Organic light-emitting device comprising an organometallic compound and multiple host materials
The integration of a specific organometallic compound and host materials in the organic light-emitting device enhances phosphorescent performance, addressing efficiency and lifespan issues in existing devices.
Patent Information
- Application Number
- JP2023194066
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2022-11-25
- Filing Date
- 2023-11-15
- Publication Date
- 2025-10-16
- Estimated Expiration
- 2043-11-15
AI Technical Summary
Existing organic light-emitting devices face limitations in improving driving voltage, efficiency, and lifespan, particularly in the use of conventional organometallic compounds as phosphorescent materials.
An organic light-emitting device incorporating a dopant material represented by Chemical Formula 1 and a host material comprising a two-host mixture of compounds represented by Chemical Formulas 2 and 3, which include organometallic compounds and specific aromatic ring groups, to enhance phosphorescent performance.
The proposed configuration improves driving voltage, efficiency, and lifespan characteristics of the organic light-emitting device by utilizing the organometallic compound as a phosphorescent dopant and a mixed host material.
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Abstract
Description
[Technical Field]
[0001] The present invention relates to an organic light-emitting device comprising an organometallic compound and a plurality of host materials. [Background technology]
[0002] 2. Description of the Related Art Display devices are gaining increasing attention as they are applied to various fields. As one of the display devices, the technology of organic light emitting display devices including organic light emitting diodes (OLEDs) is rapidly developing.
[0003] An organic light-emitting device is a device in which, when electric charges are injected into an emissive layer formed between a positive electrode and a negative electrode, electrons and holes combine to form excitons, which then emit the energy of the excitons as light.Compared to existing display technologies, organic light-emitting diodes can be driven at a low voltage, consume relatively little power, and have excellent color reproduction.They also have the advantage of being applicable to flexible substrates, making them versatile and allowing the size of display devices to be freely adjusted.
[0004] Organic light emitting diodes (OLEDs) have superior viewing angles and brightness ratios compared to liquid crystal displays (LCDs), do not require backlighting, and are lightweight and ultra-thin. Organic light emitting diodes are formed by arranging multiple organic layers, such as a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, a light emitting layer, and an electron transport layer, between a negative electrode (electron injection electrode; cathode) and a positive electrode (hole injection electrode; anode).
[0005] In the structure of these organic light-emitting devices, when a voltage is applied between the two electrodes, electrons and holes are injected from the negative and positive electrodes, respectively, and excitons generated in the light-emitting layer emit light as they fall to the ground state.
[0006] Organic materials used in organic light-emitting devices can be broadly classified into emissive materials and charge transport materials. Emitting materials are an important factor in determining the luminous efficiency of organic light-emitting devices. They must have high quantum efficiency and excellent electron and hole mobility, and must be uniformly and stably present in the emitting layer. Emitting materials are classified into blue, red, green, and other emitting materials depending on the color they emit. Color-emitting materials are used as hosts or dopants to increase color purity and luminous efficiency through energy transfer.
[0007] In the case of fluorescent materials, only about 25% of the excitons formed in the light-emitting layer (singlet) are used to generate light, and the remaining 75% (triplet) are mostly lost to heat. In contrast, phosphorescent materials have a light-emitting mechanism that converts both singlet and triplet excitons into light.
[0008] To date, organometallic compounds have been used as phosphorescent materials in organic light-emitting devices. To improve the efficiency and lifetime of existing organic light-emitting devices, there remains a technical need to improve the performance of organic light-emitting devices by deriving highly efficient phosphorescent dopant materials and applying hosts with optimal optical properties. Summary of the Invention [Problem to be solved by the invention]
[0009] SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide an organic light-emitting device in which an organometallic compound and a plurality of host materials are applied to an organic light-emitting layer, which can improve driving voltage, efficiency, and lifespan.
[0010] The objects of the present invention are not limited to those mentioned above, and other objects and advantages of the present invention not mentioned above can be understood from the following description and can be more clearly understood from the examples of the present invention. Furthermore, it is clear that the objects and advantages of the present invention can be achieved by the means and combinations thereof set forth in the claims. [Means for solving the problem]
[0011] In order to solve the above problems, according to one aspect of the present invention, there is provided an organic light-emitting device including a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emitting layer, and the emitting layer includes a dopant material and a host material, wherein the dopant material includes an organometallic compound represented by the following Chemical Formula 1, and the host material includes a compound represented by the following Chemical Formula 2 and a compound represented by the following Chemical Formula 3: [ka]
[0012] In the above chemical formula 1, M is a central coordinating metal and may be one 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); Y's may be the same or different and each independently be one selected from the group consisting of BR, CR, R, C=O, C=NR, SiR, R, NR, PR, AsR, SbR, BiR, P(O)R, P(S)R, P(Se)R, As(O)R, As(S)R, As(Se)R, Sb(O)R, Sb(S)R, Sb(Se)R, Bi(O)R, Bi(S)R, Bi(Se)R, oxygen (O), sulfur (S), cerium (Se), tellurium (Te), SO, SO, Se, SeO, SeO, Teo, and TeO; X1 and X2 may be different from each other and may each independently be one selected from the group consisting of carbon (C), nitrogen (N) and phosphorus (P); However, one of X1 and X2 may be carbon (C), and the other may be one of nitrogen (N) or phosphorus (P); X3, X4, X5, X6, X7, X8, X9, X 10 , X 11 , X12 , X 13 , and X 14 are the same or different and may each independently be one selected from the group consisting of CR7, nitrogen (N), phosphorus (P), sulfur (S), and oxygen (O); Selectively, X3, X4, X5, X6, X7, X8, X9, X 10 , X 11 , X 12 , X 13 , and X 14 adjacent groups selected from the group consisting of can be linked to each other to form a 5-membered ring or a 6-membered ring; R1, R2, R7, Ra, Rb, and Rc each independently represent hydrogen, deuterium, a halogen, a hydroxyl group, a cyano 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 C3-C30 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group; [ka] may be a bidentate ligand, m may be a constant of 1, 2 or 3, n may be a constant of 0, 1 or 2, and m+n may be the oxidation number of the metal M; [ka]
[0013] In the above chemical formula 2, Ar may each independently be an aromatic ring group selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran, and dibenzothiophene; Ar1 and Ar2 may each independently be a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C3-C60 heteroaryl group; R8 each independently represents hydrogen, deuterium, a halogen, a hydroxyl group, a cyano 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 C7-C20 arylalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, a substituted or unsubstituted C7-C20 arylalkyl group, a substituted or unsubstituted C2-C20 arylalkyl group, a substituted or unsubstituted C3 ... may be one selected from the group consisting of a substituted C2-C20 heteroalkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group; o may be a constant of 0, 1, 2 or 3, p may each independently be a constant of 0, 1, 2, 3 or 4, q may be a constant of 0, 1 or 2, and r may be a constant of 0 or 1; When r is 1, the linker L may be one selected from the group consisting of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, and a substituted or unsubstituted C7-C20 arylalkyl group; [ka]
[0014] In the above chemical formula 3, Ring A may be a substituted or unsubstituted C3-C30 aryl group; X 28 and X 29 may each independently be N or CR'; L1 may be one 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 may be one 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, a substituted or unsubstituted C1-C30 silylalkyl group, and a substituted or unsubstituted C6-C30 silylaryl group; one or more hydrogen atoms of the alkyl group, aryl group, heteroaryl group, silylalkyl group, or silylaryl group represented by Ar3 may be substituted with one or more deuterium atoms and halogen atoms; Each Z may independently be one selected from the group consisting of the following structures: [ka] W is O, S, NR 18 , C.R. 18 R 19 , and SiR 18 R 19 may be one selected from the group consisting of R9~R 19and R' are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C1-C20 heteroalkyl group, substituted or unsubstituted C7-C20 arylalkyl group, substituted or unsubstituted C2-C20 alkenyl group, substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C7-C20 arylalkyl group, substituted or unsubstituted C2-C20 alkenyl group, substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C7-C20 arylalkyl group, substituted or unsubstituted C2-C20 arylalkyl group, substituted or unsubstituted C3 ... may be one selected from the group consisting of an 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 C3-C30 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group; a, c, e, and i may each independently be a constant of 1, 2, 3, or 4; b, d, and g may each independently be a constant of 1, 2, or 3; f may be a constant of 1, 2, 3, 4, 5, or 6; and h may be a constant of 1, 2, 3, 4, or 5.
[0015] According to another aspect of the present invention, an organic light emitting display device including the organic light emitting device according to an aspect of the present invention may be provided. [Effects of the Invention]
[0016] The organic light emitting device according to the present invention uses the organometallic compound represented by Chemical Formula 1 as a phosphorescent dopant, and uses a mixture of the compound represented by Chemical Formula 2 and the compound represented by Chemical Formula 3 as a phosphorescent host, thereby improving the driving voltage, efficiency, and lifespan characteristics of the organic light emitting device.
[0017] The effects of this specification are not limited to those mentioned above, and other effects not mentioned can be clearly understood by those having ordinary skill in the technical field to which the present invention pertains from the description below. [Brief explanation of the drawings]
[0018] [Figure 1] 1 is a cross-sectional view schematically illustrating an organic light emitting device according to an embodiment of the present invention. [Figure 2] 1 is a cross-sectional view schematically illustrating an organic light emitting device having a tandem structure including two light emitting portions according to an embodiment of the present invention. [Figure 3] 1 is a cross-sectional view schematically illustrating an organic light emitting device having a tandem structure and including three light emitting units according to an embodiment of the present invention. [Figure 4] 1 is a cross-sectional view schematically illustrating an organic light emitting display device to which an organic light emitting device according to an exemplary embodiment of the present invention is applied; DETAILED DESCRIPTION OF THE INVENTION
[0019] The above-mentioned objects, features, and advantages will be described in detail below with reference to the accompanying drawings, so that those skilled in the art can easily implement the technical concept of the present invention. In describing the present invention, if a detailed description of known technologies relating to the present invention is deemed to obscure the gist of the present invention, the detailed description will be omitted. Hereinafter, preferred embodiments of the present invention will be described in detail with reference to the accompanying drawings. The same reference numerals in the drawings are used to indicate the same or similar components.
[0020] In describing this specification, if a detailed description of related publicly known technology is deemed to obscure the gist of this specification, that detailed description will be omitted.
[0021] In this specification, when an element is described as "comprising," "having," "consisting," "disposed," or "comprising," other parts can be added unless "only" is used. When an element is referred to in the singular, it also includes the plural unless expressly stated otherwise.
[0022] When interpreting the elements in this specification, unless otherwise expressly stated, they are to be interpreted as including a margin of error.
[0023] In this specification, when an arbitrary structure is arranged "on (or under)" a component or "above (or below)" a component, it means that the arbitrary structure is arranged in contact with the upper surface (or lower surface) of the component, and that other structures may be interposed between the component and the arbitrary structure arranged above (or below) the component.
[0024] The term "halo" or "halogen" as used herein includes fluorine, chlorine, bromine, and iodine.
[0025] The organometallic compound represented by Chemical Formula 1, the compound represented by Chemical Formula 2, and the compound represented by Chemical Formula 3 herein may include cases in which some or all of the hydrogen atoms are substituted with deuterium.
[0026] As used herein, the term "alkyl group" refers to both straight-chain and branched-chain alkyl groups. Unless otherwise specified, alkyl groups contain 1 to 20 carbon atoms and include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, etc., and further, alkyl groups can be optionally substituted.
[0027] As used herein, the term "cycloalkyl group" refers to a cyclic alkyl group. Unless otherwise specified, cycloalkyl groups contain 3 to 20 carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, and the like, and further include cycloalkyl groups that can be optionally substituted.
[0028] As used herein, the term "alkenyl group" refers to both straight-chain and branched-chain alkene groups. Unless otherwise specified, alkenyl groups contain 2 to 20 carbon atoms, and further, alkenyl groups can be optionally substituted.
[0029] As used herein, the term "alkynyl group" refers to both straight-chain and branched-chain alkyne groups. Unless otherwise specified, alkynyl groups contain 2 to 20 carbon atoms. Furthermore, alkynyl groups can be optionally substituted.
[0030] As used herein, the terms "aralkyl group" or "arylalkyl group" are used interchangeably and refer to an alkyl group having an aromatic group as a substituent, and further the alkylaryl group may be optionally substituted.
[0031] As used herein, the terms "aryl group" and "aromatic group" are used interchangeably, and aryl groups include both monocyclic and polycyclic groups. Polycyclic groups may include "fused rings," which are two or more rings in which two adjacent carbon atoms are common to both rings. Unless otherwise specified, aryl groups contain 6 to 60 carbon atoms, and further, aryl groups can be optionally substituted.
[0032] The term "heterocyclic group" as used herein means an aryl group, a cycloalkyl group, or an aralkyl group (arylalkyl group) in which one or more carbon atoms constituting the group are substituted with a heteroatom such as oxygen (O), nitrogen (N), or sulfur (S), and the heterocycle can be optionally substituted.
[0033] Unless otherwise specified, the term "carbon ring" used in this specification can be used as a term that includes both an aliphatic ring group, a "cycloalkyl group," and an aromatic ring group, an "aryl group (aromatic group)."
[0034] As used herein, the terms "heteroalkyl group" and "heteroalkenyl group" refer to groups in which one or more of the carbon atoms constituting the group have been substituted with a heteroatom such as oxygen (O), nitrogen (N), or sulfur (S), and the heteroalkyl group and heteroalkenyl group can be optionally substituted.
[0035] As used herein, the term "substituted" means that a substituent other than hydrogen (H) is bonded to the carbon. Unless otherwise defined herein, the substituent in "substituted" may be, for example, one selected from the group consisting of deuterium, tritium, an unsubstituted or halogen-substituted C1-C20 alkyl group, an unsubstituted or halogen-substituted C1-C20 alkoxy group, a halogen, a carboxyl group, an amine group, a C1-C20 alkylamine group, a nitro group, a C1-C20 alkylsilyl group, a C1-C20 alkoxysilyl group, a C3-C30 cycloalkylsilyl group, a C6-C30 arylsilyl group, a C6-C30 aryl group, a C6-C30 arylamine group, a C3-C30 heteroaryl group, and combinations thereof; however, the present invention is not limited thereto.
[0036] Each object and substituent defined herein may be the same or different unless otherwise specified.
[0037] The structure of the organometallic compound according to the present invention and the organic light-emitting device including the same will be described below.
[0038] Conventionally, organometallic compounds have been used as dopants in phosphorescent light-emitting layers, and 2-phenylpyridine is known as a typical ligand structure for organometallic compounds. However, these conventional light-emitting dopants have limitations in improving the efficiency and lifetime of organic light-emitting devices, necessitating the development of new light-emitting dopant materials. Experiments have demonstrated that by combining a hole transport host and an electron transport host as host materials with the dopant material, the efficiency and lifetime of organic light-emitting devices can be further increased, and the driving voltage can be reduced, thereby improving the properties of the organic light-emitting devices. This finding led to the completion of the present invention.
[0039] 1 , an organic light emitting device 100 may be provided that includes a first electrode 110, a second electrode 120 facing the first electrode 110, and an organic layer 130 disposed between the first electrode 110 and the second electrode 120. The organic layer 130 may include an emitting layer 160, which may include a dopant material 160′ and a host material 160″, 160′″. The dopant material may include an organometallic compound 160′ represented by Chemical Formula 1 below. The host material may include a two-host mixture of a compound 160″ represented by Chemical Formula 2 below as a hole-transporting host and a compound 160′″ represented by Chemical Formula 3 below as an electron-transporting host. [ka]
[0040] In the above chemical formula 1, M is a central coordinating metal and may be one 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); Y's may be the same or different and each independently be one selected from the group consisting of BR, CR, R, C=O, C=NR, SiR, R, NR, PR, AsR, SbR, BiR, P(O)R, P(S)R, P(Se)R, As(O)R, As(S)R, As(Se)R, Sb(O)R, Sb(S)R, Sb(Se)R, Bi(O)R, Bi(S)R, Bi(Se)R, oxygen (O), sulfur (S), cerium (Se), tellurium (Te), SO, SO, Se, SeO, SeO, Teo, and TeO; X1 and X2 may be different from each other and may each independently be one selected from the group consisting of carbon (C), nitrogen (N) and phosphorus (P); However, one of X1 and X2 may be carbon (C), and the other may be one of nitrogen (N) or phosphorus (P); R1, R2, R7, Ra, Rb, and Rc each independently represent hydrogen, deuterium, a halogen, a hydroxyl group, a cyano 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 C3-C30 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group; [ka] may be a bidentate ligand, m may be a constant of 1, 2 or 3, n may be a constant of 0, 1 or 2, and m+n may be the oxidation number of the metal M; [ka]
[0041] In the above chemical formula 2, Ar may each independently be an aromatic ring group selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran, and dibenzothiophene; Ar1 and Ar2 may each independently be a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C3-C60 heteroaryl group; R8 each independently represents hydrogen, deuterium, a halogen, a hydroxyl group, a cyano 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 C7-C20 arylalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, a substituted or unsubstituted C7-C20 arylalkyl group, a substituted or unsubstituted C2-C20 arylalkyl group, a substituted or unsubstituted C3 ... may be one selected from the group consisting of a substituted C2-C20 heteroalkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group; o may be a constant of 0, 1, 2 or 3; each p may independently be a constant of 0, 1, 2, 3 or 4; q may be a constant of 0, 1 or 2; and r may be a constant of 0 or 1; When r is 1, the linker L may be one selected from the group consisting of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, and a substituted or unsubstituted C7-C20 arylalkyl group; [ka]
[0042] In the above chemical formula 3, Ring A may be a substituted or unsubstituted C3-C30 aryl group; X 28 and X 29 may each independently be N or CR'; L1 may be one 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 may be one 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, a substituted or unsubstituted C1-C30 silylalkyl group, and a substituted or unsubstituted C6-C30 silylaryl group; one or more hydrogen atoms of the alkyl group, aryl group, heteroaryl group, silylalkyl group, or silylaryl group represented by Ar3 can be substituted with one or more deuterium atoms and halogen atoms; Each Z may independently be one selected from the group consisting of the following structures: [ka] W is O, S, NR 18 , C.R. 18 R 19 , and SiR 18 R 19 may be one selected from the group consisting of R9~R 19and R' are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C1-C20 heteroalkyl group, substituted or unsubstituted C7-C20 arylalkyl group, substituted or unsubstituted C2-C20 alkenyl group, substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C7-C20 arylalkyl group, substituted or unsubstituted C2-C20 alkenyl group, substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted C7-C20 arylalkyl group, substituted or unsubstituted C2-C20 arylalkyl group, substituted or unsubstituted C3 ... may be one selected from the group consisting of an 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 C3-C30 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group; a, c, e, and i may each independently be a constant of 1, 2, 3, or 4; b, d, and g may each independently be a constant of 1, 2, or 3; f may be a constant of 1, 2, 3, 4, 5, or 6; and h may be a constant of 1, 2, 3, 4, or 5.
[0043] According to another aspect of the present invention, an organic light emitting display device including the organic light emitting device according to an aspect of the present invention may be provided.
[0044] According to one embodiment of the present invention, the organometallic compound represented by the above formula 1 may have a homoleptic or heteroleptic structure, for example, a homoleptic structure in which n in the above formula 1 is 0, a heteroleptic structure in which n is 1; or a heteroleptic structure in which n is 2, for example, n may be 2.
[0045] According to one embodiment of the present invention, the compound may be represented by one structure selected from the group consisting of the following Chemical Formula 1-1 and Chemical Formula 1-2. [ka] [ka]
[0046] In the above chemical formula 1-1 and chemical formula 1-2, X3, X4, X5, X6, X7, X8, X9, X 10 , X 11 , X 12 , X 13 , and X 14 are the same or different and may each independently be one selected from the group consisting of CR7, nitrogen (N), phosphorus (P), sulfur (S), and oxygen (O); X3, X4, X5, X6, X7, X8, X9, X 10 , X 11 , X 12 , X 13 , and X 14 adjacent groups selected from the group consisting of: can be linked to each other to form a five- or six-membered ring; R7 is independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C1-C20 heteroalkyl group, substituted or unsubstituted C7-C20 arylalkyl group, substituted or unsubstituted C2-C20 alkenyl group, substituted or unsubstituted C3-C20 cycloalkenyl group, substituted or unsubstituted It may be one selected from the group consisting of a substituted C2-C20 heteroalkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group.
[0047] According to one embodiment of the present invention, the compound may be represented by one structure selected from the group consisting of the following Chemical Formula 1-3 to Chemical Formula 1-10. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0048] In the above chemical formulas 1-3 to 1-10, X 15 , X 16 , X 17 , X 18 , X 19 , X 20 , X 21 , X 22 , X 23 , X 24 , X 25 , X 26 , and X 27 are the same or different and may each independently be one selected from the group consisting of CR7, nitrogen (N), phosphorus (P), sulfur (S), and oxygen (O); X 15 , X 16 , X 17 , X 18 , X 19 , X 20 , X 21 , X 22 , X 23, X 24 , X 25 , X 26 , and X 27 adjacent groups selected from the group consisting of: can be linked to each other to form a five- or six-membered ring; Z3 and Z4 may each independently be one selected from the group consisting of oxygen (O), sulfur (S), and NR7; R3, R4, R5, R6, and R7 each independently represent hydrogen, deuterium, a halogen, a hydroxyl group, a cyano 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, or 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 C3-C30 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, an amino group, a silyl group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, and a phosphino group.
[0049] According to one embodiment of the present invention, Y in the above Chemical Formula 1 may be one selected from the group consisting of O, S, and CR1R2.
[0050] According to one embodiment of the present invention, M in the above Chemical Formula 1 may be iridium (Ir).
[0051] According to one embodiment of the present invention, the organometallic compound represented by the above Chemical Formula 1 may be one selected from the group consisting of the following Compounds RD-1 to RD-20, but is not limited thereto as long as it falls within the definition of the above Chemical Formula 1.
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[0052] According to one embodiment of the present invention, in Formula 2, Ar1 and Ar2 may each independently be one selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, dibenzofuran, dibenzothiophene, and spirobifluorene. In this case, one or more hydrogen atoms of Ar1 and / or Ar2, benzene, naphthalene, phenanthrene, fluorene, dibenzofuran, dibenzothiophene, or spirobifluorene, may be substituted with one or more hydrogen atoms selected from the group consisting of deuterium, halogen atoms, C1-C10 alkyl groups, cyano groups, and silyl groups.
[0053] According to one embodiment of the present invention, the organometallic compound represented by the above chemical formula 2 may be one selected from the group consisting of the following compounds RHH-1 to RHH-20, but is not limited thereto as long as it falls within the definition of the above chemical formula 2. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0054] According to one embodiment of the present invention, X in the above formula 3 28 and X 29 may be N, respectively.
[0055] According to one embodiment of the present invention, the organometallic compound represented by the above chemical formula 3 may be one selected from the group consisting of the following compounds REH-1 to REH-20, but is not limited thereto as long as it falls within the definition of the above chemical formula 3. [ka]
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[0056] In addition, in the organic light emitting device 100, the organic layer 130 disposed between the first electrode 110 and the second electrode 120 may have a structure including, in order from the first electrode 110, a hole injection layer 140 (HIL: Hole Injection Layer), a hole transport layer 150 (HTL: Hole Transfer Layer), an emission layer 160 (EML: Emission Material Layer), an electron transport layer 170 (ETL: Electron Transfer Layer), and an electron injection layer 180 (EIL: Electron Injection Layer). The second electrode 120 may be formed on the electron injection layer 180, and a protective film (not shown) may be formed thereon.
[0057] 1, a hole transport auxiliary layer may be further added between the hole transport layer 150 and the light emitting layer 160. The hole transport auxiliary layer includes a compound with good hole transport properties and adjusts the hole injection characteristics by reducing the HOMO energy level difference between the hole transport layer 150 and the light emitting layer 160. This reduces hole accumulation at the interface between the hole transport auxiliary layer and the light emitting layer 160 and reduces quenching, which is the annihilation of excitons due to polarons at the interface. This reduces degradation of the device, stabilizes the device, and improves its efficiency and lifetime.
[0058] The first electrode 110 may be a positive electrode and may be made of a conductive material having a relatively large work function, such as ITO, IZO, tin oxide, or zinc oxide, but is not limited thereto.
[0059] The second electrode 120 may be a negative electrode and may include, but is not limited to, conductive materials with relatively low work function values such as Al, Mg, Ca, Ag, or alloys or combinations thereof.
[0060] The hole injection layer 140 may be located between the first electrode 110 and the hole transport layer 150. The hole injection layer 140 functions to improve the interfacial properties between the first electrode 110 and the hole transport layer 150 and may be selected from materials having appropriate conductivity. The hole injection layer 140 may include a compound such as m-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, but not limited to, N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine).
[0061] The hole transport layer 150 is located adjacent to the light emitting layer 160 between the first electrode 110 and the light emitting layer 160. The hole transport layer 150 may include 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, and preferably includes NPB, but is not limited thereto.
[0062] According to one embodiment of the present invention, the light-emitting layer 160 may be formed by doping an organometallic compound represented by Chemical Formula 1 with a dopant 160′ to improve the luminous efficiency of the host 160″, 160′″ and the device. The dopant 160′ may be a material that emits green or red light, and preferably a green phosphorescent material.
[0063] According to one embodiment of the present invention, the doping concentration of the dopant 160′ may be adjusted within a range of 1 to 30 wt % based on the total weight of the two hosts 160″, 160′″. Although not limited thereto, for example, the doping concentration may 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 %, or for example, 5 to 6 wt %.
[0064] According to one embodiment of the present invention, the mixing ratio of the two hosts 160'', 160''' is not particularly limited. The host 160'', which is a compound represented by Chemical Formula 2, has hole transport properties, and the host 160'', which is a compound represented by Chemical Formula 3, has electron transport properties. Therefore, mixing two hosts can advantageously improve efficiency and lifespan, and the mixing ratio of the two hosts can be appropriately adjusted. Therefore, the mixing ratio of the two hosts, which is a mixture of the compound represented by Chemical Formula 2 and the compound represented by Chemical Formula 3, is not particularly limited. The ratio (by weight) of the compound represented by Chemical Formula 2 to the compound represented by Chemical Formula 3 may be, for example, 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, or for example, 8:2.
[0065] Furthermore, an electron transport layer 170 and an electron injection layer 180 may be sequentially stacked between the light-emitting layer 160 and the second electrode 120. The material of the electron transport layer 170 is required to have high electron mobility, and smooth electron transport enables a stable supply of electrons to the light-emitting layer.
[0066] For example, the material of the electron transport layer 170 is one used in the art, such as Alq3 (tris(8-hydroxyquinolino)aluminum), 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)aluminum), SAlq, TPBi(2,2',2-(1,3,5-benzinetriyl)-t Examples of the compound include ris(1-phenyl-1-H-benzimidazole), oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and preferably, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, but are not limited to this.
[0067] The electron injection layer 180 facilitates electron injection and may be made of any material commonly used in the art, including, but not limited to, compounds such as Alq3 (tris(8-hydroxyquinolino)aluminum), PBD, TAZ, spiro-PBD, BAlq, and SAlq. Alternatively, the electron injection layer 180 may be made of a metal compound, including, but not limited to, Liq, LiF, NaF, KF, RbF, CsF, FrF, BeF2, MgF2, CaF2, SrF2, BaF2, and RaF2.
[0068] The organic light emitting device of the present invention may be a white organic light emitting device having a tandem structure. In the case of a tandem organic light emitting device according to an embodiment of the present invention, two or more single light emitting stacks (or light emitting portions) may be formed by connecting them with a charge generation layer (CGL). The organic light emitting device may include two or more light emitting stacks (light emitting portions), each having a first electrode and a second electrode facing each other on a substrate, and an light emitting layer stacked between the first and second electrodes and emitting light in a specific wavelength band. The multiple light emitting stacks (light emitting portions) may be configured to emit the same color or different colors. Furthermore, one light emitting stack (light emitting portion) may also include one or more light emitting layers, and the multiple light emitting layers may be the same or different colors.
[0069] In this case, one or more of the light-emitting layers included in the plurality of light-emitting units may contain, as a dopant material, the organometallic compound represented by Chemical Formula 1 according to the present invention. The plurality of light-emitting units in the tandem structure may be connected to a charge generation layer (CGL) consisting of an N-type charge generation layer and a P-type charge generation layer.
[0070] 2 and 3, which are illustrative embodiments of the present invention, are cross-sectional views schematically illustrating organic light-emitting devices with a tandem structure having two light-emitting portions and three light-emitting portions, respectively.
[0071] As shown in FIG. 2, the organic light emitting device 100 of the present invention includes a first electrode 110 and a second electrode 120 facing each other, and an organic layer 230 located between the first electrode 110 and the second electrode 120. The organic layer 230 includes a first light emitting portion (ST1) located between the first electrode 110 and the second electrode 120 and including a first light emitting layer 261, a second light emitting portion (ST2) located between the first light emitting portion (ST1) and the second electrode 120 and including a second light emitting layer 262, and a charge generation layer (CGL) located between the first and second light emitting portions (ST1 and ST2). The charge generation layer (CGL) may include an N-type charge generation layer 291 and a P-type charge generation layer 292. At least one of the first light emitting layer 261 and the second light emitting layer 262 may include an organometallic compound represented by Chemical Formula 1 according to the present invention as a dopant 262′. For example, as shown in FIG. 2, the second light-emitting layer 262 of the second light-emitting unit (ST2) may include a compound 262′ represented by Chemical Formula 1 as a dopant, a compound 262″ represented by Chemical Formula 2 as a hole-transporting host, and a compound 262′″ represented by Chemical Formula 3 as an electron-transporting host. Although not shown in FIG. 2, each of the first and second light-emitting units (ST1 and ST2) may further include an additional light-emitting layer in addition to the first light-emitting layer 261 and the second light-emitting layer 262.
[0072] 3, the organic light emitting device 100 of the present invention includes a first electrode 110 and a second electrode 120 facing each other, and an organic layer 330 located between the first electrode 110 and the second electrode 120. The organic layer 330 includes a first light emitting portion (ST1) including a first light emitting layer 261, a second light emitting portion (ST2) including a second light emitting layer 262, a third light emitting portion (ST3) including a third light emitting layer 263, and a first charge generation layer (CGL1) located between the first and second light emitting portions (ST1 and ST2); and a second charge generation layer (CGL2) located between the second and third light emitting portions (ST2 and ST3). The first and second charge generation layers (CGL1 and CGL2) may include N-type charge generation layers 291 and 293 and P-type charge generation layers 292 and 294, respectively. One or more of the first light-emitting layer 261, the second light-emitting layer 262, and the third light-emitting layer 263 may include an organometallic compound represented by Chemical Formula 1 according to the present invention as a dopant. For example, as shown in FIG. 3, the second light-emitting layer 262 of the second light-emitting portion (ST2) may include a compound 262' represented by Chemical Formula 1 as a dopant, a compound 262" represented by Chemical Formula 2 as a hole-transporting host, and a compound 262'" represented by Chemical Formula 3 as an electron-transporting host. Although not shown in FIG. 3, each of the first, second, and third light-emitting portions (ST1, ST2, and ST3) may further include an additional light-emitting layer in addition to the first light-emitting layer 261, the second light-emitting layer 262, and the third light-emitting layer 263, and thus may be formed of a plurality of light-emitting layers.
[0073] Furthermore, the organic light emitting device according to an embodiment of the present invention may have a tandem structure in which four or more light emitting portions and three or more charge generating layers are disposed between the first electrode and the second electrode.
[0074] The organic light emitting device according to the present invention can be used in an organic light emitting display device, a lighting device using the organic light emitting device, etc. As an example, Figure 4 is a cross-sectional view schematically illustrating an organic light emitting display device using the organic light emitting device according to an exemplary embodiment of the present invention.
[0075] 4, an organic light emitting display device 3000 may include a substrate 3010, an organic light emitting element 4000, and an encapsulation film 3900 covering the organic light emitting element 4000. A driving thin film transistor (Td) serving as a driving element and the organic light emitting element 4000 connected to the driving thin film transistor (Td) are located on the substrate 3010.
[0076] Although not explicitly shown in FIG. 4, the substrate 3010 further includes gate lines and data lines that cross each other to define pixel regions, power lines that extend parallel to and spaced apart from either the gate lines or the data lines, switching thin film transistors connected to the gate lines and the data lines, and storage capacitors connected to the power lines and one electrode of the switching thin film transistors.
[0077] The driving thin film transistor (Td) is connected to the switching thin film transistor and includes a semiconductor layer 3100, a gate electrode 3300, a source electrode 3520, and a drain electrode 3540.
[0078] The semiconductor layer 3100 is formed on the substrate 3010 and may be made of an oxide semiconductor material or polycrystalline silicon. When the semiconductor layer 3100 is made of an oxide semiconductor material, a light-shielding pattern (not shown) may be formed under the semiconductor layer 3100. The light-shielding pattern prevents light from entering the semiconductor layer 3100, thereby preventing deterioration of the semiconductor layer 3100 due to light. Alternatively, the semiconductor layer 3100 may be made of polycrystalline silicon, in which case both edges of the semiconductor layer 3100 may be doped with impurities.
[0079] On top of the semiconductor layer 3100, a gate insulating layer 3200 made of an insulating material is formed on the front surface of the substrate 3010. The gate insulating layer 3200 may be made of an inorganic insulating material such as silicon oxide or silicon nitride.
[0080] A gate electrode 3300 made of a conductive material such as metal is formed on the gate insulating layer 3200, corresponding to the center of the semiconductor layer 3100. The gate electrode 3300 is connected to a switching thin film transistor.
[0081] An interlayer insulating film 3400 made of an insulating material is formed on the front surface of the substrate 3010 above the gate electrode 3300. The interlayer insulating film 3400 may be made of an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or photo-acryl.
[0082] The interlayer insulating film 3400 has first and second semiconductor layer contact holes 3420 and 3440 exposing both sides of the semiconductor layer 3100. The first and second semiconductor layer contact holes 3420 and 3440 are located on both sides of the gate electrode 3300 and spaced apart from the gate electrode 3300.
[0083] A source electrode 3520 and a drain electrode 3540 made of a conductive material such as metal are formed on the interlayer insulating film 3400. The source electrode 3520 and the drain electrode 3540 are spaced apart from each other around the gate electrode 3300 and contact both sides of the semiconductor layer 3100 through first and second semiconductor layer contact holes 3420 and 3440, respectively. The source electrode 3520 is connected to a power wiring (not shown).
[0084] The semiconductor layer 3100, the gate electrode 3300, the source electrode 3520, and the drain electrode 3540 constitute a driving thin film transistor (Td), and the driving thin film transistor (Td) has a coplanar structure in which the gate electrode 3300, the source electrode 3520, and the drain electrode 3540 are located on top of the semiconductor layer 3100.
[0085] Alternatively, the driving thin film transistor (Td) may have an inverted staggered structure in which a gate electrode is located below a semiconductor layer and a source electrode and a drain electrode are located above the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon. Meanwhile, the switching thin film transistor (not shown) may have substantially the same structure as the driving thin film transistor (Td).
[0086] Meanwhile, the organic light emitting display 3000 may include a color filter 3600 that absorbs light generated by the organic light emitting element 4000. For example, the color filter 3600 may absorb red (R), green (G), blue (B), and white (W) light. In this case, the red, green, and blue color filter patterns that absorb light may be formed separately for each pixel region, and each color filter pattern may be disposed overlapping with the organic layer 4300 of the organic light emitting element 4000 that emits light in the wavelength band to be absorbed. By employing the color filter 3600, the organic light emitting display 3000 may implement full color.
[0087] For example, if the organic light emitting display device 3000 is a bottom-emission type, the color filter 3600 that absorbs light may be located on the interlayer insulating film 3400 corresponding to the organic light emitting element 4000. In an exemplary embodiment, if the organic light emitting display device 3000 is a top-emission type, the color filter may be located on the organic light emitting element 4000, i.e., on the second electrode 4200. For example, the color filter 3600 may be formed to a thickness of 2 to 5 μm.
[0088] Meanwhile, a planarization layer 3700 having a drain contact hole 3720 exposing the drain electrode 3540 of the driving thin film transistor (Td) is formed covering the driving thin film transistor (Td).
[0089] On the planarization layer 3700, a first electrode 4100 connected to the drain electrode 3540 of the driving thin film transistor (Td) through the drain contact hole 3720 is formed separately for each pixel region.
[0090] The first electrode 4100 may be an anode and may be made of a conductive material with a relatively high work function, for example, a transparent conductive material such as ITO, IZO, or ZnO.
[0091] Meanwhile, when the organic light emitting display device 3000 is a top-emission type, a reflective electrode or a reflective layer may be further formed under the first electrode 4100. For example, the reflective electrode or the reflective layer may be made of aluminum (Al), silver (Ag), nickel (Ni), or an aluminum-palladium-copper (APC) alloy.
[0092] A bank layer 3800 is formed on the planarization layer 3700 to cover the edges of the first electrodes 4100. The bank layer 3800 exposes the centers of the first electrodes 4100 in correspondence with the pixel regions.
[0093] An organic layer 4300 is formed on the first electrode 4100, and if necessary, the organic light-emitting device 4000 may have a tandem structure. For the tandem structure, refer to Figures 2 to 4 showing exemplary embodiments of the present invention and the above description thereof.
[0094] A second electrode 4200 is formed on the substrate 3010 on which the organic layer 4300 is formed. The second electrode 4200 is located in front of the display area and is made of a conductive material with a relatively low work function, and can be used as a cathode. For example, the second electrode 4200 may be made of aluminum (Al), magnesium (Mg), or an aluminum-magnesium alloy (Al-Mg).
[0095] The first electrode 4100 , the organic layer 4300 and the second electrode 4200 form an organic light emitting element 4000 .
[0096] An encapsulation film 3900 is formed on second electrode 4200 to prevent external moisture from penetrating into organic light emitting device 4000. Although not explicitly shown in FIG. 4, encapsulation film 3900 may have a triple-layer structure in which a first inorganic layer, an organic layer, and an inorganic layer are sequentially stacked, but is not limited thereto.
[0097] The following examples of the present invention will be described. However, the following examples are merely illustrative of the present invention and are not intended to limit the scope of the present invention.
[0098] Example 1 The ITO substrate was cleaned with UV ozone before use and then loaded into the evaporation system. The substrate was then transferred into a vacuum deposition chamber for deposition of any other layers on top of the substrate. -7 The following layers were deposited by evaporation from a heated boat under Torr vacuum with the following thicknesses and materials: (a) Hole injection layer (HIL): 100 Å, HATCN (b) Hole transport layer (HTL): 700 Å, HTL (c) Emission layer (EML): 300 Å, host (RHH:REH 1:1) / dopant (10%) (e) Electron transport layer (ETL): 300Å, Alq3 (f) Electron injection layer (EIL): 10Å, LiF (h) Cathode: 1000 Å, Al (aluminum)
[0099] The light-emitting layer was prepared by mixing RHH and REH in a weight ratio of 1:1 to use as a host, and doping 10% by weight of the dopant with respect to 100% by weight of the host. The host materials (RHH, REH) and dopant materials used in each example are shown in Tables 1 to 8 below.
[0100] The organic electroluminescent device was formed by depositing HIL / HTL / EML / ETL / EIL / Cathode on the ITO in this order. After depositing the layers, the device was transferred to a dry box in the deposition chamber to form a coating, and then encapsulated using UV-curable epoxy and a moisture getter. The fabricated organic electroluminescent device was 9 mm 2 The emission area is
[0101] The materials used in Example 1 above are as follows: [ka] [ka] [ka]
[0102] (Comparative Examples 1 to 4 and Examples 2 to 144) Organic light-emitting devices of Comparative Examples 1 to 4 and Examples 2 to 144 were produced in the same manner as in Example 1, except that the dopant materials and host materials shown in Tables 1 to 8 below were used. However, in Comparative Examples 1 to 4, one type of "CBP" having the following structure was used as the host in Example 1. [ka]
[0103] (Experimental example) The organic light emitting devices prepared in Examples 1 to 144 and Comparative Examples 1 to 4 were connected to an external power supply, and the device characteristics were evaluated at room temperature using a constant current source (KEITHLEY) and a photometer PR650.
[0104] Specifically, the current density of the organic light-emitting element is 10 mA / cm 2 Reference driving voltage (V), external quantum efficiency (EQE, relative value), and temperature at 40°C and 40 mA / cm 2The results of the life time (LT95, relative value) from 100% to 95% of the reference value are shown in Tables 1 to 8 below.
[0105] LT95 lifetime is the time it takes for a display element to lose 5% of its initial brightness. LT95 is the most difficult customer specification to meet and determines whether a display will experience image burn-in.
[0106] [Table 1]
[0107] [Table 2]
[0108] [Table 3]
[0109] [Table 4]
[0110] [Table 5]
[0111] [Table 6]
[0112] [Table 7]
[0113] [Table 8]
[0114] As can be seen from the results in Tables 1 to 8 above, the organic light-emitting devices in which the organometallic compound satisfying the structure represented by Chemical Formula 1 of the present invention used in Examples 1 to 144 was used as a dopant in the light-emitting layer, and a mixed material of the compound represented by Chemical Formula 2 and the compound represented by Chemical Formula 3 was used as a host, had lower driving voltages and improved external quantum efficiency (EQE) and lifetime (LT95), compared to the organic light-emitting devices in Comparative Examples 1 to 4 in which a single material was used as a host.
[0115] Although the embodiments of the present specification have been described in more detail above with reference to the accompanying drawings, the present specification is not necessarily limited to these embodiments, and various modifications may be made within the scope of the technical concept of the present specification. Therefore, the embodiments disclosed in the present specification are for illustrative purposes only, and do not limit the scope of the technical concept of the present specification. Therefore, the above-described embodiments should be understood to be illustrative in all respects and not limiting. The scope of protection of the present specification should be interpreted by the scope of the claims, and all technical concepts within the scope equivalent thereto should be interpreted as being included in the scope of the present specification. [Explanation of symbols]
[0116] 100,4000 organic light-emitting devices 110,4100 1st electrode 120,4200 2nd electrode 130,230,330,4300 organic layer 140 Hole injection layer 150 Hole transport layer 251 First hole transport layer 252 Second hole transport layer 253 Third hole transport layer 160 luminescent layer 261 First light-emitting layer 262 Second light-emitting layer 263 Third luminous layer 160',262' Dopant 160'', 262'' Hole transporting host 160''',262''' electron transport host 170 Electron transport layer 271 First hole transport layer 272 Second hole transport layer 273 Third hole transport layer 180 Electron injection layer 3000 Organic Light Emitting Display Device 3010 board 3100 Semiconductor layer 3200 Gate insulating film 3300 gate electrode 3400 Interlayer insulating film 3420 First semiconductor layer contact hole 3440 Second semiconductor layer contact hole 3520 Source Electrode 3540 Drain electrode 3600 color filters 3700 Planarization layer 3720 Drain contact hole 3800 bank layer 3900 Encapsulating Film
Claims
1. A first electrode; a second electrode facing the first electrode; an organic layer disposed between the first electrode and the second electrode; the organic layer includes an emitting layer, the emitting layer including a dopant material and a host material; The dopant material includes an organometallic compound represented by the following formula 1-7: The host material includes a compound represented by the following Chemical Formula 2 and a compound represented by the following Chemical Formula 3: 【Chemical 1】 In the above chemical formula 1-7, M is a central coordinating metal, and is iridium (Ir); Y is oxygen (O); X 1 and X 2 are different from each other, and X 1 is nitrogen (N), and X 2 is carbon (C), X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , and X 14 are each independently CR 7 and R 7 , Ra, Rb, and Rc are each independently one selected from the group consisting of hydrogen and a C1-C4 alkyl group substituted or unsubstituted with deuterium; Z 3 and Z 4 are each independently oxygen (O), R 3 , R 4 , and R 5 are each independently one selected from the group consisting of hydrogen and unsubstituted C1-C6 alkyl groups; m is a constant of 1, 2 or 3, n is a constant of 0, 1 or 2, and m+n is the oxidation number of the metal M; 【Chemistry 2】 In the above chemical formula 2, Ar each independently represents an aromatic ring group selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran, and dibenzothiophene; Ar 1 and Ar 2 are each independently a C6-C13 aryl group unsubstituted or substituted with a methyl group, or dibenzofuran; R 8 are each independently hydrogen, o is a constant of 3, each p is independently a constant of 4, q is a constant of 0, and r is a constant of 0; 【Chemistry 3】 In the above chemical formula 3, Ring A is an unsubstituted C10 aryl group; X 28 and X 29 are each independently N; L 1 is a single bond, Ar 3 is a C6-C10 aryl group, Z is the following structure: 【Chemistry 4】 W is NR 18 and R 9 ~R 13 is hydrogen, and R 18 is one selected from the group consisting of C6-C13 aryl groups substituted or unsubstituted with methyl groups; a is a constant of 6, b is a constant of 3, c is a constant of 4, d is a constant of 3, and e is a constant of 4, Organic light-emitting devices.
2. The organometallic compound represented by Chemical Formula 1-7 is one selected from the group consisting of Compounds RD-1 to RD-4 below: The organic light-emitting device according to claim 1 . 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】
3. The compound represented by Chemical Formula 2 is one selected from the group consisting of Compounds RHH-1 to RHH-6 below: The organic light-emitting device according to claim 1 . 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】
4. The compound represented by Chemical Formula 3 is one selected from the group consisting of Compounds REH-1 to REH-6 below: The organic light-emitting device according to claim 1: 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】
5. The organic layer further includes at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer. The organic light-emitting device according to claim 1 .
6. A first electrode; a second electrode facing the first electrode; a first light-emitting portion and a second light-emitting portion located between the first electrode and the second electrode; the first light-emitting unit and the second light-emitting unit each include one or more light-emitting layers; at least one of the light-emitting layers is a red phosphorescent light-emitting layer; the red phosphorescent light-emitting layer includes a dopant material and a host material, The dopant material includes an organometallic compound represented by the following formula 1-7: The host material includes a compound represented by the following Chemical Formula 2 and a compound represented by the following Chemical Formula 3: 【Chemical 21】 In the above chemical formula 1-7, M is a central coordinating metal, and is iridium (Ir); Y is oxygen (O); X 1 and X 2 are different from each other, and X 1 is nitrogen (N), and X 2 is carbon (C), X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , and X 14 are each independently CR 7 and R 7 , Ra, Rb, and Rc are each independently one selected from the group consisting of hydrogen and a C1-C4 alkyl group substituted or unsubstituted with deuterium; Z 3 and Z 4 are each independently oxygen (O), R 3 , R 4 , and R 5 are each independently hydrogen and an unsubstituted C1-C6 alkyl group; m is a constant of 1, 2 or 3, n is a constant of 0, 1 or 2, and m+n is the oxidation number of the metal M; 【Chemical 22】 In the above chemical formula 2, Ar each independently represents an aromatic ring group selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran, and dibenzothiophene; Ar 1 and Ar 2 are each independently a C6-C13 aryl group unsubstituted or substituted with a methyl group, or dibenzofuran; R 8 are each independently hydrogen, o is a constant of 3, each p is independently a constant of 4, q is a constant of 0, and r is a constant of 0; 【Chemical 23】 In the above chemical formula 3, Ring A is an unsubstituted C10 aryl group; X 28 and X 29 are each independently N; L 1 is a single bond, Ar 3 is a C6-C10 aryl group, Each Z is independently the following structure: 【Chemistry 24】 W is NR 18 and R 9 ~R 13 is hydrogen, and R 18 is a C6-C13 aryl group unsubstituted or substituted with a methyl group; a is a constant of 6, b is a constant of 3, c is a constant of 4, d is a constant of 3, and e is a constant of 4, Organic light-emitting devices.
7. The organometallic compound represented by Chemical Formula 1-7 is one selected from the group consisting of Compounds RD-1 to RD-4 below: The organic light-emitting device according to claim 6 . 【Chemistry 25】 【Chemical 26】 【Chemical 27】 【Chemical Formula 28】
8. The organometallic compound represented by Chemical Formula 2 is one selected from the group consisting of Compounds RHH-1 to RHH-6 below: The organic light-emitting device according to claim 6 . 【Chemical 29】 【Chemistry 30】 【Chemical 31】 【Chemical 32】 【Chemical 33】 【Chemical 34】
9. The organometallic compound represented by Chemical Formula 3 is one selected from the group consisting of Compounds REH-1 to REH-6 below: The organic light-emitting device according to claim 6 . 【Chemistry 35】 【Chemical 36】 【Chemical 37】 【Chemical 38】 【Chemical Formula 39】 【Chemistry 40】
10. A first electrode; a second electrode facing the first electrode; a first light-emitting portion, a second light-emitting portion, and a third light-emitting portion located between the first electrode and the second electrode; each of the first light-emitting unit, the second light-emitting unit, and the third light-emitting unit includes one or more light-emitting layers; at least one of the light-emitting layers is a red phosphorescent light-emitting layer; the red phosphorescent light-emitting layer includes a dopant material and a host material, The dopant material includes an organometallic compound represented by the following formula 1-7: The host material includes a compound represented by the following Chemical Formula 2 and a compound represented by the following Chemical Formula 3: 【Chemistry 41】 In the above chemical formula 1-7, M is a central coordinating metal, and is iridium (Ir); Y's are the same or different and each independently represents oxygen (O); X 1 and X 2 are different from each other, and X 1 is nitrogen (N), and X 2 is carbon (C), X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , and X 14 are each independently CR 7 and R 7 , Ra, Rb, and Rc are each independently one selected from the group consisting of hydrogen and a C1-C4 alkyl group substituted or unsubstituted with deuterium; Z 3 and Z 4 are each independently oxygen (O), R 3 , R 4 , and R 5 are each independently hydrogen and an unsubstituted C1-C6 alkyl group; m is a constant of 1, 2 or 3, n is a constant of 0, 1 or 2, and m+n is the oxidation number of the metal M; 【Chemistry 42】 In the above chemical formula 2, Ar each independently represents an aromatic ring group selected from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran, and dibenzothiophene; Ar 1 and Ar 2 are each independently a C6-C13 aryl group unsubstituted or substituted with a methyl group, or dibenzofuran; R 8 are each independently hydrogen, o is a constant of 3, each p is independently a constant of 4, q is a constant of 0, and r is a constant of 0; 【Chemistry 43】 In the above chemical formula 3, Ring A is an unsubstituted C10 aryl group; X 28 and X 29 are each independently N; L 1 is a single bond, Ar 3 is a C6-C10 aryl group, Each Z is independently the following structure: 【Chemical 44】 W is NR 18 and R 9 ~R 13 is hydrogen, and R 18 is one selected from the group consisting of C6-C13 aryl groups substituted or unsubstituted with methyl groups; a is a constant of 6, b is a constant of 3, c is a constant of 4, d is a constant of 3, and e is a constant of 4, Organic light-emitting devices.
11. The organometallic compound represented by Chemical Formula 1-7 is one selected from the group consisting of Compounds RD-1 to RD-4 below: The organic light-emitting device according to claim 10 . 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】
12. The organometallic compound represented by Chemical Formula 2 is one selected from the group consisting of Compounds RHH-1 to RHH-6 below: The organic light-emitting device according to claim 10 . 【Chemistry 49】 【Chemistry 50】 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemical 54】
13. The organometallic compound represented by Chemical Formula 3 is one selected from the group consisting of Compounds REH-1 to REH-6 below: The organic light-emitting device according to claim 10 . 【Chemistry 55】 【Chemical Formula 56】 【Chemical 57】 【Chemistry 58】 【Chemical Formula 59】 【Chemistry 60】
14. A substrate; a driving element located on the substrate; and an organic light-emitting device according to any one of claims 1 to 13, located on the substrate and connected to the driving element. Organic light-emitting display device.
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