Organic light-emitting device comprising an organometallic compound and multiple host materials
By using organometallic compounds as phosphorus dopant in organic light emitting equipment and combining hole transport and electronic transport host materials, the improvement space for existing equipment in efficiency and life is solved, achieving more efficient and longer life light emitting performance.
Patent Information
- Application Number
- JP2023199503
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2022-11-25
- Filing Date
- 2023-11-24
- Publication Date
- 2025-05-01
- Estimated Expiration
- 2043-11-24
AI Technical Summary
There is room for improvement in efficiency and life of existing organic light emitting devices, especially in the use of highly efficient phosphorus orescent dopant materials and host materials for optimizing photophysical properties.
The two host mixtures are formed by using organometallic compounds as phosphorus orescent dopant in the organic light emitting layer and combining two types of host materials: one as a hole transport host and the other as an electronic transport host.
Improves driving voltage, efficiency and life, and improves the overall performance of organic light emitting devices.
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Figure 0007671330000100 
Figure 0007671330000101 
Figure 0007671330000102
Abstract
Description
[Technical field]
[0001] The present invention relates to an organic light-emitting device that includes an organometallic compound and a plurality of host materials. [Background technology]
[0002] 2. Description of the Related Art Display devices are attracting increasing attention as they are applied to various fields. One of the display devices is an organic light emitting display device (OLED), and the technology thereof is rapidly developing.
[0003] An organic light emitting device is a device that, when electric charges are injected into an emission layer formed between a positive electrode and a negative electrode, electrons and holes combine to form excitons, and then emit the energy of the excitons as light. Organic light emitting diodes can be driven at a low voltage compared to existing display technologies, consume less power, and have excellent color sense. 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 better viewing angles and light-to-dark ratios than liquid crystal displays (LCDs), do not require backlights, and can be made lightweight and ultra-thin. Organic light emitting diodes are formed by disposing 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 fall to the ground state, emitting light.
[0006] Organic materials used in organic light-emitting devices can be broadly classified into luminescent materials and charge transport materials. The luminescent material is an important factor that determines the luminous efficiency of organic light-emitting devices, and it must have high quantum efficiency and excellent electron and hole mobility, and must be present uniformly and stably in the luminescent layer. Luminescent materials are classified into blue, red, green, etc., depending on the color of light they emit, and 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, the singlets, are used to generate light, and the remaining 75% of the triplets are almost entirely lost to heat. In contrast, phosphorescent materials have a light-emitting mechanism that converts both singlets and triplets into light.
[0008] Conventionally, organic metal compounds have been used as phosphorescent light-emitting materials in organic light-emitting devices. In order to improve the efficiency and life span 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 a host of optimal photophysical properties. Summary of the Invention [Problem to be solved by the invention]
[0009] SUMMARY OF THE PRESENTLY PREFERRED EMBODIMENTS 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 life span.
[0010] The object of the present invention is not limited to the object mentioned above, and other objects and advantages of the present invention not mentioned can be understood from the following description and can be more clearly understood from the embodiments of the present invention. Also, it can be easily understood that the object and advantages of the present invention can be realized by the means and combinations thereof as 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; the organic layer includes an emitting layer, the emitting layer includes a dopant material and a host material, the dopant material includes an organometallic compound represented by Chemical Formula 1 below, and the host material includes a compound represented by Chemical Formula 2 below and a compound represented by Chemical Formula 3 below.
[0012] [ka]
[0013] In the above 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); R is X 1 and X 2 may be linked to form a fused ring structure, X 1 and X 2 are carbons; R 1 and R 2each independently represents a hydrogen atom, a deuterium atom, a halogen atom, 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 R may be one selected from the group consisting of a 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; 1 and R 2 together can form a C5-C6 carbocyclic ring, a C3-C6 heterocyclic ring, or a C7-C10 arylalkyl group; Y is BR 3 , C.R. 3 R 4 , C=O, CNR 3 , SiR 3 R 4 , N.R. 3 , P.R. 3 , AsR 3 , SbR 3 , P(O)R 3 , P(S)R 3 , P(Se)R 3 , As(O)R 3 , As(S)R 3 , As(Se)R 3 , Sb(O)R 3 , Sb(S)R 3 , Sb(Se)R 3 , O, S, Se, Te, SO, SO 2 , SeO, SeO 2 , TeO, and TeO 2 may be one selected from the group consisting of: R 3 and R 4 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, 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 ... 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; X 3 ~X 6 are each independently CR 5 and N; X 3 ~X 6 adjacent substituents may be fused to form a ring, which may be a C5-C6 carbon ring or a C3-C6 heterocyclic ring; X 7 ~X 10 are each independently CR 6 and N; R 5 and R 6each independently represents a hydrogen atom, a deuterium atom, a halogen atom, 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 ... 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; TIFF0007671330000002.tif25170 may be a bidentate ligand; m may be a constant equal to 1, 2 or 3, n may be a constant equal to 0, 1 or 2, and m+n may be the oxidation number of the metal M;
[0014] [ka]
[0015] In the above formula 2, Each Ar may independently be a substituted or unsubstituted aromatic ring group derived from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran, and dibenzothiophene; Ar 1 and Ar 2 may each independently be a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; R 7each independently represents a hydrogen atom, a deuterium atom, a halogen atom, 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 ... 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; o may be a constant of 0, 1, 2 or 3, p may be each independently 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; 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;
[0016] [ka]
[0017] In the above formula 3, The A ring may be a substituted or unsubstituted C6-C30 aryl group; X 11 and X 12 may each independently be N or CR'; L 1may 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; Ar 3 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; The Ar 3 One or more hydrogen atoms of the alkyl group, aryl group, heteroaryl group, silylalkyl group, or silylaryl group represented by the formula (I) can be substituted with one or more deuterium and halogen atoms; Z may be one selected from the group consisting of the following structures:
[0018] TIFF0007671330000005.tif86170
[0019] W is O, S, NR 17 , C.R. 17 R 18 , and SiR 17 R 18 may be one selected from the group consisting of: R 8 ~R 18and R' are each independently 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 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 are each independently a constant of 1, 2, 3, or 4; b, d, and g are each independently a constant of 1, 2, or 3; f is a constant of 1, 2, 3, 4, 5, or 6; and h is a constant of 1, 2, 3, 4, or 5.
[0020] According to another aspect of the present invention, an organic light emitting display device including the organic light emitting device according to the aspect of the present invention may be provided.
[0021] In the organic light emitting device according to the present invention, the organometallic compound represented by Chemical formula 1 is used as a phosphorescent dopant, and a mixture of the compound represented by Chemical formula 2 and the compound represented by Chemical formula 3 is used as a phosphorescent host, thereby improving the driving voltage, efficiency and lifespan of the organic light emitting device.
[0022] 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 description of the drawings]
[0023] [Figure 1] 1 is a cross-sectional view illustrating an organic light emitting device according to an embodiment of the present invention. [Diagram 2] 1 is a cross-sectional view illustrating a schematic configuration of an organic light emitting device having a tandem structure including two light emitting units according to an embodiment of the present invention. [Diagram 3] 1 is a cross-sectional view illustrating a schematic configuration of 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 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 PREFERRED EMBODIMENTS
[0024] The above-mentioned objects, features and advantages will be described in detail below with reference to the accompanying drawings, so that a person having ordinary skill in the art to which the present invention pertains can easily implement the technical idea of the present invention. In describing the present invention, detailed descriptions of known techniques according to the present invention will be omitted if they are deemed to obscure the gist of the present invention. 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.
[0025] In describing this specification, if a detailed description of related publicly known technology is deemed to obscure the gist of this specification, the detailed description will be omitted.
[0026] In this specification, when a component is described as "comprising," "having," "consisting," "disposed," "equipped," etc., other parts can be added unless "only" is used. When a component is described in the singular, it includes the plural unless otherwise expressly stated.
[0027] When interpreting the elements in this specification, unless otherwise expressly stated, they are to be interpreted as including a margin of error.
[0028] In this specification, when an arbitrary structure is disposed on the "top (or bottom)" of a component or "above (or below)" a component, it means not only that the arbitrary structure is disposed in contact with the upper surface (or lower surface) of the component, but also that other structures may be interposed between the component and the arbitrary structure disposed on (or below) the component.
[0029] The term "halo" or "halogen" as used herein includes fluorine, chlorine, bromine, and iodine.
[0030] In this specification, the organometallic compound represented by Chemical formula 1, the compound represented by Chemical formula 2, and the compound represented by Chemical formula 3 may each include a case in which some or all of the hydrogen atoms are replaced with deuterium.
[0031] 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.
[0032] 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.
[0033] 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.
[0034] The term "alkynyl group" as used herein 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.
[0035] As used herein, the terms "aralkyl group" or "arylalkyl group" are used interchangeably to refer to an alkyl group having an aromatic group as a substituent, and further the alkylaryl group may be optionally substituted.
[0036] The terms "aryl group" and "aromatic group" used herein are used interchangeably, and aryl groups include both monocyclic and polycyclic groups. Polycyclic rings may include "fused rings" in which two or more rings have two carbons common to both adjacent rings. Unless otherwise specified, aryl groups contain 6 to 60 carbon atoms, and further, aryl groups may be optionally substituted.
[0037] 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 of the carbon atoms constituting the group is substituted with a heteroatom such as oxygen (O), nitrogen (N) or sulfur (S), and the heterocycle can be optionally substituted.
[0038] As used herein, the term "carbon ring" can be used to include both a "cycloalkyl group" which is a ring group and an "aryl group (aromatic group)" which is an aromatic ring group, unless otherwise specified.
[0039] The terms "heteroalkyl group" and "heteroalkenyl group" used herein mean a group in which one or more of the carbon atoms constituting the group are replaced with a heteroatom such as oxygen (O), nitrogen (N) or sulfur (S), and the heteroalkyl group and heteroalkenyl group can be further optionally substituted.
[0040] The term "substituted" as used herein means that a substituent other than hydrogen (H) is bonded to the carbon. Unless otherwise defined in the present specification, 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, but the present invention is not limited thereto.
[0041] Each object and substituent defined herein may be the same or different, unless otherwise stated.
[0042] The structure of the organometallic compound according to the present invention and the organic light-emitting device including the same will be described in detail below.
[0043] Conventionally, organometallic compounds have been used as dopants for phosphorescent light-emitting layers, and for example, 2-phenylpyridine is known as a main ligand structure of organometallic compounds. However, these conventional light-emitting dopants have limitations in improving the efficiency and lifespan of organic light-emitting devices, and it was necessary to develop new light-emitting dopant materials. It was experimentally confirmed that the efficiency and lifespan of organic light-emitting devices can be further increased and the driving voltage can be reduced by mixing a hole transport type host and an electron transport type host as host materials with the dopant material, thereby improving the characteristics of the organic light-emitting devices, and the present invention was completed.
[0044] Specifically, referring to FIG. 1 according to an embodiment of the present invention, an organic light emitting device 100 may be provided, which 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 emission layer 160, which may include a dopant material 160' and a host material 160", 160'", and the dopant material may include an organometallic compound 160' represented by Chemical Formula 1 below, and 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.
[0045] [ka]
[0046] In the above 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); R is X 1 and X 2 may be linked to form a fused ring structure, X 1 and X 2 are carbons; R 1 and R 2each independently represents a hydrogen atom, a deuterium atom, a halogen atom, 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 R may be one selected from the group consisting of a 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; 1 and R 2 together can form a C5-C6 carbocyclic ring, a C3-C6 heterocyclic ring, or a C5-C10 arylalkyl group; Y is BR 3 , C.R. 3 R 4 , C=O, CNR 3 , SiR 3 R 4 , N.R. 3 , P.R. 3 , AsR 3 , SbR 3 , P(O)R 3 , P(S)R 3 , P(Se)R 3 , As(O)R 3 , As(S)R 3 , As(Se)R 3 , Sb(O)R 3 , Sb(S)R 3 , Sb(Se)R 3 , O, S, Se, Te, SO, SO 2 , SeO, SeO 2 , TeO, and TeO 2 may be one selected from the group consisting of: R 3 and R 4 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, 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 ... 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; X 3 ~X 6 are each independently CR 5 and N; X 3 ~X 6 adjacent substituents may be fused to form a ring, which may be a C5-C6 carbon ring or a C3-C6 heterocyclic ring; X 7 ~X 10 are each independently CR 6 and N; R 5 and R 6each independently represents a hydrogen atom, a deuterium atom, a halogen atom, 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 ... 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; TIFF0007671330000007.tif25170 may be a bidentate ligand; m may be a constant equal to 1, 2 or 3, n may be a constant equal to 0, 1 or 2, and m+n may be the oxidation number of the metal M;
[0047] [ka]
[0048] In the above formula 2, Each Ar may independently be a substituted or unsubstituted aromatic ring group derived from the group consisting of benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran, and dibenzothiophene; Ar 1 and Ar 2 may each independently be a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; R 7each independently represents a hydrogen atom, a deuterium atom, a halogen atom, 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 ... 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; o may be a constant of 0, 1, 2 or 3, p may be each independently 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; 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;
[0049] [ka]
[0050] In the above formula 3, The A ring may be a substituted or unsubstituted C6-C30 aryl group; X 11 and X 12 may each independently be N or CR'; L 1may 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; Ar 3 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; The Ar 3 One or more hydrogen atoms of the alkyl group, aryl group, heteroaryl group, silylalkyl group, or silylaryl group represented by the formula (I) can be substituted with one or more deuterium and halogen atoms; Z may be one selected from the group consisting of the following structures:
[0051] TIFF0007671330000010.tif86170
[0052] W is O, S, NR 17 , C.R. 17 R 18 , and SiR 17 R 18 may be one selected from the group consisting of: R 8 ~R 18and R' are each independently 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 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 are each independently a constant of 1, 2, 3, or 4; b, d, and g are each independently a constant of 1, 2, or 3; f is a constant of 1, 2, 3, 4, 5, or 6; and h is a constant of 1, 2, 3, 4, or 5.
[0053] According to one embodiment of the present invention, in the above formula 1, R 1 and R 2 can be selectively substituted with deuterium and / or halogen.
[0054] According to one embodiment of the present invention, in the above formula 1, R 5 and R 6 can be selectively substituted with deuterium and / or halogen.
[0055] According to one embodiment of the present invention, in the above formula 3, R 8 ~R 18 and R' can be optionally substituted with at least one of deuterium and / or halogen.
[0056] According to one embodiment of the present invention, the organometallic compound represented by the above formula 1 may be 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.
[0057] According to one embodiment of the present invention, Y in the above formula (1) is O, S, or CR. 3 R 4 It may be one selected from the group consisting of:
[0058] According to one embodiment of the present invention, the organometallic compound represented by the above 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 formula 1.
[0059] TIFF0007671330000011.tif210170 TIFF0007671330000012.tif204170 TIFF0007671330000013.tif210170 TIFF0007671330000014.tif217170 TIFF0007671330000015.tif230170 TIFF0007671330000016.tif235170 TIFF0007671330000017.tif80170TIFF0007671330000018.tif70170.
[0060] According to one embodiment of the present invention, in the above formula 2, Ar 1 and Ar 2 may each independently be one derived from the group consisting of benzene, naphthalene, phenanthrene, fluorene, dibenzofuran, dibenzothiophene, and spirobifluorene, wherein the Ar 1and Ar 2 each independently represents the Ar 1 and Ar 2 One or more of the hydrogen atoms can be substituted with one or more selected from the group consisting of deuterium, a halogen atom, a C1-C10 alkyl group, a cyano group, and a silyl group.
[0061] According to one embodiment of the present invention, the organometallic compound represented by the above 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 formula 2.
[0062] TIFF0007671330000019.tif228170 TIFF0007671330000020.tif222170 TIFF0007671330000021.tif207170TIFF0007671330000022.tif71170 and TIFF0007671330000023.tif73170.
[0063] According to one embodiment of the present invention, X in the above formula 3 11 and X 12 can be selected to be N, respectively.
[0064] According to one embodiment of the present invention, the organometallic compound represented by Chemical formula 3 above 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 Chemical formula 3 above.
[0065] TIFF0007671330000024.tif238170TIFF0007671330000025.tif250170 TIFF0007671330000026.tif171170 TIFF0007671330000027.tif184170 TIFF0007671330000028.tif248170 TIFF0007671330000029.tif181170 TIFF0007671330000030.tif95170TIFF0007671330000031.tif91170 and TIFF0007671330000032.tif73170.
[0066] 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 a hole injection layer 140 (HIL), a hole transfer layer 150 (HTL), an emission material layer 160 (EML), an electron transfer layer 170 (ETL), and an electron injection layer 180 (EIL) in this order from the first electrode 110. The second electrode 120 may be formed on the electron injection layer 180, and a protective film (not shown) may be formed thereon.
[0067] 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 having good hole transport properties, and adjusts hole injection properties by reducing the HOMO energy level difference between the hole transport layer 150 and the light emitting layer 160, thereby reducing the accumulation of holes at the interface between the hole transport auxiliary layer and the light emitting layer 160, and reducing the quenching phenomenon in which excitons disappear due to polarons at the interface. This reduces the deterioration phenomenon of the device, stabilizes the device, and improves efficiency and life.
[0068] 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 (indium tin oxide), IZO (indium zinc oxide), tin oxide, or zinc oxide, but is not limited thereto.
[0069] The second electrode 120 may be a negative electrode and may include, but is not limited to, conductive materials having relatively low work function values, such as Al, Mg, Ca, Ag, or alloys or combinations thereof.
[0070] The hole injection layer 140 may be located between the first electrode 110 and the hole transport layer 150. The hole injection layer 140 has a function of improving the interface characteristics 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 be selected from a group consisting of mMTDATA (4,4',4''-tris[phenyl(m-tolyl)amino]triphenylamine), CuPc (copper(II)phthalocyanine), TCTA (tris(4-carbazoyl-9-ylphenyl)amine), HATCN (1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile), TDAPB (1,3,5-tris(4-(2,2'-dipyridylamino)phenyl)benzene), PEDOT / PSS (poly(3,4-ethylenedioxythiophene)polystyrene). The compound may include, but is not limited to, N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine), and preferably, N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine).
[0071] The hole transport layer 150 is located adjacent to the light emitting layer between the first electrode 110 and the light emitting layer 160. The hole transport layer 150 may include a compound such as TPD (N,N'-Bis(3-methylphenyl)-N,N'-diphenylbenzidine), NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), CBP (carbazole biphenyl), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl)-4-amine, and preferably includes NPB, but is not limited thereto.
[0072] According to an 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' in order to improve the light emitting efficiency of the host 160'', 160''' and the device, and the dopant 160' may be a material that emits green or red light, and preferably a green phosphorescent material.
[0073] According to an 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'''', and, although not limited thereto, the doping concentration may be, for example, 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 %.
[0074] According to an embodiment of the present invention, the mixing ratio of the two hosts 160'', 160''' is not particularly limited, and the host 160'' which is a compound represented by Chemical formula 2 has a hole transporting property, and the host 160'' which is a compound represented by Chemical formula 3 has an electron transporting property. Therefore, by mixing the two hosts, it is possible to obtain an advantage that the efficiency and life characteristics are increased, and the mixing ratio of the two hosts can be appropriately adjusted. Therefore, the mixing ratio of the two hosts obtained by mixing the compound represented by Chemical formula 2 and the compound represented by Chemical formula 3 is not particularly limited, and the ratio (weight basis) of the compound represented by Chemical formula 2: 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.
[0075] In addition, an electron transport layer 170 and an electron injection layer 180 may be sequentially laminated 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 can stably supply electrons to the light emitting layer by smooth electron transport.
[0076] For example, the material of the electron transport layer 170 is any material commonly used in the art, such as Alq 3(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)aluminium), SAlq, TPBi(2,2',2-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzim) idazole, oxadiazole, triazole, phenanthroline, benzoxazole, benzothiazole, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole and other compounds, preferably 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, but is not limited thereto.
[0077] The electron injection layer 180 serves to facilitate the injection of electrons. The material of the electron injection layer is a material commonly used in the art, for example, Alq 3 The electron injection layer 180 may include, but is not limited to, compounds such as tris(8-hydroxyquinolino)aluminum, PBD, TAZ, spiro-PBD, BAlq, and SAlq. Alternatively, the electron injection layer 180 may be comprised of a metal compound, such as, for example, Liq, LiF, NaF, KF, RbF, CsF, FrF, and BeF. 2 , MgF 2 , CaF 2 , SrF2 , BaF 2 , RaF 2 These may include, but are not limited to, the following:
[0078] 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 the tandem organic light emitting device according to an embodiment of the present invention, a single light emitting stack (or light emitting portion) may be formed of a structure in which two or more are connected by a charge generation layer (CGL). The organic light emitting device may include a first electrode and a second electrode facing each other on a substrate, and two or more light emitting stacks (light emitting portions) having a light emitting layer stacked between the first and second electrodes and emitting light of a specific wavelength band. The plurality of light emitting stacks (light emitting portions) may be adapted to emit the same color or different colors. Also, one light emitting stack (light emitting portion) may include one or more light emitting layers, and the plurality of light emitting layers may be light emitting layers of the same color or different colors.
[0079] At this time, one or more of the light emitting layers included in the plurality of light emitting parts may contain the organometallic compound represented by Chemical Formula 1 according to the present invention as a dopant material. The plurality of light emitting parts in the tandem structure may be connected to a charge generation layer (CGL) consisting of an N-type charge generation layer and a P-type charge generation layer.
[0080] 2 and 3 are cross-sectional views illustrating schematic configurations of tandem-structured organic light-emitting devices having two and three light-emitting portions, respectively, according to illustrative embodiments of the present invention.
[0081] 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.
[0082] As shown in FIG. 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 located between the first electrode 110 and the second electrode 120; 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; 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. At least one 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 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. 3, each of the first, second, and third light emitting units (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 may be formed of a plurality of light emitting layers.
[0083] Furthermore, the organic light emitting device according to an embodiment of the present invention may include 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.
[0084] The organic light emitting device according to the present invention may be used in an organic light emitting display device, a lighting device using the organic light emitting device, etc. As an embodiment, FIG 4 is a cross-sectional view illustrating an organic light emitting display device using an organic light emitting device according to an exemplary embodiment of the present invention.
[0085] 4, an organic light emitting display device 3000 may include a substrate 3010, an organic light emitting device 4000, and an encapsulation film 3900 covering the organic light emitting device 4000. A driving thin film transistor (Td) serving as a driving element and an organic light emitting device 4000 connected to the driving thin film transistor (Td) are positioned on the substrate 3010.
[0086] 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.
[0087] 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.
[0088] 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, and the light-shielding pattern prevents light from being incident on the semiconductor layer 3100 to prevent the semiconductor layer 3100 from being deteriorated by light. Alternatively, the semiconductor layer 3100 may be made of polycrystalline silicon, and in this case, both edges of the semiconductor layer 3100 may be doped with impurities.
[0089] 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.
[0090] A gate electrode 3300 made of a conductive material such as metal is formed on the gate insulating layer 3200 in correspondence with the center of the semiconductor layer 3100. The gate electrode 3300 is connected to a switching thin film transistor.
[0091] An interlayer insulating film 3400 made of an insulating material is formed on the front surface of the substrate 3010 on top of 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.
[0092] 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.
[0093] 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 with respect to 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).
[0094] 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 the top of the semiconductor layer 3100.
[0095] Alternatively, the driving thin film transistor (Td) may have an inverted staggered structure in which a gate electrode is located under a semiconductor layer and a source electrode and a drain electrode are located over 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).
[0096] 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, red, green, and blue color filter patterns that absorb light may be formed separately for each pixel region, and each of these color filter patterns may be disposed overlapping with an organic layer 4300 of the organic light emitting element 4000 that emits light of a wavelength band to be absorbed. By employing the color filter 3600, the organic light emitting display 3000 may implement full color.
[0097] For example, when the organic light emitting display device 3000 is a bottom-emission type, the color filter 3600 for absorbing light may be located on the interlayer insulating film 3400 corresponding to the organic light emitting element 4000. In an exemplary embodiment, when 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. As an example, the color filter 3600 may be formed to a thickness of 2 to 5 μm.
[0098] 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).
[0099] A first electrode 4100 connected to a drain electrode 3540 of the driving thin film transistor (Td) through a drain contact hole 3720 is formed on the planarization layer 3700 and separated for each pixel region.
[0100] The first electrode 4100 may be an anode and may be made of a conductive material having a relatively large work function value, for example, the first electrode 4100 may be made of a transparent conductive material such as ITO, IZO, or ZnO.
[0101] 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 any one of aluminum (Al), silver (Ag), nickel (Ni), and an aluminum-palladium-copper (APC) alloy.
[0102] 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.
[0103] An organic layer 4300 is formed on the first electrode 4100, and if necessary, the organic light-emitting element 4000 may have a tandem structure. For the tandem structure, refer to Figures 2 to 4 showing exemplary embodiments of the present invention and the above description thereof.
[0104] 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 small work function value, 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).
[0105] The first electrode 4100 , the organic layer 4300 and the second electrode 4200 form an organic light emitting element 4000 .
[0106] An encapsulation film 3900 is formed on the second electrode 4200 to prevent external moisture from penetrating into the organic light emitting device 4000. Although not explicitly shown in FIG 4, the encapsulation film 3900 may have a triple layer structure in which a first inorganic layer, an organic layer, and an inorganic layer are sequentially stacked, but is not limited thereto.
[0107] Hereinafter, 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 present invention.
[0108] 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:
[0109] (a) Hole injection layer (HIL): 100 Å, HATCN (b) Hole transport layer (HTL): 700 Å, HTL (c) Emitting layer (EML): 300 Å, host (RHH:REH1:1) / dopant (10%) (e) Electron transport layer (ETL): 300Å, Alq 3 (f) Electron injection layer (EIL): 10Å, LiF (h) Cathode: 1000 Å, Al (aluminum)
[0110] 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 a 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.
[0111] The organic electroluminescent device was formed by depositing HIL / HTL / EML / ETL / EIL / Cathode in this order on the ITO. After depositing the layers, the device was transferred to a dry box in the deposition chamber to form a coating, and then encapsulation was performed using UV curable epoxy and a moisture getter. The organic electroluminescent device thus manufactured was 9 mm thick. 2 The emission area is .
[0112] The materials used in Example 1 above are as follows:
[0113] TIFF0007671330000033.tif174170
[0114] Comparative Examples 1 to 4 and Examples 2 to 144 Except for using the dopant materials and host materials shown in the following Tables 1 to 8, 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. However, in Comparative Examples 1 to 4, one type of "CBP" having the following structure was used as the host in the above-mentioned Example 1.
[0115] TIFF0007671330000034.tif32170
[0116] 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 supply (KEITHLEY) and a photometer PR650.
[0117] Specifically, the current density of the organic light-emitting element is 10 mA / cm 2 The reference 7 drive voltage (V), external quantum efficiency (EQE, relative value), and 40°C and 40mA / cm 2 The results of the life time from 100% to 95% (LT95, relative value) are shown in Tables 1 to 8 below.
[0118] 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.
[0119] [Table 1]
[0120] [Table 2]
[0121] [Table 3]
[0122] [Table 4]
[0123] [Table 5]
[0124] [Table 6]
[0125] [Table 7]
[0126] [Table 8]
[0127] As can be seen from the results of 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 a lower driving voltage, and improved external quantum efficiency (EQE) and lifetime (LT95) compared to the organic light-emitting devices of Comparative Examples 1 to 4 in which a single material was used as a host.
[0128] Although the embodiments of the present specification have been described in detail above with reference to the accompanying drawings, the present specification is not necessarily limited to these embodiments, and various modifications can be made within the scope of the technical idea of the present specification. Therefore, the embodiments disclosed in the present specification are for illustration purposes, not for the purpose of limiting the technical idea of the present specification, and the scope of the technical idea of the present specification is not limited by these embodiments. Therefore, it should be understood that the above-mentioned embodiments are illustrative in all respects and not limiting. The scope of protection of the present specification should be interpreted according to the scope of the claims, and all technical ideas within the scope equivalent thereto should be interpreted as being included in the scope of the rights of the present specification. [Explanation of symbols]
[0129] 100,4000 Organic light-emitting device 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 Light-emitting layer 261 First light-emitting layer 262 Second light-emitting layer 263 Third luminous layer 160',262' Dopant material 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 Substrate 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. first electrode; a second electrode facing the first electrode; and An organic layer disposed between the first electrode and the second electrode. An organic light-emitting device comprising: the organic layer comprises an emitting layer, the emitting layer comprises a dopant material and a host material; The dopant material is the following compounds RD-1 to RD-20: At least one organometallic compound selected from the group consisting of The host material is The following compounds RHH-1 to RHH-20: At least one compound selected from the group consisting of: The following compounds REH-1 to REH-20: At least one compound selected from the group consisting of Including, Organic light-emitting devices.
2. The organic light emitting device according to claim 1 , wherein the organic layer further comprises at least one selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.
3. first electrode; a second electrode facing the first electrode; and A first light emitting portion and a second light emitting portion are located between the first electrode and the second electrode. An organic light-emitting device comprising: Each of the first light-emitting unit and the second light-emitting unit includes at least one light-emitting layer including a red phosphorescent light-emitting layer, the red phosphorescent emitting layer includes a dopant material and a host material, The dopant material is the following compounds RD-1 to RD-20: The organometallic compound is represented by at least one selected from the group consisting of The host material is The following compounds RHH-1 to RHH-20: At least one compound selected from the group consisting of: The following compounds REH-1 to REH-20: At least one compound selected from the group consisting of Including, Organic light-emitting devices.
4. first electrode; a second electrode facing the first electrode; and 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; An organic light-emitting device comprising: Each of the first light-emitting unit, the second light-emitting unit, and the third light-emitting unit includes at least one red phosphorescent light-emitting layer; the red phosphorescent emitting layer includes a dopant material and a host material, The dopant material is the following compounds RD-1 to RD-20: At least one organometallic compound selected from the group consisting of The host material is The following compounds RHH-1 to RHH-20: At least one compound selected from the group consisting of: The following compounds REH-1 to REH-20: At least one compound selected from the group consisting of Including, Organic light-emitting devices.
5. substrate; An actuation element located on the substrate; and The organic light-emitting device according to any one of claims 1 to 4, which is located on the substrate and connected to the driving element. An organic light-emitting display device comprising:
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