3 、C=O、SiR 2 R 3 ,GeR 2 R 3 , PR 2 、P=O、O、S、SO 2 ,

[0066] Se, SeO 2 , Te or TeO 2 , or NR a, where R a is unsubstituted or substituted C 1 -C 20 Alkyl, or unsubstituted or substituted C 6 -C 30 Aryl;

[0067] If a ring (b) is formed, then

[0068] X 8 and Y 2 Each is a carbon atom,

[0069] X 1 With X 2 or X 2 With X 3 Forming unsubstituted or substituted C 4 -C 30 Alicyclic, unsubstituted or substituted C 3 -C 30 Heteroalicyclic, unsubstituted or substituted C 6 -C 30 Aromatic ring, or unsubstituted or substituted C 3 -C 30 heteroaromatic ring;

[0070] Y 1 Yes BR 2 , CR 2 R 3 、C=O、SiR 2 R 3 ,GeR 2 R 3 , PR 2 、P=O、O、S、SO 2 , Se, SeO 2 , Te or TeO 2 , or NR a , where R a is unsubstituted or substituted C 1 -C 20 Alkyl, or unsubstituted or substituted C 6 -C 30 Aryl,

[0071] R 1 To R 3 are each independently protium, deuterium, tritium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amidine group, a hydrazine group, a hydrazone group, an unsubstituted or substituted C 1 -C 20 Alkyl, unsubstituted or substituted C 2 -C 20 Alkenyl, unsubstituted or substituted C 2 -C 20Alkynyl, unsubstituted or substituted C 1 -C 20 Alkoxy, amino, unsubstituted or substituted C 1 -C 20 Alkylamino, unsubstituted or substituted C 1 -C 20 Alkylsilyl, carboxyl, nitrile, isonitrile, sulfanyl, phosphino, unsubstituted or substituted C 4 -C 30 Alicyclic, unsubstituted or substituted C 3 -C 30 Heteroalicyclic, unsubstituted or substituted C 6 -C 30 Aryl, or unsubstituted or substituted C 3 -C 30 Heteroaryl,

[0072] Optionally,

[0073] With R 1 Two adjacent carbons connected, and / or

[0074] R 2 With R 3

[0075] Forming unsubstituted or substituted C 4 -C 30 Alicyclic, unsubstituted or substituted C 3 -C 30 Heteroalicyclic, unsubstituted or substituted C 6 -C 30 Aromatic ring, or unsubstituted or substituted C 3 -C 30 heteroaromatic ring;

[0076] It is an auxiliary ligand;

[0077] m is an integer from 1 to 3;

[0078] n is an integer from 0 to 2;

[0079] m+n is the oxidation number of M.

[0080] As used herein, the term "unsubstituted" means that the particular group has no substituents and is attached to hydrogen. In this case, hydrogen includes protium, deuterium, and tritium.

[0081] As used herein, the term "substituted" includes unsubstituted or halogen-substituted C 1 -C 20 Alkyl, unsubstituted or halogen-substituted C 1 -C 20Alkoxy, halogen, cyano, -CF 3 , hydroxyl, carboxyl, carbonyl, amino, C 1 -C 10 Alkylamino, C 6 -C 30 Arylamino, C 3 -C 30 Heteroarylamino, C 6 -C 30 Aryl, C 3 -C 30 Heteroaryl, nitro, hydrazide, sulfonate, C 1 -C 20 Alkylsilyl, C 6 -C 30 Arylsilyl and C 3 -C 30 Heteroarylsilyl, but not limited thereto.

[0082] As used herein, the term "alkyl" refers to a branched or unbranched saturated hydrocarbon group of 1 to 20 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, and the like.

[0083] As used herein, the term "alkenyl" is a hydrocarbon group of 2 to 20 carbon atoms containing at least one carbon-carbon double bond. The alkenyl group may be substituted with one or more substituents.

[0084] As used herein, the term "alicyclic" or "cycloalkyl" refers to a non-aromatic carbon ring consisting of at least three carbon atoms. Examples of alicyclic groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, etc., but are not limited thereto. The alicyclic group may be substituted by one or more substituents.

[0085] As used herein, the term "alkoxy" refers to a branched or unbranched alkyl group bonded by an ether bond represented by the formula -O(-alkyl), wherein alkyl is as defined herein. Examples of alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, and tert-butoxy, etc.

[0086] As used herein, the term "alkylamino" refers to an amino group of the formula -NH(-alkyl) or -N(-alkyl) 2The group represented by the formula -NH(-alkyl) is as defined herein. Examples of alkylamino groups represented by the formula -NH(-alkyl) include methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, (sec-butyl)amino, (tert-butyl)amino, pentylamino, isopentylamino, (tert-pentyl)amino, hexylamino, etc., but are not limited thereto. 2 Examples of the alkylamino group represented include dimethylamino, diethylamino, dipropylamino, diisopropylamino, dibutylamino, diisobutylamino, di(sec-butyl)amino, di(tert-butyl)amino, dipentylamino, diisopentylamino, di(tert-pentyl)amino, dihexylamino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-ethyl-N-propylamino and the like, but are not limited thereto.

[0087] As used herein, the term "aromatic" or "aryl" is well known in the art. The term includes covalently linked monocyclic or condensed ring polycyclic groups. Aromatic groups can be unsubstituted or substituted. Examples of aromatic or aryl groups include phenyl, 1-naphthyl, 2-naphthyl, 4-biphenyl, anthracenyl and phenanthrenyl, etc. The substituents in each of the above aromatic ring systems are acceptable substituents defined herein.

[0088] As used herein, the term "alkylsilyl" refers to any linear or branched, saturated or unsaturated acyclic or cyclic alkyl group having 1 to 20 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, trimethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and phenylsilyl.

[0089] As used herein, the term "halogen" refers to a fluorine, chlorine, bromine or iodine atom.

[0090] As used herein, the term "hetero" in terms such as "hetero aromatic ring", "hetero cyclo alkylene group", "hetero arylene group", "hetero aryl alkylene group", "hetero aryl oxylene group", "hetero cyclo alkyl group", "hetero aryl group", "heteroaryl alkyl group", "hetero aryloxyl group" and "hetero arylamino group" refers to at least one carbon atom constituting an aromatic ring or an alicyclic ring, for example, 1 to 5 carbon atoms are substituted by at least one heteroatom selected from N, O, S, P and a combination thereof.

[0091] As used herein, the term "heteroaromatic" or "heteroaryl" refers to a heterocycle containing heteroatoms selected from N, O and S in the ring, wherein the ring system is an aromatic ring. The term includes covalently linked monocyclic or fused polycyclic groups. The heteroaromatic group can be unsubstituted or substituted. Examples of heteroaromatic or heteroaryl groups include pyridyl, pyrrolyl, pyrazinyl, pyrimidinyl, thienyl (or phenylthio), thiazolyl, furanyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, oxadiazolyl, thiazolyl and thiadiazolyl.

[0092] As used herein, the term "heteroaryloxy" refers to a group represented by the formula -O-(heteroaryl), wherein heteroaryl is as defined herein.

[0093] For example, when R and R in Formula 1 1 To R 3 Each is independently C 6 -C 30 When the group is aromatic, R, R 1 to R3 can each independently be C 6 -C 30 Aryl, C 7 -C 30 Arylalkyl, C 6 -C 30 Aryloxy and C 6 -C 30 As an example, when R, R 1 To R 3 Each is independently C 6 -C30 When the group is aromatic, R, R 1 To R 3 The phenyl group may be independently phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pentalenyl, indenyl, indenoindenyl, heptalenyl, biphenylenyl, indacenyl, phenalenyl, phenanthrenyl, triphenylenyl, diphenylphenanthrenyl, azulenyl, pyrenyl, fluoranthenyl, triphenylene, The present invention also includes non-condensed or condensed aromatic groups such as phenyl, tetraphenylene, tetracenyl, pleiadenyl, picenyl, pentaphenylenyl, pentacenyl, fluorenyl, indenofluorenyl and spirofluorenyl, but is not limited thereto.

[0094] Alternatively, when R, R in Formula 1 1 To R 3 Each independently is C 3 -C 30 In the case of heteroaryl, R, R 1 To R 3 Can be C independently 3 -C 30 Heteroaryl, C 4 -C 30 Heteroarylalkyl, C 3 -C 30 Heteroaryloxy and C 3 -C 30 As an example, when R, R 1 To R 3 Each independently is C 3 -C 30 In the case of heteroaryl, R, R 1 To R 3The heteroaryl radicals may be independently non-fused or fused, such as pyrrolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, imidazolyl, pyrazolyl, indolyl, isoindolyl, indazolyl, indolizinyl, pyrrolizinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolecarbazolyl, indenocarbazolyl, benzofurancarbazolyl, benzothiophenecarbazolyl, carbolyl, quinolyl, isoquinolyl, phthalazinyl, quinoxalinyl, cinnozinyl, quinazolinyl, quinolizinyl, purinyl, benzoquinolyl, benzoisoquinolyl, benzoquinazolinyl, benzoquinoxalinyl, acridinyl, phenazinyl, phen oxazinyl, phenothiazinyl, phenanthrolinyl, furidinyl, phenanthridinyl, pteridinyl, naphthyridinyl, furanyl, pyranyl, oxazinyl, oxazolyl, oxadiazolyl, triazolyl, dioxinyl, benzofuranyl, dibenzofuranyl, thiopyranyl, anthranyl, benzopyranyl, isobenzopyranyl, thiazinyl, thienyl, benzothienyl, dibenzothienyl, difuranpyrazinyl, benzofurandibenzofuranyl, benzothiophenebenzothienyl, benzothiophenedibenzothienyl, benzothiophenebenzofuranyl, benzothiophenedibenzofuranyl, xanthene-bound spiroacridinyl, benzothiophene ... 1 -C 10 Alkyl-substituted acridinyl and N-substituted spirofluorenyl, but are not limited thereto.

[0095] As an example, R, R 1 To R 3 The aryl or heteroaryl groups may each be composed of one to three aromatic or heteroaromatic rings. 1 To R 3 When the number of aromatic or heteroaromatic rings is greater than three, the conjugated structure in the entire molecule becomes too long, and thus the organometallic compound has too narrow an energy band gap. 1 To R 3 The aryl or heteroaryl groups may each independently include phenyl, biphenyl, naphthyl, anthracenyl, pyrrolyl, triazine, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, carbazolyl, acridinyl, carbolyl, phenazine, phenoxazine and / or phenothiazine, but are not limited thereto.

[0096] Or, with R 1 The two adjacent carbons and / or R 2 With R 3 Can form unsubstituted or substituted C 4 -C 30 Alicyclic (e.g., C 5 -C 10 Alicyclic), unsubstituted or substituted C 3 -C 30 Heteroalicyclic (e.g., C3 -C 10 Heteroalicyclic), unsubstituted or substituted C 6 -C 30 Aromatic rings (e.g., C 6 -C 20 aromatic ring), or unsubstituted or substituted C 3 -C 30 Heteroaromatic rings (e.g., C 3 -C 20 The alicyclic ring, heteroalicyclic ring, aromatic ring and heteroaromatic ring are: 1 Two adjacent carbon atoms connected; or R 2 With R 3 For example, the aromatic ring or heteroaromatic ring formed by these groups may include unsubstituted or substituted with at least one C 1 -C 10 Alkyl-substituted benzene ring, pyridine ring, indole ring, pyran ring, fluorene ring, but not limited thereto.

[0097] The organometallic compound having the structure of Chemical Formula 1 has a ligand fused with a plurality of aromatic rings and / or heteroaromatic rings, and therefore has a narrow full width at half maximum (FWHM) in the photoluminescence spectrum. Specifically, since the organometallic compound has a rigid chemical conformation, its conformation does not rotate during the luminescence process, thereby maintaining a good luminescence lifetime. The organometallic compound has a specific photoluminescence radiation range, and therefore, its color purity can be improved.

[0098] In addition, the organometallic compound can be a heteropolymetallic complex comprising two different bidentate ligands coordinated to a central metal atom. By combining two different bidentate ligands, the photoluminescence color purity and luminescent color of the organometallic compound can be easily controlled. In addition, the color purity and luminescent peak of the organometallic compound can be controlled by introducing various substituents into each ligand. For example, the organometallic compound having the structure of Chemical Formula 1 can emit yellow to red, and can improve the luminous efficiency of an organic light emitting diode.

[0099] In one exemplary aspect, as an example of an organic metal compound having a structure of Chemical Formula 1, the organic metal compound may have an organic metal compound having X 3 -X 5 , Y 1 and the ring (a) of A. This organometallic compound may have the structure of the following Chemical Formula 2:

[0100] [Chemical formula 2]

[0101]

[0102] Among them, M, R, m and n are each the same as defined in Chemical Formula 1; X 21 To X 27 Each is independently CR 1 or N; Y 3 Yes BR 2 , CH 2 , CR 2 R 3 、C=O、SiR 2 R 3 ,GeR 2 R 3 , pR 2 、P=O、O、S、SO 2 , Se, SeO 2 , Te or TeO 2 ; R 1 To R 3 Each is the same as defined in Chemical Formula 1.

[0103] In an alternative aspect, as an example of an organometallic compound having a structure of Chemical Formula 1, the organometallic compound may have 8 -X 11 , Y 2 and a ring (b) of B. This organometallic compound may have the structure of the following Chemical Formula 3:

[0104] [Chemical formula 3]

[0105]

[0106] Among them, M, m and n are each the same as defined in Chemical Formula 1; X 31 To X 38 Each is independently CR 1 or N; Y 4 Yes BR 2 , CH 2 , CR 2 R 3 、C=O、SiR 2 R 3 ,GeR 2 R 3 , PR 2 、P=O、O、S、SO 2 , Se, SeO 2 , Te or TeO 2 ; R 1 To R 3 Each is the same as defined in Chemical Formula 1.

[0107] More specifically, in the organic metal compound having the structure of Chemical Formula 2, the 25 and X 26 The organometallic compound of the aromatic ring or heteroaromatic ring formed may have the structure of the following Chemical Formula 4, and in the organometallic compound having the structure of Chemical Formula 2, the compound containing X 26 and X 27 The formed aromatic ring or heteroaromatic ring organic metal compound may have the structure of the following Chemical Formula 5:

[0108] [Chemical formula 4]

[0109]

[0110] [Chemical formula 5]

[0111]

[0112] Among them, M, R, m, n, X 21 To X 24 and Y 3 Each is the same as defined in Chemical Formula 2; X 41 To X 45 Each is independently CR 1 or N; R 1 To R 3 Each is the same as defined in Chemical Formula 1.

[0113] Alternatively, in the organic metal compound having the structure of Chemical Formula 3, the organic metal compound comprising X 31 and X 32 The organometallic compound of the aromatic ring or heteroaromatic ring formed may have the structure of the following Chemical Formula 6, and in the organometallic compound having the structure of Chemical Formula 3, the 32 and X 33 The formed aromatic ring or heteroaromatic ring organic metal compound may have the structure of the following Chemical Formula 7:

[0114] [Chemical formula 6]

[0115]

[0116] [Chemical formula 7]

[0117]

[0118] Among them, M, m, n, X 34 To X 38 and Y 4 Each is the same as defined in Chemical Formula 3; X 51 To X55 Each is independently CR 1 or N; R 1 To R 3 Each is the same as defined in Chemical Formula 1.

[0119] Auxiliary ligand can be a bidentate ligand, where Z 1 and Z 2 Independently selected from oxygen atoms, nitrogen atoms and phosphorus atoms. The bidentate ligand may be an acetylacetonate ligand, or an N,N'- or N,O-bidentate anionic ligand.

[0120] As an example, the central coordinating metal may be iridium and the auxiliary ligands The organometallic compound may have any one of the following structures of Chemical Formula 8 to Chemical Formula 11:

[0121] [Chemical formula 8]

[0122]

[0123] [Chemical formula 9]

[0124]

[0125] [Chemical formula 10]

[0126]

[0127] [Chemical formula 11]

[0128]

[0129] Wherein, R is the same as defined in Chemical Formula 1; X 21 To X 24 , X 34 To X 38 , X 41 To X 45 and X 51 To X 55 Each is independently CR 1 or N; Y 3 and Y 4 Each is independently BR 2 , CH 2 , CR 2 R 3 、C=O、SiR 2 R 3 ,GeR 2 R 3 , PR 2 、P=O、O、S、SO 2, Se, SeO 2 , Te or TeO 2 ; R 1 To R 3 Same as defined in Chemical Formula 1; R 11 To R 13 are each independently protium, deuterium, tritium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amidine group, a hydrazine group, a hydrazone group, an unsubstituted or substituted C 1 -C 20 Alkyl, unsubstituted or substituted C 2 -C 20 Alkenyl, unsubstituted or substituted C 2 -C 20 Alkynyl, unsubstituted or substituted C 1 -C 20 Alkoxy, amino, unsubstituted or substituted C 1 -C 20 Alkylamino, unsubstituted or substituted C 1 -C 20 Alkylsilyl, carboxyl, nitrile, isonitrile, sulfanyl, phosphino, unsubstituted or substituted C 4 -C 30 Alicyclic, unsubstituted or substituted C 3 -C 30 Heteroalicyclic, unsubstituted or substituted C 6 -C 30 Aryl, or unsubstituted or substituted C 3 -C 30 Heteroaryl; m is an integer from 1 to 3, n is an integer from 0 to 2, wherein m+n is 3.

[0130] As an example, the organic metal compound having the structure of Chemical Formula 8 may include Compound 1-180 of the following Chemical Formula 12:

[0131] [Chemical formula 12]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138] The organic metal compound having the structure of Chemical Formula 9 may include compounds 181-360 of the following Chemical Formula 13:

[0139] [Chemical formula 13]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147] In addition, the organic metal compound having the structure of Chemical Formula 10 may include compounds 361-494 of the following Chemical Formula 14:

[0148] [Chemical formula 14]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] In the organometallic compound having the structure of Chemical Formula 11, wherein Y 4 The organic metal compound which is an unsubstituted or substituted carbon atom may include compounds 495-577 of the following Chemical Formula 15:

[0155] [Chemical formula 15]

[0156]

[0157]

[0158]

[0159]

[0160] Alternatively, in the organometallic compound having the structure of Chemical Formula 11, wherein Y 4The organometallic compound which is an unsubstituted or substituted heteroatom may include compounds 578-609 of the following Chemical Formula 16:

[0161] [Chemical formula 16]

[0162]

[0163]

[0164] The organometallic compound having any one of the structures of Chemical Formula 2 to Chemical Formula 12 contains a ligand composed of a plurality of fused aromatic rings or heteroaromatic rings, and therefore has a rigid chemical conformation. The organometallic compound has a narrow FWHM, and since it can maintain its stable chemical conformation during the light emission process, its color purity and light emission lifetime can be improved. In addition, since the organometallic compound is a metal complex having a bidentate ligand, the light emission color purity and light emission color can be easily controlled. Therefore, by applying at least one of the organometallic compounds having the structures of Chemical Formula 1 to Chemical Formula 16 to the light emitting layer, the organic light emitting diode has excellent light emission efficiency.

[0165] [Organic light-emitting device and organic light-emitting diode]

[0166] By applying an organic compound having any one of the structures of Chemical Formulas 1 to 16 to a light-emitting layer, for example, a light-emitting material layer of an OLED, an OLED having excellent light-emitting efficiency and improved light-emitting life can be realized. The OLED disclosed herein can be applied to an organic light-emitting device such as an organic light-emitting display device or an organic light-emitting lighting device. An organic light-emitting display device including an OLED will be described.

[0167] Figure 1 is a schematic circuit diagram showing an organic light emitting display device according to an exemplary aspect of the present disclosure. Figure 1 As shown in FIG, in the organic light emitting display device, the gate lines GL, the data lines DL, and the power lines PL cross each other to define a pixel region P. A switching thin film transistor Ts, a driving thin film transistor Td, a storage capacitor Cst, and an organic light emitting diode D are formed in the pixel region P. The pixel region P may include a red (R) pixel region, a green (G) pixel region, and a blue (B) pixel region.

[0168] The switching thin film transistor Ts is connected to the gate line GL and the data line DL, and the driving 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 driving thin film transistor Td. When the switching thin film transistor Ts is turned on by the gate signal applied to the gate line GL, the data signal applied to the data line DL is applied to the gate of the driving thin film transistor Td and one electrode of the storage capacitor Cst through the switching thin film transistor Ts.

[0169] The driving thin film transistor Td is turned on by the data signal applied to the gate, 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 driving thin film transistor Td. Then, the organic light emitting diode D emits light with a brightness proportional to the current flowing through the driving 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 of the gate in the driving thin film transistor Td is kept constant during one frame. Therefore, the organic light emitting display device can display a desired image.

[0170] Figure 2 is a schematic cross-sectional view showing an organic light-emitting display device according to an exemplary aspect of the present disclosure. Figure 2 As shown in , the organic light emitting display device 100 includes a substrate 102, a thin film transistor Tr on the substrate 102, and an organic light emitting diode D connected to the thin film transistor Tr. As an example, the substrate 102 defines a red pixel region, a green pixel region, and a blue pixel region, and the organic light emitting diode D is located in each pixel. In other words, the organic light emitting diode D that emits red light, green light, or blue light is correspondingly located in the red pixel, the green pixel, and the blue pixel.

[0171] The substrate 102 may include glass, a thin flexible material and / or a polymer plastic, but is not limited thereto. For example, the flexible material may be selected from polyimide (PI), polyethersulfone (PES), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), polycarbonate (PC), and combinations thereof, but is not limited thereto. The substrate 102 on which the thin film transistor Tr and the organic light emitting diode D are arranged forms an array substrate.

[0172] The buffer layer 106 may be disposed over the substrate 102, and the thin film transistor Tr is disposed over the buffer layer 106. The buffer layer 106 may be omitted.

[0173] The semiconductor layer 110 is disposed above the buffer layer 106. In an exemplary aspect, the semiconductor layer 110 may include an oxide semiconductor material, without limitation thereto. In this case, a light shielding pattern may be disposed below the semiconductor layer 110, and the light shielding pattern may prevent light from being incident toward the semiconductor layer 110, thereby preventing the semiconductor layer 110 from being degraded by light. Alternatively, the semiconductor layer 110 may include polycrystalline silicon. In this case, opposite edges of the semiconductor layer 110 may be doped with impurities.

[0174] The gate insulating layer 120 including an insulating material is disposed on the semiconductor layer 110. The gate insulating layer 120 may include, for example, silicon oxide (SiO x ) or silicon nitride (SiN x ) of inorganic insulating materials, but not limited thereto.

[0175] The gate 130 made of a conductive material such as metal is disposed above the gate insulating layer 120 to correspond to the center of the semiconductor layer 110. Figure 2 Although the gate insulating layer 120 is disposed over the entire area of ​​the substrate 102 , the gate insulating layer 120 may be patterned the same as the gate 130 .

[0176] An interlayer insulating layer 140 including an insulating material is disposed above the gate 130 and covers the entire surface of the substrate 102. The interlayer insulating layer 140 may include a material such as silicon oxide (SiO x ) or silicon nitride (SiN x ) or an organic insulating material such as benzocyclobutene or photoacryl.

[0177] The interlayer insulating layer 140 has a first semiconductor layer contact hole 142 and a second semiconductor layer contact hole 144 exposing both sides of the semiconductor layer 110. The first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144 are disposed at opposite sides of the gate 130 at intervals spaced apart from the gate 130. Figure 2 As shown in FIG. 1 , the first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144 are formed in the gate insulating layer 120 . Alternatively, when the gate insulating layer 120 is patterned the same as the gate 130 , the first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144 are formed only in the interlayer insulating layer 140 .

[0178] Source and drain electrodes 152 and 154 made of a conductive material such as metal are disposed on the interlayer insulating layer 140. The source and drain electrodes 152 and 154 are spaced apart from each other relative to the gate 130 and contact both sides of the semiconductor layer 110 through the first and second semiconductor layer contact holes 142 and 144, respectively.

[0179] The semiconductor layer 110 , the gate electrode 130 , the source electrode 152 , and the drain electrode 154 constitute a thin film transistor Tr serving as a driving element. Figure 2 The thin film transistor Tr in the embodiment has a coplanar structure in which the gate 130, the source 152 and the drain 154 are arranged above the semiconductor layer 110. Alternatively, the thin film transistor Tr may have an inverse staggered structure in which the gate is arranged below the semiconductor layer and the source and drain are arranged above the semiconductor layer. In this case, the semiconductor layer may include amorphous silicon.

[0180] Despite Figure 2 Although not shown in the figure, gate lines and data lines that cross each other to define the pixel area and switching elements connected to the gate lines and data lines may also be formed in the pixel area. The switching element is connected to the thin film transistor Tr as a driving element. In addition, the power line is spaced apart in parallel with the gate line or the data line, and the thin film transistor Tr may further include a storage capacitor configured to constantly maintain the voltage of the gate within one frame.

[0181] The passivation layer 160 is disposed on the source electrode 152 and the drain electrode 154 and covers the thin film transistor Tr over the entire substrate 102. The passivation layer 160 has a flat upper surface and a drain contact hole 162 exposing the drain electrode 154 of the thin film transistor Tr. Although the drain contact hole 162 is disposed on the second semiconductor layer contact hole 144, it may be spaced apart from the second semiconductor layer contact hole 144.

[0182] The organic light emitting diode D (OLED D) includes a first electrode 210 disposed on the passivation layer 160 and connected to the drain electrode 154 of the thin film transistor Tr. The organic light emitting diode D also includes a light emitting layer 230 and a second electrode 220, each of which is sequentially disposed on the first electrode 210.

[0183] The first electrode 210 is disposed in each pixel region. The first electrode 210 may be an anode and include a conductive material having a relatively high work function value. For example, the first electrode 210 may include 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), aluminum-doped zinc oxide (AZO), etc., but is not limited thereto.

[0184] In one exemplary aspect, when the organic light-emitting display device 100 is a bottom emission type, the first electrode 210 may have a single-layer structure of TCO. Alternatively, when the organic light-emitting display device 100 is a top emission type, a light-reflecting electrode or a light-reflecting layer may be disposed below the first electrode 210. For example, the light-reflecting electrode or the light-reflecting layer may include silver (Ag) or an aluminum palladium copper (APC) alloy, but is not limited thereto. In a top emission type OLED D, the first electrode 210 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0185] In addition, the bank layer 164 is disposed on the passivation layer 160 so as to cover the edge of the first electrode 210. The bank layer 164 exposes the center of the first electrode 210 corresponding to each pixel area. The bank layer 164 may be omitted.

[0186] The light emitting layer 230 is disposed on the first electrode 210. In one exemplary aspect, the light emitting layer 230 may have a light emitting material layer (EML) of a single layer structure. Alternatively, the light emitting layer 230 may have a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an EML, a hole blocking layer (HBL), an electron transport layer (ETL) and / or an electron injection layer (EIL) (see Figure 3 and Figures 5 and 6 ) of the multilayer structure. In one aspect, the light emitting layer 230 may have a single light emitting portion. Alternatively, the light emitting layer 230 may have a plurality of light emitting portions to form a series structure.

[0187] The light emitting layer 230 may include an organic metal compound having a structure of Chemical Formula 1 to Chemical Formula 16. The light emitting layer 230 including the organic metal compound enables the OLED D and the organic light emitting device 100 to significantly improve their light emitting efficiency and light emitting lifetime.

[0188] The second electrode 220 is disposed above the substrate 102 on which the light emitting layer 230 is disposed. The second electrode 220 may be disposed above the entire display area, and may include a conductive material having a relatively low work function value compared to the first electrode 210, and may be a cathode. For example, the second electrode 220 may include aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), an alloy thereof, or a combination thereof, such as an aluminum-magnesium alloy (Al-Mg), without being limited thereto. When the organic light emitting display device 100 is a top emission type, the second electrode 220 is thin so as to have a light transmission (semi-transmission) performance.

[0189] In addition, the encapsulation film 170 may be disposed over the second electrode 220 to prevent external moisture from penetrating into the OLED D. The encapsulation film 170 may have a stacked structure of a first inorganic insulating film 172, an organic insulating film 174, and a second inorganic insulating film 176, without being limited thereto. The encapsulation film 170 may be omitted.

[0190] A polarizing plate may be attached to the packaging film 170 to reduce reflection of external light. For example, the polarizing plate may be a circular polarizing plate. When the organic light-emitting display device 100 is a bottom emission type, the polarizing plate may be disposed below the substrate 102. Alternatively, when the organic light-emitting display device 100 is a top emission type, the polarizing plate may be disposed above the packaging film 170. In addition, a cover window may be attached to the packaging film 170 or the polarizing plate. In this case, the substrate 102 and the cover window may have flexible characteristics, and therefore, the organic light-emitting display device 100 may be a flexible display device.

[0191] Next, we will describe the OLED D including the organometallic compound in more detail. Figure 3 is a schematic cross-sectional view showing an organic light emitting diode having a single light emitting portion according to an exemplary embodiment of the present disclosure. Figure 3 As shown in FIG. 1 , an organic light emitting diode D1 (OLED D1) according to the present disclosure includes a first electrode 210 and a second electrode 220 facing each other, and a light emitting layer 230 disposed between the first electrode 210 and the second electrode 220. The organic light emitting display device 100 includes a red pixel region, a green pixel region, and a blue pixel region, and the OLED D1 may be disposed in the green pixel region or the red pixel region.

[0192] In one exemplary embodiment, the light emitting layer 230 includes a light emitting material layer (EML) 340 disposed between the first electrode 210 and the second electrode 220. In addition, the light emitting layer 230 may include at least one of a HTL 320 disposed between the first electrode 210 and the EML 340 and an ETL 360 disposed between the second electrode 220 and the EML 340. In addition, the light emitting layer 230 may further include at least one of a HIL 310 disposed between the first electrode 210 and the HTL 320 and an EIL 370 disposed between the second electrode 220 and the ETL 360. Alternatively, the light emitting layer 230 may further include a first exciton blocking layer, i.e., an EBL 330, disposed between the HTL 320 and the EML 340, and / or a second exciton blocking layer, i.e., an HBL 350, disposed between the EML 340 and the ETL 360.

[0193] The first electrode 210 may be an anode that provides holes into the EML 340. The first electrode 210 may include a conductive material having a relatively high work function value, for example, a transparent conductive oxide (TCO). In an exemplary embodiment, the first electrode 210 may include ITO, IZO, ITZO, SnO, ZnO, ICO, AZO, etc., but is not limited thereto.

[0194] The second electrode 220 may be a cathode that provides electrons into the EML 340. The second electrode 220 may include a conductive material having a relatively low work function value, ie, a highly reflective material, such as Al, Mg, Ca, Ag, alloys thereof, or combinations thereof, such as Al-Mg.

[0195] The HIL 310 is disposed 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. 310 may include 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-carbazolyl-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-hexaazabenzonitrile (dipyrazine [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)polystyrenesulfonate (PEDOT / PSS), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanodimethyl-p-benzoquinone (F4TCNQ), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N,N′-diphenyl-N,N′-di[4-(N,N′-diphenyl-amino)phenyl]benzidine (NPNPB), and combinations thereof, but are not limited thereto. Depending on the performance of OLED D1, HIL310 may be omitted.

[0196] The HTL 320 is disposed between the first electrode 210 and the EML 340 and adjacent to the EML 340. In one exemplary embodiment, the HTL 320 may include N, N'-diphenyl-N, N'-bis (3-methylphenyl-1, 1'-diphenyl-4, 4'-diamine (TPD), N, N'-di (1-naphthyl) -N, N'-diphenyl - (1, 1'-diphenyl) -4, 4'-diamine (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-dioctylfluorene-2, 7-diyl) -co- (4, 4'- ( The invention also includes but is not limited to 1,1-bis(4-(N,N'-di(p-tolyl)amino)phenyl)cyclohexane (TAPC), 3,5-bis(9H-carbazole-9-yl)-N,N-diphenylaniline (DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl-4-amine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine and combinations thereof, but are not limited thereto.

[0197] The EML 340 may include a host (first host) and a dopant (first dopant) in which substantial light emission occurs. As an example, the EML 340 may emit yellow to red. For example, an organic metal compound having a structure of Chemical Formula 1 to Chemical Formula 16 may be used as a dopant in the EML 340.

[0198] The ETL 360 and the EIL 370 may be sequentially stacked between the EML 340 and the second electrode 220. The ETL 360 includes a material having high electron mobility in order to stably supply electrons to the EML 340 through rapid electron transport.

[0199] In an exemplary aspect, the ETL 360 may include at least one of oxadiazole compounds, triazole compounds, phenanthroline compounds, benzoxazole compounds, benzothiazole compounds, benzimidazole compounds, triazine compounds, etc., but is not limited thereto.

[0200] As an example, ETL 360 may include tris-(8-hydroxyquinoline)aluminum (Alq 3 ), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1′-biphenyl-4-hydroxy)aluminum (BAlq), lithium quinoline (Liq), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spirocyclic PBD, 1,3,5-tri(N-phenylbenzimidazol-2-yl)benzene (TPBi), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalene-2-yl)4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl Phenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tri(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tri(3′-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3′-(N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alt-2,7-(9,9-dioctylfluorene)] (PFNBr), tris(phenylquinoxaline) (TPQ), diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), 2-[4-(9,10-di-2-naphthalen-2-yl-2-anthracen-2-yl)phenyl]-1-phenyl-1H-benzimidazole (ZADN) and combinations thereof, but are not limited thereto.

[0201] The EIL 370 is disposed between the second electrode 220 and the ETL 360, and can improve the physical properties of the second electrode 220, and thus, can improve the life span of the OLED D1. In an exemplary aspect, the EIL 370 may include an organic layer such as LiF, CsF, NaF, BaF 2 Alkali metal halides or alkaline earth metal halides, and / or organic metal compounds such as Liq, lithium benzoate, sodium stearate, etc., but are not limited thereto.

[0202] When holes are transferred to the second electrode 220 and / or electrons are transferred to the first electrode 210 through the EML 340, the OLED D1 may have a short lifespan and reduced light emission efficiency. To prevent these phenomena, the OLED D1 according to this aspect of the present invention may have at least one exciton blocking layer adjacent to the EML 340.

[0203] For example, the OLED D1 may include an EBL 330 between the HTL 320 and the EML 340 in order to control and prevent electron transmission. In an exemplary aspect, the 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 are not limited thereto.

[0204] In addition, the OLED D1 may further include an HBL 350 between the EML 340 and the ETL 360 as a second exciton blocking layer so that holes cannot be transferred from the EML 340 to the ETL 360. In an exemplary aspect, the HBL 350 may include at least one of oxadiazole compounds, triazole compounds, phenanthroline compounds, benzoxazole compounds, benzothiazole compounds, benzimidazole compounds, and triazine compounds, each of which may be used in the ETL 360, but is not limited thereto.

[0205] For example, the HBL 350 may include a compound having a relatively low HOMO energy level compared to the light emitting material in the EML 340. The HBL 350 may include Alq 3 , BAlq, Liq, PBD, spirocyclic PBD, BCP, bis-4,5-(3,5-di-3-pyridylphenyl)-2-methylpyrimidine (B3PYMPM), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 9-(6-(9H-carbazole-9-yl)pyridin-3-yl)-9H-3,9'-dicarbazole, diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide (TSPO1) and combinations thereof, but are not limited thereto.

[0206] As described above, the EML 340 may include a host and a dopant. The dopant may include an organic metal compound having a structure of Chemical Formula 1 to Chemical Formula 16.

[0207] The matrix used with the dopant may include: 9-(3-(9H-carbazole-9-yl)phenyl)-9H-carbazole-3-carbonitrile (mCP-CN), CBP, mCBP, mCP, DPEPO, 2,8-bis(diphenylphosphoryl)dibenzothiophene (PPT), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene (TmPyPB), 2,6-bis(9H-carbazole-9-yl)pyridine (PYD-2Cz), 2,8-bis(9H-carbazole)pyridine (PYD-2Cz), 2,8-bis(9H-carbazole)pyridine (PYD-2Cz), 2,8-bis(diphenylphosphoryl)dibenzothiophene (PPT), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene (TmPyPB), 2,6-bis(9H-carbazole-9-yl)pyridine (PYD-2Cz), 2,8-bis(9H-carbazole)pyridine (PYD-2Cz), 2,8-bis(diphenylphosphoryl)dibenzothiophene (PPT), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene (TmPyPB), 2,6-bis(9H-carbazole)pyridine (PYD-2Cz), 2,8-bis(diphenylphosphoryl)dibenzothiophene (PPT), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene (TmPyPB), 2,8-bis(9H-carbazole)pyridine (PYD-2Cz), 2,8-bis(diphenylphosphoryl)dibenzothiophene (PPT), 1,3, -9-yl) dibenzothiophene (DCzDBT), 3',5'-di(carbazole-9-yl)-[1,1'-biphenyl]-3,5-dicarbonitrile (DCzTPA), 4'-(9H-carbazole-9-yl)biphenyl-3,5-dicarbonitrile (pCzB-2CN), 3'-(9H-carbazole-9-yl)biphenyl-3,5-dicarbonitrile (mCzB-2CN), TSPO1, 9-(9-phenyl-9H-carbazole-6-yl)-9H-carbazole (CCP), 4- (3-(Triphenylene-2-yl)phenyl)dibenzo[b,d]thiophene, 9-(4-(9H-carbazole-9-yl)phenyl)-9H-3,9'-dicarbazole, 9-(3-(9H-carbazole-9-yl)phenyl)-9H-3,9'-dicarbazole, 9-(6-(9H-carbazole-9-yl)pyridin-3-yl)-9H-3,9'-dicarbazole, 9,9'-diphenyl-9H,9'H-3,3'-dicarbazole (BCzPh), 1,3,5-tri(carbazole- 9-yl)benzene (TCP), TCTA, 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 2,7-bis(carbazole-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,2',7,7'-tetra(carbazole-9-yl)-9,9-spirofluorene (Spiro-CBP), 3,6-bis(carbazole-9-yl)-9-(2-ethyl-hexyl)-9H-carbazole (TCz1), and combinations thereof, but are not limited thereto. For example, the content of the dopant in the EML 340 may be between about 1 wt % and about 50 wt %, for example, between about 1 wt % and about 30 wt %.

[0208] As described above, since the organic metal compounds having the structures of Chemical Formula 1 to Chemical Formula 16 have narrow FWHM and rigid chemical conformation, they can exhibit excellent color purity and luminescence lifetime during the luminescence process and maintain their stable chemical conformation. Changing the structure of the bidentate ligand and the substituent of the ligand can allow the organic metal compound to control its luminescent color. Therefore, OLED D1 can improve its luminescence efficiency and luminescence lifetime.

[0209] In the above exemplary first aspect, the OLED and the organic light emitting display device include a single light emitting portion that emits yellow to red. Differently, the organic light emitting display device can realize full colors including white. Figure 4 is a schematic cross-sectional view illustrating an organic light emitting display device according to another exemplary aspect of the present disclosure.

[0210] like Figure 4 As shown in the figure, the organic light-emitting display device 400 includes: a first substrate 402 that defines individual red pixels RP, green pixels GP and blue pixels BP; a second substrate 404 facing the first substrate 402; a thin film transistor Tr above the first substrate 402; an organic light-emitting diode D arranged between the first substrate 402 and the second substrate 404 and emitting white (W) light; and a color filter layer 480 arranged between the organic light-emitting diode D and the second substrate 404.

[0211] The first substrate 402 and the second substrate 404 may each include glass, flexible material and / or polymer plastic, but are not limited thereto. For example, the first substrate 402 and the second substrate 404 may each be made of PI, PES, PEN, PET, PC, and a combination thereof. The first substrate 402 on which the thin film transistors Tr and the organic light emitting diodes D are arranged forms an array substrate.

[0212] A buffer layer 406 may be disposed over the first substrate 402, and thin film transistors Tr are disposed over the buffer layer 406 corresponding to the respective red pixels RP, green pixels GP, and blue pixels BP. The buffer layer 406 may be omitted.

[0213] The semiconductor layer 410 is disposed over the buffer layer 406. The semiconductor layer 410 may be made of an oxide semiconductor material or polysilicon.

[0214] The gate insulating layer 420 is disposed on the semiconductor layer 410. The gate insulating layer 420 includes an insulating material, such as silicon oxide (SiO x , where 0≤x≤2) or silicon nitride (SiN x , where 0≤x≤2) is an inorganic insulating material.

[0215] The gate electrode 430 made of a conductive material such as metal is disposed over the gate insulating layer 420 so as to correspond to the center of the semiconductor layer 410. An interlayer insulating layer 440 is disposed on the gate electrode 430. The interlayer insulating layer 440 includes an insulating material such as SiO x or SiN x An inorganic insulating material, or an organic insulating material such as benzocyclobutene or photo acrylic.

[0216] The interlayer insulating layer 440 has first and second semiconductor layer contact holes 442 and 444 exposing both sides of the semiconductor layer 410. The first and second semiconductor layer contact holes 442 and 444 are disposed at opposite sides of the gate 430 at intervals spaced apart therefrom.

[0217] The source electrode 452 and the drain electrode 454 made of a conductive material such as metal are disposed on the interlayer insulating layer 440. The source electrode 452 and the drain electrode 454 are spaced apart from each other with respect to the gate 430 and contact both sides of the semiconductor layer 410 through the first semiconductor layer contact hole 442 and the second semiconductor layer contact hole 444, respectively.

[0218] The semiconductor layer 410 , the gate electrode 430 , the source electrode 452 , and the drain electrode 454 constitute a thin film transistor Tr serving as a driving element.

[0219] Despite Figure 4 Although not shown in the figure, gate lines and data lines that cross each other to define the pixel area, and switching elements connected to the gate lines and data lines may also be formed in the pixel area. The switching element is connected to a thin film transistor Tr as a driving element. In addition, the power line is spaced apart in parallel with the gate line or the data line, and the thin film transistor Tr may further include a storage capacitor configured to constantly maintain the voltage of the gate within one frame.

[0220] The passivation layer 460 is disposed on the source electrode 452 and the drain electrode 454 and covers the entire thin film transistor Tr over the first substrate 402. The passivation layer 460 has a drain contact hole 462 exposing the drain electrode 454 of the thin film transistor Tr.

[0221] The OLED D is located above the passivation layer 460. The OLED D includes: a first electrode 510 connected to the drain electrode 454 of the thin film transistor Tr; a second electrode 520 facing the first electrode 510; and a light emitting layer 530 disposed between the first electrode 510 and the second electrode 520.

[0222] The first electrode 510 formed for each pixel region may be an anode and may include a conductive material having a relatively high work function value. For example, the first electrode 510 may include ITO, IZO, ITZO, SnO, ZnO, ICO, AZO, etc. Alternatively, a reflective electrode or a reflective layer may be disposed below the first electrode 510. For example, the reflective electrode or the reflective layer may include Ag or an APC alloy, but is not limited thereto.

[0223] The bank layer 464 is disposed on the passivation layer 460 so as to cover the edge of the first electrode 510. The bank layer 464 exposes the center of the first electrode 510 corresponding to each of the red pixel RP, the green pixel GP, and the blue pixel BP. The bank layer 464 may be omitted.

[0224] The light emitting layer 530, which may include a light emitting portion, is disposed on the first electrode 510. Figure 5 and Figure 6 As shown in , the light emitting layer 530 may include a plurality of light emitting portions 600, 700, 700A and 800 and at least one charge generating layer 680 and 780. The light emitting portions 600, 700, 700A and 800 each include a light emitting material layer, and may further include a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and / or an electron injection layer.

[0225] The second electrode 520 is disposed over the first substrate 402 on which the light emitting layer 530 is disposed. The second electrode 520 may be disposed over the entire display area, and may include a conductive material having a relatively low work function value compared to the first electrode 510, and may be a cathode. For example, the second electrode 520 may include Al, Mg, Ca, Ag, an alloy thereof, or a combination thereof, such as Al-Mg, but is not limited thereto.

[0226] In the organic light emitting display device 400 according to the second embodiment of the present disclosure, since light emitted from the light emitting layer 530 is incident to the color filter layer 480 through the second electrode 520 , the second electrode 520 has a thin thickness so that the light may be transmitted.

[0227] The color filter layer 480 is disposed above the OLED D and includes a red color filter 482, a green color filter 484, and a blue color filter 486, which are respectively disposed corresponding to the red pixel RP, the green pixel GP, and the blue pixel BP. Figure 4 Although not shown in the figure, the color filter layer 480 may be attached to the OLED D through an adhesive layer. Alternatively, the color filter layer 480 may be directly disposed on the OLED D.

[0228] In addition, an encapsulation film may be disposed over the second electrode 520 in order to prevent external moisture from penetrating into the OLED D. The encapsulation film may have a stacked structure of a first inorganic insulating film, an organic insulating film, and a second inorganic insulating film (see FIG. Figure 2 170 in the figure), but is not limited thereto. In addition, a polarizing plate may be attached to the second substrate 404 to reduce reflection of external light. For example, the polarizing plate may be a circular polarizing plate.

[0229] exist Figure 4, light emitted from the OLED D is transmitted through the second electrode 520, and the color filter layer 480 is disposed above the OLED D. Alternatively, light emitted from the OLED D is transmitted through the first electrode 510, and the color filter layer 480 may be disposed between the OLED D and the first substrate 402. In addition, a color conversion layer may be formed between the OLED D and the color filter layer 480. The color conversion layer may include a red conversion layer, a green conversion layer, and a blue conversion layer, each of which is disposed corresponding to each pixel (RP, GP, and BP) to convert white (W) light into red light, green light, and blue light, respectively. Alternatively, the organic light emitting display device 400 may include a color conversion film instead of the color filter layer 480.

[0230] As described above, white (W) light emitted from OLED D is transmitted through red filter 482, green filter 484, and blue filter 486, which are each respectively arranged to correspond to red pixel RP, green pixel GP, and blue pixel BP, so that red light, green light, and blue light are displayed in red pixel RP, green pixel GP, and blue pixel BP.

[0231] Figure 5 is a schematic cross-sectional view showing an organic light emitting diode having a series structure of two light emitting portions. Figure 5 As shown in FIG. 1 , an organic light emitting diode D2 (OLED D2) according to an exemplary embodiment includes a first electrode 510 and a second electrode 520 and a light emitting layer 530 disposed between the first electrode 510 and the second electrode 520. The light emitting layer 530 includes: a first light emitting portion 600 disposed between the first electrode 510 and the second electrode 520; a second light emitting portion 700 disposed between the first light emitting portion 600 and the second electrode 520; and a charge generation layer (CGL) 680 disposed between the first light emitting portion 600 and the second light emitting portion 700.

[0232] The first electrode 510 may be an anode and may include a conductive material having a relatively high work function value. For example, the first electrode 510 may include ITO, IZO, ITZO, SnO, ZnO, ICO, AZO, etc. The second electrode 520 may be a cathode and may include a conductive material having a relatively low work function value. For example, the second electrode 520 may include Al, Mg, Ca, Ag, an alloy thereof, or a combination thereof, such as Al-Mg, but is not limited thereto.

[0233] The first light emitting portion 600 includes a first EML (EML1) 640. The first light emitting portion 600 may further include at least one of a HIL 610 disposed between the first electrode 510 and the EML1 640, a first HTL (HTL1) 620 disposed between the HIL 610 and the EML1 640, and a first ETL (ETL1) 660 disposed between the EML1 640 and the CGL 680. Alternatively, the first light emitting portion 600 may further include a first EBL (EBL1) 630 disposed between the HTL1 620 and the EML1 640 and / or a first HBL (HBL1) 650 disposed between the EML1 640 and the ETL1 660.

[0234] The second light emitting portion 700 includes a second EML (EML2) 740. The second light emitting portion 700 may further include at least one of a second HTL (HTL2) 720, a second ETL (ETL2) 760 disposed between the second electrode 520 and the EML2 740, and an EIL 770 disposed between the second electrode 520 and the ETL2 760. Alternatively, the second light emitting portion 700 may further include a second EBL (EBL 2) 730 disposed between the HTL2 720 and the EML2 740 and / or a second HBL (HBL2) 750 disposed between the EML2 740 and the ETL2 760.

[0235] At least one of EML1 640 and EML2740 may include an organic metal compound having a structure of any one of Chemical Formulas 1 to 16 to emit yellow to red. The other of EML1 640 and EML2740 may emit blue so that OLED D2 may achieve white (W) light emission. Hereinafter, OLED D2 in which EML2740 includes an organic metal compound having a structure of any one of Chemical Formulas 1 to 16 will be described in detail.

[0236] The HIL 610 is disposed between the first electrode 510 and the HTL1 620 and improves the interface performance between the inorganic first electrode 510 and the organic HTL1 620. In one exemplary embodiment, the HIL 610 may include 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-fluorene-2-amine, NPNPB, and combinations thereof, but is not limited thereto. The HIL 610 may be omitted depending on the performance of the OLED D2.

[0237] HTL1620 and HTL2720 may each include TPD, NPB (NPD), DNTPD, CBP, Poly-TPD, TFB, TAPC, DCDPA, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl-4-amine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, but are not limited thereto.

[0238] ETL1 660 and ETL2 760 each promote electron transport in each first light-emitting portion 600 and second light-emitting portion 700. As an example, ETL1 660 and ETL2 760 may each independently include at least one of oxadiazole compounds, triazole compounds, phenanthroline compounds, benzoxazole compounds, benzothiazole compounds, benzimidazole compounds, triazine compounds, etc., but are not limited thereto. For example, ETL1 660 and ETL2 770 may each include Alq 3 , BAlq, Liq, PBD, spiro-PBD, TPBi, Bphen, NBphen, BCP, TAZ, NTAZ, TpPyPB, TmPPPyTz, PFNBr, TPQ, TSPO1, ZADN and combinations thereof, but are not limited thereto.

[0239] The EIL 770 is disposed between the second electrode 520 and the ETL2 760 and can improve the physical properties of the second electrode 520, and thus, can improve the life span of the OLED D2. In an exemplary aspect, the EIL 770 may include an alkali metal halide or an alkaline earth metal halide such as LiF, CsF, NaF, BaF 2 etc., and / or organic metal compounds such as Liq, lithium benzoate, sodium stearate, etc., but are not limited thereto.

[0240] EBL1 630 and EBL2 730 may each independently include TCTA, tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, TAPC, MTDATA, mCP, mCBP, CuPc, DNTPD, TDAPB, DCDPA, 2,8-bis(9-phenyl-9H-carbazole-3-yl)dibenzo[b,d]thiophene and combinations thereof, but are not limited thereto.

[0241] HBL1 650 and HBL2 750 may each include at least one of oxadiazole compounds, triazole compounds, phenanthroline compounds, benzoxazole compounds, benzothiazole compounds, benzimidazole compounds, and triazine compounds that can be used in ETL1 660 and ETL2 760, but are not limited thereto. For example, HBL1 650 and HBL2 750 may each independently include Alq 3 , BAlq, Liq, PBD, spiro-PBD, BCP, B3PYMPM, DPEPO, 9-(6-(9H-carbazol-9-yl)pyridin-3-yl)-9H-3,9'-dicarbazole, TSPO1, and combinations thereof, but are not limited thereto.

[0242] The CGL 680 is disposed between the first light emitting portion 600 and the second light emitting portion 700. The CGL 680 includes an N-type CGL (N-CGL) 685 disposed adjacent to the first light emitting portion 600 and a P-type CGL (P-CGL) 690 disposed adjacent to the second light emitting portion 700. The N-CGL 685 transfers electrons to the EML1 640 of the first light emitting portion 600, and the P-CGL 690 transfers holes to the EML2 740 of the second light emitting portion 700.

[0243] N-CGL 685 may be an organic layer doped with alkali metals such as Li, Na, K, and Cs and / or alkaline earth metals such as Mg, Sr, Ba, and Ra. The matrix in N-CGL 685 may include Bphen and MTDATA, but is not limited thereto. The content of the alkali metal or alkaline earth metal in N-CGL 685 may be between about 0.01 wt % and about 30 wt %.

[0244] P-CGL 690 may include: selected from tungsten oxide (WO x , 2≤x≤3), molybdenum oxide (MoO x , 2≤x≤3), V 2 O 5 and inorganic materials of combinations thereof; and / or organic materials selected from NPD, HAT-CN, F4TCNQ, TPD, N,N,N',N'-tetranaphthyl-benzidine (TNB), TCTA, N,N'-dioctyl-3,4,9,10-perylene dicarboximide (PTCDI-C8) and combinations thereof, but not limited thereto.

[0245] The EML2 740 may include a lower EML 742 disposed between the EBL2 730 and the HBL2 750 and an upper EML 744 disposed between the lower EML 742 and the HBL2 750. One of the lower EML 742 and the upper EML 744 may emit yellow to red, and the other of the lower EML 742 and the upper EML 744 may emit green. Hereinafter, the EML2 740 in which the lower EML 742 emits green and the upper EML 744 emits red will be described in detail.

[0246] The lower EML 742 includes a host and a green dopant. The host may be the same as the first host and the green dopant may include at least one of a green phosphorescent material, a green fluorescent material, and a green delayed fluorescent material.

[0247] The upper EML 744 may include a first host and a first dopant. As an example, the first dopant includes an organic metal compound having a structure of any one of Chemical Formulas 1 to 16 to emit yellow to red colors. The first matrix may include mCP-CN, CBP, mCBP, mCP, DPEPO, PPT, TmPyPB, PYD-2Cz, DCzDBT, DCzTPA, pCzB-2CN), mCzB-2CN, TSPO1, CCP, 4-(3-(triphenylene-2-yl)phenyl)dibenzo[b,d]thiophene, 9-(4-(9H-carbazole-9-yl)phenyl)-9H-3,9'-dicarbazole, 9-(3-(9H-carbazole-9-yl)phenyl)-9H-3,9'-dicarbazole, 9-(6-(9H-carbazole-9-yl)pyridin-3-yl)-9H-3,9'-dicarbazole, BCzPh, TCP, TCTA, CDBP, DMFL-CBP, Spiro-CBP, TCz1 and combinations thereof, but are not limited thereto. For example, the content of the dopant in the upper EML 742 may be between about 1 wt % and about 50 wt %, for example, between about 1 wt % and about 30 wt %.

[0248] EML1 640 may be a blue EML. In this case, EML1 640 may be a blue EML, a sky blue EML, or a dark blue EML. EML1 640 may include a host and a blue dopant. The host may be the same as the first host and the blue dopant may include at least one of a blue phosphorescent material, a blue fluorescent material, and a blue delayed fluorescent material.

[0249] The OLED D2 according to this aspect has a tandem structure and includes at least one of the organometallic compounds having structures of Chemical Formula 1 to Chemical Formula 16. The OLED D2 including the organometallic compound having excellent thermal properties, a rigid chemical conformation, and adjustable emission color can improve its emission efficiency and emission lifetime.

[0250] The OLED may have three or more light emitting parts to form a tandem structure. Figure 6 is a schematic cross-sectional view showing an organic light emitting diode according to another exemplary aspect of the present disclosure. Figure 6 As shown in FIG. 1 , an organic light emitting diode D3 (OLED D3) includes a first electrode 510 and a second electrode 520 facing each other, and a light emitting layer 530A disposed between the first electrode 510 and the second electrode 520. The light emitting layer 530A includes: a first light emitting portion 600 disposed between the first electrode 510 and the second electrode 520; a second light emitting portion 700A disposed between the first light emitting portion 600 and the second electrode 520; a third light emitting portion 800 disposed between the second light emitting portion 700A and the second electrode 520; a first charge generation layer (CGL1) 680 disposed between the first light emitting portion 600 and the second light emitting portion 700A; and a second charge generation layer (CGL2) 780 disposed between the second light emitting portion 700A and the third light emitting portion 800.

[0251] The first light emitting portion 600 includes a first EML (EML1) 640. The first light emitting portion 600 may further include at least one of: a HIL 610 disposed between the first electrode 510 and the EML1 640; a first HTL (HTL1) 620 disposed between the HIL 610 and the EML1 640; and a first ETL (ETL1) 660 disposed between the EML1 640 and the CGL 680. Alternatively, the first light emitting portion 600 may further include a first EBL (EBL1) 630 disposed between the HTL1 620 and the EML1 640 and / or a first HBL (HBL1) 650 disposed between the EML1 640 and the ETL1 660.

[0252] The second light emitting portion 700A includes a second EML (EML2) 740. The second light emitting portion 700A may further include at least one of a second HTL (HTL2) 720 and a second ETL (ETL2) 760 disposed between the second electrode 520 and the EML2 740. Alternatively, the second light emitting portion 700A may further include a second EBL (EBL2) 730 disposed between the HTL2 720 and the EML2 740 and / or a second HBL (HBL2) 750 disposed between the EML2 740 and the ETL2 760.

[0253] The third light emitting portion 800 includes a third EML (EML3) 840. The third light emitting portion 800 may further include: a third HTL (HTL3) 820; a third ETL (ETL3) 860 disposed between the second electrode 520 and the EML3 840; and at least one of an EIL 870 disposed between the second electrode 520 and the ETL3 860. Alternatively, the third light emitting portion 800 may further include: a third EBL (EBL3) 830 disposed between the HTL3 820 and the EML3 840; and / or a third HBL (HBL3) 850 disposed between the EML3 840 and the ETL3 860.

[0254] At least one of EML1 640, EML2 740, and EML3 840 may include an organic metal compound having a structure of Chemical Formula 1 to Chemical Formula 16. For example, one of EML1 640, EML2 740, and EML3 840 may emit red to green. In addition, another one of EML1 640, EML2 740, and EML3 840 emits blue, so that OLED D3 may achieve white light emission. Hereinafter, an OLED in which EML2 740 includes an organic metal compound having a structure of any one of Chemical Formula 1 to Chemical Formula 16 to emit red to green and EML1 640 and EML3 840 each emit blue light will be described in detail.

[0255] The CGL1 680 is disposed between the first light emitting portion 600 and the second light emitting portion 700A, and the CGL2 780 is disposed between the second light emitting portion 700A and the third light emitting portion 800. The CGL1 680 includes a first N-type CGL (N-CGL1) 685 disposed adjacent to the first light emitting portion 600 and a first P-type CGL (P-CGL1) 690 disposed adjacent to the second light emitting portion 700A. The CGL2 780 includes a second N-type CGL (N-CGL2) 785 disposed adjacent to the second light emitting portion 700A and a second P-type CGL (P-CGL2) 790 disposed adjacent to the third light emitting portion 800. N-CGL1 685 and N-CGL2 785 each transport electrons to EML1 640 of the first light emitting portion 600 and EML2 740 of the second light emitting portion 700A, respectively, and P-CGL1 690 and P-CGL2 790 each transport holes to EML2 740 of the second light emitting portion 700A and EML3 840 of the third light emitting portion 800, respectively.

[0256] The EML2 740 may include a lower EML 740A disposed between the EBL2 730 and the HBL2 750 and an upper EML 740B disposed between the lower EML 740A and the HBL2 750. One of the lower EML 740A and the upper EML 740B may emit yellow to red, and the other of the lower EML 740A and the upper EML 740B may emit green. Hereinafter, the EML2 740 in which the lower EML 742 emits green and the upper EML 740B emits red will be described in detail.

[0257] The lower EML 740A includes a host and a green dopant. The host may be the same as the first host and the green dopant may include at least one of a green phosphorescent material, a green fluorescent material, and a green delayed fluorescent material.

[0258] The upper EML 740B may include a first host and a first dopant. As an example, the first dopant includes an organic metal compound having a structure of any one of Chemical Formulas 1 to 16 to emit yellow to red. For example, the content of the dopant in the upper EML 740B may be between about 1 wt % and about 50 wt %, for example, between about 1 wt % and about 30 wt %.

[0259] EML1 640 and EML3 840 may each independently be a blue EML. In this case, EML1 640 and EML3 840 may each independently be a blue EML, a sky blue EML, or a dark blue EML. EML1 640 and EML3 840 may each independently include a host and a blue dopant. The host may be the same as the first host and the blue dopant may include at least one of a blue phosphorescent material, a blue fluorescent material, and a blue delayed fluorescent material.

[0260] The OLED D3 according to this aspect includes an organic metal compound having a structure of any one of Chemical Formulas 1 to 16 in at least one light-emitting material layer. The organic metal compound has a narrow FWHM and can maintain its stable chemical conformation during light emission. The OLED including the organic metal compound and having three light-emitting parts can achieve white light emission and has improved light emission efficiency, color purity, and light emission lifetime.

[0261] Synthesis Example 1: Synthesis of Compound 369

[0262] (1) Synthesis of intermediate B-1

[0263] [Reaction formula 1-1]

[0264]

[0265] Compound A-1 (5-bromoquinoline, 50.0 g, 240.33 mmol), propane-2-ylboronic acid (42.25 g, 480.65 mmol), Pd 2 (dba) 3 (tris(dibenzylideneacetone)dipalladium(0), 6.6 g, 3 mol%), SPhos(2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 9.9 g, 24.03 mmol), potassium phosphate monohydrate (276.71 g, 1.2 mol) and toluene (1000 mL) were put into a reaction vessel, and then the solution was stirred at 120° C. for 12 hours. After the reaction was completed, the solution was cooled to room temperature, and the solution was extracted with ethyl acetate to remove the solvent. The crude product was purified by column chromatography (eluent: ethyl acetate and hexane) to obtain intermediate B-1 (5-isopropylquinoline, 35.4 g, yield: 86%).

[0266] MS (m / z).:171.10

[0267] (2) Synthesis of intermediate C-1

[0268] [Reaction 1-2]

[0269]

[0270] Intermediate B-1 (5-isopropylquinoline, 35.4 g, 206.73 mmol), mCBPA (3-chloroperbenzoic acid, 53.5 g, 310.09 mmol) and dichloromethane (500 mL) were placed in a reaction vessel, and the solution was stirred at room temperature for 3 hours. Sodium sulfite (80 g) was added to the solution, and the organic layer was washed with water and then placed under reduced pressure to obtain Intermediate C-1 (27.5 g, yield: 71%).

[0271] MS (m / z): 187.10

[0272] (3) Synthesis of intermediate D1

[0273] [Reaction 1-3]

[0274]

[0275] The intermediate C-1 (27.5 g, 146.87 mmol) dissolved in toluene (500 mL) was placed in a reaction vessel, and phosphorus oxychloride (POCl 3, 45.0 g, 293.74 mmol) and diisopropylethylamine (DIPEA, 38.0 g, 293.74 mmol) were added to the container, and then the solution was stirred at 120 ° C for 4 hours. The reactant was placed under reduced pressure to remove the solvent and extracted with dichloromethane, and then the organic layer was washed with water. MgSO 4 Water was removed, the crude product was filtered, and then the solvent was removed. The crude product was purified by column chromatography to obtain Intermediate D-1 (2-chloro-5-isopropylquinoline, 11.8 g, yield: 39%).

[0276] MS (m / z): 205.07

[0277] (4) Synthesis of intermediate F-1

[0278] [Reaction 1-4]

[0279]

[0280] Compound E-1 (1-naphthoic acid, 50 g, 290.30 mmol) and SOCl 2 (200 mL) was placed in a reaction vessel and the solution was refluxed for 4 hours to remove SOCl 2 , ethanol (200 mL) was added, and the solution was stirred at 70 °C for 7 hours. Water was added, and the organic layer was extracted with ether and MgSO 4 Water was removed, and then the solution was filtered. The solution was placed under reduced pressure to remove the solvent and obtain Intermediate F-1 (ethyl-1-naphthoate, 53.2 g, yield: 90%).

[0281] MS (m / z): 200.08

[0282] (5) Synthesis of intermediate G-1

[0283] [Reaction 1-5]

[0284]

[0285] Intermediate F-1 (ethyl-1-naphthoate, 52.3 g, 261.20 mmol), NBS (N-bromosuccinimide, 51.14 g, 287.32 mmol), Pd(OAc) 2 (palladium(II) acetate, 0.6 g, 2.61 mmol), Na 2 S 2 O 8(124.4 g, 522.40 mmol) and dichloromethane (500 mL) were placed in a reaction vessel, TfOH (trifluoromethanesulfonic acid, 19.6 g, 130.60 mmol) was added to the reaction vessel, and then the solution was stirred at 70 ° C for 1 hour. The reactants were cooled to room temperature and NaHCO 3 The reaction was allowed to complete and then extracted with dichloromethane. 4 The water in the organic layer was removed, the solvent was removed, and then the crude product was purified by column chromatography (eluent: petroleum ether and ethyl acetate) to obtain Intermediate G-1 (ethyl-8-bromonaphthalene-1-carboxylate, 54.0 g, yield: 74%).

[0286] MS (m / z): 277.99

[0287] (6) Synthesis of intermediate H-1

[0288] [Reaction 1-6]

[0289]

[0290] Intermediate G-1 (ethyl-8-bromonaphthalene-1-carboxylate, 54.0 g, 193.46 mmol), bis(pinacolato)diboron (58.6 g, 232.15 mmol), Pd(dppf)Cl 2 ([1.1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), 7.1 g, 9.67 mmol), KOAc (potassium acetate, 57.0 g, 580.37 mmol) and 1,4-dioxane (500 mL) were placed in a reaction vessel, and the solution was stirred at 100° C. for 4 hours. The reactant was cooled to room temperature, extracted with ethyl acetate, and then MgSO 4 The water in the organic layer was removed, and then the solution was filtered and placed under reduced pressure to remove the solvent. The crude product was purified by column chromatography (eluent: hexane and ethyl acetate) to obtain intermediate H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylic acid ethyl ester, 54.3 g, yield: 86%).

[0291] MS (m / z): 326.17

[0292] (7) Synthesis of intermediate I-1

[0293] [Reaction 1-7]

[0294]

[0295] Intermediate D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol), intermediate H-1 (ethyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylate, 17.45 g, 53.48 mmol), Pd(OAc) 2 (0.5 g, 2.43 mmol), PPh 3 (chloro(triphenylphosphine)[2-(2′-amino-1,1′-biphenyl)]palladium(II), 2.6 g, 9.72 mmol), K 2 CO 3 (20.2 g, 145.86 mmol), 1,4-dioxane (100 mL) and water (100 mL) were placed in a reaction vessel, and the solution was stirred at 100 °C for 12 hours. The reactant was cooled to room temperature and extracted with ethyl acetate and washed with MgSO 4 The water in the organic layer was removed, and then the solution was filtered and placed under reduced pressure to remove the solvent. The crude product was purified by column chromatography (eluent: hexane and ethyl acetate) to obtain intermediate I-1 (8-(5-isopropylquinolin-2-yl)naphthalene-1-carboxylic acid ethyl ester, 13.5 g, yield: 75%).

[0296] MS (m / z): 369.17

[0297] (8) Synthesis of intermediate J-1

[0298] [Reaction 1-8]

[0299]

[0300] Intermediate I-1 (ethyl 8-(5-isopropylquinolin-2-yl)naphthalene-1-carboxylate, 13.5 g, 36.6 mmol) and THF (100 mL) were placed in a reaction vessel, and then CH 3 MgBr (21.8 g, 182.70 mmol) was added dropwise to the reaction vessel. The solution was raised to room temperature and the reaction was complete after 12 hours. The mixture was extracted with ethyl acetate and washed with MgSO 4 The water in the organic layer was removed, and then the solution was filtered and placed under reduced pressure to remove the solvent. The crude product was purified by column chromatography (eluent: hexane and ethyl acetate) to obtain intermediate J-1 (2-(1-(5-isopropylquinolin-2-yl)naphthalen-8-yl)propan-2-ol, 6.9 g, yield: 53%).

[0301] MS (m / z): 355.19

[0302] (9) Synthesis of intermediate K-1

[0303] [Reaction 1-9]

[0304]

[0305] Intermediate J-1 (2-(1-(5-isopropylquinoline-2-yl)naphthalen-8-yl)propan-2-ol, 20 g, 56.26 mmol) and a mixed aqueous solution of acetic acid and sulfuric acid (200 mL) were placed in a reaction vessel, and the solution was refluxed for 16 hours. After the reaction was completed, the solution was cooled to room temperature, and the reactant was then added dropwise to an aqueous sodium hydroxide solution with ice. The organic layer was extracted with dichloromethane and MgSO 4 Water was removed. The solvent was removed, and the crude product was then recrystallized with toluene and ethanol to obtain Intermediate K-1 (9-isopropyl-7,7-dimethyl-7H-naphtho[1,8-bc]acridine, 10.25 g, yield: 54%) as a yellow solid.

[0306] MS (m / z): 337.18

[0307] (10) Synthesis of intermediate L-1

[0308] [Reaction formula 1-10]

[0309]

[0310] Intermediate K-1 (10.25 g, 30.37 mmol), 2-ethoxyethanol (200 mL) and distilled water (50 mL) were placed in a reaction vessel, and the solution was bubbled with nitrogen for 1 hour to remove IrCl 3 ·H 2 O (4.4g, 13.81mmol) was added to the reaction vessel, and the solution was then refluxed for 2 days. After the reaction was complete, the solution was cooled to room temperature and the solid obtained was then filtered. The solid was washed with hexane and water and dried to obtain intermediate L-1 (4.0g, yield: 32%).

[0311] (11) Synthesis of Compound 369

[0312] [Reaction 1-11]

[0313]

[0314] Intermediate L-1 (4.0 g, 2.21 mmol), 3,7-diethylnonane-4,6-dione (4.7 g, 22.09 mmol), Na 2 CO 3(4.7g, 441.8mmol) and 2-ethoxyethanol (100mL) were placed in a reaction vessel, and the solution was then slowly stirred for 24 hours. After the reaction was complete, dichloromethane was added to the reactant to dissolve the product, and the solution was then filtered through diatomaceous earth. The solvent was removed, the solid was filtered using filter paper, and the filtered solid was then placed in isopropanol, and the solution was then stirred. The solution was filtered to remove isopropanol, the solution was dried and recrystallized with dichloromethane and isopropanol. Highly purified compound 369 (2.5g, yield: 53%) was obtained using a sublimation purifier.

[0315] MS (m / z): 1076.48

[0316] Synthesis Example 2: Synthesis of Compound 2

[0317] (1) Synthesis of intermediate C-2

[0318] [Reaction formula 2-1]

[0319]

[0320] Intermediate C-2 (3-6-(isopropylisoquinolin-1-yl)-naphthoic acid ethyl ester (14.4 g, yield: 80%) was obtained by repeating the synthesis process of intermediate I-1, except that compound A-2 (1-chloro-6-isopropylisoquinoline, 10 g, 48.62 mmol) and compound B-2 (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoic acid ethyl ester (17.45 g, 53.50 mmol) were used instead of intermediate D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and intermediate H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylic acid ethyl ester).

[0321] MS (m / z): 369.17

[0322] (2) Synthesis of intermediate D-2

[0323] [Reaction formula 2-2]

[0324]

[0325] Intermediate D-2 (2-(3-(6-isopropylisoquinolin-1-yl)naphthalene-2-yl)propan-2-ol, 6.9 g, yield: 50%) was obtained by repeating the synthesis process of intermediate J-1, except that intermediate C-2 (3-(6-isopropylisoquinolin-1-yl)-2-naphthoic acid ethyl ester, 14.4 g, 39.0 mmol) was used instead of intermediate I-1 (8-(5-isopropylquinolin-2-yl)naphthalene-1-carboxylic acid ethyl ester, 13.5 g, 36.5 mmol).

[0326] MS (m / z): 355.19

[0327] (3) Synthesis of intermediate E-2

[0328] [Reaction 2-3]

[0329]

[0330] Intermediate E-2 (5-isopropyl-7,7-dimethyl-7H-benzo[de]naphtho[2,3-h]quinolone, 11.39 g, yield: 60%) was obtained by repeating the synthetic process of intermediate K-1, except that intermediate D-2 (2-(3-(6-isopropylisoquinolin-1-yl)naphtho[2,3-h]propan-2-ol, 20 g, 56.26 mmol) was used instead of intermediate J-1 (2-(1-(5-isopropylquinolin-2-yl)naphtho[2,3-h]propan-2-ol, 20 g, 56.26 mmol).

[0331] MS (m / z): 337.18

[0332] (4) Synthesis of intermediate F-2

[0333] [Reaction 2-4]

[0334]

[0335] Intermediate F-2 (4.7 g, yield: 34%) was obtained by repeating the synthetic process of Intermediate L-1, except that Intermediate E-2 (11.39 g, 33.76 mmol) was used instead of Intermediate K-1 (10.25 g, 30.37 mmol).

[0336] (5) Synthesis of Compound 2

[0337] [Reaction 2-5]

[0338]

[0339] Compound 2 (3.2 g, yield: 57%) was obtained by repeating the synthetic procedure of Compound 369, except that Intermediate F-2 (4.7 g, 2.61 mmol) was used instead of Intermediate L-1 (4.0 g, 2.21 mmol).

[0340] MS (m / z): 1076.48

[0341] Synthesis Example 3: Synthesis of Compound 501

[0342] (1) Synthesis of intermediate C-3

[0343] [Reaction formula 3-1]

[0344]

[0345] Intermediate C-3 (8-6-(isopropylisoquinolin-3-yl)-naphthoic acid ethyl ester, 12.6 g, yield: 70%) was obtained by repeating the synthesis process of intermediate I-1, except that compound A-3 (3-chloro-6-isopropylisoquinoline, 10 g, 48.62 mmol) was used instead of intermediate D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol).

[0346] MS (m / z): 369.17

[0347] (2) Synthesis of intermediate D-3

[0348] [Reaction formula 3-2]

[0349]

[0350] Intermediate D-3 (2-(8-(6-isopropylisoquinolin-3-yl)naphthyl)propan-2-ol, 7.3 g, yield: 60%) was obtained by repeating the synthesis process of intermediate J-1, except that intermediate C-3 (ethyl 8-(6-isopropylisoquinolin-3-yl)naphthyl)carboxylate, 12.6 g, 34.0 mmol) was used instead of intermediate I-1 (ethyl 8-(5-isopropylquinolin-2-yl)naphthalene-1-carboxylate, 13.5 g, 36.5 mmol).

[0351] MS (m / z): 355.19

[0352] (3) Synthesis of intermediate E-3

[0353] [Reaction formula 3-3]

[0354]

[0355] Intermediate E-3 (2-isopropyl-13,13-dimethyl-13H-naphtho[1,8-bc]phenanthridine, 4.3 g, yield: 62%) was obtained by repeating the synthesis process of intermediate K-1, except that intermediate D-3 (2-(8-(6-isopropylisoquinolin-3-yl)naphthalen-1-yl)propan-2-ol, 7.3 g, 20.4 mmol) was used instead of intermediate J-1 (2-(1-(5-isopropylquinolin-2-yl)naphthalen-8-yl)propan-2-ol, 20 g, 56.26 mmol).

[0356] MS (m / z): 337.18

[0357] (4) Synthesis of intermediate F-3

[0358] [Reaction 3-4]

[0359]

[0360] Intermediate F-3 (1.9 g, yield: 37%) was obtained by repeating the synthesis process of intermediate L-1, except that intermediate E-3 (2-isopropyl-13,13-dimethyl-13H-naphtho[1,8-bc]phenanthridine, 4.3 g, 12.6 mmol) was used instead of intermediate K-1 (10.25 g, 30.37 mmol).

[0361] (5) Synthesis of Compound 501

[0362] [Reaction 3-5]

[0363]

[0364] Compound 501 (1.4 g, yield: 60%) was obtained by repeating the synthetic procedure of compound 369, except that intermediate F-3 (1.9 g, 1.07 mmol) was used instead of intermediate L-1 (4.0 g, 2.21 mmol).

[0365] MS (m / z): 1076.48

[0366] Synthesis Example 4: Synthesis of Compound 182

[0367] (1) Synthesis of intermediate C-4

[0368] [Reaction formula 4-1]

[0369]

[0370] Intermediate C-4 (12.2 g, yield: 68%) was obtained by repeating the synthesis process of intermediate I-1, except that compound A-4 (10 g, 48.62 mmol) and compound B-4 (17.45 g, 53.48 mmol) were used instead of intermediate D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and intermediate H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol), respectively.

[0371] MS (m / z): 369.17

[0372] (2) Synthesis of intermediate D-4

[0373] [Reaction 4-2]

[0374]

[0375] Intermediate D-4 (6.8 g, yield: 58%) was obtained by repeating the synthesis process of intermediate J-1, except using intermediate C-4 (12.2 g, 33.02 mmol) instead of intermediate I-1 (ethyl 8-(5-isopropylquinolin-2-yl)naphthalene-1-carboxylate, 13.5 g, 36.5 mmol).

[0376] MS (m / z): 355.19

[0377] (3) Synthesis of intermediate E-4

[0378] [Reaction 4-3]

[0379]

[0380] Intermediate E-4 (4.1 g, yield: 63%) was obtained by repeating the synthesis process of intermediate K-1, except that intermediate D-4 (6.8 g, 19.15 mmol) was used instead of intermediate J-1 (2-(1-(5-isopropylquinolin-2-yl)naphthalen-8-yl)propan-2-ol, 20 g, 56.26 mmol).

[0381] MS (m / z): 337.18

[0382] (4) Synthesis of intermediate F-4

[0383] [Reaction formula 4-4]

[0384]

[0385] Intermediate F-4 (2.1 g, yield: 42%) was obtained by repeating the synthetic process of Intermediate L-1, except that Intermediate E-4 (4.1 g, 12.15 mmol) was used instead of Intermediate K-1 (10.25 g, 30.37 mmol).

[0386] (5) Synthesis of Compound 182

[0387] [Reaction 4-5]

[0388]

[0389] Compound 182 (1.1 g, yield: 57%) was obtained by repeating the synthetic procedure of compound 369, except that intermediate F-4 (2.1 g, 1.17 mmol) was used instead of intermediate L-1 (4.0 g, 2.21 mmol).

[0390] MS (m / z): 1076.48

[0391] Synthesis Example 5: Synthesis of Compound 154

[0392] (1) Synthesis of intermediate C-5

[0393] [Reaction formula 5-1]

[0394]

[0395] Intermediate C-5 (11.8 g, yield: 78%) was obtained by repeating the synthesis process of intermediate I-1, except that compound A-5 (10 g, 48.62 mmol) and compound B-5 (14.4 g, 53.48 mmol) were used instead of intermediate D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and intermediate H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol), respectively.

[0396] MS (m / z): 312.16

[0397] (2) Synthesis of intermediate D-5

[0398] [Reaction 5-2]

[0399]

[0400] Intermediate C-5 (11.8 g, 37.75 mmol) and dimethyl sulfoxide (DMSO) (200 mL) were placed in a reaction vessel, and then CuI (10.8 g, 56.66 mmol) was added to the reaction vessel, and then the solution was refluxed at 150 ° C for 12 hours. After the reaction was completed, the solution was filtered, extracted with ethyl acetate, and washed with MgSO 4 The water in the organic layer was removed, and then the solution was filtered and placed under reduced pressure to remove the solvent. The crude product was purified by column chromatography (eluent: hexane and ethyl acetate) to obtain Intermediate D-5 (4.6 g, yield: 39%).

[0401] MS (m / z): 310.15

[0402] (3) Synthesis of intermediate E-5

[0403] [Reaction 5-3]

[0404]

[0405] Intermediate D-5 (4.6 g, 14.82 mmol), 1-iodobenzene (3.3 g, 16.30 mmol) and toluene (200 mL) were placed in a reaction vessel, and then Pd 2 (dba) 3 (0.7 g, 0.74 mmol), P(t-Bu) 3 (tri-tert-butylphosphine, 0.3 g, 1.48 mmol) and NaOt-Bu (sodium tert-butoxide, 2.8 g, 29.64 mmol) were added to the reaction vessel, and then the solution was refluxed at 100°C for 24 hours. After the reaction was completed, the solution was extracted with ethyl acetate and MgSO 4 The water in the organic layer was removed, and then the solution was filtered and placed under reduced pressure to remove the solvent. The crude product was purified by column chromatography (eluent: hexane and ethyl acetate) to obtain Intermediate E-5 (4.6 g, yield: 81%).

[0406] MS (m / z): 386.18

[0407] (4) Synthesis of intermediate F-5

[0408] [Reaction 5-4]

[0409]

[0410] Intermediate F-5 (2.5 g, yield: 47%) was obtained by repeating the synthetic process of Intermediate L-1, except that Intermediate E-5 (4.6 g, 11.90 mmol) was used instead of Intermediate K-1 (10.25 g, 30.37 mmol).

[0411] (5) Synthesis of Compound 154

[0412] [Reaction formula 5-5]

[0413]

[0414] Compound 154 (1.4 g, yield: 46%) was obtained by repeating the synthetic procedure of compound 369, except that intermediate F-5 (2.5 g, 1.25 mmol) was used instead of intermediate L-1 (4.0 g, 2.21 mmol).

[0415] MS (m / z): 1174.47

[0416] Synthesis Example 6: Synthesis of Compound 334

[0417] (1) Synthesis of intermediate C-6

[0418] [Reaction formula 6-1]

[0419]

[0420] Intermediate C-6 (11.4 g, yield: 75%) was obtained by repeating the synthesis process of intermediate I-1, except that compound A-6 (10 g, 48.62 mmol) and compound B-6 (14.4 g, 53.48 mmol) were used instead of intermediate D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and intermediate H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol), respectively.

[0421] MS (m / z): 312.16

[0422] (2) Synthesis of intermediate D-6

[0423] [Reaction formula 6-2]

[0424]

[0425] Intermediate D-6 (6.8 g, yield: 58%) was obtained by repeating the synthetic procedure of Intermediate D5, except that Intermediate C-6 (11.4 g, 35.49 mmol) was used instead of Intermediate C-5 (11.8 g, 37.77 mmol).

[0426] MS (m / z): 310.15

[0427] (3) Synthesis of intermediate E-6

[0428] [Reaction formula 6-3]

[0429]

[0430] Intermediate E-6 (5.6 g, yield: 78%) was obtained by repeating the synthetic procedure of Intermediate E-5, except that Intermediate D-6 (5.8 g, 18.61 mmol) was used instead of Intermediate D-5 (4.6 g, 14.82 mmol).

[0431] MS (m / z): 386.18

[0432] (4) Synthesis of intermediate F-6

[0433] [Reaction 6-4]

[0434]

[0435] Intermediate F-6 (2.8 g, yield: 42%) was obtained by repeating the synthetic process of Intermediate L-1, except that Intermediate E-6 (5.6 g, 14.49 mmol) was used instead of Intermediate K-1 (10.25 g, 30.37 mmol).

[0436] (5) Synthesis of Compound 334

[0437] [Reaction 6-5]

[0438]

[0439] Compound 334 (2.0 g, yield: 61%) was obtained by repeating the synthetic procedure of compound 369, except that intermediate F-6 (2.8 g, 1.38 mmol) was used instead of intermediate L-1 (4.0 g, 2.21 mmol).

[0440] MS (m / z): 1174.47

[0441] Synthesis Example 7: Synthesis of Compound 465

[0442] (1) Synthesis of intermediate C-7

[0443] [Reaction formula 7-1]

[0444]

[0445] Intermediate C-7 (9.0 g, yield: 50%) was obtained by repeating the synthesis process of intermediate I-1, except that compound A-7 (10 g, 48.62 mmol) and compound B-7 (14.4 g, 53.48 mmol) were used instead of intermediate D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and intermediate H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol), respectively.

[0446] MS (m / z): 312.16

[0447] (2) Synthesis of intermediate D-7

[0448] [Reaction 7-2]

[0449]

[0450] Intermediate D-7 (7.4 g, yield: 55%) was obtained by repeating the synthetic procedure of Intermediate D-5, except that Intermediate C-7 (9.0 g, 28.69 mmol) was used instead of Intermediate C-5 (11.8 g, 37.77 mmol).

[0451] MS (m / z): 310.15

[0452] (3) Synthesis of intermediate E-7

[0453] [Reaction 7-3]

[0454]

[0455] Intermediate E-7 (4.7 g, yield: 77%) was obtained by repeating the synthetic procedure of Intermediate E-5, except that Intermediate D-7 (4.9 g, 15.78 mmol) was used instead of Intermediate D-5 (4.6 g, 14.82 mmol).

[0456] MS (m / z): 386.18

[0457] (4) Synthesis of intermediate F-7

[0458] [Reaction 7-4]

[0459]

[0460] Intermediate F-7 (2.6 g, yield: 48%) was obtained by repeating the synthetic process of Intermediate L-1, except that Intermediate E-7 (4.7 g, 12.16 mmol) was used instead of Intermediate K-1 (10.25 g, 30.37 mmol).

[0461] (5) Synthesis of Compound 465

[0462] [Reaction 7-5]

[0463]

[0464] Compound 465 (2.0 g, yield: 64%) was obtained by repeating the synthetic procedure of compound 369, except that intermediate F-7 (2.6 g, 1.33 mmol) was used instead of intermediate L-1 (4.0 g, 2.21 mmol).

[0465] MS (m / z): 1174.47

[0466] Synthesis Example 8: Synthesis of Compound 582

[0467] (1) Synthesis of intermediate C-8

[0468] [Reaction formula 8-1]

[0469]

[0470] Intermediate C-8 (9.0 g, yield: 50%) was obtained by repeating the synthesis process of intermediate I-1, except that compound A-8 (10 g, 48.62 mmol) and compound B-8 (14.4 g, 53.48 mmol) were used instead of intermediate D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and intermediate H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol), respectively.

[0471] MS (m / z): 312.16

[0472] (2) Synthesis of intermediate D-8

[0473] [Reaction formula 8-2]

[0474]

[0475] Intermediate D-8 (7.4 g, yield: 55%) was obtained by repeating the synthetic procedure of Intermediate D-5, except that Intermediate C-8 (10.0 g, 35.01 mmol) was used instead of Intermediate C-5 (11.8 g, 37.77 mmol).

[0476] MS (m / z): 310.15

[0477] (3) Synthesis of intermediate E-8

[0478] [Reaction formula 8-3]

[0479]

[0480] Intermediate E-8 (5.3 g, yield: 83%) was obtained by repeating the synthetic procedure of Intermediate E-5, except that Intermediate D-8 (5.1 g, 15.45 mmol) was used instead of Intermediate D-5 (4.6 g, 14.82 mmol).

[0481] MS (m / z): 386.18

[0482] (4) Synthesis of intermediate F-8

[0483] [Reaction 8-4]

[0484]

[0485] Intermediate F-8 (2.4 g, yield: 39%) was obtained by repeating the synthetic process of Intermediate L-1, except that Intermediate E-8 (5.3 g, 13.66 mmol) was used instead of Intermediate K-1 (10.25 g, 30.37 mmol).

[0486] (5) Synthesis of Compound 582

[0487] [Reaction 8-5]

[0488]

[0489] Compound 582 (1.8 g, yield: 64%) was obtained by repeating the synthetic procedure of compound 369, except that intermediate F-8 (2.4 g, 1.1 mmol) was used instead of intermediate L-1 (4.0 g, 2.21 mmol).

[0490] MS (m / z): 1174.47

[0491] Synthesis Example 9: Synthesis of Compound 168

[0492] (1) Synthesis of intermediate C-9

[0493] [Reaction formula 9-1]

[0494]

[0495] Intermediate C-9 (9.9 g, yield: 67%) was obtained by repeating the synthesis process of intermediate I-1, except that compound A-9 (10 g, 44.71 mmol) and compound B-9 (13.3 g, 49.18 mmol) were used instead of intermediate D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and intermediate H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol), respectively.

[0496] MS (m / z): 331.14

[0497] (2) Synthesis of intermediate D-9

[0498] [Reaction formula 9-2]

[0499]

[0500] Intermediate C-9 (9.9 g, 29.88 mmol) and DMF (100 mL) were placed in a reaction vessel, intermediate C-9 was dissolved in DMF, K 2 CO 3 (12.4 g, 89.62 mmol) was added to the reaction vessel, and the solution was then stirred at 100 ° C for 1 hour. After the reaction was completed, the solution was cooled to room temperature, and ethanol (100 mL) was added to the reaction vessel. After the mixture was distilled under reduced pressure, the reactant was recrystallized from chloroform / ethyl acetate to obtain intermediate D-9 (4.9 g, yield: 53%).

[0501] MS (m / z): 311.13

[0502] (3) Synthesis of intermediate E-9

[0503] [Reaction formula 9-3]

[0504]

[0505] Intermediate E-9 (3.1 g, yield: 50%) was obtained by repeating the synthetic process of Intermediate L-1, except that Intermediate D-9 (4.9 g, 15.83 mmol) was used instead of Intermediate K-1 (10.25 g, 30.37 mmol).

[0506] (4) Synthesis of Compound 168

[0507] [Reaction formula 9-4]

[0508]

[0509] Compound 168 (2.0 g, yield: 54%) was obtained by repeating the synthetic procedure of compound 369, except that intermediate E-9 (3.1 g, 1.80 mmol) was used instead of intermediate L-1 (4.0 g, 2.21 mmol).

[0510] MS (m / z): 1024.38

[0511] Synthesis Example 10: Synthesis of Compound 348

[0512] (1) Synthesis of intermediate C-10

[0513] [Reaction formula 10-1]

[0514]

[0515] Intermediate C-10 (9.0 g, yield: 64%) was obtained by repeating the synthesis process of intermediate I-1, except that compound A-10 (10 g, 44.71 mmol) and compound B-10 (13.3 g, 49.18 mmol) were used instead of intermediate D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and intermediate H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol), respectively.

[0516] MS (m / z): 331.14

[0517] (2) Synthesis of intermediate D-10

[0518] [Reaction formula 10-2]

[0519]

[0520] Intermediate D-10 (5.0 g, yield: 55%) was obtained by repeating the synthetic procedure of Intermediate D-9, except that Intermediate C-10 (9.6 g, 29.06 mmol) was used instead of Intermediate C-9 (9.9 g, 28.88 mmol).

[0521] MS (m / z): 311.13

[0522] (3) Synthesis of intermediate E-10

[0523] [Reaction formula 10-3]

[0524]

[0525] Intermediate E-10 (3.5 g, yield: 57%) was obtained by repeating the synthetic process of Intermediate L-1, except that Intermediate D-10 (5.0 g, 15.98 mmol) was used instead of Intermediate K-1 (10.25 g, 30.37 mmol).

[0526] (4) Synthesis of Compound 348

[0527] [Reaction formula 10-4]

[0528]

[0529] Compound 348 (1.8 g, yield: 43%) was obtained by repeating the synthetic procedure of compound 369 except using intermediate E-10 (3.5 g, 2.07 mmol) instead of intermediate L-1 (4.0 g, 2.21 mmol).

[0530] MS (m / z): 1024.38

[0531] Synthesis Example 11: Synthesis of Compound 483

[0532] (1) Synthesis of intermediate C-11

[0533] [Reaction formula 11-1]

[0534]

[0535] Intermediate C-11 (7.9 g, yield: 53%) was obtained by repeating the synthesis process of intermediate I-1, except that compound A-11 (10 g, 44.71 mmol) and compound B-11 (13.3 g, 49.18 mmol) were used instead of intermediate D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and intermediate H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol), respectively.

[0536] MS (m / z): 331.14

[0537] (2) Synthesis of intermediate D-11

[0538] [Reaction formula 11-2]

[0539]

[0540] Intermediate D-11 (3.8 g, yield: 51%) was obtained by repeating the synthetic procedure of Intermediate D-9, except that Intermediate C-11 (7.9 g, 23.07 mmol) was used instead of Intermediate C-9 (9.9 g, 28.88 mmol).

[0541] MS (m / z): 311.13

[0542] (3) Synthesis of intermediate E-11

[0543] [Reaction formula 11-3]

[0544]

[0545] Intermediate E-11 (3.0 g, yield: 63%) was obtained by repeating the synthetic procedure of Intermediate L-1, except that Intermediate D-11 (3.8 g, 12.20 mmol) was used instead of Intermediate K-1 (10.25 g, 30.37 mmol).

[0546] (4) Synthesis of Compound 483

[0547] [Reaction 11-4]

[0548]

[0549] Compound 483 (1.6 g, yield: 44%) was obtained by repeating the synthetic procedure of compound 369, except that intermediate E-11 (3.0 g, 1.75 mmol) was used instead of intermediate L-1 (4.0 g, 2.21 mmol).

[0550] MS (m / z): 1024.38

[0551] Synthesis Example 12: Synthesis of Compound 598

[0552] (1) Synthesis of intermediate C-12

[0553] [Reaction formula 12-1]

[0554]

[0555] Intermediate C-12 (9.8 g, yield: 66%) was obtained by repeating the synthesis process of intermediate I-1, except that compound A-12 (10 g, 44.71 mmol) and compound B-12 (13.3 g, 49.18 mmol) were used instead of intermediate D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and intermediate H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol), respectively.

[0556] MS (m / z): 331.14

[0557] (2) Synthesis of intermediate D-12

[0558] [Reaction 12-2]

[0559]

[0560] Intermediate D-12 (5.0 g, yield: 54%) was obtained by repeating the synthetic procedure of Intermediate D-9, except that Intermediate C-12 (9.8 g, 29.51 mmol) was used instead of Intermediate C-9 (9.9 g, 28.88 mmol).

[0561] MS (m / z): 311.13

[0562] (3) Synthesis of intermediate E-12

[0563] [Reaction 12-3]

[0564]

[0565] Intermediate E-12 (3.4 g, yield: 55%) was obtained by repeating the synthetic process of Intermediate L-1, except that Intermediate D-12 (5.0 g, 15.93 mmol) was used instead of Intermediate K-1 (10.25 g, 30.37 mmol).

[0566] (4) Synthesis of Compound 598

[0567] [Reaction 12-4]

[0568]

[0569] Compound 598 (1.6 g, yield: 39%) was obtained by repeating the synthetic procedure of compound 369, except that intermediate E-12 (3.4 g, 1.99 mmol) was used instead of intermediate L-1 (4.0 g, 2.21 mmol).

[0570] MS (m / z): 1024.38

[0571] Experimental Example 1: Measuring PL Spectra

[0572] The photoluminescence (PL) spectrum of Compound 2 obtained in Synthesis Example 2 was measured using a F25 fluorescence spectrophotometer (Edinburgh Instruments) at room temperature in a dichloromethane solvent. Figure 7 Shown is the PL spectrum of Compound 2. Compound 2 emits light in the red range.

[0573] Example 1: Fabrication of OLED

[0574] Compound 369 obtained in Synthesis Example 1 was applied as a dopant in an emitting material layer (EML) to manufacture an organic light-emitting diode. A glass substrate coated with ITO (100 nm) as a thin film was cleaned with a solvent such as isopropyl alcohol and acetone and ultrasonically cleaned and dried in an oven at 100° C. The substrate was transferred to a vacuum chamber for deposition of the emitting layer. Subsequently, at about 5 to 7*10 -7 Use the following settings: The light-emitting layer and cathode were deposited by heated dish evaporation in the following order:

[0575] Hole injection layer (HIL) (after HI-1 (NPNPB), thickness of 60 nm); hole transport layer (HTL) (NPB, 80 nm), EML (host (after PH, 95 wt%), dopant (compound 369, 5 wt%), 30 nm); ETL-EIL (after ET (2-[4-(9,10-di-2-naphthyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimidazole, ZADN, 50 wt%), Liq (50 wt%), thickness of 30 nm); and cathode (aluminum, thickness of 100 nm).

[0576] Then, a capping layer (CPL) is deposited on the cathode and the device is encapsulated with glass. After the deposition of the light-emitting layer and cathode, the OLED is transferred from the deposition chamber to a drying oven for film formation and then encapsulated using UV-curable epoxy resin and a moisture absorber. The HIL materials, the main body in the EML, and the ETL materials are shown below:

[0577]

[0578] Example 2-12: Fabrication of OLED

[0579] OLEDs were manufactured using the same procedure and the same materials as in Example 1, except that Compound 501 (Ex. 2), Compound 2 (Ex. 3), Compound 182 (Ex. 4), Compound 154 (Ex. 5), Compound 334 (Ex. 6), Compound 465 (Ex. 7), Compound 582 (Ex. 8), Compound 168 (Ex. 9), Compound 348 (Ex. 10), Compound 483 (Ex. 11) and Compound 598 (Ex. 12) were used as dopants in the EML instead of Compound 369, respectively.

[0580] Comparative Example (Ref): OLED Manufacturing

[0581] An OLED was fabricated using the same procedure and the same materials as in Example 1, except that the following PD was used as a dopant in the EML instead of Compound 369.

[0582]

[0583] Experimental Example 2: Measuring the Light Emitting Performance of OLED

[0584] The 9 mm 2 Each OLED with a certain emission area was connected to an external power supply, and the luminescence performance of all OLEDs was evaluated at room temperature using a constant current power supply (KEITHLEY) and a photometer PR650. In particular, at 10 mA / cm 2 The driving voltage (V), external quantum efficiency (EQE, relative value) and the time period (T) from the initial brightness to 95% of the brightness were measured at the current density. 95 The measurement results are shown in Table 1 below.

[0585] Table 1: Light-emitting properties of OLEDs

[0586]

[0587] As shown in Table 1, compared with the OLED manufactured in the comparative example, the OLED in which the organometallic compound according to the present disclosure is applied as a dopant has its driving voltage reduced by 9.7% and its external quantum efficiency (EQE) and T 95 The increases were 17% and 52%, respectively. These results indicate that by applying the organometallic compound of the present disclosure to the EML, the OLED can reduce its driving voltage and significantly improve its luminous efficiency and luminous lifetime.

[0588] It is obvious to those skilled in the art that various modifications and variations can be made in the present disclosure without departing from the scope of the present invention. Therefore, the present disclosure is intended to cover modifications and variations of the present disclosure if they are within the scope of the appended claims.

Claims

1. An organometallic compound having a structure of Chemical Formula 8 or Chemical Formula 9: [Chemical Formula 8] [Chemical Formula 9] Wherein, M is molybdenum (Mo), tungsten (W), rhenium (Re), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt) or silver (Ag); R is unsubstituted or substituted C 1 -C 20 -alkyl, unsubstituted or substituted C 1 -C 20 -alkylsilyl, unsubstituted or substituted C 4 -C 30 -alicyclic group, unsubstituted or substituted C 3 -C 30 -heteroalicyclic group, unsubstituted or substituted C 6 -C 30 -aryl, or unsubstituted or substituted C 3 -C 30 -heteroaryl; X 21 to X 27 each independently is CR 1 or N; Y 3 is BR 2 、CR 2 R 3 、C=O、SiR 2 R 3 、GeR 2 R 3 、P=O、O、S、SO 2 、SeO 2 、Te or TeO 2 、or NR a wherein, R a is unsubstituted or substituted C 1 -C 20 alkyl, or unsubstituted or substituted C 6 -C 30 aryl; R 1 to R 3 each independently is protium, deuterium, tritium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, an unsubstituted or substituted C 1 -C 20 alkyl, an unsubstituted or substituted C 2 -C 20 alkenyl, an unsubstituted or substituted C 2 -C 20 alkynyl, an unsubstituted or substituted C 1 -C 20 alkoxy, an amino group, an unsubstituted or substituted C 1 -C 20 alkylamino, an unsubstituted or substituted C 1 -C 20 alkylsilyl, a carboxyl group, a nitrile group, an isonitrile group, a thioalkyl group, a phosphino group, an unsubstituted or substituted C 4 -C 30 alicyclic group, an unsubstituted or substituted C 3 -C 30 heteroalicyclic group, an unsubstituted or substituted C 6 -C 30 aryl, or an unsubstituted or substituted C 3 -C 30 heteroaryl, Optionally, Two adjacent carbons linked to R 1 and / or R 2 With R 3 Form an unsubstituted or substituted C 4 -C 30 alicyclic, unsubstituted or substituted C 3 -C 30 heteroalicyclic, unsubstituted or substituted C 6 -C 30 aromatic ring, or unsubstituted or substituted C 3 -C 30 heteroaromatic ring; R 11 to R 13 each independently is protium, deuterium, tritium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, an unsubstituted or substituted C 1 -C 20 alkyl, an unsubstituted or substituted C 2 -C 20 alkenyl, an unsubstituted or substituted C 2 -C 20 alkynyl, an unsubstituted or substituted C 1 -C 20 alkoxy, an amino group, an unsubstituted or substituted C 1 -C 20 alkylamino, an unsubstituted or substituted C 1 -C 20 alkylsilyl, a carboxyl group, a nitrile group, an isonitrile group, a thioalkyl group, a phosphino group, an unsubstituted or substituted C 4 -C 30 alicyclic group, an unsubstituted or substituted C 3 -C 30 heteroalicyclic group, an unsubstituted or substituted C 6 -C 30 aryl, or an unsubstituted or substituted C 3 -C 30 heteroaryl; m is an integer from 1 to 3; n is an integer from 0 to 2; m + n is the oxidation number of M, Among them, the substituents in the term "substituted" are selected from unsubstituted or halogen-substituted C 1 -C 20 alkyl, unsubstituted or halogen-substituted C 1 -C 20 alkoxy, halogen, cyano, -CF 3 3, hydroxyl, carboxyl, carbonyl, amino, C 1 -C 10 alkylamino, C 6 -C 30 arylamino, C 3 -C 30 heteroarylamino, C 6 -C 30 aryl, C 3 -C 30 heteroaryl, nitro, carbohydrazide, sulfonate, C 1 -C 20 alkylsilyl, C 6 -C 30 arylsilyl and C 3 -C 30 heteroarylsilyl.

2. The organometallic compound according to claim 1, Wherein, The organometallic compound is selected from the following compounds:

3. The organometallic compound according to claim 1, Wherein, The organometallic compound is selected from the following compounds:

4. An organic light-emitting device, Comprising: A substrate; And An organic light-emitting diode on the substrate, the organic light-emitting diode comprising: A first electrode; A second electrode facing the first electrode; and A light-emitting layer disposed between the first electrode and the second electrode and comprising at least one light-emitting material layer, Wherein, the at least one light-emitting material layer contains the organometallic compound having a structure of Chemical Formula 8 or Chemical Formula 9 according to claim 1.

5. The organic light-emitting device according to claim 4, Wherein, The at least one light-emitting material layer contains a matrix and a dopant, and the dopant contains the organometallic compound.

6. The organic light-emitting device according to claim 4, Wherein, The at least one light-emitting material layer includes a first light-emitting material layer and a second light-emitting material layer; The light-emitting layer includes: A first light-emitting portion disposed between the first electrode and the second electrode and including the first light-emitting material layer; A second light-emitting portion disposed between the first light-emitting portion and the second electrode and including the second light-emitting material layer; and A first charge generation layer disposed between the first light-emitting portion and the second light-emitting portion, Wherein, at least one of the first light-emitting material layer or the second light-emitting material layer contains the organometallic compound.

7. The organic light-emitting device according to claim 6, Wherein, The second light-emitting material layer includes: A lower light-emitting material layer disposed between the first charge generation layer and the second electrode; and An upper light-emitting material layer disposed between the lower light-emitting material layer and the second electrode, Wherein, one of the lower light-emitting material layer or the upper light-emitting material layer contains the organometallic compound, and Wherein, the light-emitting layer further includes: A third light-emitting portion disposed between the second light-emitting portion and the second electrode and including a third light-emitting material layer; and A second charge generation layer disposed between the second light-emitting portion and the third light-emitting portion.

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