Organometal compound, light emitting device including organometal compound, electronic device including light emitting device
By using organometallic compounds in the light emitting device, the shortcomings in the prior art in terms of brightness, driving voltage and response speed are solved, and higher color purity and longer life are achieved.
Patent Information
- Application Number
- CN202411521382.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-10-30
- Filing Date
- 2024-10-29
- Publication Date
- 2025-05-02
AI Technical Summary
The existing light emitting devices have shortcomings in terms of brightness, driving voltage and response speed, and it is difficult to effectively improve the color purity and device life of the emitted blue light.
The organometallic compound represented by Formula 1 is used, including in the interlayer and capping layer of the light emitting device, to improve the performance of the emitting layer and reduce the intermolecular interaction.
By using organometallic compounds, the color purity of the emitting blue light is improved, the driving voltage is reduced, and the life of the light emitting device is extended.
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Figure CN119912496A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0146997 filed in the Korean Intellectual Property Office on October 30, 2023, the entire contents of which are incorporated herein by reference. Technical Field
[0003] Embodiments relate to an organometallic compound, a light-emitting device including the organometallic compound, an electronic device including the light-emitting device, and an electronic device including the light-emitting device. Background Art
[0004] The light-emitting device is a self-emissive device having a wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed.
[0005] 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 may be arranged on the first electrode in sequence. 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. These excitons transition from an excited state to a ground state, thereby generating light.
[0006] It should be understood that this background technology section is intended to provide, in part, a useful background for understanding the technology. However, this background technology section may also include ideas, concepts or cognitions that were not known or understood by a person skilled in the relevant art before the corresponding effective filing date of the subject matter disclosed herein. Summary of the invention
[0007] Embodiments include an organometallic compound, a light-emitting device including the organometallic compound, an electronic device including the light-emitting device, and an electronic device including the light-emitting device.
[0008] 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 embodiments of the disclosure.
[0009] According to an embodiment, the light emitting device may include:
[0010] The first electrode,
[0011] a second electrode facing the first electrode,
[0012] an interlayer between the first electrode and the second electrode and including an emitting layer, and
[0013] An organometallic compound represented by Formula 1:
[0014] [Formula 1]
[0015]
[0016] In formula 1,
[0017] M may be platinum (Pt), iridium (Ir), palladium (Pd), cobalt (Co), gold (Au), nickel (Ni), silver (Ag) or copper (Cu),
[0018] CY 1 CY 2 CY 31 and CY 32 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0019] CY 5 may be a non-aromatic fused polycyclic group or a non-aromatic fused heteropolycyclic group,
[0020] X 1 Can be C,
[0021] X 2 To X 4 can be independently C or N,
[0022] T 1 Can be a single bond, N(R 7 )、C(R 7 )(R 8 )、Si(R 7 )(R 8 ), S or O,
[0023] L 1 To L 3 can be independently a single bond, *-N(R 9 )-*'、*-B(R 9 )-*'、*-P(R 9 )-*'、*-C(R 9 )(R 10 )-*'、*-Si(R 9 )(R 10 )-*'、*-Ge(R 9 )(R 10 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*' or *-C(=S)-*',
[0024] a1, a2, a31, a32 and a5 may each independently be an integer selected from 0 to 20,
[0025] b1 to b3 may each independently be an integer selected from 0 to 4,
[0026] R 1 , R 2 , R 31 , R 32 , R 41 To R 43 and R 5 To R 10 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroaralkyl, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),
[0027] R 41 To R 43 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 alkyl,
[0028] R 10a Can be:
[0029] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0030] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: 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 Aralkyl, C 2 -C 60 Heteroaralkyl, -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;
[0031] Each unsubstituted or substituted 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 or C 2 -C 60 Heteroaralkyl: 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 Aralkyl, C 2 -C 60 Heteroaralkyl, -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; or
[0032] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and
[0033] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 may be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; pyridyl; pyrimidinyl; pyridazinyl; pyrazinyl; triazinyl; or each is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted 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 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.
[0034] In an embodiment, the first electrode may be an anode; the second electrode may be a cathode; the interlayer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode; the hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer or any combination thereof; and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer or any combination thereof.
[0035] In an embodiment, the interlayer may include an organometallic compound.
[0036] In an embodiment, the emission layer may include an organometallic compound.
[0037] In an embodiment, the emission layer may include a host, a dopant, and a sensitizer; and the sensitizer may include an organic metal compound.
[0038] According to an embodiment, an electronic device may include a light emitting device.
[0039] In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof.
[0040] According to an embodiment, the electronic equipment may include a light emitting device.
[0041] In embodiments, the electronic device may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a phone, a mobile phone, a tablet computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, or a sign.
[0042] According to an embodiment, the organometallic compound may be represented by Formula 1 explained herein.
[0043] In an embodiment, the organometallic compound may include at least one deuterium.
[0044] In an embodiment, M may be Pt.
[0045] In an embodiment, CY 5 Can be: with at least one C 3 -C 10 Cycloalkyl fused with at least one C 6 -C 60 Aryl; or with at least one C 1 -C 10 Heterocycloalkyl fused to at least one C 6 -C 60 Aryl.
[0046] In an embodiment, X 1 The key between M and X 4 The bonds between X and M may each be coordination bonds; and 2 The key between M and X 3 The bonds between M and M may each be covalent bonds.
[0047] In an embodiment, R 41 and R 43 may each independently be hydrogen or deuterium; and R 42 may be unsubstituted or substituted with at least one R10a Substituted C 1 -C 60 alkyl.
[0048] In an embodiment, CY 5 It may be a group represented by one of Formulae 2-1 to 2-4 explained below.
[0049] In an embodiment, R 1 , R 2 , R 31 , R 32 , R 41 To R 43 and R 5 To R 10 Can be independently:
[0050] Hydrogen, deuterium, -F, -Cl, -Br, -I or cyano;
[0051] methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl or 1,2-dimethylpropyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; or
[0052] Phenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, azadibenzofuranyl, azadibenzothienyl or azacarbazolyl, each unsubstituted or substituted by: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl or phenyl, each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro.
[0053] In an embodiment, R 6 The phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanthrenyl, heptalenyl, tetracenyl, pyrenyl, hexenyl, pentacene, rubenyl, coronenyl, ovalenyl, biphenyl or terphenyl, each of which is unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 20 Alkyl, C 6 -C 60 aryl or any combination thereof.
[0054] In an embodiment, R 6It may be a group represented by one of Formula 3-1 to Formula 3-3 explained below.
[0055] In an embodiment, the organometallic compound represented by Formula 1 may be one of Compound 1 to Compound 288 explained below.
[0056] It should be understood that the above embodiments have been described in a general and explanatory sense only and not for limiting purposes, and the present disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS
[0057] The attached drawings are included to provide a further understanding of the embodiments, and are incorporated into and constitute a part of this specification. The drawings illustrate the embodiments of the present disclosure and its principles. The above and other aspects and features of the present disclosure will become more apparent by describing its embodiments in detail with reference to the attached drawings, in which:
[0058] Figure 1 is a schematic cross-sectional view of a light emitting device according to an embodiment;
[0059] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment;
[0060] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment;
[0061] Figure 4 is a schematic perspective view of an electronic device including a light emitting device according to an embodiment;
[0062] Figure 5 is a schematic perspective view of the exterior of a vehicle as an electronic device including a light emitting device according to an embodiment; and
[0063] FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle according to an embodiment. DETAILED DESCRIPTION
[0064] The present disclosure will now be described more fully below with reference to the attached drawings in which embodiments are shown. However, the present disclosure may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that the present disclosure will be thorough and complete and will fully convey the scope of the present disclosure to those skilled in the art.
[0065] In the drawings, the size (eg, thickness), ratio, and dimensions of elements may be exaggerated for ease of description and for clarity. The same reference numerals and / or the same reference characters refer to the same elements throughout.
[0066] In the description, it will be understood that when an element (or region, layer, component, etc.) is referred to as being "on", "connected to" or "coupled to" another element (or region, layer, component, etc.), it may be directly on, directly connected to or directly coupled to the other element (or region, layer, component, etc.), or one or more intervening elements (or regions, layers, components, etc.) may exist between them. In a similar sense, when an element (or region, layer, component, etc.) is described as "covering" another element (or region, layer, component, etc.), it may directly cover the other element (or region, layer, component, etc.), or one or more intervening elements (or regions, layers, components, etc.) may exist between them.
[0067] In the description, when an element is "directly on," "directly connected to," or "directly coupled to" another element, there are no intervening elements. For example, "directly on" may mean that two layers or two elements are disposed without additional elements such as adhesive elements between them.
[0068] As used herein, expressions used in the singular such as “a”, “an” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0069] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. For example, "A and / or B" may be understood to mean "A, B, or A and B". The terms "and" and "or" may be used in a connecting sense or a separating sense and may be understood to be equivalent to "and / or".
[0070] In the specification and claims, for the purposes of its meaning and interpretation, the term "at least one of" is intended to include the meaning of "at least one selected from the group consisting of..." For example, "at least one of A, B, and C" may be understood to mean only A, only B, only C, or any combination of two or more of A, B, and C, such as ABC, ACC, BC, or CC. When following a list of elements, the term "at least one of" modifies the entire list of elements and does not modify the individual elements of the list.
[0071] It will be understood that although the terms first, second, etc. may be used to describe various elements in this article, 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 teachings of the present disclosure, the first element may be referred to as the second element. Similarly, without departing from the scope of the present disclosure, the second element may be referred to as the first element.
[0072] For ease of description, spatially relative terms such as "below," "under," "down," "above," or "on" may be used herein to describe the relationship between one element or component and another element or component as illustrated in the accompanying drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the accompanying drawings. For example, in the case where the device illustrated in the accompanying drawings is turned over, a device that is "below" or "below" another device may be placed "above" the other device. Accordingly, the illustrative term "below" may include both a lower position and an upper position. The device may also be oriented in other directions, and therefore the spatially relative terms may be interpreted differently depending on the orientation.
[0073] As used herein, the term "about" or "approximately" includes the stated value and means within an acceptable range of deviation of the stated value determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the stated quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations of the stated value, or within ±20%, ±10%, or ±5% of the stated value.
[0074] It should be understood that the terms “comprise,” “comprising,” “include,” “including,” “have,” “having,” “contains,” and “containing” and the like are intended to indicate the presence of the recited features, integers, steps, operations, elements, components, or any combination thereof in the present disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or any combination thereof.
[0075] Unless otherwise defined or implied herein, all terms (including technical terms and scientific terms) used have the same meaning as those commonly understood by those skilled in the art to which the present disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and should not be interpreted in an ideal or overly formal sense unless clearly defined in the specification.
[0076] Embodiments provide a light emitting device, which may include a first electrode, a second electrode facing the first electrode, an interlayer between the first electrode and the second electrode and including an emission layer, and an organic metal compound represented by Formula 1:
[0077] [Formula 1]
[0078]
[0079] In formula 1,
[0080] M may be platinum (Pt), iridium (Ir), palladium (Pd), cobalt (Co), gold (Au), nickel (Ni), silver (Ag) or copper (Cu),
[0081] CY 1 CY 2 CY 31 and CY 32 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0082] CY 5 may be a non-aromatic fused polycyclic group or a non-aromatic fused heteropolycyclic group,
[0083] X 1 Can be C,
[0084] X 2 To X 4 can be independently C or N,
[0085] T 1 Can be a single bond, N(R 7 )、C(R 7 )(R 8 )、Si(R 7 )(R 8 ), S or O,
[0086] L 1 To L 3 can be independently a single bond, *-N(R 9 )-*'、*-B(R 9 )-*'、*-P(R 9 )-*'、*-C(R 9 )(R 10 )-*'、*-Si(R 9 )(R 10 )-*'、*-Ge(R 9 )(R 10 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*' or *-C(=S)-*',
[0087] a1, a2, a31, a32 and a5 may each independently be an integer selected from 0 to 20,
[0088] b1 to b3 may each independently be an integer selected from 0 to 4,
[0089] R 1 , R 2 , R 31 , R 32 , R 41 To R 43 and R 5 To R 10 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C 7 -C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Heteroaralkyl, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1) or -P(=O)(Q 1 )(Q 2 ),
[0090] R 41 To R 43 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 alkyl,
[0091] R 10a Can be:
[0092] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0093] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: 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 Aralkyl, C 2 -C 60 Heteroaralkyl, -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;
[0094] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl: 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 Aralkyl, C 2 -C 60 Heteroaralkyl, -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; or
[0095] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-P(Q 31 )(Q 32 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and
[0096] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 may be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; pyridyl; pyrimidinyl; pyridazinyl; pyrazinyl; triazinyl; or each is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted 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 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.
[0097] In an embodiment, the organometallic compound represented by Formula 1 may include at least one deuterium atom.
[0098] In an embodiment, M may be Pt.
[0099] In an embodiment, CY 1 CY 2 CY 31 and CY 32 may be each independently unsubstituted or substituted with at least one R 10aSubstituted cyclopentadienyl, adamantyl, norbornyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylene, peryl, pentaphenanthrenyl, heptalenyl, tetraphenylene, phenanthrenyl, hexaphenylene, pentacene, rubenyl, coronenyl, ovalenyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthrenyl, indenoanthryl, pyrrolyl , thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiolsyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiolsyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolcarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzothiolsylcarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranocarbazolyl benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, indazolyl, pyridinyl, pyrimid ... oxazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzosilyl, azadibenzothiophenyl or azadibenzofuranyl.
[0100] In an embodiment, CY 1 CY 2 CY 31 and CY 32 may be each independently unsubstituted or substituted with at least one R 10a substituted phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrene, 1,2-triphenylene, pyrrolyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, carbazolyl, indenocarbazolyl, indolecarbazolyl, benzindololecarbazolyl, benzocarbazolyl, pyrazolyl, imidazolyl, triazolyl, benzo pyrazolyl, benzimidazolyl, indazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl or azafluorenyl.
[0101] In an embodiment, CY 5 Can be: with at least one C 3 -C 10 Cycloalkyl fused with at least one C 6 -C 60 Aryl; or with at least one C 1 -C 10 Heterocycloalkyl fused to at least one C 6 -C 60 Aryl.
[0102] In an embodiment, in CY 5 In, C 6 -C 60 Aryl can be phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanthrenyl, heptalenyl, tetracenyl, phenanthrenyl, hexenyl, pentenyl, rubenyl, coronenyl or ovalenyl,
[0103] C 3 -C 10 The cycloalkyl group may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl or bicyclo[2.2.2]octyl, and
[0104] C 1 -C 10 The heterocycloalkyl group may be 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl or tetrahydrothienyl.
[0105] In an embodiment, X 1 The key between M and X 4 The bonds between X and M may each be coordination bonds, and X 2 The key between M and X 3 The bonds between M and M may each be covalent bonds.
[0106] In an embodiment, X 2 Can be C, X 3 Can be C, and X 4 Can be N.
[0107] In an embodiment, X 1 It may be a carbon atom of a carbene portion.
[0108] In an embodiment, T 1 Can be a single bond.
[0109] In an embodiment, L 1 To L 3can be independently a single bond, *-N(R 9 )-*'、*-B(R 9 )-*'、*-C(R 9 )(R 10 )-*'、*-Si(R 9 )(R 10 )-*', *-S-*', or *-O-*'.
[0110] In an embodiment, R 41 and R 43 may each independently be hydrogen or deuterium, and R 42 may be unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 alkyl.
[0111] In an embodiment, R 1 , R 2 , R 31 , R 32 , R 41 To R 43 and R 5 To R 10 Can be independently:
[0112] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano or C 1 -C 20 alkyl;
[0113] C substituted by at least one of the following 1 -C 20 Alkyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano, nitro, C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, and pyrimidinyl;
[0114] phenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, azadibenzofuranyl, azadibenzothienyl or azacarbazolyl, each unsubstituted or substituted by at least one of the following: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF3 , -CF 2 H, -CFH 2 , cyano, C 1 -C 20 Alkyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, Quinoxalyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ) and -B(Q 31 )(Q 32 );or
[0115] -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 ) or -B(Q 1 )(Q 2 ),and
[0116] Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0117] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H or -CD 2 CDH 2 ;or
[0118] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, each unsubstituted or substituted by at least one of the following: deuterium, C 1 -C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl and triazinyl.
[0119] In an embodiment, R 1 , R 2 , R 31 , R 32 , R 41 To R 43 and R 5 To R 10 Can be independently:
[0120] Hydrogen, deuterium, -F, -Cl, -Br, -I or cyano;
[0121] methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl or 1,2-dimethylpropyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; or
[0122] Phenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, azadibenzofuranyl, azadibenzothienyl or azacarbazolyl, each unsubstituted or substituted by: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl or phenyl, each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro.
[0123] In an embodiment, CY 5 It may be a group represented by one of Formula 2-1 to Formula 2-4:
[0124]
[0125] In Formula 2-1 to Formula 2-4,
[0126] R 51 and R 52 Can be independently compared with the reference R 5 Same as described,
[0127] a51 may be an integer selected from 0 to 11,
[0128] a52 may be an integer selected from 0 to 17, and
[0129] *Indicates the bonding site to the adjacent carbon atom.
[0130] In an embodiment, CY 5 may be each unsubstituted or substituted with at least one R 10a Substituted 1,2,3,4-tetrahydronaphthyl or 1,2,3,4,5,6,7,8-octahydroanthracenyl.
[0131] In an embodiment, R 6 may be unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl.
[0132] In an embodiment, R 6 The phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, perylenyl, pentaphenanthrenyl, heptalenyl, tetracenyl, pyrenyl, hexenyl, pentacene, rubenyl, coronenyl, ovalenyl, biphenyl or terphenyl, each of which is unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C 1 -C 20 Alkyl, C 6 -C 60 aryl or any combination thereof.
[0133] In an embodiment, R 6 The phenyl, biphenyl or terphenyl groups may be each unsubstituted or substituted with deuterium, -F, cyano, nitro, 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, phenyl or any combination thereof.
[0134] In an embodiment, R 6 It may be a group represented by one of Formula 3-1 to Formula 3-3:
[0135]
[0136] In Formula 3-1 to Formula 3-3,
[0137] R 61 To R 64 Can be independently compared with the reference R 6 Same as described,
[0138] a61 may be an integer selected from 1 to 5,
[0139] a62 may be an integer selected from 1 to 3,
[0140] a63 may be an integer selected from 1 to 5,
[0141] a64 may be an integer selected from 1 to 4, and
[0142] *Indicates the bonding site to the adjacent nitrogen atom.
[0143] In an embodiment, the organometallic compound represented by Formula 1 may be one of Compound 1 to Compound 288:
[0144]
[0145]
[0146]
[0147]
[0148]
[0149]
[0150]
[0151]
[0152]
[0153]
[0154]
[0155]
[0156]
[0157]
[0158]
[0159]
[0160]
[0161]
[0162]
[0163]
[0164]
[0165]
[0166]
[0167]
[0168] In the organometallic compound represented by Formula 1, CY in Formula 1 5 It may be a non-aromatic fused polycyclic group or a non-aromatic fused heteropolycyclic group. 41 To R 43 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 alkyl.
[0169] As a result, the organic metal compound represented by Formula 1 can cause structural distortion due to the steric hindrance of the substituent, thereby improving the color purity and driving voltage of the light-emitting device emitting blue light. In a light-emitting device using the organic metal compound represented by Formula 1, the interaction between molecules can be suppressed within the light-emitting device, resulting in improved device life characteristics.
[0170] The synthesis method of the organometallic compound represented by Formula 1 can be identified by one of ordinary skill in the art by referring to the Synthesis Examples and / or Examples provided below.
[0171] At least one organic metal compound represented by Formula 1 can be used in a light-emitting device (e.g., an organic light-emitting device). Accordingly, the embodiment provides a light-emitting device, which may include: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emission layer; and an organic metal compound represented by Formula 1.
[0172] In an embodiment,
[0173] The first electrode of the light emitting device may be an anode,
[0174] The second electrode of the light emitting device may be a cathode,
[0175] The interlayer may further include a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive layer and the second electrode,
[0176] 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, and
[0177] The electron transport region may include a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
[0178] In an embodiment, the interlayer may include an organic metal compound represented by Formula 1.
[0179] In an embodiment, the emission layer may include the organic metal compound represented by Formula 1.
[0180] In an embodiment, the emission layer may include a host, a dopant, and a sensitizer, wherein the sensitizer may include an organic metal compound represented by Formula 1.
[0181] In an embodiment, the dopant may include an organic metal compound represented by Formula 1.
[0182] In an embodiment, the dopant may be a delayed fluorescence dopant.
[0183] The host may include a first host and a second host, wherein the first host may include a hole transport material, and the second host may include an electron transport material.
[0184] In an embodiment, the emissive layer may emit blue light.
[0185] In an embodiment, the organometallic compound represented by Formula 1 may not emit light.
[0186] In an embodiment, the organometallic compound represented by Formula 1 may emit light.
[0187] In an embodiment, the emission layer may further include a first host and a second host, wherein the first host may be a hole transport material including at least one electron donating group, and the second host may be an electron transport material including at least one electron withdrawing group.
[0188] In an embodiment, the emission layer may further include a third compound, wherein the third compound may be a metal-containing compound.
[0189] In an embodiment, the third compound may be used as a sensitizer. For example, the third compound may be a phosphorescence sensitizer.
[0190] In embodiments, the third compound may not emit light.
[0191] In an embodiment, the emission layer may further include at least one of an auxiliary dopant and a sensitizer.
[0192] In an embodiment, the auxiliary dopant and the sensitizer may each independently be an organic metal compound including platinum and a tetradentate ligand bonded to the platinum, wherein the tetradentate ligand may include a carbene portion chemically bonded to the platinum. For example, the auxiliary dopant and / or the sensitizer may include a third compound.
[0193] In embodiments, the first host and the second host may function as exciplex hosts.
[0194] The term "electron donating group" refers to any group having the ability to donate electrons, and may be, for example, a π-electron-rich C 3 -C 60 The electron donating group may be a nitrogen-containing C 1 -C 60 Cyclic groups other than cyclic groups.
[0195] The term "electron withdrawing group" refers to any group having electron withdrawing ability, and may be, for example, -F, -CFH 2 , -CF 2 H, -CF 3 、-CN、-NO 2 、π-electron-deficient nitrogen-containing C 1 -C 60 A cyclic group or any combination thereof, but the embodiment is not limited thereto.
[0196] Regarding the light emission pathway in the light-emitting device according to the embodiment, the first host and the second host can form an excited complex host (first step), the energy of the excited complex host can be transferred to the third compound (second step), and the energy can be transferred from the third compound to the organic metal compound represented by Formula 1 (third step).
[0197] In an embodiment, an amount of the third compound may be in a range of about 0 parts by weight to about 50 parts by weight based on a total of 100 parts by weight of the emission layer.
[0198] In an embodiment, the first host may include at least one carbazole moiety, and the second host may include at least one azine moiety.
[0199] In an embodiment, the first body may be represented by Formula 301-1A or Formula 301-2A:
[0200] [Formula 301-1A]
[0201]
[0202] [Formula 301-2A]
[0203]
[0204] In Formula 301-1A and Formula 301-2A,
[0205] Ring A 301 To Ring A 304 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0206] X 301 Can be O, S, N[(L 304 ) xb4 -R 304a ]、C(R 304a )(R 304b ) or Si(R 304a )(R 304b ),
[0207] X 302 Can be single bond, O, S, N[(L 305 ) xb5 -R 305a ]、C(R 305a )(R 305b ) or Si(R 305a )(R 305b ),
[0208] X 303 Can be single bond, O, S, N[(L 306 ) xb6 -R 306a ]、C(R 306a )(R 306b ) or Si(R 306a )(R 306b ),
[0209] xb22 and xb23 may each independently be an integer selected from 0 to 10,
[0210] L 301 To L 307 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60Heterocyclic group,
[0211] xb1 to xb7 may each independently be an integer selected from 0 to 5,
[0212] R 301 To R 303 , R 304a To R 306a , R 304b To R 306b and R 311 To R 314 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -C(Q 1 )(Q 2 )(Q 3 )、-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 ),and
[0213] Q 301 To Q 303 Can be independently compared with reference Q 1 Same as described.
[0214] In an embodiment, the first host may be one of compounds HTH1 to HTH56 or compounds HTH1' to HTH40', but the embodiment is not limited thereto:
[0215]
[0216]
[0217]
[0218]
[0219] In an embodiment, the second body may be represented by equation 302:
[0220] [Formula 302]
[0221]
[0222] In formula 302,
[0223] X 321 Can be C(R 321 ) or N,
[0224] X 322 Can be C(R 322 ) or N,
[0225] X 323 Can be C(R 323 ) or N,
[0226] X 321 To X 323 At least one of them may each be N,
[0227] L 324 To L 326 may be independently a single bond, unsubstituted or substituted by at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, *-C(Q 321 )(Q 322 )-*'、*-Si(Q 321 )(Q 322 )-*'、*-B(Q 321 )-*' or *-N(Q 321 )-*',
[0228] n324 to n326 may each independently be an integer selected from 1 to 5,
[0229] R 321 To R 326 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 323 )(Q 324 )(Q 325 )、-N(Q 323 )(Q 324 )、-B(Q 323 )(Q 324 )、-C(=O)(Q 323 )、-S(=O) 2 (Q 323 ) or -P(=O)(Q 323 )(Q 324 ),
[0230] Q 321 To Q 325 and R 321 To R 326 Two or more adjacent groups in the formula (R) may be optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 30 Heterocyclic group,
[0231] * and *' each indicate a bonding site to an adjacent atom,
[0232] R 10a may be the same as described herein, and
[0233] Q 321 To Q 325 Can be independently compared with reference Q 1 Same as described.
[0234] In an embodiment, the second host may be one of compounds ETH1 to ETH86 or compounds ETH1′ to ETH32′, but the embodiment is not limited thereto:
[0235]
[0236]
[0237]
[0238]
[0239]
[0240] In an embodiment, the third compound may be represented by Formula 401A:
[0241] [Formula 401A]
[0242] M 401 (L 401 ) xc1 (L 402 ) xc2 ,
[0243]
[0244]
[0245] In Formula 401A and Formulas 402A to 402D,
[0246] M 401 It may be a first-row transition metal of the periodic table, a second-row transition metal of the periodic table, or a third-row transition metal of the periodic table,
[0247] L 401 may be a ligand represented by one of Formulae 402A to 402D,
[0248] L 402 It can be a monodentate ligand, a bidentate ligand or a tridentate ligand,
[0249] xc1 can be 1 or 2,
[0250] xc2 may be an integer selected from 0 to 4,
[0251] A 401 To A 404 Can be independently C 5 -C 30 Carbocyclic or C 1 -C 30 Heterocyclic group,
[0252] T 401 To T 404 can each independently be a single bond, a double bond, *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', *-C(R 405 )(R 406 )-*'、*-C(R 405 )=C(R 406 )-*'、*-C(R 405 )=*'、*-Si(R 405 )(R 406 )-*'、*-B(R 405 )-*'、*-N(R 405 )-*' or *-P(R 405 )-*',
[0253] k401 to k404 can each independently be 1, 2 or 3,
[0254] Y 401 To Y 404 can each independently be a single bond (eg, a covalent bond or a coordination bond), *-O-*', *-S-*', *-C(R 407 )(R 408 )-*'、*-Si(R 407 )(R 408 )-*'、*-B(R 407 )-*'、*-N(R 407 )-*' or *-P(R 407 )-*',
[0255] * in Formula 402A to Formula 402D 1 ,* 2 ,* 3 and* 4 Each indicates the same as M in formula 401A 401 The bonding site of
[0256] R 401 To R 408 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted by at least one R 10a Substituted C 1 -C60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio, -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),
[0257] R 401 To R 408 may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C 5 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0258] b401 to b404 may each independently be an integer selected from 0 to 10,
[0259] * and *' each indicate a bonding site to an adjacent atom, and
[0260] Q 1 To Q 3 and R 10a Each may be the same as described herein.
[0261] In an embodiment, the compound represented by Formula 401A may be a carbene complex.
[0262] As used herein, the term "carbene complex" may be a complex including a metal and a ligand bonded to the metal, wherein at least one bond between the metal and the ligand is a bond between the metal and a carbon atom of the carbene moiety.
[0263] In an embodiment, the sensitizer may include a compound represented by Formula 401A.
[0264] In an embodiment, the third compound may be one of Compound PD1 to Compound PD41, but the embodiment is not limited thereto:
[0265]
[0266]
[0267]
[0268] In an embodiment, R in Formula 301-1A and Formula 301-2A 301 To R 303 , R 304a To R 306a , R 304b To R 306b and R 311 To R 314 , R in Formula 302 321 To R 326 and R in Formula 401A and Formula 402A to Formula 402D 401 To R 408 Can be independently:
[0269] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy;
[0270] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof;
[0271] each unsubstituted or substituted by cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10 Alkylphenyl, naphthyl, tetrahydronaphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl , acridinyl, phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C 1 -C 10Alkylphenyl, naphthyl, tetrahydronaphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, thiadiazolyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azadibenzothiophenyl, -Si(Q) 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0272] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),and
[0273] Q 1 To Q 3 and Q 31 To Q 33 Each may be the same as described herein.
[0274] In an embodiment, R in Formula 301-1A and Formula 301-2A 301 To R 303 , R 304a To R 306a , R 304b To R 306b and R 311 To R 314 , R in Formula 302 321 To R 326 and R in Formula 401A and Formula 402A to Formula 402D 401 To R 408 Can be independently:
[0275] Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy;
[0276] A group represented by one of Formulae 9-1 to 9-61 or a group represented by one of Formulae 10-1 to 10-348; or
[0277] -C(Q 1 )(Q 2 )(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ):
[0278]
[0279]
[0280]
[0281]
[0282]
[0283]
[0284]
[0285]
[0286]
[0287] In Formulae 9-1 to 9-61 and 10-1 to 10-348, * indicates a bonding site to an adjacent atom, Ph represents a phenyl group, TMS represents a trimethylsilyl group, and D represents a deuterium atom, and
[0288] Q 1 To Q 3 Each may be the same as described herein.
[0289] In embodiments, the electron transport region of the light emitting device may include a hole blocking layer, wherein the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. In embodiments, the hole blocking layer may contact (eg, directly contact) the emission layer.
[0290] In an embodiment, the light emitting device may include a capping layer outside the first electrode or outside the second electrode.
[0291] In an embodiment, the light-emitting device may further include at least one of a first capping layer outside the first electrode and a second capping layer outside the second electrode, wherein the organic metal compound represented by Formula 1 may be included in at least one of the first capping layer and the second capping layer. The first capping layer and / or the second capping layer may each be the same as described herein.
[0292] In an embodiment, the light emitting device may include:
[0293] A first capping layer, outside the first electrode and including an organic metal compound represented by Formula 1;
[0294] a second capping layer, outside the second electrode and including an organic metal compound represented by Formula 1; or
[0295] A first capping layer and a second capping layer.
[0296] In the specification, the expression "(the interlayer and / or the capping layer) includes the organic metal compound represented by Formula 1" as used herein may be understood as "(the interlayer and / or the capping layer) may include one kind of organic metal compound represented by Formula 1 or two or more different kinds of organic metal compounds each represented by Formula 1".
[0297] In an embodiment, the interlayer and / or the capping layer may include only Compound 1 as the organic metal compound represented by Formula 1. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In an embodiment, the interlayer may include Compound 1 and Compound 2 as the organic metal compound represented by Formula 1. In this regard, Compound 1 and Compound 2 may be present in the same layer (for example, Compound 1 and Compound 2 may both be present in the emission layer), or may be present in different layers (for example, Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
[0298] In the specification, the term "interlayer" may be a single layer and / or a plurality of layers between a first electrode and a second electrode of a light emitting device.
[0299] Another embodiment provides an electronic device that may include a light emitting device. The electronic device may further include a thin film transistor. For example, in an embodiment, the electronic device may further include: a thin film transistor including a source electrode and a drain electrode, wherein the first electrode of the light emitting device may be electrically connected to the source electrode or the drain electrode. In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. Further details about the electronic device may be the same as described herein.
[0300] Another embodiment provides an electronic device that may include a light emitting device. The electronic device may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a phone, a mobile phone, a tablet computer, a phablet, 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 display, an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, or a sign.
[0301] [ Figure 1 Description]
[0302] Figure 1 1 is a schematic cross-sectional view of a light emitting device 10 according to an embodiment. The light emitting device 10 includes a first electrode 110 , an interlayer 130 , and a second electrode 150 .
[0303] Below, we will refer to Figure 1 A structure of a light emitting device 10 and a method of manufacturing the light emitting device 10 according to an embodiment are described.
[0304] [First electrode 110]
[0305] exist Figure 1 In the embodiment, a substrate may be further included under the first electrode 110 or on the second electrode 150. In an embodiment, the substrate may be a glass substrate or a plastic substrate. In an embodiment, the substrate may be a flexible substrate and may include plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0306] The first electrode 110 may be formed, for example, by 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 injection of holes.
[0307] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In an embodiment, when the first electrode 110 is a transmissive electrode, a material for forming 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 an embodiment, 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.
[0308] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a triple-layer structure of ITO / Ag / ITO.
[0309] [Interlayer 130]
[0310] The interlayer 130 may be disposed on the first electrode 110. The interlayer 130 may include an emission layer.
[0311] The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150 .
[0312] In addition to various organic materials, the interlayer 130 may further include metal-containing compounds (such as organic metal compounds) and inorganic materials (such as quantum dots), etc.
[0313] In an embodiment, the interlayer 130 may include two or more emission units sequentially stacked between the first electrode 110 and the second electrode 150, and at least one charge generation layer may be respectively between adjacent emission units among the two or more emission units. When the interlayer 130 includes two or more emission units and at least one charge generation layer, the light-emitting device 10 may be a tandem light-emitting device.
[0314] [Hole Transport Region in Interlayer 130]
[0315] The hole transport region may have a single-layer structure composed of a single layer (composed of a single material), a single-layer structure composed of a single layer including different materials, or a multi-layer structure including a plurality of layers including different materials.
[0316] 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.
[0317] In an embodiment, 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 layers of each structure may be stacked from the first electrode 110 in the order of their respective descriptions, but the structure of the hole transport region is not limited thereto.
[0318] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0319] [Formula 201]
[0320]
[0321] [Formula 202]
[0322]
[0323] In equation 201 and equation 202,
[0324] L 201 To L 204 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0325] L 205Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or replaced by at least one R 10a Substituted C 1 -C 20 Alkylene, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 20 Alkenylene, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0326] xa1 to xa4 may each independently be an integer selected from 0 to 5,
[0327] xa5 may be an integer selected from 1 to 10,
[0328] R 201 To R 204 and Q 201 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0329] R 201 and R 202 may be optionally substituted by a single bond, unsubstituted or by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 The alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60 Polycyclic groups (e.g., carbazole groups, etc.) (e.g., compound HT16, etc.),
[0330] R 203 and R 204 may be optionally substituted by a single bond, unsubstituted or by at least one R 10a Substituted C 1 -C 5 Alkylene is either unsubstituted or substituted with at least one R 10a Substituted C2 -C 5 The alkenylene groups are connected to each other to form an unsubstituted or substituted R 10a Substituted C 8 -C 60 polycyclic groups, and
[0331] na1 may be an integer selected from 1 to 4.
[0332] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may include at least one of the groups represented by Formulas CY201 to CY217:
[0333]
[0334] In formula CY201 to formula CY217, R 10b and R 10c Can be independently compared with the 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.
[0335] In an embodiment, in Formula CY201 to Formula CY217, ring CY 201 To Ring CY 204 Each independently may be phenyl, naphthyl, phenanthryl or anthracenyl.
[0336] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may include at least one of the groups represented by Formulas CY201 to CY203.
[0337] In an embodiment, the compound represented by Formula 201 may include at least one of the groups represented by Formulas CY201 to CY203 and at least one of the groups represented by Formulas CY204 to CY217.
[0338] In an embodiment, in Formula 201, xa1 may be 1, R 201 may be one of 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.
[0339] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the groups represented by Formula CY201 to Formula CY203.
[0340] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the groups represented by Formula CY201 to Formula CY203, and may each independently include at least one of the groups represented by Formula CY204 to Formula CY217.
[0341] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the groups represented by Formula CY201 to Formula CY217.
[0342] In an embodiment, the hole transport region may include one of compounds HT1 to 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:
[0343]
[0344]
[0345]
[0346]
[0347] The thickness of the hole transport region may be about to about For example, the thickness of the hole transport region may be in the range of about to about For example, 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 and the thickness of the hole transport layer may be in the range of about to about For example, the thickness of the hole injection layer may be in the range of about to about For example, the thickness of the hole transport layer may be in the range of about to about When the thickness of the hole transport region, the thickness of the hole injection layer, and the thickness of the hole transport layer are within any of the above ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0348] The emission auxiliary layer can increase the luminous efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer can block 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.
[0349] [p-dopant]
[0350] In addition to the above materials, the hole transport region may further include a charge generation material for improvement of conductive characteristics. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region (eg, in the form of a single layer composed of the charge generation material).
[0351] The charge generating material may be, for example, a p-dopant.
[0352] In an embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of less than or equal to about −3.5 eV.
[0353] In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including the element EL1 and the element EL2, or any combination thereof.
[0354]
[0355] Examples of the quinone derivative may include TCNQ, F4-TCNQ, and the like.
[0356] Examples of the cyano group-containing compound may include HAT-CN and a compound represented by Formula 221, and the like:
[0357]
[0358] [Formula 221]
[0359]
[0360] In formula 221,
[0361] R 221 To R 223 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1-C 60 a heterocyclic group, and
[0362] R 221 To R 223 At least one of them may be independently C each substituted by 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group: cyano; -F; -Cl; -Br; -I; C substituted by cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof.
[0363] In a compound including an element EL1 and an 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.
[0364] Examples of metals may include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), 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), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); late transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); and 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), lutetium (Lu), etc.), etc.
[0365] Examples of metalloids may include silicon (Si), antimony (Sb), tellurium (Te), and the like.
[0366] Examples of non-metal may include oxygen (O) and halogen (eg, F, Cl, Br, I, etc.), and the like.
[0367] Examples of compounds including element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or any combination thereof.
[0368] Examples of metal oxides may include tungsten oxides (eg, WO, W 2 O 3 , WO 2 , WO 3 , W 2 O 5 etc.), vanadium oxides (e.g., VO, V 2 O 3 , VO 2 、V 2 O 5 etc.), molybdenum oxides (e.g., MoO, Mo 2 O 3 、MoO 2 、MoO 3 、Mo 2 O 5 etc.) and rhenium oxides (e.g., ReO 3 etc.
[0369] Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, and the like.
[0370] 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, CsI, and the like.
[0371] 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 BaI 2 wait.
[0372] Examples of transition metal halides may include titanium halides (eg, TiF4 、TiCl 4 、TiBr 4 、TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 , ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 , HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3 , VBr 3 VI 3 etc.), niobium halides (e.g., NbF 3 、NbCl 3 , NbBr 3 , NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 、TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 、MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 , WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2 、MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl 2 、TcBr 2 , TcI 2 etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 、ReI 2 etc.), ferrous halides (e.g., FeF 2 、FeCl 2 , FeBr 2,FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 , RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 , OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 、CoI 2 etc.), rhodium halides (e.g., RhF 2 , RhCl 2 , RhBr 2 , RhI 2 etc.), iridium halides (e.g., IrF 2 、IrCl 2 ,IrBr 2 ,IrI 2 etc.), nickel halides (e.g., NiF 2 、NiCl 2 、NiBr 2 , NiI 2 etc.), palladium halides (e.g., PdF 2 , PdCl 2 , PdBr 2 , PdI 2 etc.), platinum halides (e.g., PtF 2 、PtCl 2 , PtBr 2 , PtI 2 etc.), cuprous halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), and gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.), etc.
[0373] Examples of late transition metal halides may include zinc halides (eg, ZnF 2 、ZnCl 2 、ZnBr 2 、ZnI 2 etc.), indium halides (e.g., InI 3 etc.) and tin halides (e.g., SnI 2 etc.
[0374] Examples of lanthanide metal halides may include YbF, YbF 2 , YbF 3 、SmF3 , YbCl, YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3 and SmI 3 wait.
[0375] Examples of metalloid halides may include antimony halides (eg, SbCl 5 etc.
[0376] Examples of metal tellurides may include alkali metal tellurides (eg, Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te, Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, 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, Au 2 Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.), and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), etc.
[0377] [Emitting layer in interlayer 130]
[0378] When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer according to the sub-pixel. In an embodiment, 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, wherein the two or more layers may contact each other or may be separated from each other to emit white light. In an embodiment, 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, wherein the two or more materials may be mixed with each other in a single layer to emit white light.
[0379] In an embodiment, the emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0380] The amount of the dopant in the emission layer may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
[0381] In an embodiment, the emissive layer may include quantum dots.
[0382] In an embodiment, the emission layer may include a delayed fluorescent material. The delayed fluorescent material may be used as a host or a dopant in the emission layer.
[0383] The thickness of the emission layer can be about to about For example, the thickness of the emission layer may be in the range of about to about When the thickness of the emission layer is within any of the above ranges, excellent light emitting characteristics can be obtained without significantly increasing the driving voltage.
[0384] [main body]
[0385] The host may further include a compound represented by Formula 301:
[0386] [Formula 301]
[0387] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0388] In formula 301,
[0389] Ar 301 and L 301 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10aSubstituted C 1 -C 60 Heterocyclic group,
[0390] xb11 can be 1, 2 or 3,
[0391] xb1 may be an integer selected from 0 to 5,
[0392] R 301 It may be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted 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 ),
[0393] xb21 may be an integer selected from 1 to 5, and
[0394] Q 301 To Q 303 Can be independently compared with reference Q 1 Same as described.
[0395] In an embodiment, in Formula 301, when xb11 is 2 or greater, two or more Ar 301 Can be connected to each other via a single bond.
[0396] In an embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0397] [Formula 301-1]
[0398]
[0399] [Formula 301-2]
[0400]
[0401] In Formula 301-1 and Formula 301-2,
[0402] Ring A 301 To Ring A 304 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0403] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0404] xb22 and xb23 can each independently be 0, 1 or 2,
[0405] L 301 , xb1 and R 301 may each be the same as described herein,
[0406] L 302 To L 304 Can be independently compared with reference L 301 Same as described,
[0407] xb2 to xb4 may each independently be the same as described with reference to xb1, and
[0408] R 302 To R 305 and R 311 To R 314 Can be independently compared with the reference R 301 Same as described.
[0409] In an embodiment, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. For example, the host may include a Be complex (eg, compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0410] In an embodiment, the host may include one of Compounds H1 to 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-butyl-anthracene (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:
[0411]
[0412]
[0413]
[0414]
[0415]
[0416]
[0417]
[0418] [Phosphorescent dopant]
[0419] The phosphorescent dopant may include at least one transition metal as a central metal.
[0420] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0421] The phosphorescent dopant may be electrically neutral.
[0422] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0423] [Formula 401]
[0424] M(L 401 ) xc1 (L 402 ) xc2 ,
[0425] In formula 401,
[0426] M may be a transition metal (e.g., 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)),
[0427] L 401 may be a ligand represented by Formula 402, and xc1 may be 1, 2 or 3, wherein when xc1 is 2 or greater, two or more L 401 may be the same or different from each other,
[0428] L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3 or 4, wherein when xc2 is 2 or greater, two or more L 402 may be the same or different from each other,
[0429] [Formula 402]
[0430]
[0431] In formula 402,
[0432] X 401 and X 402 can be independently N or C,
[0433] Ring A 401 and Ring A 402 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0434] T 401 It can 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=*',
[0435] X 403 and X 404 can be independently a chemical bond (e.g., a covalent bond or a coordination bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q414 ),
[0436] Q 411 To Q 414 Can be independently compared with reference Q 1 Same as described,
[0437] R 401 and R 402 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 20 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted 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 ),
[0438] Q 401 To Q 403 Can be independently compared with reference Q 1 Same as described,
[0439] xc11 and xc12 may each independently be an integer selected from 0 to 10, and
[0440] * and *' in Formula 402 each indicate a bonding site to M in Formula 401.
[0441] In an embodiment, in formula 402, X 401 may be nitrogen and X 402 Can be carbon, or X 401 and X 402 Each may be nitrogen.
[0442] In an embodiment, in Formula 401, when xc1 is 2 or greater, two or more L 401 The two rings A 401 Optionally, T as a linker 402 connected to each other, or two or more L 401 The two rings A 402 Optionally, T as a linker 403 Connected to each other (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 Can be independently compared with reference T 401 Same as described.
[0443] In formula 401, L 402 It can be an organic ligand. For example, L 402 It may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), -C(=O), an isonitrile group, a -CN group, a phosphorus-containing group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.
[0444] The phosphorescent dopant may include, for example, one of Compound PD1 to Compound PD39 or any combination thereof:
[0445]
[0446]
[0447]
[0448] [Fluorescent dopant]
[0449] The fluorescent dopant may include an amine-containing compound, a styryl-containing compound, or any combination thereof.
[0450] In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:
[0451] [Formula 501]
[0452]
[0453] In formula 501,
[0454] Ar 501 , L 501 To L 503 , R 501 and R 502 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R10a Substituted C 1 -C 60 Heterocyclic group,
[0455] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0456] xd4 can be 1, 2, 3, 4, 5 or 6.
[0457] In an embodiment, in Formula 501, Ar 501 It may be a condensed ring group in which three or more monocyclic groups are condensed to each other (for example, anthracenyl, 1,2-triphenylenyl, pyrenyl, etc.).
[0458] In an embodiment, in formula 501, xd4 may be 2.
[0459] In an embodiment, the fluorescent dopant may include one of Compound FD1 to Compound FD37, DPVBi, DPAVBi, or any combination thereof:
[0460]
[0461]
[0462]
[0463] [Delayed fluorescence material]
[0464] In an embodiment, the emission layer may include a delayed fluorescent material.
[0465] The delayed fluorescence material described herein may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0466] The delayed fluorescent material included in the emission layer may serve as a host or a dopant depending on the types of other materials included in the emission layer.
[0467] In an embodiment, 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 in the range of about 0 eV to about 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 is within the above range, up-conversion of the delayed fluorescent material from the triplet state to the singlet state may effectively occur, and therefore, the light emitting device 10 may have improved luminous efficiency.
[0468] In an embodiment, the delayed fluorescent material may include: at least one electron donating group (eg, a π-electron-rich C 3 -C 60Cyclic groups (e.g., carbazolyl), etc.) and at least one electron-withdrawing group (e.g., sulfoxide, cyano, π-electron-deficient nitrogen-containing C 1 -C 60 or a material including C wherein two or more cyclic groups are fused while sharing boron (B). 8 -C 60 Materials with polycyclic groups, etc.
[0469] Examples of the delayed fluorescent material may include at least one of Compound DF1 to Compound DF14 or Compound DFD1 to Compound DFD29:
[0470]
[0471]
[0472]
[0473] [Quantum dot]
[0474] In an embodiment, the emissive layer may include quantum dots.
[0475] In the specification, a quantum dot may be a crystal of a semiconductor compound, and may include any material capable of emitting light of various emission wavelengths according to the size of the crystal.
[0476] The diameter of a quantum dot can, for example, be in the range of about 1 nm to about 10 nm.
[0477] The quantum dots may be synthesized by a wet chemical process, a metal organic chemical vapor deposition (MOCVD) process, a molecular beam epitaxy (MBE) process, or any process similar thereto.
[0478] The wet chemical process is a method including mixing a precursor material with an organic solvent and growing a quantum dot particle crystal. When the quantum dot particle crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot particle crystal, and controls the growth of the quantum dot particle crystal so that the growth of the quantum dot particle crystal can be controlled by a process that is low in cost and easy to perform than a vapor deposition method (such as a metal organic chemical vapor deposition (MOCVD) process or a molecular beam epitaxy (MBE) process).
[0479] Quantum dots may include: Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; Group IV elements or compounds; or any combination thereof.
[0480] Examples of II-VI semiconductor compounds may include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, Cd ZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe and MgZnS, etc.; quaternary compounds, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and HgZnSTe, etc.; or any combination thereof.
[0481] Examples of III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and InAlPSb, etc.; or any combination thereof. In an embodiment, the III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including the Group II element may include InZnP, InGaZnP, InAlZnP, and the like.
[0482] Examples of III-VI semiconductor compounds may include binary compounds such as GaS, GaSe, Ga 2 Se 3 、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 and InTe, etc.; ternary compounds, such as InGaS 3 and InGaSe 3 etc.; or any combination thereof.
[0483] Examples of Group I-III-VI semiconductor compounds may include: ternary compounds such as AgInS, AgInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 and AgAlO 2 etc.; or any combination thereof.
[0484] Examples of Group IV-VI semiconductor compounds may include: binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe and PbTe; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe and SnPbTe; quaternary compounds, such as SnPbSSe, SnPbSeTe and SnPbSTe; or any combination thereof.
[0485] Examples of Group IV elements or compounds may include: single element materials such as Si and Ge, etc.; binary compounds such as SiC and SiGe, etc.; or any combination thereof.
[0486] Each element included in the multi-element compound such as a binary compound, a ternary compound, and a quaternary compound may exist in the particle at a uniform concentration or in a non-uniform concentration.
[0487] In an embodiment, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is uniform, or the quantum dot may have a core-shell structure. In an embodiment, a material included in the core and a material included in the shell may be different from each other.
[0488] The shell of the quantum dot can be used as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties, and / or can be used as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be monolayer or multilayer. The interface between the core and the shell can have a concentration gradient in which the concentration of the material present in the shell decreases toward the center of the core.
[0489] Examples of materials forming the shell of quantum dots may include metal oxides, metalloid oxides or non-metal oxides, semiconductor compounds or any combination thereof. Examples of metal oxides, metalloid oxides or non-metal oxides may include: binary compounds, such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 and NiO, etc.; ternary compounds, such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 and CoMn 2 O 4 etc.; or any combination thereof. Examples of semiconductor compounds may include: Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; or any combination thereof. Examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0490] The quantum dot may have a full width at half maximum (FWHM) of an emission wavelength spectrum less than or equal to about 45 nm. For example, the quantum dot may have a FWHM of an emission wavelength spectrum less than or equal to about 40 nm. For example, the quantum dot may have a FWHM of an emission wavelength spectrum less than or equal to about 30 nm. When the FWHM of the quantum dot is within any of these ranges, the quantum dot may have improved color purity or improved color reproducibility. Light emitted by the quantum dot may be emitted in all directions, so that a wide viewing angle may be improved.
[0491] In embodiments, the quantum dots may be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, or the like.
[0492] Because the energy band gap can be adjusted by controlling the size of the quantum dots, light with various wavelength bands can be obtained from the quantum dot emission layer. Accordingly, by using quantum dots of different sizes, a light emitting device that emits light of various wavelength bands can be implemented. In an embodiment, the size of the quantum dots can be selected to emit red light, green light, and / or blue light. The size of the quantum dots can be configured to emit white light through a combination of various colors of light.
[0493] [Electron Transport Region in Interlayer 130]
[0494] The electron transport region may have a single-layer structure composed of a single layer (composed of a single material), a single-layer structure composed of a single layer including different materials, or a multi-layer structure including a plurality of layers including different materials.
[0495] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0496] In an embodiment, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the layers of each structure may be stacked from the emission layer in the order described in their respective descriptions, but the structure of the electron transport region is not limited thereto.
[0497] In an embodiment, the electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic group.
[0498] In an embodiment, the electron transport region may include a compound represented by Formula 601:
[0499] [Formula 601]
[0500] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0501] In formula 601,
[0502] Ar 601 and L 601 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0503] xe11 can be 1, 2 or 3,
[0504] xe1 can be 0, 1, 2, 3, 4 or 5,
[0505] R 601 may be unsubstituted or substituted with at least one R 10a Substituted C3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted 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 ),
[0506] Q 601 To Q 603 Can be independently compared with reference Q 1 Same as described,
[0507] xe21 can be 1, 2, 3, 4, or 5, and
[0508] Ar 601 , L 601 and R 601 At least one of them may be independently unsubstituted or substituted by at least one R 10a Substituted π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic group.
[0509] In an embodiment, in Formula 601, when xe11 is 2 or greater, two or more Ar 601 Can be connected to each other via a single bond.
[0510] In an embodiment, in Formula 601, Ar 601 may be unsubstituted or substituted with at least one R 10a Substituted anthracenyl.
[0511] In an embodiment, the electron transport region may include a compound represented by Formula 601-1:
[0512] [Formula 601-1]
[0513]
[0514] In formula 601-1,
[0515] 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 614To X 616 At least one of them may each be N,
[0516] L 611 To L 613 Can be independently compared with reference L 601 Same as described,
[0517] xe611 to xe613 can each independently be the same as described with reference to xe1,
[0518] R 611 To R 613 Can be independently compared with the reference R 601 Same as described, and
[0519] 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 Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0520] In an embodiment, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
[0521] In an embodiment, the electron transport region may include: one of 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:
[0522]
[0523]
[0524]
[0525]
[0526] The thickness of the electron transport region can be about to about For example, the thickness of the electron transport region may be in the range of about to about When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be independently about to about and the thickness of the electron transport layer can be in the range of about to about For example, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be independently about to about For example, the thickness of the electron transport layer may be in the range of about to about When the thickness of the buffer layer, the thickness of the hole blocking layer, the thickness of the electron control layer, the thickness of the electron transport layer and / or the thickness of the electron transport region are within the above ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.
[0527] The electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material in addition to the above-mentioned materials.
[0528] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0529] In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) or compound ET-D2:
[0530]
[0531] 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 contact (eg, directly contact) the second electrode 150.
[0532] The electron injection layer may have a single-layer structure composed of a single layer (composed of a single material), a single-layer structure composed of a single layer including different materials, or a multilayer structure including a plurality of layers including different materials.
[0533] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0534] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0535] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may be oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.) or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
[0536] The alkali metal compound may include: alkali metal oxides, such as Li 2 O, Cs 2 O, and K 2 O, etc.; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and KI, etc.; or any combination thereof. The alkaline earth metal compound may include alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1) and Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1), etc. The rare earth metal 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 an embodiment, the rare earth metal compound may include lanthanide metal tellurides. Examples of lanthanide metal tellurides may include 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 Te3 、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 , Yb 2 Te 3 He Lu 2 Te 3 wait.
[0537] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include an alkali metal ion, an alkaline earth metal ion or a rare earth metal ion and a ligand bonded to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.
[0538] In an embodiment, the electron injection layer may be composed of the following: 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 above. In an embodiment, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
[0539] In an embodiment, the electron injection layer may be composed of an alkali metal compound (e.g., an alkali metal halide); or the electron injection layer may be composed of an alkali metal compound (e.g., an alkali metal halide) and 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, a LiF:Yb co-deposition layer, and the like.
[0540] When the electron injection layer further 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 may be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0541] The thickness of the electron injection layer can be about to about For example, the thickness of the electron injection layer may be about to about When the thickness of the electron injection layer is within any of the above ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0542] [Second electrode 150]
[0543] The second electrode 150 may be disposed on the interlayer 130 having the structure as described above. The second electrode 150 may be a cathode as an electron injection electrode. When the second electrode 150 is a cathode, the material used to form the second electrode 150 may include a material having a low work function, such as a metal, an alloy, an electrically conductive compound, or any combination thereof.
[0544] 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.
[0545] The second electrode 150 may have a single-layer structure or a multi-layer structure.
[0546] [Capping layer]
[0547] The light emitting device 10 may include a first capping layer outside the first electrode 110 and / or a second capping layer outside the second electrode 150. In an embodiment, the light emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked in the order described, a structure in which the first electrode 110, the interlayer 130, the second electrode 150 and the second capping layer are stacked in the order described, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150 and the second capping layer are stacked in the order described.
[0548] The light generated in the emission layer of the interlayer 130 of the light emitting device 10 can be extracted toward the outside through the first electrode 110 (which can be a semi-transmissive electrode or a transmissive electrode) and through the first capping layer. The light generated in the emission layer of the interlayer 130 of the light emitting device 10 can be extracted toward the outside through the second electrode 150 (which can be a semi-transmissive electrode or a transmissive electrode) and through the second capping layer.
[0549] The first capping layer and the second capping layer can each increase the external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light emitting device 10 is increased, so that the light emitting efficiency of the light emitting device 10 can be improved.
[0550] The first capping layer and the second capping layer may each include a material having a refractive index greater than or equal to about 1.6 (with respect to a wavelength of about 589 nm).
[0551] 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 material capping layer including an organic material and an inorganic material.
[0552] At least one of the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine-containing compound may each be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amine-containing compound.
[0553] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof.
[0554] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include one of compounds HT28 to HT33, one of compounds CP1 to CP6, β-NPB, or any combination thereof:
[0555]
[0556] [membrane]
[0557] The organometallic compound represented by Formula 1 may be included in various films. Accordingly, another embodiment provides a film including the organometallic compound represented by Formula 1. The film may be, for example, an optical member (or light control device) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarization layer, a quantum dot content layer, etc.), a light blocking member (e.g., a light reflection layer, a light absorption layer, etc.) or a protective member (e.g., an insulating layer, a dielectric layer, etc.), etc.
[0558] [Electronic equipment]
[0559] The light emitting device may be included in various electronic devices. For example, the electronic device including the light emitting device may be a light emitting device, an authentication device, and the like.
[0560] In addition to the light emitting device, the electronic device (e.g., light emitting device) may further include a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and / or the color conversion layer may be arranged in at least one direction of travel 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 light emitting device may be the same as described herein. In an embodiment, the color conversion layer may include quantum dots. The quantum dots may be, for example, quantum dots as described herein.
[0561] 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 plurality of sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixel regions.
[0562] A pixel defining layer may be disposed between the plurality of sub-pixel regions to define each sub-pixel region.
[0563] The color filter may further include a plurality of color filter regions and a plurality of light shielding patterns arranged between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a plurality of light shielding patterns arranged between the plurality of color conversion regions.
[0564] The plurality of color filter regions (or the 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 from each other. In an embodiment, 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, the plurality of color filter regions (or the plurality of color conversion regions) may include quantum dots. In an embodiment, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. The quantum dots may be the same as the quantum dots described herein. The first region, the second region, and / or the third region may each further include a scatterer.
[0565] In an embodiment, 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. The first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths from each other. In an embodiment, 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.
[0566] In addition to the above-mentioned light emitting device, 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.
[0567] The thin film transistor may further include a gate electrode, a gate insulating film, and the like.
[0568] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and the like.
[0569] 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 allows light from the light emitting device to be extracted to the outside, and may prevent 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.
[0570] 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 further included on the sealing portion. Examples of the functional layer may include a touch screen layer and a polarization 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 using biometric information of a living body (e.g., a fingertip, a pupil, etc.).
[0571] In addition to the light emitting device as described above, the authentication device may further include a biometric information collector.
[0572] The electronic device can be applied to various displays, light sources, lighting devices, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical tools (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various measuring tools, instruments (e.g., instruments for vehicles, aircraft, and ships), projectors, and the like.
[0573] [ Figure 2 and Figure 3 Description]
[0574] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment.
[0575] Figure 2 The electronic device (eg, a light emitting device) includes a substrate 100, a thin film transistor (TFT), a light emitting device, and a packaging portion 300 that seals the light emitting device.
[0576] 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 penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
[0577] 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.
[0578] The active layer 220 may include an inorganic semiconductor (eg, silicon or polysilicon), an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0579] 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 .
[0580] The 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 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
[0581] Source electrode 260 and drain electrode 270 may be disposed on interlayer insulating film 250. Interlayer insulating film 250 and gate insulating film 230 may be formed to expose source and drain regions of active layer 220, and source electrode 260 and drain electrode 270 may contact exposed portions of the source and drain regions of active layer 220, respectively.
[0582] 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 provided on the passivation layer 280. The light emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
[0583] The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270, and may expose a portion of the drain electrode 270. The first electrode 110 may be electrically connected to the exposed portion of the drain electrode 270.
[0584] 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 region of the first electrode 110, and the interlayer 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. Figure 2 2 , but at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 and be provided in the form of a common layer.
[0585] The second electrode 150 may be disposed on the interlayer 130, and the capping layer 170 may be further included on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0586] The encapsulation part 300 may be disposed on the capping layer 170. The encapsulation part 300 may be disposed on the light emitting device to prevent the light emitting device from being affected by 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; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), epoxy resin (e.g., aliphatic glycidyl ether (AGE)), etc.) or any combination thereof; or any combination of an inorganic film and an organic film.
[0587] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment.
[0588] Figure 3 An electronic device (eg, a light emitting device) may be used with Figure 2 The electronic device is different from the electronic device of the present invention in that at least the encapsulation portion 300 further includes a light shielding pattern 500 and a functional area 400. The functional area 400 may be a color filter area, a color conversion area, or a combination of a color filter area and a color conversion area. In an embodiment, Figure 3 The light-emitting device included in the electronic device may be a series light-emitting device.
[0589] [ Figure 4 Description]
[0590] Figure 4 1 is a schematic perspective view of an electronic device 1 including a light-emitting device according to an embodiment. The electronic device 1, which is a device for displaying moving images or still images, may not only 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 computer, an e-book, a portable multimedia player (PMP), a navigation device or an ultra-mobile personal computer (UMPC), but may also be various 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 any product as described above or a part thereof. The electronic device 1 may be a wearable device, such as a smart watch, a watch phone, a glasses-type display or a head-mounted display (HMD), or a part of a wearable device. However, the embodiment is not limited thereto.
[0591] For example, the electronic device 1 may be a dashboard of a vehicle, a center console of a vehicle, a center information display (CID) arranged on the dashboard of a vehicle, an interior mirror display replacing a side mirror of a vehicle, an entertainment display for a rear seat of a vehicle, a display arranged on a backrest of a front seat, a head-up display (HUD) installed in front of the vehicle or projected on a front windshield, or a computer generated hologram augmented reality head-up display (CGH AR HUD). For convenience of explanation, Figure 4 An embodiment is explained in which the electronic device 1 is a smart phone.
[0592] 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 implement an image through a two-dimensional pixel array arranged in the display area DA.
[0593] The non-display area NDA may be an area where no image is displayed, and may surround the display area DA. A driver for providing an electrical signal or power to a display element arranged in the display area DA may be arranged in the non-display area NDA. A pad that may be electrically connected to an electronic element or a printed circuit board may be arranged in the non-display area NDA.
[0594] In the electronic device 1, the length in the x-axis direction and the length in the y-axis direction may be different from each other. Figure 4 As shown in , the length in the x-axis direction may be shorter than the length in the y-axis direction. In an embodiment, the length in the x-axis direction may be the same as the length in the y-axis direction. In an embodiment, the length in the x-axis direction may be longer than the length in the y-axis direction.
[0595] [ Figure 5 and FIG. 6A to FIG. 6C Description]
[0596] Figure 5 is a schematic perspective view of the exterior of a vehicle 1000 as an electronic device including a light emitting device according to an embodiment. FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of vehicle 1000 according to an embodiment.
[0597] refer to Figure 5 , Fig. 6A , Figure 6B and Figure 6C , embodiments of the vehicle 1000 may include various devices for moving an object to be transported (e.g., a person, an object, or an animal) from a starting point to a destination. Examples of the vehicle 1000 may include a vehicle traveling on roads or tracks, a ship moving on the sea or a river, and an airplane flying in the air using the action of air.
[0598] The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in one direction (e.g., a predetermined or selectable direction) according to the rotation of at least one wheel. Examples of the vehicle 1000 may include a three-wheeled vehicle or a four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover, a bicycle, and a train traveling on a track.
[0599] The vehicle 1000 may include a body having an interior and an exterior, and a chassis as a portion outside the body in which mechanical equipment necessary for driving is installed. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and 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 left and right wheels, etc.
[0600] The vehicle 1000 may include side window glasses 1100 , a front window glass 1200 , side mirrors 1300 , an instrument panel 1400 , a center console 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0601] 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 .
[0602] The side window glass 1100 may be mounted on the side of the vehicle 1000. In an embodiment, 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 may face each other. In an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be arranged adjacent to the instrument panel 1400, and the second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.
[0603] In an embodiment, the side window glass 1100 may be spaced apart from each other in the x-axis direction or in a direction opposite to the x-axis direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x-axis direction or in a direction opposite to the x-axis direction. For example, the imaginary straight line L connecting the side window glass 1100 may extend in the x-axis direction or in a direction opposite to the x-axis 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-axis direction or in a direction opposite to the x-axis direction.
[0604] The front window glass 1200 may be installed at the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.
[0605] The side view mirror 1300 may provide a view of the rear of the vehicle 1000. The side view mirror 1300 may be mounted on the exterior of the vehicle body. In an embodiment, a plurality of side view mirrors 1300 may be provided. Any one of the plurality of side view mirrors 1300 may be arranged outside the first side window glass 1110. Another one of the plurality of side view mirrors 1300 may be arranged outside the second side window glass 1120.
[0606] The instrument panel 1400 may be arranged in front of the steering wheel. The instrument panel 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, a driving recorder, an automatic gear selector indicator light, a door open warning light, an oil warning light, and / or a low fuel warning light.
[0607] The center console 1500 may include a control panel on which buttons for adjusting an audio device, an air conditioning device, and a seat heater are arranged. The center console 1500 may be arranged at one side of the instrument panel 1400 .
[0608] The passenger seat instrument panel 1600 may be spaced apart from the instrument panel 1400, and the center console 1500 is disposed between the passenger seat instrument panel 1600 and the instrument panel 1400. In an embodiment, the instrument panel 1400 may be disposed to correspond to a driver's seat (not shown), and the passenger seat instrument panel 1600 may be disposed to correspond to a passenger seat (not shown). In an embodiment, the instrument panel 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.
[0609] In an embodiment, 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 an embodiment, 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 instrument panel 1400, the center console 1500, and the passenger seat instrument panel 1600.
[0610] The display device 2 may include an organic light-emitting display device, an inorganic light-emitting display device, a quantum dot display device, etc. Hereinafter, an organic light-emitting display device including a light-emitting device according to an embodiment (as a display device 2 according to an embodiment of the present disclosure) will be described as an example. However, various types of display devices as described herein may be used in the embodiments.
[0611] refer to Fig. 6A , the display device 2 may be arranged on the center console 1500. In an embodiment, the display device 2 may display navigation information. In an embodiment, the display device 2 may display information related to audio settings, video settings, or vehicle settings.
[0612] refer to Figure 6B, the display device 2 may be arranged on the instrument panel 1400. When the display device 2 is arranged on the instrument panel 1400, the instrument panel 1400 may display driving information and the like through the display device 2. For example, the instrument panel 1400 may digitally implement driving information. The instrument panel 1400 may digitally display vehicle information and driving information as images. For example, the pointer and instrument of the tachometer and various warning light icons may be displayed through digital signals.
[0613] refer to 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 an embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 may display images related to the information displayed on the instrument panel 1400 and / or the information displayed on the center console 1500. In an embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the instrument panel 1400 and / or the information displayed on the center console 1500.
[0614] [Manufacturing method]
[0615] The layer constituting the hole transport region, the emission layer and the layer constituting the electron transport region can be formed in a selected region by using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing and laser induced thermal imaging.
[0616] 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., about 10 -8 To about 10 -3 Torr in the range of vacuum and about to about Deposition is carried out at a deposition rate within a range of .
[0617] [Definition of terms]
[0618] As used herein, the term “C 3 -C 60 The term "carbocyclic group" may be a cyclic group consisting of only carbon atoms as ring-forming atoms and having 3 to 60 carbon atoms, and as used herein, the term "C 1 -C 60 The "heterocyclic group" may be a cyclic group having 1 to 60 carbon atoms and may further include at least one heteroatom as a ring-constituting atom in addition to the carbon atoms. 3 -C 60 Carbocyclic and C 1 -C60 The heterocyclic groups may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are fused to each other. 1 -C 60 The heterocyclic group can have 3 to 61 ring-forming atoms.
[0619] As used herein, the term "cyclic group" may be C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0620] As used herein, the term "π-electron-rich C 3 -C 60 The "cyclic group" may be a cyclic group having 3 to 60 carbon atoms and may not include *-N=*' as a ring-forming portion. As used herein, the term "π-electron-deficient nitrogen-containing C 1 -C 60 The "cyclic group" may be a heterocyclic group having 1 to 60 carbon atoms and may include *-N=*' as a ring-forming portion.
[0621] In an embodiment,
[0622] C 3 -C 60 The carbocyclic group may be a T1 group or a group in which two or more T1 groups are fused to each other (e.g., cyclopentadienyl, adamantyl, norbornyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylene, perylene, pentaphenanthrenyl, heptalenyl, tetracenyl, phenanthrenyl, hexenyl, pentacenyl, rubenyl, coronenyl, ovalenyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl, or indenoanthryl),
[0623] C 1 -C 60The heterocyclic group may be a T2 group, a group in which two or more T2 groups are fused to each other, or a group in which at least one T2 group and at least one T1 group are fused to each other (e.g., a pyrrolyl group, a thienyl group, a furyl group, an indolyl group, a benzindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzothiorolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzothiorolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an indenocarbazolyl group, an indolcarbazolyl group, a benzofuranocarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiorolocarbazolyl group, a benzoindolcarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthothiorolyl group, a benzofuranodibenzofuranyl group, a benzofuranodibenzothiophenyl ... phenyl, benzothiophene and dibenzothiophene, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl quinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazine, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiopheneyl, azadibenzofuranyl, etc.),
[0624] Pi-electron-rich C 3 -C 60 The cyclic group may be a T1 group, a group in which two or more T1 groups are fused to each other, a T3 group, a group in which two or more T3 groups are fused to each other, or a group in which at least one T3 group and at least one T1 group are fused to each other (e.g., C 3 -C 60 carbocyclic group, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolcarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiolyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, benzothiophenyldibenzothiophenyl, etc.),
[0625] π-electron-deficient nitrogen-containing C 1 -C 60The cyclic group may be a T4 group, a group in which two or more T4 groups are fused to each other, a group in which at least one T4 group and at least one T1 group are fused to each other, a group in which at least one T4 group and at least one T3 group are fused to each other, or a group in which at least one T4 group, at least one T1 group, and at least one T3 group are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, oxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiopheneyl, azadibenzofuranyl, etc.),
[0626] wherein the T1 group can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptane), norbornyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane or phenyl,
[0627] The T2 group can be furanyl, thienyl, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiarolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetraazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl or dihydropyridazinyl,
[0628] The T3 group may be a furyl group, a thienyl group, a 1H-pyrrolyl group, a thiole group or a borocyclopentadienyl group, and
[0629] The T4 group can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathioyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.
[0630] As used herein, the terms "cyclic group", "C 3 -C 60 Carbocyclic group, "C 1 -C 60 Heterocyclic group", "π-electron-rich C 3 -C 60 Cyclic group" or "π-electron-deficient nitrogen-containing C 1 -C 60 The "cyclic group" may each be a group condensed with any cyclic group, a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of the formula using the corresponding term. For example, "phenyl" may be benzo, phenyl or phenylene, etc., which can be easily understood by ordinary technicians in the art based on the structure of the formula including "phenyl".
[0631] Unit Price C 3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 Examples of the heterocyclic group 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 fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group. 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 Examples of the heterocyclic group 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 a heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.
[0632] As used herein, the term “C 1 -C 60The term “alkyl” may be a linear or branched monovalent aliphatic hydrocarbon group having 1 to 60 carbon atoms, and examples thereof may include 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, tert-decyl, and the like. As used herein, the term “C 1 -C 60 The "alkylene" may be 1 -C 60 An alkyl group is a divalent group having the same structure.
[0633] As used herein, the term “C 2 -C 60 The "alkenyl" may be 2 -C 60 The alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end, and examples thereof may include vinyl, propenyl, butenyl, and the like. As used herein, the term “C 2 -C 60 "Alkenylene" can be 2 -C 60 An alkenyl group is a divalent group having the same structure.
[0634] As used herein, the term “C 2 -C 60 "Alkynyl" may be 2 -C 60 The alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end thereof, and examples thereof may include ethynyl and propynyl, etc. As used herein, the term “C 2 -C 60 "Alkyne" can be 2 -C 60 Alkynyl is a divalent group having the same structure.
[0635] As used herein, the term “C 1 -C 60 "Alkoxy" may be -O(A 101 )(where A 101 Can be C 1 -C 60 The monovalent group represented by an alkyl group may include a methoxy group, an ethoxy group, an isopropoxy group, and the like.
[0636] As used herein, the term “C 3 -C 10The term "cycloalkyl" may be a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl, etc. As used herein, the term "Cycloalkyl" may be a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2 3 -C 10 The cycloalkylene group may be 3 -C 10 The cycloalkyl group is a divalent group having the same structure.
[0637] As used herein, the term “C 1 -C 10 The term "heterocycloalkyl" may be a monovalent cyclic group of 1 to 10 carbon atoms further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and examples thereof may include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, tetrahydrothienyl, and the like. 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.
[0638] As used herein, the term “C 3 -C 10 The term "cycloalkenyl" may be 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 may include cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like. As used herein, the term "C 3 -C 10 The cycloalkenylene group may be 3 -C 10 The cycloalkenyl group is a divalent group having the same structure.
[0639] As used herein, the term “C 1 -C 10 The "heterocycloalkenyl group" may be a monovalent cyclic group of 1 to 10 carbon atoms which further includes at least one heteroatom as a ring-constituting atom in addition to carbon atoms in its cyclic structure and has at least one double bond. 1 -C 10 Examples of heterocycloalkenyl groups may include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, 2,3-dihydrothienyl, and the like. As used herein, the term “C 1 -C 10 The heterocycloalkenylene group may be 1 -C 10The heterocycloalkenyl group is a divalent group having the same structure.
[0640] As used herein, the term “C 6 -C 60 The term "aryl" may be a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 The "arylene group" may be a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Examples of aryl groups may include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, heptalenyl, tetracenyl, pyrenyl, hexenyl, pentacene, rubenyl, coronenyl, and ovalenyl. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the respective rings may be fused to each other.
[0641] As used herein, the term “C 1 -C 60 The term "heteroaryl" may be a monovalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms. 1 -C 60 The "heteroarylene group" may be a divalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms. 1 -C 60 Examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, and the like. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the respective rings may be fused to each other.
[0642] As used herein, the term "monovalent non-aromatic fused polycyclic group" may be a monovalent group having two or more rings fused to each other, only carbon atoms as ring atoms, and no aromaticity in its entire molecular structure (e.g., having 8 to 60 carbon atoms). Examples of monovalent non-aromatic fused polycyclic groups may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl, and indenoanthryl, etc. As used herein, the term "divalent non-aromatic fused polycyclic group" may be a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.
[0643] As used herein, the term “monovalent non-aromatic fused heteropolycyclic group” may be a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings fused to each other, further including at least one heteroatom as a ring-constituting atom in addition to carbon atoms, and having non-aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group may include pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothioyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothioyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothioyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl The term "divalent non-aromatic condensed heteropolycyclic group" as used herein may be a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
[0644] As used herein, the term “C 6 -C 60 The "aryloxy" may be -O(A 102 )(where A 102 Can be C 6 -C 60 aryl) and as used herein, the term "C 6 -C 60 The "arylthio" group may be -S(A 103 )(where A 103 Can be C 6 -C60 A group represented by an aryl group.
[0645] As used herein, the term “C 7 -C 60 The "aralkyl" may be -(A 104 )(A 105 )(where A 104 Can be C 1 -C 54 Alkylene, and A 105 Can be C 6 -C 59 aryl) and as used herein, the term "C 2 -C 60 The heteroarylalkyl group may be -(A 106 )(A 107 )(where A 106 Can be C 1 -C 59 Alkylene, and A 107 Can be C 1 -C 59 A group represented by a heteroaryl group.
[0646] In the specification, the group "R 10a " can be:
[0647] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0648] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy: 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 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0649] Each unsubstituted or substituted 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 or C 2 -C 60 Heteroaralkyl: 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 Aralkyl, C 2 -C 60 Heteroaralkyl, -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; or
[0650] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ).
[0651] In the specification, the group Q used herein 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 may be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; pyridyl; pyrimidinyl; pyridazinyl; pyrazinyl; triazinyl; or each is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted 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 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.
[0652] As used herein, the term "heteroatom" may be any atom other than a carbon atom and a hydrogen atom. Examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0653] As used herein, the term "first row transition metal" may include Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, or Zn, etc. As used herein, the term "second row transition metal" may include Y, Zr, Nb, Mo, Tc, Ru, Rh, Pd, Ag, or Cd, etc. As used herein, the term "third row transition metal" may include Hf, Ta, W, Re, Os, Ir, Pt, and Au, etc.
[0654] In the specification, the term "Ph" refers to a phenyl group, the term "Me" refers to a methyl group, the term "Et" refers to an ethyl group, the term "tert-Bu" or "Bu t ” each refers to a tert-butyl group, and the term “OMe” refers to a methoxy group.
[0655] As used herein, the term "biphenyl" may be "phenyl substituted by phenyl". For example, "biphenyl" may be a phenyl having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0656] As used herein, the term "terphenyl" may be a "phenyl group substituted with a biphenyl group". For example, a "terphenyl group" may be a phenyl group substituted with a C 6 -C 60 Aryl substituted C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0657] Unless otherwise defined, the symbols * and *' as used herein each refer to a bonding site to adjacent atoms in the corresponding formula or moiety.
[0658] In the specification, the terms "x-axis", "y-axis", and "z-axis" used herein are not limited to the three axes in an orthogonal coordinate system (e.g., a Cartesian coordinate system), and can be interpreted in a broader sense than the three axes in the aforementioned orthogonal coordinate system. For example, the x-axis, y-axis, and z-axis may describe axes that are orthogonal to each other, or may describe axes in different directions that are not orthogonal to each other.
[0659] Hereinafter, the compound according to the embodiment and the light-emitting device according to the embodiment will be described in detail with reference to Synthesis Examples and Examples. The phrase "using B instead of A" used in describing Synthesis Examples means using B instead of A in the same molar equivalent.
[0660] [Synthesis Examples and Examples]
[0661] Synthesis Example 1 (Compound 1)
[0662]
[0663] Synthesis of intermediate compound 1-A
[0664] (6-Fluoro-4-(methyl-d3)pyridin-3-yl)boric acid (1.2 eq), 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (1.0 eq), tetrakis(triphenylphosphine)palladium(0) (5 mol%) and potassium carbonate (2.0 eq) were dissolved in tetrahydrofuran / H 2 O (2: 1, 1.0M by volume), and the resulting reaction mixture was stirred at 70 ° C for 12 hours. The reaction mixture was cooled at room temperature, and three extraction processes were performed using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound 1-A (yield: 77%).
[0665] Synthesis of intermediate compound 1-B
[0666] The intermediate compound 1-A (1.0 eq), 2-methoxy-9H-carbazole-5,6,7,8-d 4 (1.2eq), copper (I) iodide (10mol%), picolinic acid (20mol%) and cesium carbonate (2.0eq) were dissolved in dimethyl sulfoxide (1.0M), and the resulting reaction mixture was stirred at 100°C for 12 hours. The reaction mixture was cooled at room temperature, and three extraction processes were performed using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound 1-B (yield: 86%).
[0667] Synthesis of intermediate compound 1-C
[0668] Intermediate compound 1-B (1.0 eq) was dissolved in dichloromethane (0.1 M), and tribromide (2.0 eq) was slowly added thereto while stirring at 0 ° C, and the resulting reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with distilled water and neutralized with a 30wt% aqueous sodium hydroxide solution. Three extraction processes were performed using dichloromethane and water to obtain an organic layer. The organic layer obtained was dried and concentrated with magnesium sulfate to synthesize intermediate compound 1-C (yield: 90%).
[0669] Synthesis of intermediate compound 1-D
[0670] Intermediate compound 1-C (1.0 eq), 1,3-dibromobenzene (2.0 eq), copper (I) iodide (0.01 eq), potassium carbonate (2.0 eq) and L-proline (0.02 eq) were dissolved in dimethyl sulfoxide (0.1 M), and the resulting reaction mixture was stirred at 130 ° C for 24 hours. The reaction mixture was cooled at room temperature, and an organic layer was obtained by performing three extraction processes using dichloromethane and water. The obtained organic layer was dried with magnesium sulfate, concentrated, and subjected to column chromatography to obtain intermediate compound 1-D (yield: 82%).
[0671] Synthesis of intermediate compound 1-F
[0672] Intermediate compound 1-D (1.0 eq), intermediate compound 1-E (1.0 eq), Pd 2 (dba) 3 (5.0mol%), Sphos (0.1eq) and sodium tert-butoxide (2.0eq) were dissolved in toluene (0.5M), and the resulting reaction mixture was stirred at 120°C for 4 hours. The reaction mixture was cooled at room temperature, and three extraction processes were performed using dichloromethane and water to obtain an organic layer. The organic layer obtained was dried with magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound 1-F (yield: 81%).
[0673] Synthesis of intermediate compound 1-G
[0674] Intermediate compound 1-F (1.0 eq), triethyl orthoformate (50 eq) and hydrogen chloride (aqueous solution, 12 M, 3.0 eq) were stirred at 80 ° C for 12 hours. The resulting reaction mixture was cooled at room temperature, and three extraction processes were performed using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound 1-G (yield: 82%).
[0675] Synthesis of compound 1
[0676] The intermediate compound 1-G (1.0 eq), Pt(COD)Cl 2 (1.2eq) and sodium acetate (2.0eq) were dissolved in 1,4-dioxane (0.5M), and the resulting reaction mixture was stirred at 120°C for 48 hours. The reaction mixture was cooled at room temperature, and three extraction processes were performed using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried with magnesium sulfate, concentrated, and subjected to column chromatography to synthesize compound 1 (yield: 28%).
[0677] Synthesis Example 2 (Compound 49)
[0678]
[0679] Synthesis of intermediate compound 49-A
[0680] Intermediate compound 49-A (yield: 71%) was synthesized in essentially the same manner as the synthesis of intermediate compound 1-A, except that 5-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (1.0 eq) was used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (1.0 eq).
[0681] Synthesis of intermediate compound 49-B
[0682] Intermediate Compound 49-B was synthesized in substantially the same manner as that of Intermediate Compound 1-B (yield: 79%), except that Intermediate Compound 49-A (1.0 eq) was used instead of Intermediate Compound 1-A (1.0 eq).
[0683] Synthesis of intermediate compound 49-C
[0684] Intermediate Compound 49-C was synthesized in substantially the same manner as that of Intermediate Compound 1-C (yield: 86%), except that Intermediate Compound 49-B (1.0 eq) was used instead of Intermediate Compound 1-B (1.0 eq).
[0685] Synthesis of intermediate compound 49-D
[0686] Intermediate Compound 49-D was synthesized in substantially the same manner as that of Intermediate Compound 1-D (yield: 68%), except that Intermediate Compound 49-C (1.0 eq) was used instead of Intermediate Compound 1-C (1.0 eq).
[0687] Synthesis of intermediate compound 49-F
[0688] Intermediate Compound 49-F was synthesized in substantially the same manner as that of Intermediate Compound 1-F (yield: 75%), except that Intermediate Compound 49-D (1.0 eq) was used instead of Intermediate Compound 1-D (1.0 eq).
[0689] Synthesis of intermediate compound 49-G
[0690] Intermediate Compound 49-G was synthesized in substantially the same manner as that of Intermediate Compound 1-G (yield: 80%), except that Intermediate Compound 49-F (1.0 eq) was used instead of Intermediate Compound 1-F (1.0 eq).
[0691] Synthesis of compound 49
[0692] Compound 49 (yield: 31%) was synthesized in substantially the same manner as the synthesis of Compound 1, except that Intermediate Compound 49-G (1.0 eq) was used instead of Intermediate Compound 1-G (1.0 eq).
[0693] Synthesis Example 3 (Compound 193)
[0694]
[0695] Synthesis of intermediate compound 193-A
[0696] Intermediate compound 193-A (yield: 66%) was synthesized in essentially the same manner as the synthesis of intermediate compound 1-A, except that (6-fluoro-4-(2-methylpropyl-1,1-d2)pyridin-3-yl)boric acid (1.2 eq) was used instead of (6-fluoro-4-(methyl-d3)pyridin-3-yl)boric acid (1.2 eq).
[0697] Synthesis of intermediate compound 193-B
[0698] Intermediate Compound 193-B was synthesized in substantially the same manner as that of Intermediate Compound 1-B (yield: 82%), except that Intermediate Compound 193-A (1.0 eq) was used instead of Intermediate Compound 1-A (1.0 eq).
[0699] Synthesis of Intermediate Compound 193-C
[0700] Intermediate Compound 193-C was synthesized in substantially the same manner as that of Intermediate Compound 1-C (yield: 84%), except that Intermediate Compound 193-B (1.0 eq) was used instead of Intermediate Compound 1-B (1.0 eq).
[0701] Synthesis of Intermediate Compound 193-D
[0702] Intermediate Compound 193-D was synthesized in substantially the same manner as that of Intermediate Compound 1-D (yield: 69%), except that Intermediate Compound 193-C (1.0 eq) was used instead of Intermediate Compound 1-C (1.0 eq).
[0703] Synthesis of Intermediate Compound 193-F
[0704] Intermediate Compound 193-F was synthesized in substantially the same manner as that of Intermediate Compound 1-F (yield: 75%), except that Intermediate Compound 193-D (1.0 eq) was used instead of Intermediate Compound 1-D (1.0 eq).
[0705] Synthesis of Intermediate Compound 193-G
[0706] Intermediate Compound 193-G was synthesized in substantially the same manner as that of Intermediate Compound 1-G (yield: 83%), except that Intermediate Compound 193-F (1.0 eq) was used instead of Intermediate Compound 1-F (1.0 eq).
[0707] Synthesis of compound 193
[0708] Compound 193 (yield: 37%) was synthesized in substantially the same manner as the synthesis of Compound 1, except that Intermediate Compound 193-G (1.0 eq) was used instead of Intermediate Compound 1-G (1.0 eq).
[0709] Synthesis Example 4 (Compound 241)
[0710]
[0711] Synthesis of intermediate compound 241-A
[0712] Intermediate compound 241-A (yield: 67%) was synthesized in essentially the same manner as the synthesis of intermediate compound 1-A, except that 9-bromo-1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydroanthracene (1.0 eq) was used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (1.0 eq).
[0713] Synthesis of intermediate compound 241-B
[0714] Intermediate Compound 241-B was synthesized in substantially the same manner as that of Intermediate Compound 1-B (yield: 75%), except that Intermediate Compound 241-A (1.0 eq) was used instead of Intermediate Compound 1-A (1.0 eq).
[0715] Synthesis of Intermediate Compound 241-C
[0716] Intermediate Compound 241-C was synthesized in substantially the same manner as that of Intermediate Compound 1-C (yield: 80%), except that Intermediate Compound 241-B (1.0 eq) was used instead of Intermediate Compound 1-B (1.0 eq).
[0717] Synthesis of intermediate compound 241-D
[0718] Intermediate Compound 241-D was synthesized in substantially the same manner as that of Intermediate Compound 1-D (yield: 64%), except that Intermediate Compound 241-C (1.0 eq) was used instead of Intermediate Compound 1-C (1.0 eq).
[0719] Synthesis of intermediate compound 241-F
[0720] Intermediate Compound 241-F was synthesized in substantially the same manner as that of Intermediate Compound 1-F (yield: 74%), except that Intermediate Compound 241-D (1.0 eq) was used instead of Intermediate Compound 1-D (1.0 eq).
[0721] Synthesis of intermediate compound 241-G
[0722] Intermediate Compound 241-G was synthesized in substantially the same manner as that of Intermediate Compound 1-G (yield: 84%), except that Intermediate Compound 241-F (1.0 eq) was used instead of Intermediate Compound 1-F (1.0 eq).
[0723] Synthesis of compound 241
[0724] Compound 241 was synthesized in substantially the same manner as that of Compound 1 (yield: 25%), except that Intermediate Compound 241-G (1.0 eq) was used instead of Intermediate Compound 1-G (1.0 eq).
[0725] For the compounds synthesized in Synthesis Examples 1 to 4, the 1 H NMR and high resolution mass (HR-MS), and the results are shown in Table 1. The synthesis methods of the compounds other than the compounds of Synthesis Examples 1 to 4 can be easily recognized by those skilled in the art by referring to the synthesis routes and starting materials.
[0726] Table 1
[0727]
[0728]
[0729] Evaluation Example 1
[0730] The lowest unoccupied molecular orbital (LUMO) energy level, the highest occupied molecular orbital (HOMO) energy level, the band gap and the maximum emission wavelength (λ) of each of the compounds of Synthesis Examples 1 to 4 were measured by using the method described in Table 2. max ), and the results are shown in Table 3.
[0731] Table 2
[0732]
[0733] Table 3
[0734]
[0735] Example 1
[0736] As an anode, a 15Ω / cm 2 A glass substrate of ITO (product of Corning Incorporated) was cut into a size of 50 mm×50 mm×0.7 mm, cleaned by ultrasonication using isopropyl alcohol and pure water for 5 minutes each, by irradiation of ultraviolet rays and exposure to ozone for 30 minutes, and mounted on a vacuum deposition apparatus.
[0737] 2-TNATA was vacuum deposited on the anode to form a A hole injection layer having a thickness of 1000 Å was formed, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as “NPB”) was vacuum deposited on the hole injection layer to form a The hole transport layer has a thickness of .
[0738] ETH2 as a host, HTH29 as a host, and compound 1 as a dopant were vacuum deposited on the hole transport layer to form a In this regard, the amount of Compound 1 was 10 wt % based on the total weight (100 wt %) of the emission layer, and the weight ratio of ETH2 to HTH29 was adjusted to 3:7.
[0739] The compound ETH2 is vacuum deposited on the emission layer to form a The thickness of the hole blocking layer is Alq 3 Vacuum deposition on the hole blocking layer to form a An electron transport layer having a thickness of , LiF is vacuum deposited on the electron transport layer to form a An electron injection layer having a thickness of , and then, Al is vacuum deposited thereon to form A cathode with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.
[0740]
[0741] Examples 2 to 9 and Comparative Examples 1 to 5
[0742] Organic light-emitting devices of Examples 2 to 9 and Comparative Examples 1 to 5 were respectively manufactured in substantially the same manner as Example 1, except that the compositions of the dopant and the host were adjusted as shown in Table 4.
[0743] In Example 8 and Example 9, Compound 1 (10 wt % based on the total weight of the emission layer) and DFD1 (0.5 wt % based on the total weight of the emission layer) were used as dopants.
[0744]
[0745] Evaluation Example 2
[0746] In order to evaluate the characteristics of each of the organic light-emitting devices manufactured according to Examples 1 to 9 and Comparative Examples 1 to 5, the current at 10 mA / cm 2 The driving voltage and luminous efficiency at the current density of , and the results are shown in Table 4. The driving voltage of each of the organic light-emitting devices was measured by using a source meter (Keithley MU 236), and the luminous efficiency of each of the organic light-emitting devices was measured by using an external quantum efficiency measurement device PR650 of Brother. When evaluating the luminous efficiency, the luminance / current density was measured by using a luminance meter calibrated for wavelength sensitivity, and the luminous efficiency was converted by assuming that an angular luminance distribution (Lambertian) of an ideal diffuse reflector was introduced. In order to measure the device life (LT 90 ), calculate the time required to reach 90% of the initial brightness.
[0747] Table 4
[0748]
[0749]
[0750] According to the embodiment, the use of the organometallic compound represented by Formula 1 may ensure that a light-emitting device having high luminous efficiency and a long device lifespan and high-quality electronic devices including the light-emitting device can be manufactured.
[0751] Embodiments have been disclosed herein, and although terms are employed, they are used and interpreted in a general and descriptive sense only and not for purposes of limitation. In some cases, as will be apparent to one of ordinary skill in the art, features, characteristics, and / or elements described in conjunction with embodiments may be used alone or in combination with features, characteristics, and / or elements described in conjunction with other embodiments unless specifically indicated otherwise. Accordingly, one of ordinary skill in the art will appreciate that various changes in form and detail may be made without departing from the spirit and scope of the present disclosure.
Claims
1. A light emitting device, comprising: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emitting layer; as well as An organometallic compound represented by Formula 1: Formula 1 In formula 1, M is platinum, iridium, palladium, cobalt, gold, nickel, silver or copper, CY1, CY2, CY 31 and CY 32 Each independently is C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, CY5 is a non-aromatic fused polycyclic group or a non-aromatic fused heteropolycyclic group, X1 is C, X2 to X4 are each independently C or N, T1 is a single bond, N(R7), C(R7)(R8), Si(R7)(R8), S or O, L1 to L3 are each independently a single bond, *-N(R9)-*', *-B(R9)-*', *-P(R9)-*', *-C(R9)(R 10 )-*'、*-Si(R9)(R 10 )-*'、*-Ge(R9)(R 10 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*' or *-C(=S)-*', a1, a2, a31, a32 and a5 are each independently an integer selected from 0 to 20, b1 to b3 are each independently an integer selected from 0 to 4, R1, R2, R 31 , R 32 , R 41 To R 43 and R5 to R 10 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2), R 41 To R 43 At least one of each is independently unsubstituted or substituted by at least one R 10a Substituted C1-C 60 alkyl, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: 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 Aralkyl, C2-C 60 Heteroaralkyl, -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; Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl: 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 Aralkyl, C2-C 60 Heteroaralkyl, -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; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; pyridyl; pyrimidinyl; pyridazinyl; pyrazinyl; triazinyl; or each is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C2 substituted by alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl.
2. The light emitting device according to claim 1, wherein The first electrode is an anode, The second electrode is a cathode, The interlayer further comprises: a hole transport region between the first electrode and the emissive layer; as well as an electron transport region between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer or any combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer or any combination thereof. The light-emitting device according to claim 1 , wherein the interlayer comprises the organic metal compound. The light emitting device according to claim 1 , wherein the emission layer comprises the organometallic compound.
5. The light emitting device according to claim 1, wherein The emission layer includes a host, a dopant and a sensitizer, and The sensitizer includes the organometallic compound. 6 . An electronic device comprising the light emitting device according to claim 1 . 7 . The electronic device of claim 6 , further comprising a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof.
8. An electronic device comprising the light emitting device according to any one of claims 1 to 5.
9. The electronic device of claim 8, wherein the electronic device is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a phone, a mobile phone, a tablet computer, a phablet, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a three-dimensional display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, or a sign.
10. An organometallic compound represented by Formula 1: Formula 1 In formula 1, M is platinum, iridium, palladium, cobalt, gold, nickel, silver or copper, CY1, CY2, CY 31 and CY 32 Each independently is C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, CY5 is a non-aromatic fused polycyclic group or a non-aromatic fused heteropolycyclic group, X1 is C, X2 to X4 are each independently C or N, T1 is a single bond, N(R7), C(R7)(R8), Si(R7)(R8), S or O, L1 to L3 are each independently a single bond, *-N(R9)-*', *-B(R9)-*', *-P(R9)-*', *-C(R9)(R 10 )-*'、*-Si(R9)(R 10 )-*'、*-Ge(R9)(R 10 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*' or *-C(=S)-*', a1, a2, a31, a32 and a5 are each independently an integer selected from 0 to 20, b1 to b3 are each independently an integer selected from 0 to 4, R1, R2, R 31 , R 32 , R 41 To R 43 and R5 to R 10 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or replaced by at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2), R 41 To R 43 At least one of each is independently unsubstituted or substituted by at least one R 10a Substituted C1-C 60 alkyl, R 10a for: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Each unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy: 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 Aralkyl, C2-C 60 Heteroaralkyl, -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; Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl: 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 Aralkyl, C2-C 60 Heteroaralkyl, -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; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; pyridyl; pyrimidinyl; pyridazinyl; pyrazinyl; triazinyl; or each is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C2 substituted by alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl.
11. The organometallic compound of claim 10, wherein the organometallic compound comprises at least one deuterium.
12. The organometallic compound according to claim 10, wherein M is platinum.
13. The organometallic compound according to claim 10, wherein CY5 is: With at least one C3-C 10 At least one C6-C 60 Aryl; or With at least one C1-C 10 Heterocycloalkyl fused with at least one C6-C 60 Aryl.
14. The organometallic compound according to claim 10, wherein The bond between X1 and M and the bond between X4 and M are each coordinate bonds, and The bond between X2 and M and the bond between X3 and M are each covalent bonds.
15. The organometallic compound according to claim 10, wherein R 41 and R 43 are each independently hydrogen or deuterium, and R 42 is unsubstituted or substituted with at least one R 10a Substituted C1-C 60 alkyl.
16. The organometallic compound according to claim 10, wherein CY5 is a group represented by one of Formula 2-1 to Formula 2-4: In Formula 2-1 to Formula 2-4, R 51 and R 52 Each is independently the same as defined in R5 in Reference Formula 1, a51 is an integer selected from 0 to 11, a52 is an integer selected from 0 to 17, and *Indicates the bonding site to the adjacent carbon atom.
17. The organometallic compound according to claim 10, wherein R1, R2, R 31 , R 32 , R 41 To R 43 and R5 to R 10 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I or cyano; methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl or 1,2-dimethylpropyl, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; or Phenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, azadibenzofuranyl, azadibenzothienyl or azacarbazolyl, each unsubstituted or substituted by: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl or phenyl, each unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro.
18. The organometallic compound according to claim 10, wherein R6 is phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, heptalenyl, tetracenyl, pyrenyl, hexenyl, pentacene, rubenyl, coronenyl, ovalenyl, biphenyl or terphenyl, each of which is unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C6-C 60 aryl or any combination thereof.
19. The organometallic compound according to claim 10, wherein R6 is a group represented by one of Formula 3-1 to Formula 3-3: In Formula 3-1 to Formula 3-3, R 61 To R 64 Each is independently the same as defined in R6 in Reference Formula 1, a61 is an integer selected from 1 to 5, a62 is an integer selected from 1 to 3, a63 is an integer selected from 1 to 5, a64 is an integer selected from 1 to 4, and *Indicates the bonding site to the adjacent nitrogen atom.
20. The organometallic compound according to claim 10, wherein the organometallic compound represented by Formula 1 is one of Compound 1 to Compound 288:
Citation Information
Patent Citations
Organic compound and electroluminescent device comprising the same
KR1020230146997A