Organic light-emitting diode containing a metal-organic compound and various types of host materials, and organic light-emitting diode indicator device

Abstract

In one example, an organic light-emitting diode contains an emission material layer comprising a metal-organic compound and various types of host materials. Furthermore, a display device using organic light-emitting diodes is discussed.

Description

BACKGROUND OF THE INVENTION Area of ​​the invention

[0001] The present invention relates to an organic light-emitting diode comprising a metal-organic compound and various types of host materials. Description of the related technique

[0002] Interest in display devices is increasing, and their application is found in various fields. One type of display device that is rapidly developing is organic light-emitting diode (OLED) technology.

[0003] An OLED is an element that emits the energy of excitons as light after electrons and holes have paired to form excitons when charges are injected into an emissive material layer formed between an anode and a cathode. Compared to conventional display technologies, OLEDs can be operated at a low voltage, consume relatively little power, deliver excellent color reproduction, can be applied to a flexible substrate for diverse applications, and allow for display devices to be freely sized.

[0004] Compared to liquid crystal displays (LCDs), OLEDs offer a wide viewing angle and high contrast ratio, and they do not require backlighting, making them lightweight and ultra-thin. OLEDs are formed by arranging a variety of intermediate layers, such as a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron barrier layer, an electron transport layer, an electron injection layer, and the like, between the cathode (electron injection electrode) and the anode (hole injection electrode).

[0005] In the OLED structure, when a voltage is applied between two electrodes, electrons and holes are injected from the cathode and the anode, respectively, and the excitons generated by the emission material layer fall into a ground state and emit light.

[0006] The organic materials used in OLEDs can be broadly divided into a light-emitting material and a charge-transport material. The light-emitting material is a crucial factor in determining the luminous efficacy of the OLED and should exhibit high quantum efficiency and excellent electron and hole mobility, as well as be uniformly and permanently present in the emission layer. Light-emitting materials are categorized into blue, red, and green, depending on the color of the light emitted. They are used as host materials and dopants to enhance color purity and increase luminous efficacy through energy transfer.

[0007] While in fluorescent materials only a singlet of about 25% of the excitons formed in the emission material layer is used to generate light and a triplet of 75% is mostly lost as heat, phosphorescent materials have a luminescence mechanism that converts both the singlet and the triplet into light.

[0008] To date, organometallic compounds have been used as phosphorescent materials in OLEDs. There remains a technical need to improve OLED performance by deriving highly efficient phosphorescent dopants and using host materials with optimal photophysical properties to enhance the efficiency and lifetime of the device compared to conventional OLEDs.

[0009] US 2023 / 0138288A1 discloses a heteroleptic compound of the formula Ir(L a ) m (L B ) n , where La and L B Specific ligands are used that provide coordination of the Ir by a 5-membered ring and a 6-membered ring. Furthermore, the use of this compound as a doping material in OLEDs is disclosed.

[0010] US 2023 / 0146148A1 discloses organometallic compounds containing a first ligand L a This includes compounds based on a structure of fused five- and six-membered rings, and their various uses, including as emitters in devices. Formulations containing these compounds are also provided. Furthermore, organic light-emitting devices (OLEDs) and related consumer products that utilize these compounds are presented.

[0011] DE 10 2022 134 162 A1 discloses an organometallic compound used as a doping material in the light-emitting layer of an organic light-emitting diode (OLED). An organic light-emitting device comprises the OLED and can be a display device or a lighting device. It is stated that the use of the organometallic compound results in an improved color gamut of the diode, luminous efficiency, and lifetime, as well as a lower operating voltage for the diode. SUMMARY OF THE INVENTION

[0012] Therefore, the present invention is directed to provide an organic light-emitting diode (OLED) in which a metal-organic compound and various types of host materials, which are able to improve the operating voltage, efficiency and lifetime, are applied to an organic emission material layer.

[0013] The objectives of the present invention are not limited to the one described above, and other objectives and advantages of the present invention not mentioned here can be understood from the following description and will become clearer with reference to embodiments of the present invention. Furthermore, it can be readily seen that the objectives and advantages of the present invention can be achieved by means and combinations of the present invention described in the claims.

[0014] To achieve the objective, an embodiment of the present invention can provide an organic light-emitting diode comprising a first electrode, a second electrode facing the first electrode, and an intermediate layer arranged between the first electrode and the second electrode, wherein the intermediate layer comprises an emission material layer, and wherein the emission material layer comprises a dopant material and a host material, the dopant material comprising a metal-organic compound represented by chemical formula 1 below, and the host material comprising a mixture of a compound represented by chemical formula 4 below and a compound represented by chemical formula 5 below: M(L A ) m (L B ) n <Chemische Formel 1> in chemical formula 1, M is a central coordination metal, selected from the group consisting of molybdenum (Mo), tungsten (W), rhenium (Re), ruthenium (Ru), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt) and gold (Au), is L A a ligand represented by the chemical formula 2, is L B a bidentate ligand, is m 1, 2 or 3, is n 0, 1 or 2, and is (m+n) the oxidation number of the central coordination metal M, in chemical formula 2, A has selected a ring structure consisting of substituted or unsubstituted pyridine and substituted or unsubstituted pyrimidine, R1 to R8 are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; and a substituted or unsubstituted C4-C20 bicycloalkyl group, and R1 to R8 are optionally partially or completely deuterated. R9 is in each case independently selected at least one from the group consisting of hydrogen, deuterium; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; a C3-C20 cycloalkyl group; halogen; a nitrile group; a substituted or unsubstituted C1-C20 alkoxy group; and combinations thereof, and R9 is optionally partially or completely deuterated, and is, if any of R1 to R9 is substituted, a substituent of R1 to R9 is each independently selected from the group consisting of deuterium; halogen; a C3-C10 cycloalkyl group; and combinations thereof, and, if a plurality of the substituents of R1 to R9 are present, each substituent is the same or different from each other, Y is at least one selected from the group consisting of BR 10 ; CR 10 R 11 ; C=O; CNR 10 ; SiR 10 R 11 ; NR 10 ; PR 10 ; AsR 10 ; SbR 10 ; P(O)R 10 ; P(S)R 16 ; P(Se)R 10 ; As(O)R 10 ; As(S)R 10 ; As(Se)R 10 ; Sb(O)R 10 ; Sb(S)R 10 ; Sb(Se)R 10 ; O; S; Se; Te; SO; SO2; SeO; SeO2; TeO; and TeO2, X1 to X4 are each independently selected from CR 12 and nitrogen (N), and are, if any two adjacent X1 to X4 are CR 12 are two R 12 not bound or bound by forming a 5- or 6-membered, substituted or unsubstituted aromatic ring or a heteroaromatic ring structure, and is, if any two of X1 to X4 are adjacent, CR 12 is and the other nitrogen (N) is, R 12 not bound or bound to the nitrogen to form a 5-membered or 6-membered heteroaromatic ring structure, and is the aromatic ring or heteroaromatic ring structure that is formed when R 12 is bound, not or substituted with at least one deuterium, are R 10 to R 12each independently selected at least one from the group consisting of hydrogen; deuterium; halogen; a hydroxyl group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C1-C20 heteroalkyl group; a substituted or unsubstituted C7-C20 arylalkyl group; a substituted or unsubstituted C2-C20 alkenyl group; a substituted or unsubstituted C3-C20 cycloalkenyl group; a substituted or unsubstituted C2-C20 heteroalkenyl group; a substituted or unsubstituted C2-C20 alkynyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group;a substituted or unsubstituted C1-C20 alkoxy group; an amino group; a silyl group; a C2-C30 acyl group; a carboxyl group; a nitrile group; an isonitrile group; a sulfanyl group; and a phosphino group, and; is when one of the residues R 10 to R 12 is substituted, a substituent of R 10 to R 12 each independently at least one selected from the group consisting of deuterium, halogen and combinations thereof, and is, if several of the substituents of R 10 to R 12 are present, each substituent being the same or different from each other, is p at least 2, and The dashed line represents a connection position to the central coordination metal M, in chemical formula 4, Ar is each independently a divalent group of an aromatic ring or a heteroaromatic ring, selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran and dibenzothiophene, Ar1 and Ar2 are each independently a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C2-C60 heteroaryl group, are R 21-1 to R 21-4each independently selected at least one from the group consisting of deuterium; halogen; a hydroxyl group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C1-C20 heteroalkyl group; a substituted or unsubstituted C7-C20 arylalkyl group; a substituted or unsubstituted C2-C20 alkenyl group; a substituted or unsubstituted C3-C20 cycloalkenyl group; a substituted or unsubstituted C2-C20 heteroalkenyl group; a substituted or unsubstituted C2-C20 alkynyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group; a substituted or unsubstituted C1-C20 alkoxy group; an amino group; a silyl group;a C2-C30 acyl group; a carboxyl group; a nitrile group; an isonitrile group; a sulfanyl group; and a phosphino group; is an integer from 0 to 3, and if o is an integer of 2 or 3, then R 21-1 same or different and, if necessary, partially or completely deuterated is an integer from 0 to 4, and if s is an integer from 2 to 4, then R 21-2 same or different and, if necessary, partially or completely deuterated is an integer from 0 to 4, and if t is an integer from 2 to 4, then R 21-3 same or different and, if applicable, R 21-3 partially or fully deuterated is an integer from 0 to 4, and if u is an integer from 2 to 4, then R 21-4 same or different and, if necessary, partially or completely deuterated is an integer from 0 to 2, and is an integer of 0 or 1, and is a linker L of at least one selected from the group consisting of a substituted or unsubstituted C6-C30 arylene group; a substituted or unsubstituted C2-C30 heteroarylene group; and a substituted or unsubstituted C7-C20 arylalkylene group, in chemical formula 5, A B-ring is a substituted or unsubstituted monocyclic or polycyclic aromatic condensed C6-C30 ring, are X 11 and X 12 , each independently of each other, N or CR', L1 is selected from the group consisting of a single bond; a substituted or unsubstituted C6-C30 arylene group; a substituted or unsubstituted C2-C30 heteroarylene group; and a substituted or unsubstituted C3-C30 cycloalkylene group. Ar3 is selected from the group consisting of hydrogen; deuterium; halogen; a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group; and an -L 24 -SiR k R1R m group, where L 24 a single bond, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroarylene group, where R k , R1 and R m each independently being hydrogen, a substituted or unsubstituted C1-C30 alkyl group or a substituted or unsubstituted C6-C30 aryl group, wherein one or more of the hydrogens are an alkyl group, an aryl group, a heteroaryl group or a group -L 24 -SiR k R1R m, which is Ar3, unsubstituted or substituted with one or more deuterium and halogen atoms, Z is selected from the group consisting of the following structures W is selected from the group consisting of O, S, and NR. 31 ; CR 31 R 32 ; and SiR 31 R 32 , are R 22 to R 32and R' each independently selected from the group consisting of hydrogen; deuterium; halogen; a hydroxyl group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C1-C20 heteroalkyl group; a substituted or unsubstituted C7-C20 arylalkyl group; a substituted or unsubstituted C2-C20 alkenyl group; a substituted or unsubstituted C3-C20 cycloalkenyl group; a substituted or unsubstituted C2-C20 heteroalkenyl group; a substituted or unsubstituted C2-C20 alkynyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group; a substituted or unsubstituted C1-C20 alkoxy group; an amino group; a silyl group;a C2-C30 acyl group; a carboxyl group; a nitrile group; an isonitrile group; a sulphanyl group; and a phosphino group, and; a, c, e and i are each independently an integer of 1, 2, 3 or 4; b, d, g are each independently an integer of 1, 2 or 3; f is an integer of 1, 2, 3, 4, 5 or 6; and h is an integer of 1, 2, 3, 4 or 5.

[0015] In another aspect, the present invention can provide an organic light-emitting diode comprising a first electrode, a second electrode facing the first electrode, and one or more light-emitting parts arranged between the first electrode and the second electrode, wherein at least one of the light-emitting parts comprises a red phosphorescent layer, the red phosphorescent layer comprises a dopant material and a host material, the dopant material comprises a metal-organic compound represented by chemical formula 1 below, and the host material comprises a compound represented by chemical formula 4 below, and additionally comprises a compound represented by chemical formula 5 below, and the definitions of chemical formulas 1, 4, and 5 are the same as in an embodiment of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS Fig. Figure 1 is a cross-sectional view schematically showing an organic light-emitting diode (OLED) according to one or more embodiments of the present invention. Fig. Figure 2 is a cross-sectional view schematically showing the OLED with a tandem structure having two light-emitting parts according to one or more embodiments of the present invention. Fig. Figure 3 is a cross-sectional view schematically showing the OLED with a tandem structure having three light-emitting parts according to one or more embodiments of the present invention. Fig. Figure 4 is a cross-sectional view schematically showing an OLED display device onto which the OLED is applied according to one or more embodiments of the present invention. DETAILED DESCRIPTION OF THE EXECUTION FORMS

[0016] If the description uses terms such as "include," "consist of," "arrange," "provide," and the like, other parts may be added unless "only" is used. If a component is mentioned in the singular, this includes cases where multiple components are present, unless explicitly stated otherwise.

[0017] When designing a component in the description, the component is designed to include the error margin, even if no separate explicit description is provided. All components of each display device and each OLED according to all embodiments of the present invention are functionally coupled and configured.

[0018] In the description, the arrangement of any component on an "upper section (or a lower section)" of a component or "above (or below)" the component can mean not only that the component is in contact with an upper surface (or a lower surface) of the component, but also that other components can be inserted between the component and the component that is arranged above (or below) the component.

[0019] The term "halo" or "halogen" used here includes fluorine, chlorine, bromine and iodine.

[0020] The term "alkyl group" as used here refers to both linear and branched alkyl groups. Unless otherwise specified, the linear alkyl group contains 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The branched alkyl group contains 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The alkyl group can be methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, tert-pentyl, neopentyl, 3-pentyl, and the like, and can additionally be substituted as desired.

[0021] The term "cycloalkyl group" used here refers to cyclic alkyl groups. Unless otherwise specified, the cycloalkyl group contains 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, and comprises cyclopropyl, cyclopentyl, cyclohexyl and the like, and may additionally be substituted as desired.

[0022] The term "alkenyl group" used here refers to both linear and branched alkene residues. Unless otherwise specified, the alkenyl group contains 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms, and the alkenyl group can also be arbitrarily substituted.

[0023] The term "cycloalkenyl group" used here refers to cyclic alkenyl groups. Unless otherwise specified, the cycloalkenyl group contains 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, and the cycloalkenyl group can also be arbitrarily substituted.

[0024] The term "alkynyl group" used here refers to both linear and branched alkyne residues. Unless otherwise specified, the alkynyl group contains 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms. Furthermore, the alkynyl group can be arbitrarily substituted.

[0025] The term "cycloalkynyl group" used here refers to cyclic alkynyl residues. Unless otherwise specified, the cycloalkynyl group contains 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, and may additionally be substituted as desired.

[0026] The terms “aralkyl group” or “arylalkyl group” used here are interchangeable and refer to an alkyl group with an aromatic group as a substituent, and unless otherwise specified, the aralkyl group contains 7 to 60 carbon atoms, preferably 7 to 40 carbon atoms, more preferably 7 to 20 carbon atoms, and additionally the aralkyl group may be substituted arbitrarily.

[0027] The terms "aryl group," "aromatic group," "aromatic ring," "aromatic carbocyclic ring," and "aromatic heterocyclic ring" used herein can include conjugated structures, single rings, and polycyclic rings. The polycyclic ring can comprise a "condensed ring," i.e., two or more rings in which two carbon atoms are shared by two adjacent rings. Unless otherwise specified, the aryl group contains 5 to 60 carbon atoms, and the aryl group can be arbitrarily substituted, for example, by one or more further aryl groups with 6 to 12 carbon atoms. Preferably, the aryl group, aromatic group, aromatic ring, aromatic carbocyclic ring, or aromatic heterocyclic ring contains 5 to 40 carbon atoms, and particularly preferably 5 to 20 carbon atoms.The aryl group, aromatic group, aromatic ring, aromatic carbocyclic ring or aromatic heterocyclic ring can be phenyl, or, if it is a polycyclic ring, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran and dibenzothiophene.

[0028] Unless otherwise stated, the term ‘carbon cyclic ring group’ used herein can be interpreted as encompassing all ‘cycloalkyl groups’, ‘cycloalkenyl groups’ and ‘cycloalkynyl groups’ that are alicyclic ring groups, as well as ‘aryl groups’ that are aromatic ring groups.

[0029] The term “heterocyclic ring group” used here means that one or more of the carbon atoms forming an aryl group, a cycloalkyl group, a cycloalkenyl group, a cycloalkynyl group, an aralkyl group (arylalkyl group), an arylamino group and the like are substituted with a heteroatom, such as oxygen (O), nitrogen (N), sulfur (S), etc., and, with reference to the above definition, comprise a heteroaryl group, a heterocycloalkyl group, a heterocycloalkenyl group, a heterocycloalkynyl group, a heteroarylalkyl group (heteroarylalkyl group), a heteroarylamino group and the like, and, unless otherwise specified, the heteroaryl group contains 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms, particularly preferably 2 to 20 carbon atoms, and additionally the heterocyclic ring group may be arbitrarily substituted.

[0030] The terms “heteroalkyl group”, “heteroalkenyl group”, “heteroalkynyl group” and “heteroaralkyl group (heteroarylalkyl group)” used here mean that one or more of the carbon atoms forming the respective “alkyl group”, “alkenyl group”, “alkynyl group” and “aralkyl group (arylalkyl group)” are substituted with heteroatoms such as oxygen (O), nitrogen (N) and sulfur (S), and additionally the heteroalkyl group, the heteroalkenyl group, the heteroalkynyl group and heteroaralkyl group (heteroarylalkyl group) can be substituted arbitrarily.

[0031] The terms "alkylamino group", "aralkylamino group", "arylamino group" and "heteroarylamino group" used here mean that the amine group is substituted with the alkyl group, the aralkyl group, the aryl group and the heteroaryl group, which is a heteroring, and include all primary, secondary and tertiary amines, and additionally the alkylamino group, the aralkylamino group, the arylamino group and the heteroarylamino group can be substituted arbitrarily.

[0032] The terms "alkylsilyl group", "arylsilyl group", "alkoxy group", "aryloxy group", "alkylthio group" and "arylthio group" mean that the silyl group, the oxy group or the thio group is each substituted with the alkyl group and the aryl group, respectively, and additionally the alkylsilyl group, the arylsilyl group, the alkoxy group, the aryloxy group, the alkylthio group and the arylthio group can be substituted arbitrarily.

[0033] The term “substituted” means that instead of the hydrogen atom (H) bonded to the carbon atom, another substituent is bonded to the corresponding carbon atom, and in the case of “substituted” one or more substituents are used, and if a multitude of substituents are present, each substituent can be the same or different from the others.

[0034] Unless otherwise specified herein, the substituent(s) in the case of "substituted" may be at least one selected from the group consisting of deuterium, halogen, C1-C20 alkyl, C3-C30 cycloalkyl, C1-C20 heteroalkyl, C2-C30 heterocycloalkyl, C7-C30 arylalkyl, C1-C20 alkoxy, C6-C30 aryloxy, amino, silyl, C1-C20 alkylsilyl, C6-C20 arylsilyl, C7-C20 alkylarylsilyl, C2-C20 alkenyl, C3-C20 cycloalkenyl, C2-C20 heteroalkenyl, C2-C20 alkynyl, C6-C30 aryl, C2-C30 heteroaryl, C2-C20 acyl, carboxyl, nitrile, isonitrile, sulfanyl, phosphino, phenyl, dibenzofuran and combinations thereof, and includes a case in which at least one hydrogen of the substituents is substituted with deuterium, which may be the case, for example, if the substituent is partially or completely deuterated. Preferably, the substituent is deuterium.

[0035] The term “combinations thereof” in the definition of a substituent indicates that multiple substituents may be present, and the multitude of substituents is defined as a combination from the defined list.

[0036] The substituents mentioned here that are not defined above follow the definitions of the known substituents.

[0037] A case in which two substituents, defined as containing hydrogen, are joined to form a ring, includes, within the scope of the present disclosure, a case in which one of the two substituents is hydrogen and the other is not hydrogen, and the hydrogen is removed while the two substituents are joined.

[0038] Within the context of the present disclosure, the term “deuterated” can mean substitution with deuterium instead of light hydrogen in a compound.

[0039] Within the scope of this disclosure, the term “bidentate ligand” can refer to a ligand with two coordination sites that can simultaneously bind to a metal atom such as iridium. In some embodiments, the bidentate ligand comprises bidentate carboxylate, bidentate amine, bidentate thiocarboxylate, bidentate diphosphine, bidentate mercaptopyrimidine, or bidentate dithiocarboxylate.

[0040] Unless otherwise stated herein, a position to be substituted is not limited as long as it is a position in which a hydrogen atom is substituted, e.g. a position in which a substituent can be substituted, and if two or more substituents are present, the substituents can be the same or different.

[0041] The objects and substituents defined here can be the same or different, unless otherwise specified.

[0042] The structure of a metal-organic compound and an organic light-emitting diode (OLED) containing this compound according to the present invention are described in detail below.

[0043] Conventionally, organometallic compounds have been used as dopants in phosphorescent layers, and structures such as 2-phenylpyridine are known as major ligand structures of these compounds. However, since conventional light-emitting dopants have limitations in increasing the efficiency and lifetime of OLEDs, it is necessary to develop new light-emitting dopants. The present invention has been completed by experimentally confirming that by mixing a hole-transport-type host material and an electron-transport-type host material together with the dopant, the efficiency and lifetime of the OLED can be further increased and the operating voltage reduced, thereby improving the properties of the OLED.

[0044] According to one embodiment of the present invention, an organic light-emitting diode is provided comprising the following: a first electrode; a second electrode opposite the first electrode; and an intermediate layer that is arranged between the first electrode and the second electrode, wherein the intermediate layer contains an emission material layer and the emission material layer contains a doping material and a host material,

[0045] The doping material is a metal-organic compound represented by, or comprising, the chemical formula 1 below.

[0046] The host material is or comprises a mixture of a compound of chemical formula 4 below and a compound of chemical formula 5. M(LA) m (La) n <Chemische Formel 1> In chemical formula 1 M is a central coordination metal, selected from the group consisting of molybdenum (Mo), tungsten (W), rhenium (Re), ruthenium (Ru), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt) and gold (Au), is L A a ligand represented by the chemical formula 2, is L B a bidentate ligand, is m 1, 2 or 3, is n 0, 1 or 2, and is (m+n) the oxidation number of the central coordination metal M, in chemical formula 2 A has a ring structure, selected from substituted or unsubstituted pyridine and substituted or unsubstituted pyrimidine, R1 to R8 are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; and a substituted or unsubstituted C4-C20 bicycloalkyl group, and are optionally partially or completely deuterated. R9 is in each case independently selected at least one from the group consisting of hydrogen, deuterium; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; a C3-C20 cycloalkyl group; halogen; a nitrile group; a substituted or unsubstituted C1-C20 alkoxy group; and combinations thereof, and R9 is optionally partially or completely deuterated. is, if one of the residues R1 to R9 is substituted, a substituent of R1 to R9 is each independently selected from the group consisting of deuterium, halogen, a C3-C10 cycloalkyl group and combinations thereof, and, if a plurality of the substituents of R1 to R9 are present, each substituent is the same or different from each other, Y is at least one selected from the group consisting of BR 10 ; CR 10 R 11 ; C=O; CNR 10 ; SiR 10 R 11 ; NR 10 ; PR 10 ; AsR 10 ; SbR 10 ; P(O)R 10 ; P(S)R 16 ; P(Se)R 10 ; As(O)R 10 ; As(S)R 16 ; As(Se)R 10 ; Sb(O)R 10 ; Sb(S)R 10 ; Sb(Se)R 10 ; O; S; Se; Te; SO; SO2; SeO; SeO2; TeO; and TeO2, X1 to X4 are each independently at least one selected from CR 12 and nitrogen (N), are, if any two adjacent X1 to X4 are CR 12 are two R 12 not bound or bound by forming a 5- or 6-membered, substituted or unsubstituted aromatic ring or a heteroaromatic ring structure, and is, if any two of X1 to X4 are adjacent, CR 12 is and the other nitrogen (N) is, R 12 not bound or bound to the nitrogen to form a 5-membered or 6-membered heteroaromatic ring structure, and is the aromatic ring or heteroaromatic ring structure that is formed when R 12 is bound, not or substituted with at least one deuterium, are R 10 to R 12each independently selected at least one from the group consisting of hydrogen; deuterium; halogen; a hydroxyl group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C1-C20 heteroalkyl group; a substituted or unsubstituted C7-C20 arylalkyl group; a substituted or unsubstituted C2-C20 alkenyl group; a substituted or unsubstituted C3-C20 cycloalkenyl group; a substituted or unsubstituted C2-C20 heteroalkenyl group; a substituted or unsubstituted C2-C20 alkynyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group;a substituted or unsubstituted C1-C20 alkoxy group; an amino group; a silyl group; a C2-C30 acyl group; a carboxyl group; a nitrile group; an isonitrile group; a sulfanyl group; and a phosphino group; is when one of the residues R 10 to R 12 is substituted, a substituent of R 10 to R 12 each independently at least one selected from the group consisting of deuterium, halogen and combinations thereof, and is, if several of the substituents of R 10 to R 12 are present, each substituent being the same or different from each other, and is p equal to 2, and and the dashed line represents a connection position to the central coordination metal M, in chemical formula 4, Ar, each independently of the others, is a divalent group of an aromatic ring or a heteroaromatic ring, selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran and dibenzothiophene, Ar1 and Ar2 are each independently a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C2-C60 heteroaryl group, are R 21-1 to R 21-4each independently selected at least one from the group consisting of deuterium; halogen; a hydroxyl group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C1-C20 heteroalkyl group; a substituted or unsubstituted C7-C20 arylalkyl group; a substituted or unsubstituted C2-C20 alkenyl group; a substituted or unsubstituted C3-C20 cycloalkenyl group; a substituted or unsubstituted C2-C20 heteroalkenyl group; a substituted or unsubstituted C2-C20 alkynyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group; a substituted or unsubstituted C1-C20 alkoxy group; an amino group; a silyl group;a C2-C30 acyl group; a carboxyl group; a nitrile group; an isonitrile group; a sulfanyl group; and a phosphino group; is an integer from 0 to 3, and if o is an integer of 2 or 3, then R 21-1 same or different and, if necessary, partially or completely deuterated is an integer from 0 to 4, and if s is an integer from 2 to 4, then R 21-2 same or different and, if necessary, partially or completely deuterated is an integer from 0 to 4, and if t is an integer from 2 to 4, then R 21-3 same or different and, if necessary, partially or completely deuterated is an integer from 0 to 4, and if u is an integer from 2 to 4, then R 21-4 same or different and, if necessary, partially or completely deuterated is an integer from 0 to 2, and is an integer of 0 or 1, and is a linker L of at least one selected from the group consisting of a substituted or unsubstituted C6-C30 arylene group; a substituted or unsubstituted C2-C30 heteroarylene group; and a substituted or unsubstituted C7-C20 arylalkylene group, in chemical formula 5, A B-ring is a substituted or unsubstituted monocyclic or polycyclic aromatic condensed C6-C30 ring, are X 11 and X 12 each independently of each other N or CR' L1 is selected from the group consisting of a single bond; a substituted or unsubstituted C6-C30 arylene group; a substituted or unsubstituted C2-C30 heteroarylene group; and a substituted or unsubstituted C3-C30 cycloalkylene group. Ar3 is selected from the group consisting of hydrogen; deuterium; halogen; a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group; and -L 24 -SiR k R1R m , where L 24 a single bond is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heteroarylene group, and R k , R l and R m , each independently of each other are hydrogen, a substituted or unsubstituted C1-C30 alkyl group or a substituted or unsubstituted C6-C30 aryl group, wherein one or more hydrogens of an alkyl group, an aryl group, a heteroaryl group or an -L 24 -SiR k R l R mGroup that is Ar3, unsubstituted or substituted with one or more deuterium and halogen atoms, Z is selected from the group consisting of the following structures W is selected from the group consisting of O, S, and NR. 31 ; CR 31 R 32 ; and SiR 31 R 32 , are R 22 to R 32and R' each independently selected from the group consisting of hydrogen, deuterium; halogen; a hydroxyl group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C1-C20 heteroalkyl group; a substituted or unsubstituted C7-C20 arylalkyl group; a substituted or unsubstituted C2-C20 alkenyl group; a substituted or unsubstituted C3-C20 cycloalkenyl group; a substituted or unsubstituted C2-C20 heteroalkenyl group; a substituted or unsubstituted C2-C20 alkynyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group; a substituted or unsubstituted C1-C20 alkoxy group; an amino group; a silyl group;a C2-C30 acyl group; a carboxyl group; a nitrile group; an isonitrile group; a sulfanyl group; and a phosphine group, and ; a, c, e and i are each independently an integer of 1, 2, 3 or 4; b, d, g are each independently an integer of 1, 2 or 3; f is an integer of 1, 2, 3, 4, 5 or 6; and h is an integer of 1, 2, 3, 4 or 5.

[0047] In one embodiment, the host material can comprise two types of compounds represented by chemical formula 4 and one type of compound represented by chemical formula 5. In other words, the host material can contain a mixture of a first compound of chemical formula 4, a second compound of chemical formula 4, and a compound of chemical formula 5.

[0048] According to a preferred embodiment of the present invention, an organic light-emitting diode is provided comprising the following: a first electrode; a second electrode opposite the first electrode; and an intermediate layer that is arranged between the first electrode and the second electrode, wherein the intermediate layer contains an emission material layer and the emission material layer contains a doping material and a host material, wherein the doping material contains a metal-organic compound of chemical formula 1 below and the host material contains a mixture of a compound of chemical formula 4 below and a compound of chemical formula 5 below. M(LA) m (La) n <Chemische Formel 1> In chemical formula 1, M is a key coordination metal and is iridium (Ir), is L A a ligand represented by the chemical formula 2, is L B a bidentate ligand, is m 2, is n 1, and is (m+n) the oxidation number of the central coordination metal M, in chemical formula 2, A has a ring structure, selected from substituted or unsubstituted pyridine and substituted or unsubstituted pyrimidine, R1 to R8 are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted linear C1-C10 alkyl group; R9 is in each case independently selected at least one from the group consisting of hydrogen; deuterium; a substituted or unsubstituted linear C1-C10 alkyl group; a substituted or unsubstituted branched C3-C10 alkyl group; and combinations thereof. is, if one of the residues R1 to R9 is substituted, a substituent of R1 to R9 is each independently selected from the group consisting of deuterium, halogen, a C3-C10 cycloalkyl group and combinations thereof, and, if several substituents of R1 to R9 are present, each substituent is the same or different from each other, Y is at least one element from the group consisting of O, S and Se, are X1 to X4 CR 12 , where, if necessary, two R 12 are bound to any adjacent X1 to X4 to form a 5- or 6-membered, substituted or unsubstituted aromatic ring, and is the aromatic ring that is formed where R 12 bound, not substituted, or substituted with at least one deuterium, are R 12each independently selected at least one from the group consisting of hydrogen; deuterium; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; a substituted or unsubstituted C6-C30 aryl group; and a substituted or unsubstituted C2-C30 heteroaryl group, is when one of the residues R 12 is substituted, a substituent independently of at least one selected from the group consisting of deuterium, halogen and combinations thereof, and is, if several of the substituents of R 12 are present, each substituent being the same or different from the others, and is p equal to 2, and The dashed line represents a connection position to the central coordination metal M, in chemical formula 4, Ar is each independently a divalent group of an aromatic ring, selected from the group consisting of benzene, naphthalene and phenanthrene, Ar1 and Ar2 are each independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group, are R 21-1 to R 21-4 each independently selected at least one from the group consisting of deuterium, halogen, a substituted or unsubstituted C1-C10 alkyl group and a substituted or unsubstituted C6-C20 aryl group, is an integer from 0 to 1, and is R 21-1 possibly partially or completely deuterated s is an integer from 0 to 2, preferably from 0 to 1, and R is 21-2 possibly partially or completely deuterated is an integer from 0 to 2, preferably from 0 to 1, and is R21-3 possibly partially or completely deuterated is an integer from 0 to 2, preferably from 0 to 1, and is R 21-4 possibly partially or completely deuterated q is an integer from 0 to 1 and is an integer of 0 or 1, and Linker L is at least one selected from the group consisting of a substituted or unsubstituted C6-C30 arylene group; a substituted or unsubstituted C2-C30 heteroarylene group; and a substituted or unsubstituted C7-C20 arylalkylene group, in chemical formula 5, B is a substituted or unsubstituted monocyclic or polycyclic aromatic condensed C6-C20 ring, are X 11 and X 12 each independently of each other N or CR' L1 is selected from the group consisting of a single bond and a substituted or unsubstituted C6-C10 arylene group, Ar3 is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; and -L 24 -SiR k R l R m , where L 24 a single bond or a substituted or unsubstituted C6-C20 arylene group, and R k , R1 and R m each independently consists of hydrogen, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, wherein one or more of the hydrogens of an alkyl group, an aryl group, a heteroaryl group or a group -L 24 -SiR k R l R m, which is Ar3, unsubstituted or substituted with one or more deuterium and halogen atoms, Z is selected from the group consisting of the following structures W is selected from the group consisting of O, S, and NR. 31 ; and CR 31 R 32 , are R 22 to R 32 and R' each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted C1-C10 alkyl group and a substituted or unsubstituted C6-C20 aryl group, and ai are each independently an integer of 1 or 2.

[0049] According to a more preferred embodiment of the present invention, an organic light-emitting diode is provided, comprising: a first electrode; a second electrode opposite the first electrode; and an intermediate layer that is arranged between the first electrode and the second electrode, wherein the intermediate layer contains an emission material layer and the emission material layer contains a doping material and a host material, wherein the doping material includes or consists of a metal-organic compound of chemical formula 1 below, and the host material contains or consists of a mixture of a compound represented by chemical formula 4 below and a compound represented by chemical formula 5. M(LA) m (La) n <Chemische Formel 1>

[0050] In chemical formula 1, M is a key coordination metal and is iridium (Ir), is L A a ligand represented by the chemical formula 2, is L B a bidentate ligand, is m 2, is n 1, and is (m+n) the oxidation number of the central coordination metal M, in chemical formula 2, A has a ring structure, selected from substituted or unsubstituted pyridine and substituted or unsubstituted pyrimidine, where, if A is substituted, the substituent is deuterium, R1 to R8 are each independently at least one from the group consisting of hydrogen and an optionally deuterated C1 alkyl group, R9 is in each case independently at least one of the group consisting of hydrogen, an optionally deuterated C1 alkyl group, an optionally deuterated branched C3-C5 alkyl group and combinations thereof, Y is at least one element from the group consisting of O, S and Se, are X1 to X4 CR 12 where two R 12are bound to any adjacent X1 to X4, optionally forming a 6-membered, optionally deuterated, aromatic ring, are R 12 each independently of each other at least one from the group consisting of hydrogen or an unsubstituted branched C3-C5 alkyl group, and is p equal to 2, and The dashed line represents a connection position to the central coordination metal M, in chemical formula 4, Ar is each independently a divalent group of an aromatic ring selected from the group consisting of benzene and naphthalene, Ar1 and Ar2 are each independently substituted or unsubstituted phenyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted dibenzofuranyl; and substituted or unsubstituted dibenzothiophenyl, are R 21-1 to R 21-4each independently selecting at least one group from the group consisting of halogen, a substituted or unsubstituted C1-C5 alkyl group and a substituted or unsubstituted C6 aryl group, is an integer from 0 to 1, and is R 21-1 possibly partially or completely deuterated is an integer from 0 to 1, and is R 21-2 possibly partially or completely deuterated is an integer from 0 to 1, and is R 21-3 possibly partially or completely deuterated is u an integer from 0 to 1, and is R 21-4 possibly partially or completely deuterated q is an integer from 0 to 1 and is an integer from 0, and Linker L is at least one selected from the group consisting of a substituted or unsubstituted C6-C30 arylene group, in chemical formula 5, B is a substituted or unsubstituted monocyclic C6 ring or a substituted or unsubstituted polycyclic aromatic condensed C10 ring, are X 11 and X 12 N, L1 is selected from the group consisting of a single bond and a substituted or unsubstituted C6-C10 arylene group, Ar3 is selected from the group consisting of hydrogen; a substituted or unsubstituted C1-C5 alkyl group; and a substituted or unsubstituted C6-C10 aryl group; and -L 24 -SiR k R l R m , where L 24 a single bond or a substituted or unsubstituted C6 arylene group, and R k , R l and R m each is a substituted or unsubstituted C6-C10 aryl group, wherein one or more of the hydrogens of an alkyl group, an aryl group, a heteroaryl group or a group -L 24 -SiR k R l R m , which is Ar3, unsubstituted or substituted with one or more deuterium and halogen atoms, Z is selected from the group consisting of the following structures, W is selected from the group consisting of O, S, and NR. 31 ; and CR 31 R 32 , are R 22 to R 32 and R' each independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1-C5 alkyl group and a substituted or unsubstituted C6-C20 aryl group, and ai are each independently an integer of 1 or 2.

[0051] In one embodiment of the present invention, some or all of the compounds of chemical formula 1, the compounds of chemical formula 4, or the compounds of chemical formula 5 may be deuterated.

[0052] In one embodiment of the present invention, the organometallic compound represented by chemical formula 1 can have a homoleptic or heteroleptic structure, for example a homoleptic structure in which n is 0, a heteroleptic structure in which n is 1, or a heteroleptic structure in which n is 2, and n can for example be 2.

[0053] In one embodiment of the present invention, n in chemical formula 1 can be any of the integers from 0 to 2, and n can be, for example, 2.

[0054] In one embodiment of the present invention, m in the chemical formula 1 can be one or more, e.g. an integer from 1 to 3, and e.g. an integer from 1 or 2.

[0055] In chemical formula 1, if m is 2 or 3, or if n is 2, several substituents represented by the same symbol can be the same or different from each other.

[0056] In some embodiments, L B The chemical formula 1 contains an electron donor unit that functions as an electron donor auxiliary ligand. L B As an electron donor auxiliary ligand, it can increase the electron density of the central coordination metal M in chemical formula 1, thereby reducing the energy of the MLCT (metal-ligand charge transfer) and the contribution ratio of 3MLCT is increased to state T1. As a result, the organic light-emitting diode containing the metal-organic compound represented by chemical formula 1 can achieve improved light-emitting properties such as high luminous efficacy and high external quantum efficiency.

[0057] In some embodiments, L B in chemical formula 1 by at least one structure selected from the group consisting of chemical formula 3-1 and chemical formula 3-2 below: in chemical formula 3-1 and chemical formula 3-2, Z3 to Z5 are each independently selected from the group consisting of hydrogen, deuterium; halogen; a hydroxyl group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C1-C20 heteroalkyl group; a substituted or unsubstituted C7-C20 arylalkyl group; a substituted or unsubstituted C2-C20 alkenyl group; a substituted or unsubstituted C3-C20 cycloalkenyl group; a substituted or unsubstituted C2-C20 heteroalkenyl group; a substituted or unsubstituted C2-C20 alkynyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group;a substituted or unsubstituted C1-C20 alkoxy group; an amino group; a silyl group; a C2-C30 acyl group; a carboxyl group; a nitrile group; an isonitrile group; a sulfanyl group; and a phosphino group; Z6 and Z7 are each independently selected from the group consisting of oxygen (O) and NR. z , and is R z each independently selected from the group consisting of hydrogen, a linear C1-C20 alkyl group and a substituted or unsubstituted branched C3-C20 alkyl group, is R z preferably isopropylene and The dashed line represents a connection position to the central coordination metal M.

[0058] In some embodiments, Z3 and Z5 can have the same structure. In some embodiments, at least one of Z3 or Z5 can be an unsubstituted branched C4 alkyl group, an unsubstituted branched C5 alkyl group, or an unsubstituted branched C6 alkyl group. In some embodiments, Z6 and Z7 can have the same structure. In some embodiments, at least one of Z6 or Z7 can be NR z be, and R z Z4 can be an isobutyl or isopropyl group. In some embodiments, Z4 can be an isobutyl or isopropyl group.

[0059] In one embodiment, the compound represented by chemical formula 1 can be represented by a structure selected from the group consisting of chemical formula 1-1-(1), chemical formula 1-1-(2), chemical formula 1-1-(3), chemical formula 1-1-(4), chemical formula 1-1-(5) and chemical formula 1-1-(6); the compound represented by chemical formula 1-2 can be represented by a structure selected from the group consisting of chemical formula 1-2-(1), chemical formula 1-2-(1), chemical formula 1-2-(2), chemical formula 1-2-(3), chemical formula 1-2-(4), chemical formula 1-2-(5) and chemical formula 1-2-(6); and the compound represented by chemical formula 1-3 can be represented by a structure selected from the group consisting of chemical formula 1-3-(1), chemical formula 1-3-(2), chemical formula 1-3-(3), of the chemical formula 1-3-(4),of the chemical formula 1-3-(5) and the chemical formula 1-3-(6),

[0060] In the chemical formula 1-1-(1), the chemical formula 1-1-(2), the chemical formula 1-1-(3), the chemical formula 1-1-(4), the chemical formula 1-1-(5), the chemical formula 1-1-(6), the chemical formula 1-2-(1), the chemical formula 1-2-(2), the chemical formula 1-2-(3), the chemical formula 1-2-(4), the chemical formula 1-2-(5), the chemical formula 1-2-(6), the chemical formula 1-3-(1), the chemical formula 1-3-(2), the chemical formula 1-3-(3), the chemical formula 1-3-(4), the chemical formula 1-3-(5), and the chemical formula 1-3-(6), M, X1 to X4, Y, R1 to R9, p, m and n are as defined in chemical formula 1, and Z3 to Z7 are as defined in chemical formula 3-1 and chemical formula 3-2.

[0061] In one embodiment of the present invention, A in chemical formula 2 can have a pyridine ring structure.

[0062] In one embodiment of the present invention, M can be iridium (Ir) in chemical formula 1.

[0063] In one embodiment of the present invention, Y in chemical formula 2 can be one of the elements oxygen (O), sulfur (S) and selenium (Se).

[0064] In one embodiment of the present invention, at least one of the R9 groups in chemical formula 2 cannot be hydrogen; in other words, at least one of the R9 groups in chemical formula 2 excludes hydrogen. Put another way, at least one of the R9 groups in chemical formula 2 can be selected from the group consisting of deuterium; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; a C3-C20 cycloalkyl group; a halogen; a nitrile group; a substituted or unsubstituted C1-C20 alkoxy group; and combinations thereof.

[0065] In one embodiment of the present invention, R 10 to R 12in chemical formula 2, at least one of the following is selected independently from the group consisting of hydrogen; deuterium; halogen; a nitrile group; a nitro group; a substituted or unsubstituted C1-C20 alkoxy group; an amino group; a substituted or unsubstituted linear C1-C10 alkyl group; a substituted or unsubstituted branched C3-C10 alkyl group; and a substituted or unsubstituted C3-C10 cycloalkyl group.

[0066] According to one embodiment of the present invention, the organometallic compound represented by chemical formula 1 can be one of the following compounds RD-1 to RD-20, but is not limited to them, as long as it is included in the definition of chemical formula 1.

[0067] In one embodiment of the present invention, in chemical formula 4, Ar1 and Ar2 each independently comprise a monovalent group selected from the group consisting of substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted spirobifluorene, and at least one hydrogen atom in one of Ar1 and Ar2 may be substituted with at least one selected from the group consisting of deuterium; a halogen atom; a C1-C10 alkyl group; a C6-C20 aryl group; a C2-C20 heteroaryl group; a nitrile group; a silyl group; and combinations thereof.

[0068] In one embodiment of the present invention, the compound represented by chemical formula 4 can be, and is not limited to, a compound selected from the group consisting of the following compounds RHH-1 to RHH-20, as long as it falls within the definition of chemical formula 4.

[0069] In one embodiment of the present invention, the chemical formula 5 X 11 and X 12 N be.

[0070] In one embodiment of the present invention, the compound represented by chemical formula 5 can be selected from the group consisting of the following compounds REH-1 to REH-20, and is not limited thereto, as long as it falls within the definition of chemical formula 5.

[0071] In particular, according to one embodiment of the present invention, an organic light-emitting diode 100 can be provided comprising a first electrode 110, a second electrode 120 facing the first electrode 110, and an intermediate layer 130 arranged between the first electrode 110 and the second electrode 120 (see Fig. 1) The intermediate layer 130 can contain an emission material layer 160, the emission material layer 160 can contain a doping material 160' and host materials 160'' and 160''' and can contain the metal-organic compound 160' represented by chemical formula 1 below as a doping material, and the host material can contain two types of compound 160'' represented by chemical formula 4 below as a hole-transport type host and compound 160''' represented by chemical formula 5 below as an electron-transport type host.

[0072] Furthermore, in the organic light-emitting diode 100, the intermediate layer 130, which is arranged between the first electrode 110 and the second electrode 120, can have a structure comprising a hole injection layer (HIL) 140, a hole transport layer (HTL) 150, the emission material layer (EML) 160, an electron transport layer (ETL) 170, and an electron injection layer (EIL) 180, sequentially from the first electrode 110. The second electrode 120 can be formed on the electron injection layer 180, and a protective film can also be formed on the second electrode 120.

[0073] As in Fig. As shown in Figure 1, one or more hole transport auxiliary layers and electron barrier layers can also be inserted between the hole transport layer 150 and the emission material layer 160.

[0074] The hole transport auxiliary layer can contain a compound with good hole transport properties and adjust the hole injection characteristic by reducing the HOMO energy level difference between the hole transport layer 150 and the emission material layer 160, thereby reducing the accumulation of holes at the interface between the hole transport auxiliary layer and the emission material layer 160. This reduces the quenching phenomenon, which refers to the annihilation of excitons by polarons at the interface. Consequently, it reduces the degradation phenomenon of the element, thereby stabilizing the element and increasing its efficiency and lifetime.

[0075] The electron barrier layer can prevent electrons from entering the hole transport layer by regulating electron movement and recombination with holes, thus increasing the efficiency and lifetime of the OLED. A material forming the electron barrier layer can be selected from 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, mCP, mCBP, CuPC, DNTPD, TDAPB, DCDPA, 2,8-Bis(9-phenyl-9H-carbazol-3-yl)dibenzo[b,d]thiophene, and similar materials. Furthermore, the electron barrier layer can contain an inorganic compound.The inorganic compound can be selected from halide compounds such as LiF, NaF, KF, RbF, CsF, FrF, MgF2, CaF2, SrF2, BaF2, LiCl, NaCl, KCl, RbCl, CsCl and FrCl, and oxides such as Li2O, Li2O2, Na2O, K2O, Rb2O, Rb2O2, Cs2O, Cs2O2, LiAlO2, LiBO2, LiTaO3, LiNbO3, LiWO4, Li2CO, NaWO4, KAlO2, K2SiO3, B2O5, Al2O3, and SiO2, but is not necessarily limited to them.

[0076] The first electrode 110 can be an anode and can be made of ITO, IZO, tin oxide or zinc oxide, which is a conductive material with a relatively high work function value, but is not limited to this.

[0077] The second electrode 120 can be a cathode and can contain Al, Mg, Ca, Ag or an alloy or combination thereof, which is a conductive material with a relatively low work function value, but is not limited to this.

[0078] The hole injection layer 140 can be arranged between the first electrode 110 and the hole transport layer 150. The hole injection layer 140 can serve to improve the interfacial properties between the first electrode 110 and the hole transport layer 150 and can be selected as a material with suitable conductivity. The hole injection layer 140 can contain a compound such as MTDATA, CuPc, TCTA, HATCN, TDAPB, PEDOT / PSS, or N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine), preferably N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine), but this is not limited to N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine).

[0079] The hole transport layer 150 can be arranged adjacent to the emission material layer between the first electrode 110 and the emission material layer 160. The hole transport layer 150 can contain, but is not limited to, a compound such as TPD, NPB, CBP, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine or N-biphenyl-4-yl)-N-4-9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl)-4-amine, preferably NPB.

[0080] According to one embodiment of the present invention, the emission material layer 160 can be doped with the metal-organic compound represented by chemical formula 1 as dopant 160' to increase the light yield and the like of the hosts 160'' and 160''' and of the entire element, and the dopant 160' can be used as a material that emits green or red light and can be used, for example, as a red phosphorescent material.

[0081] According to one embodiment of the present invention, the doping concentration of the dopant 160' can be set in the range of 1 to 30 wt.%, based on the total weight of the host species 160" and 160"', and is not limited thereto, but for example the doping concentration can be 2 to 20 wt.%, for example 3 to 15 wt.%, for example 5 to 10 wt.%, for example 3 to 8 wt.%, for example 2 to 7 wt.%, for example 5 to 7 wt.% and for example 5 to 6 wt.%.

[0082] According to one embodiment of the present invention, the mixing ratio of the two types of hosts 160'' and 160''' is not particularly limited, and host 160'', which is the compound represented by chemical formula 4, can exhibit hole transport properties, and host 160''', which is the compound represented by chemical formula 5, can exhibit electron transport properties. Therefore, when the two types of hosts are mixed, it is possible to increase the lifetime properties, and the mixing ratio of the two types of hosts can be adjusted accordingly.Therefore, the mixing ratio of the two hosts in which the compound represented by chemical formula 4 and the compound represented by chemical formula 5 are mixed is not particularly limited, and the ratio (based on weight) of the compound represented by chemical formula 4 and the compound represented by chemical formula 5 may, for example, be in the range of 1:9 to 9:1, for example 2:8, for example 3:7, for example 4:6, for example 5:5, for example 6:4, for example 7:3 and for example 8:2.

[0083] Furthermore, the electron transport layer 170 and the electron injection layer 180 can be stacked sequentially between the emission material layer 160 and the second electrode 120. The electron transport layer material must have high electron mobility, and electrons can be stably supplied to the emission material layer via smooth electron transport.

[0084] The material of the electron transport layer 170 is commonly used in engineering and can, for example, comprise a compound such as Alq3 (tris(8-hydroxyquinolino)aluminium), Liq(8-hydroxyquinolinolatolithium), PBD(2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4oxadiazole), TAZ(3-(4-biphenyl)4-phenyl-5-tert-butylphenyl-1,2,4-triazole), Spiro-PBD, BAlq(bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminium), SAlq, TPBi(2,2',2-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole), oxadiazole, triazole, phenanthroline, benzoxazole, benzthiazole, or 2-(4-(9,10-Di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, preferably 2-(4-(9,10-Di(naphthalen)-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, but is not limited to this.

[0085] The electron injection layer 180 serves to enable the smooth injection of electrons, and a material for the electron injection layer is commonly used in the industry and can include, for example, Alq3 (tris(8-hydroxyquinolino)aluminium), PBD, TAZ, spiro-PBD, BAlq, SAlq, or similar materials, but is not limited to these. Alternatively, the electron injection layer 180 can be made from a metal compound, and the metal compound can include, for example, Liq, LiF, NaF, KF, RbF, CsF, FrF, BeF2, MgF2, CaF2, SrF2, BaF2, RaF2, or similar materials, but is not limited to these.

[0086] The OLED according to the present invention can be a white OLED with a tandem structure. In the tandem OLED according to one embodiment of the present invention, a single light-emitting stack (or light-emitting part) can be formed in a structure in which two or more light-emitting stacks (or light-emitting parts) are connected by the charge-generating layer CGL. The OLED can contain two or more light-emitting stacks (light-emitting parts) comprising a first and a second electrode facing each other on the substrate, and the emissive material layer arranged between the first and second electrodes to emit light in a specific wavelength band. The multiple light-emitting stacks (light-emitting parts) can be configured to emit the same color or different colors.Furthermore, a light-emitting stack (light-emitting part) can contain one or more layers of emissive material, and the multiple light-emitting layers can be light-emitting layers of the same color or of different colors.

[0087] In this case, one or more of the emission material layers contained in the plurality of light-emitting parts can contain the metal-organic compound represented by chemical formula 1 according to the present invention as a dopant. The plurality of light-emitting parts in the tandem structure can be connected to the charge-generating layer CGL, which is formed from an N-type charge-generating layer and a P-type charge-generating layer.

[0088] Accordingly, another aspect of the present invention provides an organic light-emitting diode comprising: a first electrode; a second electrode opposite the first electrode; and one or more light-emitting parts arranged between the first electrode and the second electrode, wherein at least one of the light-emitting parts contains a red phosphorescent layer, The red phosphorescent layer contains a doping material and a host material. the doping material contains the organometallic compound represented by chemical formula 1, and The host material contains a mixture of the compound represented by chemical formula 4 and the compound represented by chemical formula 5. In other words, in one embodiment of the present invention, the intermediate layer can comprise one or more light-emitting parts, and the emissive material layer can be a layer in at least one of the one or more light-emitting parts and can be a red phosphorescent layer.

[0089] Detailed descriptions of the first electrode, the second electrode, the organometallic compound represented by chemical formula 1, the compound represented by chemical formula 4, and the compound represented by chemical formula 5 are as described above.

[0090] The OLED can have a structure in which a multitude of light-emitting parts are present between the first electrode and the second electrode, and the light-emitting parts are connected by charge-generating layers that are arranged between the multitude of light-emitting parts.

[0091] Fig. 2 and Fig. Figure 3, which shows one or more embodiments of the present invention, are cross-sectional views that schematically depict OLEDs in tandem structures with two or three light-emitting parts.

[0092] As in Fig.As shown in Figure 2, the organic light-emitting diode 100 of the present invention comprises the first electrode 110 and the second electrode 120, which are opposite each other, and an intermediate layer 230, which is arranged between the first electrode 110 and the second electrode 120. The intermediate layer 230 comprises a first light-emitting part ST1, which is arranged between the first electrode 110 and the second electrode 120 and contains a first emissive material layer 261, a second light-emitting part ST2, which is arranged between the first light-emitting part ST1 and the second electrode 120 and contains a second emissive material layer 262, and the charge-generating layer CGL, which is arranged between the first and second light-emitting parts ST1 and ST2. The charge-generating layer CGL can contain an N-type charge-generating layer 291 and a P-type charge-generating layer 292.One or more of the first emission material layer 261 and the second emission material layer 262 can contain the metal-organic compound represented by chemical formula 1 according to the present invention as a dopant 262'. As in . Fig. As shown in Figure 2, for example, the second emission material layer 262 of the second light-emitting part ST2 can contain the compound 262' represented by chemical formula 1 as a dopant, a compound 262'' represented by chemical formula 4 as a hole-transport-type host, and a compound 262''' represented by chemical formula 5 as an electron-transport-type host. With reference to Fig. 2. Each of the first and second light-emitting parts ST1 and ST2 can contain an additional emission material layer besides the first emission material layer 261 and the second emission material layer 262. The above refers to the hole transport layer 150. Fig.The contents described in section 1 can be transferred to the first hole transport layer 251 and the second hole transport layer 252 of Fig. 2 can be applied in the same or a similar manner. Furthermore, the above regarding the electron transport layer 170 can be applied. Fig. 1 described contents on the first electron transport layer 271 and the second electron transport layer 272 of Fig. 2. applied in the same or a similar manner.

[0093] As in Fig.As shown in Figure 3, the organic light-emitting diode 100 of the present invention comprises the first electrode 110 and the second electrode 120, which are opposite each other, and an intermediate layer 330, which is arranged between the first electrode 110 and the second electrode 120. The intermediate layer 330 comprises the first light-emitting part ST1, which is arranged between the first electrode 110 and the second electrode 120 and contains the first emission material layer 261, the second light-emitting part ST2, which contains the second emission material layer 262, a third light-emitting part ST3, which contains a third emission material layer 263, a first charge-generating layer CGL1, which is arranged between the first and second light-emitting parts ST1 and ST2, and a second charge-generating layer CGL2, which is arranged between the second and third light-emitting parts ST2 and ST3.The first and second charge-generating layers CGL1 and CGL2 can comprise the N-charge-generating layers 291 and 293, respectively, and the P-charge-generating layers 292 and 294. One or more of the first emission material layer 261, the second emission material layer 262, and the third emission material layer 263 can contain the organometallic compound represented by chemical formula 1 according to the present invention as a dopant. As in . Fig. As shown in Figure 3, for example, the second emission material layer 262 of the second light-emitting part ST2 can contain the compound 262' represented by chemical formula 1 as a dopant, the compound 262'' represented by chemical formula 4 as a host for the hole transport type, and the compound 262''' represented by chemical formula 5 as a host for the electron transport type. With reference to Fig.3 In addition to the first emission material layer 261, the second emission material layer 262, and the third emission material layer 263, each of the first, second, and third light-emitting parts ST1, ST2, and ST3 can be formed as a plurality of emission material layers by including an additional emission material layer. The above refers to the hole transport layer 150. Fig. The contents described in section 1 can be applied to the first hole transport layer 251, the second hole transport layer 252, and the third hole transport layer 253 of Fig. 3 can be applied in the same or a similar manner. Furthermore, the above regarding the electron transport layer 170 can be applied. Fig. 1 described contents on the first electron transport layer 271, the second electron transport layer 272 and the third electron transport layer 273 of Fig. 3. applied in the same or a similar manner.

[0094] Furthermore, according to an embodiment of the present invention, the OLED can have a tandem structure in which four or more light-emitting parts and three or more charge-generating layers are arranged between the first electrode and the second electrode.

[0095] The OLED according to the invention can be used in OLED display devices and lighting devices with OLEDs.

[0096] According to one embodiment of the present invention, an organic light-emitting diode display device is provided, comprising the following: a substrate; a drive element that is arranged on the substrate; and the organic light-emitting diode, which is arranged on the substrate and connected to the drive element.

[0097] In one embodiment, Fig.4 a cross-sectional view which schematically shows an OLED display device onto which the OLED is applied according to an embodiment of the present invention.

[0098] As in Fig. As shown in Figure 4, an OLED display device 3000 can comprise a substrate 3010, an OLED 4000, and an encapsulation film 3900 covering the OLED 4000. A driving thin-film transistor Td, which is a driving element, and the OLED 4000, which is connected to the driving thin-film transistor Td, are arranged on the substrate 3010. The OLED display device 3000 comprises a variety of the components shown in Figure 4. Fig. The configuration shown in section 4 consists of a multitude of OLEDs 4000 and associated thin-film transistors Td. Other components for displaying images by the OLED display device 3000 are included therein.

[0099] Although in Fig.Not explicitly shown in Figure 4, substrate 3010 further comprises a gate line and a data line that intersect to define a pixel area, a power supply line that is spaced apart from the gate line or the data line and extends parallel to it, a switching thin-film transistor connected to the gate line and the data line, and a storage capacitor connected to the power supply line and an electrode of the switching thin-film transistor.

[0100] The driving thin-film transistor Td is connected to the switching thin-film transistor and comprises a semiconductor layer 3100, a gate electrode 3300, a source electrode 3520 and a drain electrode 3540.

[0101] The semiconductor layer 3100 can be formed on the substrate 3010 and can consist of an oxide semiconductor material or polycrystalline silicon. If the semiconductor layer 3100 consists of the oxide semiconductor material, a light-blocking pattern can optionally be formed beneath the semiconductor layer 3100. This light-blocking pattern prevents light from reaching the semiconductor layer 3100, thus preventing light-induced degradation of the semiconductor layer 3100. Alternatively, the semiconductor layer 3100 can consist of polycrystalline silicon, in which case both edges of the semiconductor layer 3100 can be doped with impurities.

[0102] A gate insulating film 3200 made of an insulating material is formed on the entire surface of the substrate 3010 and the semiconductor layer 3100. The gate insulating film 3200 can consist of an inorganic insulating material, e.g., silicon oxide or silicon nitride.

[0103] A gate electrode 3300 made of a conductive material, such as a metal, is formed above the gate insulating film 3200 in the center of the semiconductor layer 3100. The gate electrode 3300 is connected to the switching thin-film transistor.

[0104] An insulating interlayer 3400 made of an insulating material is formed on the entire surface of the substrate 3010 and the gate electrode 3300. The interlayer insulating film 3400 can be made of an inorganic insulating material, such as silicon oxide or silicon nitride, or of an organic insulating material, such as benzocyclobutene or photoacrylic.

[0105] The interlayer insulating film 3400 has first and second semiconductor layer contact holes 3420 and 3440, which expose both sides of the semiconductor layer 3100. The first and second semiconductor layer contact holes 3420 and 3440 are arranged such that they are spaced apart from the gate electrode 3300 on both sides of the gate electrode 3300.

[0106] The source electrode 3520 and the drain electrode 3540, which consist of the conductive material, such as a metal, are formed on the insulating intermediate layer 3400. The source electrode 3520 and the drain electrode 3540 are arranged so that they are spaced apart from each other with respect to the gate electrode 3300 and are in contact with both sides of the semiconductor layer 3100 via the first and second semiconductor layer contact holes 3420 and 3440, respectively. The source electrode 3520 is connected to the current conductor.

[0107] The semiconductor layer 3100, the gate electrode 3300, the source electrode 3520 and the drain electrode 3540 form the control thin-film transistor Td, and the control thin-film transistor Td has a coplanar structure in which the gate electrode 3300, the source electrode 3520 and the drain electrode 3540 are arranged over the semiconductor layer 3100.

[0108] Alternatively, the driving thin-film transistor Td can have an inverted, staggered structure, in which the gate electrode is located below the semiconductor layer and the source and drain electrodes are located above the semiconductor layer. In this case, the semiconductor layer can be made of amorphous silicon. Meanwhile, the switching thin-film transistor can have essentially the same structure as the controlling thin-film transistor Td.

[0109] Simultaneously, the OLED display device 3000 can incorporate a color filter 3600 that absorbs the light generated by the OLED 4000. For example, the color filter 3600 can absorb light in the colors red (R), green (G), blue (B), and white (W). In this case, red, green, and blue color filter patterns that absorb light can be formed separately in each pixel area, and each of the color filter patterns can be arranged to overlap each intermediate layer 4300 of the OLED 4000 that emits light in a wavelength band to be absorbed. By using the color filter 3600, the OLED display device 3000 can display full color.

[0110] If, for example, the OLED display device 3000 is of a bottom-emission type, the color filter 3600, which absorbs light, can be arranged above the insulating intermediate layer 3400, which corresponds to the OLED 4000. In an embodiment where the OLED display device 3000 is of an top-emission type, the color filter can be positioned above the OLED 4000, for example, above a second electrode 4200. The color filter 3600 can, for example, be shaped to have a thickness of 2 to 5 µm.

[0111] Meanwhile, a planarization layer 3700 with a drain contact hole 3720, which exposes the drain electrode 3540 of the driver thin-film transistor Td, is formed to cover the driver thin-film transistor Td.

[0112] On the planarization layer 3700, a first electrode 4100 is formed separately in each pixel area, which is connected to the drain electrode 3540 of the thin-film transistor Td via the drain contact hole 3720.

[0113] The first electrode 4100 can be an anode and be made of a conductive material with a relatively high work function value. For example, the first electrode 4100 can be made of a transparent conductive material such as ITO, IZO, or ZnO.

[0114] If the OLED display device 3000 is a top-emitting device, a reflective electrode or a reflective layer can be formed under the first electrode 4100. For example, the reflective electrode or the reflective layer can be made of aluminum (Al), silver (Ag), nickel (Ni), or an aluminum-palladium-copper alloy (APC).

[0115] A bank layer 3800, covering an edge of the first electrode 4100, is formed on the planarization layer 3700. The bank layer 3800 exposes the center of the first electrode 4100, which corresponds to the pixel area.

[0116] The intermediate layer 4300 is formed on the first electrode 4100, and if required, the OLED 4000 can have a tandem structure, and with regard to the tandem structure, reference is made to the Fig. Reference is made to Figures 2 to 4, which show the embodiment of the present invention and the above description thereof.

[0117] The second electrode 4200 is formed above the substrate 3010, on which the intermediate layer 4300 is formed. The second electrode 4200 can be positioned anywhere on the surface of the display area and can be made of a conductive material with a relatively low work function value to serve as the cathode. For example, the second electrode 4200 can be made of aluminum (Al), magnesium (Mg), or an aluminum-magnesium alloy (Al-Mg).

[0118] The first electrode 4100, the intermediate layer 4300 and the second electrode 4200 form the OLED 4000.

[0119] The encapsulation film 3900 is formed on the second electrode 4200 to prevent moisture from penetrating the OLED 4000 from the outside. Although in Fig.Not explicitly shown in Figure 4, the encapsulation film 3900 can have a three-layer structure in which a first inorganic layer, an intermediate layer and an inorganic layer are stacked on top of each other, but is not limited to this.

[0120] Examples of the present invention are described below. However, the following examples are only examples of the present invention, and the present invention is not limited to them. EXAMPLES

[0121] The following examples are not to be understood as limiting. The invention above offers many different embodiments for implementing its features, and the following examples describe specific embodiments. It is understood that other modifications and methods known to those skilled in the art can also be applied to the following experimental procedures without exceeding the scope of the invention. Example 1

[0122] An ITO substrate was cleaned with UV ozone prior to use and then loaded into a deposition system. The substrate was then transported to a vacuum deposition chamber where all subsequent layers were deposited over the substrate. The following layers were deposited in the following sequence by deposition from a heated boat under a vacuum of approximately 10 -7 Torr is isolated.

[0123] HATCN (see structure below) was thermally deposited in a vacuum onto a provided transparent ITO electrode as a hole injection material to form a 100 Å thick hole injection layer. Then, HTL (see structure below) was thermally deposited in a vacuum as a hole transport material to form a 700 Å thick hole transport layer. Subsequently, an emission material layer 300 Å thick was formed using RD6 as the dopant and a mixture of RHH1 and REH1 (RHH1:REH1 = 1:1, based on weight) as the host. The dopant concentration in the emission material layer was 10 wt%.Subsequently, an OLED with a structure consisting of ITO / hole injection layer / hole transport layer / emission material layer / electron transport layer / electron injection layer / cathode was fabricated by sequentially thermally depositing Alq3 (see structure below) as the electron transport material and LiF as the electron injection material in a vacuum to form an electron transport layer 300 Å thick and an electron injection layer 10 Å thick, and then depositing aluminum 1000 Å thick to form a cathode. After deposition, the layers were transferred from the deposition chamber to a drying box to form a film and subsequently encapsulated with a UV-cured epoxy and a moisture collector. Examples 2 to 144 and comparative examples 1 to 4

[0124] The OLEDs of Comparative Examples 1 to 4 and Examples 2 to 144 were fabricated in the same manner as in Example 1, except that the dopant materials and host materials listed in Tables 1 to 8 were used in Example 1. In Examples 2 to 144, the mixing ratio of the host materials was 1:1 (by weight). In Comparative Examples 1 to 4, the "CBP" type with the structure shown below was used as the host for the emission material layer.

[0125] The materials used in examples 1 to 144 and comparison examples 1 to 4 are as follows. Experimental example

[0126] The OLEDs produced in examples 1 to 144 and comparison examples 1 to 4 had an emission area of ​​9 mm². 2Each OLED was connected to an external power source, and the device characteristics were investigated at room temperature using a power source (KEITHLEY) and a photometer (PR 650); the results are listed in Tables 1 to 8. When a DC voltage was applied, the light emission was confirmed to have the characteristics specified in Tables 1 to 8.

[0127] In particular, the characteristic values ​​for the operating voltage (V), the external quantum efficiency (EQE) and the lifetime (LT95) were determined at a current of 10 mA / cm². 2 measured, and the measured values ​​of examples 1 to 144 were calculated as relative values ​​(percentage, %) for each of the comparison examples 1 to 4, and the results are listed in Tables 1 to 8 below.

[0128] The LT95 lifetime indicates the time an OLED needs to reach its full lifespan at 40 °C and 40 mA / cm². 2to lose 5% of their original brightness (lifespan decreases from 100% to 95%). LT95 is the most difficult specification to meet for element characteristics, and LT95 can be used to determine whether an OLED will suffer from image burn-in. [Table 1] Emission material layer Operating voltage (V) EQE(%,relative value) LT95(%,relative value) Doping material Host material Comparative example 1 RD6 CBP 4.30 100 100 Example 1 RD6 RHH1 REH1 4.15 125 145 Example 2 RD6 RHH1 REH2 4.14 127 143 Example 3 RD6 RHH1 REH3 4.10 120 130 Example 4 RD6 RHH1 REH4 4.09 119 130 Example 5 RD6 RHH1 REH5 4.11 119 130 Example 6 RD6 RHH1 REH6 4.10 120 133 Example 7 RD6 RHH2 REH1 4.13 123 143 Example 8 RD6 RHH2 REH2 4.12 125 140 Example 9 RD6 RHH2 REH3 4.09 118 130 Example 10 RD6 RHH2 REH4 4.10 117 131 Example 11 RD6 RHH2 REH5 4.10 116 132 Example 12 RD6 RHH2 REH6 4.11 119 130 Example 13 RD6 RHH3 REH1 4.15 125 140 Example 14 RD6 RHH3 REH2 4.13 125 135 Example 15 RD6 RHH3 REH3 4.10 120 130 Example 16 RD6 RHH3 REH4 4.11 117 130 Example 17 RD6 RHH3 REH5 4.10 115 132 Example 18 RD6 RHH3 REH6 4.10 120 130 [Table 2] Emission material layer EQE LT95 Doping material Host material Operating voltage (V) (%,relative value) (%,relative value) Comparative example 1 RD6 CBP 4.30 100 100 Example 19 RD6 RHH4 REH1 4.20 125 150 Example 20 RD6 RHH4 REH2 4.18 125 135 Example 21 RD6 RHH4 REH3 4.15 123 135 Example 22 RD6 RHH4 REH4 4.15 120 130 Example 23 RD6 RHH4 REH5 4.10 120 135 Example 24 RD6 RHH4 REH6 4.12 120 133 Example 25 RD6 RHH5 REH1 4.14 123 130 Example 26 RD6 RHH5 REH2 4.15 120 125 Example 27 RD6 RHH5 REH3 4.13 119 120 Example 28 RD6 RHH5 REH4 4.12 118 120 Example 29 RD6 RHH5 REH5 4.11 117 122 Example 30 RD6 RHH5 REH6 4.11 119 117 Example 31 RD6 RHH6 REH1 4.15 115 130 Example 32 RD6 RHH6 REH2 4.16 115 125 Example 33 RD6 RHH6 REH3 4.18 113 115 Example 34 RD6 RHH6 REH4 4.15 114 120 Example 35 RD6 RHH6 REH5 4.14 115 125 Example 36 RD6 RHH6 REH6 4.13 116 123 [Table 3] Emission material layer Operating voltage (V) EQE(%,relative value) LT95(%,relative value) Doping material Host material Comparative example 2 RD11 CBP 4.32 100 100 Example 37 RD11 RHH1 REH1 4.22 115 150 Example 38 RD11 RHH1 REH2 4.20 116 148 Example 39 RD11 RHH1 REH3 4.18 113 135 Example 40 RD11 RHH1 REH4 4.19 115 135 Example 41 RD11 RHH1 REH5 4.15 116 135 Example 42 RD11 RHH1 REH6 4.15 115 138 Example 43 RD11 RHH2 REH1 4.15 120 148 Example 44 RD11 RHH2 REH2 4.17 119 145 Example 45 RD11 RHH2 REH3 4.14 115 135 Example 46 RD11 RHH2 REH4 4.15 115 136 Example 47 RD11 RHH2 REH5 4.15 113 137 Example 48 RD11 RHH2 REH6 4.14 115 135 Example 49 RD11 RHH3 REH1 4.15 115 145 Example 50 RD11 RHH3 REH2 4.17 117 140 Example 51 RD11 RHH3 REH3 4.20 118 135 Example 52 RD11 RHH3 REH4 4.15 116 135 Example 53 RD11 RHH3 REH5 4.18 115 137 Example 54 RD11 RHH3 REH6 4.18 115 135 [Table 4] Emission material layer Operating voltage (V) EQE(%,relative value) LT95(%,relative value) Doping material Host material Comparative example 2 RD11 CBP 4.32 100 100 Example 55 RD11 RHH4 REH1 4.22 120 158 Example 56 RD11 RHH4 REH2 4.20 118 143 Example 57 RD11 RHH4 REH3 4.18 117 143 Example 58 RD11 RHH4 REH4 4.19 119 138 Example 59 RD11 RHH4 REH5 4.15 119 143 Example 60 RD11 RHH4 REH6 4.18 122 141 Example 61 RD11 RHH5 REH1 4.15 120 138 Example 62 RD11 RHH5 REH2 4.16 117 133 Example 63 RD11 RHH5 REH3 4.15 116 128 Example 64 RD11 RHH5 REH4 4.14 115 128 Example 65 RD11 RHH5 REH5 4.14 114 130 Example 66 RD11 RHH5 REH6 4.14 116 125 Example 67 RD11 RHH6 REH1 4.18 111 138 Example 68 RD11 RHH6 REH2 4.19 111 133 Example 69 RD11 RHH6 REH3 4.20 115 123 Example 70 RD11 RHH6 REH4 4.17 113 128 Example 71 RD11 RHH6 REH5 4.18 112 133 Example 72 RD11 RHH6 REH6 4.16 111 131 [Table 5] Emission material layer Operating voltage (V) EQE(%,relative value) LT95(%,relative value) Doping material Host material Comparative example 3 RD15 CBP 4.29 100 100 Example 73 RD15 RHH1 REH1 4.25 112 120 Example 74 RD15 RHH1 REH2 4.24 114 118 Example 75 RD15 RHH1 REH3 4.20 107 110 Example 76 RD15 RHH1 REH4 4.19 108 110 Example 77 RD15 RHH1 REH5 4.21 110 115 Example 78 RD15 RHH1 REH6 4.20 112 118 Example 79 RD15 RHH2 REH1 4.22 110 118 Example 80 RD15 RHH2 REH2 4.20 112 115 Example 81 RD15 RHH2 REH3 4.19 107 115 Example 82 RD15 RHH2 REH4 4.20 110 116 Example 83 RD15 RHH2 REH5 4.21 108 117 Example 84 RD15 RHH2 REH6 4.22 110 115 Example 85 RD15 RHH3 REH1 4.25 112 115 Example 86 RD15 RHH3 REH2 4.23 112 110 Example 87 RD15 RHH3 REH3 4.20 107 120 Example 88 RD15 RHH3 REH4 4.21 108 120 Example 89 RD15 RHH3 REH5 4.20 110 117 Example 90 RD15 RHH3 REH6 4.20 112 115 [Table 6] Emission material layer Operating voltage (V) EQE(%,relative value) LT95(%,relative value) Doping material Host material Comparative example 3 RD15 CBP 4.29 100 100 Example 91 RD15 RHH4 REH1 4.24 112 125 Example 92 RD15 RHH4 REH2 4.19 117 115 Example 93 RD15 RHH4 REH3 4.23 122 120 Example 94 RD15 RHH4 REH4 4.21 112 115 Example 95 RD15 RHH4 REH5 4.20 112 110 Example 96 RD15 RHH4 REH6 4.22 118 118 Example 97 RD15 RHH5 REH1 4.23 113 120 Example 98 RD15 RHH5 REH2 4.22 114 118 Example 99 RD15 RHH5 REH3 4.22 112 116 Example 100 RD15 RHH5 REH4 4.20 117 118 Example 101 RD15 RHH5 REH5 4.19 112 115 Example 102 RD15 RHH5 REH6 4.21 114 118 Example 103 RD15 RHH6 REH1 4.23 117 120 Example 104 RD15 RHH6 REH2 4.22 116 118 Example 105 RD15 RHH6 REH3 4.23 114 112 Example 106 RD15 RHH6 REH4 4.22 113 114 Example 107 RD15 RHH6 REH5 4.21 115 115 Example 108 RD15 RHH6 REH6 4.20 112 116 [Table 7] Emission material layer Operating voltage (V) EQE (%,relative value) LT95 (%,relative value) Doping material Host material Comparative example 4 RD18 CBP 4.28 100 100 Example 109 RD18 RHH1 REH1 4.18 130 119 Example 110 RD18 RHH1 REH2 4.15 132 117 Example 111 RD18 RHH1 REH3 4.18 125 111 Example 112 RD18 RHH1 REH4 4.15 124 111 Example 113 RD18 RHH1 REH5 4.15 124 114 Example 114 RD18 RHH1 REH6 4.18 125 117 Example 115 RD18 RHH2 REH1 4.20 128 116 Example 116 RD18 RHH2 REH2 4.18 130 113 Example 117 RD18 RHH2 REH3 4.17 123 114 Example 118 RD18 RHH2 REH4 4.18 122 115 Example 119 RD18 RHH2 REH5 4.19 121 115 Example 120 RD18 RHH2 REH6 4.20 124 113 Example 121 RD18 RHH3 REH1 4.19 130 114 Example 122 RD18 RHH3 REH2 4.17 130 111 Example 123 RD18 RHH3 REH3 4.14 125 118 Example 124 RD18 RHH3 REH4 4.15 122 115 Example 125 RD18 RHH3 REH5 4.16 120 118 Example 126 RD18 RHH3 REH6 4.15 125 116 [Table 8] Emission material layer Operating voltage (V) EQE(%,relative value) LT95(%,relative value) Dosing agent Host material Comparative example 4 RD18 CBP 4.28 100 100 Example 127 RD18 RHH4 REH1 4.18 128 115 Example 128 RD18 RHH4 REH2 4.16 128 114 Example 129 RD18 RHH4 REH3 4.17 126 113 Example 130 RD18 RHH4 REH4 4.15 123 112 Example 131 RD18 RHH4 REH5 4.16 123 113 Example 132 RD18 RHH4 REH6 4.16 123 114 Example 133 RD18 RHH5 REH1 4.19 126 115 Example 134 RD18 RHH5 REH2 4.18 123 114 Example 135 RD18 RHH5 REH3 4.18 122 116 Example 136 RD18 RHH5 REH4 4.16 121 115 Example 137 RD18 RHH5 REH5 4.15 120 113 Example 138 RD18 RHH5 REH6 4.17 122 116 Example 139 RD18 RHH6 REH1 4.19 118 116 Example 140 RD18 RHH6 REH2 4.18 118 113 Example 141 RD18 RHH6 REH3 4.17 116 112 Example 142 RD18 RHH6 REH4 4.18 119 113 Example 143 RD18 RHH6 REH5 4.17 118 111 Example 144 RD18 RHH6 REH6 4.16 119 114

[0129] As can be seen from the results in Tables 1 to 8, examples 1 to 144 provide the OLEDs that use the metal-organic compound fulfilling the structure represented by chemical formula 1 as the doping material of the emission material layer and the mixture of the compound represented by chemical formula 4 and the compound represented by chemical formula 5 as the host material, exhibit low operating voltages and increased external quantum efficiency (EQE) and lifetime (LT95) compared to the OLEDs of comparison examples 1 to 4 that use the single material as the host.

[0130] In the organic light-emitting diode (OLED) according to the present invention, it is possible to improve the efficiency and lifetime characteristics of the OLED and to ensure low power consumption characteristics by reducing the operating voltage, by using the metal-organic compound represented by chemical formula 1 as the phosphorus dopant and a mixture of a compound represented by chemical formula 4 and a compound represented by chemical formula 5 as the phosphorus host. DESCRIPTION OF REFERENCE NUMBERS

[0131] 100, 4000: organic light-emitting diodes (OLEDs) 110, 4100: first electrode 120, 4200: second electrode 130, 230, 330, 4300: an intermediate shift 140: Hole injection layer 150: hole transport layer, 251: first hole transport layer, 252: second hole transport layer, 253: third hole transport layer 160: Emission material layer, 261: First emission material layer, 262: Second emission material layer, 263: Third emission material layer 160', 262': Doping agent 160'', 262'': Hole Transport type Host 160''', 262''': Electron transport type Host 170: electron transport layer, 271: first electron transport layer, 272: second electron transport layer, 273: third electron transport layer 180: Electron injection layer 3000: OLED display device 3010: Substrat 3100: Semiconductor layer 3200: Gate insulating film 3300: Gate electrode 3400: Interlayer insulating foil 3420, 3440: first and second semiconductor contact holes 3520: Source electrode 3540: Drain electrode 3600: Color filter 3700: Planarization layer 3720: Drain contact hole 3800: Bank shift 3900: Encapsulation film

Claims

[1] Organic light-emitting diode, comprising: a first electrode; a second electrode opposite the first electrode; and an intermediate layer that is arranged between the first electrode and the second electrode, wherein the intermediate layer comprises an emission material layer and the emission material layer contains a doping material and a host material, the doping material comprises a metal-organic compound of the following chemical formula 1, and the host material comprises a mixture of a compound represented by chemical formula 4 below and a compound represented by chemical formula 5 below: M(L A ) m (L B ) n <Chemische Formel 1> in chemical formula 1 M is a central coordination metal, selected from the group consisting of molybdenum (Mo), tungsten (W), rhenium (Re), ruthenium (Ru), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt) and gold (Au), is L A a ligand represented by the chemical formula 2, is L B a bidentate ligand, is m 1, 2 or 3, is n 0, 1 or 2, and is (m+n) the oxidation number of the central coordination metal M, in chemical formula 2 A has selected a ring structure consisting of substituted or unsubstituted pyridine and substituted or unsubstituted pyrimidine, R1 to R8 are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; and a substituted or unsubstituted C4-C20 bicycloalkyl group, and R1 to R8 are optionally partially or completely deuterated. R9 is in each case independently selected at least one from the group consisting of hydrogen, deuterium; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; a C3-C20 cycloalkyl group; halogen; a nitrile group; a substituted or unsubstituted C1-C20 alkoxy group; and combinations thereof, and R9 is optionally partially or completely deuterated. is, if any of R1 to R9 is substituted, a substituent of R1 to R9 is each independently selected from the group consisting of deuterium; halogen; a C3-C10 cycloalkyl group; and combinations thereof, and, if a plurality of the substituents of R1 to R9 are present, each substituent is the same or different from each other, Y is at least one selected from the group consisting of BR 10 ; CR 10 R 11 ; C=O; CNR 10 ; SiR 10 R 11 ; NR 10 ; PR 10 ; AsR 10 ; SbR 10 ; P(O)R 10 ; P(S)R 10 ; P(Se)R 10 ; As(O)R 10 ; As(S)R 10 ; As(Se)R 10 ; Sb(O)R 10 ; Sb(S)R 10 ; Sb(Se)R 10 ; O; S; Se; Te; SO; SO2; SeO; SeO2; TeO; and TeO2, X1 to X4 are each independently selected from CR 12 and nitrogen (N), are, if any two adjacent X1 to X4 are CR 12 are two R 12 not bound or bound by forming a 5- or 6-membered, substituted or unsubstituted aromatic ring or a heteroaromatic ring structure, and is, if any two of X1 to X4 are adjacent, CR 12 is and the other nitrogen (N) is, R 12 not bound or bound to the nitrogen to form a 5-membered or 6-membered heteroaromatic ring structure, and is the aromatic ring or heteroaromatic ring structure that is formed when R 12 is bound, not or substituted with at least one deuterium, are R 10 to R 12each independently selected at least one from the group consisting of hydrogen; deuterium; halogen; a hydroxyl group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C1-C20 heteroalkyl group; a substituted or unsubstituted C7-C20 arylalkyl group; a substituted or unsubstituted C2-C20 alkenyl group; a substituted or unsubstituted C3-C20 cycloalkenyl group; a substituted or unsubstituted C2-C20 heteroalkenyl group; a substituted or unsubstituted C2-C20 alkynyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group;a substituted or unsubstituted C1-C20 alkoxy group; an amino group; a silyl group; a C2-C30 acyl group; a carboxyl group; a nitrile group; an isonitrile group; a sulfanyl group; and a phosphino group; is when one of the residues R 10 to R 12 is substituted, a substituent of R 10 to R 12 each independently at least one selected from the group consisting of deuterium, halogen and combinations thereof, and is, if several of the substituents of R 10 to R 12 are present, each substituent being the same or different from each other, is p equal to 2, and The dashed line represents a connection position to the central coordination metal M, in chemical formula 4 Ar is each independently a divalent group of an aromatic ring or a heteroaromatic ring, selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran and dibenzothiophene, Ar1 and Ar2 are each independently a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C2-C60 heteroaryl group, are R 21-1 to R 21-4each independently selected at least one from the group consisting of deuterium; halogen; a hydroxyl group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C1-C20 heteroalkyl group; a substituted or unsubstituted C7-C20 arylalkyl group; a substituted or unsubstituted C2-C20 alkenyl group; a substituted or unsubstituted C3-C20 cycloalkenyl group; a substituted or unsubstituted C2-C20 heteroalkenyl group; a substituted or unsubstituted C2-C20 alkynyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group; a substituted or unsubstituted C1-C20 alkoxy group; an amino group; a silyl group;a C2-C30 acyl group; a carboxyl group; a nitrile group; an isonitrile group; a sulfanyl group; and a phosphino group; is an integer from 0 to 3, and if o is an integer of 2 or 3, then R 21-1 same or different and, if necessary, partially or completely deuterated is an integer from 0 to 4, and if s is an integer from 2 to 4, then R 21-2 same or different and, if necessary, partially or completely deuterated is an integer from 0 to 4, and if t is an integer from 2 to 4, then R 21-3 same or different and, if applicable, R 21-3 partially or fully deuterated is an integer from 0 to 4, and if u is an integer from 2 to 4, then R 21-4 same or different and, if necessary, partially or completely deuterated is an integer from 0 to 2, and is an integer of 0 or 1, and is a linker L of at least one selected from the group consisting of a substituted or unsubstituted C6-C30 arylene group; a substituted or unsubstituted C2-C30 heteroarylene group; and a substituted or unsubstituted C7-C20 arylalkylene group, in chemical formula 5 A B-ring is a substituted or unsubstituted monocyclic or polycyclic aromatic condensed C6-C30 ring, are X 11 and X 12 , each independently of each other, N or CR', L1 is selected from the group consisting of a single bond; a substituted or unsubstituted C6-C30 arylene group; a substituted or unsubstituted C2-C30 heteroarylene group; and a substituted or unsubstituted C3-C30 cycloalkylene group. Ar3 is selected from the group consisting of hydrogen; deuterium; halogen; a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group; and an -L 24 -SiR k R l R m group, where L 24 a single bond, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroarylene group, where R k , R l and R m each independently being hydrogen, a substituted or unsubstituted C1-C30 alkyl group or a substituted or unsubstituted C6-C30 aryl group, wherein one or more of the hydrogens are an alkyl group, an aryl group, a heteroaryl group or a group -L 24 -SiR k R l R m, which is Ar3, unsubstituted or substituted with one or more deuterium and halogen atoms, Z is selected from the group consisting of the following structures, W is selected from the group consisting of O, S, and NR. 31 ; CR 31 R 32 ; and SiR 31 R 32 , are R 22 to R 32and R' each independently selected from the group consisting of hydrogen, deuterium; halogen; a hydroxyl group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C1-C20 heteroalkyl group; a substituted or unsubstituted C7-C20 arylalkyl group; a substituted or unsubstituted C2-C20 alkenyl group; a substituted or unsubstituted C3-C20 cycloalkenyl group; a substituted or unsubstituted C2-C20 heteroalkenyl group; a substituted or unsubstituted C2-C20 alkynyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group; a substituted or unsubstituted C1-C20 alkoxy group; an amino group; a silyl group;a C2-C30 acyl group; a carboxyl group; a nitrile group; an isonitrile group; a sulfanyl group; and a phosphino group, and ; a, c, e and i are each independently an integer of 1, 2, 3 or 4; b, d, g are each independently an integer of 1, 2 or 3; f is an integer of 1, 2, 3, 4, 5 or 6; and h is an integer of 1, 2, 3, 4 or 5. [2] Organic light-emitting diode according to claim 1, wherein L B in chemical formula 1 by a structure of at least one from the group consisting of chemical formula 3-1 and chemical formula 3-2 below: in chemical formula 3-1 and chemical formula 3-2, Z3 to Z5 are each independently selected from the group consisting of hydrogen; deuterium; halogen; a hydroxyl group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C1-C20 heteroalkyl group; a substituted or unsubstituted C7-C20 arylalkyl group; a substituted or unsubstituted C2-C20 alkenyl group; a substituted or unsubstituted C3-C20 cycloalkenyl group; a substituted or unsubstituted C2-C20 heteroalkenyl group; a substituted or unsubstituted C2-C20 alkynyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group;a substituted or unsubstituted C1-C20 alkoxy group; an amino group; a silyl group; a C2-C30 acyl group; a carboxyl group; a nitrile group; an isonitrile group; a sulfanyl group; and a phosphino group; Z6 and Z7 are each independently selected from the group consisting of oxygen (O) and NR. z , and is R z each independently selected from the group consisting of hydrogen, a linear C1-C20 alkyl group and a substituted or unsubstituted branched C3-C20 alkyl group, is R z preferably isopropyl, and The dashed line represents a connection position to the central coordination metal M. [3] Organic light-emitting diode according to claim 1 or 2, wherein the compound represented by chemical formula 1 is a compound represented by a structure selected from the group consisting of chemical formula 1-1-(1), chemical formula 1-1-(2), chemical formula 1-1-(3), chemical formula 1-1-(4), chemical formula 1-1-(5) and chemical formula 1-1-(6), the compound represented by chemical formula 1-2 is represented by a structure selected from the group consisting of chemical formula 1-2-(1), chemical formula 1-2-(2), chemical formula 1-2-(3), chemical formula 1-2-(4), chemical formula 1-2-(5) and chemical formula 1-2-(6), and The compound represented by chemical formula 1-3 is represented by a structure selected from the group consisting of chemical formula 1-3-(1), chemical formula 1-3-(2), chemical formula 1-3-(3), chemical formula 1-3-(4), chemical formula 1-3-(5) and chemical formula 1-3-(6): in the chemical formula 1-1-(1), the chemical formula 1-1-(2), the chemical formula 1-1-(3), the chemical formula 1-1-(4), the chemical formula 1-1-(5), the chemical formula 1-1-(6), the chemical formula 1-2-(1), the chemical formula 1-2-(2), the chemical formula 1-2-(3), the chemical formula 1-2-(4), the chemical formula 1-2-(5), the chemical formula 1-2-(6), the chemical formula 1-3-(1), the chemical formula 1-3-(2), the chemical formula 1-3-(3), the chemical formula 1-3-(4), the chemical formula 1-3-(5), and the chemical formula 1-3-(6), M, X1 to X4, Y, R1 to R9, p, m and n are as defined in chemical formula 1, and Z3 to Z7 are defined as in chemical formula 3-1 and chemical formula 3-2. [4] Organic light-emitting diode according to any one of claims 1 to 3, wherein at least one of the R9 residues in chemical formula 2 is selected from the group consisting of deuterium; a substituted or unsubstituted linear C1-C20 alkyl group; a substituted or unsubstituted branched C3-C20 alkyl group; a C3-C20 cycloalkyl group; halogen; a nitrile group; a substituted or unsubstituted C1-C20 alkoxy group; and Combinations thereof, where R9 is optionally partially or completely deuterated, and / or where R 10 to R 12in chemical formula 2, at least one of the following is selected independently from the group consisting of hydrogen; deuterium; halogen; a nitrile group; a nitro group; a substituted or unsubstituted C1-C20 alkoxy group; an amino group; a substituted or unsubstituted linear C1-C10 alkyl group; a substituted or unsubstituted branched C3-C10 alkyl group; and a substituted or unsubstituted C3-C10 cycloalkyl group. [5] Organic light-emitting diode according to any one of claims 1 to 4, wherein Ar1 and Ar2 are each independently a monovalent group selected from the group consisting of substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuran; substituted or unsubstituted dibenzothiophene; and substituted or unsubstituted spirobifluorene, and at least one hydrogen in one of Ar1 and Ar2 is substituted with at least one selected from the group consisting of deuterium; halogen atom; a C1-C10 alkyl group; a C6-C20 aryl group; a C2-C20 heteroaryl group; a nitrile group; a silyl group; and combinations thereof. [6] Organic light-emitting diode according to any one of claims 1-5, wherein X 11 and X 12 in the chemical formula 5 N. [7] Organic light-emitting diode according to one of claims 1-6, wherein the intermediate layer further comprises one or more of the following layers: a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron barrier layer, an electron transport layer and an electron injection layer. [8] Organic light-emitting diode according to any one of claims 1-7, wherein the intermediate layer comprises one or more light-emitting parts, and wherein the emission material layer is a layer in at least one of the one or more light-emitting parts and is a red phosphorescent layer. [9] Organic light-emitting diode according to any one of claims 1-8, wherein the organometallic compound represented by chemical formula 1 is a compound selected from the group consisting of the following compounds RD-1 to RD-20: [10] Organic light-emitting diode according to any one of claims 1 to 9, wherein the compound represented by chemical formula 4 is a compound selected from the group consisting of the following compounds RHH-1 to RHH-20: [11] Organic light-emitting diode according to any one of claims 1 to 10, wherein the compound represented by chemical formula 5 is a compound selected from the group consisting of the following compounds REH-1 to REH-20: [12] Organic light-emitting diode according to any one of claims 8 to 11, wherein several light-emitting parts are located between the first electrode and the second electrode, and the several light-emitting parts have a structure which is connected by charge-generating layers which are arranged between the several light-emitting parts. [13] An organic light-emitting diode display device comprising: a substrate; a drive element that is arranged on the substrate; and the organic light-emitting diode according to one of claims 1 to 12, which is arranged on the substrate and connected to the drive element.

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