Organic light emitting diode and organic light emitting device having the same

Abstract

The present disclosure relates to an organic light emitting diode (OLED) in which at least one light emitting material layer includes a dopant and a double carbazole-based material and / or an azine-based material having a structure of Formula 1 below, at least one hole transport layer includes a spirobifluorene-based material, and at least one electron transport layer includes a benzimidazole-based material, and an organic light emitting device including the same. The OLED and the organic light emitting device including the host and the dopant can improve luminous efficiency and luminous lifespan thereof.[Formula 1] Ir(L A ) m (L B ) n .

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2021-0165810, filed in Korea on November 26, 2021, the entire contents of which are hereby incorporated herein. Technical Field

[0003] This disclosure relates to an organic light-emitting diode (OLED). For example, an OLED that may have improved luminous efficiency and luminous lifetime, and an organic light-emitting device including the OLED. Background Technology

[0004] Flat panel displays, including those using organic light-emitting diodes (OLEDs), have attracted attention as potential replacements for liquid crystal displays (LCDs). OLEDs can be formed into sizes smaller than... The organic thin film and electrode configuration can achieve unidirectional or bidirectional images. Furthermore, OLEDs can even be formed on flexible transparent substrates such as plastic substrates, thus enabling the easy realization of flexible or foldable display devices. In addition, OLEDs can be driven at lower voltages, and compared to LCDs, OLEDs have advantageous high color purity.

[0005] Because fluorescent materials utilize only singlet exciton energy during luminescence, existing fluorescent materials exhibit low luminescence efficiency. Conversely, phosphorescent materials, utilizing both triplet and singlet exciton energies, can exhibit higher luminescence efficiency. However, examples of phosphorescent materials include metal complexes, which have short luminescence lifetimes in commercial applications. Therefore, there is still a need to develop luminescent compounds or organic light-emitting diodes that can improve both luminescence efficiency and lifetime. Summary of the Invention

[0006] Therefore, embodiments of this disclosure relate to organic light-emitting diodes and organic light-emitting devices, which substantially eliminate one or more problems arising from the limitations and disadvantages of the prior art.

[0007] One aspect of this disclosure is to provide an organic light-emitting diode (OLED) that can have improved luminous efficiency and luminous lifetime. Another aspect of this disclosure is to provide an organic light-emitting device including the OLED.

[0008] Additional features and aspects will be set forth in the following description, some of which will become apparent from the specification or may be learned by practicing the disclosed concepts provided herein. Other features and aspects of the disclosed concepts may be realized and obtained by means of structures specifically pointed out in or derived therefrom, as well as by the claims and drawings thereof.

[0009] To achieve these and other aspects of the inventive concept, as specifically and broadly described, in one aspect, this disclosure provides an organic light-emitting diode (OLED) comprising: a first electrode; a second electrode facing the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode, the light-emitting layer comprising at least one light-emitting material layer, at least one hole transport layer disposed between the first electrode and the at least one light-emitting material layer, and at least one electron transport layer disposed between the at least one light-emitting material layer and the second electrode, wherein the at least one light-emitting material layer comprises a host and a dopant, the host comprising: a first host represented by a structure of Formula 7, and a second host represented by a structure of Formula 9, the dopant comprising an organometallic compound represented by a structure of Formula 1, wherein the at least one hole transport layer comprises an organic compound represented by a structure of Formula 11, and wherein the at least one electron transport layer comprises an organic compound represented by a structure of Formula 13.

[0010] in,

[0011] Equation 1 is:

[0012] [Formula 1]

[0013] Ir(L A ) m (L B ) n

[0014] In Equation 1,

[0015] L A It has a structure represented by Equation 2;

[0016] L B It is an auxiliary ligand represented by the structure of Equation 3;

[0017] m is 1, 2, or 3;

[0018] n is 0, 1, or 2; and

[0019] m+n is 3;

[0020] Equation 2 is:

[0021] [Equation 2]

[0022]

[0023] In Equation 2,

[0024] X1 and X2 are each independently CR7 or N;

[0025] X3 to X5 are each independently CR8 or N, and at least one of X3 to X5 is CR8;

[0026] X6 to X9 are each independently CR9 or N, and at least one of X6 to X9 is CR9;

[0027] When two adjacent groups among R1 to R5, and / or

[0028] When b is an integer of 2 or greater, two adjacent R6, and / or

[0029] X3 and X4 or X4 and X5, and / or

[0030] X6 and X7, X7 and X8, or X8 and X9

[0031] When no loop is formed,

[0032] R1 to R9 are each independently hydrogen, protium, deuterium, undeuterated or deuterated unsubstituted or substituted C1-C. 20 Alkyl, undeuterated or deuterated, unsubstituted or substituted C1-C 20 Heteroalkyl, undeuterated or deuterated, unsubstituted or substituted C2-C 20 Alkenyl, undeuterated or deuterated, unsubstituted or substituted C2-C 20 Heterene, undeuterated or deuterated, unsubstituted or substituted C1-C 20 Alkoxy, carboxyl, nitrile, isonitrile, sulfonamide, phosphine, undeuterated or deuterated unsubstituted or substituted C1-C 20 Alkylamino, undeuterated or deuterated, unsubstituted or substituted C1-C 20 Alkyl silyl, undeuterated or deuterated, unsubstituted or substituted C4-C 30 Alicyclic group, undeuterated or deuterated, unsubstituted or substituted C3-C 30 Heterocyclic group, undeuterated or deuterated unsubstituted or substituted C6-C 30 Aryl, or undeuterated or deuterated unsubstituted or substituted C3-C 30 Heteroaryl, wherein when b is 2, 3 or 4, each R6 is the same or different from each other;

[0033] Optionally,

[0034] Two adjacent groups from R1 to R5, and / or

[0035] When b is 2, 3, or 4, two adjacent R6, and / or

[0036] X3 and X4 or X4 and X5, and / or

[0037] X6 and X7, X7 and X8, or X8 and X9

[0038] Further, directly or indirectly, they are linked together to form unsubstituted or substituted C4-C. 20 Alicyclic, unsubstituted or substituted C3-C 20 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Mixed fragrance ring;

[0039] a is 0, 1, or 2; and

[0040] b is 0, 1, 2, 3, or 4.

[0041] Equation 3 is:

[0042] [Formula 3]

[0043]

[0044] Equation 7 is:

[0045] [Formula 7]

[0046]

[0047] In Equation 7,

[0048] R 41 To R 44 Each is independently either unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 Heteroaryl, wherein when p is 2, 3, 4, 5, 6 or 7, each R 43 Whether they are the same or different, each R is equal to or different when q is 2, 3, 4, 5, 6 or 7. 44 Whether they are the same or different, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; and

[0049] p and q are each independently 0, 1, 2, 3, 4, 5, 6 or 7.

[0050] Equation 9 is:

[0051] [Formula 9]

[0052]

[0053] In Equation 9,

[0054] R 51 and R 52 Each is independently unsubstituted or substituted C6-C 30 aryl or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0055] Y1, Y2, and Y3 are each independently CR 53 Or N, where at least one of Y1, Y2, and Y3 is N;

[0056] R 53 Independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0057] R 61 To R 68 Each is independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 10 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 The heterocyclic aromatic rings form a spiral structure.

[0058] Optionally,

[0059] R 61 To R 68Two adjacent groups in the form are further directly or indirectly linked together to form an unsubstituted or substituted C6-C. 30 Aromatic ring, or unsubstituted or substituted C3-C 30 heterocyclic aromatic rings, optionally, unsubstituted or substituted C6-C 30 Aromatic rings and unsubstituted or substituted C3-C 30 Each heterocyclic ring independently interacts with unsubstituted or substituted C6-C. 20 Aromatic ring, or unsubstituted or substituted C3-C 20 Heteroaromatic rings form a spiral structure;

[0060] R 69 and R 70 Each is independently unsubstituted or substituted C1-C 10 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a helical structure, wherein when j is 2 or 3, each R 69 They are either the same or different, and when k is 2 or 3, each R 70 Whether they are the same or different,

[0061] Optionally,

[0062] When j is 2 or 3, two adjacent R 69 and / or

[0063] When k is 2 or 3, two adjacent R 70

[0064] Further, directly or indirectly, they are linked together to form unsubstituted or substituted C6-C. 30 Aromatic ring, or unsubstituted or substituted C3-C 30 heterocyclic aromatic rings, optionally, unsubstituted or substituted C6-C 30 Aromatic rings and unsubstituted or substituted C3-C 30 Each heterocyclic ring independently interacts with unsubstituted or substituted C6-C. 20 Aromatic ring, or unsubstituted or substituted C3-C 20 Heteroaromatic rings form a spiral structure;

[0065] L represents a single bond, and is either unsubstituted or substituted C6-C. 30 Aryl styrene, or unsubstituted or substituted C3-C 30Hybrid aromatic styrene, optionally, unsubstituted or substituted C6-C 30 Aryl styrene and unsubstituted or substituted C3-C 30 Each heteroarylene independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0066] Z is either O or S; and

[0067] j and k are each independently 0, 1, 2 or 3.

[0068] Equation 11 is:

[0069] [Equation 11]

[0070]

[0071] In Equation 11,

[0072] R 61 and R 62 Each is independently unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, of which R 61 and R 62 At least one of them is a polycyclic aryl or polycyclic heteroaryl, optionally, an unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0073] R 63 To R 66 Each is independently unsubstituted or substituted C1-C 20 Alkyl, or unsubstituted or substituted C6-C 30 Aryl, wherein when r is 2, 3 or 4, each R 63 Whether they are the same or different, when s is 2, 3 or 4, each R 64 Whether they are the same or different, when t is 2, 3 or 4, each R 65 Whether they are the same or different, when u is 2, 3 or 4, each R 66 They are the same or different from each other;

[0074] L1 to L3 are each independently a single bond, unsubstituted or substituted C6-C. 30 Aryl styrene, or unsubstituted or substituted C3-C 30Hybrid aromatic styrene, optionally, unsubstituted or substituted C6-C 30 Aryl styrene and unsubstituted or substituted C3-C 30 Each heteroarylene independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0075] r, s, and t are each independently 0, 1, 2, 3, or 4; and

[0076] u can be 0, 1, 2, or 3.

[0077] Equation 13 is:

[0078] [Equation 13]

[0079]

[0080] In Equation 13,

[0081] R 71 To R 73 Each is independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spirostructure, in which R 71 To R 73 One of them has a structure represented by Equation 14:

[0082] [Formula 14]

[0083]

[0084] In Equation 14,

[0085] L4 is a single bond, unsubstituted or substituted C6-C. 30 Aryl styrene, or unsubstituted or substituted C3-C 30 Hybrid aromatic styrene, optionally, unsubstituted or substituted C6-C 30 Aryl styrene and unsubstituted or substituted C3-C 30 Each heteroarylene independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0086] When w is 0, Ar1 is unsubstituted or substituted C6-C. 30 aryl, or when w is 1, Ar1 is unsubstituted or substituted C6-C. 30 Aryl alkyl group, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C6-C 30 Aryl groups react independently with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0087] Ar2 is unsubstituted or substituted C6-C 30 Aryl;

[0088] R 74 It is hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl; and

[0089] w is 0 or 1.

[0090] The light-emitting layer may include a single light-emitting part or multiple light-emitting parts to form a series structure.

[0091] In another aspect, this disclosure provides an organic light-emitting diode (OLED) comprising: a first electrode; a second electrode facing the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode, wherein the light-emitting layer comprises: a first light-emitting portion disposed between the first electrode and the second electrode and including a blue light-emitting material layer; a second light-emitting portion disposed between the first light-emitting portion and the second electrode; and a first charge-generating layer disposed between the first light-emitting portion and the second light-emitting portion, wherein the second light-emitting portion comprises: at least one light-emitting material layer, a hole transport layer disposed between the first charge-generating layer and the at least one light-emitting material layer, and an electron transport layer disposed between the at least one light-emitting material layer and the second electrode, wherein the at least one light-emitting material layer comprises a host and a dopant, the host comprising: a first host represented by a structure of Formula 7, and a second host represented by a structure of Formula 9, the dopant comprising an organometallic compound represented by a structure of Formula 1, wherein the hole transport layer comprises an organic compound represented by a structure of Formula 11, and wherein the electron transport layer comprises an organic compound represented by a structure of Formula 13.

[0092] In another aspect, this disclosure provides an organic light-emitting device, such as an organic light-emitting display device or an organic light-emitting illumination device, which includes a substrate and the organic light-emitting diode located above the substrate.

[0093] Organometallic compounds used as dopants include metal atoms connected by covalent or coordinate bonds to fused heteroaromatic ligands and pyridine ligands comprising at least five rings. The organometallic compound can be a heterometallic complex comprising two different bidentate ligands coordinated to the metal atom; by combining two different bidentate ligands, the photoluminescence purity and emission color of the metal compound can be easily controlled.

[0094] Each of the biscarbazole-based compound and / or the azine-based material having a fused heteroaryl moiety can be used as a first host and a second host in the EML, respectively. When the biscarbazole-based compound with beneficial hole transport properties and / or the azine-based material with beneficial electron transport properties are used with the organometallic compound, charge and exciton energy can be rapidly transferred from the biscarbazole-based material and the azine-based material to the organometallic compound. Furthermore, each of the hole transport layer comprising a spirodifluorene-based material with beneficial hole transport properties and the electron transport layer comprising a benzimidazole-based material is disposed adjacent to the luminescent material layer.

[0095] When the light-emitting layer includes an organometallic compound as a dopant and a biscarbazol-based material and / or azazine-based material as the host, a spirodifluorene-based material as a hole transport material, and / or a benzimidazole-based material as an electron transport material, organic light-emitting diodes and organic light-emitting devices can reduce their driving voltage and improve their luminous efficiency and luminous lifetime.

[0096] It should be understood that the foregoing general description and the following detailed description are exemplary and explanatory, and are intended to provide further explanation of the claimed inventive concept. Attached Figure Description

[0097] The accompanying drawings, which are included to provide a further understanding of the present disclosure and are incorporated in and constitute a part of this application, illustrate embodiments of the present disclosure and, together with the description, serve to explain the principles of the present disclosure.

[0098] Figure 1 A schematic circuit diagram of an organic light-emitting display device according to the present disclosure is shown.

[0099] Figure 2 A cross-sectional view of an organic light-emitting display device is shown as an example of an organic light-emitting device according to an exemplary embodiment of the present disclosure.

[0100] Figure 3A cross-sectional view of an organic light-emitting diode having a single light-emitting portion according to an exemplary embodiment of the present disclosure is shown.

[0101] Figure 4 A cross-sectional view of an organic light-emitting display device according to another exemplary embodiment of the present disclosure is shown.

[0102] Figure 5 A cross-sectional view of an organic light-emitting diode having a double-stacked structure according to another exemplary embodiment of the present disclosure is shown.

[0103] Figure 6 A cross-sectional view of an organic light-emitting diode having a triple-stacked structure according to yet another exemplary embodiment of the present disclosure is shown. Detailed Implementation

[0104] Reference will now be made in detail to various aspects of this disclosure, examples of which are shown in the accompanying drawings. Where possible, the same reference numerals will be used throughout the drawings to refer to the same or similar parts.

[0105] The advantages and features of this disclosure, and its implementation methods, will be illustrated by the following exemplary embodiments described in conjunction with the accompanying drawings. However, this disclosure may be embodied in different forms and should not be construed as limited to the exemplary embodiments set forth herein. Rather, these exemplary embodiments are provided to make this disclosure sufficiently thorough and complete to assist those skilled in the art in fully understanding its scope. Furthermore, the scope of protection of this disclosure is defined by the claims and their equivalents.

[0106] The shapes, dimensions, ratios, angles, quantities, etc., shown in the accompanying drawings to describe various exemplary embodiments of this disclosure are given by way of example only. Therefore, this disclosure is not limited to the description in the drawings. Unless otherwise stated, the same or similar elements are indicated by the same reference numerals throughout the specification.

[0107] In the following description, detailed descriptions of such known configurations may be omitted where such detailed descriptions might unnecessarily obscure the essential points of this disclosure.

[0108] In this specification, one or more additional elements may be added where terms such as “comprising,” “having,” “including”, etc., are used, unless a term such as “only” is used. Elements described in the singular are intended to include multiple elements, and vice versa, unless the context clearly indicates otherwise.

[0109] When interpreting an element, it will be interpreted as including a range of error or tolerance, even if no explicit description of such range of error or tolerance is provided.

[0110] In the description of various embodiments of this disclosure, when describing positional relationships, for example, when using terms such as "on," "above," "below," "above," "below," "near," or "adjacent" to describe the positional relationship between two parts, one or more other parts may be located between the two parts, unless more restrictive terms such as "immediately," "directly," or "immediately adjacent" are used. For example, when one element or layer is disposed "on" another element or layer, a third layer or element may be inserted between them.

[0111] When describing temporal relationships, discontinuous situations may be included when the temporal order is described as such as "after", "following", "next", or "before", unless more restrictive terms such as "exactly", "immediately", or "directly" are used.

[0112] Although the terms “first,” “second,” etc., may be used herein to describe various elements, these elements should not be limited by these terms. These terms are used only to distinguish one element from another. For example, without departing from the scope of this disclosure, a first element may be referred to as a second element, and similarly, a second element may be referred to as a first element.

[0113] Although the terms “first,” “second,” A, B, (a), (b), etc., may be used in this document to describe various elements, these elements should not be construed as being limited by these terms, as they are not used to define a particular order, priority, or number of the corresponding elements. These terms are only used to distinguish one element from another.

[0114] To describe an element or layer as “connected” to another element or layer means that the element or layer can be directly connected to another element or layer, or indirectly connected to or adhered to another element or layer, wherein one or more intermediate elements or layers are “set” or “inserted” between the elements or layers, unless otherwise stated.

[0115] The term “at least one” should be understood to include any and all combinations of one or more of the related listed items. For example, “at least one of the first element, the second element, and the third element” means a combination of all three listed elements, a combination of any two of the three elements, and each individual element, the first element, the second element, and the third element.

[0116] Features of the various embodiments of this disclosure may be coupled or combined with each other in part or in whole, and may interoperate with each other in various ways and be driven in a technical manner as can be fully understood by those skilled in the art. Embodiments of this disclosure may be implemented independently of each other or may be implemented together in an interdependent relationship.

[0117] In the following, exemplary embodiments of the present disclosure will be described in detail with reference to the accompanying drawings. When adding reference numerals to the elements in each drawing, similar reference numerals may refer to similar elements even if the same elements are shown in other drawings. Furthermore, for ease of description, the scale of each element illustrated in the drawings may differ from the actual scale. Therefore, the illustrated elements are not limited to the specific scale shown in the drawings.

[0118] This disclosure relates to an organic light-emitting diode (OLED), wherein at least one light-emitting material layer comprises an organometallic compound having beneficial optical properties and an organic compound having beneficial charge transport properties, and to an organic light-emitting device including the diode, such that the diode and the device can reduce their driving voltage and maximize their luminous efficiency and luminous lifetime. The diode can be used in organic light-emitting devices, such as organic light-emitting display devices or organic light-emitting lighting devices.

[0119] Figure 1 A schematic circuit diagram of an organic light-emitting display device according to this disclosure is shown. Figure 1 As shown, in the organic light-emitting display device 100, the gate line GL, data line DL, and power line PL each intersect each other to define a pixel region P. A switching thin-film transistor Ts, a driving thin-film transistor Td, a storage capacitor Cst, and an organic light-emitting diode D are disposed within the pixel region P. The pixel region P may include a red (R) pixel region, a green (G) pixel region, and a blue (B) pixel region. However, embodiments of this disclosure are not limited to these examples.

[0120] A switching thin-film transistor (TFT) Ts is connected to the gate line GL and the data line DL. A driving thin-film transistor (TFT) Td and a storage capacitor Cst are connected between the switching TFT Ts and the power line PL. An organic light-emitting diode (OLED) D is connected to the driving TFT Td. When the switching TFT Ts is turned on by a gate signal applied to the gate line GL, the data signal applied to the data line DL is applied to the gate of the driving TFT Td and one electrode of the storage capacitor Cst through the switching TFT Ts.

[0121] The driving thin-film transistor Td is achieved by applying it to the gate 130 ( Figure 2) It is turned on by the data signal, so that a current proportional to the data signal is supplied from the power supply line PL to the organic light-emitting diode D through the driving thin film transistor Td. Then, the organic light-emitting diode D emits light with a brightness proportional to the current flowing through the driving thin film transistor Td. In this case, the storage capacitor Cst is charged with a voltage proportional to the data signal, so that the voltage of the gate in the driving thin film transistor Td remains constant during one frame. Therefore, the organic light-emitting display device can display a desired image.

[0122] Figure 2 FIG. shows a schematic cross-sectional view of an organic light-emitting display device according to an exemplary embodiment of the present disclosure. As Figure 2 shown, the organic light-emitting display device 100 includes a substrate 102, a thin film transistor Tr located on the substrate 102, and an organic light-emitting diode D connected to the thin film transistor Tr. As an example, the substrate 102 may include a red pixel region, a green pixel region, and a blue pixel region, and an organic light-emitting diode D in each pixel region. Each organic light-emitting diode D emits red light, green light, or blue light respectively, and is accordingly located in the red pixel region, the green pixel region, and the blue pixel region.

[0123] The substrate 102 may include, but is not limited to, glass, a thin flexible material, and / or polymer plastic. For example, the flexible material may be selected from, but is not limited to, polyimide (PI), polyethersulfone (PES), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), polycarbonate (PC), and / or a combination thereof. The substrate 102 on which the thin film transistor Tr and the organic light-emitting diode D are arranged forms an array substrate.

[0124] A buffer layer 106 may be provided on the substrate 102. The thin film transistor Tr may be provided on the buffer layer 106. The buffer layer 106 may be omitted. A semiconductor layer 110 is provided on the buffer layer 106. In one exemplary embodiment, the semiconductor layer 110 may include, but is not limited to, an oxide semiconductor material. In this case, a light-shielding pattern may be provided below the semiconductor layer 110, which can prevent light from incident on the semiconductor layer 110, and thereby prevent or reduce the deterioration of the semiconductor layer 110 by light. Alternatively, the semiconductor layer 110 may include polysilicon. In this case, the relative edges of the semiconductor layer 110 may be doped with impurities.

[0125] A gate insulating layer 120 including an insulating material is provided on the semiconductor layer 110. The gate insulating layer 120 may include, but is not limited to, inorganic insulating materials such as silicon oxide (SiO x , where 0 < x ≤ 2) or silicon nitride (SiN x , where 0 < x ≤ 2).

[0126] A gate 130, made of a conductive material such as a metal, is disposed on a gate insulating layer 120 so as to correspond to the center of the semiconductor layer 110. When the gate insulating layer 120 is disposed as... Figure 2 When the entire area of ​​the substrate 102 shown is covered, the gate insulating layer 120 can be patterned in the same way as the gate 130.

[0127] An interlayer insulating layer 140, comprising an insulating material, is disposed on the gate 130 and covers the entire surface of the substrate 102. The interlayer insulating layer 140 may include, but is not limited to, silicon oxide (SiO2). x ) or silicon nitride (SiN) x Inorganic insulating materials such as benzocyclobutene or photo-acryl.

[0128] The interlayer insulating layer 140 has a first semiconductor layer contact hole 142 and a second semiconductor layer contact hole 144, which expose or not cover a portion of the surface closer to the opposite end than the center of the semiconductor layer 110. The first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144 are disposed on opposite sides of the gate 130 and spaced apart from the gate 130. The first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144 are formed on... Figure 2 The gate insulating layer 120 is formed within the gate insulating layer 140. Alternatively, when the gate insulating layer 120 is patterned in the same way as the gate 130, the first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144 may be formed only within the interlayer insulating layer 140.

[0129] Source 152 and drain 154, made of a conductive material such as metal, are disposed on interlayer insulating layer 140. Source 152 and drain 154 are spaced apart from each other on opposite sides of gate 130 and contact both sides of semiconductor layer 110 through first semiconductor layer contact hole 142 and second semiconductor layer contact hole 144, respectively.

[0130] Semiconductor layer 110, gate 130, source 152 and drain 154 constitute a thin-film transistor Tr that acts as a driving element. Figure 2 The thin-film transistor Tr has a coplanar structure in which the gate 130, source 152, and drain 154 are disposed on the semiconductor layer 110. Alternatively, the thin-film transistor Tr may have an inverted staggered structure in which the gate is disposed below the semiconductor layer and the source and drain are disposed on the semiconductor layer. In this case, the semiconductor layer may include amorphous silicon.

[0131] Gate lines GL and data lines DL, which intersect to define a pixel region P, and switching elements Ts connected to the gate lines GL and data lines DL, may be further formed in the pixel region P. The switching elements Ts are connected to a thin-film transistor Tr, which serves as a driving element. Furthermore, a power line PL is parallel and spaced apart from either the gate line GL or the data line DL. The thin-film transistor Tr may further include a storage capacitor Cst configured to maintain a constant voltage at the gate 130 within a frame.

[0132] A passivation layer 160 is disposed on the source 152 and the drain 154. The passivation layer 160 covers the entire thin-film transistor Tr on the substrate 102. The passivation layer 160 has a flat top surface and a drain contact hole 162 that may or may not cover the drain 154 of the thin-film transistor Tr. When the drain contact hole 162 is disposed on the second semiconductor layer contact hole 144, it may be spaced apart from the second semiconductor layer contact hole 144.

[0133] The organic light-emitting diode (OLED) D includes a first electrode 210 disposed on a passivation layer 160 and connected to a drain 154 of a thin-film transistor Tr. The OLED D further includes a light-emitting layer 230 and a second electrode 220 disposed sequentially on the first electrode 210.

[0134] A first electrode 210 is disposed in each pixel region. The first electrode 210 may be an anode and comprises a conductive material having a relatively high work function value. For example, the first electrode 210 may include, but is not limited to, transparent conductive oxide (TCO). More specifically, the first electrode 210 may comprise indium tin oxide (ITO), indium zinc oxide (IZO), indium tin zinc oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium cerium oxide (ICO), aluminum-doped zinc oxide (AZO), and / or the like.

[0135] In one exemplary embodiment, when the organic light-emitting display device 100 is bottom-emitting, the first electrode 210 may have a single-layer structure of TCO. Alternatively, when the organic light-emitting display device 100 is top-emitting, a reflective electrode or reflective layer may be disposed below the first electrode 210. For example, the reflective electrode or reflective layer may include, but is not limited to, a silver (Ag) or aluminum-palladium-copper (APC) alloy. In a top-emitting OLED D, the first electrode 210 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0136] In addition, a dam layer 164 is disposed on the passivation layer 160 to cover the edge of the first electrode 210. The dam layer 164 may or may not cover the center of the first electrode 210 corresponding to each pixel region. The dam layer 164 may be omitted.

[0137] The light-emitting layer 230 is disposed on the first electrode 210. In one exemplary embodiment, the light-emitting layer 230 may have a single-layer structure of a light-emitting material layer (EML). Alternatively, the light-emitting layer 230 may have a multilayer structure of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an EML, a hole blocking layer (HBL), an electron transport layer (ETL), and / or an electron injection layer (EIL) (see [link to documentation]). Figure 3 , Figure 5 ,and Figure 6 In one aspect, the light-emitting layer 230 may have a single light-emitting portion. Alternatively, the light-emitting layer 230 may have multiple light-emitting portions to form a series structure.

[0138] The light-emitting layer 230 may include at least one host and dopant, enabling OLEDs and organic light-emitting display devices to reduce their driving voltage and improve their luminous efficiency and luminous lifetime.

[0139] The second electrode 220 is disposed on the substrate 102 on which the light-emitting layer 230 is disposed. The second electrode 220 may be disposed over the entire display area. The second electrode 220 may include a conductive material having a relatively low work function value compared to the first electrode 210. The second electrode 220 may be a cathode. For example, the second electrode 220 may include at least one of the following, but not limited to, aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), alloys of the like such as aluminum-magnesium alloys (Al-Mg), and combinations thereof. When the organic light-emitting display device 100 is a top-emitting type, the second electrode 220 is thinner to have light-transmitting (semi-transmitting) properties.

[0140] Furthermore, an encapsulation film 170 may be disposed on the second electrode 220 to prevent or reduce the penetration of external moisture into the organic light-emitting diode D. The encapsulation film 170 may have, but is not limited to, a laminated structure of a first inorganic insulating film 172, an organic insulating film 174, and a second inorganic insulating film 176. The encapsulation film 170 may be omitted.

[0141] A polarizing plate can be attached to the encapsulation film to reduce the reflection of external light. For example, the polarizing plate can be a circular polarizing plate. When the organic light-emitting display device 100 is a bottom-emitting type, the polarizer can be disposed below the substrate 102. Alternatively, when the organic light-emitting display device 100 is a top-emitting type, the polarizer can be disposed on the encapsulation film 170. In addition, a cover window can be attached to the encapsulation film 170 or the polarizer. In this case, the substrate 102 and the cover window can be flexible, so the organic light-emitting display device 100 can be a flexible display device.

[0142] Next, we will describe OLED D in more detail. Figure 3A schematic cross-sectional view of an organic light-emitting diode having a single light-emitting portion, according to an exemplary embodiment of the present disclosure, is shown. Figure 3 As shown, the organic light-emitting diode (OLED) D1 according to this disclosure includes a first electrode 210 and a second electrode 220 facing each other, and a light-emitting layer 230 disposed between the first electrode 210 and the second electrode 220. The organic light-emitting display device 100 includes a red pixel region, a green pixel region, and a blue pixel region, and the OLED D1 can be disposed in the green pixel region.

[0143] In one exemplary embodiment, the light-emitting layer 230 includes a light-emitting material layer (EML) 340 disposed between the first electrode 210 and the second electrode 220. Furthermore, the light-emitting layer 230 may include at least one of an HTL 320 disposed between the first electrode 210 and the EML 340 and an ETL 360 disposed between the second electrode 220 and the EML 340. Additionally, the light-emitting layer 230 may further include at least one of a HIL 310 disposed between the first electrode 210 and the HTL 320 and an EIL 370 disposed between the second electrode 220 and the ETL 360. Alternatively, the light-emitting layer 230 may further include a first exciton blocking layer, i.e., an EBL 330 disposed between the HTL 320 and the EML 340, and / or a second exciton blocking layer, i.e., an HBL 350 disposed between the EML 340 and the ETL 360.

[0144] The first electrode 210 may be an anode that provides holes to the EML 340. The first electrode 210 may include a conductive material having a relatively high work function value, such as a transparent conductive oxide (TCO). In one exemplary embodiment, the first electrode 210 may include, but is not limited to, ITO, IZO, ITZO, SnO, ZnO, ICO, AZO, and the like.

[0145] The second electrode 220 may be a cathode that provides electrons to the EML 340. The second electrode 220 may include a conductive material with a relatively low work function value, i.e., a highly reflective material such as Al, Mg, Ca, Ag, and / or alloys thereof, and / or combinations thereof (such as Al-Mg).

[0146] EML 340 includes a dopant 342 and a first body 344, and an optional second body 346, at which a large amount of light emission can be generated. The dopant 342 can be an organometallic compound that emits green light and can have a structure represented by Formula 1:

[0147] [Formula 1]

[0148] Ir(L A )m (L B ) n

[0149] Where L A It has the following structure, represented by Equation 2; L B It is an auxiliary ligand with the structure represented by Equation 3; m is 1, 2 or 3 and n is 0, 1 or 2, where m+n is 3;

[0150] [Equation 2]

[0151]

[0152] In Equation 2,

[0153] X1 and X2 are each independently CR7 or N;

[0154] X3 to X5 are each independently CR8 or N, and at least one of X3 to X5 is CR8;

[0155] X6 to X9 are each independently CR9 or N, and at least one of X6 to X9 is CR9;

[0156] When two adjacent groups among R1 to R5, and / or

[0157] When b is an integer of 2 or greater, two adjacent R6, and / or

[0158] X3 and X4 or X4 and X5, and / or

[0159] X6 and X7, X7 and X8, or X8 and X9

[0160] When no loop is formed,

[0161] R1 to R9 are each independently hydrogen, protium, deuterium, undeuterated or deuterated unsubstituted or substituted C1-C. 20 Alkyl, undeuterated or deuterated, unsubstituted or substituted C1-C 20 Heteroalkyl, undeuterated or deuterated, unsubstituted or substituted C2-C 20 Alkenyl, undeuterated or deuterated, unsubstituted or substituted C2-C 20 Heterene, undeuterated or deuterated, unsubstituted or substituted C1-C 20 Alkoxy, carboxyl, nitrile, isonitrile, sulfonamide, phosphine, undeuterated or deuterated unsubstituted or substituted C1-C 20 Alkylamino, undeuterated or deuterated, unsubstituted or substituted C1-C 20 Alkyl silyl, undeuterated or deuterated, unsubstituted or substituted C4-C 30 Alicyclic group, undeuterated or deuterated, unsubstituted or substituted C3-C 30Heterocyclic group, undeuterated or deuterated unsubstituted or substituted C6-C 30 Aryl, or undeuterated or deuterated unsubstituted or substituted C3-C 30 Heteroaryl, wherein when b is 2, 3 or 4, each R6 is the same or different from each other;

[0162] Optionally,

[0163] Two adjacent groups from R1 to R5, and / or

[0164] When b is 2, 3, or 4, two adjacent R6, and / or

[0165] X3 and X4 or X4 and X5, and / or

[0166] X6 and X7, X7 and X8, or X8 and X9

[0167] Further, directly or indirectly, they are linked together to form unsubstituted or substituted C4-C. 20 Alicyclic, unsubstituted or substituted C3-C 20 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Mixed fragrance ring;

[0168] a is 0, 1, or 2; and

[0169] b is 0, 1, 2, 3, or 4.

[0170] Equation 3 is:

[0171] [Formula 3]

[0172]

[0173] As used herein, the term "unsubstituted" refers to hydrogen directly bonded to a carbon atom. As used herein, "hydrogen" may refer to protium.

[0174] As used herein, “substitution” means that hydrogen is substituted by a substituent. Substituents include, but are not limited to, deuterium, unsubstituted, or deuterium- or halogen-substituted C1-C groups. 20 Alkyl, unsubstituted, or deuterated or halogenated C1-C 20 Alkoxy, halogen, cyano, -CF3, hydroxy, carboxyl, carbonyl, amino, C1-C 10 Alkylamino, C6-C 30 arylamino, C3-C 30 heteroarylamino, C6-C 30 Aryl, C3-C 30 heteroaryl, nitro, hydrazine, sulfonate, C1-C 20 Alkyl silyl, C6-C30 Arylsilyl and C3-C 30 Heteroarylsilyl group.

[0175] As used herein, the term "alkyl" refers to a branched or unbranched saturated hydrocarbon group having 1 to 20 carbon atoms, such as methyl or ethyl, or having 1 to 24 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, etc.

[0176] As used herein, the term "alkenyl" is a hydrocarbon group containing 2 to 20 carbon atoms and at least one carbon-carbon double bond. Alkenyl groups can be substituted with one or more substituents.

[0177] As used herein, the term "alicyclic" or "cycloalkyl" refers to a non-aromatic carbonyl ring consisting of at least three carbon atoms. Examples of alicyclic groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, etc. Alicyclic groups can be substituted with one or more substituents.

[0178] As used herein, the term "alkoxy" refers to a branched or unbranched alkyl group bonded by an ether bond represented by the formula -O (-alkyl), where "alkyl" is as defined herein. Examples of alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, and tert-butoxy.

[0179] As used herein, the term "alkylamino" refers to a group represented by the formula -NH(-alkyl) or -N(-alkyl)2, wherein the alkyl group is as defined herein. Examples of alkylamino groups represented by the formula -NH(-alkyl) include, but are not limited to, methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, (sec-butyl)amino, (tert-butyl)amino, pentamino, isopentamino, (tert-pentyl)amino, hexylamino, etc. Examples of alkylamino groups represented by the formula -N(-alkyl)2 include, but are not limited to, dimethylamino, diethylamino, dipropylamino, diisopropylamino, dibutylamino, diisobutylamino, di(sec-butyl)amino, di(tert-butyl)amino, dipentamino, diisopentamino, di(tert-pentyl)amino, dihexylamino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-ethyl-N-propylamino, etc.

[0180] As used herein, the terms "aromatic hydrocarbon" or "aryl" are well known in the art. This term includes monocyclic, monocyclic, or fused-ring polycyclic groups covalently linked to each other by bonds. The aromatic hydrocarbon group can be unsubstituted or substituted. Examples of aromatic hydrocarbons or aryl groups include phenyl, 1-naphthyl, 2-naphthyl, 4-biphenyl, anthraceneyl, and phenanthrene, etc. Substituents in aromatic hydrocarbons or aryl groups are as defined herein.

[0181] As used herein, the term "alkylsilyl" refers to any straight-chain or branched, saturated or unsaturated acyclic alkyl group having 1 to 20 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.

[0182] As used in this article, the term "halogen" refers to a fluorine, chlorine, bromine, or iodine atom.

[0183] As used herein, the term "hetero" in terms such as "heteroalkyl", "heteroalkenyl", "heteroalicycloyl", "heteroaryl", "heterocycloalkylene", "heteroarylalkylene", "heteroaryl-o-xylylene", "heterocycloalkyl", "heteroaryl", "heteroarylalkyl", "heteroaryloxy", "heteroarylamino" means that at least one carbon atom, for example, one to five carbon atoms constituting an aliphatic chain, alicyclic group or ring, or an aromatic group or ring, is replaced by at least one heteroatom selected from the group consisting of N, O, S, and P.

[0184] As used herein, the term "heteroaromatic" or "heteroaryl" refers to a heterocycle comprising at least one heteroatom selected from N, O, and S, wherein the ring system is an aromatic ring. The term includes monocyclic or fused-ring polycyclic groups covalently linked to each other by bonds. Heteroaromatic groups can be unsubstituted or substituted. Examples of heteroaromatic or heteroaryl groups include pyridyl, pyrroleyl, pyrazinyl, pyrimidinyl, thiopheneyl (or phenylthio), thiazolyl, furanyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, oxadiazolyl, and thiadiazolyl.

[0185] As used herein, the term “heteroaryloxy” refers to a group represented by the formula -O-(heteroaryl), wherein the heteroaryl group is as defined herein.

[0186] In one exemplary implementation, when R1 to R9 in Equation 2 are each independently C6-C 30 In the aryl form, R1 to R9 can each be, but are not limited to, C6-C. 30 Aryl, C7-C 30 arylalkyl, C6-C 30 aryloxy groups and C6-C 30 Aromatic amino groups. As an example, when R1 to R9 are each independently C6-C... 30In the case of aryl groups, R1 to R9 can each be independently, but not limited to, unfused or fused aryl groups, such as phenyl, biphenyl, terphenyl, naphthyl, anthracene, pentalenyl, indenyl, indeno-indenyl, heptalenyl, biphenylenyl, indacenyl, phenalenyl, phenanthrenyl, benzo-phenanthrenyl, dibenzo-phenanthrenyl, azulenyl, pyrenyl, fluoranthenyl, and triphenylenyl. The aryl group can be chrysenyl, tetraphenylenyl, tetracenyl, pleiadenyl, picenyl, pentaphenylenyl, pentaphenylenyl, fluorenyl, indeno-fluorenyl, or spirofluorenyl. The unfused or fused aryl group can be substituted or unsubstituted. In some embodiments, two adjacent groups from R1 to R5 or two adjacent groups from R7 to R9 form an unfused or fused aryl group that can be substituted or unsubstituted.

[0187] Alternatively, when R1 to R9 in equation 2 are each independently C3-C 30 In heteroaryl cases, R1 to R9 can each be, but is not limited to, C3-C. 30 heteroaryl, C4-C 30 Heteroarylalkyl, C3-C 30 Heteroaryl groups and C3-C 30 Heteroarylamino. As an example, when R1 to R9 can each independently be C3-C. 30In the case of heteroaryl groups, R1 to R9 can each independently include, but are not limited to, unfused or fused heteroaryl groups, such as pyrroloyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetraazinyl, imidazolyl, pyrazolyl, indoleyl, isoindoleyl, indazoleyl, indeneyl, pyrroloazinyl, carbazoleyl, benzo[carbazoleyl], dibenzo[carbazoleyl], indole[carbazoleyl], indene[carbazoleyl], benzofuran-carbazoleyl, benzothiophene-carbazoleyl, carbolinyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalyl, cinnamyl, quinazolinyl, quinolinyl, purineyl, benzoquinolinyl, benzo[isoquinolinyl], benzo[quinoxalyl], benzo[quinoxalyl], benzo[quinoxalyl], benzo[quinoxalyl] Acridine, phenazinyl, phenoxazinyl, phenthiazinyl, phenanthrolinel, piperidinyl, phenanthinyl, pteridinyl, naphridinyl, furanyl, pyranyl, oxazinyl, oxazolyl, oxadiazolyl, triazolyl, dioxalyl, benzofuranyl, dibenzofuranyl, thiophene, xanthyl, chromenyl, isochromenyl, thiazinyl, thiophene, benzo-thiophene, dibenzothiophene, difuranylpyrazinyl, benzofuranyl-dibenzofuranyl, benzothiophene-benzothiophene, benzothiophene-dibenzothiophene, benzothiophene-benzofuranyl, xanthyl-linked spiroacridinyl, at least one C1-C 10 Alkyl-substituted dihydroacrylinyl and N-substituted spirofluorenyl. Unfused or fused aryl groups can be substituted or unsubstituted.

[0188] As an example, each of the aryl or heteroaryl groups R1 to R9 can consist of one to three aromatic or heteroaryl rings. When the number of aromatic or heteroaryl rings R1 to R9 becomes more than four, the conjugated structure throughout the molecule becomes too long, and therefore, the organometallic compound may have an excessively narrow band gap. For example, each of the aryl or heteroaryl groups R1 to R9 can independently include, but is not limited to, phenyl, biphenyl, naphthyl, anthracene, pyrrole, triazinyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, furanyl, benzofuranyl, dibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, carbazolyl, acridinel, carbaolinyl, phenazinyl, phenoxazinyl, or phenothiazinyl.

[0189] In one exemplary embodiment, the alkyl, heteroalkyl, alkenyl, heteroalkenyl, alkoxy, alkylamino, alkylsilyl, alicyclic, heteroalicyclic, aryl, and heteroaryl groups of R1 to R9 may each be independently unsubstituted or halogenated, C1-C 10 Alkyl, C4-C 20 Alicyclic group, C3-C 20 heterocyclic group, C6-C 20 Aryl and C3-C 20 At least one of the heteroaryl groups is substituted. In some embodiments, a C4-C group is formed by two adjacent groups from R1 to R6, two adjacent R8 groups, or two adjacent R9 groups.20 Alicyclic, C3-C 20 Aliphatic ring, C6-C 30 Aromatic rings and C3-C 30 Each of the heterocyclic aromatic rings can be independently unsubstituted or substituted by at least one C1-C. 10 Alkyl substitution.

[0190] Alternatively, two adjacent groups from R1 to R6, two adjacent R8 groups, and two adjacent R9 groups can form an unsubstituted or substituted C4-C group. 30 Alicyclic (e.g., C5-C) 10 Alicyclic, unsubstituted or substituted C3-C 30 heterocyclic rings (e.g., C3-C) 10 heterocyclic rings), unsubstituted or substituted C6-C 30 Aromatic rings (e.g., C6-C) 20 Aromatic rings, or unsubstituted or substituted C3-C 30 heterocyclic aromatic rings (e.g., C3-C) 20 (Heteroaromatic rings). Alicyclic, heterocyclic, aromatic, and heteroaromatic rings formed by two adjacent groups from R1 to R6, two adjacent R8s, and two adjacent R9s are not limited to specific rings. For example, aromatic or heteroaromatic rings formed by these groups may include, but are not limited to, those that are unsubstituted or substituted by at least one C1-C2 group. 10 Alkyl-substituted benzene rings, pyridine rings, indole rings, pyran rings, or fluorene rings. In some embodiments, an aromatic ring or heteroaromatic ring formed by two adjacent groups from R1 to R6, two adjacent R8s, or two adjacent R9s can form an unsubstituted or substituted fused aromatic ring or heteroaromatic ring. The definitions of fused aromatic rings and fused heteroaromatic rings are the same as described above.

[0191] Organometallic compounds having the structure represented by Formula 1 have a heteroaryl ligand consisting of at least five rings. Because these organometallic compounds can have a rigid chemical conformation, their conformation does not rotate during luminescence. Therefore, a good luminescence lifetime can be maintained. Organometallic compounds can have a specific photoluminescence emission range, thus improving their color purity.

[0192] In one exemplary embodiment, each of m and n in Formula 1 can be 1 or 2. When the organometallic compound can be a heterometallic complex comprising two different bidentate ligands coordinated to the central metal atom, the photoluminescence purity and emission color of the organometallic compound can be easily controlled by combining the two different bidentate ligands. Furthermore, the color purity and emission peak of the organometallic compound can be controlled by introducing various substituents into each ligand. Alternatively, in Formula 1, m can be 3 and n can be 0. As an example, an organometallic compound having the structure represented by Formula 1 can emit green light and can improve the luminous efficiency of an organic light-emitting diode.

[0193] As an example, in Equation 2, X1 is CR7, X2 is CR7 or N, X3 to X5 are each independently CR8, and X6 to X9 are each independently CR9. That is, each of X1 and X3 to X9 can be an unsubstituted or substituted carbon atom independently.

[0194] In one exemplary embodiment, when a is 1 or 2, the phenyl group in Formula 2 may be substituted to the meta position of the pyridine ring coordinated with the metal atom, and each of X1 and X3 to X9 in Formula 2 may independently be an unsubstituted or substituted carbon atom. Such an L A It may have the following structure, represented by Equation 4A or Equation 4B:

[0195] [Formula 4A]

[0196]

[0197] [Formula 4B]

[0198]

[0199] Among them, in Equations 4A and 4B,

[0200] Each of R1 to R6 and b is as defined in Equation 2;

[0201] When d is an integer of 2 or greater, two adjacent R 13 and / or

[0202] When e is an integer of 2 or greater, two adjacent R 14 ,

[0203] When no loop is formed,

[0204] R 11 To R 14 Each is independently hydrogen, protium, deuterium, undeuterated or deuterated unsubstituted or substituted C1-C 20 Alkyl, undeuterated or deuterated, unsubstituted or substituted C1-C 20 Heteroalkyl, undeuterated or deuterated, unsubstituted or substituted C2-C 20 Alkenyl, undeuterated or deuterated, unsubstituted or substituted C2-C 20 Heterene, undeuterated or deuterated, unsubstituted or substituted C1-C 20 Alkoxy, carboxyl, nitrile, isonitrile, sulfonamide, phosphine, undeuterated or deuterated unsubstituted or substituted C1-C 20 Alkylamino, undeuterated or deuterated, unsubstituted or substituted C1-C 20 Alkyl silyl, undeuterated or deuterated, unsubstituted or substituted C4-C 30Alicyclic group, undeuterated or deuterated, unsubstituted or substituted C3-C 30 Heterocyclic group, undeuterated or deuterated unsubstituted or substituted C6-C 30 Aryl, or undeuterated or deuterated unsubstituted or substituted C3-C 30 Mixed aromatics;

[0205] Optionally,

[0206] When d is 2 or 3 and e is 2, 3 or 4

[0207] When d is 2 or 3, two adjacent R 13 and / or

[0208] When e is 2, 3, or 4, two adjacent R 14

[0209] Further, directly or indirectly, they are linked together to form unsubstituted or substituted C4-C. 20 Alicyclic, unsubstituted or substituted C3-C 20 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Mixed fragrance ring;

[0210] c is 0 or 1;

[0211] d is 0, 1, 2, or 3; and

[0212] e can be 0, 1, 2, 3, or 4.

[0213] In another exemplary embodiment, when a is 1 or 2, the phenyl group in Formula 2 may be linked to the para position of the pyridine ring coordinated to the metal atom, and each of X1 and X3 through X9 in Formula 2 may be an unsubstituted or substituted carbon atom independently. Such an L A It can have the following structures represented by Equation 4C or Equation 4D:

[0214] [Formula 4C]

[0215]

[0216] [Form 4D]

[0217]

[0218] In Equations 4C and 4D,

[0219] Each of R1 to R6 and b is as defined in Equation 2;

[0220] When d is an integer of 2 or greater, two adjacent R 13 and / or

[0221] When e is an integer of 2 or greater, two adjacent R 14 ,

[0222] When no loop is formed,

[0223] R 11 To R 14 Each is independently hydrogen, protium, deuterium, undeuterated or deuterated unsubstituted or substituted C1-C 20 Alkyl, undeuterated or deuterated, unsubstituted or substituted C1-C 20 Heteroalkyl, undeuterated or deuterated, unsubstituted or substituted C2-C 20 Alkenyl, undeuterated or deuterated, unsubstituted or substituted C2-C 20 Heterene, undeuterated or deuterated, unsubstituted or substituted C1-C 20 Alkoxy, carboxyl, nitrile, isonitrile, sulfonamide, phosphine, undeuterated or deuterated unsubstituted or substituted C1-C 20 Alkylamino, undeuterated or deuterated, unsubstituted or substituted C1-C 20 Alkyl silyl, undeuterated or deuterated, unsubstituted or substituted C4-C 30 Alicyclic group, undeuterated or deuterated, unsubstituted or substituted C3-C 30 Heterocyclic group, undeuterated or deuterated unsubstituted or substituted C6-C 30 Aryl, or undeuterated or deuterated unsubstituted or substituted C3-C 30 Mixed aromatics;

[0224] Optionally,

[0225] When d is 2 or 3, two adjacent R 13 and / or

[0226] When e is 2, 3, or 4, two adjacent R 14

[0227] Further, directly or indirectly, they are linked together to form unsubstituted or substituted C4-C. 20 Alicyclic, unsubstituted or substituted C3-C 20 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Mixed fragrance ring;

[0228] c is 0 or 1;

[0229] d is 0, 1, 2, or 3; and

[0230] e can be 0, 1, 2, 3, or 4.

[0231] In one exemplary embodiment, R1 to R6 and R in Equations 4A to 4D 11 To R 14 Each of the alkyl, heteroalkyl, alkenyl, heteroalkenyl, alkoxy, alkylamino, alkylsilyl, alicyclic, heteroalicyclic, aryl, and heteroaryl groups may be independently unsubstituted or substituted with deuterium, tritium, halogen, C1-C 10 Alkyl, C4-C 20 Alicyclic group, C3-C 20 heterocyclic group, C6-C 20 Aryl and C3-C 20 At least one of the heteroaryl groups is substituted. In some embodiments, two adjacent groups from R1 to R6 in formulas 4A to 4D, and two adjacent R... 13 and two adjacent R 14 The formed C4-C 20 Alicyclic, C3-C 20 Aliphatic ring, C6-C 30 Aromatic rings and C3-C 30 Each of the heterocyclic aromatic rings can be independently unsubstituted or substituted by at least one C1-C. 10 Alkyl substitution.

[0232] In yet another exemplary embodiment, L, as an auxiliary ligand B It can be a phenyl-pyridinyl ligand or an acetylacetone ligand. As an example, L... B It may have, but is not limited to, the following structures represented by Equation 5A or Equation 5B:

[0233] [Formula 5A]

[0234]

[0235] [Formula 5B]

[0236]

[0237] In Equations 5A and 5B,

[0238] R 21 R 22 and R 31 To R 33 Each is independently hydrogen, protium, deuterium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C1-C 20 Heteroalkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Heterene, unsubstituted or substituted C1-C 20 Alkoxy, carboxyl, nitrile, isonitrile, sulfonamide, phosphine, unsubstituted or substituted C1-C20 Alkylamino, unsubstituted or substituted C1-C 20 Alkylsilyl, unsubstituted or substituted C4-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 Mixed aromatics,

[0239] Optionally,

[0240] When f is 2, 3, or 4, two adjacent R 21 and / or

[0241] When g is 2, 3, or 4, two adjacent R 22 and / or

[0242] R 31 and R 32 、or R 32 and R 33

[0243] Further, directly or indirectly, they are linked together to form unsubstituted or substituted C4-C. 20 Alicyclic, unsubstituted or substituted C3-C 20 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Mixed aromatic rings; and

[0244] f and g are each 0, 1, 2, 3 or 4.

[0245] R 21 To R 22 and R 31 To R 33 Substituents or those derived from R 21 To R 22 R 31 and R 32 and / or R 33 The formed ring may be the same as the substituent or ring described in Formula 2. In one exemplary embodiment, the organometallic compound having a structure represented by Formulas 1 to 5B may include at least one of the following organometallic compounds represented by Formula 6, or may be selected from, but not limited to, the following organometallic compounds represented by Formula 6:

[0246] [Formula 6]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266] Organometallic compounds having any of the structures of Formulas 4A to 6 include a heteroaryl ligand consisting of at least five rings, thus exhibiting a rigid chemical conformation. These organometallic compounds can improve color purity and luminescence lifetime because they maintain a stable chemical conformation during luminescence. Furthermore, since the organometallic compounds can be metal complexes with bidentate ligands, the luminescence color purity and color can be easily controlled. Therefore, by applying organometallic compounds having the structures of Formulas 1 to 6 to the luminescent layer, organic light-emitting diodes (OLEDs) exhibit beneficial luminous efficiency.

[0267] The first host 344 can be a p-type host with relatively beneficial hole affinity. The first host 344 can be a biscarbazolyl organic compound represented by the structure of Formula 7.

[0268] [Formula 7]

[0269]

[0270] In Equation 7,

[0271] R 41 To R 44 Each is independently either unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 Heteroaryl, wherein when p is 2, 3, 4, 5, 6 or 7, each R 43 Whether they are the same or different, each R is equal to or different when q is 2, 3, 4, 5, 6 or 7. 44 Whether they are the same or different, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; and

[0272] p and q are each independently 0, 1, 2, 3, 4, 5, 6 or 7.

[0273] In one exemplary implementation, R 41 To R 44 Each of the aryl and heteroaryl groups can be independently unsubstituted or C1-C2 substituted. 10 Alkyl, C1-C 10 Alkyl silyl, C6-C 20 Arylsilyl, C6-C 20 Aryl and C3-C 20 At least one of the heteroaryl groups is substituted, or it is combined with C6-C 20 Aromatic rings or C3-C 20 The heterocyclic aromatic rings form a spiral structure.

[0274] As an example, the two carbazole moieties of the biscarbazole-based compound in Formula 7, which is the first body 344, can be connected to, but is not limited to, the 3-position of each carbazole moieties. R 41 To R 44 The aryl and heteroaryl groups may include aryl and heteroaryl groups as described in Formula 2. For example, R 41 To R 44 Each of these may include, but is not limited to, aryl, such as phenyl, biphenyl, terphenyl, naphthyl (e.g., 1-naphthyl or 2-naphthyl), fluorenyl (e.g., 9-10-dimethyl-9H-fluorenyl or spiro-fluorenyl), anthracene, pyrene, and / or triphenylenyl, each of which may be independently unsubstituted or substituted with cyano, C6-C 20 Arylsilyl, C6-C 20 Aryl and C3-C20 At least one of the heteroaryl groups is substituted.

[0275] More specifically, R 41 To R 44 Each of them may be the same as or different from each other, and independently includes, but is not limited to, unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl, and unsubstituted or substituted triphenylenyl. Each of p and q in Formula 7 may independently be 0, 1, 2, or 3, for example, 0 or 1. In an exemplary embodiment, the first body 344 may include at least one of the following organic compounds represented by Formula 8, or may be selected from, but not limited to, the following organic compounds represented by Formula 8:

[0276] [Formula 8]

[0277]

[0278]

[0279]

[0280] EML 340 may further include a second host 346 and a first host 344. The second host 346 may be an n-type host with relatively favorable electron affinity properties. The second host 346 may include an azazinyl organic compound represented by the structure of Formula 9:

[0281] [Formula 9]

[0282]

[0283] In Equation 9,

[0284] R 51 and R 52 Each is independently unsubstituted or substituted C6-C 30 aryl or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0285] Y1, Y2, and Y3 are each independently CR 53 Or N, where at least one of Y1, Y2, and Y3 is N;

[0286] R 53 Independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C6-C 30aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0287] R 61 To R 68 Each is independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 10 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 The heterocyclic aromatic rings form a spiral structure.

[0288] Optionally,

[0289] R 61 To R 68 Two adjacent groups in the form are further directly or indirectly linked together to form an unsubstituted or substituted C6-C. 30 Aromatic ring, or unsubstituted or substituted C3-C 30 heterocyclic aromatic rings, optionally, unsubstituted or substituted C6-C 30 Aromatic rings and unsubstituted or substituted C3-C 30 Each heterocyclic ring independently interacts with unsubstituted or substituted C6-C. 20 Aromatic ring, or unsubstituted or substituted C3-C 20 Heteroaromatic rings form a spiral structure;

[0290] R 69 and R 70 Each is independently unsubstituted or substituted C1-C 10 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30Heteroaromatic rings form a helical structure, wherein when j is 2 or 3, each R 69 They are either the same or different, and when k is 2 or 3, each R 70 Whether they are the same or different,

[0291] Optionally,

[0292] When j is 2 or 3, two adjacent R 69 and / or

[0293] When k is 2 or 3, two adjacent R 70

[0294] Further, directly or indirectly, they are linked together to form unsubstituted or substituted C6-C. 30 Aromatic ring, or unsubstituted or substituted C3-C 30 heterocyclic aromatic rings, optionally, unsubstituted or substituted C6-C 30 Aromatic rings and unsubstituted or substituted C3-C 30 Each heterocyclic ring independently interacts with unsubstituted or substituted C6-C. 20 Aromatic ring, or unsubstituted or substituted C3-C 20 Heteroaromatic rings form a spiral structure;

[0295] L represents a single bond, and is either unsubstituted or substituted C6-C. 30 Aryl styrene, or unsubstituted or substituted C3-C 30 Hybrid aromatic styrene, optionally, unsubstituted or substituted C6-C 30 Aryl styrene and unsubstituted or substituted C3-C 30 Each heteroarylene independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0296] Z is either O or S; and

[0297] j and k are each independently 0, 1, 2 or 3.

[0298] In one exemplary implementation, R 51 To R 53 and R 61 To R 70 Each of the aryl and heteroaryl groups, each of the aryl and heteroaryl groups, and / or each of the aromatic and heteroaryl rings may be independently unsubstituted or C1-C2 substituted. 10 Alkyl, C6-C 20 Aryl and C3-C 20 At least one of the heteroaryl groups is substituted, or it is combined with C6-C. 20 Aromatic rings or C3-C 20The heterocyclic aromatic rings form a spiral structure.

[0299] As an example, the azazine moiety, L-position, or carbazoyl moiety in Formula 9, which is the second body 346, can be attached to, but is not limited to, the 2- or 3-position, and / or 6- or 7-position of the dibenzofuran or dibenzothiophene ring. When two adjacent groups of the carbazoyl moiety form an aromatic or heteroaromatic ring, the two elements at the 2- and 3-positions, and / or 6- and 7-positions of the carbazoyl moiety can form an aromatic or heteroaromatic ring, but are not limited thereto.

[0300] From R in Equation 9 61 To R 70 The aromatic or heteroaromatic ring formed by two adjacent groups in the ring may include, but is not limited to, benzene rings, naphthyl rings, anthracene rings, pyridine rings, furan rings, thiophene rings, indole rings, benzofuran rings, and benzothiophene rings, each of which may be independently unsubstituted or C1-C2 substituted. 10 Alkyl, C6-C 20 Aryl and C3-C 20 At least one of the heteroaryl groups is substituted. As an example, such aromatic or heteroaryl rings may include indole, indole, benzofuran, and benzothiophene rings, each of which may be unsubstituted or substituted with these groups.

[0301] R in Equation 9 51 To R 53 and R 61 To R 70 The aryl and heteroaryl groups in the formula may include aryl and heteroaryl groups as described in Formula 2. For example, R 51 To R 53 and R 61 To R 70 Each of these components independently comprises phenyl, naphthyl, pyridyl, carbazole, and fluorenyl, and each may be unsubstituted or C1-C2 substituted. 10 Alkyl, C6-C 20 Aryl and C3-C 20 At least one of the heteroaryl groups is substituted.

[0302] The aryl and heteroaryl groups in Formula 9 may include divalent bridging groups corresponding to the aryl and heteroaryl groups described in Formula 2. For example, the aryl and heteroaryl groups may include, but are not limited to, phenylene, naphthyl, and pyridyl groups, each of which may be independently unsubstituted or substituted with at least one aryl group such as phenyl, naphthyl, anthracene, and phenanthrene. In an exemplary embodiment, the second body 346 may include at least one of the following organic compounds represented by Formula 10, or may be selected from, but not limited to, the following organic compounds represented by Formula 10:

[0303] [Formula 10]

[0304]

[0305]

[0306]

[0307]

[0308] Based on the total weight of the components in EML 340, the content of the body comprising the first body 344 and the second body 346 in EML 340 may be, but is not limited to, from about 50% by weight to about 90% by weight, for example, from about 80% by weight to about 95% by weight. Based on the total weight of the components in EML 340, the content of the dopant 342 in EML 340 may be, but is not limited to, from about 1% by weight to 10% by weight, for example, from about 5% by weight to 20% by weight. When EML 340 comprises the first body 344 and the second body 346, the first body 344 and the second body 346 may be mixed, but is not limited to having a weight ratio between about 4:1 and about 1:4, for example, a weight ratio between about 3:1 and about 1:3. As an example, EML 340 may have a thickness of, but is not limited to, from about 100 nm to about 500 nm.

[0309] HIL 310 is disposed between the first electrode 210 and HTL 320, and can improve the interfacial properties between the inorganic first electrode 210 and the organic HTL 320. In one exemplary embodiment, HIL 310 may include, but is not limited to: 4,4',4”-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4”-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4”-tris(N-(naphthyl-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4”-tris(N-(naphthyl-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazole-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4”-diamine (NPB; NPD), 1,4,5,8,9,11-hexaazatriphenyl Hexanitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile; HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrene sulfonate (PEDOT / PSS), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethylamine (F4TCNQ), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine, N,N'-diphenyl-N,N'-di[4-(N,N'-diphenylamino)phenyl]benzidine (NPNPB), and / or combinations thereof.

[0310] As an example, HIL 310 may have a thickness of approximately 50 nm to approximately 150 nm. Depending on the characteristics of OLED D1, HIL 310 may be omitted.

[0311] HTL 320 is disposed adjacent to EML 340 between the first electrode 210 and EML 340, and includes hole transport material 322. The hole transport material may be a spirodifluorene-based material represented by the structure of Formula 11:

[0312] [Equation 11]

[0313]

[0314] In Equation 11,

[0315] R 61 and R 62 Each is independently unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, of which R61 and R 62 At least one of them is a polycyclic aryl or polycyclic heteroaryl, optionally, an unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0316] R 63 To R 66 Each is independently unsubstituted or substituted C1-C 20 Alkyl, or unsubstituted or substituted C6-C 30 Aryl, wherein when r is 2, 3 or 4, each R 63 Whether they are the same or different, when s is 2, 3 or 4, each R 64 Whether they are the same or different, when t is 2, 3 or 4, each R 65 Whether they are the same or different, when u is 2, 3 or 4, each R 66 They are the same or different from each other;

[0317] L1 to L3 are each independently a single bond, unsubstituted or substituted C6-C. 30 Aryl styrene, or unsubstituted or substituted C3-C 30 Hybrid aromatic styrene, optionally, unsubstituted or substituted C6-C 30 Aryl styrene and unsubstituted or substituted C3-C 30 Each heteroarylene independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0318] r, s, and t are each independently 0, 1, 2, 3, or 4; and

[0319] u can be 0, 1, 2 or 3.

[0320] In one exemplary embodiment, R in Equation 11 61 To R 66 C6-C 30 Aryl and C3-C 30 Heteroaryl and / or L1 to L3 C6-C 30 Aryl groups and C3-C 30 Each of the heteroaryl groups can be independently unsubstituted or C1-C substituted. 10 Alkyl, C6-C 20 Aryl and C3-C 20 At least one of the heteroaryl groups is substituted, or it is combined with C6-C20 Aromatic rings or C3-C 20 The heterocyclic aromatic rings form a spiral structure.

[0321] As an example, aromatic or heteroaromatic amino groups can be directly or via a bridging group L1 connected to the 2'- or 4'-position of the spirodifluorene moiety, but are not limited thereto. In one exemplary embodiment, it can be R in Formula 11. 61 and R 62 One of the polycyclic aryl and polycyclic heteroaryl groups may include, but is not limited to, fluorenyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, and naphthyl (e.g., 2-naphthyl), each of which may be independently unsubstituted or C1-C2 substituted. 10 Alkyl, C6-C 20 Aryl and C3-C 20 At least one of the heteroaryl groups is substituted, or it may be substituted with an unsubstituted or substituted C6-C group. 20 Aromatic ring, or unsubstituted or substituted C3-C 20 The heterocyclic aromatic rings form a spiral structure.

[0322] Alternatively, each of L1 to L3 in Formula 11 may be, but is not limited to, a single bond or an unsubstituted or substituted phenyl group. In one exemplary embodiment, hole transport material 322 may include at least one of the following spirodifluorenyl organic compounds of Formula 12, or may be selected from, but not limited to, the following spirodifluorenyl organic compounds of Formula 12:

[0323] [Equation 12]

[0324]

[0325]

[0326]

[0327] Hole transport material 322 having the structure of Formulas 11 to 12 has beneficial hole transport characteristics and energy levels suitable for dopant 342, first host 344, and second host 346 in EML 340. When hole transport material 326 having the structure of Formulas 11 to 12 is applied to HTL 320, holes can be rapidly injected into EML 320.

[0328] ETL 360 and EIL 370 can be sequentially laminated between EML 340 and the second electrode 220. The electron transport material 362 included in ETL 360 has high electron mobility to stably provide electrons to EML 340 via rapid electron transport. Electron transport material 362 can be a benzimidazole-based material represented by the structure of Formula 13:

[0329] [Equation 13]

[0330]

[0331] In Equation 13,

[0332] R 71 To R 73 Each is independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spirostructure, in which R 71 To R 73 One of them has a structure represented by Equation 14:

[0333] [Formula 14]

[0334]

[0335] In Equation 14,

[0336] L4 is a single bond, unsubstituted or substituted C6-C. 30 Aryl styrene, or unsubstituted or substituted C3-C 30 Hybrid aromatic styrene, optionally, unsubstituted or substituted C6-C 30 Aryl styrene and unsubstituted or substituted C3-C 30 Each heteroarylene independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0337] When w is 0, Ar1 is unsubstituted or substituted C6-C. 30 aryl, or when w is 1, Ar1 is unsubstituted or substituted C6-C. 30 Aryl alkyl group, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C6-C 30 Aryl groups react independently with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure;

[0338] Ar2 is unsubstituted or substituted C6-C 30Aryl;

[0339] R 74 It is hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl; and

[0340] w is 0 or 1.

[0341] In one exemplary embodiment, R in Equations 13 and 14 71 To R 74 C6-C of Ar1 30 Aryl and C3-C 30 Each of the heteroaryl groups, and / or the C6-C of L, Ar1 and Ar2 30 Aryl groups and C3-C 30 Each of the heteroaryl groups was independently unsubstituted or C1-C 10 Alkyl, C6-C 20 Aryl and C3-C 20 At least one of the heteroaryl groups is substituted, or it is combined with C6-C 20 Aromatic rings or C3-C 20 The heterocyclic aromatic rings form a spiral structure.

[0342] As an example, L4 in Formula 14 can be a single bond or a phenylene group. When w is 0, Ar1 in Formula 14 can be, but is not limited to, anthracene, triphenylenyl, pyrene, or phenanthryl, each of which can be independently unsubstituted or substituted. Alternatively, when w is 1, Ar1 in Formula 14 can be, but is not limited to, anthracene, phenylene, pyrene, or phenanthryl, each of which can be independently unsubstituted or substituted. Alternatively, Ar2 in Formula 14 can be, but is not limited to, phenyl, naphthyl (e.g., 2-naphthyl), phenatenyl, or phenanthryl, each of which can be independently unsubstituted or substituted, and R in Formula 14... 74 It can be, but is not limited to, hydrogen, unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl (e.g., 1-naphthyl or 2-naphthyl).

[0343] In one exemplary implementation, R in Equation 13 71 The substituent portion may have the structure of Formula 14. The electron transport material 362 having this portion may have the structure of Formula 15:

[0344] [Formula 15]

[0345]

[0346] In Equation 15,

[0347] R72 To R 74 Each is independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl; and

[0348] Ar1 is unsubstituted or substituted C6-C 30 Fang Chengji.

[0349] As an example, R in Equation 15 74 It can be hydrogen, unsubstituted or substituted C1-C 10 Alkyl, or unsubstituted or substituted C6-C 20 Aryl. In one exemplary embodiment, the electron transport material 362 may include at least one of the benzimidazole-based organic compounds of Formula 16, or may be selected from, but not limited to, benzimidazole-based organic compounds of Formula 16:

[0350] [Formula 16]

[0351]

[0352]

[0353] The electron transport material 362 having a structure of Formulas 13 to 16 has beneficial electron transport properties and energy levels suitable for the dopant 342, the first host 344, and the second host 346 in the EML 340. When the electron transport material 362 having a structure of Formulas 13 to 16 is applied to the EML 360, electrons can be rapidly injected into the EML 340.

[0354] EIL 370 is disposed between the second electrode 220 and ETL 360 and can improve the physical properties of the second electrode 220, thereby enhancing the lifetime of OLED D1. In one exemplary embodiment, EIL 370 may include, but is not limited to, alkali metal halides or alkaline earth metal halides such as LiF, CsF, NaF, BaF2, and the like, and / or organometallic compounds such as Liq, lithium benzoate, lithium stearate, and the like. Alternatively, EIL 370 may be omitted. Each of ETL 360 and EIL 370 may independently have a thickness of, but not limited to, about 100 nm to about 400 nm. Alternatively, EIL 370 may be omitted.

[0355] In an alternative aspect, electron transport material 362 and electron injection material can be mixed to form a single ETL-EIL. Electron transport material 362 and electron injection material can be mixed, but are not limited to having a weight ratio of about 4:1 to about 1:4, for example, a weight ratio of about 2:1 to about 1:2.

[0356] When holes are transferred to the second electrode 220 via EML 340 and / or electrons are transferred to the first electrode 210 via EML 340, the OLED D1 may have a short lifetime and reduced luminous efficiency. To prevent these phenomena, the OLED D1 according to this aspect of the disclosure may have at least one exciton blocking layer adjacent to EML 340.

[0357] For example, OLED D1 may include EBL 330 between HTL 320 and EML 340 to control and prevent electron transfer. In one exemplary embodiment, EBL 330 may include, but is not limited to: TCTA, tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, TAPC, MTDATA, 1,3-bis(carbazole-9-yl)phenyl (mCP), 3,3'-bis(N-carbazole)-1,1'-biphenyl (mCBP), CuPc, N,N'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD), TDAPB, DCDPA, 2,8-bis(9-phenyl-9H-carbazole-3-yl)dibenzo[b,d]thiophene, and combinations thereof.

[0358] In addition, the OLED D1 may further include an HBL 350 as a second exciton blocking layer between the EML 340 and the ETL 360, thereby preventing holes from migrating from the EML 340 to the ETL 360. In one exemplary embodiment, the HBL 350 may include, but is not limited to, at least one of the following compounds that can be used in the ETL 360: oxadiazole compounds, triazole compounds, phenanthroline compounds, benzoxazole compounds, benzothiazole compounds, benzimidazole compounds, and triazine compounds.

[0359] For example, HBL 350 may include compounds having a relatively low HOMO energy level compared to the luminescent material in EML 340. HBL 350 may include, but is not limited to: tri-(8-hydroxyquinoline)aluminum (Alq3), bis(2-methyl-8-quinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), lithium quinoline (Liq), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis-4,5-(3,5-di-3-pyridylphenyl)-2-methylpyrimidine (B3PYMPM), bis[2-(diphenylphosphine)phenyl]ether oxide (DPEPO), 9-(6-(9H-carbazole-9-yl)pyridin-3-yl)-9H-3,9'-biscarbazole, diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), and combinations thereof.

[0360] Because organometallic compounds with structures of formulas 1 to 6 have rigid chemical conformations, they can maintain their stable chemical conformations during luminescence, exhibiting beneficial color purity and luminescence lifetime. Modifying the structure of bidentate ligands and the substituents of the ligands allows organometallic compounds to control their luminescence color.

[0361] Furthermore, EML 340 may further include a first body 344 with beneficial hole transport properties and a second body 346 with beneficial electron transport properties. Because charge and exciton energy are rapidly transferred from the first body 344 (a biscarbazolium compound) and the second body 346 (an azazine compound) to the dopant 342, OLED D1 is able to reduce its driving voltage and improve its luminous efficiency and luminous lifetime.

[0362] Furthermore, OLED D1 includes an HTL 320 comprising a hole transport material 322 having advantageous hole transport properties, and an ETL 360 comprising an electron transport material 362 having advantageous electron transport properties, disposed adjacent to EML 340. Therefore, holes and electrons can be injected into EML 340 from HTL 320 and ETL 360.

[0363] In the first aspect of the above-described exemplary method, the OLED and organic light-emitting display device include a single light-emitting element that emits green light. Alternatively, the OLED may include multiple light-emitting elements (see [link to documentation]). Figure 5 and Figure 6 ( ), wherein at least one of them includes a dopant 342, a first body 344 and an optional second body 346.

[0364] In another exemplary embodiment, the organic light-emitting display device can achieve full color including white. Figure 4A schematic cross-sectional view of an organic light-emitting display device according to another exemplary embodiment of the present disclosure is shown.

[0365] As Figure 4 shown, the organic light-emitting display device 400 includes a first substrate 402 that defines each of a red pixel region RP, a green pixel region GP, and a blue pixel region BP, a second substrate 404 facing the first substrate 402, a thin-film transistor Tr located on the first substrate 402, an OLED D disposed between the first substrate 402 and the second substrate 404 and emitting white (W) light, and a color filter layer 480 disposed between the OLED D and the second substrate 404.

[0366] Each of the first substrate 402 and the second substrate 404 may include, but is not limited to, glass, a flexible material, and / or a polymer plastic. For example, each of the first substrate 402 and the second substrate 404 may be made of PI, PES, PEN, PET, PC, and / or a combination thereof. The first substrate 402 on which the thin-film transistor Tr and the OLED D are disposed forms an array substrate.

[0367] A buffer layer 406 may be provided on the first substrate 402. The thin-film transistor Tr is disposed on the buffer layer 406, corresponding to each of the red pixel region RP, the green pixel region GP, and the blue pixel region BP. The buffer layer 406 may be omitted.

[0368] A semiconductor layer 410 is disposed on the buffer layer 406. The semiconductor layer 410 may be made of an oxide semiconductor material or polysilicon or may include an oxide semiconductor material or polysilicon.

[0369] A gate insulating layer 420 is disposed on the semiconductor layer 410. The gate insulating layer 420 includes an insulating material, for example, an inorganic insulating material such as silicon oxide (SiO x , where 0 < x ≤ 2) or silicon nitride (SiN x , where 0 < x ≤ 2).

[0370] A gate 430 made of a conductive material such as metal is disposed on the gate insulating layer 420 so as to correspond to the center of the semiconductor layer 410. An interlayer insulating layer 440 is disposed on the gate 430. The interlayer insulating layer 440 includes an insulating material, for example, an inorganic insulating material such as SiO x or SiN x or an organic insulating material such as benzocyclobutene or photo-acryl.

[0371] The interlayer insulating layer 440 has a first semiconductor layer contact hole 442 and a second semiconductor layer contact hole 444, which expose or do not cover a portion of the surface closer to the opposite end than the center of the semiconductor layer 410. The first semiconductor layer contact hole 442 and the second semiconductor layer contact hole 444 are disposed on opposite sides of the gate 430 and spaced apart from the gate 430.

[0372] Source 452 and drain 454, made of or including a conductive material such as metal, are disposed on the interlayer insulating layer 440. Source 452 and drain 454 are spaced apart from each other relative to the gate 430. Source 452 and drain 454 contact opposite sides of the semiconductor layer 410 through a first semiconductor layer contact hole 442 and a second semiconductor layer contact hole 444, respectively.

[0373] Semiconductor layer 410, gate 430, source 452 and drain 454 constitute a thin-film transistor Tr that acts as a driving element.

[0374] although Figure 4 Not shown, gate lines GL and data lines DL that intersect to define pixel region P, and switching elements Ts connected to gate lines GL and data lines DL may be further formed in pixel region P. Switching elements Ts are connected to thin-film transistors Tr, which serve as driving elements. Furthermore, power lines PL are parallel to and spaced apart from gate lines GL or data lines DL, and thin-film transistors Tr may further include storage capacitors Cst configured to maintain a constant voltage at gate 430 within a frame.

[0375] A passivation layer 460 is disposed on the source 452 and the drain 454, and covers the thin-film transistor Tr over the entire first substrate 402. The passivation layer 460 has a drain contact hole 462 that may or may not cover the drain 454 of the thin-film transistor Tr.

[0376] The OLED D is located on the passivation layer 460. The OLED D includes a first electrode 510 connected to the drain 454 of the thin film transistor Tr, a second electrode 520 facing the first electrode 510, and a light-emitting layer 530 disposed between the first electrode 510 and the second electrode 520.

[0377] The first electrode 510 formed for each pixel region RP, GP, or BP can be an anode and may include a conductive material with a relatively high work function value. For example, the first electrode 510 may include, but is not limited to, ITO, IZO, ITZO, SnO, ZnO, ICO, AZO, and / or the like. Alternatively, a reflective electrode or reflective layer may be disposed below the first electrode 510. For example, the reflective electrode or reflective layer may include, but is not limited to, Ag or APC alloys.

[0378] A dam layer 464 is disposed on the passivation layer 460 to cover the edge of the first electrode 510. The dam layer 464 may or may not cover the center of the first electrode 510 corresponding to each of the red pixel RP, green pixel GP, and blue pixel BP. The dam layer 464 may be omitted.

[0379] A light-emitting layer 530, which may include a light-emitting portion, may be disposed on the first electrode 510. For example... Figure 5 and Figure 6 As shown, the light-emitting layer 530 may include a plurality of light-emitting portions 600, 700, 700' and 800 and at least one charge-generating layer 680 and 780. Each of the light-emitting portions 600, 700, 700' and 800 includes at least one light-emitting material layer and may further include HIL, HTL, EBL, HBL, ETL and / or EIL.

[0380] The second electrode 520 can be disposed on a substrate 402 on which a light-emitting layer 530 may be disposed. The second electrode 520 can be disposed over the entire display area and may include a conductive material having a relatively low work function value compared to the first electrode 510, and may be a cathode. For example, the second electrode 520 may include, but is not limited to, Al, Mg, Ca, Ag, alloys thereof and / or combinations thereof, such as Al-Mg.

[0381] Since in the organic light-emitting display device 400 according to the second embodiment of the present disclosure, light emitted from the light-emitting layer 530 is incident on the color filter layer 480 through the second electrode 520, the second electrode 520 has a thin thickness so that light can be transmitted.

[0382] A color filter layer 480 is disposed on the OLED D and includes a red color filter pattern 482, a green color filter pattern 484, and a blue color filter pattern 486, each corresponding to a red pixel RP, a green pixel GP, and a blue pixel BP, respectively. Although Figure 4 Not shown, the color filter layer 480 can be attached to the OLED D via an adhesive layer. Alternatively, the color filter layer 480 can be directly disposed on the OLED D.

[0383] Furthermore, an encapsulation film can be disposed on the second electrode 520 to prevent or reduce the penetration of external moisture into the OLEDD. The encapsulation film may have, but is not limited to, a laminated structure comprising, but not limited to, a first inorganic insulating film, an organic insulating film, and a second inorganic insulating film. Figure 2 (170 in the text). Furthermore, the polarizing plate can be attached to the second substrate 404 to reduce the reflection of external light. For example, the polarizing plate can be a circular polarizing plate.

[0384] exist Figure 4In this configuration, light emitted from the OLED D is transmitted through the second electrode 520, and a color filter layer 480 is disposed on the OLED D. Alternatively, light emitted from the OLED D is transmitted through the first electrode 510, and the color filter layer 480 may be disposed between the OLED D and the first substrate 402. Furthermore, a color conversion layer may be formed or disposed between the OLED D and the color filter layer 480. The color conversion layer may include a red conversion layer, a green conversion layer, and a blue conversion layer, respectively disposed for each pixel (RP, GP, and BP) to convert white (W) light into each of red, green, and blue light, respectively. Alternatively, the organic light-emitting display device 400 may include a color conversion film instead of the color filter layer 480.

[0385] As described above, white (W) light emitted from OLED D is transmitted through red filter pattern 482, green filter pattern 484 and blue filter pattern 486, each of which corresponds to the red pixel region RP, green pixel region GP and blue pixel region BP respectively, so that red light, green light and blue light are displayed in the red pixel region RP, green pixel region GP and blue pixel region BP respectively.

[0386] Figure 5 A schematic cross-sectional view of an organic light-emitting diode (OLED) with a series-connected structure of two light-emitting portions is shown. Figure 5 As shown, an OLED D2 according to an exemplary embodiment of the present disclosure includes a first electrode 510 and a second electrode 520, and a light-emitting layer 530 disposed between the first electrode 510 and the second electrode 520. The light-emitting layer 530 includes a first light-emitting portion 600 disposed between the first electrode 510 and the second electrode 520, a second light-emitting portion 700 disposed between the first light-emitting portion 600 and the second electrode 520, and a charge-generating layer (CGL) 680 disposed between the first light-emitting portion 600 and the second light-emitting portion 700.

[0387] The first electrode 510 may be an anode and may include a conductive material with a relatively high work function value, such as TCO. For example, the first electrode 510 may include, but is not limited to, ITO, IZO, ITZO, SnO, ZnO, ICO, AZO, and / or the like. The second electrode 520 may be a cathode and may include a conductive material with a relatively low work function value. For example, the second electrode 520 may include, but is not limited to, Al, Mg, Ca, Ag, alloys thereof, and / or combinations thereof, such as Al-Mg.

[0388] The first light-emitting portion 600 includes a first EML (EML1) 640. The first light-emitting portion 600 may further include at least one of the following: a HIL 610 disposed between the first electrode 510 and EML1 640; a first HTL (HTL1) 620 disposed between HIL 610 and EML1 640; and a first ETL (ETL1) 660 disposed between EML1 640 and CGL 680. Alternatively, the first light-emitting portion 600 may further include a first EBL (EBL1) 630 disposed between HTL1 620 and EML1 640; and / or a first HBL (HBL1) 650 disposed between EML1 640 and ETL1 660.

[0389] The second light-emitting portion 700 includes a second EML (EML2) 740. The second light-emitting portion 700 may further include at least one of a second HTL (HTL2) 720 disposed between CGL680 and EML2 740, a second ETL (ETL2) 760 disposed between the second electrode 520 and EML2 740, and an EIL 770 disposed between the second electrode 520 and ETL2 760. Alternatively, the second light-emitting portion 700 may further include a second EBL (EBL2) 730 disposed between HTL2 720 and EML2 740, and / or a second HBL (HBL2) 750 disposed between EML2 740 and ETL2 760.

[0390] At least one of EML1 640 and EML2 740 may include a dopant 742, a first body 744, and / or a second body 746 to emit green or yellow-green. The other of EML1 640 and EML2 740 may emit blue, enabling OLED D2 to achieve white (W) emission. OLED D2 in which EML2 740 emits green or yellow-green will be described in detail below.

[0391] Alternatively, at least one of HTL1 620 and HTL2 720 includes hole transport material 722, and at least one of ETL1 660 and ETL2 760 includes electron transport material 762, so that holes and electrons can be rapidly injected into adjacent EMLs 640 and 740.

[0392] HIL 610 is disposed between the first electrode 510 and HTL1 620, and improves the interface properties between the inorganic first electrode 510 and the organic HTL1 620. In an exemplary embodiment, HIL 610 may include, but is not limited to, MTDATA, NATA, 1T-NATA, 2T-NATA, CuPc, TCTA, NPB (NPD), HAT-CN, TDAPB, PEDOT / PSS, F4TCNQ, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine, NPNPB, and combinations thereof. Depending on the characteristics of OLED D2, HIL 610 may be omitted.

[0393] In one exemplary embodiment, HTL1 620 may include a spirodifluorenyl organic compound having a structure of Formula 11 to Formula 12. Alternatively, HTL1 620 may include, but is not limited to: N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), NPB (NPD), N,N'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly[N,N'-bis(4-tert-butyl)-N,N'-bis(phenyl)-biphenyldiamine] (Poly-TPD), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-secondary butylphenyl)diphenylamine)] ))](TFB), 1,1-bis(4-(N,N'-di(p-tolyl)amino)phenyl)cyclohexane (TAPC), 3,5-bis(9H-carbazole-9-yl)-N,N-diphenylaniline (DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl-4-amine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, and combinations thereof.

[0394] HTL2 720 may include hole transport material 722. Hole transport material 722 may include spirodifluorene-based organic compounds having a structure of formula 11 to formula 12.

[0395] Each of ETL1 660 and ETL2 760 respectively promotes electron transport in each of the first light-emitting portion 600 and the second light-emitting portion 700. As an example, ETL1 660 may comprise a benzimidazole-based organic compound having a structure of formula 13 to formula 16.

[0396] Alternatively, ETL1 660 may include, but is not limited to, at least one of the following: diazole compounds, triazole compounds, phenanthroline compounds, benzoxazole compounds, benzothiazole compounds, benzimidazole compounds, triazine compounds, and the like.

[0397] As an example, ETL1 660 may include, but is not limited to: Alq3, BAlq, Liq, PBD, spiro-PBD, 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthyl-2-yl)4,7-diphenyl-1,10-phenanthroline (NBphen), BCP, 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tris(p 3-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-(N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alt-2,7-(9,9-dioctylfluorene)] (PFNBr), tris(phenylquinoxaline) (TPQ), TSPO1, 2-[4-(9,10-di-2-naphthyl-2-yl-2-anthracene-2-yl)phenyl]1-phenyl-1H-benzimidazole (ZADN), and combinations thereof.

[0398] ETL2 760 includes electron transport material 762. Electron transport material 762 may include benzimidazole-based organic compounds having structures of formulas 13 to 16.

[0399] EIL 770 is disposed between the second electrode 520 and ETL2 760 and can improve the physical properties of the second electrode 520, thus improving the lifetime of OLED D2. In one exemplary embodiment, EIL 770 may include, but is not limited to, alkali metal halides or alkaline earth metal halides such as LiF, CsF, NaF, BaF2, and the like, and / or organometallic compounds such as Liq, lithium benzoate, lithium stearate, and the like.

[0400] Each of EBL1 630 and EBL2 730 may independently include, but is not limited to, TCTA, tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, TAPC, MTDATA, mCP, mCBP, CuPc, DNTPD, TDAPB, DCDPA, 2,8-bis(9-phenyl-9H-carbazole-3-yl)dibenzo[b,d]thiophene, and combinations thereof.

[0401] Each of HBL1 650 and HBL2 750 may include, but is not limited to, at least one of the following: oxadiazoles, triazoles, phenanthrolines, benzoxazoles, benzothiazoles, benzimidazoles, and triazines, which may each be used in ETL1 660 and ETL2 760. For example, each of HBL1 650 and HBL2 750 may independently include, but is not limited to, Alq3, BAlq, Liq, PBD, spiro-PBD, BCP, B3PYMPM, DPEPO, 9-(6-(9H-carbazol-9-yl)pyridin-3-yl)-9H-3,9'-biscarbazole, TSPO1, and combinations thereof.

[0402] CGL 680 is disposed between the first light-emitting part 600 and the second light-emitting part 700. CGL 680 includes an N-type CGL (N-CGL) 685 disposed adjacent to the first light-emitting part 600 and a P-type CGL (P-CGL) 690 disposed adjacent to the second light-emitting part 700. N-CGL 685 injects electrons into EML1 640 of the first light-emitting part 600, and P-CGL 690 injects holes into EML2 740 of the second light-emitting part 700.

[0403] N-CGL 685 can be an organic layer doped with alkali metals such as Li, Na, K, and Cs and / or alkaline earth metals such as Mg, Sr, Ba, and Ra. The main components of N-CGL 685 may include, but are not limited to, Bphen and MTDATA. The content of alkali metals or alkaline earth metals in N-CGL 685 can be between about 0.01% by weight and about 30% by weight.

[0404] P-CGL 690 may include, but is not limited to, the option of WO. x MoO xInorganic materials consisting of V2O5 and combinations thereof, and / or organic materials selected from NPD, HAT-CN, F4TCNQ, TPD, N,N,N',N'-tetranaphthalenebenzidine (TNB), TCTA, N,N'-dioctyl-3,4,9,10-peryldicarboximide (PTCDI-C8) and combinations thereof.

[0405] EML1 640 can be a blue EML. In this case, EML1 640 can be a blue EML, a sky blue EML, or a dark blue EML. EML1 640 may include a blue body and blue dopants.

[0406] For example, the blue body may include, but is not limited to, mCP, 9-(3-(9H-carbazole-9-yl)phenyl)-9H-carbazole-3-onitrile (mCP-CN), mCBP, CBP-CN, 9-(3-(9H-carbazole-9-yl)phenyl)-3-(diphenylphosphineoxy)-9H–carbazole (mCPPO1), 3,5-bis(9H-carbazole-9-yl)biphenyl (Ph-mCP), TSPO1, 9-(3'-(9H-carbazole-9-yl)-[1,1'- Biphenyl[3-yl]-9H-pyrido[2,3-b]indole (CzBPCb), bis(2-methylphenyl)diphenylsilane (UGH-1), 1,4-bis(triphenylsilyl)benzene (UGH-2), 1,3-bis(triphenylsilyl)benzene (UGH-3), 9,9-spirodifluorene-2-yl-diphenyl-phosphine oxide (SPPO1), 9,9'-(5-(triphenylsilyl)-1,3-phenylene)bis(9H-carbazole) (SimCP), and combinations thereof.

[0407] Blue dopants may include at least one of blue phosphorescent materials, blue fluorescent materials, and blue delayed fluorescent materials. As examples, blue dopants may include, but are not limited to, perylene, 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), 4-(di-p-tolylamino)-4-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), and 2,7-bis(4-diphenylamino)styryl)-9,9-heterocyclic fluorene (spiro-DP). VBi), [1,4-bis[2-[4-[N,N-di(p-tolyl)amino]phenyl]vinyl]benzene (DSB), 1,4-bis-[4-(N,N-diphenyl)amino]styrylbenzene (DSA), 2,5,8,11-tetra-tert-butylperylene (TBPe), bis(2-(2-hydroxyphenyl)-pyridine)beryllium (Bepp2), 9-(9-phenylcarbazole-3-yl)-10-(naphth-1-yl)anthracene (PCAN), hydroxyl-tris(1- phenyl-3-methylimidazolin-2-pylidene-C,C(2)'iridium(III)(mer-Tris(1-phenyl-3-methylimidazolin-2-ylidene-C,C(2)'iridium(III), mer-Ir(pmi)3), facet-tris(1,3-diphenyl-benzimidazolin-2-pylidene-C,C(2)'iridium(III)(fac-Tris(1,3-diphenyl- benzimidazolin-2-ylidene-C,C(2)'iridium(III), fac-Ir(dpbic)3), bis(3,4,5-trifluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III))(Ir(tfpd)2pic), tris(2-(4,6-difluorophenyl)pyridine)iridium(III))(Ir(Fppy)3), bis[2-(4,6-difluorophenyl)pyridine-C 2 ,N](pyridinecarboxylic acid)iridium(III) (FIrpic), and combinations thereof.

[0408] EML2 740 may include a lower EML (first layer) 740A disposed between EBL2 730 and HBL2 750, and an upper EML (second layer) 740B disposed between the lower EML 740A and HBL2 750. One of the lower EML 740A and the upper EML 740B may emit red, and the other of the lower EML 740A and the upper EML 740B may emit green. The EML2 740 in which the lower EML 740A emits red and the upper EML 740B emits green will be described in detail below.

[0409] EML 740A may include a red host and red dopants. The red host may include, but is not limited to, mCP-CN, CBP, mCBP, mCP, DPEPO, 2,8-bis(diphenylphospho)dibenzothiophene (PPT), 1,3,5-tris[(3-pyridyl)-phenol-3-yl]benzene (TmPyPB), 2,6-bis(9H-carbazole-9-yl)pyridine (PYD-2Cz), 2,8-bis(9H-carbazole-9-yl)dibenzothiophene (DCzDBT), 3',5'-bis(carbazole-9-yl) )-[1,1'-biphenyl]-3,5-dicarboxynitrile (DCzTPA), 4'-(9H-carbazole-9-yl)biphenyl-3,5-dicarboxynitrile (pCzB-2CN), 3'-(9H-carbazole-9-yl)biphenyl-3,5-dicarboxynitrile (mCzB-2CN), TSPO1, 9-(9-phenyl-9H-carbazole-6-yl)-9H-carbazole (CCP), 4-(3-( Triphenylene-2-yl)phenyl)dibenzo[b,d]thiophene, 9-(4-(9H-carbazol-9-yl)phenyl)-9H-3,9'-biscarbazole, 9-(3-(9H-carbazol-9-yl)phenyl)-9H-3,9'-biscarbazole, 9-(6-(9H-carbazol-9-yl)pyridin-3-yl)-9H-3,9'-biscarbazole), 9,9'-diphenyl-9H,9'H-3,3'-biscarbazole (BCzPh), 1,3,5-tris(carbazole) 9-yl)benzene (TCP), TCTA, 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 2,7-bis(carbazole-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,2',7,7'-tetra(carbazole-9-yl)-9,9-spirofluorene (Spiro-CBP), 3,6-bis(carbazole-9-yl)-9-(2-ethylhexyl)-9H-carbazole (TCz1), and combinations thereof.

[0410] Red dopants may include at least one of red phosphorescent materials, red fluorescent materials, and red delayed fluorescent materials. As an example, red dopant may include, but is not limited to: [bis(2-(4,6-dimethyl)phenylquinoline)](2,2,6,6-tetramethylheptane-3,5-diketoic acid)iridium(III), bis[2-(4-n-hexylphenyl)quinoline](acetylacetonate)iridium(III))(Hex-Ir(phq)2(acac)), tris[2-(4-n-hexylphenyl)quinoline]iridium(III))(Hex-Ir(phq)3), tris[2-phenyl-4-methylquinoline]iridium(III))(Ir(Mphq)3, bis(2-phenylquinoline)(2,2,6,6-tetramethylheptene-3,5-diketoic acid)iridium(III))(Ir(dpm)PQ2, bis(phenylisoquinoline)(2,2,6,6-tetramethylheptene-3,5-diketoic acid)iridium(III))(Ir(dpm)pi q)2), (bis[(4-n-hexylphenyl)isoquinoline](acetylacetonate)iridium(III))(Hex-Ir(piq)2(acac)), tri[2-(4-n-hexylphenyl)quinoline]iridium(III))(Hex-Ir(piq)3), tri(2-(3-methylphenyl)-7-methylquinoline)iridium(Ir(dmpq)3), bis[2-(2-methylphenyl)-7-methylquinoline](acetylacetonate)iridium(III))(Ir(dmpq)2(acac)), bis[2-(3,5-dimethylphenyl)-4-methylquinoline](acetylacetonate)iridium(III))(Ir(mphmq)2(acac)), tri(dibenzoylmethane)mono(1,10-phenanthroline)eupy(III))(Eu(dbm)3(phen)), and combinations thereof.

[0411] The upper EML 740B may include a dopant 742, a first host 744, and / or a second host 746. The dopant 742 is an organometallic compound of a green phosphorescent material having a structure of formulas 1 to 6. The first host 744 is a biscarbazolyl organocompound with a p-type host having a structure of formulas 7 to 8. The second host 746 is an azazine-based organocompound with an n-type host having a structure of formulas 9 to 10.

[0412] As an example, the content of the body, including the first body 744 and the second body 746, in the upper EML 740B can be, but is not limited to, between about 50 wt% and about 99 wt%, for example, between about 80 wt% and about 95 wt%, and the content of the dopant in the upper EML 740B can be, but is not limited to, between about 1 wt% and about 50 wt%, for example, between about 5 wt% and about 20 wt%. When the upper EML 740B includes the first body 744 and the second body 746, the first body 744 and the second body 746 can be mixed, but is not limited to having a weight ratio of about 4:1 to about 1:4, for example, a weight ratio of about 3:1 to about 1:3.

[0413] Alternatively, EML2 740 may further include an intermediate luminescent material layer (third layer) of a yellow-green EML disposed between the lower EML 740A of the red EML and the upper EML 740B of the green EML. Figure 6 740C (in the middle).

[0414] According to this aspect, the OLED D2 has a tandem structure. At least one EML includes a dopant 742 with beneficial light-emitting properties, and a first body 744 and / or a second body 746 with beneficial charge and energy transfer properties. By combining the dopant 742, which has a rigid chemical conformation and whose emission color can be easily tuned, with the first body 744 and / or the second body 746, which have beneficial light-emitting properties, the OLED D2 is able to reduce its driving voltage and improve its luminous efficiency and luminous lifetime.

[0415] Furthermore, the OLED D2 includes at least one HTL comprising a hole transport material 722 having advantageous hole transport properties and at least one ETL comprising an electron transport material 762 having advantageous electron transport properties, disposed adjacent to at least one EML. Therefore, holes and electrons can be rapidly injected into at least one EML.

[0416] OLEDs can have three or more light-emitting elements to form a series structure. Figure 6 This is a schematic cross-sectional view illustrating an organic light-emitting diode according to yet another exemplary embodiment of the present disclosure. Figure 6As shown, the OLED D3 includes a first electrode 510 and a second electrode 520 facing each other, and a light-emitting layer 530' disposed between the first electrode 510 and the second electrode 520. The light-emitting layer 530' includes a first light-emitting portion 600 disposed between the first electrode 510 and the second electrode 520, a second light-emitting portion 700' disposed between the first light-emitting portion 600 and the second electrode 520, a third light-emitting portion 800 disposed between the second light-emitting portion 700' and the second electrode 520, a first charge-generating layer (CGL1) 680 disposed between the first light-emitting portion 600 and the second light-emitting portion 700', and a second charge-generating layer (CGL2) 780 disposed between the second light-emitting portion 700' and the third light-emitting portion 800.

[0417] The first light-emitting portion 600 includes a first EML (EML1) 640. The first light-emitting portion 600 may further include at least one of the following: a HIL 610 disposed between the first electrode 510 and EML1 640; a first HTL (HTL1) 620 disposed between HIL 610 and EML1 640; and a first ETL (ETL1) 660 disposed between EML1 640 and CGL 680. Alternatively, the first light-emitting portion 600 may further include a first EBL (EBL1) 630 disposed between HTL1 620 and EML1 640; and / or a first HBL (HBL1) 650 disposed between EML1 640 and ETL1 660.

[0418] The second light-emitting portion 700' includes a second EML (EML2) 740'. The second light-emitting portion 700' may further include at least one of a second HTL (HTL2) 720 disposed between CGL1 680 and EML2 740', and a second ETL (ETL2) 760 disposed between the second electrode 520 and EML2 740'. Alternatively, the second light-emitting portion 700' may further include a second EBL (EBL2) 730 disposed between HTL2 720 and EML2 740', and / or a second HBL (HBL2) 750 disposed between EML2 740' and ETL2 760.

[0419] The third light-emitting part 800 includes a third EML (EML3) 840. The third light-emitting part 800 may further include at least one of a third HTL (HTL3) 820 disposed between CGL2780 and EML3 840, a third ETL (ETL3) 860 disposed between the second electrode 520 and EML3 840, and an EIL 870 disposed between the second electrode 520 and ETL3 860. Alternatively, the third light-emitting part 800 may further include a third EBL (EBL3) 830 disposed between HTL3 820 and EML3 840, and / or a third HBL (HBL3) 850 disposed between EML3 840 and ETL3 860.

[0420] At least one of EML1 640, EML2 740', and EML3 840 may include a dopant 742, a first body 744, and / or a second body 746 to emit green or yellow-green. Furthermore, another of EML1 640, EML2 740', and EML3 840 emits blue, thus OLED D3 can achieve white emission. The OLED emitting green or yellow-green from EML2 740' will be described in detail below.

[0421] In addition, at least one of HTL1 620, HTL2 720 and HTL3 820 may include hole transport material 722, and at least one of ETL1 660, ETL2 760 and ETL3 860 may include electron transport material 762.

[0422] In one exemplary embodiment, each of HTL1 620 and HTL3 820 may independently comprise a spirodifluorenyl organic compound having a structure of Formula 11 to Formula 12. Alternatively, each of HTL1 620 and HTL3820 may independently include, but is not limited to, TPD, NPB (NPD), DNTPD, CBP, Poly-TPD, TFB, TAPC, DCDPA, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl-4-amine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine and combinations thereof.

[0423] HTL2 720 includes hole transport material 722. Hole transport material 722 may include spirodifluorene-based organic compounds having a structure of formula 11 to formula 12.

[0424] Each of ETL1 660, ETL2 760, and ETL3 860 respectively promotes electron transport in each of the first light-emitting section 600, the second light-emitting section 700', and the third light-emitting section 800. As an example, each of ETL1 660 and ETL3 860 may independently comprise a benzimidazole-based organic compound having a structure of formula 13 to formula 16.

[0425] Alternatively, each of ETL1 660 and ELT3 860 may independently include, but is not limited to, at least one of oxadiazoles, triazoles, phenanthrolines, benzoxazoles, benzothiazoles, benzimidazoles, triazines, and the like.

[0426] As an example, each of ETL1 660 and ETL3 860 may independently include, but is not limited to, Alq3, BAlq, Liq, PBD, spiro-PBD, TPBi, Bphen, NBphen, BCP, TAZ, NTAZ, TpPyPB, TmPPPyTz, PFNBr, TPQ, TSPO1, ZADN, and combinations thereof.

[0427] ETL2 760 includes electron transport material 762. Electron transport material 762 may include benzimidazole-based organic compounds having structures of formulas 13 to 16.

[0428] Each of EBL1 630, EBL2 730, and EBL3 830 may independently include, but is not limited to, TCTA, tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, TAPC, MTDATA, mCP, mCBP, CuPc, DNTPD, TDAPB, DCDPA, 2,8-bis(9-phenyl-9H-carbazole-3-yl)dibenzo[b,d]thiophene, and combinations thereof.

[0429] Each of HBL1 650, HBL2 750 and HBL3 850 may independently include, but is not limited to, Alq3, BAlq, Liq, PBD, spiro-PBD, BCP, B3PYMPM, DPEPO, 9-(6-(9H-carbazole-9-yl)pyridin-3-yl)-9H-3,9'-biscarbazole, TSPO1, and combinations thereof.

[0430] CGL1 680 is disposed between the first light-emitting part 600 and the second light-emitting part 700', and CGL2 780 is disposed between the second light-emitting part 700' and the third light-emitting part 800. CGL1 680 includes a first N-type CGL (N-CGL1) 685 disposed adjacent to the first light-emitting part 600 and a first P-type CGL (P-CGL1) 690 disposed adjacent to the second light-emitting part 700'. CGL2 780 includes a second N-type CGL (N-CGL2) 785 disposed adjacent to the second light-emitting part 700' and a second P-type CGL (P-CGL2) 790 disposed adjacent to the third light-emitting part 800. Each of N-CGL1 685 and N-CGL2 785 injects electrons into EML1 640 of the first light-emitting part 600 and EML2 740' of the second light-emitting part 700', respectively, and each of P-CGL1 690 and P-CGL2 790 injects holes into EML2 740' of the second light-emitting part 700' and EML3 840 of the third light-emitting part 800, respectively.

[0431] Each of EML1 640 and EML3 840 can be independently a blue EML. In this case, each of EML1 640 and EML3 840 can be independently a blue EML, a sky-blue EML, or a dark blue EML. Each of EML1 640 and EML3 840 can independently include a blue body and a blue dopant. Each of the blue body and the blue dopant can be compared with a reference... Figure 5 The blue body and the blue dopant are identical. For example, the blue dopant may include at least one of blue phosphorescent material, blue fluorescent material, and blue delayed fluorescent material. Alternatively, the blue dopant in EML1 640 may be the same as or different from the blue dopant in EML3 840 in terms of color and / or luminous efficiency.

[0432] EML2 740' may include a lower EML (first layer) 740A disposed between EBL2 730 and HBL2 750, an upper EML (second layer) 740B disposed between the lower EML 740A and HBL2 750, and optionally, an intermediate EML (third layer) 740C disposed between the lower EML 740A and the upper EML 740B. One of the lower EML 740A and the upper EML 740B may emit red and the other of the lower EML 740A and the upper EML 740B may emit green. EML2 740', in which the lower EML 740A emits red and the upper EML 740B emits green, will be described in detail below.

[0433] The lower EML 740A may include a red body and a red dopant. Each of the red body and the red dopant may be used with a reference. Figure 5 The red host and the red dopant are identical. For example, the red dopant may include at least one of red phosphorescent material, red fluorescent material, and red delayed fluorescent material.

[0434] The upper EML 740B may include a dopant 742, a first host 744, and / or a second host 746. The dopant 742 is an organometallic compound of a green phosphorescent material having a structure of formulas 1 to 6. The first host 744 is a biscarbazolyl compound with a p-type host having a structure of formulas 7 to 8. The second host 746 is an azazine-based organocompound with an n-type host having a structure of formulas 9 to 10.

[0435] As an example, the content of the body, including the first body 744 and the second body 746, in the upper EML 740B can be, but is not limited to, between about 50 wt% and about 99 wt%, for example, between about 80 wt% and about 95 wt%, and the content of the dopant in the upper EML 740B can be, but is not limited to, between about 1 wt% and about 50 wt%, for example, between about 5 wt% and about 20 wt%. When the upper EML 740B includes the first body 744 and the second body 746, the first body 744 and the second body 746 can be mixed, but is not limited to having a weight ratio of about 4:1 to about 1:4, for example, a weight ratio of about 3:1 to about 1:3.

[0436] The intermediate EML 740C can be a yellow-green EML and may include a yellow-green body and a yellow-green dopant. As an example, the yellow-green body can be the same as a red body. The yellow-green dopant may include at least one of a yellow-green phosphorescent material, a yellow-green fluorescent material, and a yellow-green delayed fluorescent material. The intermediate EML 740C may be omitted.

[0437] In OLED D3, at least one EML includes a dopant 742 with beneficial light-emitting properties, a first host 744, and / or a second host 746. The dopant 742 is capable of maintaining its stable chemical conformation during light emission. OLED D3 including the dopant 742 with beneficial light-emitting properties, as well as the first host 744 and / or the second host 746, can achieve white light emission with improved luminous efficiency and lifetime.

[0438] Furthermore, the OLED D4 includes at least one HTL comprising a hole transport material 722 having advantageous hole transport properties and at least one ETL comprising an electron transport material 762 having advantageous electron transport properties, disposed adjacent to at least one EML. Therefore, holes and electrons can be rapidly injected into at least one EML.

[0439] Synthesis Example 1: Synthesis of Compound 1

[0440] (1) Synthesis of intermediate A-1

[0441] [Reaction 1-1]

[0442]

[0443] Under a nitrogen atmosphere, compounds SM-1 (7.34 g, 20 mmol), SM-2 (2.27 g, 20 mmol), tetrakis(triphenylphosphine)palladium(O) (Pd(PPh3)4, 1.2 g, 1 mmol), K2CO3 (8.3 g, 60 mmol), and a mixed solvent of toluene (200 mL) and water (50 mL) were added to a 500 mL round-bottom flask. The solution was then heated and refluxed with stirring for 12 hours. The organic layer was extracted with chloroform and washed with water. Water was removed with anhydrous MgSO4, the dried organic layer was filtered, and the organic solvent was removed under reduced pressure. The crude product was then purified by column chromatography to give intermediate A-1 (6.05 g, yield: 95%).

[0444] (2) Synthesis of intermediate I-1

[0445] [Reaction 1-2]

[0446]

[0447] Compound SM-3 (3.10 g, 20 mmol), IrCl3 (2.39 g, 8.0 mmol), and a mixed solvent of ethoxyethanol (90 mL) and water (30 mL) were added to a 250 mL round-bottom flask. The solution was then stirred at 130 °C for 16 hours. After the reaction was complete, the solution was cooled to room temperature, and methanol was added to facilitate filtration of the solid produced under reduced pressure to give intermediate I-1 (9.56 g, yield: 89%) in solid form.

[0448] (3) Synthesis of intermediate I-2

[0449] [Reaction Formula 1-3]

[0450]

[0451] Intermediate I-1 (5.16 g, 4.8 mmol), silver trifluoromethanesulfonate (AgOTf, 3.6 g, 14.3 mmol), and dichloromethane were added to a 1000 mL round-bottom flask. The solution was then stirred at room temperature for 16 hours. After the reaction was complete, the solution was filtered through diatomaceous earth to remove the solid. The solvent was removed by vacuum distillation to give intermediate I-2 (6.03 g, yield: 88%) in solid form.

[0452] (4) Synthesis of Compound 1

[0453] [Reaction Equations 1-4]

[0454]

[0455] Under a nitrogen atmosphere, intermediates A-1 (1.11 g, 3.5 mmol), I-2 (2.15 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask. The solution was then stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 1 (2.01 g, yield: 82%).

[0456] Synthesis Example 2: Synthesis of Compound 2

[0457] (1) Synthesis of intermediate B-1

[0458] [Reaction 2-1]

[0459]

[0460] Under a nitrogen atmosphere, compounds SM-1 (7.34 g, 20 mmol), SM-4 (2.54 g, 20 mmol), Pd(PPh3)4 (1.2 g, 1 mmol), K2CO3 (8.3 g, 60 mmol), and a mixed solvent of toluene (200 mL) and water (50 mL) were added to a 500 mL round-bottom flask. The solution was then heated and refluxed with stirring for 12 hours. The organic layer was extracted with chloroform and washed with water. Water was removed with anhydrous MgSO4, the dried organic layer was filtered, and the organic solvent was removed under reduced pressure. The crude product was then purified by column chromatography to give intermediate B-1 (6.17 g, yield: 93%).

[0461] (2) Synthesis of compound 2

[0462] [Reaction 2-2]

[0463]

[0464] Under a nitrogen atmosphere, intermediate B-1 (1.16 g, 3.5 mmol), intermediate I-2 (2.15 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask, and the solution was stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 2 (2.02 g, yield: 81%).

[0465] Synthesis Example 3: Synthesis of Compound 16

[0466] (1) Synthesis of intermediate C-1

[0467] [Reaction 3-1]

[0468]

[0469] Under a nitrogen atmosphere, compounds SM-5 (7.34 g, 20 mmol), SM-2 (2.27 g, 20 mmol), Pd(PPh3)4 (1.2 g, 1 mmol), K2CO3 (8.3 g, 60 mmol), and a mixed solvent of toluene (200 mL) and water (50 mL) were added to a 500 mL round-bottom flask. The solution was then heated and refluxed with stirring for 12 hours. The organic layer was extracted with chloroform and washed with water. Water was removed with anhydrous MgSO4, the dried organic layer was filtered, and the organic solvent was removed under reduced pressure. The crude product was then purified by column chromatography to give intermediate C-1 (5.66 g, yield: 93%).

[0470] (2) Synthesis of compound 16

[0471] [Reaction 3-2]

[0472]

[0473] Under a nitrogen atmosphere, intermediate C-1 (1.12 g, 3.5 mmol), intermediate I-2 (2.15 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask. The solution was then stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 16 (2.02 g, yield: 81%).

[0474] Synthesis Example 4: Synthesis of Compound 17

[0475] (1) Synthesis of intermediate D-1

[0476] [Reaction 4-1]

[0477]

[0478] Under a nitrogen atmosphere, compounds SM-5 (7.34 g, 20 mmol), SM-4 (2.54 g, 20 mmol), Pd(PPh3)4 (1.2 g, 1 mmol), K2CO3 (8.3 g, 60 mmol), and a mixed solvent of toluene (200 mL) and water (50 mL) were added to a 500 mL round-bottom flask. The solution was then heated and refluxed with stirring for 12 hours. The organic layer was extracted with chloroform and washed with water. Water was removed with anhydrous MgSO4, the dried organic layer was filtered off, and the organic solvent was removed under reduced pressure. The crude product was then purified by column chromatography to give intermediate D-1 (5.86 g, yield: 88%).

[0479] (2) Synthesis of compound 17

[0480] [Reaction 4-2]

[0481]

[0482] Under a nitrogen atmosphere, intermediates D-1 (1.17 g, 3.5 mmol), I-2 (2.15 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask. The solution was then stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 17 (2.25 g, yield: 90%).

[0483] Synthesis Example 5: Synthesis of Compound 27

[0484] (1) Synthesis of intermediate E-1

[0485] [Reaction Formula 5-1]

[0486]

[0487] Under a nitrogen atmosphere, compounds SM-1 (7.34 g, 20 mmol), SM-6 (4.08 g, 20 mmol), Pd(PPh3)4 (1.2 g, 1 mmol), K2CO3 (8.3 g, 60 mmol), and a mixed solvent of toluene (200 mL) and water (50 mL) were added to a 500 mL round-bottom flask. The solution was then heated and refluxed with stirring for 12 hours. The organic layer was extracted with chloroform and washed with water. Water was removed with anhydrous MgSO4, the dried organic layer was filtered, and the organic solvent was removed under reduced pressure. The crude product was then purified by column chromatography to give intermediate E-1 (7.34 g, yield: 90%).

[0488] (2) Synthesis of compound 27

[0489] [Reaction 5-2]

[0490]

[0491] Under a nitrogen atmosphere, intermediates E-1 (1.43 g, 3.5 mmol), I-2 (2.15 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask. The solution was then stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 27 (2.45 g, yield: 90%).

[0492] Synthesis Example 6: Synthesis of Compound 32

[0493] (1) Synthesis of intermediate F-1

[0494] [Reaction 6-1]

[0495]

[0496] Under a nitrogen atmosphere, compounds SM-1 (7.34 g, 20 mmol), SM-7 (4.24 g, 20 mmol), Pd(PPh3)4 (1.2 g, 1 mmol), K2CO3 (8.3 g, 60 mmol), and a mixed solvent of toluene (200 mL) and water (50 mL) were added to a 500 mL round-bottom flask. The solution was then heated and refluxed with stirring for 12 hours. The organic layer was extracted with chloroform and washed with water. Water was removed with anhydrous MgSO4, the dried organic layer was filtered, and the organic solvent was removed under reduced pressure. The crude product was then purified by column chromatography to give intermediate F-1 (7.67 g, yield: 92%).

[0497] (2) Synthesis of intermediate J-1

[0498] [Reaction 6-2]

[0499]

[0500] Compound SM-8 (3.38 g, 20 mmol), IrCl3 (2.39 g, 8.0 mmol), and a mixed solvent of ethoxyethanol (90 mL) and water (30 mL) were added to a 250 mL round-bottom flask. The solution was then stirred at 130 °C for 16 hours. After the reaction was complete, the solution was cooled to room temperature, and methanol was added to facilitate filtration of the solid produced under reduced pressure to give intermediate J-1 (4.07 g, yield: 90%) in solid form.

[0501] (3) Synthesis of intermediate J-2

[0502] [Reaction 6-3]

[0503]

[0504] Intermediate J-1 (5.16 g, 4.8 mmol), silver trifluoromethanesulfonate (AgOTf, 3.6 g, 14.3 mmol), and dichloromethane were added to a 1000 mL round-bottom flask. The solution was then stirred at room temperature for 16 hours. After the reaction was complete, the solution was filtered through diatomaceous earth to remove the solid. The solvent was removed by vacuum distillation to give intermediate J-2 (6.03 g, yield: 88%) in solid form.

[0505] (4) Synthesis of compound 32

[0506] [Reaction 6-4]

[0507]

[0508] Under a nitrogen atmosphere, intermediates F-1 (1.46 g, 3.5 mmol), J-2 (2.23 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask. The solution was then stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 32 (2.47 g, yield: 87%).

[0509] Synthesis Example 7: Synthesis of Compound 34

[0510] (1) Synthesis of intermediate G-1

[0511] [Reaction Formula 7-1]

[0512]

[0513] Under a nitrogen atmosphere, compounds SM-1 (7.34 g, 20 mmol), SM-9 (4.24 g, 20 mmol), Pd(PPh3)4 (1.2 g, 1 mmol), K2CO3 (8.3 g, 60 mmol), and a mixed solvent of toluene (200 mL) and water (50 mL) were added to a 500 mL round-bottom flask. The solution was then heated and refluxed with stirring for 12 hours. The organic layer was extracted with chloroform and washed with water. Water was removed with anhydrous MgSO4, the dried organic layer was filtered, and the organic solvent was removed under reduced pressure. The crude product was then purified by column chromatography to give intermediate G-1 (7.53 g, yield: 91%).

[0514] (2) Synthesis of compound 34

[0515] [Reaction 7-2]

[0516]

[0517] Under a nitrogen atmosphere, intermediates G-1 (1.45 g, 3.5 mmol), J-2 (2.23 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask. The solution was then stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 34 (2.26 g, yield: 80%).

[0518] Synthesis Example 8: Synthesis of Compound 35

[0519] (1) Synthesis of intermediate H-1

[0520] [Reaction Equation 8-1]

[0521]

[0522] Under a nitrogen atmosphere, compounds SM-1 (7.34 g, 20 mmol), SM-10 (4.14 g, 20 mmol), Pd(PPh3)4 (1.2 g, 1 mmol), K2CO3 (8.3 g, 60 mmol), and a mixed solvent of toluene (200 mL) and water (50 mL) were added to a 500 mL round-bottom flask. The solution was then heated and refluxed with stirring for 12 hours. The organic layer was extracted with chloroform and washed with water. Water was removed with anhydrous MgSO4, the dried organic layer was filtered, and the organic solvent was removed under reduced pressure. The crude product was then purified by column chromatography to give intermediate H-1 (7.83 g, yield: 95%).

[0523] (2) Synthesis of compound 35

[0524] [Reaction Equation 8-2]

[0525]

[0526] Under a nitrogen atmosphere, intermediates H-1 (1.44 g, 3.5 mmol), J-2 (2.23 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask. The solution was then stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 35 (2.28 g, yield: 81%).

[0527] Synthesis Example 9: Synthesis of Compound 136

[0528] (1) Synthesis of intermediate A-2

[0529] [Reaction 9-1]

[0530]

[0531] Intermediate A-1 (6.36 g, 20 mmol), IrCl3 (2.39 g, 8.0 mmol), and a mixed solvent of ethoxyethanol (90 mL) and water (30 mL) were added to a 250 mL round-bottom flask. The solution was then stirred at 130 °C for 16 hours. After the reaction was complete, the solution was cooled to room temperature, and methanol was added to facilitate filtration of the solid produced under reduced pressure to give intermediate A-2 (5.53 g, yield: 80%) in solid form.

[0532] (2) Synthesis of intermediate A-3

[0533] [Reaction 9-2]

[0534]

[0535] Intermediate A-2 (8.29 g, 4.8 mmol), silver trifluoromethanesulfonate (AgOTf, 3.6 g, 14.3 mmol), and dichloromethane were added to a 1000 mL round-bottom flask. The solution was then stirred at room temperature for 16 hours. After the reaction was complete, the solution was filtered through diatomaceous earth to remove the solid. The solvent was removed by vacuum distillation to give intermediate A-3 (7.99 g, yield: 80%) in solid form.

[0536] (3) Synthesis of compound 136

[0537] [Reaction 9-3]

[0538]

[0539] Under a nitrogen atmosphere, compound L-1 (0.54 g, 3.5 mmol), intermediate A-3 (3.12 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask. The solution was then stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 136 (2.46 g, yield: 80%).

[0540] Synthesis Example 10: Synthesis of Compound 137

[0541] [Reaction Formula 10]

[0542]

[0543] Under a nitrogen atmosphere, compound L-2 (0.35 g, 3.5 mmol), intermediate A-3 (3.12 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask. The solution was then stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 137 (2.22 g, yield: 80%).

[0544] Synthesis Example 11: Synthesis of Compound 141

[0545] (1) Synthesis of intermediate C-2

[0546] [Reaction Formula 11-1]

[0547]

[0548] Intermediate C-1 (6.36 g, 20 mmol), IrCl3 (2.39 g, 8.0 mmol), and a mixed solvent of ethoxyethanol (90 mL) and water (30 mL) were added to a 250 mL round-bottom flask. The solution was then stirred at 130 °C for 16 hours. After the reaction was complete, the solution was cooled to room temperature, and methanol was added to facilitate filtration of the solid produced under reduced pressure to give intermediate C-2 (5.32 g, yield: 77%) in solid form.

[0549] (2) Synthesis of intermediate C-3

[0550] [Reaction 11-2]

[0551]

[0552] Intermediate C-2 (8.29 g, 4.8 mmol), silver trifluoromethanesulfonate (AgOTf, 3.6 g, 14.3 mmol), and dichloromethane were added to a 1000 mL round-bottom flask. The solution was then stirred at room temperature for 16 hours. After the reaction was complete, the solution was filtered through diatomaceous earth to remove the solid. The solvent was removed by vacuum distillation to give intermediate C-3 (7.29 g, yield: 72%) in solid form.

[0553] (3) Synthesis of compound 141

[0554] [Reaction 11-3]

[0555]

[0556] Under a nitrogen atmosphere, compound L-1 (0.54 g, 3.5 mmol), intermediate C-3 (3.13 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask. The solution was then stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 141 (2.45 g, yield: 83%).

[0557] Synthesis Example 12: Synthesis of Compound 142

[0558] (1) Synthesis of intermediate D-2

[0559] [Reaction 12-1]

[0560]

[0561] Intermediate D-1 (6.64 g, 20 mmol), IrCl3 (2.39 g, 8.0 mmol), and a mixed solvent of ethoxyethanol (90 mL) and water (30 mL) were added to a 250 mL round-bottom flask. The solution was then stirred at 130 °C for 16 hours. After the reaction was complete, the solution was cooled to room temperature, and methanol was added to facilitate filtration of the solid produced under reduced pressure to give intermediate D-2 (5.71 g, yield: 80%) in solid form.

[0562] (2) Synthesis of intermediate D-3

[0563] [Reaction 12-2]

[0564]

[0565] Intermediate D-2 (8.58 g, 4.8 mmol), silver trifluoromethanesulfonate (AgOTf, 3.6 g, 14.3 mmol), and dichloromethane were added to a 1000 mL round-bottom flask. The solution was then stirred at room temperature for 16 hours. After the reaction was complete, the solution was filtered through diatomaceous earth to remove the solid. The solvent was removed by vacuum distillation to give intermediate D-3 (7.09 g, yield: 69%) in solid form.

[0566] (3) Synthesis of compound 142

[0567] [Reaction 12-3]

[0568]

[0569] Under a nitrogen atmosphere, compound L-2 (0.35 g, 3.5 mmol), intermediate D-3 (3.21 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask. The solution was then stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 142 (2.12 g, yield: 74%).

[0570] Synthesis Example 13: Synthesis of Compound 147

[0571] (1) Synthesis of intermediate E-2

[0572] [Reaction Formula 13-1]

[0573]

[0574] Intermediate E-1 (8.16 g, 20 mmol), IrCl3 (2.39 g, 8.0 mmol), and a mixed solvent of ethoxyethanol (90 mL) and water (30 mL) were added to a 250 mL round-bottom flask. The solution was then stirred at 130 °C for 16 hours. After the reaction was complete, the solution was cooled to room temperature, and methanol was added to facilitate filtration of the solid produced under reduced pressure to give intermediate E-2 (7.26 g, yield: 87%) in solid form.

[0575] (2) Synthesis of intermediate E-3

[0576] [Reaction 13-2]

[0577]

[0578] Intermediate E-2 (10.0 g, 4.8 mmol), silver trifluoromethanesulfonate (AgOTf, 3.6 g, 14.3 mmol), and dichloromethane were added to a 1000 mL round-bottom flask. The solution was then stirred at room temperature for 16 hours. After the reaction was complete, the solution was filtered through diatomaceous earth to remove the solid. The solvent was removed by vacuum distillation to give intermediate E-3 (8.91 g, yield: 76%) in solid form.

[0579] (3) Synthesis of compound 147

[0580] [Reaction 13-3]

[0581]

[0582] Under a nitrogen atmosphere, compound L-2 (0.35 g, 3.5 mmol), intermediate E-3 (3.36 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask. The solution was then stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 147 (2.59 g, yield: 78%).

[0583] Synthesis Example 14: Synthesis of Compound 148

[0584] [Reaction Formula 14]

[0585]

[0586] Under a nitrogen atmosphere, compound L-1 (0.54 g, 3.5 mmol), intermediate E-3 (3.36 g, 3.0 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 100 mL round-bottom flask. The solution was then stirred at 130 °C for 48 hours. After the reaction was complete, the organic layer was extracted with dichloromethane and washed with distilled water, and the solvent was removed by vacuum distillation. The crude product was purified by column chromatography (eluent: toluene and hexane) to give compound 148 (2.96 g, yield: 85%).

[0587] Synthesis Example 15: Synthesis of Compound 251

[0588] [Reaction Formula 15]

[0589]

[0590] Under a nitrogen atmosphere, intermediate J-2 (2.23 g, 3.0 mmol), intermediate A-1 (1.11 g, 3.5 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 150 mL round-bottom flask. The solution was then stirred at 135 °C for 18 hours. After the reaction was complete, the solution was cooled to room temperature, the organic layer was extracted with dichloromethane and washed with distilled water, and the water was removed with anhydrous magnesium sulfate. The filtrate was treated under reduced pressure to obtain the crude product. The crude product was then purified by column chromatography (eluent: vinyl acetate:hexane, v / v ratio 25:75) to give compound 251 (2.31 g, yield: 91%).

[0591] Synthesis Example 16: Synthesis of Compound 252

[0592] [Reaction Formula 16]

[0593]

[0594] Under a nitrogen atmosphere, intermediates J-2 (2.23 g, 3.0 mmol), E-1 (1.43 g, 3.5 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 150 mL round-bottom flask. The solution was then stirred at 135 °C for 18 hours. After the reaction was complete, the solution was cooled to room temperature, the organic layer was extracted with dichloromethane and washed with distilled water, and the water was removed with anhydrous magnesium sulfate. The filtrate was treated under reduced pressure to obtain the crude product. The crude product was then purified by column chromatography (eluent: vinyl acetate:hexane, v / v ratio 25:75) to give compound 252 (2.61 g, yield: 93%).

[0595] Synthesis Example 17: Synthesis of Compound 253

[0596] (1) Synthesis of intermediate K-1

[0597] [Reaction Formula 17-1]

[0598]

[0599] Under a nitrogen atmosphere, compounds SM-1 (7.34 g, 20 mmol), SM-11 (3.79 g, 20 mmol), Pd(PPh3)4 (1.2 g, 1 mmol), K2CO3 (8.3 g, 60 mmol), and a mixed solvent of toluene (200 mL) and water (50 mL) were added to a 500 mL round-bottom flask. The solution was then heated and refluxed with stirring for 12 hours. After the reaction was complete, the solution was cooled to room temperature, the organic layer was extracted with dichloromethane, and washed with excess water. The water was removed with anhydrous magnesium sulfate, the dried organic layer was filtered, and the filtrate was concentrated under reduced pressure. The concentrate was purified by column chromatography to give intermediate K-1 (7.26 g, 92% yield).

[0600] (2) Synthesis of compound 253

[0601] [Reaction 17-2]

[0602]

[0603] Under a nitrogen atmosphere, intermediates J-2 (2.23 g, 3.0 mmol), K-1 (1.38 g, 3.5 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 150 mL round-bottom flask. The solution was then stirred at 135 °C for 18 hours. After the reaction was complete, the solution was cooled to room temperature, the organic layer was extracted with dichloromethane and washed with distilled water, and the water was removed with anhydrous magnesium sulfate. The filtrate was treated under reduced pressure to obtain the crude product. The crude product was then purified by column chromatography (eluent: vinyl acetate:hexane, v / v ratio 25:75) to give compound 253 (2.55 g, yield: 92%).

[0604] Synthesis Example 18: Synthesis of Compound 254

[0605] (1) Synthesis of intermediate M-1

[0606] [Reaction Formula 18-1]

[0607]

[0608] Under a nitrogen atmosphere, compounds SM-1 (7.34 g, 20 mmol), SM-12 (4.26 g, 20 mmol), Pd(PPh3)4 (1.2 g, 1 mmol), K2CO3 (8.3 g, 60 mmol), and a mixed solvent of toluene (200 mL) and water (50 mL) were added to a 500 mL round-bottom flask. The solution was then heated and refluxed with stirring for 12 hours. After the reaction was complete, the solution was cooled to room temperature, the organic layer was extracted with dichloromethane, and washed with excess water. The water was removed with anhydrous magnesium sulfate, the dried organic layer was filtered, and the filtrate was concentrated under reduced pressure. The concentrate was purified by column chromatography to give intermediate M-1 (7.04 g, 94% yield).

[0609] (2) Synthesis of compound 254

[0610] [Reaction 18-2]

[0611]

[0612] Under a nitrogen atmosphere, intermediates J-2 (2.23 g, 3.0 mmol), M-1 (1.43 g, 3.5 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 150 mL round-bottom flask. The solution was then stirred at 135 °C for 18 hours. After the reaction was complete, the solution was cooled to room temperature, the organic layer was extracted with dichloromethane and washed with distilled water, and the water was removed with anhydrous magnesium sulfate. The filtrate was treated under reduced pressure to obtain the crude product. The crude product was then purified by column chromatography (eluent: vinyl acetate:hexane, v / v ratio 25:75) to give compound 254 (2.55 g, yield: 89%).

[0613] Synthesis Example 19: Synthesis of Compound 255

[0614] (1) Synthesis of intermediate N-1

[0615] [Reaction Formula 19-1]

[0616]

[0617] Under a nitrogen atmosphere, compounds SM-13 (8.47 g, 20 mmol), SM-11 (3.79 g, 20 mmol), Pd(PPh3)4 (1.2 g, 1 mmol), K2CO3 (8.3 g, 60 mmol), and a mixed solvent of toluene (200 mL) and water (50 mL) were added to a 500 mL round-bottom flask. The solution was then heated and refluxed with stirring for 12 hours. After the reaction was complete, the solution was cooled to room temperature, the organic layer was extracted with dichloromethane, and washed with excess water. The water was removed with anhydrous magnesium sulfate, the dried organic layer was filtered, and the filtrate was concentrated under reduced pressure. The concentrate was purified by column chromatography to give intermediate N-1 (8.11 g, 90% yield).

[0618] (2) Synthesis of compound 255

[0619] [Reaction 19-2]

[0620]

[0621] Under a nitrogen atmosphere, intermediates J-2 (2.23 g, 3.0 mmol), N-1 (1.58 g, 3.5 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 150 mL round-bottom flask. The solution was then stirred at 135 °C for 18 hours. After the reaction was complete, the solution was cooled to room temperature, the organic layer was extracted with dichloromethane and washed with distilled water, and the water was removed with anhydrous magnesium sulfate. The filtrate was treated under reduced pressure to obtain the crude product. The crude product was then purified by column chromatography (eluent: vinyl acetate:hexane, v / v ratio 25:75) to give compound 255 (2.55 g, yield: 87%).

[0622] Synthesis Example 20: Synthesis of Compound 256

[0623] (1) Synthesis of intermediate O-1

[0624] [Reaction Formula 20-1]

[0625]

[0626] Under a nitrogen atmosphere, compounds SM-13 (8.47 g, 20 mmol), SM-14 (3.79 g, 20 mmol), Pd(PPh3)4 (1.2 g, 1 mmol), K2CO3 (8.3 g, 60 mmol), and a mixed solvent of toluene (200 mL) and water (50 mL) were added to a 500 mL round-bottom flask. The solution was then heated and refluxed with stirring for 12 hours. After the reaction was complete, the solution was cooled to room temperature, the organic layer was extracted with dichloromethane, and washed with excess water. The water was removed with anhydrous magnesium sulfate, the dried organic layer was filtered, and the filtrate was concentrated under reduced pressure. The concentrate was purified by column chromatography to give intermediate O-1 (8.20 g, 91% yield).

[0627] (2) Synthesis of compound 256

[0628] [Reaction 20-2]

[0629]

[0630] Under a nitrogen atmosphere, intermediates J-2 (2.23 g, 3.0 mmol), K-1 (1.38 g, 3.5 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 150 mL round-bottom flask. The solution was then stirred at 135 °C for 18 hours. After the reaction was complete, the solution was cooled to room temperature, the organic layer was extracted with dichloromethane and washed with distilled water, and the water was removed with anhydrous magnesium sulfate. The filtrate was treated under reduced pressure to obtain the crude product. The crude product was then purified by column chromatography (eluent: vinyl acetate:hexane, v / v ratio 25:75) to give compound 256 (2.55 g, yield: 92%).

[0631] Synthesis Example 21: Synthesis of Compound 257

[0632] (1) Synthesis of intermediate P-1

[0633] [Reaction 21-1]

[0634]

[0635] Under a nitrogen atmosphere, compounds SM-15 (9.47 g, 20 mmol), SM-14 (3.79 g, 20 mmol), Pd(PPh3)4 (1.2 g, 1 mmol), K2CO3 (8.3 g, 60 mmol), and a mixed solvent of toluene (200 mL) and water (50 mL) were added to a 500 mL round-bottom flask. The solution was then heated and refluxed with stirring for 12 hours. After the reaction was complete, the solution was cooled to room temperature, the organic layer was extracted with dichloromethane, and washed with excess water. The water was removed with anhydrous magnesium sulfate, the dried organic layer was filtered, and the filtrate was concentrated under reduced pressure. The concentrate was then purified by column chromatography to give intermediate P-1 (7.84 g, 87% yield).

[0636] (2) Synthesis of compound 257

[0637] [Reaction 21-2]

[0638]

[0639] Under a nitrogen atmosphere, intermediates J-2 (2.23 g, 3.0 mmol), P-1 (1.58 g, 3.5 mmol), and a mixed solvent of 2-ethoxyethanol (40 mL) and DMF (40 mL) were added to a 150 mL round-bottom flask. The solution was then stirred at 135 °C for 18 hours. After the reaction was complete, the solution was cooled to room temperature, the organic layer was extracted with dichloromethane and washed with distilled water, and the water was removed with anhydrous magnesium sulfate. The filtrate was treated under reduced pressure to obtain the crude product. The crude product was then purified by column chromatography (eluent: vinyl acetate:hexane, v / v ratio 25:75) to give compound 257 (2.67 g, yield: 91%).

[0640] Example 1 (Ex.1) Manufacturing of OLED

[0641] Organic light-emitting diodes (OLEDs) were fabricated by using GHH4 of Formula 8 as the first host, GEH2 of Formula 10 as the second host, compound 251 from Synthesis Example 15 as a dopant in the light-emitting material layer (EML), HTL1 of Formula 12 in the hole transport layer (HTL), and ETL1 of Formula 16 in the electron transport layer (ETL). A glass substrate coated with an ITO (100 nm) film was washed and ultrasonically cleaned with solvents such as isopropanol and acetone, and then dried in an oven at 100°C. The substrate was transferred to a vacuum chamber to deposit the light-emitting layer. Subsequently, an atmosphere of approximately 5-7 × 10⁻⁶ was formed. -7 Under Tor conditions, a light-emitting layer and a cathode are deposited by evaporation from a heated boat, with the deposition rate set to [value missing]. The order is as follows:

[0642] Hole injection layer (HIL) (hereinafter HI-1 (NPNPB), 100 nm thick); hole transport layer (HTL) (HTL1, 350 nm thick); EML (body (first body: second body = 7:3 weight ratio, 90 wt%), dopant (compound 251, 10 wt%), 30 nm); ETL (ETL1, 350 nm thick); EIL (Liq, 200 nm thick); and cathode (Al, 100 nm thick). The HIL material (HI-1) and the EIL material (Liq) are shown below:

[0643]

[0644] Example 2-10: OLED Manufacturing

[0645] The OLED is manufactured using the same procedures and materials as in Example 1, except that ETL2 (about Ex.2), ETL3 (about Ex.3), ETL4 (about Ex.4), ETL5 (about Ex.5), ETL6 (about Ex.6), ETL7 (about Ex.7), ETL8 (about Ex.8), ETL9 (about Ex.9), and ETL10 (about Ex.10) of Formula 16 are used instead of ETL1.

[0646] Comparative Example 1 (Ref. 1): OLED Manufacturing

[0647] The OLED was manufactured using the same procedure and materials as in Example 1, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0648] Comparative Example 2 (Ref. 2): OLED Manufacturing

[0649] The OLED was manufactured using the same procedure and materials as in Example 1, except that HT-1 was used in the HTL instead of HTL1, and ET-2 was used in the ETL instead of ETL1.

[0650] Comparative Example 3 (Ref. 3): OLED Manufacturing

[0651] The OLED was manufactured using the same procedure and materials as in Example 1, except that HT-2 was used in the HTL instead of HTL1, and ET-1 was used in the ETL instead of ETL1.

[0652] Comparative Example 4 (Ref. 4): OLED Manufacturing

[0653] The OLED was manufactured using the same procedure and materials as in Example 1, except that HT-2 was used in the HTL instead of HTL1, and ET-2 was used in the ETL instead of ETL1.

[0654] [Reference Compound]

[0655]

[0656] Experimental Example 1: Measurement of the luminescent properties of OLED

[0657] The 9mm-sized samples manufactured in Examples 1 to 10 and Comparative Examples 1 to 4 2 Each OLED with a light-emitting area was connected to an external power supply, and the luminescent characteristics of all OLEDs were evaluated at room temperature using a constant current source (KEITHLEY) and a PR650 photometer. Specifically, at a current density of 10 mA / cm²... 2 The driving voltage (V), external quantum efficiency (EQE, relative value), and the time period during which the brightness decreased from the initial brightness to 95% (LT95, relative value) were measured. The measurement results are shown in Table 1 below.

[0658] Table 1: Luminescent properties of OLEDs

[0659]

[0660]

[0661] As shown in Table 1, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0662] Example 11: OLED Manufacturing

[0663] The OLED was manufactured using the same procedure and materials as in Example 1, except that HTL2 of Formula 12 was used in the HTL instead of HTL1.

[0664] Examples 12-20: OLED Manufacturing

[0665] The OLED is manufactured using the same procedures and materials as in Example 11, except that ETL2 (about Ex. 12), ETL3 (about Ex. 13), ETL4 (about Ex. 14), ETL5 (about Ex. 15), ETL6 (about Ex. 16), ETL7 (about Ex. 17), ETL8 (about Ex. 18), ETL9 (about Ex. 19), and ETL10 (about Ex. 20) of Formula 16 are used instead of ETL1.

[0666] Experimental Example 2: Measurement of the luminescent properties of OLED

[0667] The optical properties of each OLED manufactured in Examples 11 to 20 were measured using the same procedure as in Example 1. The measurement results are shown in Table 2 below.

[0668] Table 2: Luminescent properties of OLEDs

[0669]

[0670]

[0671] As shown in Table 2, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0672] Example 21: OLED Manufacturing

[0673] The OLED was manufactured using the same procedure and materials as in Example 1, except that HTL3 of Formula 12 was used in the HTL instead of HTL1.

[0674] Examples 22-30: OLED Manufacturing

[0675] The OLED is manufactured using the same procedures and materials as in Example 21, except that ETL2 (about Ex. 22), ETL3 (about Ex. 23), ETL4 (about Ex. 24), ETL5 (about Ex. 25), ETL6 (about Ex. 26), ETL7 (about Ex. 27), ETL8 (about Ex. 28), ETL9 (about Ex. 29), and ETL10 (about Ex. 30) of Formula 16 are used instead of ETL1.

[0676] Experimental Example 3: Measurement of the luminescent properties of OLED

[0677] The optical properties of each OLED manufactured in Examples 21 to 30 were measured using the same procedure as in Example 1. The measurement results are shown in Table 3 below.

[0678] Table 3: Luminescent properties of OLEDs

[0679]

[0680]

[0681] As shown in Table 3, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0682] Example 31: OLED Manufacturing

[0683] The OLED was manufactured using the same procedure and materials as in Example 1, except that HTL4 of Formula 12 was used in the HTL instead of HTL1.

[0684] Examples 32-40: OLED Manufacturing

[0685] The OLED is manufactured using the same procedures and materials as in Example 31, except that ETL2 (about Ex. 32), ETL3 (about Ex. 33), ETL4 (about Ex. 34), ETL5 (about Ex. 35), ETL6 (about Ex. 36), ETL7 (about Ex. 37), ETL8 (about Ex. 38), ETL9 (about Ex. 39), and ETL10 (about Ex. 40) of Formula 16 are used instead of ETL1.

[0686] Experimental Example 4: Measurement of the luminescent properties of OLED

[0687] The optical properties of each OLED manufactured in Examples 31 to 40 were measured using the same procedure as in Example 1. The measurement results are shown in Table 4 below.

[0688] Table 4: Luminescent properties of OLEDs

[0689]

[0690]

[0691] As shown in Table 4, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0692] Example 41: Manufacturing of OLEDs

[0693] The OLED was manufactured using the same procedure and materials as in Example 1, except that HTL5 of Formula 12 was used in the HTL instead of HTL1.

[0694] Examples 42-50: OLED Manufacturing

[0695] The OLED is manufactured using the same procedure and materials as in Example 41, except that ETL2 (about Ex. 42), ETL3 (about Ex. 43), ETL4 (about Ex. 44), ETL5 (about Ex. 45), ETL6 (about Ex. 46), ETL7 (about Ex. 47), ETL8 (about Ex. 48), ETL9 (about Ex. 49), and ETL10 (about Ex. 50) of Formula 16 are used instead of ETL1.

[0696] Experimental Example 5: Measurement of the luminescent properties of OLED

[0697] The optical properties of each OLED manufactured in Examples 41 to 50 were measured using the same procedure as in Example 1. The measurement results are shown in Table 5 below.

[0698] Table 5: Luminescent properties of OLEDs

[0699]

[0700]

[0701] As shown in Table 5, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0702] Example 51: Manufacturing of OLEDs

[0703] The OLED was manufactured using the same procedure and materials as in Example 1, except that HTL6 of Formula 12 was used in the HTL instead of HTL1.

[0704] Examples 52-60: OLED Manufacturing

[0705] The OLED is manufactured using the same procedure and materials as in Example 51, except that ETL2 (about Ex. 52), ETL3 (about Ex. 53), ETL4 (about Ex. 54), ETL5 (about Ex. 55), ETL6 (about Ex. 56), ETL7 (about Ex. 57), ETL8 (about Ex. 58), ETL9 (about Ex. 59), and ETL10 (about Ex. 60) of Formula 16 are used instead of ETL1.

[0706] Experimental Example 6: Measurement of the luminescent properties of OLED

[0707] The optical properties of each OLED manufactured in Examples 51 to 60 were measured using the same procedure as in Example 1. The measurement results are shown in Table 6 below.

[0708] Table 6: Luminescent properties of OLEDs

[0709]

[0710]

[0711] As shown in Table 6, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0712] Example 61: Manufacturing of OLEDs

[0713] The OLED was manufactured using the same procedure and materials as in Example 1, except that HTL7 of Formula 12 was used in the HTL instead of HTL1.

[0714] Examples 62-70: OLED Manufacturing

[0715] The OLED is manufactured using the same procedures and materials as in Example 61, except that ETL2 (about Ex. 62), ETL3 (about Ex. 63), ETL4 (about Ex. 64), ETL5 (about Ex. 65), ETL6 (about Ex. 66), ETL7 (about Ex. 67), ETL8 (about Ex. 68), ETL9 (about Ex. 69), and ETL10 (about Ex. 70) of Formula 16 are used instead of ETL1.

[0716] Experimental Example 7: Measurement of the luminescent properties of OLED

[0717] The optical properties of each OLED manufactured in Examples 61 to 70 were measured using the same procedure as in Example 1. The measurement results are shown in Table 7 below.

[0718] Table 7: Luminescent properties of OLEDs

[0719]

[0720]

[0721] As shown in Table 7, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0722] Example 71: Manufacturing of OLEDs

[0723] The OLED was manufactured using the same procedure and materials as in Example 1, except that HTL8 of Formula 12 was used in the HTL instead of HTL1.

[0724] Examples 72-80: OLED Manufacturing

[0725] The OLED is manufactured using the same procedures and materials as in Example 71, except that ETL2 (about Ex. 72), ETL3 (about Ex. 73), ETL4 (about Ex. 74), ETL5 (about Ex. 75), ETL6 (about Ex. 76), ETL7 (about Ex. 77), ETL8 (about Ex. 78), ETL9 (about Ex. 79), and ETL10 (Ex. 80) of Formula 16 are used instead of ETL1.

[0726] Experimental Example 8: Measurement of the luminescent properties of OLED

[0727] The optical properties of each OLED manufactured in Examples 71 to 80 were measured using the same procedure as in Example 1. The measurement results are shown in Table 8 below.

[0728] Table 8: Luminescent properties of OLEDs

[0729]

[0730]

[0731] As shown in Table 8, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound and the ETL includes the benzimidazole-based organic compound, the driving voltage is reduced and the EQE and luminous lifetime (LT) are also reduced. 95 (This will greatly improve)

[0732] Example 81: Manufacturing of OLEDs

[0733] The OLED was manufactured using the same procedure and materials as in Example 1, except that HTL9 of Formula 12 was used in the HTL instead of HTL1.

[0734] Examples 82-90: OLED Manufacturing

[0735] The OLED is manufactured using the same procedures and materials as in Example 81, except that ETL2 (about Ex. 82), ETL3 (about Ex. 83), ETL4 (about Ex. 84), ETL5 (about Ex. 85), ETL6 (about Ex. 86), ETL7 (about Ex. 87), ETL8 (about Ex. 88), ETL9 (about Ex. 89), and ETL10 (about Ex. 90) of Formula 16 are used instead of ETL1.

[0736] Experimental Example 9: Measurement of the luminescent properties of OLED

[0737] The optical properties of each OLED manufactured in Examples 81 to 90 were measured using the same procedure as in Example 1. The measurement results are shown in Table 9 below.

[0738] Table 9: Luminescent properties of OLEDs

[0739]

[0740]

[0741] As shown in Table 9, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0742] Example 91: Manufacturing of OLEDs

[0743] The OLED was manufactured using the same procedure and materials as in Example 1, except that HTL10 of Formula 12 was used in the HTL instead of HTL1.

[0744] Examples 92-100: OLED Manufacturing

[0745] The OLED is manufactured using the same procedures and materials as in Example 91, except that ETL2 (about Ex. 92), ETL3 (about Ex. 93), ETL4 (about Ex. 94), ETL5 (about Ex. 95), ETL6 (about Ex. 96), ETL7 (about Ex. 97), ETL8 (about Ex. 98), ETL9 (about Ex. 99), and ETL10 (about Ex. 100) of Formula 16 are used instead of ETL1.

[0746] Experimental Example 10: Measurement of the luminescent properties of OLED

[0747] The optical properties of each OLED manufactured in Examples 91 to 100 were measured using the same procedure as in Example 1. The measurement results are shown in Table 10 below.

[0748] Table 10: Luminescent properties of OLEDs

[0749]

[0750]

[0751] As shown in Table 10, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also considered. 95 (This will greatly improve)

[0752] Example 101: Manufacturing of OLEDs

[0753] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 252 synthesized in Synthesis Example 16 was used instead of compound 251 as a dopant in the EML.

[0754] Examples 102-106: OLED Manufacturing

[0755] The OLED is manufactured using the same procedures and materials as in Example 101, except that ETL2 (regarding Ex. 102), ETL3 (regarding Ex. 103), ETL4 (regarding Ex. 104), ETL5 (regarding Ex. 105), and ETL6 (regarding Ex. 106) of Formula 16 are used instead of ETL1.

[0756] Example 107: Manufacturing of OLEDs

[0757] The OLED is manufactured using the same procedure and materials as in Example 101, except that HTL2 of Formula 12 is used in the HTL instead of HTL1.

[0758] Examples 108-112: OLED Manufacturing

[0759] The OLED is manufactured using the same procedures and materials as in Example 107, except that ETL2 (about Ex. 108), ETL3 (about Ex. 109), ETL4 (about Ex. 110), ETL5 (about Ex. 111), and ETL6 (about Ex. 112) of Formula 16 are used instead of ETL1.

[0760] Comparative Example 5 (Ref. 5): OLED Manufacturing

[0761] The OLED was manufactured using the same procedures and materials as in Example 101, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0762] Comparative Example 6 (Ref. 6): OLED Manufacturing

[0763] The OLED was manufactured using the same procedures and materials as in Example 101, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0764] Comparative Example 7 (Ref. 7): OLED Manufacturing

[0765] The OLED was manufactured using the same procedures and materials as in Example 101, except that HT-2 was used in the HTL instead of HTL1, and ET-1 was used in the ETL instead of ETL1.

[0766] Comparative Example 8 (Ref. 8): OLED Manufacturing

[0767] The OLED was manufactured using the same procedures and materials as in Example 101, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0768] Experimental Example 11: Measurement of the luminescent properties of OLED

[0769] The optical properties of each OLED manufactured in Examples 101 to 112 and Comparative Examples 5 to 8 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 11 below.

[0770] Table 11: Luminescent properties of OLEDs

[0771]

[0772] As shown in Table 11, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound and the ETL includes the benzimidazole-based organic compound, the driving voltage is reduced and the EQE and luminous lifetime (LT) are also reduced. 95 (This will greatly improve)

[0773] Example 113: OLED Manufacturing

[0774] The OLED is manufactured using the same procedure and materials as in Example 101, except that HTL3 of Formula 12 is used in the HTL instead of HTL1.

[0775] Examples 114-118: OLED Manufacturing

[0776] The OLED is manufactured using the same procedures and materials as in Example 113, except that ETL2 (about Ex. 114), ETL3 (about Ex. 115), ETL4 (about Ex. 116), ETL5 (about Ex. 117), and ETL6 (about Ex. 118) of Formula 16 are used instead of ETL1.

[0777] Example 119: Manufacturing of OLEDs

[0778] The OLED was manufactured using the same procedure and materials as in Example 101, except that HTL4 of Formula 12 was used in the HTL instead of HTL1.

[0779] Examples 120-124: OLED Manufacturing

[0780] The OLED is manufactured using the same procedures and materials as in Example 119, except that ETL2 (about Ex. 120), ETL3 (about Ex. 121), ETL4 (about Ex. 122), ETL5 (about Ex. 123), and ETL6 (about Ex. 124) of Formula 16 are used instead of ETL1.

[0781] Experimental Example 12: Measurement of the luminescent properties of OLED

[0782] The optical properties of each OLED manufactured in Examples 113 to 124 were measured using the same procedure as in Example 1. The measurement results are shown in Table 12 below.

[0783] Table 12: Luminescent properties of OLEDs

[0784]

[0785]

[0786] As shown in Table 12, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0787] Example 125: Manufacturing of OLEDs

[0788] The OLED was manufactured using the same procedure and materials as in Example 101, except that HTL5 of Formula 12 was used in the HTL instead of HTL1.

[0789] Examples 126-130: OLED Manufacturing

[0790] The OLED is manufactured using the same procedures and materials as in Example 125, except that ETL2 (about Ex. 126), ETL3 (about Ex. 127), ETL4 (about Ex. 128), ETL5 (about Ex. 129), and ETL6 (about Ex. 130) of Formula 16 are used instead of ETL1.

[0791] Example 131: Manufacturing of OLEDs

[0792] The OLED was manufactured using the same procedure and materials as in Example 101, except that HTL6 of Formula 12 was used in the HTL instead of HTL1.

[0793] Examples 132-136: OLED Manufacturing

[0794] The OLED is manufactured using the same procedures and materials as in Example 131, except that ETL2 (about Ex. 132), ETL3 (about Ex. 133), ETL4 (about Ex. 134), ETL5 (about Ex. 135), and ETL6 (about Ex. 136) of Formula 16 are used instead of ETL1.

[0795] Experimental Example 13: Measurement of the luminescent properties of OLED

[0796] The optical properties of each OLED manufactured in Examples 125 to 136 were measured using the same procedure as in Example 1. The measurement results are shown in Table 13 below.

[0797] Table 13: Luminescent properties of OLEDs

[0798]

[0799]

[0800] As shown in Table 13, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound and the ETL includes the benzimidazole-based organic compound, the driving voltage is reduced and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0801] Example 137: OLED Manufacturing

[0802] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 253 synthesized in Synthesis Example 17 was used instead of compound 251 as a dopant in the EML.

[0803] Examples 138-142: OLED Manufacturing

[0804] The OLED is manufactured using the same procedures and materials as in Example 137, except that ETL2 (about Ex. 138), ETL3 (about Ex. 139), ETL4 (about Ex. 140), ETL5 (about Ex. 141), and ETL6 (about Ex. 142) of Formula 16 are used instead of ETL1.

[0805] Example 143: Manufacturing of OLEDs

[0806] The OLED is manufactured using the same procedure and materials as in Example 137, except that HTL2 of Formula 12 is used in the HTL instead of HTL1.

[0807] Examples 144-148: OLED Manufacturing

[0808] The OLED is manufactured using the same procedures and materials as in Example 143, except that ETL2 (about Ex. 144), ETL3 (about Ex. 145), ETL4 (about Ex. 146), ETL5 (about Ex. 147), and ETL6 (about Ex. 148) of Formula 16 are used instead of ETL1.

[0809] Comparative Example 9 (Ref. 9): OLED Manufacturing

[0810] The OLED was manufactured using the same procedures and materials as in Example 137, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0811] Comparative Example 10 (Ref. 10): OLED Manufacturing

[0812] The OLED was manufactured using the same procedures and materials as in Example 137, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0813] Comparative Example 11 (Ref. 11): OLED Manufacturing

[0814] The OLED was manufactured using the same procedures and materials as in Example 137, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0815] Comparative Example 12 (Ref. 12): OLED Manufacturing

[0816] The OLED was manufactured using the same procedures and materials as in Example 137, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0817] Experimental Example 14: Measurement of the luminescent properties of OLED

[0818] The optical properties of each OLED manufactured in Examples 137 to 148 and Comparative Examples 9 to 12 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 14 below.

[0819] Table 14: Luminescent properties of OLEDs

[0820]

[0821] As shown in Table 14, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound and the ETL includes the benzimidazole-based organic compound, the driving voltage is reduced and the EQE and luminous lifetime (LT) are also reduced. 95 (This will greatly improve)

[0822] Example 149: Manufacturing of OLEDs

[0823] The OLED is manufactured using the same procedure and materials as in Example 137, except that HTL3 of Formula 12 is used in the HTL instead of HTL1.

[0824] Examples 150-154: OLED Manufacturing

[0825] The OLED is manufactured using the same procedures and materials as in Example 149, except that ETL2 (about Ex. 150), ETL3 (about Ex. 151), ETL4 (about Ex. 152), ETL5 (about Ex. 153), and ETL6 (about Ex. 154) of Formula 16 are used instead of ETL1.

[0826] Example 155: OLED Manufacturing

[0827] The OLED was manufactured using the same procedure and materials as in Example 137, except that HTL4 of Formula 12 was used in the HTL instead of HTL1.

[0828] Examples 156-160: OLED Manufacturing

[0829] The OLED is manufactured using the same procedures and materials as in Example 155, except that ETL2 (about Ex. 156), ETL3 (about Ex. 157), ETL4 (about Ex. 158), ETL5 (about Ex. 159), and ETL6 (about Ex. 160) of Formula 16 are used instead of ETL1.

[0830] Experimental Example 15: Measurement of the luminescent properties of OLED

[0831] The optical properties of each OLED manufactured in Examples 149 to 160 were measured using the same procedure as in Example 1. The measurement results are shown in Table 15 below.

[0832] Table 15: Luminescent properties of OLEDs

[0833]

[0834]

[0835] As shown in Table 15, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also considered. 95 (This will greatly improve)

[0836] Example 161: OLED Manufacturing

[0837] The OLED was manufactured using the same procedure and materials as in Example 137, except that HTL5 of Formula 12 was used in the HTL instead of HTL1.

[0838] Examples 162-166: OLED Manufacturing

[0839] The OLED is manufactured using the same procedures and materials as in Example 161, except that ETL2 (about Ex. 162), ETL3 (about Ex. 163), ETL4 (about Ex. 164), ETL5 (about Ex. 165), and ETL6 (about Ex. 166) of Formula 16 are used instead of ETL1.

[0840] Example 167: OLED Manufacturing

[0841] The OLED was manufactured using the same procedure and materials as in Example 137, except that HTL6 of Formula 12 was used in the HTL instead of HTL1.

[0842] Examples 168-172: OLED Manufacturing

[0843] The OLED is manufactured using the same procedures and materials as in Example 167, except that ETL2 (about Ex. 168), ETL3 (about Ex. 169), ETL4 (about Ex. 170), ETL5 (about Ex. 171), and ETL6 (about Ex. 172) of Formula 16 are used instead of ETL1.

[0844] Experimental Example 16: Measurement of the luminescent properties of OLED

[0845] The optical properties of each OLED manufactured in Examples 161 to 172 were measured using the same procedure as in Example 1. The measurement results are shown in Table 16 below.

[0846] Table 16: Luminescent properties of OLEDs

[0847]

[0848]

[0849] As shown in Table 16, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound and the ETL includes the benzimidazole-based organic compound, the driving voltage is reduced and the EQE and luminous lifetime (LT) are also reduced. 95 (This will greatly improve)

[0850] Example 173: OLED Manufacturing

[0851] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 254 synthesized in Synthesis Example 18 was used instead of compound 251 as a dopant in the EML.

[0852] Examples 174-178: OLED Manufacturing

[0853] The OLED is manufactured using the same procedures and materials as in Example 173, except that ETL2 (about Ex. 174), ETL3 (about Ex. 175), ETL4 (about Ex. 176), ETL5 (about Ex. 177), and ETL6 (about Ex. 178) of Formula 16 are used instead of ETL1.

[0854] Example 179: Manufacturing of OLEDs

[0855] The OLED was manufactured using the same procedure and materials as in Example 173, except that HTL2 of Formula 12 was used in the HTL instead of HTL1.

[0856] Examples 180-184: OLED Manufacturing

[0857] The OLED is manufactured using the same procedures and materials as in Example 179, except that ETL2 (about Ex. 180), ETL3 (about Ex. 181), ETL4 (about Ex. 182), ETL5 (about Ex. 183), and ETL6 (about Ex. 184) of Formula 16 are used instead of ETL1.

[0858] Comparative Example 13 (Ref. 13): OLED Manufacturing

[0859] The OLED was manufactured using the same procedures and materials as in Example 173, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0860] Comparative Example 14 (Ref. 14): OLED Manufacturing

[0861] The OLED was manufactured using the same procedure and materials as in Example 173, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0862] Comparative Example 15 (Ref. 15): OLED Manufacturing

[0863] The OLED was manufactured using the same procedures and materials as in Example 173, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0864] Comparative Example 16 (Ref. 16): OLED Manufacturing

[0865] The OLED was manufactured using the same procedures and materials as in Example 173, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0866] Experimental Example 17: Measurement of the luminescent properties of OLED

[0867] The optical properties of each OLED manufactured in Examples 173 to 184 and Comparative Examples 13 to 16 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 17 below.

[0868] Table 17: Luminescent properties of OLEDs

[0869]

[0870]

[0871] As shown in Table 17, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0872] Example 185: OLED Manufacturing

[0873] The OLED was manufactured using the same procedure and materials as in Example 173, except that HTL3 of Formula 12 was used in the HTL instead of HTL1.

[0874] Examples 186-190: OLED Manufacturing

[0875] The OLED is manufactured using the same procedures and materials as in Example 185, except that ETL2 (about Ex. 186), ETL3 (about Ex. 187), ETL4 (about Ex. 188), ETL5 (about Ex. 189), and ETL6 (about Ex. 190) of Formula 16 are used instead of ETL1.

[0876] Example 191: Manufacturing of OLEDs

[0877] The OLED was manufactured using the same procedure and materials as in Example 173, except that HTL4 of Formula 12 was used in the HTL instead of HTL1.

[0878] Examples 192-196: OLED Manufacturing

[0879] The OLED is manufactured using the same procedures and materials as in Example 191, except that ETL2 (about Ex. 192), ETL3 (about Ex. 193), ETL4 (about Ex. 194), ETL5 (about Ex. 195), and ETL6 (about Ex. 196) of Formula 16 are used instead of ETL1.

[0880] Experimental Example 18: Measurement of the luminescent properties of OLED

[0881] The optical properties of each OLED manufactured in Examples 185 to 196 were measured using the same procedure as in Example 1. The measurement results are shown in Table 18 below.

[0882] Table 18: Luminescent properties of OLEDs

[0883]

[0884]

[0885] As shown in Table 18, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0886] Example 197: Manufacturing of OLEDs

[0887] The OLED was manufactured using the same procedure and materials as in Example 173, except that HTL5 of Formula 12 was used in the HTL instead of HTL1.

[0888] Example 198-202: Manufacturing of OLEDs

[0889] The OLED is manufactured using the same procedures and materials as in Example 197, except that ETL2 (about Ex. 198), ETL3 (about Ex. 199), ETL4 (about Ex. 200), ETL5 (about Ex. 201), and ETL6 (about Ex. 202) of Formula 16 are used in the ETL process instead of ETL1.

[0890] Example 203: Manufacturing of OLED

[0891] The OLED was manufactured using the same procedure and materials as in Example 173, except that HTL6 of Formula 12 was used in the HTL instead of HTL1.

[0892] Examples 204-208: OLED Manufacturing

[0893] The OLED is manufactured using the same procedures and materials as in Example 203, except that ETL2 (about Ex. 204), ETL3 (about Ex. 205), ETL4 (about Ex. 206), ETL5 (about Ex. 207), and ETL6 (about Ex. 208) of Formula 16 are used instead of ETL1.

[0894] Experimental Example 19: Measurement of the luminescent properties of OLEDs

[0895] The optical properties of each OLED manufactured in Examples 197 to 208 were measured using the same procedure as in Example 1. The measurement results are shown in Table 19 below.

[0896] Table 19: Luminescent properties of OLEDs

[0897]

[0898] As shown in Table 19, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0899] Example 209: Manufacturing of OLED

[0900] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 255 synthesized in Synthesis Example 19 was used instead of compound 251 as a dopant in the EML.

[0901] Examples 210-214: OLED Manufacturing

[0902] The OLED is manufactured using the same procedures and materials as in Example 209, except that ETL2 (about Ex. 210), ETL3 (about Ex. 211), ETL4 (about Ex. 212), ETL5 (about Ex. 213), and ETL6 (about Ex. 214) of Formula 16 are used instead of ETL1.

[0903] Example 215: Manufacturing of OLEDs

[0904] The OLED is manufactured using the same procedure and materials as in Example 209, except that HTL2 of Formula 12 is used in the HTL instead of HTL1.

[0905] Examples 216-220: OLED Manufacturing

[0906] The OLED is manufactured using the same procedures and materials as in Example 215, except that ETL2 (about Ex. 216), ETL3 (about Ex. 217), ETL4 (about Ex. 218), ETL5 (about Ex. 219), and ETL6 (about Ex. 220) of Formula 16 are used instead of ETL1.

[0907] Comparative Example 17 (Ref. 17): OLED Manufacturing

[0908] The OLED was manufactured using the same procedures and materials as in Example 209, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0909] Comparative Example 18 (Ref. 18): OLED Manufacturing

[0910] The OLED was manufactured using the same procedures and materials as in Example 209, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0911] Comparative Example 19 (Ref. 19): OLED Manufacturing

[0912] The OLED was manufactured using the same procedures and materials as in Example 209, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0913] Comparative Example 20 (Ref. 20): OLED Manufacturing

[0914] The OLED was manufactured using the same procedures and materials as in Example 209, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0915] Experimental Example 20: Measurement of the luminescent properties of OLED

[0916] The optical properties of each OLED manufactured in Examples 209 to 220 and Comparative Examples 17 to 20 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 20 below.

[0917] Table 20: Luminescent properties of OLEDs

[0918]

[0919]

[0920] As shown in Table 20, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also considered. 95 (This will greatly improve)

[0921] Example 221: Manufacturing of OLEDs

[0922] The OLED is manufactured using the same procedure and materials as in Example 209, except that HTL3 of Formula 12 is used in the HTL instead of HTL1.

[0923] Examples 222-226: OLED Manufacturing

[0924] The OLED is manufactured using the same procedures and materials as in Example 221, except that ETL2 (about Ex. 222), ETL3 (about Ex. 223), ETL4 (about Ex. 224), ETL5 (about Ex. 225), and ETL6 (about Ex. 226) of Formula 16 are used instead of ETL1.

[0925] Example 227: Manufacturing of OLEDs

[0926] The OLED is manufactured using the same procedure and materials as in Example 209, except that HTL4 of Formula 12 is used in the HTL instead of HTL1.

[0927] Examples 228-232: OLED Manufacturing

[0928] The OLED is manufactured using the same procedures and materials as in Example 227, except that ETL2 (about Ex. 228), ETL3 (about Ex. 229), ETL4 (about Ex. 230), ETL5 (about Ex. 231), and ETL6 (about Ex. 232) of Formula 16 are used instead of ETL1.

[0929] Experimental Example 21: Measurement of the luminescent properties of OLED

[0930] The optical properties of each OLED manufactured in Examples 221 to 232 were measured using the same procedure as in Example 1. The measurement results are shown in Table 21 below.

[0931] Table 21: Luminescent properties of OLEDs

[0932]

[0933]

[0934] As shown in Table 21, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also considered. 95 (This will greatly improve)

[0935] Example 233: Manufacturing of OLEDs

[0936] The OLED is manufactured using the same procedure and materials as in Example 209, except that HTL5 of Formula 12 is used in the HTL instead of HTL1.

[0937] Examples 234-238: OLED Manufacturing

[0938] The OLED is manufactured using the same procedures and materials as in Example 233, except that ETL2 (about Ex. 234), ETL3 (about Ex. 235), ETL4 (about Ex. 236), ETL5 (about Ex. 237), and ETL6 (about Ex. 238) of Formula 16 are used instead of ETL1.

[0939] Example 239: Manufacturing of OLEDs

[0940] The OLED was manufactured using the same procedure and materials as in Example 209, except that HTL6 of Formula 12 was used in the HTL instead of HTL1.

[0941] Examples 240-244: OLED Manufacturing

[0942] The OLED is manufactured using the same procedures and materials as in Example 239, except that ETL2 (about Ex. 240), ETL3 (about Ex. 241), ETL4 (about Ex. 242), ETL5 (about Ex. 243), and ETL6 (about Ex. 244) of Formula 16 are used instead of ETL1.

[0943] Experimental Example 22: Measurement of the luminescent properties of OLED

[0944] The optical properties of each OLED manufactured in Examples 233 to 244 were measured using the same procedure as in Example 1. The measurement results are shown in Table 22 below.

[0945] Table 22: Luminescent properties of OLEDs

[0946]

[0947] As shown in Table 22, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[0948] Example 245: Manufacturing of OLEDs

[0949] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 256 synthesized in Synthesis Example 20 was used instead of compound 251 as a dopant in the EML.

[0950] Example 246: Manufacturing of OLEDs

[0951] The OLED is manufactured using the same procedure and materials as in Example 245, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[0952] Comparative Example 21 (Ref. 21): OLED Manufacturing

[0953] The OLED was manufactured using the same procedures and materials as in Example 245, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0954] Comparative Example 22 (Ref. 22): OLED Manufacturing

[0955] The OLED was manufactured using the same procedures and materials as in Example 245, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0956] Comparative Example 23 (Ref. 23): OLED Manufacturing

[0957] The OLED was manufactured using the same procedures and materials as in Example 245, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0958] Comparative Example 24 (Ref. 24): OLED Manufacturing

[0959] The OLED was manufactured using the same procedures and materials as in Example 245, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0960] Example 247: Manufacturing of OLEDs

[0961] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 257 synthesized in Synthesis Example 21 was used instead of compound 251 as a dopant in the EML.

[0962] Example 248: Manufacturing of OLEDs

[0963] The OLED is manufactured using the same procedure and materials as in Example 247, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[0964] Comparative Example 25 (Ref. 25): OLED Manufacturing

[0965] The OLED was manufactured using the same procedures and materials as in Example 247, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0966] Comparative Example 26 (Ref. 26): OLED Manufacturing

[0967] The OLED was manufactured using the same procedures and materials as in Example 247, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0968] Comparative Example 27 (Ref. 27): OLED Manufacturing

[0969] The OLED was manufactured using the same procedures and materials as in Example 247, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0970] Comparative Example 28 (Ref. 28): OLED Manufacturing

[0971] The OLED was manufactured using the same procedures and materials as in Example 247, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0972] Example 249: Manufacturing of OLEDs

[0973] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 1 synthesized in Synthesis Example 1 was used instead of compound 251 as a dopant in the EML.

[0974] Example 250: Manufacturing of OLEDs

[0975] The OLED is manufactured using the same procedure and materials as in Example 249, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[0976] Comparative Example 29 (Ref. 29): OLED Manufacturing

[0977] The OLED was manufactured using the same procedures and materials as in Example 249, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0978] Comparative Example 30 (Ref. 30): OLED Manufacturing

[0979] The OLED was manufactured using the same procedures and materials as in Example 249, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0980] Comparative Example 31 (Ref. 31): OLED Manufacturing

[0981] The OLED was manufactured using the same procedures and materials as in Example 249, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0982] Comparative Example 32 (Ref. 32): OLED Manufacturing

[0983] The OLED was manufactured using the same procedures and materials as in Example 249, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0984] Experimental Example 23: Measurement of the luminescent properties of OLED

[0985] The optical properties of each OLED manufactured in Examples 245 to 250 and Comparative Examples 21 to 32 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 23 below.

[0986] Table 23: Luminescent properties of OLEDs

[0987]

[0988]

[0989] As shown in Table 23, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also considered. 95 (This will greatly improve)

[0990] Example 251: Manufacturing of OLEDs

[0991] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 2 synthesized in Synthesis Example 2 was used instead of compound 251 as a dopant in the EML.

[0992] Example 252: Manufacturing of OLEDs

[0993] The OLED is manufactured using the same procedure and materials as in Example 251, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[0994] Comparative Example 33 (Ref. 33): OLED Manufacturing

[0995] The OLED was manufactured using the same procedures and materials as in Example 251, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[0996] Comparative Example 34 (Ref. 34): OLED Manufacturing

[0997] The OLED was manufactured using the same procedures and materials as in Example 251, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[0998] Comparative Example 35 (Ref. 35): OLED Manufacturing

[0999] The OLED was manufactured using the same procedures and materials as in Example 251, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1000] Comparative Example 36 (Ref. 36): OLED Manufacturing

[1001] The OLED was manufactured using the same procedures and materials as in Example 251, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1002] Example 253: Manufacturing of OLEDs

[1003] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 27 synthesized in Synthesis Example 5 was used instead of compound 251 as a dopant in the EML.

[1004] Example 254: OLED Manufacturing

[1005] The OLED is manufactured using the same procedure and materials as in Example 253, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1006] Comparative Example 37 (Ref. 37): OLED Manufacturing

[1007] The OLED was manufactured using the same procedures and materials as in Example 253, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1008] Comparative Example 38 (Ref. 38): OLED Manufacturing

[1009] The OLED was manufactured using the same procedures and materials as in Example 253, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1010] Comparative Example 39 (Ref. 39): OLED Manufacturing

[1011] The OLED was manufactured using the same procedures and materials as in Example 253, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1012] Comparative Example 40: OLED Manufacturing

[1013] The OLED was manufactured using the same procedures and materials as in Example 253, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1014] Example 255: Manufacturing of OLEDs

[1015] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 16 synthesized in Synthesis Example 3 was used instead of compound 251 as a dopant in the EML.

[1016] Example 256: Manufacturing of OLEDs

[1017] The OLED is manufactured using the same procedure and materials as in Example 255, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1018] Comparative Example 41 (Ref. 41): OLED Manufacturing

[1019] The OLED was manufactured using the same procedures and materials as in Example 255, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1020] Comparative Example 42 (Ref. 42): OLED Manufacturing

[1021] The OLED was manufactured using the same procedures and materials as in Example 255, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1022] Comparative Example 43 (Ref. 43): OLED Manufacturing

[1023] The OLED was manufactured using the same procedures and materials as in Example 255, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1024] Comparative Example 44: OLED Manufacturing

[1025] The OLED was manufactured using the same procedures and materials as in Example 255, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1026] Experimental Example 24: Measurement of the luminescent properties of OLED

[1027] The optical properties of each OLED manufactured in Examples 251 to 256 and Comparative Examples 33 to 44 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 24 below.

[1028] Table 24: Luminescent properties of OLEDs

[1029]

[1030] As shown in Table 24, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound and the ETL includes the benzimidazole-based organic compound, the driving voltage is reduced and the EQE and luminous lifetime (LT) are also reduced. 95 (This will greatly improve)

[1031] Example 257: Manufacturing of OLEDs

[1032] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 17 synthesized in Synthesis Example 4 was used instead of compound 251 as a dopant in the EML.

[1033] Example 258: Manufacturing of OLEDs

[1034] The OLED is manufactured using the same procedure and materials as in Example 257, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1035] Comparative Example 45: OLED Manufacturing

[1036] The OLED was manufactured using the same procedures and materials as in Example 257, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1037] Comparative Example 46: OLED Manufacturing

[1038] The OLED was manufactured using the same procedures and materials as in Example 257, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1039] Comparative Example 47: OLED Manufacturing

[1040] The OLED was manufactured using the same procedures and materials as in Example 257, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1041] Comparative Example 48 (Ref. 48): OLED Manufacturing

[1042] The OLED was manufactured using the same procedures and materials as in Example 257, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1043] Example 259: Manufacturing of OLEDs

[1044] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 32 synthesized in Synthesis Example 6 was used instead of compound 251 as a dopant in the EML.

[1045] Example 260: Manufacturing of OLEDs

[1046] The OLED is manufactured using the same procedure and materials as in Example 259, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1047] Comparative Example 49 (Ref. 49): OLED Manufacturing

[1048] The OLED was manufactured using the same procedures and materials as in Example 259, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1049] Comparative Example 50 (Ref. 50): OLED Manufacturing

[1050] The OLED was manufactured using the same procedures and materials as in Example 259, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1051] Comparative Example 51 (Ref. 51): OLED Manufacturing

[1052] The OLED was manufactured using the same procedures and materials as in Example 259, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1053] Comparative Example 52 (Ref. 52): OLED Manufacturing

[1054] The OLED was manufactured using the same procedures and materials as in Example 259, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1055] Example 261: Manufacturing of OLEDs

[1056] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 34 synthesized in Synthesis Example 7 was used instead of compound 251 as a dopant in the EML.

[1057] Example 262: OLED Manufacturing

[1058] The OLED is manufactured using the same procedure and materials as in Example 261, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1059] Comparative Example 53 (Ref. 53): OLED Manufacturing

[1060] The OLED was manufactured using the same procedures and materials as in Example 261, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1061] Comparative Example 54 (Ref. 54): OLED Manufacturing

[1062] The OLED was manufactured using the same procedure and materials as in Example 261, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1063] Comparative Example 55: OLED Manufacturing

[1064] The OLED was manufactured using the same procedures and materials as in Example 261, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1065] Comparative Example 56: OLED Manufacturing

[1066] The OLED was manufactured using the same procedures and materials as in Example 261, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1067] Experimental Example 25: Measurement of the luminescent properties of OLED

[1068] The optical properties of each OLED manufactured in Examples 257 to 262 and Comparative Examples 45 to 56 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 25 below.

[1069] Table 25: Luminescent properties of OLEDs

[1070]

[1071] As shown in Table 25, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also considered. 95 (This will greatly improve)

[1072] Example 263: OLED Manufacturing

[1073] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 35 synthesized in Synthesis Example 8 was used instead of compound 251 as a dopant in the EML.

[1074] Example 264: OLED Manufacturing

[1075] The OLED is manufactured using the same procedure and materials as in Example 263, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1076] Comparative Example 57: OLED Manufacturing

[1077] The OLED was manufactured using the same procedures and materials as in Example 263, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1078] Comparative Example 58 (Ref. 58): OLED Manufacturing

[1079] The OLED was manufactured using the same procedures and materials as in Example 263, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1080] Comparative Example 59 (Ref. 59): OLED Manufacturing

[1081] The OLED was manufactured using the same procedures and materials as in Example 263, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1082] Comparative Example 60 (Ref. 60): OLED Manufacturing

[1083] The OLED was manufactured using the same procedures and materials as in Example 263, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1084] Example 265: OLED Manufacturing

[1085] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 136 synthesized in Synthesis Example 9 was used instead of compound 251 as a dopant in the EML.

[1086] Example 266: Manufacturing of OLEDs

[1087] The OLED is manufactured using the same procedure and materials as in Example 265, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1088] Comparative Example 61 (Ref. 61): OLED Manufacturing

[1089] The OLED was manufactured using the same procedures and materials as in Example 265, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1090] Comparative Example 62 (Ref. 62): OLED Manufacturing

[1091] The OLED was manufactured using the same procedures and materials as in Example 265, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1092] Comparative Example 63 (Ref. 63): OLED Manufacturing

[1093] The OLED was manufactured using the same procedures and materials as in Example 265, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1094] Comparative Example 64 (Ref. 64): OLED Manufacturing

[1095] The OLED was manufactured using the same procedures and materials as in Example 265, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1096] Example 267: Manufacturing of OLEDs

[1097] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 137 synthesized in Synthesis Example 10 was used instead of compound 251 as a dopant in the EML.

[1098] Example 268: Manufacturing of OLEDs

[1099] The OLED is manufactured using the same procedure and materials as in Example 267, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1100] Comparative Example 65: OLED Manufacturing

[1101] The OLED was manufactured using the same procedures and materials as in Example 267, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1102] Comparative Example 66: OLED Manufacturing

[1103] The OLED was manufactured using the same procedures and materials as in Example 267, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1104] Comparative Example 67: OLED Manufacturing

[1105] The OLED was manufactured using the same procedures and materials as in Example 267, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1106] Comparative Example 68 (Ref. 68): OLED Manufacturing

[1107] The OLED was manufactured using the same procedures and materials as in Example 267, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1108] Experimental Example 26: Measurement of the luminescent properties of OLEDs

[1109] The optical properties of each OLED manufactured in Examples 263 to 268 and Comparative Examples 57 to 68 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 26 below.

[1110] Table 26: Luminescent properties of OLEDs

[1111]

[1112]

[1113] As shown in Table 26, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[1114] Example 269: Manufacturing of OLEDs

[1115] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 142 synthesized in Synthesis Example 12 was used instead of compound 251 as a dopant in the EML.

[1116] Example 270: Manufacturing of OLEDs

[1117] The OLED is manufactured using the same procedure and materials as in Example 269, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1118] Comparative Example 69 (Ref. 69): OLED Manufacturing

[1119] The OLED was manufactured using the same procedures and materials as in Example 269, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1120] Comparative Example 70 (Ref. 70): OLED Manufacturing

[1121] The OLED was manufactured using the same procedures and materials as in Example 269, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1122] Comparative Example 71 (Ref. 71): OLED Manufacturing

[1123] The OLED was manufactured using the same procedures and materials as in Example 269, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1124] Comparative Example 72 (Ref. 72): OLED Manufacturing

[1125] The OLED was manufactured using the same procedures and materials as in Example 269, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1126] Example 271: Manufacturing of OLEDs

[1127] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 148 synthesized in Synthesis Example 14 was used instead of compound 251 as a dopant in the EML.

[1128] Example 272: Manufacturing of OLEDs

[1129] The OLED is manufactured using the same procedure and materials as in Example 271, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1130] Comparative Example 73 (Ref. 73): OLED Manufacturing

[1131] The OLED was manufactured using the same procedure and materials as in Example 271, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1132] Comparative Example 74 (Ref. 74): OLED Manufacturing

[1133] The OLED was manufactured using the same procedure and materials as in Example 271, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1134] Comparative Example 75 (Ref. 75): Manufacturing of OLEDs

[1135] The OLED was manufactured using the same procedures and materials as in Example 271, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1136] Comparative Example 76 (Ref. 76): OLED Manufacturing

[1137] The OLED was manufactured using the same procedures and materials as in Example 271, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1138] Example 273: Manufacturing of OLEDs

[1139] The OLED was fabricated using the same procedure and materials as in Example 1, except that compound 147 synthesized in Synthesis Example 13 was used instead of compound 251 as a dopant in the EML.

[1140] Example 274: Manufacturing of OLEDs

[1141] The OLED is manufactured using the same procedure and materials as in Example 273, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1142] Comparative Example 77 (Ref. 77): OLED Manufacturing

[1143] The OLED was manufactured using the same procedure and materials as in Example 273, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1144] Comparative Example 78 (Ref. 78): OLED Manufacturing

[1145] The OLED was manufactured using the same procedure and materials as in Example 273, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1146] Comparative Example 79 (Ref. 79): OLED Manufacturing

[1147] The OLED was manufactured using the same procedures and materials as in Example 273, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1148] Comparative Example 80 (Ref. 80): OLED Manufacturing

[1149] The OLED was manufactured using the same procedures and materials as in Example 273, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1150] Experimental Example 27: Measurement of the luminescent properties of OLED

[1151] The optical properties of each OLED manufactured in Examples 269 to 274 and Comparative Examples 69 to 80 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 27 below.

[1152] Table 27: Luminescent properties of OLEDs

[1153]

[1154] As shown in Table 27, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[1155] Example 275: Manufacturing of OLEDs

[1156] The OLED was manufactured using the same procedure and materials as in Example 1, except that GHH5 of Formula 8 was used instead of GHH4 as the first host in the EML, and GEH3 of Formula 10 was used instead of GEH2 as the second host in the EML.

[1157] Example 276: Manufacturing of OLEDs

[1158] The OLED is manufactured using the same procedure and materials as in Example 275, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1159] Comparative Example 81 (Ref. 81): OLED Manufacturing

[1160] The OLED was manufactured using the same procedures and materials as in Example 275, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1161] Comparative Example 82 (Ref. 82): OLED Manufacturing

[1162] The OLED was manufactured using the same procedures and materials as in Example 275, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1163] Comparative Example 83 (Ref. 83): OLED Manufacturing

[1164] The OLED was manufactured using the same procedures and materials as in Example 275, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1165] Comparative Example 84 (Ref. 84): OLED Manufacturing

[1166] The OLED was manufactured using the same procedures and materials as in Example 275, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1167] Example 277: Manufacturing of OLEDs

[1168] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 252 synthesized in Synthesis Example 16 was used instead of compound 251 as a dopant in the EML.

[1169] Example 278: Manufacturing of OLEDs

[1170] The OLED is manufactured using the same procedure and materials as in Example 277, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1171] Comparative Example 85 (Ref. 85): OLED Manufacturing

[1172] The OLED was manufactured using the same procedures and materials as in Example 277, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1173] Comparative Example 86 (Ref. 86): OLED Manufacturing

[1174] The OLED was manufactured using the same procedure and materials as in Example 277, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1175] Comparative Example 87 (Ref. 87): OLED Manufacturing

[1176] The OLED was manufactured using the same procedures and materials as in Example 277, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1177] Comparative Example 88 (Ref. 88): OLED Manufacturing

[1178] The OLED was manufactured using the same procedures and materials as in Example 277, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1179] Example 279: Manufacturing of OLEDs

[1180] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 253 synthesized in Synthesis Example 17 was used instead of compound 251 as a dopant in the EML.

[1181] Example 280: Manufacturing of OLEDs

[1182] The OLED is manufactured using the same procedure and materials as in Example 279, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1183] Comparative Example 89 (Ref. 89): OLED Manufacturing

[1184] The OLED was manufactured using the same procedures and materials as in Example 279, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1185] Comparative Example 90 (Ref. 90): OLED Manufacturing

[1186] The OLED was manufactured using the same procedures and materials as in Example 279, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1187] Comparative Example 91 (Ref. 91): OLED Manufacturing

[1188] The OLED was manufactured using the same procedures and materials as in Example 279, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1189] Comparative Example 92 (Ref. 92): OLED Manufacturing

[1190] The OLED was manufactured using the same procedures and materials as in Example 279, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1191] Experimental Example 28: Measurement of the luminescent properties of OLED

[1192] The optical properties of each OLED manufactured in Examples 275 to 280 and Comparative Examples 81 to 92 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 28 below.

[1193] Table 28: Luminescent properties of OLEDs

[1194]

[1195] As shown in Table 28, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[1196] Example 281: Manufacturing of OLEDs

[1197] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 254 synthesized in Synthesis Example 18 was used instead of compound 251 as a dopant in the EML.

[1198] Example 282: Manufacturing of OLEDs

[1199] The OLED is manufactured using the same procedure and materials as in Example 281, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1200] Comparative Example 93 (Ref. 93): OLED Manufacturing

[1201] The OLED was manufactured using the same procedures and materials as in Example 281, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1202] Comparative Example 94 (Ref. 94): OLED Manufacturing

[1203] The OLED was manufactured using the same procedure and materials as in Example 281, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1204] Comparative Example 95 (Ref. 95): OLED Manufacturing

[1205] The OLED was manufactured using the same procedures and materials as in Example 281, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1206] Comparative Example 96 (Ref. 96): OLED Manufacturing

[1207] The OLED was manufactured using the same procedures and materials as in Example 281, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1208] Example 283: Manufacturing of OLEDs

[1209] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 255 synthesized in Synthesis Example 19 was used instead of compound 251 as a dopant in the EML.

[1210] Example 284: OLED Manufacturing

[1211] The OLED is manufactured using the same procedure and materials as in Example 283, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1212] Comparative Example 97 (Ref. 97): OLED Manufacturing

[1213] The OLED was manufactured using the same procedures and materials as in Example 283, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1214] Comparative Example 98 (Ref. 98): OLED Manufacturing

[1215] The OLED was manufactured using the same procedures and materials as in Example 283, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1216] Comparative Example 99 (Ref. 99): OLED Manufacturing

[1217] The OLED was manufactured using the same procedures and materials as in Example 283, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1218] Comparative Example 100 (Ref. 100): OLED Manufacturing

[1219] The OLED was manufactured using the same procedures and materials as in Example 283, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1220] Example 285: Manufacturing of OLEDs

[1221] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 256 synthesized in Synthesis Example 20 was used instead of compound 251 as a dopant in the EML.

[1222] Example 286: Manufacturing of OLEDs

[1223] The OLED is manufactured using the same procedure and materials as in Example 285, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1224] Comparative Example 101 (Ref. 101): OLED Manufacturing

[1225] The OLED was manufactured using the same procedures and materials as in Example 285, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1226] Comparative Example 102 (Ref. 102): OLED Manufacturing

[1227] The OLED was manufactured using the same procedures and materials as in Example 285, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1228] Comparative Example 103 (Ref. 103): OLED Manufacturing

[1229] The OLED was manufactured using the same procedures and materials as in Example 285, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1230] Comparative Example 104: OLED Manufacturing

[1231] The OLED was manufactured using the same procedures and materials as in Example 285, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1232] Experimental Example 29: Measurement of the luminescent properties of OLED

[1233] The optical properties of each OLED manufactured in Examples 281 to 286 and Comparative Examples 93 to 104 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 29 below.

[1234] Table 29: Luminescent properties of OLEDs

[1235]

[1236]

[1237] As shown in Table 29, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[1238] Example 287: Manufacturing of OLEDs

[1239] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 257 synthesized in Synthesis Example 21 was used instead of compound 251 as a dopant in the EML.

[1240] Example 288: Manufacturing of OLEDs

[1241] The OLED is manufactured using the same procedure and materials as in Example 287, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1242] Comparative Example 105: OLED Manufacturing

[1243] The OLED was manufactured using the same procedures and materials as in Example 287, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1244] Comparative Example 106: OLED Manufacturing

[1245] The OLED was manufactured using the same procedures and materials as in Example 287, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1246] Comparative Example 107: OLED Manufacturing

[1247] The OLED was manufactured using the same procedures and materials as in Example 287, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1248] Comparative Example 108: OLED Manufacturing

[1249] The OLED was manufactured using the same procedures and materials as in Example 287, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1250] Example 289: Manufacturing of OLEDs

[1251] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 1 synthesized in Synthesis Example 1 was used instead of compound 251 as a dopant in the EML.

[1252] Example 290: Manufacturing of OLEDs

[1253] The OLED is manufactured using the same procedure and materials as in Example 289, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1254] Comparative Example 109: OLED Manufacturing

[1255] The OLED was manufactured using the same procedures and materials as in Example 289, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1256] Comparative Example 110: OLED Manufacturing

[1257] The OLED was manufactured using the same procedures and materials as in Example 289, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1258] Comparative Example 111 (Ref. 111): OLED Manufacturing

[1259] The OLED was manufactured using the same procedures and materials as in Example 289, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1260] Comparative Example 112 (Ref. 112): OLED Manufacturing

[1261] The OLED was manufactured using the same procedures and materials as in Example 289, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1262] Example 291: Manufacturing of OLEDs

[1263] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 2 synthesized in Synthesis Example 2 was used instead of compound 251 as a dopant in the EML.

[1264] Example 292: Manufacturing of OLEDs

[1265] The OLED is manufactured using the same procedure and materials as in Example 291, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1266] Comparative Example 113 (Ref. 113): OLED Manufacturing

[1267] The OLED was manufactured using the same procedures and materials as in Example 291, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1268] Comparative Example 114: OLED Manufacturing

[1269] The OLED was manufactured using the same procedures and materials as in Example 291, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1270] Comparative Example 115: OLED Manufacturing

[1271] The OLED was manufactured using the same procedures and materials as in Example 291, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1272] Comparative Example 116: OLED Manufacturing

[1273] The OLED was manufactured using the same procedures and materials as in Example 291, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1274] Experimental Example 30: Measurement of the luminescent properties of OLED

[1275] The optical properties of each OLED manufactured in Examples 287 to 292 and Comparative Examples 105 to 116 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 30 below.

[1276] Table 30: Luminescent properties of OLEDs

[1277]

[1278] As shown in Table 30, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also considered. 95 (This will greatly improve)

[1279] Example 293: Manufacturing of OLEDs

[1280] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 27 synthesized in Synthesis Example 5 was used instead of compound 251 as a dopant in the EML.

[1281] Example 294: OLED Manufacturing

[1282] The OLED is manufactured using the same procedure and materials as in Example 293, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1283] Comparative Example 117: OLED Manufacturing

[1284] The OLED was manufactured using the same procedures and materials as in Example 293, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1285] Comparative Example 118 (Ref. 118): OLED Manufacturing

[1286] The OLED was manufactured using the same procedure and materials as in Example 293, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1287] Comparative Example 119: OLED Manufacturing

[1288] The OLED was manufactured using the same procedures and materials as in Example 293, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1289] Comparative Example 120 (Ref. 120): OLED Manufacturing

[1290] The OLED was manufactured using the same procedures and materials as in Example 293, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1291] Example 295: Manufacturing of OLEDs

[1292] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 16 synthesized in Synthesis Example 3 was used instead of compound 251 as a dopant in the EML.

[1293] Example 296: Manufacturing of OLEDs

[1294] The OLED is manufactured using the same procedure and materials as in Example 295, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1295] Comparative Example 121 (Ref. 121): OLED Manufacturing

[1296] The OLED was manufactured using the same procedures and materials as in Example 295, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1297] Comparative Example 122 (Ref. 122): OLED Manufacturing

[1298] The OLED was manufactured using the same procedures and materials as in Example 295, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1299] Comparative Example 123 (Ref. 123): OLED Manufacturing

[1300] The OLED was manufactured using the same procedures and materials as in Example 295, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1301] Comparative Example 124: OLED Manufacturing

[1302] The OLED was manufactured using the same procedures and materials as in Example 295, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1303] Example 297: Manufacturing of OLEDs

[1304] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 17 synthesized in Synthesis Example 4 was used instead of compound 251 as a dopant in the EML.

[1305] Example 298: Manufacturing of OLEDs

[1306] The OLED is manufactured using the same procedure and materials as in Example 297, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1307] Comparative Example 125 (Ref. 125): OLED Manufacturing

[1308] The OLED was manufactured using the same procedures and materials as in Example 297, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1309] Comparative Example 126: OLED Manufacturing

[1310] The OLED was manufactured using the same procedures and materials as in Example 297, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1311] Comparative Example 127: OLED Manufacturing

[1312] The OLED was manufactured using the same procedures and materials as in Example 297, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1313] Comparative Example 128 (Ref. 128): OLED Manufacturing

[1314] The OLED was manufactured using the same procedures and materials as in Example 297, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1315] Experimental Example 31: Measurement of the luminescent properties of OLED

[1316] The optical properties of each OLED manufactured in Examples 293 to 298 and Comparative Examples 117 to 128 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 31 below.

[1317] Table 31: Luminescent properties of OLEDs

[1318]

[1319] As shown in Table 31, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also considered. 95 (This will greatly improve)

[1320] Example 299: Manufacturing of OLEDs

[1321] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 32 synthesized in Synthesis Example 6 was used instead of compound 251 as a dopant in the EML.

[1322] Example 300: Manufacturing of OLEDs

[1323] The OLED is manufactured using the same procedure and materials as in Example 299, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1324] Comparative Example 129: OLED Manufacturing

[1325] The OLED was manufactured using the same procedures and materials as in Example 299, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1326] Comparative Example 130: OLED Manufacturing

[1327] The OLED was manufactured using the same procedures and materials as in Example 299, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1328] Comparative Example 131 (Ref. 131): OLED Manufacturing

[1329] The OLED was manufactured using the same procedures and materials as in Example 299, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1330] Comparative Example 132 (Ref. 132): OLED Manufacturing

[1331] The OLED was manufactured using the same procedures and materials as in Example 299, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1332] Example 301: Manufacturing of OLED

[1333] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 34 synthesized in Synthesis Example 7 was used instead of compound 251 as a dopant in the EML.

[1334] Example 302: Manufacturing of OLED

[1335] The OLED is manufactured using the same procedure and materials as in Example 301, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1336] Comparative Example 133 (Ref. 133): OLED Manufacturing

[1337] The OLED was manufactured using the same procedures and materials as in Example 301, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1338] Comparative Example 134 (Ref. 134): OLED Manufacturing

[1339] The OLED was manufactured using the same procedures and materials as in Example 301, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1340] Comparative Example 135: OLED Manufacturing

[1341] The OLED was manufactured using the same procedures and materials as in Example 301, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1342] Comparative Example 136: OLED Manufacturing

[1343] The OLED was manufactured using the same procedures and materials as in Example 301, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1344] Example 303: Manufacturing of OLED

[1345] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 35 synthesized in Synthesis Example 8 was used instead of compound 251 as a dopant in the EML.

[1346] Example 304: Manufacturing of OLEDs

[1347] The OLED is manufactured using the same procedure and materials as in Example 303, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1348] Comparative Example 137: OLED Manufacturing

[1349] The OLED was manufactured using the same procedures and materials as in Example 303, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1350] Comparative Example 138 (Ref. 138): OLED Manufacturing

[1351] The OLED was manufactured using the same procedure and materials as in Example 303, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1352] Comparative Example 139: OLED Manufacturing

[1353] The OLED was manufactured using the same procedures and materials as in Example 303, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1354] Comparative Example 140: OLED Manufacturing

[1355] The OLED was manufactured using the same procedures and materials as in Example 303, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1356] Experimental Example 32: Measurement of the luminescent properties of OLED

[1357] The optical properties of each OLED manufactured in Examples 299 to 304 and Comparative Examples 129 to 140 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 32 below.

[1358] Table 32: Luminescent properties of OLEDs

[1359]

[1360]

[1361] As shown in Table 32, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[1362] Example 305: Manufacturing of OLEDs

[1363] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 136 synthesized in Synthesis Example 9 was used instead of compound 251 as a dopant in the EML.

[1364] Example 306: Manufacturing of OLEDs

[1365] The OLED is manufactured using the same procedure and materials as in Example 305, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1366] Comparative Example 141: OLED Manufacturing

[1367] The OLED was manufactured using the same procedures and materials as in Example 305, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1368] Comparative Example 142: OLED Manufacturing

[1369] The OLED was manufactured using the same procedure and materials as in Example 305, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1370] Comparative Example 143: OLED Manufacturing

[1371] The OLED was manufactured using the same procedures and materials as in Example 305, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1372] Comparative Example 144: OLED Manufacturing

[1373] The OLED was manufactured using the same procedures and materials as in Example 305, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1374] Example 307: Manufacturing of OLEDs

[1375] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 137 synthesized in Synthesis Example 10 was used instead of compound 251 as a dopant in the EML.

[1376] Example 308: Manufacturing of OLED

[1377] The OLED is manufactured using the same procedure and materials as in Example 307, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1378] Comparative Example 145: OLED Manufacturing

[1379] The OLED was manufactured using the same procedures and materials as in Example 307, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1380] Comparative Example 146: OLED Manufacturing

[1381] The OLED was manufactured using the same procedures and materials as in Example 307, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1382] Comparative Example 147: OLED Manufacturing

[1383] The OLED was manufactured using the same procedures and materials as in Example 307, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1384] Comparative Example 148: OLED Manufacturing

[1385] The OLED was manufactured using the same procedures and materials as in Example 307, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1386] Example 309: Manufacturing of OLED

[1387] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 142 synthesized in Synthesis Example 12 was used instead of compound 251 as a dopant in the EML.

[1388] Example 310: Manufacturing of OLEDs

[1389] The OLED is manufactured using the same procedure and materials as in Example 309, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1390] Comparative Example 149: OLED Manufacturing

[1391] The OLED was manufactured using the same procedures and materials as in Example 309, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1392] Comparative Example 150 (Ref. 150): OLED Manufacturing

[1393] The OLED was manufactured using the same procedures and materials as in Example 309, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1394] Comparative Example 151 (Ref. 151): OLED Manufacturing

[1395] The OLED was manufactured using the same procedures and materials as in Example 309, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1396] Comparative Example 152 (Ref. 152): OLED Manufacturing

[1397] The OLED was manufactured using the same procedures and materials as in Example 309, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1398] Experimental Example 33: Measurement of the luminescent properties of OLED

[1399] The optical properties of each OLED manufactured in Examples 305 to 310 and Comparative Examples 141 to 152 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 33 below.

[1400] Table 33: Luminescent properties of OLEDs

[1401]

[1402] As shown in Table 33, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound, and the ETL includes the benzimidazole-based organic compound. The driving voltage is reduced, and the EQE and luminous lifetime (LT) are also improved. 95 (This will greatly improve)

[1403] Example 311: Manufacturing of OLEDs

[1404] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 148 synthesized in Synthesis Example 14 was used instead of compound 251 as a dopant in the EML.

[1405] Example 312: Manufacturing of OLEDs

[1406] The OLED is manufactured using the same procedure and materials as in Example 311, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1407] Comparative Example 153 (Ref. 153): OLED Manufacturing

[1408] The OLED was manufactured using the same procedures and materials as in Example 311, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1409] Comparative Example 154: OLED Manufacturing

[1410] The OLED was manufactured using the same procedure and materials as in Example 311, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1411] Comparative Example 155: OLED Manufacturing

[1412] The OLED was manufactured using the same procedure and materials as in Example 311, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1413] Comparative Example 156: OLED Manufacturing

[1414] The OLED was manufactured using the same procedures and materials as in Example 311, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1415] Example 313: Manufacturing of OLEDs

[1416] The OLED was fabricated using the same procedure and materials as in Example 275, except that compound 147 synthesized in Synthesis Example 13 was used instead of compound 251 as a dopant in the EML.

[1417] Example 314: Manufacturing of OLEDs

[1418] The OLED is manufactured using the same procedure and materials as in Example 313, except that ETL2 of Formula 16 is used in the ETL instead of ETL1.

[1419] Comparative Example 157 (Ref. 157): OLED Manufacturing

[1420] The OLED was manufactured using the same procedures and materials as in Example 313, except that HT-1 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1421] Comparative Example 158 (Ref. 158): OLED Manufacturing

[1422] The OLED was manufactured using the same procedures and materials as in Example 313, except that HT-1 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1423] Comparative Example 159: OLED Manufacturing

[1424] The OLED was manufactured using the same procedures and materials as in Example 313, except that HT-2 was used instead of HTL1 in the HTL and ET-1 was used instead of ETL1 in the ETL.

[1425] Comparative Example 160: OLED Manufacturing

[1426] The OLED was manufactured using the same procedures and materials as in Example 313, except that HT-2 was used instead of HTL1 in the HTL and ET-2 was used instead of ETL1 in the ETL.

[1427] Experimental Example 34: Measurement of the luminescent properties of OLED

[1428] The optical properties of each OLED manufactured in Examples 311 to 314 and Comparative Examples 153 to 160 were measured using the same procedure as in Test Example 1. The measurement results are shown in Table 34 below.

[1429] Table 34: Luminescent properties of OLEDs

[1430]

[1431] As shown in Table 34, in the OLED of this disclosure, the EML includes the host and the dopant, the HTL includes the spirodifluorenyl organic compound and the ETL includes the benzimidazole-based organic compound, the driving voltage is reduced and the EQE and luminous lifetime (LT) are also reduced. 95 (This will greatly improve)

[1432] In summary, as shown in Tables 1-34, by introducing the host and the dopant in the EML, the spirodifluorenyl organic compound in the HTL, and the benzimidazole-based organic compound in the ETL according to the present disclosure, an OLED with a lower driving voltage and improved luminous efficiency and luminous lifetime can be realized.

[1433] It will be apparent to those skilled in the art that various modifications and variations can be made to this disclosure without departing from its scope. Therefore, this disclosure is intended to cover such modifications and variations as long as they fall within the scope of the appended claims.

Claims

1. An organic light-emitting diode, comprising: First electrode; The second electrode facing the first electrode; and A light-emitting layer is disposed between the first electrode and the second electrode, and includes at least one light-emitting material layer, at least one hole transport layer disposed between the first electrode and the at least one light-emitting material layer, and at least one electron transport layer disposed between the at least one light-emitting material layer and the second electrode. The at least one luminescent material layer comprises: The main body includes: The structure represented by Equation 7 represents the first subject, and The second subject represented by the structure in Equation 9, and Dopants, including organometallic compounds represented by the structure of Formula 1, The at least one hole transport layer comprises an organic compound represented by the structure of Formula 11, and The at least one electron transport layer comprises an organic compound represented by the structure of Formula 13. in: Equation 1 is: [Formula 1] In Equation 1, L A It has a structure represented by Equation 2; L B It is an auxiliary ligand represented by the structure of formula 5A or formula 5B; m is 1, 2, or 3; n is 0, 1, or 2; and m + n is 3; Equation 2 is: [Equation 2] In Equation 2, X1 and X2 are each independently CR7 or N; X3 to X5 are each independently CR8 or N, and at least one of X3 to X5 is CR8; X6 to X9 are each independently CR9 or N, and at least one of X6 to X9 is CR9; R1 to R9 are each independently hydrogen, protium, deuterium, or unsubstituted or substituted C1-C. 20 Alkyl, unsubstituted or substituted C1-C 20 Heteroalkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Heterene, unsubstituted or substituted C1-C 20 Alkoxy, carboxyl, nitrile, isonitrile, sulfonamide, phosphine, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20 Alkylsilyl, unsubstituted or substituted C4-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 Heteroaryl, wherein when b is 2, 3 or 4, each R6 is the same or different from each other; Optionally, Two adjacent groups from R1 to R5, and / or When b is 2, 3, or 4, two adjacent R6, and / or X3 and X4 or X4 and X5, and / or X6 and X7, X7 and X8, or X8 and X9 Further, directly or indirectly, they are linked together to form unsubstituted or substituted C4-C. 20 Alicyclic, unsubstituted or substituted C3-C 20 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Mixed fragrance ring; a is 0, 1, or 2; and b is 0, 1, 2, 3, or 4. Equation 5A or Equation 5B is: [Formula 5A] [Formula 5B] In Equations 5A and 5B, R 21 R 22 and R 31 To R 33 Each is independently hydrogen, protium, deuterium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C1-C 20 Heteroalkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Heterene, unsubstituted or substituted C1-C 20 Alkoxy, carboxyl, nitrile, isonitrile, sulfonamide, phosphine, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20 Alkylsilyl, unsubstituted or substituted C4-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 Mixed aromatics, Optionally, When f is 2, 3, or 4, two adjacent R 21 and / or When g is 2, 3, or 4, two adjacent R 22 and / or R 31 and R 32 、or R 32 and R 33 They are further linked together to form unsubstituted or substituted C4-C 20 Alicyclic, unsubstituted or substituted C3-C 20 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Mixed aromatic rings; and f and g are each 0, 1, 2, 3 or 4. Equation 7 is: [Formula 7] In Equation 7, R 41 To R 44 Each is independently either unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 Heteroaryl, wherein when p is 2, 3, 4, 5, 6 or 7, each R 43 Whether they are the same or different, each R is equal to or different when q is 2, 3, 4, 5, 6 or 7. 44 Whether they are the same or different, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; and p and q are each independently 0, 1, 2, 3, 4, 5, 6 or 7. Equation 9 is: [Formula 9] In Equation 9, R 51 and R 52 Each is independently unsubstituted or substituted C6-C 30 aryl or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; Y1, Y2, and Y3 are each independently CR 53 Or N, where at least one of Y1, Y2, and Y3 is N; R 53 Independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; R 61 To R 68 Each is independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 10 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 The heterocyclic aromatic rings form a spiral structure. Optionally, R 61 To R 68 The two adjacent groups in the middle are further linked together to form an unsubstituted or substituted C6-C. 30 Aromatic ring, or unsubstituted or substituted C3-C 30 heterocyclic aromatic rings, optionally, unsubstituted or substituted C6-C 30 Aromatic rings and unsubstituted or substituted C3-C 30 Each heterocyclic ring independently interacts with unsubstituted or substituted C6-C. 20 Aromatic ring, or unsubstituted or substituted C3-C 20 Heteroaromatic rings form a spiral structure; R 69 and R 70 Each is independently unsubstituted or substituted C1-C 10 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a helical structure, wherein when j is 2 or 3, each R 69 They are either the same or different, and when k is 2 or 3, each R 70 Whether they are the same or different, Optionally, When j is 2 or 3, two adjacent R 69 and / or When k is 2 or 3, two adjacent R 70 They are further linked together to form unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 heterocyclic aromatic rings, optionally, unsubstituted or substituted C6-C 30 Aromatic rings and unsubstituted or substituted C3-C 30 Each heterocyclic ring independently interacts with unsubstituted or substituted C6-C. 20 Aromatic ring, or unsubstituted or substituted C3-C 20 Heteroaromatic rings form a spiral structure; L represents a single bond, and is either unsubstituted or substituted C6-C. 30 Aryl styrene, or unsubstituted or substituted C3-C 30 Hybrid aromatic styrene, optionally, unsubstituted or substituted C6-C 30 Aryl styrene and unsubstituted or substituted C3-C 30 Each heteroarylene independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; Z is either O or S; and j and k are each independently 0, 1, 2 or 3. Equation 11 is: [Equation 11] In Equation 11, R 61 and R 62 Each is independently unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, of which R 61 and R 62 At least one of them is a polycyclic aryl or polycyclic heteroaryl, optionally, an unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; R 63 To R 66 Each is independently unsubstituted or substituted C1-C 20 Alkyl, or unsubstituted or substituted C6-C 30 Aryl, wherein when r is 2, 3 or 4, each R 63 Whether they are the same or different, when s is 2, 3 or 4, each R 64 Whether they are the same or different, when t is 2, 3 or 4, each R 65 Whether they are the same or different, when u is 2, 3 or 4, each R 66 They are the same or different from each other; L1 to L3 are each independently a single bond, unsubstituted or substituted C6-C. 30 Aryl styrene, or unsubstituted or substituted C3-C 30 Hybrid aromatic styrene, optionally, unsubstituted or substituted C6-C 30 Aryl styrene and unsubstituted or substituted C3-C 30 Each heteroarylene independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; r, s, and t are each independently 0, 1, 2, 3, or 4; and u can be 0, 1, 2, or 3. Equation 13 is: [Equation 13] In Equation 13, R 71 To R 73 Each is independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spirostructure, in which R 71 To R 73 One of them has a structure represented by Equation 14: [Formula 14] In Equation 14, L4 is a single bond, unsubstituted or substituted C6-C. 30 Aryl styrene, or unsubstituted or substituted C3-C 30 Hybrid aromatic styrene, optionally, unsubstituted or substituted C6-C 30 Aryl styrene and unsubstituted or substituted C3-C 30 Each heteroarylene independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; When w is 0, Ar1 is unsubstituted or substituted C6-C. 30 aryl, or when w is 1, Ar1 is unsubstituted or substituted C6-C. 30 Aryl alkyl group, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C6-C 30 Aryl groups react independently with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; Ar2 is unsubstituted or substituted C6-C 30 Aryl; R 74 It is hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl; and w is 0 or 1.

2. The organic light-emitting diode according to claim 1, wherein the L A It has the following structure: Formula 4A or Formula 4B: [Formula 4A] [Formula 4B] in, In Equations 4A and 4B, Each of R1 to R6 and b is the same as that defined in Equation 2; R 11 To R 14 Each is independently hydrogen, protium, deuterium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C1-C 20 Heteroalkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Heterene, unsubstituted or substituted C1-C 20 Alkoxy, carboxyl, nitrile, isonitrile, sulfonamide, phosphine, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20 Alkylsilyl, unsubstituted or substituted C4-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 Mixed aromatics; Optionally, When d is 2 or 3 and e is 2, 3 or 4 When d is 2 or 3, two adjacent R 13 and / or When e is 2, 3, or 4, two adjacent R 14 They are further linked together to form unsubstituted or substituted C4-C 20 Alicyclic, unsubstituted or substituted C3-C 20 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Mixed fragrance ring; c is 0 or 1; d is 0, 1, 2, or 3; and e can be 0, 1, 2, 3, or 4.

3. The organic light-emitting diode according to claim 1, wherein the L A It has a structure with the following formula 4C or formula 4D: [Formula 4C] [Form 4D] In Equations 4C and 4D, Each of R1 to R6 and b is as defined in Equation 2; R 11 To R 14 Each is independently hydrogen, protium, deuterium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C1-C 20 Heteroalkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Heterene, unsubstituted or substituted C1-C 20 Alkoxy, carboxyl, nitrile, isonitrile, sulfonamide, phosphine, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20 Alkylsilyl, unsubstituted or substituted C4-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 Mixed aromatics; Optionally, When d is 2 or 3, two adjacent R 13 and / or When e is 2, 3, or 4, two adjacent R 14 They are further linked together to form unsubstituted or substituted C4-C 20 Alicyclic, unsubstituted or substituted C3-C 20 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Mixed fragrance ring; c is 0 or 1; d is 0, 1, 2, or 3; and e can be 0, 1, 2, 3, or 4.

4. The organic light-emitting diode according to claim 1, wherein X1 is CR7, X2 is CR7 or N, X3 to X5 are each independently CR8, and X6 to X9 are each independently CR9.

5. The organic light-emitting diode according to claim 1, wherein the organometallic compound is selected from the following compounds: 。 6. The organic light-emitting diode according to claim 1, wherein the organic compound having the structure represented by formula 11 is: 。 7. The organic light-emitting diode according to claim 1, wherein the organic compound having the structure represented by Formula 13 includes the organic compound having the structure represented by Formula 15: [Formula 15] In Equation 15, R 72 To R 74 Each is independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl; and Ar1 is unsubstituted or substituted C6-C 30 Fang Chengji.

8. The organic light-emitting diode according to claim 1, wherein the organic compound having the structure represented by formula 13 is: 。 9. The organic light-emitting diode according to claim 1, wherein the light-emitting layer comprises: A first light-emitting part is disposed between the first electrode and the second electrode and includes a first light-emitting material layer; The second light-emitting part is disposed between the first light-emitting part and the second electrode and includes a second light-emitting material layer; as well as A first charge generation layer is disposed between the first light-emitting part and the second light-emitting part. The first light-emitting portion includes a first light-emitting material layer, a first hole transport layer disposed between the first electrode and the first light-emitting material layer, and a first electron transport layer disposed between the first light-emitting material layer and the first charge generation layer. The second light-emitting portion includes a second light-emitting material layer, a second hole transport layer disposed between the first charge generating layer and the second light-emitting material layer, and a second electron transport layer disposed between the second light-emitting material layer and the second electrode. At least one of the first luminescent material layer and the second luminescent material layer includes the host and the dopant. At least one of the first hole transport layer and the second hole transport layer comprises an organic compound represented by the structure of Formula 11, and At least one of the first electron transport layer and the second electron transport layer comprises an organic compound represented by the structure of Formula 13.

10. The organic light-emitting diode according to claim 9, wherein the second light-emitting material layer comprises: The first layer is disposed between the second hole transport layer and the second electron transport layer; and The second layer is disposed between the first layer and the second electron transport layer. One of the first layer and the second layer includes the body and the dopant. The second hole transport layer comprises an organic compound represented by the structure of Formula 11, and The second electron transport layer comprises an organic compound represented by the structure of Formula 13.

11. The organic light-emitting diode of claim 10, wherein the second light-emitting material layer further comprises a third layer disposed between the first layer and the second layer.

12. The organic light-emitting diode according to claim 9, wherein the light-emitting layer further comprises: A third light-emitting portion, wherein the third light-emitting portion is disposed between the second light-emitting portion and the second electrode, and includes a third light-emitting material layer, and A second charge generation layer is disposed between the second light-emitting part and the third light-emitting part, and The third light-emitting part includes a third light-emitting material layer, a third hole transport layer disposed between the second charge generating layer and the second light-emitting material layer, and a third electron transport layer disposed between the third light-emitting material layer and the second electrode.

13. The organic light-emitting diode according to claim 12, wherein the second light-emitting material layer comprises: The first layer is disposed between the second hole transport layer and the second electron transport layer; and The second layer is disposed between the first layer and the second electron transport layer. One of the first layer and the second layer includes the body and the dopant. The second hole transport layer comprises an organic compound represented by the structure of Formula 11, and The second electron transport layer comprises an organic compound represented by the structure of Formula 13.

14. An organic light-emitting diode, comprising: First electrode; The second electrode facing the first electrode; and A light-emitting layer is disposed between the first electrode and the second electrode. The light-emitting layer includes: A first light-emitting part is disposed between the first electrode and the second electrode and includes a blue light-emitting material layer; A second light-emitting portion is disposed between the first light-emitting portion and the second electrode; and A first charge generation layer is disposed between the first light-emitting part and the second light-emitting part. The second light-emitting part includes: At least one luminescent material layer; A hole transport layer, wherein the hole transport layer is disposed between the first charge generation layer and the at least one light-emitting material layer; and An electron transport layer is disposed between the at least one luminescent material layer and the second electrode. The at least one luminescent material layer comprises: The main body includes: The first subject, and, represented by the structure of Equation 7 The second subject represented by the structure of Equation 9, and Dopants, including organometallic compounds represented by the structure of Formula 1, The hole transport layer comprises an organic compound represented by the structure of Formula 11, and The electron transport layer comprises an organic compound represented by the structure of Formula 13: in: Equation 1 is: [Formula 1] In Equation 1, L A It has a structure represented by Equation 2; L B It is an auxiliary ligand represented by the structure of formula 5A or formula 5B; m is 1, 2, or 3; n is 0, 1, or 2; and m + n is 3; Equation 2 is: [Equation 2] In Equation 2, X1 and X2 are each independently CR7 or N; X3 to X5 are each independently CR8 or N, and at least one of X3 to X5 is CR8; X6 to X9 are each independently CR9 or N, and at least one of X6 to X9 is CR9; R1 to R9 are each independently hydrogen, protium, deuterium, or unsubstituted or substituted C1-C. 20 Alkyl, unsubstituted or substituted C1-C 20 Heteroalkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Heterene, unsubstituted or substituted C1-C 20 Alkoxy, carboxyl, nitrile, isonitrile, sulfonamide, phosphine, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20 Alkylsilyl, unsubstituted or substituted C4-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 Heteroaryl, wherein when b is 2, 3 or 4, each R6 is the same or different from each other; Optionally, Two adjacent groups from R1 to R5, and / or When b is 2, 3, or 4, two adjacent R6, and / or X3 and X4 or X4 and X5, and / or X6 and X7, X7 and X8, or X8 and X9 They are further linked together to form unsubstituted or substituted C4-C 20 Alicyclic, unsubstituted or substituted C3-C 20 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Mixed fragrance ring; a is 0, 1, or 2; and b is 0, 1, 2, 3, or 4. Equation 5A or Equation 5B is: [Formula 5A] [Formula 5B] In Equations 5A and 5B, R 21 R 22 and R 31 To R 33 Each is independently hydrogen, protium, deuterium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C1-C 20 Heteroalkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Heterene, unsubstituted or substituted C1-C 20 Alkoxy, carboxyl, nitrile, isonitrile, sulfonamide, phosphine, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20 Alkylsilyl, unsubstituted or substituted C4-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 Mixed aromatics, Optionally, When f is 2, 3, or 4, two adjacent R 21 and / or When g is 2, 3, or 4, two adjacent R 22 and / or R 31 and R 32 、or R 32 and R 33 They are further linked together to form unsubstituted or substituted C4-C 20 Alicyclic, unsubstituted or substituted C3-C 20 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Mixed aromatic rings; and f and g are each 0, 1, 2, 3 or 4. Equation 7 is: [Formula 7] In Equation 7, R 41 To R 44 Each is independently either unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 Heteroaryl, wherein when p is 2, 3, 4, 5, 6 or 7, each R 43 Whether they are the same or different, each R is equal to or different when q is 2, 3, 4, 5, 6 or 7. 44 Whether they are the same or different, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; and p and q are each independently 0, 1, 2, 3, 4, 5, 6 or 7. Equation 9 is: [Formula 9] In Equation 9, R 51 and R 52 Each is independently unsubstituted or substituted C6-C 30 aryl or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; Y1, Y2, and Y3 are each independently CR 53 Or N, where at least one of Y1, Y2, and Y3 is N; R 53 Independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; R 61 To R 68 Each is independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 10 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 The heterocyclic aromatic rings form a spiral structure. Optionally, R 61 To R 68 The two adjacent groups in the middle are further linked together to form an unsubstituted or substituted C6-C. 30 Aromatic ring, or unsubstituted or substituted C3-C 30 heterocyclic aromatic rings, optionally, unsubstituted or substituted C6-C 30 Aromatic rings and unsubstituted or substituted C3-C 30 Each heterocyclic ring independently interacts with unsubstituted or substituted C6-C. 20 Aromatic ring, or unsubstituted or substituted C3-C 20 Heteroaromatic rings form a spiral structure; R 69 and R 70 Each is independently unsubstituted or substituted C1-C 10 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a helical structure, wherein when j is 2 or 3, each R 69 They are either the same or different, and when k is 2 or 3, each R 70 Whether they are the same or different, Optionally, When j is 2 or 3, two adjacent R 69 and / or When k is 2 or 3, two adjacent R 70 They are further linked together to form unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 heterocyclic aromatic rings, optionally, unsubstituted or substituted C6-C 30 Aromatic rings and unsubstituted or substituted C3-C 30 Each heterocyclic ring independently interacts with unsubstituted or substituted C6-C. 20 Aromatic ring, or unsubstituted or substituted C3-C 20 Heteroaromatic rings form a spiral structure; L represents a single bond, and is either unsubstituted or substituted C6-C. 30 Aryl styrene, or unsubstituted or substituted C3-C 30 Hybrid aromatic styrene, optionally, unsubstituted or substituted C6-C 30 Aryl styrene and unsubstituted or substituted C3-C 30 Each heteroarylene independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; Z is either O or S; and j and k are each independently 0, 1, 2 or 3. Equation 11 is: [Equation 11] In Equation 11, R 61 and R 62 Each is independently unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, of which R 61 and R 62 At least one of them is a polycyclic aryl or polycyclic heteroaryl, optionally, an unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; R 63 To R 66 Each is independently unsubstituted or substituted C1-C 20 Alkyl, or unsubstituted or substituted C6-C 30 Aryl, wherein when r is 2, 3 or 4, each R 63 Whether they are the same or different, when s is 2, 3 or 4, each R 64 Whether they are the same or different, when t is 2, 3 or 4, each R 65 Whether they are the same or different, when u is 2, 3 or 4, each R 66 They are the same or different from each other; L1 to L3 are each independently a single bond, unsubstituted or substituted C6-C. 30 Aryl styrene, or unsubstituted or substituted C3-C 30 Hybrid aromatic styrene, optionally, unsubstituted or substituted C6-C 30 Aryl styrene and unsubstituted or substituted C3-C 30 Each heteroarylene independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; r, s, and t are each independently 0, 1, 2, 3, or 4; and u can be 0, 1, 2, or 3. Equation 13 is: [Equation 13] In Equation 13, R 71 To R 73 Each is independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C3-C 30 Each heteroaryl group independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spirostructure, in which R 71 To R 73 One of them has a structure represented by Equation 14: [Formula 14] In Equation 14, L4 is a single bond, unsubstituted or substituted C6-C. 30 Aryl styrene, or unsubstituted or substituted C3-C 30 Hybrid aromatic styrene, optionally, unsubstituted or substituted C6-C 30 Aryl styrene and unsubstituted or substituted C3-C 30 Each heteroarylene independently reacts with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; When w is 0, Ar1 is unsubstituted or substituted C6-C. 30 aryl, or when w is 1, Ar1 is unsubstituted or substituted C6-C. 30 Aryl alkyl group, optionally, unsubstituted or substituted C6-C 30 Aryl and unsubstituted or substituted C6-C 30 Aryl groups react independently with unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Heteroaromatic rings form a spiral structure; Ar2 is unsubstituted or substituted C6-C 30 Aryl; R 74 It is hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl; and w is 0 or 1.

15. The organic light-emitting diode according to claim 14, wherein the L A It has the following structure: Formula 4A or Formula 4B: [Formula 4A] [Formula 4B] in, In Equations 4A and 4B, Each of R1 to R6 and b is the same as that defined in Equation 2; R 11 To R 14 Each is independently hydrogen, protium, deuterium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C1-C 20 Heteroalkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Heterene, unsubstituted or substituted C1-C 20 Alkoxy, carboxyl, nitrile, isonitrile, sulfonamide, phosphine, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20 Alkylsilyl, unsubstituted or substituted C4-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 Mixed aromatics; Optionally, When d is 2 or 3 and e is 2, 3 or 4 When d is 2 or 3, two adjacent R 13 and / or When e is 2, 3, or 4, two adjacent R 14 They are further linked together to form unsubstituted or substituted C4-C 20 Alicyclic, unsubstituted or substituted C3-C 20 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Mixed fragrance ring; c is 0 or 1; d is 0, 1, 2, or 3; and e can be 0, 1, 2, 3, or 4.

16. The organic light-emitting diode of claim 14, wherein the L... A It has a structure with the following formula 4C or formula 4D: [Formula 4C] [Form 4D] In Equations 4C and 4D, Each of R1 to R6 and b is as defined in Equation 2; R 11 To R 14 Each is independently hydrogen, protium, deuterium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C1-C 20 Heteroalkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Heterene, unsubstituted or substituted C1-C 20 Alkoxy, carboxyl, nitrile, isonitrile, sulfonamide, phosphine, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20 Alkylsilyl, unsubstituted or substituted C4-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 Mixed aromatics; Optionally, When d is 2 or 3, two adjacent R 13 and / or When e is 2, 3, or 4, two adjacent R 14 They are further linked together to form unsubstituted or substituted C4-C 20 Alicyclic, unsubstituted or substituted C3-C 20 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic ring, or unsubstituted or substituted C3-C 30 Mixed fragrance ring; c is 0 or 1; d is 0, 1, 2, or 3; and e can be 0, 1, 2, 3, or 4.

17. The organic light-emitting diode according to claim 14, wherein X1 is CR7, X2 is CR7 or N, X3 to X5 are each independently CR8, and X6 to X9 are each independently CR9.

18. The organic light-emitting diode of claim 14, wherein the organic compound having the structure of formula 13 includes the organic compound represented by the structure of formula 15: [Formula 15] In Equation 15, R 72 To R 74 Each is independently hydrogen, protium, deuterium, tritium, unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C6-C 30 aryl, or unsubstituted or substituted C3-C 30 heteroaryl; and Ar1 is unsubstituted or substituted C6-C 30 Fang Chengji.

19. The organic light-emitting diode of claim 14, wherein the at least one light-emitting material layer comprises: The first layer is disposed between the hole transport layer and the electron transport layer, and includes a red luminescent material layer; and The second layer is disposed between the first layer and the electron transport layer, and includes the body and the dopant.

20. The organic light-emitting diode of claim 19, wherein the at least one light-emitting material layer further comprises a third layer disposed between the first layer and the second layer, and wherein the third layer comprises a yellow-green light-emitting material layer.

21. The organic light-emitting diode of claim 14, wherein the light-emitting layer further comprises: The third light-emitting part is disposed between the second light-emitting part and the second electrode and includes a blue light-emitting material layer; and The second charge generation layer is disposed between the second light-emitting part and the third light-emitting part.

22. The organic light-emitting diode according to claim 21, wherein the at least one light-emitting material layer comprises: The first layer is disposed between the hole transport layer and the electron transport layer, and includes a red luminescent material layer; and The second layer is disposed between the first layer and the electron transport layer, and includes the body and the dopant.

23. The organic light-emitting diode of claim 22, wherein the at least one light-emitting material layer further comprises a third layer disposed between the first layer and the second layer, and wherein the third layer comprises a yellow-green light-emitting material layer.

24. An organic light-emitting device, comprising: substrate; and An organic light-emitting diode as described in claim 1 is disposed above the substrate.

25. An organic light-emitting device, comprising: substrate; and An organic light-emitting diode as described in claim 14 is disposed above the substrate.

26. The organic light-emitting diode according to claim 1, wherein the first main body represented by the structure indicated by formula 7 is: 。 27. The organic light-emitting diode according to claim 1, wherein the second main body represented by the structure indicated by formula 9 is: 。

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