Compound, light emitting device including compound, electronic device including light emitting device, and electronic apparatus including electronic device

Abstract

Provided are a compound, a light emitting device including the compound, an electronic device including the light emitting device, and an electronic apparatus including the electronic device, the light emitting device including a first electrode, a second electrode facing the first electrode, and an intermediate layer disposed between the first electrode and the second electrode and including an emission layer, the emissive layer includes a compound having both a pyridine group and an anthracene group, the pyridine group and the anthracene group being geometrically arranged to provide an orthogonal relationship between planes defined by the two groups. The vibration recombination energy value of the compound is reduced due to the molecular structure.

Description

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0124257 filed in the Korean Intellectual Property Office on September 18, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0002] One or more aspects of the embodiments of the present disclosure relate to a compound, a light emitting device including the compound, an electronic device including the light emitting device, and an electronic device including the electronic device. Background Art

[0003] The light emitting device is a so-called "self-emissive" device: compared with other display devices in the prior art, it has a relatively wide viewing angle, a relatively high contrast, a relatively short response time and / or excellent or suitable characteristics in terms of brightness, driving voltage and / or response speed.

[0004] In the light-emitting device, a first electrode is arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons, which can then transition (i.e., relax) from an excited state to a ground state, thereby generating light. Summary of the invention

[0005] One or more aspects of the embodiments of the present disclosure relate to a light emitting device and an electronic device including the same.

[0006] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented disclosed embodiments.

[0007] According to one or more embodiments, a light emitting device includes:

[0008] a first electrode;

[0009] a second electrode facing the first electrode; and

[0010] an intermediate layer, arranged between the first electrode and the second electrode and including an emission layer,

[0011] Wherein, the emission layer includes a compound represented by Formula 1:

[0012] Formula 1

[0013] ML 401 L 402

[0014] Formula 1-1

[0015]

[0016] Formula 1-2

[0017]

[0018] Among them, in Formula 1, Formula 1-1 and Formula 1-2,

[0019] M can be a transition metal,

[0020] L 401 and L 402 Can be independently Formula 1-1 or Formula 1-2, wherein, from L 401 and L 402 At least one selected from may include formula 1-2,

[0021] X 401 and X 402 can all independently be N or C,

[0022] Ring A 401 and Ring A 402 can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0023] T 401 It may be a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、-C(Q 411 )=or=C=,

[0024] X 403 and X 404 can be independently a chemical bond, O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),

[0025] R 401 To R 405 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1 -C 20 Alkyl, unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) or -P(=O)(Q 401 )(Q 402 ),

[0026] xc11 and xc12 may each independently be an integer from 0 to 10,

[0027] xc13 and xc14 may each independently be an integer from 0 to 4,

[0028] xc15 can be an integer from 0 to 3,

[0029] * and *' in Formula 1-1 and Formula 1-2 both represent the binding site with M in Formula 1,

[0030] Formula 1-1 and Formula 1-2 can be optionally connected via T 402 Connect to each other, T 402 is a linker and as referred to in T 401 As defined,

[0031] R 10a Can be:

[0032] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro,

[0033] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C60 Arylthio, C 7 -C 60 Arylalkyl, C 2 -C 60 Heteroarylalkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy,

[0034] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl, C 2 -C 60 Heteroarylalkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl, or

[0035] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and

[0036] Q 11 To Q 13 , Q 21 To Q 23 , Q 31 To Q 33 , Q 401 To Q 403 and Q 411 To Q 414 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy, or

[0037] All are unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C alkoxy, phenyl, biphenyl or any combination thereof 3 -C 60Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroarylalkyl.

[0038] According to one or more embodiments,

[0039] The electronic device includes the light emitting device.

[0040] According to one or more embodiments,

[0041] The electronic device comprises the electronic device.

[0042] According to one or more embodiments,

[0043] The compound represented by Formula 1 is provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0044] The accompanying drawings are included to provide a further understanding of the foregoing and other aspects, features and advantages of certain disclosed embodiments, and are incorporated in and constitute a part of this specification. The accompanying drawings, together with the following description in conjunction with the accompanying drawings, illustrate example embodiments. In the drawings:

[0045] Figure 1 is a schematic diagram of the structure of a light emitting device according to one or more embodiments of the present disclosure;

[0046] Figure 2 is a cross-sectional view of an electronic device according to one or more embodiments of the present disclosure;

[0047] Figure 3 is a cross-sectional view of an electronic device according to one or more embodiments of the present disclosure;

[0048] Figure 4 is a schematic perspective view of an electronic device including a light emitting device according to one or more embodiments of the present disclosure;

[0049] Figure 5 is a schematic diagram of the exterior of a vehicle as an electronic device including a light emitting device according to one or more embodiments of the present disclosure; and

[0050] Fig. 6A , Figure 6B and Figure 6C Each is a schematic diagram of the interior of a vehicle as an electronic device including a light emitting device according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION

[0051] Now will refer to embodiment in more detail, the example of embodiment is shown in the accompanying drawings, wherein, in the whole specification, the same reference numeral refers to the same element, and its repeated description may not be provided. In this regard, the embodiment given may have different forms, and should not be interpreted as being limited to the description set forth herein. Therefore, the embodiment is described only by reference to the accompanying drawings to explain the aspects of this specification. As used herein, the term "and / or" includes any combination and all combinations of one or more of the relevant listed items. When expressions such as "at least one (kind / person) in ...", "one (kind / person) in ..." and "selected from ... (selected from ...)" are placed before (or after) a column of elements, the entire column of elements is modified, without modifying the individual elements of the column. For example, in the whole disclosure, the expression "at least one (kind / person) in a, b and c" means only a, only b, only c, both a and b (e.g., a and b at the same time), both a and c (e.g., a and c at the same time), both b and c (e.g., b and c at the same time), all of a, b and c or their variations.

[0052] Unless otherwise defined, all chemical names, technical terms and scientific terms and terms defined in general dictionaries should be interpreted as having a meaning consistent with the context of the relevant field, and should not be interpreted in an ideal or overly formal sense. It will be understood that, although the terms first, second, etc. can be used to describe various elements here, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Therefore, without departing from the teaching of the present disclosure, the first element can be referred to as the second element. Similarly, the second element can be referred to as the first element.

[0053] As used herein, singular forms such as “a,” “an,” and “the” are intended to include plural forms as well, unless the context clearly indicates otherwise.

[0054] It will also be understood that when the terms "includes," "comprising," "having" and / or their variations are used in this specification, it indicates the presence of stated features, steps, operations, elements and / or components, but does not exclude the presence or addition of one or more other features, steps, operations, elements, components and / or groups thereof.

[0055] As used herein, the term "use" and variations thereof may be considered synonymous with the term "utilize" and variations thereof, respectively.

[0056] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items.

[0057] The term "may" will be understood to refer to "one or more embodiments of the present disclosure," some of which include the described elements, and some of which do not include the elements and / or include alternative elements. Similarly, alternative language such as "or" refers to "one or more embodiments of the present disclosure," each of which includes the corresponding listed items.

[0058] It will be understood that when an element is referred to as being "on," "connected to," or "coupled to" another element, the element may be directly on, directly connected to, or directly coupled to the other element, or one or more intervening elements may also be present. When an element is referred to as being "directly on," "directly connected to," or "directly coupled to" another element, there are no intervening elements.

[0059] For ease of description, spatially relative terms such as "under," "below," "down," "above," "up," "bottom," "top," etc. may be used herein to describe the relationship of one element or feature to another element or feature as shown in the accompanying drawings. It will be understood that the spatially relative terms are intended to cover different orientations of the device in use or operation in addition to the orientation shown in the accompanying drawings. For example, if the device in the accompanying drawings is turned over, an element described as "under" or "beneath" other elements or features will subsequently be oriented as "above" or "on" the other elements or features. Thus, the term "under" can cover both above and below orientations. The device may be otherwise oriented (rotated 90 degrees or in other orientations), and the spatially relative descriptors used herein should be interpreted accordingly.

[0060] In this context, "consisting essentially of" means that any additional components will not substantially affect the chemical, physical, optical, or electrical properties of the semiconductor film.

[0061] In the present disclosure, "does not include (or does not contain) one or any "component", "excludes (or does not include) one or any "component"" and / or "no component" etc. means that the "component" is not added, selected or used as a component in the element / composition, but due to other impurities and / or external factors, less than the appropriate amount of the "component" may still be included.

[0062] Furthermore, in this specification, the phrase "on a plane" or "plan view" means viewing a target portion from the top, and the phrase "in section" means viewing a section formed by vertically cutting the target portion from the side.

[0063] Regarding the related art using a platinum-based organometallic complex as a green or red phosphorescent material as a green or red phosphorescent dopant, it has been reported that by using a tetradentate ligand connected to each other via a linker to form a six-membered ring, compared with the existing case of using a bidentate ligand or a tridentate ligand connected to each other, structural stability can be ensured, so that molecular vibration can be reduced, and thus the life and efficiency of the light-emitting material can be improved. However, in this case, the formation of excimers due to the structural characteristics of the platinum-based organometallic compound having a planar shape is considered to be a problem.

[0064] Light-emitting devices

[0065] A light emitting device according to one aspect may include:

[0066] a first electrode;

[0067] a second electrode facing the first electrode; and

[0068] an intermediate layer, between the first electrode and the second electrode, and including an emission layer,

[0069] Wherein, the emission layer may include a compound represented by Formula 1:

[0070] Formula 1

[0071] ML 401 L 402

[0072] Formula 1-1

[0073]

[0074] Formula 1-2

[0075]

[0076] Among them, in Formula 1, Formula 1-1 and Formula 1-2,

[0077] M can be a transition metal,

[0078] L 401 and L 402 Can be independently Formula 1-1 or Formula 1-2, wherein, from L 401 and L 402 At least one selected from may include formula 1-2,

[0079] X 401 and X 402 can all independently be N or C,

[0080] Ring A 401 and Ring A 402 can be independently C 3 -C60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0081] T 401 It may be a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、-C(Q 411 )=or=C=,

[0082] X 403 and X 404 can be independently a chemical bond, O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),

[0083] R 401 To R 405 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkyl, unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) or -P(=O)(Q 401 )(Q 402 ),

[0084] xc11 and xc12 may each independently be an integer from 0 to 10,

[0085] xc13 and xc14 may each independently be an integer from 0 to 4,

[0086] xc15 can be an integer from 0 to 3,

[0087] * and *' in Formula 1-1 and Formula 1-2 both represent the binding site with M in Formula 1,

[0088] Formula 1-1 and Formula 1-2 can be optionally connected via T 402 Connect to each other, T 402 is a linker and as referred to in T 401 As defined,

[0089] R 10a Can be:

[0090] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0091] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl, C 2 -C 60 Heteroarylalkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy;

[0092] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl, C 2 -C 60 Heteroarylalkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl; or

[0093] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q31 ) or -P(=O)(Q 31 )(Q 32 ),and

[0094] Q 11 To Q 13 , Q 21 To Q 23 , Q 31 To Q 33 , Q 401 To Q 403 and Q 411 To Q 414 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; or C 1 -C 60 Alkoxy; or

[0095] All are unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C alkoxy, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroarylalkyl.

[0096] In one or more embodiments, the first electrode may be an anode and the second electrode may be a cathode, and

[0097] The intermediate layer may further include an electron transport region disposed between the second electrode and the emission layer and including an electron transport layer, a hole blocking layer, an electron injection layer, or any combination thereof.

[0098] In one or more embodiments, the first electrode may be an anode and the second electrode may be a cathode, and

[0099] The intermediate layer may further include a hole transport region disposed between the first electrode and the emission layer and including a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.

[0100] In one or more embodiments, the emission layer may include a host and a dopant, and the dopant may include a compound represented by Formula 1.

[0101] In one or more embodiments, the emissive layer may be a green emissive layer (ie, the emissive layer may emit green light).

[0102] The compound according to another aspect may be represented by Formula 1:

[0103] Formula 1

[0104] ML 401 L 402

[0105] Formula 1-1

[0106]

[0107] Formula 1-2

[0108]

[0109] Among them, in Formula 1, Formula 1-1 and Formula 1-2,

[0110] M can be a transition metal,

[0111] L 401 and L 402 Can be independently Formula 1-1 or Formula 1-2, wherein, from L 401 and L 402 At least one selected from may include formula 1-2,

[0112] X 401 and X 402 can all independently be N or C,

[0113] Ring A 401 and Ring A 402 can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0114] T 401 It may be a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、-C(Q 411 )=or=C=,

[0115] X 403 and X404 can be independently a chemical bond, O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),

[0116] R 401 To R 405 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkyl, unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) or -P(=O)(Q 401 )(Q 402 ),

[0117] xc11 and xc12 may each independently be an integer from 0 to 10,

[0118] xc13 and xc14 may each independently be an integer from 0 to 4,

[0119] xc15 can be an integer from 0 to 3,

[0120] * and *' in Formula 1-1 and Formula 1-2 both represent the binding site with M in Formula 1,

[0121] Formula 1-1 and Formula 1-2 can be optionally connected via T 402 Connect to each other, T 402 is a linker and as referred to in T 401 As defined,

[0122] R 10a Can be:

[0123] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0124] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl, C 2 -C 60 Heteroarylalkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy;

[0125] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6-C 60 Arylthio, C 7 -C 60 Arylalkyl, C 2 -C 60 Heteroarylalkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl; or

[0126] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and

[0127] Q 11 To Q 13 , Q 21 To Q 23 , Q 31 To Q 33 , Q 401 To Q 403 and Q 411 To Q 414 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; or C 1 -C 60 Alkoxy; or

[0128] All are unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C alkoxy, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroarylalkyl.

[0129] In one or more embodiments, in Formula 1-2 (i.e., the compound represented by Formula 1-2), the pyridine moiety and the N-bridged anthracene moiety may be orthogonal to each other. For example, in Formula 1-2, and can be orthogonal to each other. For example, in formula 1-2, and The term "orthogonal" does not refer to (e.g., excludes) an angle of exactly 90°. This may mean that the plane of the pyridine moiety and the plane of the phenyl moiety in the N-bridged anthracene moiety occupy space in an arrangement in which the planes are orthogonal to each other rather than parallel to each other.

[0130] After the electrons in the molecule are excited, the molecule vibrates to stabilize the molecular structure, thereby causing the rearrangement of the molecular structure, and the energy utilized at this time can be referred to as vibrational reorganization energy. Thus, for example, high vibrational reorganization energy can refer to the energy in the excited state not causing luminescence, and the quantum efficiency of the molecule is reduced due to vibration.

[0131] The compound represented by Formula 1 according to one or more embodiments may include a moiety represented by Formula 1-2, and thus, the compound may have a reciprocal centimeter (cm -1 ) or less and is stable, thereby having an excellent or suitable lifespan.

[0132] In one or more embodiments, Ring A 401 and Ring A 402 may be independently unsubstituted or substituted with at least one R10a C 6 -C 60 Aryl, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heteroaryl is either unsubstituted or substituted with at least one R 10a A monovalent non-aromatic condensed heteropolycyclic group.

[0133] For example, Ring A 401 and Ring A 402 may be independently unsubstituted or substituted with at least one R 10a benzene group, pentalene group, naphthyl group, azulene group, indacene group, acenaphthene group, phenanthrenyl group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, The invention may be any of the following: a quinoline group, a benzoquinoline group, an isoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a cinnoline group, a phenanthroline group, a phthalazine group, a naphthylene group, a phenanthroline group, a hexaphenylene group, a pentacene group, a rubridene group, a coronene group, an ovalbuminyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, a benzoquinoline group, an isoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a cinnoline group, a phenanthroline group, a phthalazine group, a naphthyridine group, an imidazole group, or a benzimidazole group.

[0134] In one or more embodiments, M may be iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm). For example, M may be Pt.

[0135] In one or more embodiments, in Formula 1-1, A 402 It can be benzene, R 401 It may be a terphenyl group, and xc11 may be an integer of 1 to 3.

[0136] In one or more embodiments, in Formula 1-1, A 401 It can be benzimidazole, R 401 It may be a terphenyl group, and xc11 may be an integer of 1 to 3.

[0137] In one or more embodiments, Formula 1-1 and Formula 1-2 can be linked via a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、-C(Q 411)= or =C= are connected to each other. For example, A in Formula 1-1 401 The pyridine portion in Formula 1-2 can be connected via a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、-C(Q 411 )= or =C= are connected to each other. For example, A in Formula 1-1 402 The N-bridged anthracene moiety in Formula 1-2 can be connected via a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、-C(Q 411 )=or=C= are connected to each other.

[0138] In one or more embodiments, Formula 1-2 can be represented by Formula 1-3:

[0139] Formula 1-3

[0140]

[0141] Among them, in formula 1-3, R 403 To R 405 and xc13 to xc15 may all be defined as with reference to Formula 1-2.

[0142] In one or more embodiments, in Formula 1, L 401 It can be expressed as formula 1-1, and L 402 It can be expressed as formula 1-3, and

[0143] A in formula 1-1 402 The N-bridged anthracene moiety in Formula 1-3 can be connected via a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、-C(Q 411 )=or=C= are connected to each other.

[0144] In one or more embodiments, Formula 1 can be represented by Formula 2:

[0145] Formula 2

[0146]

[0147] Among them, in formula 2,

[0148] M can be a transition metal,

[0149] A and B can both independently be C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0150] T 402 It may be a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、-C(Q 411 )=or=C=,

[0151] R 402 To R 409 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkyl, unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) or -P(=O)(Q 401 )(Q 402 ),

[0152] xc12 and xc18 may each independently be an integer from 0 to 3,

[0153] xc13, xc14, xc16, xc17 and xc19 may each independently be an integer from 0 to 4,

[0154] xc15 can be an integer from 0 to 2, and

[0155] R 10a As defined with reference to Equation 1, and Q 401 To Q 403 and Q 411 and Q 412 They may all be defined as in Formula 1.

[0156] In one or more embodiments, A and B can each independently be C 6 -C 60 For example, A and B can be independently a benzene group, a pentalene group, a naphthyl group, an azulene group, an indacene group, an acenaphthene group, a phenanthrenyl group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, A and B may be a phenyl group.

[0157] For example, M may be iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm). For example, M may be Pt.

[0158] In one or more embodiments, R 403 and R 407 To R 409 can be independently hydrogen, deuterium or C 1 -C 20 alkyl.

[0159] In one or more embodiments, the compound represented by Formula 1 may include one selected from the following compounds (ie, in one or more embodiments, Formula 1 may include one selected from the following compounds or may be represented by one selected from the following compounds):

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166] Wherein, in the aforementioned compound, M may be Pt. In one or more embodiments of the aforementioned compound, "D 5 ” means that there are five deuterium atoms substituted.

[0167] An electronic device according to another aspect may include the light emitting device.

[0168] In one or more embodiments, the electronic device may further include a thin film transistor,

[0169] The thin film transistor may include a source electrode and a drain electrode, and

[0170] The first electrode of the light emitting device may be electrically connected to one of a source electrode and a drain electrode of the thin film transistor.

[0171] As used herein, the term "intermediate layer" refers to a single layer, each layer, any layer and / or all layers between a first electrode and a second electrode of a light emitting device.

[0172] Figure 1 Description

[0173] Figure 1 is a schematic cross-sectional view of a light emitting device 10 according to one or more embodiments. The light emitting device 10 includes a first electrode 110 , an intermediate layer 130 , and a second electrode 150 .

[0174] In the following, reference will be made to Figure 1 A structure of a light emitting device 10 and a method of manufacturing the light emitting device 10 according to one or more embodiments are described.

[0175] First electrode 110

[0176] exist Figure 1 In the embodiment, a substrate may be additionally arranged below the first electrode 110 or on the second electrode 150. In one or more embodiments, a glass substrate or a plastic substrate may be used as the substrate. In one or more embodiments, the substrate may be a flexible substrate and may include a plastic having excellent or suitable heat resistance and durability (such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof).

[0177] The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that facilitates hole injection.

[0178] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, when the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0179] The first electrode 110 may have a single-layer structure including (eg, consisting of) a single layer or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0180] Middle layer 130

[0181] The intermediate layer 130 may be disposed on the first electrode 110. The intermediate layer 130 may include an emission layer.

[0182] The intermediate layer 130 may further include a hole transport region disposed between the first electrode 110 and the emission layer and an electron transport region disposed between the emission layer and the second electrode 150 .

[0183] In addition to one or more suitable organic materials, the intermediate layer 130 may further include a metal-containing compound such as an organometallic compound and / or an inorganic material such as quantum dots, etc.

[0184] In one or more embodiments, the intermediate layer 130 may include: i) two or more emission units sequentially stacked between the first electrode 110 and the second electrode 150; and ii) a charge generation layer located between the two or more emission units. When the intermediate layer 130 includes the two or more emission units and the charge generation layer, the light emitting device 10 may be a tandem light emitting device.

[0185] Hole transport region in the intermediate layer 130

[0186] The hole transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material; ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of materials different from each other; or iii) a multi-layer structure including a plurality of layers including a plurality of materials different from each other.

[0187] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.

[0188] For example, the hole transport region may have a multilayer structure including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure or a hole injection layer / hole transport layer / emission auxiliary layer structure, wherein the constituent layers of each structure are stacked sequentially from the first electrode 110.

[0189] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

[0190] Formula 201

[0191]

[0192] Formula 202

[0193]

[0194] Among them, in equation 201 and equation 202,

[0195] L 201 To L 204 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,

[0196] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or substituted with at least one R 10a C 1 -C 20 Alkylene, unsubstituted or substituted with at least one R 10a C 2 -C 20 Alkenylene, unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,

[0197] xa1 to xa4 may each independently be an integer from 0 to 5,

[0198] xa5 can be an integer from 1 to 10,

[0199] R 201 To R 204 and Q 201 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,

[0200] R 201 and R 202 may be optionally substituted via a single bond, unsubstituted or substituted with at least one R 10a C 1 -C 5 The alkylene group is either unsubstituted or substituted with at least one R 10a C 2 -C 5 Alkenylene groups are linked to each other to form an unsubstituted or substituted with at least one R 10a C 8 -C 60 Polycyclic groups (e.g., carbazole groups, etc.) (e.g., compound HT16, etc.),

[0201] R 203 and R 204 may be optionally substituted via a single bond, unsubstituted or substituted with at least one R 10a C 1 -C 5 The alkylene group is either unsubstituted or substituted with at least one R 10a C 2 -C 5 Alkenylene groups are linked to each other to form an unsubstituted or substituted with at least one R 10a C 8 -C 60 Polycyclic groups, and

[0202] na1 can be an integer from 1 to 4.

[0203] For example, each of Formula 201 and Formula 202 may include at least one of the groups represented by Formula CY201 to Formula CY217 (eg, at least one selected from the groups represented by Formula CY201 to Formula CY217):

[0204]

[0205] Among them, in formula CY201 to formula CY217, R 10b and R 10c Can be compared with reference R 10a Same as described, CY 201 To Ring CY 204 can be independently C 3 -C 20 Carbocyclic or C 1 -C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R 10a replace.

[0206] In one or more embodiments, ring CY in Formula CY201 to Formula CY217 201 To Ring CY 204 Each of them may independently be a benzene group, a naphthalene group, a phenanthrene group or an anthracene group.

[0207] In one or more embodiments, each of Formula 201 and Formula 202 may include at least one of the groups represented by Formula CY201 to Formula CY203 (eg, at least one selected from among the groups represented by Formula CY201 to Formula CY203).

[0208] In one or more embodiments, Formula 201 may include at least one of the groups represented by Formulas CY201 to CY203 (e.g., at least one selected from the groups represented by Formulas CY201 to CY203) and at least one of the groups represented by Formulas CY204 to CY217 (e.g., at least one selected from the groups represented by Formulas CY204 to CY217).

[0209] In one or more embodiments, in Formula 201, xa1 may be 1, R 201 may be one of the groups represented by Formula CY201 to Formula CY203 (for example, one selected from the groups represented by Formula CY201 to Formula CY203), xa2 may be 0, and R 202 It may be one of the groups represented by Formula CY204 to Formula CY207 (for example, one selected from the groups represented by Formula CY204 to Formula CY207).

[0210] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) the groups represented by Formula CY201 to Formula CY203.

[0211] In one or more embodiments, each of Formula 201 and Formula 202 may not include (e.g., may exclude) the groups represented by Formulas CY201 to CY203, and may include at least one of the groups represented by Formulas CY204 to CY217 (e.g., at least one selected from the groups represented by Formulas CY204 to CY217).

[0212] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) the groups represented by Formula CY201 to Formula CY217.

[0213] For example, the hole transport region may include: at least one selected from compound HT1 to compound HT46; m-MTDATA; TDATA; 2-TNATA; NPB (NPD); β-NPB; TPD; spiro-TPD; spiro-NPB; methylated NPB; TAPC; HMTPD; 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA); polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA); poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS); polyaniline / camphorsulfonic acid (PANI / CSA); polyaniline / poly(4-styrenesulfonate) (PANI / PSS); or any combination thereof:

[0214]

[0215]

[0216]

[0217]

[0218]

[0219] The thickness of the hole transport region can be about to about (For example, about to about ). When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about to about (For example, about to about ), and the thickness of the hole transport layer can be in the range of about to about (For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.

[0220] The emission auxiliary layer can improve the luminous efficiency by compensating the optical resonance distance according to the wavelength of the light emitted from the emission layer, and the electron blocking layer can block or reduce the leakage of electrons from the emission layer to the hole transport region. The material that can be included in the hole transport region can be included in the emission auxiliary layer and the electron blocking layer.

[0221] p-dopant

[0222] In addition to the materials described herein, the hole transport region may also include a charge generating material for improving the conductive properties. The charge generating material may be dispersed in the hole transport region uniformly or non-uniformly (e.g., in the form of a single layer including the charge generating material (e.g., in the form of a single layer consisting of the charge generating material)).

[0223] The charge generating material may be, for example, a p-dopant.

[0224] For example, the p-dopant can have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 electron volts (eV) or less.

[0225] In one or more embodiments, the p-dopant may include a quinone derivative, a cyano-containing compound, a compound including the element EL1 and the element EL2, or any combination thereof.

[0226] Examples of quinone derivatives may include TCNQ and / or F 4 -TCNQ, etc.

[0227] Examples of cyano-containing compounds may include HAT-CN and / or a compound represented by Formula 221, etc.:

[0228]

[0229] Formula 221

[0230]

[0231] Among them, in formula 221,

[0232] R 221 To R 223 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60a heterocyclic group, and

[0233] R 221 To R 223 At least one of them may be independently C substituted with the following groups 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group: cyano; -F; -Cl; -Br; -I; C substituted with cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof.

[0234] In the compound including the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or any combination thereof, and the element EL2 may be a nonmetal, a metalloid, or any combination thereof.

[0235] Examples of metals may include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), and / or cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), and / or barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), etc.); ), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag) and / or gold (Au), etc.); late transition metals (e.g., zinc (Zn), indium (In) and / or tin (Sn), etc.); and / or lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb) and / or lutetium (Lu), etc.); etc.

[0236] Examples of metalloids may include silicon (Si), antimony (Sb), and / or tellurium (Te), among others.

[0237] Examples of non-metal may include oxygen (O) and / or halogen (eg, F, Cl, Br, and / or I, etc.), and the like.

[0238] For example, the compound including element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide and / or a metal iodide, etc.), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide and / or a metalloid iodide, etc.), a metal telluride, or any combination thereof.

[0239] Examples of metal oxides may include tungsten oxide (eg, WO, W 2 O 3 , WO 2 , WO 3 and / or W 2 O 5 etc.), vanadium oxide (e.g., VO, V 2 O 3 , VO 2 and / or V 2 O 5 etc.), molybdenum oxides (e.g., MoO, Mo 2 O 3、 MoO 2 、MoO 3 and / or Mo 2 O 5 etc.) and / or rhenium oxide (e.g., ReO 3 etc.

[0240] Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and / or lanthanide metal halides, among others.

[0241] Examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and / or CsI, among others.

[0242] Examples of alkaline earth metal halides may include BeF 2 MgF 2 , CaF 2 , SrF 2 , BaF 2 、BeCl 2 MgCl 2 , CaCl 2 、SrCl 2 、BaCl 2 ,BeBr 2 MgBr 2 , CaBr 2 , SrBr 2 ,BaBr 2,BeI 2 MgI 2 ,CaI 2 , SrI 2 and / or BaI 2 wait.

[0243] Examples of transition metal halides may include titanium halides (eg, TiF 4 、TiCl 4 、TiBr 4 and / or TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 and / or ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 and / or HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3 , VBr 3 and / or VI 3 etc.), niobium halides (e.g., NbF 3 、NbCl 3 , NbBr 3 and / or NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 and / or TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 and / or CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 and / or MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 and / or WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2 and / or MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl 2 , TcBr 2 and / or TcI2 etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 and / or ReI 2 etc.), ferrous halides (e.g., FeF 2 、FeCl 2 , FeBr 2 and / or FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 and / or RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 and / or OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 and / or CoI 2 etc.), rhodium halides (e.g., RhF 2 , RhCl 2 , RhBr 2 and / or RhI 2 etc.), iridium halides (e.g., IrF 2 、IrCl 2 ,IrBr 2 and / or IrI 2 etc.), nickel halides (e.g., NiF 2 、NiCl 2 、NiBr 2 and / or NiI 2 etc.), palladium halides (e.g., PdF 2 , PdCl 2 , PdBr 2 and / or PdI 2 etc.), platinum halides (e.g., PtF 2 、PtCl 2 , PtBr 2 and / or PtI 2 etc.), cuprous halides (e.g., CuF, CuCl, CuBr and / or CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr and / or AgI, etc.) and / or gold halides (e.g., AuF, AuCl, AuBr and / or AuI, etc.), etc.

[0244] Examples of late transition metal halides may include zinc halides (e.g., ZnF 2 、ZnCl 2、ZnBr 2 and / or ZnI 2 etc.), indium halides (e.g., InI 3 etc.) and / or tin halides (e.g., SnI 2 etc.

[0245] Examples of lanthanide metal halides may include YbF, YbF 2 , YbF 3 、SmF 3 、YbCl、YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3 and / or SmI 3 wait.

[0246] Examples of metalloid halides may include antimony halides (eg, SbCl 5 etc.

[0247] Examples of metal tellurides may include alkali metal tellurides (eg, Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te and / or Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe and / or BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe and / or Au 2Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.) and / or lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe and / or LuTe, etc.), etc.

[0248] Emission layer in the middle layer 130

[0249] When the light emitting device 10 is a full-color light emitting device, the emission layer can be patterned into a red emission layer, a green emission layer and / or a blue emission layer according to the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer and a blue emission layer to emit white light, wherein the two or more layers are in contact with each other or separated from each other. In one or more embodiments, the emission layer may include two or more materials of a red light emitting material, a green light emitting material and a blue light emitting material to emit white light, wherein the two or more materials are mixed with each other in a single layer.

[0250] In one or more embodiments, the emission layer may include a host and a dopant. For example, the dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

[0251] The amount of the dopant in the emission layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.

[0252] In one or more embodiments, the emissive layer may include quantum dots.

[0253] In one or more embodiments, the emissive layer may include a delayed fluorescent material. For example, the delayed fluorescent material may act as a host or a dopant in the emissive layer.

[0254] The thickness of the emission layer can be about to about (For example, about to about When the thickness of the emission layer is within the described range, excellent or suitable light emitting characteristics can be obtained without significantly increasing the driving voltage.

[0255] main body

[0256] In one or more embodiments, the host may include a compound represented by Formula 301:

[0257] Formula 301

[0258] [Ar 301 ] xb11 -[(L 301 )xb1 -R 301 ] xb21 ,

[0259] Wherein, in Formula 301,

[0260] Ar 301 and L 301 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,

[0261] xb11 can be 1, 2 or 3,

[0262] xb1 can be an integer from 0 to 5.

[0263] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),

[0264] xb21 can be an integer from 1 to 5, and

[0265] Q 301 To Q 303 Can be compared with reference Q 1 Same as described.

[0266] For example, when xb11 in Formula 301 is 2 or greater, two or more Ar 301 can be connected to each other via a single bond.

[0267] In one or more embodiments, the host may include at least one selected from the compound represented by Formula 301-1, the compound represented by Formula 301-2, and any combination thereof:

[0268] Formula 301-1

[0269]

[0270] Formula 301-2

[0271]

[0272] Among them, in Formula 301-1 and Formula 301-2,

[0273] Ring A 301 To Ring A 304 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,

[0274] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),

[0275] xb22 and xb23 can each independently be 0, 1 or 2,

[0276] L 301 , xb1 and R 301 may all be the same as described herein,

[0277] L 302 To L 304 can be independently compared with the reference L301 Same as described,

[0278] xb2 to xb4 may each independently be the same as described with reference to xb1, and

[0279] R 302 To R 305 and R 311 To R 314 Can be compared with reference R 301 Same as described.

[0280] In one or more embodiments, the host can include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. For example, the host can include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.

[0281] In one or more embodiments, the host may include: at least one selected from Compound H1 to Compound H128; 9,10-di(2-naphthyl)anthracene (ADN); 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN); 9,10-di(2-naphthyl)-2-tert-butylanthracene (TBADN); 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP); 1,3-di(9-carbazolyl)benzene (mCP); 1,3,5-tri(carbazolyl-9-yl)benzene (TCP); or any combination thereof:

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288] Phosphorescent dopants

[0289] The phosphorescent dopant may include the compound of Formula 1 according to one or more embodiments.

[0290] Fluorescent dopants

[0291] The fluorescent dopant may include an amine-containing compound, a styrene-containing compound, or any combination thereof.

[0292] For example, the fluorescent dopant may include a compound represented by Formula 501:

[0293] Formula 501

[0294]

[0295] Wherein, in Formula 501,

[0296] Ar 501 , L 501 To L 503 , R 501 and R 502 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,

[0297] xd1 to xd3 may each independently be 0, 1, 2 or 3, and

[0298] xd4 can be 1, 2, 3, 4, 5 or 6.

[0299] In one or more embodiments, Ar in Formula 501 501 It may be a condensed ring group in which three or more monocyclic groups are condensed together (for example, anthracene group, groups and / or pyrene groups).

[0300] In one or more embodiments, xd4 in equation 501 may be 2.

[0301] In one or more embodiments, the fluorescent dopant may include: at least one of compounds FD1 to FD37; DPVBi; DPAVBi; or any combination thereof:

[0302]

[0303]

[0304]

[0305] Delayed fluorescence material

[0306] The emitting layer may include a delayed fluorescent material.

[0307] In the specification, the delayed fluorescent material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.

[0308] The delayed fluorescent material included in the emission layer may serve as a host or a dopant according to the types or kinds of other materials included in the emission layer.

[0309] In one or more embodiments, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be at least 0 eV but not greater than 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the described range, up-conversion from the triplet state of the delayed fluorescent material to the singlet state may effectively occur, and thus, the light emitting device 10 may have improved luminous efficiency.

[0310] For example, the delayed fluorescent material may include: i) at least one electron donor (eg, a π-electron-rich C 3 -C 60 a cyclic group, such as a carbazole group, etc.) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group and / or a π-electron-poor nitrogen-containing C 1 -C 60 and ii) materials including C in which two or more cyclic groups are condensed and share boron (B) 8 -C 60 Polycyclic materials.

[0311] Examples of the delayed fluorescent material may include at least one selected from Compound DF1 to Compound DF14:

[0312]

[0313]

[0314] Electron transport region in the intermediate layer 130

[0315] The electron transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material; ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of materials different from each other; or iii) a multi-layer structure including a plurality of layers including a plurality of materials different from each other.

[0316] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0317] For example, the electron transport region may have an electron transport layer / electron injection layer structure or a hole blocking layer / electron transport layer / electron injection layer structure in which constituent layers of each structure are sequentially stacked from the emission layer.

[0318] The electron transport region (eg, a hole blocking layer or an electron transport layer in the electron transport region) may include a nitrogen-containing C1 -C 60 Metal-free compounds of ring bases.

[0319] For example, the electron transport region may include a compound represented by Formula 601:

[0320] Formula 601

[0321] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ,

[0322] Wherein, in Formula 601,

[0323] Ar 601 and L 601 may be independently unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group,

[0324] xe11 can be 1, 2 or 3,

[0325] xe1 can be 0, 1, 2, 3, 4, or 5,

[0326] R 601 may be unsubstituted or substituted with at least one R 10a C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),

[0327] Q 601 To Q 603 Can be compared with reference Q 1 Same as described,

[0328] xe21 can be 1, 2, 3, 4, or 5, and

[0329] Ar601 , L 601 and R 601 At least one of them may be independently unsubstituted or substituted with at least one R 10a The π-electron-poor nitrogen-containing C 1 -C 60 Cyclic group.

[0330] In one or more embodiments, when xe11 in Formula 601 is 2 or greater, two or more Ar 601 can be connected to each other via a single bond.

[0331] In one or more embodiments, Ar in Formula 601 601 may be unsubstituted or substituted with at least one R 10a anthracene group.

[0332] In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:

[0333] Formula 601-1

[0334]

[0335] Among them, in formula 601-1,

[0336] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), X 616 Can be N or C (R 616 ), and X 614 To X 616 At least one of may be N,

[0337] L 611 To L 613 Can be compared with reference L 601 Same as described,

[0338] xe611 to xe613 may all be the same as described with reference to xe1,

[0339] R 611 To R 613 Can be compared with reference R 601 Same as described, and

[0340] R 614 To R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1-C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a C 1 -C 60 Heterocyclic group.

[0341] For example, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 can all independently be 0, 1 or 2.

[0342] The electron transport region may include: at least one selected from compound ET1 to compound ET45; 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP); 4,7-diphenyl-1,10-phenanthroline (Bphen); Alq 3 ; BAlq; TAZ; NTAZ; or any combination thereof:

[0343]

[0344]

[0345]

[0346] The thickness of the electron transport region can be about to about (For example, about to about ). When the electron transport region includes a hole blocking layer, an electron transport layer, or any combination thereof, the thickness of the hole blocking layer may be about to about (For example, about to about ). The thickness of the electron transport layer can be in the range of about to about (For example, about to about When the thickness of the hole blocking layer and / or the electron transport layer is within the described range, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.

[0347] In addition to the materials described herein, the electron transport region (eg, an electron transport layer in the electron transport region) can also include a metal-containing material.

[0348] The metal-containing material can include alkali metal complex, alkaline earth metal complex or any combination thereof. The metal ion of the alkali metal complex can be Li ion, Na ion, K ion, Rb ion or Cs ion, and the metal ion of the alkaline earth metal complex can be Be ion, Mg ion, Ca ion, Sr ion or Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or alkaline earth metal complex can include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.

[0349] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) and / or compound ET-D2:

[0350]

[0351] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.

[0352] The electron injection layer may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material; ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of materials different from each other; or iii) a multi-layer structure including a plurality of layers including a plurality of materials different from each other.

[0353] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0354] Alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. Alkaline earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. Rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0355] The alkali metal-containing compound, alkaline earth metal-containing compound and rare earth metal-containing compound may be oxides, halides (eg, fluorides, chlorides, bromides and / or iodides, etc.) or tellurides of alkali metals, alkaline earth metals and rare earth metals, or any combination thereof.

[0356] The alkali metal-containing compound may include: alkali metal oxides (such as Li2 O, Cs 2 O and / or K 2 O, etc.); alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI, etc.); or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound or oxide (such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1) and / or Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1), etc.). The rare earth metal-containing compound may include YbF 3 , ScF 3 , Sc 2 O 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 , TbF 3 , YbI 3 , ScI 3 , TbI 3 or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include lanthanide metal tellurides. Examples of lanthanide metal tellurides are LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La 2 Te 3 , Ce 2 Te 3 , Pr 2 Te 3 , Nd 2 Te 3 , Pm 2 Te 3 , Sm 2 Te 3 , Eu 2 Te 3 , Gd 2 Te 3 , Tb 2 Te 3 , Dy 2 Te 3 , Ho 2 Te 3 , Er 2 Te 3 , Tm 2 Te 3 , Yb2 Te 3 and / or Lu 2 Te 3 wait.

[0357] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include: i) one selected from metal ions of alkali metals, alkaline earth metals and rare earth metals; and ii) a ligand bound to the metal ion (e.g., the selected metal ion), for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.

[0358] In one or more embodiments, the electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described herein (e.g., composed of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described herein). In one or more embodiments, the electron injection layer may also include an organic material (e.g., a compound represented by Formula 601).

[0359] In one or more embodiments, the electron injection layer may include: i) an alkali metal compound (e.g., an alkali metal halide); or ii) a) an alkali metal compound (e.g., an alkali metal halide) and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof (e.g., composed of i) an alkali metal compound (e.g., an alkali metal halide); or composed of ii) a) an alkali metal compound (e.g., an alkali metal halide) and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof). For example, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, and / or a LiF:Yb co-deposition layer, etc.

[0360] When the electron injection layer also includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex or any combination thereof can be uniformly or non-uniformly dispersed in a matrix including the organic material.

[0361] The thickness of the electron injection layer can be about to about (For example, about to about When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.

[0362] The second electrode 150

[0363] The second electrode 150 is disposed on the intermediate layer 130 having the structure as described herein. The second electrode 150 may be a cathode as an electron injection electrode, and a metal, an alloy, a conductive compound, or any combination thereof each having a low work function may be used as a material for forming the second electrode 150.

[0364] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0365] The second electrode 150 may have a single-layer structure or a multi-layer structure including a plurality of layers.

[0366] Covering

[0367] The first cover layer may be arranged outside the first electrode 110 (and, for example, the first cover layer may be arranged on the first electrode 110), and / or the second cover layer may be arranged outside the second electrode 150 (and, for example, the second cover layer may be arranged on the second electrode 150). In detail, the light emitting device 10 may have: a structure in which the first cover layer, the first electrode 110, the intermediate layer 130, and the second electrode 150 are sequentially stacked in the stated order; a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150, and the second cover layer are sequentially stacked in the stated order; or a structure in which the first cover layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second cover layer are sequentially stacked in the stated order.

[0368] Light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 may be extracted toward the outside through the first electrode 110 as a semi-transmissive electrode or a transmissive electrode and the first cover layer. Light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 may be extracted toward the outside through the second electrode 150 as a semi-transmissive electrode or a transmissive electrode and the second cover layer.

[0369] The first and second covering layers may increase external emission efficiency according to the principle of constructive interference. Therefore, the light extraction efficiency of the light emitting device 10 may be increased, so that the light emitting efficiency of the light emitting device 10 may be improved.

[0370] Each of the first cover layer and the second cover layer may include a material having a refractive index (at 589 nm) of 1.6 or more.

[0371] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.

[0372] At least one selected from the first cover layer and the second cover layer can independently include carbocyclic compounds, heterocyclic compounds, amine-containing compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes or any combination thereof. Carbocyclic compounds, heterocyclic compounds and amine-containing compounds can be optionally substituted with substituents including O, N, S, Se, Si, F, Cl, Br, I or any combination thereof. In one or more embodiments, at least one selected from the first cover layer and the second cover layer can independently include amine-containing compounds.

[0373] In one or more embodiments, at least one selected from among the first cover layer and the second cover layer may each independently include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof.

[0374] In one or more embodiments, at least one selected from the first cover layer and the second cover layer may each independently include at least one selected from compounds HT28 to HT33, at least one selected from compounds CP1 to CP6, β-NPB, and / or any combination thereof:

[0375]

[0376] Electronic Devices

[0377] The light emitting device may be included in one or more suitable electronic devices. For example, the electronic device including the light emitting device may be a light emitting device and / or an authentication device, etc.

[0378] In addition to the light emitting device, the electronic device (e.g., light emitting device) may further include: i) a color filter; ii) a color conversion layer; or iii) a color filter and a color conversion layer. The color filter and / or the color conversion layer may be arranged along at least one traveling direction of the light emitted from the light emitting device. For example, the light emitted from the light emitting device may be blue light or white light. The details about the light emitting device may be the same as described herein.

[0379] The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixel regions, the color filter may include a plurality of color filter regions respectively corresponding to the sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the sub-pixel regions.

[0380] A pixel defining layer may be disposed between the sub-pixel regions to define each of the sub-pixel regions.

[0381] The color filter may further include a plurality of color filter regions and a light shielding pattern disposed between the color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light shielding pattern disposed between the color conversion regions.

[0382] A plurality of color filter regions (or a plurality of color conversion regions) may include a first region emitting a first color light, a second region emitting a second color light, and / or a third region emitting a third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, a plurality of color filter regions (or a plurality of color conversion regions) may include quantum dots. In detail, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include (e.g., may exclude) quantum dots. Details about quantum dots may be the same as described herein. The first region, the second region, and / or the third region may each further include a scatterer.

[0383] For example, the light emitting device may emit a first light, the first region may absorb the first light to emit a first first color light, the second region may absorb the first light to emit a second first color light, and the third region may absorb the first light to emit a third first color light. In this regard, the first first color light, the second first color light, and the third first color light may have different maximum emission wavelengths. In detail, the first light may be blue light, the first first color light may be red light, the second first color light may be green light, and the third first color light may be blue light.

[0384] In addition to the light emitting device as described herein, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light emitting device.

[0385] The thin film transistor may further include a gate electrode and / or a gate insulating film, etc.

[0386] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor, etc.

[0387] The electronic device may further include a sealing portion for sealing the light emitting device. The sealing portion may be arranged between the color filter and / or the color conversion layer and the light emitting device. The sealing portion extracts light from the light emitting device to the outside and concurrently (e.g., simultaneously) prevents ambient air and moisture from penetrating into the light emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.

[0388] Depending on the purpose of the electronic device, in addition to the color filter and / or the color conversion layer, various functional layers may be additionally arranged on the sealing portion. Examples of the functional layer may include a touch screen layer and / or a polarizing layer, etc. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual by utilizing biometric information of a living organism (e.g., a fingertip and / or a pupil, etc.).

[0389] In addition to the light emitting device as described herein, the authentication device may also include a biometric information collector.

[0390] The electronic device can be applied to one or more suitable displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notepads, electronic dictionaries, electronic game consoles, medical instruments (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasound diagnostic devices, or endoscope displays), fish finders, one or more suitable measuring instruments, meters (e.g., meters for vehicles, aircraft, and ships), and / or projectors, etc.

[0391] Electronic devices

[0392] The light emitting device may be included in one or more suitable electronic devices.

[0393] For example, the electronic device including the light emitting device can be at least one selected from a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and / or a light for signaling, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a phone (e.g., a mobile phone or a tablet phone), a tablet computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality or augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater or stadium screen, a light therapy device, a sign, and a combination thereof.

[0394] The light emitting device may have excellent or appropriate light emitting efficiency and a long lifespan, and thus an electronic device including the light emitting device may have characteristics such as high brightness, high resolution, and low power consumption.

[0395] Figure 2 and Figure 3 Description

[0396] Figure 2 is a cross-sectional view of an electronic device 180 according to one or more embodiments.

[0397] Figure 2 The electronic device 180 includes a substrate 100, a thin film transistor (TFT), a light emitting device, and a packaging portion 300 sealing the light emitting device.

[0398] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 may prevent or reduce impurities from penetrating through the substrate 100 and may provide a flat surface on the substrate 100.

[0399] The TFT may be disposed on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

[0400] The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.

[0401] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be disposed on the active layer 220 , and the gate electrode 240 may be disposed on the gate insulating film 230 .

[0402] An interlayer insulating film 250 may be disposed on the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to be insulated from each other.

[0403] The source electrode 260 and the drain electrode 270 may be disposed on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source and drain regions of the active layer 220, and the source electrode 260 and the drain electrode 270 may be disposed to contact the exposed portions of the source and drain regions of the active layer 220.

[0404] The TFT may be electrically connected to the light emitting device to drive the light emitting device, and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light emitting device may be disposed on the passivation layer 280. The light emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0405] The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 may be disposed to expose a portion of the drain electrode 270 without completely covering the drain electrode 270, and the first electrode 110 may be disposed to be connected to the exposed portion of the drain electrode 270.

[0406] A pixel defining layer 290 including an insulating material may be disposed on the first electrode 110. The pixel defining layer 290 may expose a specific region of the first electrode 110, and the intermediate layer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide-based organic film or a polyacrylic organic film. In some embodiments, at least some layers of the intermediate layer 130 may extend beyond the upper portion of the pixel defining layer 290 to be arranged in the form of a common layer.

[0407] The second electrode 150 may be disposed on the intermediate layer 130, and the capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

[0408] The encapsulation part 300 may be disposed on the cover layer 170. The encapsulation part 300 may be disposed on the light emitting device to protect the light emitting device from moisture and / or oxygen. The encapsulation part 300 may include: an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide or any combination thereof; organic films including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resins (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of inorganic films and organic films.

[0409] Figure 3 is a cross-sectional view of an electronic device 190 according to another embodiment.

[0410] In addition to the light shielding pattern 500 and the functional region 400 being additionally arranged on the encapsulation portion 300, Figure 3 The electronic device 190 and Figure 2The functional area 400 may be: i) a color filter area; ii) a color conversion area; or iii) a combination of a color filter area and a color conversion area. In one or more embodiments, the functional area 400 may be: i) a color filter area; ii) a color conversion area; or iii) a combination of a color filter area and a color conversion area. Figure 3 The light emitting device in the electronic device 190 may be a series light emitting device.

[0411] Figure 4 Description

[0412] Figure 4 is a schematic perspective view of an electronic device 1 including a light-emitting device according to one or more embodiments. As a device for displaying moving images or still images, the electronic device 1 may be a portable electronic device such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook, an electronic book, a portable multimedia player (PMP), a navigator or an ultra-mobile PC (UMPC), and one or more suitable products such as a television, a laptop computer, a monitor, a billboard or an Internet of Things (IOT) device. The electronic device 1 may be such a product as described herein or a part thereof. In some embodiments, the electronic device 1 may be a wearable device or a part of a wearable device such as a smart watch, a watch phone, a glasses-type or similar display or a head-mounted display (HMD). However, the embodiments are not limited thereto. For example, the electronic device 1 may include a dashboard of a vehicle, a central information display (CID) on a central instrument panel or dashboard of a vehicle, an interior mirror display replacing a side mirror of a vehicle, an entertainment display arranged for a rear seat of a vehicle or arranged on the back of a front seat, a head-up display (HUD) mounted on the front of the vehicle or projected on the front window glass, or a computer-generated hologram augmented reality head-up display (CGH AR HUD). For ease of explanation, Figure 4 A case is shown in which the electronic device 1 is a smartphone.

[0413] The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device may realize an image through an array of a plurality of pixels two-dimensionally arranged in the display area DA.

[0414] The non-display area NDA is an area where no image is displayed, and may be around the display area DA (e.g., completely surround the display area DA). A driver for providing an electrical signal or power to a display device arranged in the display area DA may be arranged in the non-display area NDA. A pad (or "pad"), which is an area to which an electronic component or a printed circuit board can be electrically connected, may be arranged in the non-display area NDA.

[0415] In the electronic device 1, the length in the x-axis direction (or referred to as the "x direction") and the length in the y-axis direction (or referred to as the "y direction") may be different from each other, and the z-axis direction (or referred to as the "z direction") may be the thickness direction of the electronic device 1. In one or more embodiments, as Figure 4 As shown in , the length in the x-axis direction may be shorter than the length in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be identical to the length in the y-axis direction. In one or more embodiments, the length in the x-axis direction may be longer than the length in the y-axis direction.

[0416] Figure 5 and FIG. 6A to FIG. 6C Description

[0417] Figure 5 is a schematic diagram of the exterior of a vehicle 1000 as an electronic device including a light emitting device according to one or more embodiments. FIG. 6A to FIG. 6C 1 and 2 are schematic diagrams of the interior of a vehicle 1000 according to one or more embodiments.

[0418] Reference Figure 5 , Fig. 6A , Figure 6B and Figure 6C The vehicle 1000 may refer to one or more suitable devices for moving an object to be transported (such as a person, an object, or an animal) from a starting point to a destination point. The vehicle 1000 may include a vehicle traveling on a road or track, a ship moving on an ocean or a river, and / or an airplane flying in the sky using the action of air, etc.

[0419] The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a set or predetermined direction according to the rotation of at least one wheel. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, an engineering machine, a two-wheeled vehicle, a prime mover device, a bicycle, and a train traveling on a track.

[0420] The vehicle 1000 may include a body having an interior and an exterior and a chassis in which mechanical equipment required for driving is installed as other parts other than the body. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and / or pillars provided at the boundaries between doors, etc. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension device, a transmission device, a fuel device, front and rear wheels, and / or left and right wheels, etc.

[0421] The vehicle 1000 may include side window glasses 1100 , a front window glass 1200 , side view mirrors 1300 , a cluster 1400 , a central instrument panel 1500 , a passenger seat instrument panel 1600 , and a display device 2 .

[0422] The side window glass 1100 and the front window glass 1200 may be separated by pillars disposed between the side window glass 1100 and the front window glass 1200 .

[0423] The side window glass 1100 may be mounted on the side of the vehicle 1000. In one or more embodiments, the side window glass 1100 may be mounted on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided, and the plurality of side window glasses 1100 may face each other. In one or more embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In one or more embodiments, the first side window glass 1110 may be arranged adjacent to the cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.

[0424] In one or more embodiments, the side window glass 1100 may be spaced apart and / or separated from each other in the x-direction or in a direction opposite to the x-direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart and / or separated from each other in the x-direction or in a direction opposite to the x-direction. In other words, the imaginary straight line L connecting the side window glass 1100 may extend in the x-direction or in a direction opposite to the x-direction. For example, the imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend in the x-direction or in a direction opposite to the x-direction.

[0425] The front window glass 1200 may be installed in the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.

[0426] The side view mirror 1300 can provide a rear view of the vehicle 1000. The side view mirror 1300 can be mounted on the exterior of the vehicle body. In one or more embodiments, a plurality of side view mirrors 1300 can be provided. Any one of the plurality of side view mirrors 1300 can be arranged outside the first side window glass 1110. Another one of the plurality of side view mirrors 1300 can be arranged outside the second side window glass 1120.

[0427] Cluster 1400 may be arranged in front of the steering wheel. Cluster 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, an automatic shift selector indicator light, a door open warning light, an engine oil warning light, and / or a low fuel warning light.

[0428] The central instrument panel 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and a heater of a seat are arranged. The central instrument panel 1500 may be arranged on one side of the cluster 1400 .

[0429] The passenger seat instrument panel 1600 may be spaced apart and / or separated from the cluster 1400 and the central instrument panel 1500 may be disposed between the passenger seat instrument panel 1600 and the cluster 1400. In one or more embodiments, the cluster 1400 may be disposed to correspond to the driver's seat, and the passenger seat instrument panel 1600 may be disposed to correspond to the passenger seat. In one or more embodiments, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.

[0430] In one or more embodiments, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In one or more embodiments, the display device 2 may be arranged between side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the cluster 1400, the central instrument panel 1500, and the passenger seat instrument panel 1600.

[0431] The display device 2 may include an organic light-emitting display device, an inorganic light-emitting display device, and / or a quantum dot display device, etc. Hereinafter, as a display device 2 according to one or more embodiments, an organic light-emitting display device including a light-emitting device according to the disclosure will be described as an example, but one or more suitable types (kinds) of display devices as described herein may be utilized in the disclosed embodiments.

[0432] Reference Fig. 6A , the display device 2 may be arranged on the central instrument panel 1500. In one or more embodiments, the display device 2 may display navigation information. In one or more embodiments, the display device 2 may display audio, video, or information about vehicle settings.

[0433] Reference Figure 6B , the display device 2 may be arranged on the cluster 1400. When the display device 2 is arranged on the cluster 1400, the cluster 1400 may display driving information and the like through the display device 2. For example, the cluster 1400 may be implemented digitally. The digital cluster 1400 may display vehicle information and driving information as images. For example, the pointer and instrument of the tachometer and one or more suitable warning light icons may be displayed through digital signals.

[0434] Reference Figure 6C, the display device 2 may be arranged on the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or arranged on the passenger seat instrument panel 1600. In one or more embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display an image related to the information displayed on the cluster 1400 and / or the information displayed on the central instrument panel 1500. In one or more embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the cluster 1400 and / or the information displayed on the central instrument panel 1500.

[0435] Manufacturing method

[0436] The layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region can be formed in a specific region by utilizing one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and / or laser induced thermal imaging.

[0437] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be within a range of about 100° C. to about 500° C. ... -8 To about 10 -3 Torr range and at about 0.01 angstroms per second ( / second) to about The vacuum deposition is performed at a deposition rate in the range of 200 Å / s.

[0438] Definition of terms

[0439] As used herein, the term “C 3 -C 60 "Carbocyclyl" refers to a cyclic group consisting of only carbon as a ring atom and having 3 to 60 carbon atoms, and as used herein, the term "C 1 -C 60 The term "heterocyclic group" refers to a ring group having 1 to 60 carbon atoms and having a hetero atom as a ring-forming atom in addition to carbon. 3 -C 60 Carbocyclic and C 1 -C 60 The heterocyclic groups may be monocyclic groups consisting of one ring or polycyclic groups in which two or more rings are condensed with each other. 1 -C 60 The number of ring-forming atoms of the heterocyclic group can be 3 to 61.

[0440] As used herein, the term "cyclic group" may include C3 -C 60 Carbocyclic and C 1 -C 60 Both heterocyclic groups (for example, both C 3 -C 60 Carbocyclic and C 1 -C 60 heterocyclic group).

[0441] As used herein, the term "π-electron-rich C 3 -C 60 "Cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and not including *-N=*' as a ring-forming part, and as used herein, the term "π-electron-poor nitrogen-containing C 1 -C 60 The term "cyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-forming part.

[0442] For example,

[0443] C 3 -C 60 The carbocyclic group may be: i) a group T1; or ii) a condensed ring group in which two or more groups T1 are condensed with each other (for example, a cyclopentadiene group, an adamantane group, a norbornane group, a phenyl group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthene group, a phenanthrenyl group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, a benzophenone group, a fluorene group, a spirobifluorene group, a benzofluorene group, an indenophenanthrene group or an indenoanthracene group),

[0444] C 1 -C 60The heterocyclic group may be: i) a group T2; ii) a condensed ring group in which two or more groups T2 are condensed with each other; or iii) a condensed ring group in which at least one group T2 and at least one group T1 are condensed with each other (for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzindole group, a naphthoindole group, an isoindole group, a benzisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, benzofuran group, carbazole group, dibenzosilole group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolecarbazole group, benzofuranocarbazole group, benzothiophenocarbazole group, benzosiloleocarbazole group, benzoindolecarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthosilole group, benzofuranodibenzofuran group, benzofuranodibenzothiophene group group, benzothienodibenzothiophene group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group azoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group and / or an azadibenzofuran group, etc.),

[0445] Pi-electron-rich C 3 -C 60 The cyclic group may be: i) a group T1; ii) a condensed cyclic group in which two or more groups T1 are condensed with each other; iii) a group T3; iv) a condensed cyclic group in which two or more groups T3 are condensed with each other; or v) a condensed cyclic group in which at least one group T3 and at least one group T1 are condensed with each other (e.g., C 3 -C 60a carbocyclic group, a 1H-pyrrole group, a thiol group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzothiol group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzothiol group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a benzothiololcarbazole group, a benzoindolecarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthothiol group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group and / or a benzothiophenodibenzothiophene group, etc.),

[0446] π-electron-poor nitrogen-containing C 1 -C 60 The cyclic group may be: i) a group T4; ii) a condensed cyclic group in which two or more groups T4 are condensed with each other; iii) a condensed cyclic group in which at least one group T4 and at least one group T1 are condensed with each other; iv) a condensed cyclic group in which at least one group T4 and at least one group T3 are condensed with each other; or v) a condensed cyclic group in which at least one group T4, at least one group T1 and at least one group T3 are condensed with each other (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzooxadiazole group azole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group and / or azadibenzofuran group etc.),

[0447] The group T1 can be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group or a phenyl group,

[0448] The group T2 can be a furan group, a thiophene group, a 1H-pyrrole group, a thiol group, a borocyclopentadiene group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiol group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidinyl group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group or a dihydropyridazine group,

[0449] The group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a thiole group or a borole group, and

[0450] The group T4 can be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiazole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or a tetrazine group.

[0451] As used herein, the term "cyclic group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic, π-electron-rich C 3 -C 60 Ring-based or π-electron-poor nitrogen-containing C 1 -C 60 The term "cyclic group" refers to a group condensed with any cyclic group, a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group and / or a tetravalent group, etc.) according to the structure of the formula for which the corresponding term is used. For example, a "phenyl group" may be a benzo group, a phenyl group and / or a phenylene group, etc., which can be easily understood by a person of ordinary skill in the art based on the structure of the formula including the "phenyl group".

[0452] Depending on the context, a divalent group may refer to or be a multivalent group (eg, trivalent, tetravalent, etc., not just divalent), such as a structure of the formula associated with the term being used.

[0453] Unit Price C 3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 Examples of heterocyclic groups may include C 3 -C 10 Cycloalkyl, C 1-C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group. 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 Examples of heterocyclic groups may include C 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C 3 -C 10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 heteroarylene groups, divalent non-aromatic condensed polycyclic groups and divalent non-aromatic condensed heteropolycyclic groups.

[0454] As used herein, the term “C 1 -C 60 The term “alkyl” refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl and / or tert-decyl, etc. As used herein, the term “C 1 -C 60 "Alkylene" refers to C 1 -C 60 An alkyl group is a divalent group having the same structure.

[0455] As used herein, the term “C 2 -C 60 "Alkenyl" refers to 2 -C 60 The term "C" refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, and examples thereof are ethenyl, propenyl and / or butenyl, etc. As used herein, the term "C 2 -C60 "Alkenylene" refers to C 2 -C 60 An alkenyl group is a divalent group having the same structure.

[0456] As used herein, the term “C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 The term "alkyl" refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminal of the alkyl group, and examples thereof are ethynyl and / or propynyl, etc. As used herein, the term "C 2 -C 60 "Alkynylidene" refers to a C 2 -C 60 Alkynyl is a divalent group having the same structure.

[0457] As used herein, the term “C 1 -C 60 "Alkoxy" refers to -OA 101 (Among them, A 101 C 1 -C 60 The invention further comprises a monovalent group represented by an alkyl group, and examples thereof are a methoxy group, an ethoxy group and / or an isopropoxy group and the like.

[0458] As used herein, the term “C 3 -C 10 The term "cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl and / or bicyclo[2.2.2]octyl, and the like. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl and / or bicyclo[2.2.2 3 -C 10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group is a divalent group having the same structure.

[0459] As used herein, the term “C 1 -C 10 "Heterocycloalkyl" refers to a monovalent ring group of 1 to 10 carbon atoms which includes at least one hetero atom as a ring-forming atom in addition to carbon atoms, and examples thereof are 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and / or tetrahydrothienyl, etc. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has a divalent group of the same structure.

[0460] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and examples thereof are cyclopentenyl, cyclohexenyl and / or cycloheptenyl, etc. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group is a divalent group having the same structure.

[0461] As used herein, the term “C 1 -C 10 The term "heterocycloalkenyl" refers to a monovalent cyclic group of 1 to 10 carbon atoms which contains at least one heteroatom as a ring-forming atom in addition to carbon atoms in its ring structure and has at least one double bond. 1 -C 10 Examples of heterocycloalkenyl groups are 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl and / or 2,3-dihydrothienyl, etc. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to a C 1 -C 10 The heterocycloalkenyl group is a divalent group having the same structure.

[0462] As used herein, the term “C 6 -C 60 "Aryl" refers to a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Examples of aryl groups are phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, heptaphenyl, tetraphenyl, peryl, hexyl, pentyl, rubidinyl, corynyl and / or ovaphenyl. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be condensed with each other.

[0463] As used herein, the term “C 1 -C 60"Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms which includes at least one heteroatom as a ring-forming atom in addition to carbon atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms which includes at least one heteroatom as a ring-forming atom in addition to carbon atoms. 1 -C 60 Examples of heteroaryl groups are pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl and / or naphthyridinyl, etc. When C 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene group includes two or more rings, the rings may be condensed with each other.

[0464] As used herein, the term "monovalent non-aromatic condensed polycyclic radical" refers to a monovalent group having two or more rings condensed to each other, only carbon atoms (e.g., having 8 to 60 carbon atoms) as ring atoms and no aromaticity in its entire molecular structure. Examples of monovalent non-aromatic condensed polycyclic radicals are indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl and / or indenoanthryl, etc. As used herein, the term "divalent non-aromatic condensed polycyclic radical" refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic radical.

[0465] As used herein, the term "monovalent non-aromatic condensed heteropolycyclic group" refers to a monovalent group having two or more rings condensed to each other, including at least one heteroatom as a ring-constituting atom in addition to carbon atoms (for example, having 1 to 60 carbon atoms), and having no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group are pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothiorolyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzo The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

[0466] As used herein, the term “C 6 -C 60 "Aryloxy" refers to -OA 102 (Among them, A 102 C 6 -C 60 aryl), and as used herein, the term "C 6 -C 60 "Arylthio" refers to -SA 103 (Among them, A 103 C 6 -C 60 aryl).

[0467] As used herein, the term "C 7 -C 60 "Arylalkyl" refers to -A 104 A 105 (Among them, A 104 C 1 -C 54 Alkylene, and A 105 C 6 -C 59 aryl), and as used herein the term "C2 -C 60 "Heteroarylalkyl" refers to -A 106 A 107 (Among them, A 106 C 1 -C 59 Alkylene, and A 107 C 1 -C 59 heteroaryl).

[0468] As used herein, the term “R 10a ” can be:

[0469] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0470] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl, C 2 -C 60 Heteroarylalkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy;

[0471] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl, C 2 -C 60 Heteroarylalkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl; or

[0472] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ).

[0473] In the manual, Q 1To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; or C 1 -C 60 Alkoxy; or

[0474] All are unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 C alkoxy, phenyl, biphenyl or any combination thereof 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroarylalkyl.

[0475] As used herein, the term "heteroatom" refers to any atom other than a carbon atom. Examples of heteroatoms are O, S, N, P, Si, B, Ge, Se, and any combination thereof.

[0476] The term "third row transition metal" as used herein includes hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt) and / or gold (Au), etc.

[0477] As used herein, "Ph" refers to phenyl; as used herein, "Me" refers to methyl; as used herein, "Et" refers to ethyl; as used herein, "tBu", "tert-Bu" or "Bu t ” refers to tert-butyl; and as used herein, the term “OMe” refers to methoxy.

[0478] As used herein, the term "biphenyl" refers to a "phenyl group substituted with a phenyl group". In other words, a "biphenyl group" may be a group having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.

[0479] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group". In other words, the "terphenyl group" may be a phenyl group substituted with a C 6 -C 60 Aryl C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.

[0480] The maximum number of carbon atoms in this substituent definition is only an example. 1 -C 60 The maximum number of carbons in an alkyl group, 60, is an example, and the definition of an alkyl group applies equally to C 1 -C 20 Alkyl. The same applies to the other cases.

[0481] Unless otherwise defined, * and *' as used herein refer to binding sites with adjacent atoms in the corresponding formula.

[0482] Terms such as "substantially," "about," and "approximately" are used as relative terms rather than terms of degree, and are intended to account for the inherent deviations in measured or calculated values ​​that one of ordinary skill in the art would recognize. They may include the stated value and an acceptable range of deviation determined by one of ordinary skill in the art, taking into account the limitations and errors associated with the measurement of a particular quantity. For example, "about" may refer to one or more standard deviations, or ±30%, ±20%, ±10%, or ±5% of the stated value.

[0483] The numerical ranges disclosed herein include and intend to disclose all subranges of the same numerical precision contained therein. For example, the range "1.0 to 10.0" includes all subranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Therefore, the applicant reserves the right to amend this specification (including the claims) to explicitly state any subranges contained within the ranges explicitly stated herein.

[0484] According to the embodiments of the present disclosure described herein, the light-emitting device, the light-emitting element and / or any other related device or component can be implemented using any suitable hardware, firmware (e.g., a dedicated integrated circuit), software, or a combination of software, firmware and hardware. For example, the various components of the light-emitting device and / or the light-emitting element can be formed on an integrated circuit (IC) chip or on a separate IC chip. In addition, the various components of the light-emitting device and / or the light-emitting element can be implemented on a flexible printed circuit film, a carrier package (TCP), a printed circuit board (PCB), or formed on a substrate. In addition, the various components of the light-emitting device and / or the light-emitting element can be processes or threads running on one or more processors in one or more computing devices, executing computer program instructions and interacting with other system components to perform the various functions described herein. The computer program instructions are stored in a memory, which can be implemented in a computing device using a standard memory device (such as a random access memory (RAM) as an example). The computer program instructions can also be stored in other non-temporary computer-readable media (such as a CD-ROM or a flash drive, etc. as an example). In addition, those skilled in the art should recognize that, without departing from the scope of the embodiments of the present disclosure, the functions of various computing devices may be combined or integrated into a single computing device, or the functions of a particular computing device may be distributed on one or more other computing devices.

[0485] Hereinafter, compounds and light emitting devices according to embodiments will be described in more detail with reference to examples. The phrase "using B instead of A" used when describing the following synthesis examples means using the same molar equivalent of B instead of the same molar equivalent of A.

[0486] Example

[0487] Synthesis of compounds

[0488] Synthesis of compound GD03

[0489]

[0490] 1. Synthesis of intermediate compound GD03-1

[0491] Mg (2.0 eq) was added to tetrahydrofuran (THF) (3.5 M) and 1,2-dibromoethane (75 M), and the resulting reaction mixture was stirred. A reactant obtained by dissolving 2-benzyl-5-fluoroisoindoline-1,3-dione (1.0 eq) in THF (0.5 M) was added thereto, and the reaction mixture was refluxed at 90 ° C. A reactant obtained by dissolving 1-bromo-2-chlorobenzene (1.2 eq) in THF (1.5 M) was added thereto, and the reaction mixture was refluxed for 3 hours and cooled at room temperature. NH 4Cl (0.6M) aqueous solution, and the reaction mixture was subjected to three extraction processes with ether and water to obtain an organic layer. The obtained organic layer was dried over anhydrous sodium sulfate, concentrated, and then recrystallized with hexane and acetone to synthesize the intermediate compound GD03-1 (yield 47%).

[0492] 2. Synthesis of intermediate compound GD03-2

[0493] The intermediate compound GD03-1 (1.0 eq), NaHCO 3 (1.2 eq) and N-bromosuccinimide (NBS) (1.2 eq) were dissolved in a 9:1 volume ratio of dioxane and H 2 O solution (0.25 M), and the resulting reaction mixture was stirred for 28 hours. The reaction mixture was concentrated and then recrystallized with hexane and ethyl acetate (AcOEt) to synthesize the intermediate compound GD03-2 (yield 78%).

[0494] 3. Synthesis of intermediate compound GD03-3

[0495] The intermediate compound GD03-2 (1.0 eq) was dissolved in methanol (MeOH), and a compound obtained by dissolving hydrazine hydrate (2.5 eq) in MeOH (0.4 M) was added thereto at 0° C. for 5 minutes. The resulting reaction mixture was stirred for 30 minutes, concentrated, dissolved in 1N HCl (1.5 M), then filtered, and the filtrate was washed with water and 1N HCl aqueous solution, and neutralized with KOH in an ice bath. Then, the precipitate was recovered, washed with water, and then dried to synthesize the intermediate compound GD03-3 (yield 46%).

[0496] 4. Synthesis of intermediate compound GD03-4

[0497] The intermediate compound GD03-3 (1.0 eq), 2-chloropyridine (1.0 eq), Pd 2 (dba) 3 (0.05eq), sodium tert-butoxide (NaOtBu) (2.0eq) and XPhos (0.1eq) were dissolved in dioxane (0.1M), and the resulting reaction mixture was stirred at 120°C for 4 hours. The reaction mixture was cooled at room temperature, and then three extraction processes were performed with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound GD03-4 (yield of 75%).

[0498] 5. Synthesis of intermediate compound GD03-5

[0499] The intermediate compound GD03-4 (1.0 eq), 3-fluorophenol (1.0 eq) and K 2 CO 3 (1.2 eq) was added to acetonitrile, and the resulting reaction mixture was refluxed for 2 hours. The reaction mixture was filtered and then concentrated to synthesize the intermediate compound GD03-5 (yield 90%).

[0500] 6. Synthesis of intermediate compound GD03-6

[0501] 2,6-Dibromoaniline (1.0 eq), phenylboronic acid (1.0 eq), Pd(PPh 3 ) 4 (0.05eq) and K 2 CO 3 (2.0 eq) was dissolved in a 4:1 volume ratio of THF and H 2 O solution (0.1M), and the resulting reaction solution was stirred at 80°C for 12 hours. The reaction mixture was subjected to three extraction processes with AcOEt and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize an intermediate compound GD03-6 (yield 74%).

[0502] 7. Synthesis of intermediate compound GD03-7

[0503] The intermediate compound GD03-6 (1.0 eq), (3,5-di-tert-butylphenyl)boronic acid (1.5 eq), Pd(PPh 3 ) 4 (0.05eq) and K 2 CO 3 (2.0 eq) was dissolved in a 4:1 volume ratio of THF and H 2 O solution (0.1M), and the resulting reaction solution was stirred at 80 ° C for 12 hours. The reaction mixture was subjected to three extraction processes with AcOEt and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound GD03-7 (yield 92%).

[0504] 8. Synthesis of intermediate compound GD03-8

[0505] The intermediate compound GD03-7 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd 2 (dba) 3(0.1eq), SPhos (0.15eq) and NaOtBu (4.0eq) were dissolved in toluene (0.1M), and the resulting reaction mixture was stirred at 120°C for 12 hours. The reaction mixture was cooled at room temperature, filtered through Celite with dichloromethane, and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound GD03-8 (yield 80%).

[0506] 9. Synthesis of intermediate compound GD03-9

[0507] The intermediate compound GD03-8 (1.0 eq), tin (3.0 eq) and HCl (12 M, 5.0 eq) were dissolved in ethanol (0.12 M), and the resulting reaction mixture was stirred at 80 ° C for 12 hours. The reaction mixture was neutralized with NaOH, and then three extraction processes were performed with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize the intermediate compound GD03-9 (yield of 75%).

[0508] 10. Synthesis of intermediate compound GD03-10

[0509] The intermediate compound GD03-5 (1.0 eq), the intermediate compound GD03-9 (1.0 eq), 2-chloropyridine (1.0 eq), Pd 2 (dba) 3 (0.05eq), NaOtBu (2.0eq) and XPhos (0.1eq) were dissolved in dioxane (0.1M), and the resulting reaction mixture was stirred at 120°C for 4 hours. The reaction mixture was cooled at room temperature, and then three extraction processes were performed with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound GD03-10 (yield 62%).

[0510] 11. Synthesis of intermediate compound GD03-11

[0511] The intermediate compound GD03-10 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq), and the resulting reaction mixture was stirred at 80°C for 12 hours. The reaction mixture was subjected to three extraction processes with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize the intermediate compound GD03-11 (yield of 83%).

[0512] 12. Synthesis of compound GD03

[0513] The intermediate compound GD03-11 (1.0 eq), K 2 PtCl 4 (1.1 eq) and 2,6-lutidine (4.0 eq) were dissolved in o-dichlorobenzene (o-DCB) (0.05 M), and the resulting reaction mixture was stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and then Si filtered with dichloromethane and n-hexane to remove o-DCB therefrom, thereby synthesizing compound GD03 (yield 52%).

[0514] Synthesis of compound GD44

[0515]

[0516] 1. Synthesis of intermediate compound GD44-1

[0517] Mg (2.0 eq) was added to THF (3.5 M) and 1,2-dibromoethane (75 M), and the resulting reaction mixture was stirred. A reactant obtained by dissolving 2-benzyl-5-fluoroisoindoline-1,3-dione (1.0 eq) in THF (0.5 M) was added thereto, and the reaction mixture was refluxed at 90 ° C. A reactant obtained by dissolving 1-bromo-2-chlorobenzene (1.2 eq) in THF (1.5 M) was added thereto, and the reaction mixture was refluxed for 3 hours and cooled at room temperature. NH 4 Cl (0.6M) aqueous solution, and the reaction mixture was subjected to three extraction processes with ether and water to obtain an organic layer. The obtained organic layer was dried over anhydrous sodium sulfate, concentrated, and then recrystallized with hexane and acetone to synthesize the intermediate compound GD44-1 (yield 48%).

[0518] 2. Synthesis of intermediate compound GD44-2

[0519] The intermediate compound GD44-1 (1.0 eq), NaHCO 3 (1.2 eq) and NBS (1.2 eq) were dissolved in a 9:1 volume ratio of dioxane and H 2 O solution (0.25 M), and the resulting reaction mixture was stirred for 28 hours. The reaction mixture was concentrated and then recrystallized with hexane and ethyl acetate (AcOEt) to synthesize the intermediate compound GD44-2 (yield 75%).

[0520] 3. Synthesis of intermediate compound GD44-3

[0521] The intermediate compound GD44-2 (1.0 eq) was dissolved in MeOH, and a compound obtained by dissolving hydrazine hydrate (2.5 eq) in MeOH (0.4 M) was added thereto at 0° C. for 5 minutes. The resulting reaction mixture was stirred for 30 minutes, concentrated, dissolved in 1N HCl (1.5 M), then filtered, and the filtrate was washed with water and 1N HCl aqueous solution, and neutralized with KOH in an ice bath. Then, the precipitate was recovered, washed with water, and then dried to synthesize the intermediate compound GD44-3 (yield 49%).

[0522] 4. Synthesis of intermediate compound GD44-4

[0523] The intermediate compound GD44-3 (1.0 eq), 2-chloropyridine (1.0 eq), Pd 2 (dba) 3 (0.05eq), sodium tert-butoxide (NaOtBu) (2.0eq) and XPhos (0.1eq) were dissolved in dioxane (0.1M), and the resulting reaction mixture was stirred at 120°C for 4 hours. The reaction mixture was cooled at room temperature, and then three extraction processes were performed with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound GD44-4 (yield was 77%).

[0524] 5. Synthesis of intermediate compound GD44-5

[0525] The intermediate compound GD44-4 (1.0 eq), 3-fluorophenol (1.0 eq) and K 2 CO 3 (1.2 eq) was added to acetonitrile, and the resulting reaction mixture was refluxed for 2 hours. The reaction mixture was filtered and then concentrated to synthesize the intermediate compound GD44-5 (yield 81%).

[0526] 6. Synthesis of intermediate compound GD44-6

[0527] 2,6-dibromo-4-(tert-butyl)aniline (1.0 eq), (phenyl-D 5 )boric acid (1.0 eq), Pd(PPh 3 ) 4 (0.05eq) and K 2 CO 3 (2.0 eq) was dissolved in a 4:1 volume ratio of THF and H 2O solution (0.1M), and the resulting reaction mixture was stirred at 80°C for 12 hours. The reaction mixture was subjected to three extraction processes with AcOEt and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize an intermediate compound GD44-6 (yield 71%).

[0528] 7. Synthesis of intermediate compound GD44-7

[0529] The intermediate compound GD44-6 (1.0 eq), (3,5-di-tert-butylphenyl)boronic acid (1.5 eq), Pd(PPh 3 ) 4 (0.05eq) and K 2 CO 3 (2.0 eq) was dissolved in a 4:1 volume ratio of THF and H 2 O solution (0.1M), and the resulting reaction solution was stirred at 80°C for 12 hours. The reaction mixture was subjected to three extraction processes with AcOEt and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize an intermediate compound GD44-7 (yield 91%).

[0530] 8. Synthesis of intermediate compound GD44-8

[0531] The intermediate compound GD44-7 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd 2 (dba) 3 (0.1eq), SPhos (0.15eq) and NaOtBu (4.0eq) were dissolved in toluene (0.1M), and the resulting reaction mixture was stirred at 120°C for 12 hours. The reaction mixture was cooled at room temperature, filtered through Celite with dichloromethane, and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound GD44-8 (yield 83%).

[0532] 9. Synthesis of intermediate compound GD44-9

[0533] The intermediate compound GD44-8 (1.0 eq), tin (3.0 eq) and HCl (12 M, 5.0 eq) were dissolved in ethanol (0.12 M), and the resulting reaction mixture was stirred at 80 ° C for 12 hours. The reaction mixture was neutralized with NaOH, and then three extraction processes were performed with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize the intermediate compound GD44-9 (yield was 79%).

[0534] 10. Synthesis of intermediate compound GD44-10

[0535] The intermediate compound GD44-5 (1.0 eq), the intermediate compound GD44-9 (1.0 eq), 2-chloropyridine (1.0 eq), Pd 2 (dba) 3 (0.05eq), NaOtBu (2.0eq) and XPhos (0.1eq) were dissolved in dioxane (0.1M), and the resulting reaction mixture was stirred at 120°C for 4 hours. The reaction mixture was cooled at room temperature, and then three extraction processes were performed with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound GD44-10 (yield 68%).

[0536] 11. Synthesis of intermediate compound GD44-11

[0537] The intermediate compound GD44-10 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq), and the resulting reaction mixture was stirred at 80°C for 12 hours. The reaction mixture was subjected to three extraction processes with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize the intermediate compound GD44-11 (yield of 84%).

[0538] 12. Synthesis of compound GD44

[0539] The intermediate compound GD44-11 (1.0 eq), K 2 PtCl 4 (1.1 eq) and 2,6-lutidine (4.0 eq) were dissolved in o-DCB (0.05 M), and the resulting reaction mixture was stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature and then Si filtered with dichloromethane and n-hexane to remove o-DCB therefrom, thereby synthesizing compound GD44 (yield 50%).

[0540] Synthesis of compound GD85

[0541]

[0542] 1. Synthesis of intermediate compound GD85-1

[0543] Mg (2.0 eq) was added to THF (3.5 M) and 1,2-dibromoethane (75 M), and the resulting reaction mixture was stirred. A reactant obtained by dissolving 2-benzyl-5-fluoroisoindoline-1,3-dione (1.0 eq) in THF (0.5 M) was added thereto, and the reaction mixture was refluxed at 90 ° C. A reactant obtained by dissolving 1-bromo-2-chlorobenzene (1.2 eq) in THF (1.5 M) was added thereto, and the reaction mixture was refluxed for 3 hours and cooled at room temperature. NH 4 Cl (0.6M) aqueous solution, and the reaction mixture was subjected to three extraction processes with ether and water to obtain an organic layer. The obtained organic layer was dried over anhydrous sodium sulfate, concentrated, and then recrystallized with hexane and acetone to synthesize the intermediate compound GD85-1 (yield 48%).

[0544] 2. Synthesis of intermediate compound GD85-2

[0545] The intermediate compound GD85-1 (1.0 eq), NaHCO 3 (1.2 eq) and NBS (1.2 eq) were dissolved in a 9:1 volume ratio of dioxane and H 2 O solution (0.25 M), and the resulting reaction mixture was stirred for 28 hours. The reaction mixture was concentrated and then recrystallized with hexane and ethyl acetate (AcOEt) to synthesize the intermediate compound GD85-2 (yield 75%).

[0546] 3. Synthesis of intermediate compound GD85-3

[0547] The intermediate compound GD85-2 (1.0 eq) was dissolved in MeOH, and a compound obtained by dissolving hydrazine hydrate (2.5 eq) in MeOH (0.4 M) was added thereto at 0° C. for 5 minutes. The resulting reaction mixture was stirred for 30 minutes, concentrated, dissolved in 1N HCl (1.5 M), then filtered, and the filtrate was washed with water and 1N HCl aqueous solution, and neutralized with KOH in an ice bath. Then, the precipitate was recovered, washed with water, and then dried to synthesize the intermediate compound GD85-3 (yield 49%).

[0548] 4. Synthesis of intermediate compound GD85-4

[0549] The intermediate compound GD85-3 (1.0 eq), 4-(tert-butyl)-2-chloropyridine (1.0 eq), Pd 2 (dba) 3 (0.05eq), NaOtBu (2.0eq) and XPhos (0.1eq) were dissolved in dioxane (0.1M), and the resulting reaction mixture was stirred at 120°C for 4 hours. The reaction mixture was cooled at room temperature, and then three extraction processes were performed with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound GD85-4 (yield 74%).

[0550] 5. Synthesis of intermediate compound GD85-5

[0551] The intermediate compound GD85-4 (1.0 eq), 3-fluorophenol (1.0 eq) and K 2 CO 3 (1.2 eq) was added to acetonitrile, and the resulting reaction mixture was refluxed for 2 hours. The reaction mixture was filtered and then concentrated to synthesize the intermediate compound GD85-5 (yield 80%).

[0552] 6. Synthesis of intermediate compound GD85-6

[0553] 2,6-dibromoaniline (1.0 eq), (4-(tert-butyl)phenyl)boronic acid (1.0 eq), Pd(PPh 3 ) 4 (0.05eq) and K 2 CO 3 (2.0 eq) was dissolved in a 4:1 volume ratio of THF and H 2 O solution (0.1M), and the resulting reaction solution was stirred at 80°C for 12 hours. The reaction mixture was subjected to three extraction processes with AcOEt and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize an intermediate compound GD85-6 (yield 72%).

[0554] 7. Synthesis of intermediate compound GD85-7

[0555] The intermediate compound GD85-6 (1.0 eq), (3,5-di-tert-butylphenyl)boronic acid (1.5 eq), Pd(PPh 3 ) 4 (0.05eq) and K 2 CO 3 (2.0 eq) was dissolved in a 4:1 volume ratio of THF and H2 O solution (0.1M), and the resulting reaction solution was stirred at 80°C for 12 hours. The reaction mixture was subjected to three extraction processes with AcOEt and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize an intermediate compound GD85-7 (yield 92%).

[0556] 8. Synthesis of intermediate compound GD85-8

[0557] The intermediate compound GD85-7 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd 2 (dba) 3 (0.1eq), SPhos (0.15eq) and NaOtBu (4.0eq) were dissolved in toluene (0.1M), and the resulting reaction mixture was stirred at 120°C for 12 hours. The reaction mixture was cooled at room temperature, filtered through Celite with dichloromethane, and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound GD85-8 (yield 84%).

[0558] 9. Synthesis of intermediate compound GD85-9

[0559] The intermediate compound GD85-8 (1.0 eq), tin (3.0 eq) and HCl (12 M, 5.0 eq) were dissolved in ethanol (0.12 M), and the resulting reaction mixture was stirred at 80 ° C for 12 hours. The reaction mixture was neutralized with NaOH, and then three extraction processes were performed with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize the intermediate compound GD85-9 (yield was 81%).

[0560] 10. Synthesis of intermediate compound GD85-10

[0561] The intermediate compound GD85-5 (1.0 eq), the intermediate compound GD85-9 (1.0 eq), 2-chloropyridine (1.0 eq), Pd 2 (dba) 3(0.05eq), NaOtBu (2.0eq) and XPhos (0.1eq) were dissolved in dioxane (0.1M), and the resulting reaction mixture was stirred at 120°C for 4 hours. The reaction mixture was cooled at room temperature, and then three extraction processes were performed with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound GD85-10 (yield 65%).

[0562] 11. Synthesis of intermediate compound GD85-11

[0563] The intermediate compound GD85-10 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq), and the resulting reaction mixture was stirred at 80°C for 12 hours. The reaction mixture was subjected to three extraction processes with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize the intermediate compound GD85-11 (yield 87%).

[0564] 12. Synthesis of compound GD85

[0565] The intermediate compound GD85-11 (1.0 eq), K 2 PtCl 4 (1.1 eq) and 2,6-lutidine (4.0 eq) were dissolved in o-DCB (0.05 M), and the resulting reaction mixture was stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature and then Si filtered with dichloromethane and n-hexane to remove o-DCB therefrom, thereby synthesizing compound GD85 (yield 53%).

[0566] Synthesis of compound GD90

[0567]

[0568] 1. Synthesis of intermediate compound GD90-1

[0569] Mg (2.0 eq) was added to THF (3.5 M) and 1,2-dibromoethane (75 M), and the resulting reaction mixture was stirred. A reactant obtained by dissolving 2-benzyl-5-fluoroisoindoline-1,3-dione (1.0 eq) in THF (0.5 M) was added thereto, and the reaction mixture was refluxed at 90 ° C. A reactant obtained by dissolving 1-bromo-2-chlorobenzene (1.2 eq) in THF (1.5 M) was added thereto, and the reaction mixture was refluxed for 3 hours and cooled at room temperature. NH 4Cl (0.6M) aqueous solution, and the reaction mixture was subjected to three extraction processes with ether and water to obtain an organic layer. The obtained organic layer was dried over anhydrous sodium sulfate, concentrated, and then recrystallized with hexane and acetone to synthesize the intermediate compound GD90-1 (yield 48%).

[0570] 2. Synthesis of intermediate compound GD90-2

[0571] The intermediate compound GD90-1 (1.0 eq), NaHCO 3 (1.2 eq) and NBS (1.2 eq) were dissolved in a 9:1 volume ratio of dioxane and H 2 O solution (0.25 M), and the resulting reaction mixture was stirred for 28 hours. The reaction mixture was concentrated and then recrystallized with hexane and AcOEt to synthesize the intermediate compound GD90-2 (yield 75%).

[0572] 3. Synthesis of intermediate compound GD90-3

[0573] The intermediate compound GD90-2 (1.0 eq) was dissolved in MeOH, and a compound obtained by dissolving hydrazine hydrate (2.5 eq) in MeOH (0.4 M) was added thereto at 0° C. for 5 minutes. The resulting reaction mixture was stirred for 30 minutes, concentrated, dissolved in 1N HCl (1.5 M), then filtered, and the filtrate was washed with water and 1N HCl aqueous solution, and neutralized with KOH in an ice bath. Then, the precipitate was recovered, washed with water, and then dried to synthesize the intermediate compound GD90-3 (yield 49%).

[0574] 4. Synthesis of intermediate compound GD90-4

[0575] The intermediate compound GD90-3 (1.0 eq), 4-(tert-butyl)-2-chloropyridine (1.0 eq), Pd 2 (dba) 3 (0.05eq), NaOtBu (2.0eq) and XPhos (0.1eq) were dissolved in dioxane (0.1M), and the resulting reaction mixture was stirred at 120°C for 4 hours. The reaction mixture was cooled at room temperature, and then three extraction processes were performed with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound GD90-4 (yield 74%).

[0576] 5. Synthesis of intermediate compound GD90-5

[0577] The intermediate compound GD90-4 (1.0 eq), 3-fluorophenol (1.0 eq) and K 2 CO 3 (1.2 eq) was added to acetonitrile, and the resulting reaction mixture was refluxed for 2 hours. The reaction mixture was filtered and then concentrated to synthesize the intermediate compound GD90-5 (yield 80%).

[0578] 6. Synthesis of intermediate compound GD90-6

[0579] 2,6-dibromoaniline (1.0 eq), (4-(tert-butyl)phenyl)boronic acid (1.0 eq), Pd(PPh 3 ) 4 (0.05eq) and K 2 CO 3 (2.0 eq) was dissolved in a 4:1 volume ratio of THF and H 2 O solution (0.1M), and the resulting reaction solution was stirred at 80°C for 12 hours. The reaction mixture was subjected to three extraction processes with AcOEt and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize an intermediate compound GD90-6 (yield 72%).

[0580] 7. Synthesis of intermediate compound GD90-7

[0581] The intermediate compound GD90-6 (1.0 eq), (3,5-bis(methyl-D 3 )phenyl)boronic acid (1.5eq), Pd(PPh 3 ) 4 (0.05eq) and K 2 CO 3 (2.0 eq) was dissolved in a 4:1 volume ratio of THF and H 2 O solution (0.1M), and the resulting reaction solution was stirred at 80°C for 12 hours. The reaction mixture was subjected to three extraction processes with AcOEt and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize an intermediate compound GD90-7 (yield 96%).

[0582] 8. Synthesis of intermediate compound GD90-8

[0583] The intermediate compound GD90-7 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd 2 (dba) 3(0.1eq), SPhos (0.15eq) and NaOtBu (4.0eq) were dissolved in toluene (0.1M), and the resulting reaction mixture was stirred at 120°C for 12 hours. The reaction mixture was cooled at room temperature, filtered through Celite with dichloromethane, and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound GD90-8 (yield 86%).

[0584] 9. Synthesis of intermediate compound GD90-9

[0585] The intermediate compound GD90-8 (1.0 eq), tin (3.0 eq) and HCl (12 M, 5.0 eq) were dissolved in ethanol (0.12 M), and the resulting reaction mixture was stirred at 80 ° C for 12 hours. The reaction mixture was neutralized with NaOH, and then three extraction processes were performed with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize the intermediate compound GD90-9 (yield 84%).

[0586] 10. Synthesis of intermediate compound GD90-10

[0587] The intermediate compound GD90-5 (1.0 eq), the intermediate compound GD90-9 (1.0 eq), 2-chloropyridine (1.0 eq), Pd 2 (dba) 3 (0.05eq), NaOtBu (2.0eq) and XPhos (0.1eq) were dissolved in dioxane (0.1M), and the resulting reaction mixture was stirred at 120°C for 4 hours. The reaction mixture was cooled at room temperature, and then three extraction processes were performed with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound GD90-10 (yield 70%).

[0588] 11. Synthesis of intermediate compound GD90-11

[0589] The intermediate compound GD90-10 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq), and the resulting reaction mixture was stirred at 80°C for 12 hours. The reaction mixture was subjected to three extraction processes with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize the intermediate compound GD90-11 (yield 88%).

[0590] 12. Synthesis of compound GD90

[0591] The intermediate compound GD90-11 (1.0 eq), K 2 PtCl 4 (1.1 eq) and 2,6-lutidine (4.0 eq) were dissolved in o-DCB (0.05 M), and the resulting reaction mixture was stirred at 120° C. for 12 hours. The reaction mixture was cooled at room temperature, and then Si filtered with dichloromethane and n-hexane to remove o-DCB therefrom, thereby synthesizing compound GD90 (yield 55%).

[0592] Obtain the compound synthesized according to the synthesis example 1 H NMR and MS / FAB, and are shown in Table 1. Those skilled in the art can easily recognize methods for synthesizing compounds other than the compounds synthesized in the synthesis examples herein by referring to the synthesis routes and source materials.

[0593] Table 1

[0594]

[0595] Manufacturing of light-emitting devices

[0596] Example 1

[0597] As the anode, a 15 ohm per square centimeter (Ω / cm 2 )(1200 Angstroms The ITO glass substrate was cut into a size of 50 millimeters (mm) × 50 mm × 0.7 mm, and ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by ultraviolet irradiation and ozone exposure for 30 minutes. Then, the obtained glass substrate was loaded onto a vacuum deposition device. 2-TNATA was vacuum deposited on the glass substrate to form a Then, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as NPB) as a hole transport compound is vacuum-deposited on the hole injection layer to form a hole injection layer having a thickness of The compound GD03 of the present disclosure as a dopant and 3,3-di(9H-carbazole-9-yl)biphenyl (mCBP) as a host are co-deposited on the hole transport layer to form a The emission layer is a green phosphorescent emission layer (doping rate: 10 wt%). Next, diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) is vacuum deposited on the emission layer to form a green phosphorescent emission layer. Then, Alq 3Vacuum deposition on the emission layer to form a An electron transport layer having a thickness of , LiF as an alkali metal halide is vacuum deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Al is vacuum deposited on the electron injection layer to form a A cathode with a thickness of is formed to form a LiF / Al electrode, thereby completing the manufacture of the light-emitting device.

[0598] Example 2 to Example 4

[0599] Light-emitting devices were manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 2 were each used instead of Compound GD03 as a dopant material in the emission layer.

[0600] Comparative Example 1

[0601] In addition to using Ir(PPy) 3 A light emitting device was manufactured in substantially the same manner as in Example 1, except that compound GD03 was replaced as the dopant material in the emission layer.

[0602] In order to evaluate the characteristics of the light emitting devices of Examples 1 to 4 and Comparative Example 1, the current at 10 mA / cm 2 The driving voltage, lifetime, vibrational recombination energy and efficiency of the light-emitting device were measured using a source meter (Keithley Instruments, 2400 series).

[0603] Table 2 shows the results of evaluating the characteristics of the light emitting devices.

[0604] Table 2

[0605]

[0606] Referring to the results in Table 2, it is confirmed that compared with the efficiency, driving voltage, lifespan and vibrational reorganization energy value of the light-emitting device of Comparative Example 1, the light-emitting devices of Examples 1 to 4 all have higher efficiency, lower driving voltage, longer lifespan and lower vibrational reorganization energy value.

[0607] RT 80 % refers to 40mA / cm 2 The time taken for the emission intensity to decrease to 80% of the maximum value.

[0608] According to one or more embodiments, the light emitting device may have excellent or appropriate efficiency.

[0609] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects within each embodiment should generally be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope as defined by the claims and their equivalents.

Claims

1. A light emitting device, comprising: a first electrode; a second electrode, facing the first electrode; as well as an intermediate layer, between the first electrode and the second electrode, and including an emission layer, Wherein, the emission layer includes a compound represented by Formula 1: Formula 1 ML 401 L 402 Formula 1-1 Formula 1-2 Among them, in Formula 1, Formula 1-1 and Formula 1-2, M is a transition metal, L 401 and L 402 are independently Formula 1-1 or Formula 1-2, wherein L 401 and L 402 At least one selected from includes formula 1-2, X 401 and X 402 are independently N or C, Ring A 401 and Ring A 402 are independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, T 401 is a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、 -C(Q 411 )=or=C=, X 403 and X 404 are independently chemical bonds, O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ), R 401 To R 405 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 20 Alkyl, unsubstituted or substituted with at least one R 10a C1-C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O)2(Q 401 ) or -P(=O)(Q 401 )(Q 402 ), xc11 and xc12 are each independently an integer from 0 to 10, xc13 and xc14 are each independently an integer from 0 to 4, xc15 is an integer from 0 to 3, * and *' in Formula 1-1 and Formula 1-2 both represent the binding site with M in Formula 1, Formula 1-1 and Formula 1-2 can be optionally connected via T 402 Connect to each other, T 402 is a linker and as referred to in T 401 As defined, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl, C2-C 60 Heteroarylalkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or a combination thereof C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl, C2-C 60 Heteroarylalkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or a combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q 11 To Q 13 , Q 21 To Q 23 , Q 31 To Q 33 , Q 401 To Q 403 and Q 411 To Q 414 Are independently: Hydrogen; Deuterium; -F; -Cl; -Br; -I; Hydroxyl; Cyano; Nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; or C1-C 60 Alkoxy; or Unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C4 alkoxy, phenyl, biphenyl or a combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 Heteroarylalkyl.

2. The light emitting device according to claim 1, wherein: The first electrode is an anode, The second electrode is a cathode, and in: The intermediate layer further includes an electron transport region, the electron transport region being between the second electrode and the emission layer and including an electron transport layer, a hole blocking layer, an electron injection layer, or a combination thereof; or The intermediate layer further includes a hole transport region between the first electrode and the emission layer and including a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or a combination thereof.

3. The light emitting device according to claim 1, wherein: The vibration reorganization energy of the compound represented by Formula 1 is 200 cm -1 or smaller.

4. The light emitting device according to claim 1, wherein: The emission layer is configured to emit green light. 5 . An electronic device comprising the light emitting device according to claim 1 .

6. The electronic device according to claim 5, further comprising a thin film transistor, in, The thin film transistor includes a source electrode and a drain electrode, and The first electrode is electrically connected to the source electrode or the drain electrode of the thin film transistor.

7. An electronic device, comprising the electronic device according to claim 5, wherein: The electronic device is at least one selected from a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and / or a light for signaling, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a phone, a tablet computer, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional display, a virtual reality or augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater or stadium screen, a light therapy device, a sign, and combinations thereof.

8. A compound represented by Formula 1: Formula 1 ML 401 L 402 Formula 1-1 Formula 1-2 in, In Formula 1, Formula 1-1 and Formula 1-2, M is a transition metal, L 401 and L 402 are independently Formula 1-1 or Formula 1-2, wherein L 401 and L 402 At least one selected from includes formula 1-2, X 401 and X 402 are independently N or C, Ring A 401 and Ring A 402 are independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, T 401 is a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、 -C(Q 411 )=or=C=, X 403 and X 404 are independently chemical bonds, O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ), R 401 To R 405 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 20 Alkyl, unsubstituted or substituted with at least one R 10a C1-C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O)2(Q 401 ) or -P(=O)(Q 401 )(Q 402 ), xc11 and xc12 are each independently an integer from 0 to 10, xc13 and xc14 are each independently an integer from 0 to 4, xc15 is an integer from 0 to 3, * and *' in Formula 1-1 and Formula 1-2 both represent the binding site with M in Formula 1, Formula 1-1 and Formula 1-2 can be optionally connected via T 402 Connect to each other, T 402 is a linker and as referred to in T 401 As defined, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl, C2-C 60 Heteroarylalkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl, C2-C 60 Heteroarylalkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or a combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q 11 To Q 13 , Q 21 To Q 23 , Q 31 To Q 33 , Q 401 To Q 403 and Q 411 To Q 414 Are independently: Hydrogen; Deuterium; -F; -Cl; -Br; -I; Hydroxyl; Cyano; Nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; or C1-C 60 Alkoxy; or Unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C4 alkoxy, phenyl, biphenyl or a combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 Heteroarylalkyl.

9. The compound according to claim 8, wherein In Formula 1-2, the compound further includes a pyridine moiety and an N-bridged anthracene moiety orthogonal to the pyridine moiety.

10. The compound according to claim 8, wherein Ring A 401 and Ring A 402 are independently unsubstituted or substituted with at least one R 10a C6-C 60 Aryl, unsubstituted or substituted with at least one R 10a C1-C 60 Heteroaryl is either unsubstituted or substituted with at least one R 10a A monovalent non-aromatic condensed heteropolycyclic group.

11. The compound according to claim 8, wherein M is iridium, platinum, palladium, osmium, titanium, gold, hafnium, europium, terbium, rhodium, rhenium or thulium.

12. The compound according to claim 8, wherein In formula 1-1, A 402 is benzene, R 401 is a terphenyl group, and xc11 is an integer of 1 to 3.

13. The compound according to claim 8, wherein In formula 1-1, A 401 is benzimidazole, R 401 is a terphenyl group, and xc11 is an integer of 1 to 3.

14. The compound according to claim 8, wherein Formula 1-1 and Formula 1-2 are linked to each other via a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、-C(Q 411 )=or=C= are connected to each other.

15. The compound according to claim 8, wherein Formula 1-2 is represented by Formula 1-3: Formula 1-3 Among them, in formula 1-3, R 403 To R 405 and xc13 to xc15 are all as defined with reference to Formula 1-2.

16. The compound according to claim 15, wherein In formula 1, L 401 is formula 1-1, and L 402 is formula 1-3, and A in formula 1-1 402 The N-bridged anthracene moiety in formula 1-3 is connected via a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、-C(Q 411 )=or=C= are connected to each other.

17. The compound according to claim 8, wherein Formula 1 is expressed by Formula 2: Formula 2 Among them, in formula 2, M is a transition metal, A and B are independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, T 402 is a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-、-C(Q 411 )(Q 412 )-、-C(Q 411 )=C(Q 412 )-、 -C(Q 411 )=or=C=, R 402 To R 409 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 20 Alkyl, unsubstituted or substituted with at least one R 10a C1-C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O)2(Q 401 ) or -P(=O)(Q 401 )(Q 402 ), xc12 and xc18 are each independently an integer from 0 to 3, xc13, xc14, xc16, xc17 and xc19 are each independently an integer from 0 to 4, xc15 is an integer from 0 to 2, and R 10a , Q 401 To Q 403 and Q 411 and Q 412 All are as defined in Formula 1.

18. The compound according to claim 17, wherein A and B are independently C6-C 60 Aryl.

19. The compound according to claim 17, wherein R 403 and R 407 To R 409 are independently hydrogen, deuterium or C1-C 20 alkyl.

20. The compound according to claim 8, wherein Formula 1 is represented by one selected from the following compounds: Wherein, M is Pt.

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