Organometal compound, organic light-emitting device including the same, and electronic device and electronic device
By developing new organometallic compounds and applying them to organic light emitting devices, the problems of high driving voltage and low luminous efficiency in the prior art are solved, and an organic light emitting device with low driving voltage and high luminous efficiency are realized, which improves the performance and life of the equipment.
Patent Information
- Application Number
- CN202411509223.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-10-27
- Filing Date
- 2024-10-28
- Publication Date
- 2025-04-29
AI Technical Summary
The existing organic light emitting devices have shortcomings in driving voltage and luminous efficiency, and it is difficult to meet the needs of high efficiency and low consumption.
A new organometallic compound has been developed, and through its application in organic light emitting devices, an organic light emitting device with low driving voltage and high luminous efficiency has been achieved. The compound consists of organometallic compounds of specific structures and is used to replace traditional emission layer materials.
The low driving voltage and high luminous efficiency of the organic light emitting device are achieved, which improves the performance and life of the equipment, while reducing energy consumption.
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Figure CN119899213A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0145425 filed in the Korean Intellectual Property Office on October 27, 2023, the entire contents of which are incorporated herein by reference. Technical Field
[0003] Embodiments relate to an organometallic compound, an organic light-emitting device including the same, and electronic equipment and electronic devices including the organic light-emitting device. Background Art
[0004] Among light-emitting devices, an organic light-emitting device is a self-emitting device having wide viewing angles, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to devices in the related art.
[0005] In an example, an organic light-emitting device may have a structure in which a first electrode is arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to generate excitons. Excitons may transition from an excited state to a ground state, thereby generating light.
[0006] It should be understood that this background section is intended, in part, to provide a useful background for understanding the technology. However, this background section may also include ideas, concepts, or cognitions that were not part of the knowledge or understanding of 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 provide a novel organometallic compound and an organic light-emitting device having low driving voltage and high light-emitting efficiency by including the novel organometallic compound. Embodiments include electronic devices and electronic equipment including the organic 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 organometallic compound may be represented by Formula 1:
[0010] [Formula 1]
[0011]
[0012] [Formula 3A]
[0013]
[0014] In Formula 1 and Formula 3A,
[0015] M may be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm),
[0016] A 1 , A 2 and A 4 Can be independently C 5 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0017] Y 1 , Y 2 and Y 4 can be independently C or N,
[0018] T 1 To T 4 Can indicate chemical bonds individually,
[0019] L 1 To L 4 can be independently a single bond, *-O-*', *-S-*', *-C(R 5 )(R 6 )-*'、*-C(R 5 )=*'、*=C(R 5 )-*'、*-C(R 5 )=C(R 6 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 5 )-*'、*-N(R 5 )-*'、*-P(R 5 )-*'、*-Si(R 5 )(R 6 )-*'or*-Ge(R 5 )(R 6 )-*',
[0020] a1 to a4 may each independently be an integer selected from 0 to 5,
[0021] R 31 To R 36Each of them may be independently a group represented by Formula 3A, 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 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, 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 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ),
[0022] R 31 To R 36 At least one of them may be independently a group represented by Formula 3A,
[0023] R 1 , R 2 , R 4 , R 5 and R 6 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 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, 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 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ),
[0024] n1, n2 and n4 may each independently be an integer selected from 0 to 10,
[0025] R 1 , R 2 , R 4 , R 5 and R 6 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 60The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0026] Z 31 To Z 37 Can be independently:
[0027] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0028] 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, -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;
[0029] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy or C 6 -C 60 Arylthio: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C2 -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, -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
[0030] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),
[0031] R 10a Can be:
[0032] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0033] 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 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, 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;
[0034] 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 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, 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 60Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, 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
[0035] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),
[0036] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl, and
[0037] *Indicates the binding site with the neighboring atoms.
[0038] In an embodiment, R 31 To R 36 Two or more of may each independently be a group represented by Formula 3A.
[0039] In an embodiment, R 33 may be a group represented by Formula 3A; and R 31 , R 32 , R 34 , R 35 and R 36 One of the groups may be a group represented by Formula 3A.
[0040] In an embodiment, Z 31 To Z 37 may be independently: hydrogen or deuterium; or unsubstituted or deuterated C 1 -C 20 alkyl.
[0041] In an embodiment, M may be Pt, Pd, Cu, Ag, or Au.
[0042] In an embodiment, T 1 To T 4 Two of them may each be a coordination bond; and T 1 To T 4 The rest of them may each be a covalent bond.
[0043] In an embodiment, L 1 To L 4 can be independently a single bond, *-O-*', *-S-*', *-N(R 5 )-*'、*-C(R 5 )(R 6 )-*'、*-Si(R 5 )(R 6 )-*' or *-B(R 5 )-*';R 5 and R 6and * and *' each indicate a binding site with an adjacent atom.
[0044] In an embodiment, a4 may be 0.
[0045] In an embodiment, a4 may be 0; and The moiety represented by may be a moiety represented by Formula 1A or Formula 1B, which are explained below:
[0046]
[0047] Wherein in Formula 1A and Formula 1B,
[0048] Y 12 C(R 12 ) or N,
[0049] Y 13 C(R 13 ) or N,
[0050] Y 14 C(R 14 ) or N,
[0051] Y 15 C(R 15 ) or N,
[0052] Y 16 C(R 16 ) or N,
[0053] Y 17 C(R 17 ) or N,
[0054] R 11 To R 17 Each independently corresponds to R in Formula 1 1 are defined the same as
[0055] * and *' each indicate a binding site with an adjacent atom.
[0056] In an embodiment, R 11 It may be a group represented by one of Formula 10A to Formula 19A, which are explained below.
[0057] In an embodiment, the organometallic compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2, which is explained below.
[0058] In an embodiment, the organometallic compound represented by Formula 1 may be one of Compound 1 to Compound 90, which are explained below.
[0059] According to an embodiment, an organic light-emitting device 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, which is explained herein.
[0060] In an embodiment, the emission layer may include the organic metal compound represented by Formula 1.
[0061] In an embodiment, the emission layer may include a host and a dopant; and the dopant may include an organic metal compound represented by Formula 1.
[0062] In an embodiment, the emission layer may emit blue light having a maximum emission wavelength in the range of about 410 nm to about 490 nm.
[0063] In an embodiment, the emission layer may further include a delayed fluorescent material.
[0064] According to an embodiment, an electronic device may include an organic light emitting device.
[0065] In an embodiment, the electronic device may further include a thin film transistor, wherein
[0066] The thin film transistor may include a source electrode and a drain electrode; and the first electrode of the organic light emitting device may be electrically connected to at least one of the source electrode and the drain electrode.
[0067] According to an embodiment, an electronic device may include an organic light emitting device, wherein
[0068] The electronic device can 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 retractable display, a laser printer, a phone, a mobile phone, a tablet personal computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater screen, a stadium screen, a light therapy device, a sign, a car sensor, a home sensor, or a solar cell.
[0069] It should be understood that the above embodiments have been described in a general and explanatory sense only and not for purposes of limitation, and the present disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS
[0070] 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 the embodiments of the present disclosure in detail with reference to the attached drawings, in which:
[0071] Figure 1 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment;
[0072] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment;
[0073] Figure 3 is a schematic cross-sectional view of an electronic device according to an embodiment;
[0074] Figure 4 is a schematic perspective view of an electronic device including an organic light-emitting device according to an embodiment;
[0075] Figure 5 is a schematic perspective view of the exterior of a vehicle as an example of an electronic device including an organic light-emitting device according to an embodiment; and
[0076] FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle according to an embodiment. DETAILED DESCRIPTION
[0077] 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 being 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.
[0078] 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 the same reference characters refer to the same elements throughout.
[0079] In the specification, it will be understood that when an element (or region, layer, portion, etc.) is referred to as being “on”, “connected to” or “coupled to” another element (or region, layer, portion, etc.), it may be directly on, connected to or coupled to the other element (or region, layer, portion, etc.), or one or more intervening elements (or regions, layers, portions, etc.) may be present therebetween. In a similar sense, when an element (or region, layer, portion, etc.) is described as “covering” another element (or region, layer, portion, etc.), it may directly cover the other element (or region, layer, portion, etc.), or one or more intervening elements (or regions, layers, portions, etc.) may be present therebetween.
[0080] In the specification, 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 another element (such as an adhesive element) between them.
[0081] In the specification, 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.
[0082] In the specification, the term "and / or" includes any and all combinations of one or more related listed items. For example, "A and / or B" can be understood to mean "A, B, or A and B". The terms "and" and "or" can be used in a connecting sense or a separating sense and can be understood to be equivalent to "and / or".
[0083] 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.
[0084] 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.
[0085] For ease of description, spatially relative terms such as "below," "under," "below," "above," or "over" 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 "over" the other device. Accordingly, the illustrative term "below" may include both a below position and an above position. The device may also be oriented in other directions, and thus the spatially relative terms may be interpreted differently depending on the orientation.
[0086] As used herein, the terms "about" or "approximately" include the stated value and mean within an acceptable range of deviation from the stated value as determined by one of ordinary skill in the art taking into account the measurement in question and errors associated with the measurement of the stated quantity (i.e., 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.
[0087] 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 specified 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.
[0088] 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.
[0089] Embodiments provide an organic 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.
[0090] In an embodiment, the first electrode may be an anode. In an embodiment, the second electrode may be a cathode.
[0091] The term “interlayer” as used herein refers to a single layer and / or a plurality of layers disposed between a first electrode and a second electrode of an organic light-emitting device.
[0092] In an embodiment, 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 at least one of a hole injection layer, a hole transport layer, and an electron blocking layer. The electron transport region may include at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.
[0093] In an embodiment, the interlayer may include an organic metal compound represented by Formula 1.
[0094] In an embodiment, the emission layer may include the organic metal compound represented by Formula 1.
[0095] In an embodiment, the emission layer may include a host and a dopant, and the dopant may include an organic metal compound represented by Formula 1.
[0096] In an embodiment, the emission layer may emit blue light. The emission layer may emit blue light having a maximum emission wavelength in the range of about 390nm to about 500nm. For example, the emission layer may emit blue light having a maximum emission wavelength in the range of about 410nm to about 500nm. As another example, the emission layer may emit blue light having a maximum emission wavelength in the range of about 390nm to about 490nm. For example, the emission layer may emit blue light having a maximum emission wavelength in the range of about 410nm to about 490nm. As yet another example, the emission layer may emit blue light having a maximum emission wavelength in the range of about 430nm to about 480nm.
[0097] In an embodiment, the emission layer may further include a delayed fluorescent material.
[0098] Another embodiment provides an electronic device, which may include an organic light emitting device.
[0099] In an embodiment, the electronic device may further include a thin film transistor, wherein the thin film transistor may include a source electrode and a drain electrode, and the first electrode of the organic light emitting device may be electrically connected to at least one of the source electrode and the drain electrode of the thin film transistor.
[0100] Another embodiment provides an electronic device that may include an organic light emitting device, wherein 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 retractable display, a laser printer, a phone, a mobile phone, a tablet personal computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater screen, a stadium screen, a light therapy device, a sign, a car sensor, a home sensor, or a solar cell.
[0101] Another embodiment provides an organometallic compound, which can be represented by Formula 1:
[0102] [Formula 1]
[0103]
[0104] [Formula 3A]
[0105]
[0106] Formula 1 and Formula 3A may be the same as described herein.
[0107] In Formula 1, M may be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm).
[0108] In an embodiment, M may be Pt, Pd, Cu, Ag, or Au.
[0109] In formula 1,
[0110] A 1 , A 2 and A 4 Can be independently C 5 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0111] Y 1 , Y 2 and Y 4 can be independently C or N,
[0112] T 1 To T4 Can indicate chemical bonds individually,
[0113] L 1 To L 4 can be independently a single bond, *-O-*', *-S-*', *-C(R 5 )(R 6 )-*'、*-C(R 5 )=*'、*=C(R 5 )-*'、*-C(R 5 )=C(R 6 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 5 )-*'、*-N(R 5 )-*'、*-P(R 5 )-*'、*-Si(R 5 )(R 6 )-*'or*-Ge(R 5 )(R 6 )-*',and
[0114] a1 to a4 may be an integer selected from 0 to 5, each independently.
[0115] Examples of chemical bonds may include covalent bonds, coordinate bonds, and the like.
[0116] In an embodiment, T 1 To T 4 The two of them can each be a coordination bond, and T 1 To T 4 The rest of them may each be a covalent bond.
[0117] In an embodiment, L 1 To L 4 can be independently a single bond, *-O-*', *-S-*', *-N(R 5 )-*'、*-C(R 5 )(R 6 )-*'、*-Si(R 5 )(R 6 )-*' or *-B(R 5 )-*', where R 5 and R 6 and *' each indicate a binding site with an adjacent atom.
[0118] In an embodiment, a4 may be 0.
[0119] In an embodiment, a1, a2, and a3 may each be 1.
[0120] In an embodiment, in Formula 1, a4 may be 0, and The part represented can be
[0121] The moiety represented by Formula 1A or Formula 1B:
[0122]
[0123] In Formula 1A and Formula 1B,
[0124] Y 12 Can be C(R 12 ) or N, and Y 13 Can be C(R 13 ) or N,
[0125] Y 14 Can be C(R 14 ) or N, Y 15 Can be C(R 15 ) or N, Y 16 Can be C(R 16 ) or N, and Y 17 Can be C(R 17 ) or N,
[0126] R 11 To R 17 Can be independently compared with reference R 1 Same as described, and
[0127] * and *' each indicate a binding site with an adjacent atom.
[0128] In an embodiment, in Formula 1A and Formula 1B, R 11 It may be a group represented by one of Formula 10A to Formula 19A:
[0129]
[0130] In Formula 10A to Formula 19A,
[0131] Z 11 To Z 13 Can be independently compared with reference R 10a Same as described,
[0132] d3 may be an integer selected from 0 to 3,
[0133] d4 may be an integer selected from 0 to 4,
[0134] d5 may be an integer selected from 0 to 5, and
[0135] *Indicates the binding site with the neighboring atoms.
[0136] In an embodiment, Z11 To Z 13 Can be independently:
[0137] Deuterium, -F, -Cl, -Br or -I;
[0138] Each unsubstituted or substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl or C 2 -C 60 Alkynyl: deuterium, -F, -Cl, -Br, -I, C 3 -C 60 Carbocyclic group or any combination thereof;
[0139] Unsubstituted or substituted by C 3 -C 60 Carbocyclic group: deuterium, -F, -Cl, -Br, -I, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 3 -C 60 Carbocyclic group or any combination thereof; or
[0140] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ), where Q 31 To Q 33 Each may be the same as described herein.
[0141] In an embodiment, each Z 11 It may not be a carbazole group.
[0142] In an embodiment, in Formula 1, The moiety represented by may be a moiety represented by Formula 2A:
[0143]
[0144] In Formula 2A,
[0145] Y 21 Can be C(R 21 ) or N, Y 22 Can be C(R 22 ) or N, and Y 23 Can be C(R 23 ) or N,
[0146] R 21 To R 23 Can be independently combined with R in this article 2 Same as described, and
[0147] *, *' and *" each indicate a binding site with an adjacent atom.
[0148] In an embodiment, in Formula 1, a4 may be 0, and The moiety represented by may be a moiety represented by Formula 4A:
[0149]
[0150] In Formula 4A,
[0151] Y 41 Can be C(R 41 ) or N, Y 42 Can be C(R 42 ) or N, Y 43 Can be C(R 43 ) or N, and Y 44 Can be C(R 44 ) or N,
[0152] R 41 To R 44 Can be independently combined with R in this article 4 Same as described, and
[0153] * and *' each indicate a binding site with an adjacent atom.
[0154] In formula 1, R 31 To R 36 Each of them may be independently a group represented by Formula 3A, 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 60Alkynyl, 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 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, 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 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ),and
[0155] R 31 To R 36 At least one of them may each independently be a group represented by Formula 3A.
[0156] In an embodiment, R 31 To R 36 At least two of them may each independently be a group represented by Formula 3A.
[0157] In an embodiment, R 33 may be a group represented by Formula 3A, and R 31 , R 32 , R 34 , R 35 and R 36 One of the groups may be a group represented by Formula 3A.
[0158] In an embodiment, R 31 To R 36 Each of them may not be connected with R 31 To R 36 Adjacent groups in the group combine to form a ring.
[0159] In formula 1, R 1 , R 2 , R 4 , R 5 and R 6 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 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, 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 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ),
[0160] n1, n2 and n4 may each independently be an integer selected from 0 to 10, and
[0161] R 1 , R 2 , R4 , R 5 and R 6 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 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group.
[0162] In formula 1, Z 31 To Z 37 Can be independently:
[0163] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0164] 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, -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;
[0165] Each unsubstituted or substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy or C6 -C 60 Arylthio: 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, -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
[0166] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ).
[0167] In an embodiment, Z 31 To Z 37 Can be independently:
[0168] hydrogen, deuterium, -F, -Cl, -Br or -I; or
[0169] Each unsubstituted or substituted C 1 -C 20 Alkyl, C 2 -C20 Alkenyl or C 2 -C 20 Alkynyl: deuterium, -F, -Cl, -Br, -I or any combination thereof.
[0170] In an embodiment, Z 31 To Z 37 may be independently: hydrogen; deuterium; or unsubstituted or deuterium-substituted C 1 -C 20 alkyl.
[0171] In formula 1, R 10a Can be:
[0172] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0173] 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 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, 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;
[0174] 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 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, 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 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, 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
[0175] -Si(Q 31 )(Q 32 )(Q33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),
[0176] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each 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 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 heteroarylalkyl, and
[0177] *Indicates the binding site with the neighboring atoms.
[0178] In an embodiment, the organometallic compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2:
[0179] [Formula 1-1]
[0180]
[0181] [Formula 1-2]
[0182]
[0183] In Formula 1-1 or Formula 1-2,
[0184] M.T 1 To T 4 , L 2 and R 31 To R 36 may each be the same as described herein,
[0185] Y 12 Can be C(R 12 ) or N, Y 13 Can be C(R 13 ) or N, Y 14 Can be C(R 14 ) or N, Y 15 Can be C(R 15 ) or N, Y 16 Can be C(R 16 ) or N, and Y 17 Can be C(R 17 ) or N,
[0186] Y 21 Can be C(R 21 ) or N, Y 22 Can be C(R 22 ) or N, and Y 23 Can be C(R 23 ) or N,
[0187] Y 41 Can be C(R 41 ) or N, Y 42 Can be C(R 42 ) or N, Y 43 Can be C(R 43 ) or N, and Y 44 Can be C(R 44 )
[0188] or N,
[0189] R 11 To R 17 Can be independently compared with reference R 1 Same as described,
[0190] R 21 To R 23 Can be independently combined with R in this article 2 Same as described, and
[0191] R 41 To R 44 Can be independently combined with R in this article 4 Same as described.
[0192] In an embodiment, the organometallic compound represented by Formula 1 may be electrically neutral.
[0193] In an embodiment, the HOMO energy level (eV) of the organometallic compound represented by Formula 1 may be -4.90 eV to -4.80 eV, and the LUMO energy level (eV) of the organometallic compound represented by Formula 1 may be -1.50 eV to -1.40 eV. In an embodiment, the maximum emission wavelength (λ max ) may be 390 nm to 500 nm, for example, 410 nm to 490 nm or 450 nm to 460 nm. In an embodiment, the triplet metal to ligand charge transfer state ( 3 The presence ratio (%) of MLCT) may be 10% to 13%, for example, 10.45% to 12.50% or 10.50% to 12.30%.
[0194] In an embodiment, the organometallic compound represented by Formula 1 may be one of Compound 1 to Compound 90:
[0195]
[0196]
[0197]
[0198]
[0199]
[0200]
[0201] The organometallic compound represented by Formula 1 has a structure in which a long alkyl chain is introduced into a carbazole group, and thus may have a reduced sublimation temperature and improved heat resistance stability. The intensity of the secondary emission may be reduced by the long alkyl chain, so that the color purity may be improved, which may contribute to increasing the luminous efficiency and improving the lifespan. In the emission spectrum of the organometallic compound, it is ideal that only the first peak exists, but in the case of some compounds, the second peak exists. When the second peak exists, the FWHM increases, and the color purity decreases. The intensity of the secondary emission means the emission of the second peak.
[0202] Therefore, the organic light-emitting device including the organometallic compound represented by Formula 1 can have low driving voltage and high luminous efficiency. For example, in the case of including the organometallic compound represented by Formula 1 as a dopant in the emission layer, the organic light-emitting device including the organometallic compound represented by Formula 1 can exhibit low driving voltage, high luminous efficiency, high color conversion efficiency and long life.
[0203] The synthesis method of the organometallic compound represented by Formula 1 can be recognized by one of ordinary skill in the art by referring to the examples provided below.
[0204] [ Figure 1 Description]
[0205] Figure 1 2 is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110 , an interlayer 130 , and a second electrode 150 .
[0206] In the following, we will combine Figure 1 A structure of an organic light-emitting device 10 and a method of manufacturing the organic light-emitting device 10 according to an embodiment are described.
[0207] [First electrode 110]
[0208] 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.
[0209] The first electrode 110 may be formed, for example, by depositing or sputtering a material for forming the first electrode 110 on a substrate. In the case where 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.
[0210] 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.
[0211] 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.
[0212] [Interlayer 130]
[0213] The interlayer 130 is disposed on the first electrode 110. The interlayer 130 may include an emission layer.
[0214] 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 .
[0215] The interlayer 130 may further include a metal-containing compound such as an organic metal compound represented by Formula 1 or an inorganic material such as a quantum dot, etc., in addition to various organic materials.
[0216] 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 between adjacent units of the two or more emission units. In the case where the interlayer 130 includes two or more emission units and at least one charge generation layer, the organic light-emitting device 10 may be a tandem organic light-emitting device.
[0217] [Hole Transport Region in Interlayer 130]
[0218] The hole transport region may have a structure composed of a layer (composed of a single material), a structure composed of a layer including different materials, or a structure including a plurality of layers (including different materials).
[0219] 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.
[0220] In an embodiment, the hole transport region may have a multi-layer 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 in their respective described order from the first electrode 110, but the structure of the hole transport region is not limited thereto.
[0221] In an embodiment, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0222] [Formula 201]
[0223]
[0224] [Formula 202]
[0225]
[0226] In equation 201 and equation 202,
[0227] 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,
[0228] L 205 Can 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,
[0229] xa1 to xa4 may each independently be an integer selected from 0 to 5,
[0230] xa5 may be an integer selected from 1 to 10,
[0231] 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,
[0232] 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 5The 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.),
[0233] 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 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, and
[0234] na1 may be an integer selected from 1 to 4.
[0235] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of the groups represented by Formulas CY201 to CY217:
[0236]
[0237] In formula CY201 to formula CY217, R 10b and R 10c Can be independently compared with reference R 10a Same as described, CY 201 To Ring CY 204 Can be independently C 3 -C 20 Carbocyclic or C 1 -C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R 10a replace.
[0238] 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.
[0239] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of the groups represented by Formulas CY201 to CY203.
[0240] 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.
[0241] 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.
[0242] 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.
[0243] 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.
[0244] 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.
[0245] 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:
[0246]
[0247]
[0248]
[0249]
[0250]
[0251] 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 In the case where 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 thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0252] The emission assisting layer can increase light emission 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 electrons from the emission layer from leaking to the hole transporting region. Materials that can be included in the hole transporting region can be included in the emission assisting layer and the electron blocking layer.
[0253] [p-dopant]
[0254] In addition to the aforementioned materials, the hole transport region may further include a charge generation material for improvement of conductive properties. 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).
[0255] The charge generating material may be, for example, a p-dopant.
[0256] In an embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level equal to or less than about −3.5 eV.
[0257] 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.
[0258] Examples of the quinone derivative may include TCNQ, F4-TCNQ, and the like.
[0259] Examples of the cyano group-containing compound may include HAT-CN and a compound represented by Formula 221, and the like:
[0260]
[0261] [Formula 221]
[0262]
[0263] In formula 221,
[0264] 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
[0265] 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.
[0266] 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.
[0267] 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.
[0268] Examples of metalloids may include silicon (Si), antimony (Sb), tellurium (Te), and the like.
[0269] Examples of non-metal may include oxygen (O) and halogen (eg, F, Cl, Br, I, etc.), and the like.
[0270] Examples of compounds containing 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.
[0271] 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.
[0272] 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.
[0273] 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.
[0274] 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 、BaCl2 ,BeBr 2 MgBr 2 , CaBr 2 , SrBr 2 ,BaBr 2 ,BeI 2 MgI 2 ,CaI 2 , SrI 2 and BaI 2 wait.
[0275] Examples of transition metal halides may include titanium halides (eg, TiF 4 、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.
[0276] 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.
[0277] Examples of lanthanide metal halides may include YbF, YbF 2 , YbF 3 、SmF 3 , YbCl, YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3 and SmI 3 wait.
[0278] Examples of metalloid halides may include antimony halides (eg, SbCl 5 etc.
[0279] 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 2Te, 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.
[0280] [Emitting layer in interlayer 130]
[0281] In the case where the organic light-emitting device 10 is a full-color organic 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 sub-pixels. 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.
[0282] 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.
[0283] 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.
[0284] In an embodiment, the emissive layer may include quantum dots.
[0285] 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.
[0286] In addition to the aforementioned organic metal compound represented by Formula 1, the emission layer may further include a host, an auxiliary dopant, a sensitizer, a delayed fluorescent material, or any combination thereof. Each of the host, the auxiliary dopant, the sensitizer, the delayed fluorescent material, or any combination thereof may include at least one deuterium atom.
[0287] In an embodiment, the emission layer may include an organic metal compound represented by Formula 1 and a host. The host may be different from the organic metal compound represented by Formula 1, and the host may include an electron transport compound (electron transport host), a hole transport compound (hole transport host), a bipolar compound (electron transport host), or any combination thereof. The host may not include a metal. The electron transport compound, the hole transport compound, and the bipolar compound may be different from each other.
[0288] In an embodiment, the emission layer may include the organometallic compound represented by Formula 1 and a host, and the host may include an electron transport compound and a hole transport compound.
[0289] In embodiments, the electron transport compound and the hole transport compound may form an exciplex.
[0290] 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 these ranges, excellent light emitting characteristics can be obtained without significantly increasing the driving voltage.
[0291] [main body]
[0292] In an embodiment, the host may include a compound represented by Formula 301:
[0293] [Formula 301]
[0294] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0295] In formula 301,
[0296] 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 10a Substituted C 1 -C 60 Heterocyclic group,
[0297] xb11 can be 1, 2 or 3,
[0298] xb1 may be an integer selected from 0 to 5,
[0299] 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 10aSubstituted 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 ),
[0300] xb21 may be an integer selected from 1 to 5, and
[0301] Q 301 To Q 303 Can be independently compared with reference Q 1 Same as described.
[0302] 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.
[0303] 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:
[0304] [Formula 301-1]
[0305]
[0306] [Formula 301-2]
[0307]
[0308] In Formula 301-1 and Formula 301-2,
[0309] Ring A 301 To Ring A 304 may be each independently unsubstituted or substituted with at least one R 10a Substituted C3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group,
[0310] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0311] xb22 and xb23 can each independently be 0, 1 or 2,
[0312] L 301 , xb1 and R 301 may each be the same as described herein,
[0313] L 302 To L 304 Can be independently compared with reference L 301 Same as described,
[0314] xb2 to xb4 may each independently be the same as described with reference to xb1, and
[0315] R 302 To R 305 and R 311 To R 314 Can be independently compared with reference R 301 Same as described.
[0316] In embodiments, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In embodiments, the host may include a Be complex (eg, compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0317] In an embodiment, the host may include one of Compounds H1 to H124, 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:
[0318]
[0319]
[0320]
[0321]
[0322]
[0323]
[0324] In an embodiment, the host may include a first host compound and a second host compound.
[0325] In embodiments, the first host compound may be a hole transporting host.
[0326] In embodiments, the second host compound may be an electron transporting host.
[0327] In an embodiment, the term “hole transport host” as used herein may be a compound including a hole transport moiety.
[0328] In an embodiment, the term “electron transport host” as used herein may be a compound not only including an electron transport moiety but also having a bipolar property.
[0329] The terms "hole transport host" and "electron transport host" as used herein can be understood according to the relative difference between hole mobility and electron mobility. For example, even when the electron transport host does not include an electron transport moiety, a bipolar compound that exhibits a relatively higher electron mobility than the hole transport host can also be understood as an electron transport host.
[0330] In an embodiment, the hole transport host may be represented by one of Formulas 311-1 to 311-6, and the electron transport host may be represented by one of Formulas 312-1 to 312-4 and 313:
[0331] [Formula 311-1]
[0332]
[0333] [Formula 311-2]
[0334]
[0335] [Formula 311-3]
[0336]
[0337] [Formula 311-4]
[0338]
[0339] [Formula 311-5]
[0340]
[0341] [Formula 311-6]
[0342]
[0343] [Formula 312-1]
[0344]
[0345] [Formula 312-2]
[0346]
[0347] [Formula 312-3]
[0348]
[0349] [Formula 312-4]
[0350]
[0351] [Formula 313]
[0352]
[0353] [Formula 313A]
[0354]
[0355] In Formulas 311-1 to 311-6, Formulas 312-1 to 312-4, Formula 313, and Formula 313A,
[0356] Ar 301 may be 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,
[0357] A 301 To A 304 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0358] X 301 Can be O, S, N[(L 304 )xb4 -R 304 ],C[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ] or Si[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ],
[0359] X 302 , Y 301 and Y 302 can be independently a single bond, O, S, N[(L 305 ) xb5 -R 305 ]、C[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ]、Si[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ] or S(=O) 2 ,
[0360] xb1 to xb5 can each be 0, 1, 2, 3, 4 or 5,
[0361] xb6 can be 1, 2, 3, 4 or 5,
[0362] X 321 To X 328 can be independently N or C[(L 324 ) xb24 -R 324 ],
[0363] Y 321 Can be *-O-*', *-S-*', *-N[(L 325 ) xb25 -R 325 ]-*'、*-C[(L 325 ) xb25 -R 325 ][(L 326 ) xb26 -R 326 ]-*'、*-C[(L 325 ) xb25-R 325 ]=C[(L 326 ) xb26 -R 326 ]-*'、*-C[(L 325 ) xb25 -R 325 ]=N-*'or*-N=C[(L 326 ) xb26 -R 326 ]-*',
[0364] k21 can be 0, 1 or 2, where when k21 is 0, Y 321 does not exist,
[0365] xb21 to xb26 may each independently be 0, 1, 2, 3, 4 or 5,
[0366] A 31 , A 32 and A 34 Can be independently C 3 -C 60 Carbocyclic or C 1 -C 30 Heterocyclic group,
[0367] A 33 may be a group represented by formula 313A,
[0368] X 31 Can be N[(L 335 ) xb35 -(R 335 )]、O、S、Se、C[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )] or Si[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )],
[0369] xb31 to xb36 may each independently be 0, 1, 2, 3, 4 or 5,
[0370] xb42 to xb44 may each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,
[0371] L 301 To L 306 , L 321 To L 326 and L331 To L 336 may be independently a single bond, unsubstituted or substituted 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 2 -C 20 Alkyne, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkylene, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenylene, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylene, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylene, unsubstituted or substituted with at least one R 10a The substituted divalent non-aromatic fused polycyclic group is either unsubstituted or substituted with at least one R 10a a substituted divalent non-aromatic fused heteropolycyclic group,
[0372] R 301 To R 305 , R 311 To R 314 , R 321 To R 326 and R 331 To R 336 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 C2 -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 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryl, 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 1 -C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a Substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ),
[0373] 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 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, R 10a Can be:
[0374] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0375] 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 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, 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;
[0376] 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 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, 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 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, 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
[0377] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and
[0378] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each 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 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.
[0379] In an embodiment, the first host compound and the second host compound may form an exciplex. For example, the hole transport host may include HTH29, and the electron transport host may include ETH2:
[0380]
[0381] [Phosphorescent dopant]
[0382] In an embodiment, the emission layer may further include a phosphorescent dopant.
[0383] For example, the emission layer may further include a phosphorescent dopant, and the phosphorescent dopant may serve as a sensitizer.
[0384] The phosphorescent dopant may include at least one transition metal as a central metal.
[0385] 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.
[0386] The phosphorescent dopant may be electrically neutral.
[0387] In an embodiment, the phosphorescent dopant may be an organometallic compound.
[0388] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0389] [Formula 401]
[0390] M(L 401 ) xc1 (L 402 ) xc2
[0391] [Formula 402]
[0392]
[0393] In equations 401 and 402,
[0394] M may be a transition metal (e.g., Ir, Pt, Pd, Os, Ti, Au, Hf, Eu, Tb, Rh, Re, or Tm),
[0395] 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,
[0396] 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,
[0397] X 401 and X 402 may each independently be nitrogen or carbon,
[0398] Ring A 401 and Ring A 402 Can be independently C 3-C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0399] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*',
[0400] *-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C=*',
[0401] 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 )(Q 414 ),
[0402] Q 411 To Q 414 Can be independently compared with reference Q 1 Same as described,
[0403] R 401 and R 402 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with 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 ),
[0404] Q 401 To Q 403 Can be independently compared with reference Q 1 Same as described,
[0405] xc11 and xc12 may each independently be an integer selected from 0 to 10, and
[0406] * and *' in Formula 402 each indicate a binding site with M in Formula 401.
[0407] 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.
[0408] 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, and 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.
[0409] 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., acetylacetonate group), a carboxylic acid group (e.g., picolinate group), -C(=O), an isonitrile group, a -CN group, a phosphorus-containing group (e.g., phosphine group, phosphite group, etc.), or any combination thereof.
[0410] The phosphorescent dopant may be, for example, one of Compound PD1 to Compound PD41 or any combination thereof:
[0411]
[0412]
[0413]
[0414] [Fluorescent dopant]
[0415] In an embodiment, the emission layer may further include a fluorescent dopant.
[0416] The fluorescent dopant may include an amine-containing compound, a styrene-containing compound, or any combination thereof.
[0417] In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:
[0418] [Formula 501]
[0419]
[0420] In formula 501,
[0421] 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 R 10a Substituted C 1 -C 60 Heterocyclic group,
[0422] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0423] xd4 can be 1, 2, 3, 4, 5 or 6.
[0424] In an embodiment, in Formula 501, Ar 501 It may be a condensed ring group in which three or more monocyclic groups are condensed together (for example, anthracenyl, 1,2-triphenylenyl, pyrenyl, etc.).
[0425] In an embodiment, in formula 501, xd4 may be 2.
[0426] In an embodiment, the fluorescent dopant may include: one of compounds FD1 to FD36; DPVBi; DPAVBi; or any combination thereof:
[0427]
[0428]
[0429]
[0430] [Delayed fluorescence material]
[0431] In an embodiment, the emission layer may further include a delayed fluorescent material.
[0432] In the specification, the delayed fluorescent material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0433] 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.
[0434] 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 satisfied within the above range, up-conversion of the delayed fluorescent material from the triplet state to the singlet state may effectively occur, and thus the organic light-emitting device 10 may have improved luminous efficiency.
[0435] In an embodiment, the delayed fluorescent material may include: at least one electron donor (eg, a π-electron-rich C 3 -C 60 a cyclic group, such as a carbazolyl group, etc.) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a π-electron-deficient nitrogen-containing C 1 -C 60 cyclic groups, etc.), or the delayed fluorescent material may include: a C in which two or more cyclic groups are fused while sharing boron (B) 8 -C 60 Polycyclic materials.
[0436] In an embodiment, the delayed fluorescent material may include at least one of Compound DF1 to Compound DF9:
[0437]
[0438] [Quantum dot]
[0439] In an embodiment, the emissive layer may include quantum dots.
[0440] In the specification, the 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.
[0441] The diameter of a quantum dot may be in the range of, for example, about 1 nm to about 10 nm.
[0442] The quantum dots can be synthesized by a wet chemical process, a metal organic chemical vapor deposition process (MOCVD), a molecular beam epitaxy process (MBE), or any similar process.
[0443] The wet chemical process is a method that includes 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 less expensive and easier to perform than a vapor deposition method (such as metal organic chemical vapor deposition or molecular beam epitaxy).
[0444] 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.
[0445] 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.
[0446] Examples of III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, 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.
[0447] 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 , InTe, etc.; ternary compounds, such as InGaS 3 、InGaSe 3 etc.; or any combination thereof.
[0448] Examples of Group I-III-VI semiconductor compounds may include: ternary compounds such as AgInS, AgInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 etc.; or any combination thereof.
[0449] Examples of Group IV-VI semiconductor compounds may include: binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe or PbTe; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, etc.; quaternary compounds, such as SnPbSSe, SnPbSeTe, SnPbSTe, etc.; or any combination thereof.
[0450] Examples of Group IV elements or compounds may include: single element materials, such as Si, Ge, etc.; binary compounds, such as SiC, SiGe, etc.; or any combination thereof.
[0451] Each element included in the multi-element compound such as a binary compound, a ternary compound, or a quaternary compound may be present in the particle at a uniform concentration or a non-uniform concentration.
[0452] 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. For example, the material included in the core and the material included in the shell may be different from each other.
[0453] 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, wherein the concentration of the material present in the shell decreases toward the center of the core.
[0454] Examples of the shell of the quantum dot may include: metal oxides, metalloid oxides, 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, Fe 2 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 4and 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.
[0455] The full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dot may be equal to or less than about 45 nm. For example, the FWHM of the emission wavelength spectrum of the quantum dot may be equal to or less than about 40 nm. For example, the FWHM of the emission wavelength spectrum of the quantum dot may be equal to or less than about 30 nm. Within these arbitrary ranges, the color purity or color reproducibility of the quantum dot may be improved. The light emitted by the quantum dot may be emitted in all directions so that the wide viewing angle may be improved.
[0456] In embodiments, the quantum dots may be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, and the like.
[0457] By controlling the size of the quantum dots, the energy band gap can be adjustable so that light with various wavelength bands can be obtained from the emission layer including the quantum dots. Accordingly, by using quantum dots of different sizes, an organic light-emitting device that emits light of various wavelengths can be realized. In an embodiment, the size of the quantum dots can be selected to emit red light, green light, and / or blue light. In an embodiment, the size of the quantum dots can be configured to emit white light by combining light of various colors.
[0458] [Electron Transport Region in Interlayer 130]
[0459] The electron transport region may have a structure composed of a layer (composed of a single material), a structure composed of a layer (composed of different materials), or a structure including a plurality of layers (including different materials).
[0460] 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.
[0461] 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 in their respective described order from the emission layer, but the structure of the electron transport region is not limited thereto.
[0462] 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.
[0463] In an embodiment, the electron transport region may include a compound represented by Formula 601:
[0464] [Formula 601]
[0465] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0466] In formula 601,
[0467] 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,
[0468] xe11 can be 1, 2 or 3,
[0469] xe1 can be 0, 1, 2, 3, 4 or 5,
[0470] R 601 may be 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 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601)、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),
[0471] Q 601 To Q 603 Can be independently compared with reference Q 1 Same as described,
[0472] xe21 can be 1, 2, 3, 4, or 5, and
[0473] 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.
[0474] 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.
[0475] In an embodiment, in Formula 601, Ar 601 may be unsubstituted or substituted with at least one R 10a Substituted anthracenyl.
[0476] In an embodiment, the electron transport region may include a compound represented by Formula 601-1:
[0477] [Formula 601-1]
[0478]
[0479] In formula 601-1,
[0480] X 614 Can be N or C(R 614 ), X 615 Can be N or C(R 615 ), and X 616 Can be N or C(R 616 ), where X 614 To X 616 At least one of them may each be N,
[0481] L 611 To L 613 Can be independently compared with reference L 601 Same as described,
[0482] xe611 to xe613 can each independently be the same as described with reference to xe1,
[0483] R 611 To R 613 Can be independently compared with reference R 601 Same as described, and
[0484] 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.
[0485] In an embodiment, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
[0486] In an embodiment, the electron transport region may include: one of Compound ET1 to Compound ET46; 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:
[0487]
[0488]
[0489]
[0490]
[0491] 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 hole blocking layer, the electron control layer, the electron transport layer and / or the electron transport region is within these ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.
[0492] In addition to the aforementioned materials, the electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material.
[0493] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ions of the alkali metal complex may be Li ions, Na ions, K ions, Rb ions, or Cs ions, and the metal ions of the alkaline earth metal complex may be Be ions, Mg ions, Ca ions, Sr ions, or Ba ions.
[0494] The ligands coordinated to the metal ion of the alkali metal complex or the metal ion of the alkaline earth metal complex can each independently include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.
[0495] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) or compound ET-D2:
[0496]
[0497] 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.
[0498] The electron injection layer may have a structure composed of a layer (composed of a single material), a structure composed of a layer including different materials, or a structure including a plurality of layers (including different materials).
[0499] In an embodiment, the electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0500] The alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0501] The alkali metal compound, alkaline earth metal compound, and rare earth metal compound may be oxides, halides (e.g., fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metals, alkaline earth metals, and rare earth metals, or any combination thereof.
[0502] 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 Te 3 、Nd 2 Te 3 、Pm 2 Te 3 、Sm 2 Te 3 、Eu 2Te 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.
[0503] 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 (e.g., hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof).
[0504] In an embodiment, the electron injection layer may be composed of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In an embodiment, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
[0505] 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.
[0506] In the case where 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.
[0507] 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 these ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0508] [Second electrode 150]
[0509] The second electrode 150 is disposed on the interlayer 130 having the aforementioned structure. 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, a conductive compound, or any combination thereof.
[0510] The second electrode 150 may include Li, Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, Yb, 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.
[0511] The second electrode 150 may have a single-layer structure or a multi-layer structure.
[0512] [Capping layer]
[0513] The organic light-emitting device 10 may include a first capping layer disposed outside the first electrode 110 and / or a second capping layer disposed outside the second electrode 150. In an embodiment, the organic 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 recited, 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 recited, 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 recited.
[0514] Light generated in the emission layer of the interlayer 130 of the organic light-emitting device 10 may be extracted to the outside through the first electrode 110 which may be a semi-transmissive electrode or a transmissive electrode and through the first capping layer. Light generated in the emission layer of the interlayer 130 of the organic light-emitting device 10 may be extracted to the outside through the second electrode 150 which may be a semi-transmissive electrode or a transmissive electrode and through the second capping layer.
[0515] The first capping layer and the second capping layer may each increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the organic light-emitting device 10 increases, so that the light emission efficiency of the organic light-emitting device 10 may be improved.
[0516] The first capping layer and the second capping layer may each include a material having a refractive index equal to or greater than about 1.6 (with respect to a wavelength of about 589 nm).
[0517] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
[0518] 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 be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.
[0519] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amine-containing compound.
[0520] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0521] 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:
[0522]
[0523]
[0524] [membrane]
[0525] The organometallic compound represented by Formula 1 may be included in various films. Therefore, 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, or a quantum dot content layer, etc.), a light blocking member (e.g., a light reflecting layer or a light absorbing layer, etc.), or a protective member (e.g., an insulating layer or a dielectric layer, etc.), etc.
[0526] [Electronic equipment]
[0527] The organic light-emitting device may be included in various electronic devices. For example, the electronic device including the organic light-emitting device may be a light-emitting device, an authentication device, and the like.
[0528] In addition to the organic light-emitting device, the electronic device (e.g., a 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 organic light-emitting device. For example, the light emitted from the organic light-emitting device may be blue light or white light. The organic light-emitting device may be the same as described above. In an embodiment, the color conversion layer may include quantum dots. The quantum dots may be, for example, quantum dots as described above.
[0529] The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixels, the color filter may include a plurality of color filter regions respectively corresponding to the plurality of sub-pixels, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixels.
[0530] A pixel defining layer may be disposed between the plurality of sub-pixels to define each sub-pixel.
[0531] The color filter may further include a plurality of color filter regions and a light shielding pattern disposed between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light shielding pattern disposed between the plurality of color conversion regions.
[0532] The color filter region (or color conversion region) 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. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the color filter region (or color conversion region) may include quantum dots. For example, 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. More details about quantum dots may be the same as described herein. Each of the first region, the second region, and / or the third region may further include a scatterer.
[0533] In an embodiment, the organic 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. For example, 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.
[0534] In addition to the aforementioned organic 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 organic light-emitting device.
[0535] The thin film transistor may further include a gate electrode, a gate insulating film, and the like.
[0536] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and the like.
[0537] The electronic device may further include a sealing portion for sealing the organic light-emitting device. The sealing portion may be arranged between the color filter and / or the color conversion layer and the organic light-emitting device. The sealing portion allows light from the organic light-emitting device to be extracted to the outside, and at the same time prevents ambient air and moisture from penetrating into the organic 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.
[0538] In addition to the color filter and / or color conversion layer, various functional layers may be further included on the sealing portion according to the purpose of the electronic device. 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.
[0539] In addition to the organic light emitting device as described above, the authentication device may further include a biometric information collector. The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (eg, fingertips, pupils, etc.).
[0540] The electronic device can be applied to various displays, light sources, lighting equipment, 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) and projectors, etc.
[0541] [Electronic equipment]
[0542] Organic light emitting devices may be included in various types of electronic equipment.
[0543] In an embodiment, the electronic equipment including the organic light-emitting device may be a flat panel display, a curved display, a computer monitor, a medical monitor, a TV, 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 retractable display, a laser printer, a phone, a mobile phone, a tablet personal computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater screen, a stadium screen, a light therapy device, a sign, a car sensor, a home sensor, or a solar cell.
[0544] Since the organic light-emitting device has excellent photoelectric properties, etc., an electronic device including the organic light-emitting device may have an optical sensor function, such as a fingerprint recognition sensor, etc.
[0545] [ Figure 2 and Figure 3 Description]
[0546] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment.
[0547] Figure 2 The electronic device (eg, a light emitting device) includes a substrate 100, a thin film transistor (TFT), an organic light emitting device, and an encapsulation portion encapsulating the organic light emitting device.
[0548] 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 provide a flat surface on the substrate 100.
[0549] 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.
[0550] The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0551] 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 .
[0552] An interlayer insulating film 250 may be disposed on the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate these electrodes from each other.
[0553] 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.
[0554] The TFT may be electrically connected to the organic light-emitting device to drive the organic 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 organic light-emitting device may be provided on the passivation layer 280. The organic light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
[0555] 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 connected (eg, electrically connected) to the exposed portion of the drain electrode 270.
[0556] 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 on 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 , but at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 to be provided in the form of a common layer.
[0557] 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.
[0558] The encapsulation portion 300 may be disposed on the capping layer 170. The encapsulation portion 300 may be disposed on the organic light-emitting device to protect the organic light-emitting device from moisture and / or oxygen. The encapsulation portion 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, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy resin (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of an inorganic film and an organic film.
[0559] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment.
[0560] Figure 3 The electronic device (such as a light emitting device) may be different from Figure 2 The electronic device of at least one embodiment of the present invention is further provided with a light shielding pattern 500 and a functional area 400 on the packaging portion 300. 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. Figure 3 The organic light-emitting device included in the electronic device may be a tandem organic light-emitting device.
[0561] [ Figure 4 Description]
[0562] Figure 4 is a schematic perspective view of an electronic device 1 including an organic light-emitting device according to an embodiment.
[0563] The electronic device 1 (which may be a device for displaying a moving image or a still image) may be not only 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 electronic book, a portable multimedia player (PMP), a navigation device, or an ultra mobile PC (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.
[0564] In an embodiment, 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 such a wearable device. However, the embodiments of the present disclosure are not limited thereto.
[0565] Examples of the electronic device 1 may include 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 rearview 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) mounted on the front of the vehicle or projected on the 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.
[0566] The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device may realize an image through a two-dimensional array of pixels arranged in the display area DA.
[0567] The non-display area NDA is an area where no image is displayed, and may surround (e.g., completely 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 may be arranged in the non-display area NDA, and the pad may be electrically connected to an electronic element or a printed circuit board.
[0568] 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 In the embodiment 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.
[0569] [ Figure 5 and FIG. 6A to FIG. 6C Description]
[0570] Figure 5 is a schematic perspective view of the exterior of a vehicle 1000 as an electronic device including an organic 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.
[0571] See also 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 (such as a person, object, or animal) from a starting point to a destination point. Examples of the vehicle 1000 may include a vehicle traveling on roads or tracks, a ship moving on the ocean or river, and an airplane flying in the air using the action of air.
[0572] The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a selected or given direction according to the rotation of at least one wheel. Examples of the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, an engineering machine, a two-wheeled vehicle, a prime mover device, a bicycle, and a train traveling on a track.
[0573] The vehicle 1000 may include a body having an interior and an exterior, and a chassis, which is a portion other than the body on which mechanical equipment required for driving is installed. The exterior of the body of the vehicle 1000 may include a front panel, a hood, a roof panel, a rear panel, a trunk, and pillars provided at the boundaries between the 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, and front and rear left and right wheels, etc.
[0574] The vehicle 1000 may include side windows 1100 , a front window 1200 , side mirrors 1300 , an instrument cluster 1400 , a center console 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0575] The side window glass 1100 and the front window glass 1200 may be divided by pillars disposed between the side window glass 1100 and the front window glass 1200 .
[0576] The side window glass 1100 may be installed on the side of the vehicle 1000. In an embodiment, the side window glass 1100 may be installed 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 cluster 1400, and the second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.
[0577] In an embodiment, the side window glass 1100 may be spaced apart from each other in the x-axis direction or the -x-axis direction (the 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 the -x-axis direction. For example, the virtual straight line L connecting the side window glass 1100 may extend in the x-axis direction or the -x-axis direction. For example, the virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x-axis direction or the -x-axis direction.
[0578] 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.
[0579] The side view mirror 1300 may provide a rear view of the vehicle 1000. The side view mirror 1300 may be mounted on the exterior of the vehicle body of the vehicle 1000. In an embodiment, a plurality of side view mirrors 1300 may be provided. For example, one of the plurality of side view mirrors 1300 may be disposed outside the first side window glass 1110, and another of the plurality of side view mirrors 1300 may be disposed outside the second side window glass 1120.
[0580] Instrument cluster 1400 may be arranged in front of the steering wheel. Instrument cluster 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn signal indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a trip meter, an automatic shift lever indicator light, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0581] 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 provided. The center console 1500 may be disposed on one side of the instrument cluster 1400 .
[0582] The passenger seat instrument panel 1600 may be spaced apart from the instrument cluster 1400, and the center console 1500 may be disposed between the instrument cluster 1400 and the passenger seat instrument panel 1600. In an embodiment, the instrument cluster 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 cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.
[0583] 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 cluster 1400, the center console 1500, and the passenger seat instrument panel 1600.
[0584] The display device 2 may include an organic light emitting display device, an inorganic electroluminescent display device, a quantum dot display device, etc. Hereinafter, an organic light emitting display device including the aforementioned organic light emitting device will be described as an example of the display device 2. However, various types of the aforementioned display devices may be used in embodiments.
[0585] See also 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.
[0586] See also Figure 6B , the display device 2 may be arranged on the instrument cluster 1400. When the display device 2 is arranged on the instrument cluster 1400, the instrument cluster 1400 may display driving information, etc. through the display device 2. For example, the instrument cluster 1400 may digitally implement driving information, etc. The instrument cluster 1400 may digitally display vehicle information and driving information as images. For example, the pointer and instrument of the tachometer and various warning lights or icons may be displayed through digital signals.
[0587] See also 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 an image related to the information displayed on the instrument cluster 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 cluster 1400 and / or the information displayed on the center console 1500.
[0588] [Manufacturing method]
[0589] 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.
[0590] 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 about 100° C. to about 500° C., about 10 -8 To about 10 -3 Torr vacuum and approx. to about Deposition is carried out at a deposition rate of .
[0591] [Definition of terms]
[0592] As used herein, the term "C 3 -C 60 The term "carbocyclic group" as used herein may be a cyclic group consisting of only carbon atoms as ring-forming atoms and having 3 to 60 carbon atoms. 1 -C 60 The "heterocyclic group" may be a cyclic group having 1 to 60 carbon atoms and further having at least one hetero atom 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 number of ring-forming atoms in the heterocyclic group may be 3 to 61.
[0593] As used herein, the term "cyclic group" may be C 3 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group.
[0594] 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 part. 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.
[0595] In an embodiment,
[0596] 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., a cyclopentadienyl group, an adamantyl group, a norbornyl group, a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylene group, a pyrenyl group, a 1,2-triphenylene group, a peryl group, a pentaphenanthrenyl group, a heptalenyl group, a tetracenyl group, a phenanthrenyl group, a hexacenyl group, a pentacenyl group, a rubidenyl group, a coronenyl group, an ovalenyl group, an indenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, or an indenoanthryl group),
[0597] C 1 -C 60The heterocyclic group may be a T2 group, a group in which at least two 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 benzothioyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzothioyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an indenocarbazolyl group, an indolcarbazolyl group, a benzofuranocarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiophenylcarbazolyl group, a benzoindolcarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranoyl group, a benzonaphthothiophenyl group, a benzonaphthothioyl group, a benzofuranodibenzofuranodibenzothiophenyl group, a ... 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 or azadibenzofuranyl, etc.),
[0598] 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, borocyclopentadienyl, 2H-pyrrolyl, 3H-pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolecarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiolyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl or benzothiophenyldibenzothiophenyl, etc.),
[0599] π-electron-deficient nitrogen-containing C 1 -C 60The cyclic group may be a T4 group, a group in which at least two 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, benzoxazolyl, , 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, azadibenzothiolsyl, azadibenzothiophenyl and azadibenzofuranyl, etc.), wherein
[0600] The T1 group can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo[2.2.1]heptane) group, norbornyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane or phenyl,
[0601] 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,
[0602] The T3 group may be a furyl group, a thienyl group, a 1H-pyrrolyl group, a thiole group or a borocyclopentadienyl group, and
[0603] 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.
[0604] As used herein, the terms "cyclic group", "C3 -C 60 Carbocyclic group, "C 1 -C 60 Heterocyclic group", "π-electron-rich C 3 -C 60 Cyclic groups" and "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. In an embodiment, the "phenyl group" may be a benzo group, a phenyl group or a phenylene group, etc., and those of ordinary skill in the art may easily understand these groups based on the structure of the formula including the "phenyl group".
[0605] Unit Price C 3 -C 60 Carbocyclic or 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 or 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.
[0606] As used herein, the term "C 1 -C 60The “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, and tert-decyl. As used herein, the term “C 1 -C 60 The "alkylene" may be 1 -C 60 The alkyl group has substantially the same structure as a divalent group.
[0607] 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 The alkenyl group has a divalent group having substantially the same structure.
[0608] 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 groups have substantially the same structure as a divalent group.
[0609] 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.
[0610] 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]octyl. 3 -C 10 The cycloalkylene group may be 3 -C 10 The cycloalkyl group has a divalent group having substantially the same structure.
[0611] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl" as used herein may be a monovalent cyclic group having 1 to 10 carbon atoms which further includes at least one hetero atom 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. 1 -C 10 The heterocycloalkylene group may be 1 -C 10 The heterocycloalkyl group has substantially the same structure as a divalent group.
[0612] As used herein, the term "C 3 -C 10 The term "cycloalkenyl" as used herein may be a monovalent cyclic group having 3 to 10 carbon atoms, at least one carbon-carbon double bond, and no aromaticity in its ring structure, and examples thereof may include cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like. 3 -C 10 The cycloalkenylene group may be 3 -C 10 The cycloalkenyl group has a divalent group having substantially the same structure.
[0613] As used herein, the term "C 1 -C 10 The "heterocycloalkenyl group" may be a monovalent cyclic group having 1 to 10 carbon atoms, further including at least one heteroatom as a ring-forming atom and at least one double bond in addition to carbon atoms in its ring structure. 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 has a divalent group having substantially the same structure.
[0614] 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 two or more rings may be fused to each other.
[0615] As used herein, the term "C 1 -C 60 The term "heteroaryl" as used herein 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 two or more rings may be fused to each other.
[0616] The term "monovalent non-aromatic fused polycyclic group" as used herein may be a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other, only carbon atoms as ring-forming atoms, and generally having no aromaticity in the molecular structure. Examples of monovalent non-aromatic fused polycyclic groups may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl, indenoanthryl, and the like. The term "divalent non-aromatic fused polycyclic group" as used herein may be a divalent group having substantially the same structure as the above-mentioned monovalent non-aromatic fused polycyclic group.
[0617] The term “monovalent non-aromatic fused heteropolycyclic group” as used herein 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 no aromaticity in its molecular structure as a whole. 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 substantially the same structure as a monovalent non-aromatic condensed heteropolycyclic group.
[0618] As used herein, the term "C 6 -C 60 "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.
[0619] 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.
[0620] In the specification, the group "R 10a " can be:
[0621] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0622] 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 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q11 )(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;
[0623] 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 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, 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 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, 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
[0624] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ).
[0625] In the manual, Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 alkoxy; or each 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 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.
[0626] The term "heteroatom" as used herein 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, and any combination thereof.
[0627] The term "Ph" as used herein refers to a phenyl group, the term "Me" as used herein refers to a methyl group, the term "Et" as used herein refers to an ethyl group, and the terms "tert-Bu" or "Bu" as used herein refer to an ethyl group. t ” each refers to a tert-butyl group, and the term “OMe” as used herein refers to a methoxy group.
[0628] As used herein, the term "biphenyl" may be a "phenyl group substituted with a phenyl group". For example, a "biphenyl group" may be a group having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0629] The term "terphenyl" as used herein 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.
[0630] In the specification, the terms "x-axis", "y-axis", and "z-axis" are not limited to the three axes in an orthogonal coordinate system (e.g., a Cartesian coordinate system), and may be interpreted in a broader sense as the aforementioned three axes in an 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.
[0631] In the specification, unless otherwise defined, the symbols *, *' and *" as used herein each refer to a binding site to an adjacent atom in the corresponding formula or moiety.
[0632] Hereinafter, a compound according to an embodiment and an organic light-emitting device according to an embodiment will be described in detail with reference to Synthesis Examples and Examples. The expression "using B instead of A" used in describing Synthesis Examples means using B instead of A in the same molar equivalent.
[0633] [Example]
[0634] Synthesis Example 1: Synthesis of Compound 9
[0635]
[0636] (Synthesis of Intermediate 9-1)
[0637] 5.6g (18mmol) of 5,6-diisobutyl-2-methoxy-9H-carbazole, 5.8g (27mmol) of 2-bromo-4 (tert-butyl) pyridine, 8.3g (36mmol) of tripotassium phosphate, 0.66g (3.6mmol) of CuI and 0.4g (3.6mmol) of picolinic acid were added to a reaction vessel and suspended in 100mL of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160°C and stirred for 24 hours. After the reaction was completed, the resulting product was cooled at room temperature, 100ml of distilled water was added thereto, and an extraction process was performed on it by using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 6.3g (14.2mmol) of the target compound.
[0638] (Synthesis of Intermediate 9-2)
[0639] 6.3g (14.2mmol) of intermediate 9-1 was suspended in an excess of bromic acid solution. The reaction mixture was heated to 110°C and stirred for 24 hours. After the reaction was completed, the resulting product was cooled at room temperature and an appropriate amount of sodium bicarbonate was added thereto for neutralization. 100ml of distilled water was added thereto and an extraction process was performed on it by using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 4.8g (11.3mmol) of the target compound.
[0640] (Synthesis of Intermediate 9-3)
[0641] 4.8g (11.3mmol) of intermediate 9-2, 3.0g (17.0mmol) of 1-bromo-3-fluorobenzene and 5.3g (22.6mmol) of tripotassium phosphate are added to the reaction vessel and suspended in 110mL of dimethyl sulfoxide. The reaction mixture is heated to a temperature of 160°C and stirred for 12 hours. After the reaction is complete, the product therefrom is cooled at room temperature, 100ml of distilled water is added thereto, and an extraction process is performed on it by using ethyl acetate. The organic layer extracted therefrom is washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent has been removed is separated by column chromatography to obtain 5.1g (8.7mmol) of the target compound.
[0642] (Synthesis of Intermediate 9-4)
[0643] 5.1 g (8.7 mmol) of intermediate 9-3, 2.9 g (8.7 mmol) of N1-([1,1':3',1"-terphenyl]-2'-yl)benzene-1,2-diamine, SPhos (0.66 mmol), Pd 2 (dba) 3 4g (7.6mmol) of the target compound was obtained by mixing 1.4g (0.44mmol) and sodium tert-butoxide (17.4mmol) in 90ml of toluene solvent and stirring for 4 hours after the temperature was raised to 110°C. After the reaction was completed, the solvent was removed therefrom under reduced pressure and an extraction process was performed using dichloromethane and distilled water. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 6.4g (7.6mmol) of the target compound.
[0644] (Synthesis of Intermediate 9-5)
[0645] 6.4g (7.6mmol) of intermediate 9-4 was dissolved in 63mmol of triethyl orthoformate, and 9.1mmol of HCl was added dropwise thereto. The reaction mixture was heated to a temperature of 80°C and stirred for 20 hours. After the reaction was completed, the solvent was removed therefrom under reduced pressure, and an extraction process was performed on it by using dichloromethane and distilled water. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 6.1g (6.8mmol) of the target compound.
[0646] (Synthesis of Compound 9)
[0647] 6.1 g (6.8 mmol) of intermediate 9-5, 3.1 g (7.5 mmol) of potassium chloroplatinate and 2.9 g (27.5 mmol) of 2,6-lutidine were suspended in 130 mL of 1,2-dichlorobenzene. The reaction mixture was heated to 120 ° C and stirred for 18 hours. After the reaction was completed, the resulting product was cooled to room temperature, the solvent was removed therefrom, and the residue was separated by column chromatography to obtain 3.0 g (2.9 mmol) of the target compound.
[0648] Synthesis Example 2: Synthesis of Compound 20
[0649]
[0650] (Synthesis of Intermediate 20-2)
[0651] 6.6g (18mmol) of intermediate 20-1, 5.8g (27mmol) of 2-bromo-4 (tert-butyl) pyridine, 8.3g (36mmol) of tripotassium phosphate, 0.66g (3.6mmol) of CuI and 0.4g (3.6mmol) of picolinic acid were added to a reaction vessel and suspended in 100mL of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160°C and stirred for 24 hours. After the reaction was completed, the product was cooled at room temperature, 100ml of distilled water was added thereto, and an extraction process was performed on it using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 6.9g (13.7mmol) of the target compound.
[0652] (Synthesis of Intermediate 20-3)
[0653] 6.9g (13.7mmol) of intermediate 20-2 is added to a reaction vessel and suspended in 130mL of dichloromethane. After stirring the reaction mixture at 0°C, boron tribromide is slowly added dropwise thereto. After the temperature is raised to room temperature, the resulting mixture is stirred for 2 hours, 200mL of distilled water is added thereto, and an extraction process is performed on it using dichloromethane. The organic layer extracted therefrom is washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent has been removed is separated by column chromatography to obtain 4.4g (9.0mmol) of the target compound.
[0654] (Synthesis of Intermediate 20-4)
[0655] 4.4g (9.0mmol) of intermediate 20-3, 3.7g (13.5mmol) of intermediate A-1, 4.2g (18mmol) of tripotassium phosphate, 0.33g (0.18mmol) of CuI and 0.02g (0.18mmol) of picolinic acid are added to a reaction vessel and suspended in 90mL of dimethyl sulfoxide. The reaction mixture is heated to a temperature of 160°C and stirred for 20 hours. After the reaction is complete, the reaction product is cooled at room temperature, 100ml of distilled water is added thereto, and an extraction process is performed on it by using ethyl acetate. The organic layer extracted therefrom is washed with a saturated sodium chloride aqueous solution, and is dried by using sodium sulfate. The residue from which the solvent has been removed is separated by column chromatography to obtain 4.4g (6.5mmol) of the target compound.
[0656] (Synthesis of Intermediate 20-5)
[0657] 4.4 g (6.5 mmol) of Intermediate 20-4, 5.7 g (9.8 mmol) of Intermediate A-2 and 0.12 g (0.65 mmol) of Cu(OAc) were added. 2 Add to dimethyl sulfoxide, after raising the temperature to 150 ℃, stir the reaction mixture for 12 hours. After the reaction is completed, the resulting product is cooled at room temperature, 100 ml of distilled water is added thereto, and an extraction process is performed on it by using ethyl acetate. The organic layer extracted therefrom is washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent is removed is separated by column chromatography to obtain 4.6 g (4.5 mmol) of the target compound.
[0658] (Synthesis of Compound 20)
[0659] 4.6 g (4.5 mmol) of intermediate 20-5, 2.1 g (5.0 mmol) of potassium chloroplatinate and 1.9 g (18.2 mmol) of 2,6-lutidine were suspended in 90 mL of 1,2-dichlorobenzene. The reaction mixture was heated to 120 ° C and stirred for 18 hours. After the reaction was completed, the resulting product was cooled to room temperature, the solvent was removed therefrom, and the residue was separated by column chromatography to obtain 1.9 g (1.8 mmol) of the target compound.
[0660] Synthesis Example 3: Synthesis of Compound 31
[0661]
[0662] (Synthesis of Intermediate 31-2)
[0663] 5.8g (18mmol) of intermediate 31-1, 5.8g (27mmol) of 2-bromo-4 (tert-butyl) pyridine, 8.3g (36mmol) of tripotassium phosphate, 0.66g (3.6mmol) of CuI and 0.4g (3.6mmol) of picolinic acid were added to a reaction vessel and suspended in 100mL of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160°C and stirred for 24 hours. After the reaction was completed, the product obtained was cooled at room temperature, 100ml of distilled water was added thereto, and an extraction process was performed on it using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 7.0g (15.3mmol) of the target compound.
[0664] (Synthesis of Intermediate 31-3)
[0665] 7.0g (15.3mmol) of intermediate 31-2 was suspended in an excess of bromic acid solution. The reaction mixture was heated to 110°C and stirred for 24 hours. After the reaction was completed, the resulting product was cooled at room temperature and an appropriate amount of sodium bicarbonate was added thereto for neutralization. 100ml of distilled water was added thereto and an extraction process was performed on it by using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 5.2g (11.8mmol) of the target compound.
[0666] (Synthesis of Intermediate 31-4)
[0667] 5.2g (11.8mmol) of intermediate 31-3, 3.1g (17.7mmol) of 1-bromo-3-fluorobenzene and 5.5g (23.6mmol) of tripotassium phosphate are added to a reaction vessel and suspended in 120mL of dimethyl sulfoxide. The reaction mixture is heated to a temperature of 160°C and stirred for 12 hours. After the reaction is complete, the product therefrom is cooled at room temperature, 100ml of distilled water is added thereto, and an extraction process is performed on it by using ethyl acetate. The organic layer extracted therefrom is washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent has been removed is separated by column chromatography to obtain 5.3g (8.9mmol) of the target compound.
[0668] (Synthesis of Intermediate 31-5)
[0669] 5.3 g (8.9 mmol) of Intermediate 31-4, 4.6 g (8.9 mmol) of Intermediate A-3, SPhos (0.68 mmol), Pd 2 (dba) 3 8.2g (8.0mmol) of target compound was obtained by mixing 1.4g (0.45mmol) and sodium tert-butoxide (17.8mmol) in 90mL of toluene solvent and stirring for 4 hours after the temperature was raised to 110°C. After the reaction was completed, the solvent was removed therefrom under reduced pressure, and an extraction process was performed using dichloromethane and distilled water. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 8.2g (8.0mmol) of the target compound.
[0670] (Synthesis of Intermediate 31-6)
[0671] 8.2g (8.0mmol) of intermediate 31-5 was dissolved in 66mmol of triethyl orthoformate, and 9.6mmol of HCl was added dropwise thereto. The reaction mixture was heated to a temperature of 80°C and stirred for 20 hours. After the reaction was completed, the solvent was removed therefrom under reduced pressure, and an extraction process was performed on it by using dichloromethane and distilled water. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 6.7g (6.2mmol) of the target compound.
[0672] (Synthesis of Compound 31)
[0673] 6.7 g (6.2 mmol) of intermediate 31-6, 2.8 g (6.8 mmol) of potassium chloroplatinate and 2.6 g (25.1 mmol) of 2,6-lutidine were suspended in 120 mL of 1,2-dichlorobenzene. The reaction mixture was heated to a temperature of 120° C. and stirred for 18 hours. After the reaction was completed, the resulting product was cooled to room temperature, the solvent was removed therefrom, and the residue was separated by column chromatography to obtain 3.2 g (2.6 mmol) of the target compound.
[0674] Synthesis Example 4: Synthesis of Compound 43
[0675]
[0676] (Synthesis of Intermediate 43-1)
[0677] 5.6g (18mmol) of 1,3-diisobutyl-7-methoxy-9H-carbazole, 5.8g (27mmol) of 2-bromo-4 (tert-butyl) pyridine, 8.3g (36mmol) of tripotassium phosphate, 0.66g (3.6mmol) of CuI and 0.4g (3.6mmol) of picolinic acid were added to a reaction vessel and suspended in 100mL of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160°C and stirred for 24 hours. After the reaction was completed, the resulting product was cooled at room temperature, 100ml of distilled water was added thereto, and an extraction process was performed on it by using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 5.4g (12.3mmol) of the target compound.
[0678] (Synthesis of Intermediate 43-2)
[0679] 5.4g (12.3mmol) of intermediate 43-1 was suspended in an excess of bromic acid solution. The reaction mixture was heated to 110°C and stirred for 24 hours. After the reaction was completed, the resulting product was cooled at room temperature and an appropriate amount of sodium bicarbonate was added thereto for neutralization. 100ml of distilled water was added thereto and an extraction process was performed on it by using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 4.2g (9.9mmol) of the target compound.
[0680] (Synthesis of Intermediate 43-3)
[0681] 4.2g (9.9mmol) of intermediate 43-2, 2.9g (14.9mmol) of 1-bromo-3-fluorobenzene and 4.6g (19.8mmol) of tripotassium phosphate are added to a reaction vessel and suspended in 100mL of dimethyl sulfoxide. The reaction mixture is heated to a temperature of 160°C and stirred for 12 hours. After the reaction is complete, the product therefrom is cooled at room temperature, 100ml of distilled water is added thereto, and an extraction process is performed on it by using ethyl acetate. The organic layer extracted therefrom is washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent has been removed is separated by column chromatography to obtain 4.7g (8.1mmol) of the target compound.
[0682] (Synthesis of Intermediate 43-4)
[0683] 4.7 g (8.1 mmol) of intermediate 43-3, 2.7 g (8.1 mmol) of N1-([1,1':3',1"-terphenyl]-2'-yl)benzene-1,2-diamine, SPhos (0.61 mmol), Pd 2 (dba) 3 4-(4-(4-(4-(4-oxo-1-yl)-2-nitropropene)-1 ...
[0684] (Synthesis of Intermediate 43-5)
[0685] 6.0g (7.1mmol) of intermediate 43-4 was dissolved in 60mmol of triethyl orthoformate, and 8.5mmol of HCl was added dropwise thereto. The reaction mixture was heated to a temperature of 80°C and stirred for 20 hours. After the reaction was completed, the solvent was removed therefrom under reduced pressure, and an extraction process was performed using dichloromethane and distilled water. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 5.0g (5.7mmol) of the target compound.
[0686] (Synthesis of Compound 43)
[0687] 5.0 g (5.7 mmol) of intermediate 43-5, 2.6 g (6.3 mmol) of potassium chloroplatinate and 2.4 g (23.0 mmol) of 2,6-lutidine were suspended in 120 mL of 1,2-dichlorobenzene. The reaction mixture was heated to 120 ° C and stirred for 18 hours. After the reaction was completed, the resulting product was cooled to room temperature, the solvent was removed therefrom, and the residue was separated by column chromatography to obtain 2.3 g (2.2 mmol) of the target compound.
[0688] Synthesis Example 5: Synthesis of Compound 65
[0689]
[0690] (Synthesis of Intermediate 65-2)
[0691] 6.3g (18mmol) of intermediate 65-1, 5.8g (27mmol) of 2-bromo-4 (tert-butyl) pyridine, 8.3g (36mmol) of tripotassium phosphate, 0.66g (3.6mmol) of CuI and 0.4g (3.6mmol) of picolinic acid were added to a reaction vessel and suspended in 100mL of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160°C and stirred for 24 hours. After the reaction was completed, the product was cooled at room temperature, 100ml of distilled water was added thereto, and an extraction process was performed on it using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 7.1g (14.7mmol) of the target compound.
[0692] (Synthesis of Intermediate 65-3)
[0693] 7.1g (14.7mmol) of intermediate 65-2 was suspended in an excess of bromic acid solution. The reaction mixture was heated to 110°C and stirred for 24 hours. After the reaction was completed, the resulting product was cooled at room temperature and an appropriate amount of sodium bicarbonate was added thereto for neutralization. 100ml of distilled water was added thereto and an extraction process was performed using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 5.2g (11.1mmol) of the target compound.
[0694] (Synthesis of Intermediate 65-4)
[0695] 5.2g (11.1mmol) of intermediate 65-3, 2.9g (16.7mmol) of 1-bromo-3-fluorobenzene and 5.2g (22.2mmol) of tripotassium phosphate were added to the reaction vessel and suspended in 110mL of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160°C and stirred for 12 hours. After the reaction was completed, the product therefrom was cooled at room temperature, 100ml of distilled water was added thereto, and an extraction process was performed on it by using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 5.1g (8.2mmol) of the target compound.
[0696] (Synthesis of Intermediate 65-5)
[0697] 5.1 g (8.2 mmol) of intermediate 65-4, 4.2 g (8.2 mmol) of intermediate A-5, SPhos (0.63 mmol), Pd 2 (dba) 3 7.2g (7.2mmol) of target compound was obtained by mixing 1.4g (0.41mmol) and sodium tert-butoxide (16.4mmol) in 80mL of toluene solvent and stirring for 4 hours after the temperature was raised to 110°C. After the reaction was completed, the solvent was removed therefrom under reduced pressure, and an extraction process was performed on it by using dichloromethane and distilled water. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 7.2g (7.2mmol) of target compound.
[0698] (Synthesis of Intermediate 65-6)
[0699] 7.2g (7.2mmol) of intermediate 65-5 was dissolved in 60mmol of triethyl orthoformate, and 8.6mmol of HCl was added dropwise thereto. The reaction mixture was heated to a temperature of 80°C and stirred for 20 hours. After the reaction was completed, the solvent was removed therefrom under reduced pressure, and an extraction process was performed on it by using dichloromethane and distilled water. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 6.6g (6.3mmol) of the target compound.
[0700] (Synthesis of Compound 65)
[0701] 6.6 g (6.3 mmol) of intermediate 65-6, 2.8 g (6.8 mmol) of potassium chloroplatinate and 2.6 g (25.5 mmol) of 2,6-lutidine were suspended in 120 mL of 1,2-dichlorobenzene. The reaction mixture was heated to a temperature of 120° C. and stirred for 18 hours. After the reaction was completed, the resulting product was cooled to room temperature, the solvent was removed therefrom, and the residue was separated by column chromatography to obtain 3.6 g (3.0 mmol) of the target compound.
[0702] Synthesis Example 6: Synthesis of Compound 75
[0703]
[0704] (Synthesis of Intermediate 75-2)
[0705] 5.6g (18mmol) of intermediate 75-1, 5.8g (27mmol) of 2-bromo-4 (tert-butyl) pyridine, 8.3g (36mmol) of tripotassium phosphate, 0.66g (3.6mmol) of CuI and 0.4g (3.6mmol) of picolinic acid were added to a reaction vessel and suspended in 100mL of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160°C and stirred for 24 hours. After the reaction was completed, the product was cooled at room temperature, 100ml of distilled water was added thereto, and an extraction process was performed on it using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 6.3g (14.1mmol) of the target compound.
[0706] (Synthesis of Intermediate 75-3)
[0707] 6.3g (14.1mmol) of intermediate 75-2 is added to a reaction vessel and suspended in 140mL of dichloromethane. After stirring the reaction mixture at 0°C, boron tribromide is slowly added dropwise thereto. After the temperature is raised to room temperature, the resulting mixture is stirred for 2 hours, 200mL of distilled water is added thereto, and an extraction process is performed on it using dichloromethane. The organic layer extracted therefrom is washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent has been removed is separated by column chromatography to obtain 4.9g (11.3mmol) of the target compound.
[0708] (Synthesis of Intermediate 75-4)
[0709] 4.9g (11.3mmol) of intermediate 75-3, 3.0g (17.0mmol) of 1-bromo-3-fluorobenzene and 5.3g (22.6mmol) of tripotassium phosphate are added to a reaction vessel and suspended in 110mL of dimethyl sulfoxide. The reaction mixture is heated to a temperature of 160°C and stirred for 12 hours. After the reaction is complete, the product therefrom is cooled at room temperature, 100ml of distilled water is added thereto, and an extraction process is performed on it by using ethyl acetate. The organic layer extracted therefrom is washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent has been removed is separated by column chromatography to obtain 5.0g (8.5mmol) of the target compound.
[0710] (Synthesis of Intermediate 75-5)
[0711] 5.0 g (8.5 mmol) of intermediate 75-4, 2.8 g (8.5 mmol) of N1-([1,1':3',1"-terphenyl]-2'-yl)benzene-1,2-diamine, SPhos (0.64 mmol), Pd 2 (dba) 3 In the reaction mixture, 1,4-dichloro-2-nitropropene (0.43mmol) and sodium tert-butoxide (17.0mmol) were suspended in 90ml of toluene solvent and stirred for 4 hours after the temperature was raised to 110°C. After the reaction was completed, the solvent was removed therefrom under reduced pressure and an extraction process was performed using dichloromethane and distilled water. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 6.1g (7.2mmol) of the target compound.
[0712] (Synthesis of Intermediate 75-6)
[0713] 6.1g (7.2mmol) of intermediate 75-5 was dissolved in 60mmol of triethyl orthoformate, and 8.6mmol of HCl was added dropwise thereto. The reaction mixture was heated to a temperature of 80°C and stirred for 20 hours. After the reaction was completed, the solvent was removed therefrom under reduced pressure, and an extraction process was performed on it by using dichloromethane and distilled water. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 5.6g (6.3mmol) of the target compound.
[0714] (Synthesis of Compound 75)
[0715] 5.6 g (6.3 mmol) of intermediate 75-6, 2.9 g (6.9 mmol) of potassium chloroplatinate and 2.7 g (25.4 mmol) of 2,6-lutidine were suspended in 120 mL of 1,2-dichlorobenzene. The reaction mixture was heated to 120 ° C and stirred for 18 hours. After the reaction was completed, the resulting product was cooled to room temperature, the solvent was removed therefrom, and the residue was separated by column chromatography to obtain 2.7 g (2.6 mmol) of the target compound.
[0716] Synthesis Example 7: Synthesis of Compound 85
[0717]
[0718] (Synthesis of Intermediate 85-2)
[0719] 5.6g (18mmol) of intermediate 85-1, 5.8g (27mmol) of 2-bromo-4 (tert-butyl) pyridine, 8.3g (36mmol) of tripotassium phosphate, 0.66g (3.6mmol) of CuI and 0.4g (3.6mmol) of picolinic acid were added to a reaction vessel and suspended in 100mL of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160°C and stirred for 24 hours. After the reaction was completed, the product was cooled at room temperature, 100ml of distilled water was added thereto, and an extraction process was performed on it using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 6.4g (14.5mmol) of the target compound.
[0720] (Synthesis of Intermediate 85-3)
[0721] 6.4g (14.5mmol) of intermediate 85-2 was suspended in an excess of bromic acid solution. The reaction mixture was heated to 110°C and stirred for 24 hours. After the reaction was completed, the resulting product was cooled at room temperature and an appropriate amount of sodium bicarbonate was added thereto for neutralization. 100ml of distilled water was added thereto and an extraction process was performed using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 5.0g (11.7mmol) of the target compound.
[0722] (Synthesis of Intermediate 85-4)
[0723] 5.0g (11.7mmol) of intermediate 85-3, 3.1g (17.6mmol) of 1-bromo-3-fluorobenzene and 5.5g (23.4mmol) of tripotassium phosphate were added to the reaction vessel and suspended in 120mL of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160°C and stirred for 12 hours. After the reaction was completed, the product therefrom was cooled at room temperature, 100ml of distilled water was added thereto, and an extraction process was performed on it by using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 5.3g (9.1mmol) of the target compound.
[0724] (Synthesis of Intermediate 85-5)
[0725] 5.3 g (9.1 mmol) of Intermediate 85-4, 3.7 g (9.1 mmol) of Intermediate A-6, SPhos (0.68 mmol), Pd 2 (dba) 3 7.1g (7.8mmol) of target compound was obtained by mixing 1.44mmol (0.46mmol) and sodium tert-butoxide (18.2mmol) in 90mL of toluene solvent and stirring for 4 hours after the temperature was raised to 110°C. After the reaction was completed, the solvent was removed therefrom under reduced pressure, and an extraction process was performed on it by using dichloromethane and distilled water. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 7.1g (7.8mmol) of target compound.
[0726] (Synthesis of Intermediate 85-6)
[0727] 7.1g (7.8mmol) of intermediate 85-5 was dissolved in 62mmol of triethyl orthoformate, and 8.8mmol of HCl was added dropwise thereto. The reaction mixture was heated to a temperature of 80°C and stirred for 20 hours. After the reaction was completed, the solvent was removed therefrom under reduced pressure, and an extraction process was performed on it by using dichloromethane and distilled water. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 6.7g (7.0mmol) of the target compound.
[0728] (Synthesis of Compound 85)
[0729] 6.7 g (7.0 mmol) of intermediate 85-6, 3.2 g (7.7 mmol) of potassium chloroplatinate and 3.0 g (28.2 mmol) of 2,6-lutidine were suspended in 140 mL of 1,2-dichlorobenzene. The reaction mixture was heated to a temperature of 120° C. and stirred for 18 hours. After the reaction was completed, the resulting product was cooled to room temperature, the solvent was removed therefrom, and the residue was separated by column chromatography to obtain 3.2 g (2.9 mmol) of the target compound.
[0730] Synthesis Example 8: Synthesis of Compound 88
[0731]
[0732] (Synthesis of Intermediate 88-1)
[0733] 5.1 g (18 mmol) of 7-methoxy-1,3-dipropyl-9H-carbazole, 5.8 g (27 mmol) of 2-bromo-4 (tert-butyl) pyridine, 8.3 g (36 mmol) of tripotassium phosphate, 0.66 g (3.6 mmol) of CuI and 0.4 g (3.6 mmol) of picolinic acid were added to a reaction vessel and suspended in 100 mL of dimethyl sulfoxide. The reaction mixture was heated to a temperature of 160 ° C and stirred for 24 hours. After the reaction was completed, the resulting product was cooled at room temperature, 100 ml of distilled water was added thereto, and an extraction process was performed on it by using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 4.6 g (11.1 mmol) of the target compound.
[0734] (Synthesis of Intermediate 88-2)
[0735] 4.6g (11.1mmol) of intermediate 88-1 was suspended in an excess of bromic acid solution. The reaction mixture was heated to 110°C and stirred for 24 hours. After the reaction was completed, the resulting product was cooled at room temperature and an appropriate amount of sodium bicarbonate was added thereto for neutralization. 100ml of distilled water was added thereto and an extraction process was performed on it by using ethyl acetate. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 3.6g (9.1mmol) of the target compound.
[0736] (Synthesis of Intermediate 88-3)
[0737] 3.6g (9.1mmol) of intermediate 88-2, 2.7g (13.7mmol) of 1-bromo-3-fluorobenzene and 4.2g (18.2mmol) of tripotassium phosphate are added to a reaction vessel and suspended in 90mL of dimethyl sulfoxide. The reaction mixture is heated to a temperature of 160°C and stirred for 12 hours. After the reaction is complete, the product therefrom is cooled at room temperature, 100ml of distilled water is added thereto, and an extraction process is performed on it by using ethyl acetate. The organic layer extracted therefrom is washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent has been removed is separated by column chromatography to obtain 4.1g (7.4mmol) of the target compound.
[0738] (Synthesis of Intermediate 88-4)
[0739] 4.1 g (7.4 mmol) of Intermediate 88-3, 2.6 g (7.4 mmol) of Intermediate A-7, SPhos (0.56 mmol), Pd 2 (dba) 3 5.3g (6.4mmol) of target compound was prepared by mixing 1.44mmol (0.37mmol) and sodium tert-butoxide (14.8mmol) in 75mL of toluene solvent and stirring for 4 hours after the temperature was raised to 110°C. After the reaction was completed, the solvent was removed therefrom under reduced pressure and an extraction process was performed using dichloromethane and distilled water. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 5.3g (6.4mmol) of the target compound.
[0740] (Synthesis of Intermediate 88-5)
[0741] 5.3g (6.4mmol) of intermediate 88-4 was dissolved in 54mmol of triethyl orthoformate, and 7.7mmol of HCl was added dropwise thereto. The reaction mixture was heated to a temperature of 80°C and stirred for 20 hours. After the reaction was completed, the solvent was removed therefrom under reduced pressure, and an extraction process was performed on it by using dichloromethane and distilled water. The organic layer extracted therefrom was washed with a saturated sodium chloride aqueous solution, and dried by using sodium sulfate. The residue from which the solvent was removed was separated by column chromatography to obtain 5.0g (5.8mmol) of the target compound.
[0742] (Synthesis of Compound 88)
[0743] 5.0 g (5.8 mmol) of intermediate 88-5, 2.6 g (6.2 mmol) of potassium chloroplatinate and 2.4 g (22.6 mmol) of 2,6-lutidine were suspended in 120 mL of 1,2-dichlorobenzene. The reaction mixture was heated to 120 ° C and stirred for 18 hours. After the reaction was completed, the resulting product was cooled to room temperature, the solvent was removed therefrom, and the residue was separated by column chromatography to obtain 2.2 g (2.1 mmol) of the target compound.
[0744] Example 1
[0745] 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, washed by ultrasonication using isopropyl alcohol and pure water for 5 minutes each, irradiated with ultraviolet rays and exposed to ozone for 30 minutes, and mounted on a vacuum deposition apparatus.
[0746] 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 .
[0747] Compound ETH2 (electron transport host), compound HTH29 (hole transport host) and compound 9 (dopant) are vacuum deposited on the hole transport layer to form a Here, the amount of compound 9 is 13 wt % per the total weight of the emission layer (100 wt %), and the weight ratio of compound ETH2 to compound HTH29 is adjusted to 3:7.
[0748] The compound ETH2 is vacuum deposited on the emission layer to form a A hole blocking layer with a thickness of , and compound ET46 and Liq were vacuum deposited on the hole blocking layer at a weight ratio of 4:6 to form a Yb is vacuum deposited on the electron transport layer to form an electron transport layer having a thickness of An electron injection layer having a thickness of 1000 mm was formed, and Mg was vacuum-deposited thereon to form an electron injection layer having a thickness of 1000 mm. A cathode with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.
[0749]
[0750] Examples 2 to 8 and Comparative Examples 1 to 4
[0751] An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 2 were each used as a dopant for forming an emission layer.
[0752] [Evaluation example]
[0753] Evaluation Example 1: Evaluation of properties of the organometallic compound represented by Formula 1
[0754] For compounds 9, 20, 31, 43, 65, 75, 85 and 88 and compounds A, B, C and D for comparison, the HOMO level (eV), LUMO level (eV), actual maximum emission wavelength (λ max (nm)) and triplet metal to ligand charge transfer states ( 3 The presence ratio (%) of MLCT) was measured, and the results are shown in Table 1.
[0755] [Table 1]
[0756]
[0757]
[0758]
[0759] Referring to the results in Table 1, it is confirmed that the compounds of the examples emit blue light in a short wavelength region compared with the compounds of the comparative examples. It is also confirmed that the compounds of the examples have higher 3 MLCT percentage, resulting in relatively high luminous efficiency.
[0760] Evaluation Example 2: Evaluation of Properties of Organic Light-Emitting Device
[0761] Table 2 shows the results of evaluating the organic light-emitting devices of the examples and comparative examples. For the organic light-emitting devices of the examples and comparative examples, the brightness at 1,000 cd / cm was measured by using Keithley MU 236 and luminance meter PR650, respectively. 2 The driving voltage (V) and color purity (CIE (x,y) ), luminous efficiency (cd / A), color conversion efficiency (cd / A / y), maximum emission wavelength (nm) and lifetime (T 95 , hr), and the results are shown in Table 2. Lifespan (T 95 , hr) is a measurement of the time (hr) taken for the brightness to reach 95% of the initial brightness.
[0762] [Table 2]
[0763]
[0764]
[0765] Referring to Table 2, it is confirmed that the organic light-emitting devices of Examples 1 to 8 have low driving voltage, comparable or high luminous efficiency, high color conversion efficiency, and long lifespan compared to the organic light-emitting devices of Comparative Examples 1 to 4.
[0766] According to an embodiment, the organic metal compound represented by Formula 1 may have excellent heat resistance stability and may be capable of emitting blue light with high luminous efficiency and high color purity. Then, the organic light-emitting device including the organic metal compound represented by Formula 1 may have low driving voltage, high luminous efficiency, high color conversion efficiency and long life. In this regard, an electronic device including an organic light-emitting device and an electronic device including an organic light-emitting device may have improved display quality.
[0767] 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 an embodiment 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 understand that various changes in form and detail may be made without departing from the spirit and scope of the present disclosure as set forth in the claims.
Claims
1. An organic 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 Formula 3A Wherein in Formula 1 and Formula 3A, M is platinum, palladium, copper, silver, gold, rhodium, iridium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, A1, A2 and A4 are each independently C5-C 60 Carbocyclic or C1-C 60 Heterocyclic group, Y1, Y2 and Y4 are each independently C or N, T1 to T4 each indicate a chemical bond, L1 to L4 are each independently a single bond, *-O-*', *-S-*', *-C(R5)(R6)-*', *-C(R5)=*', *=C(R5)-*', *-C(R5)=C(R6)-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R5)-*', *-N(R5)-*', *-P(R5)-*', *-Si(R5)(R6)-*' or *-Ge(R5)(R6)-*', a1 to a4 are each independently an integer selected from 0 to 5, R 31 To R 36 Each is independently a group represented by Formula 3A, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted 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 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C3-C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryl, 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 C1-C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a a substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), R 31 To R 36 At least one of them is independently a group represented by Formula 3A, R1, R2, R4, R5 and R6 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted with 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 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C3-C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryl, 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 C1-C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a a substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), n1, n2 and n4 are each independently an integer selected from 0 to 10, Two or more adjacent groups among R1, R2, R4, R5 and R6 are optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C5-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, Z 31 To Z 37 Each independently is: hydrogen, 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, -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 or C6-C 60 Arylthio: 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, -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 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), 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, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, 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, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, 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, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, 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 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted by alkoxy, phenyl, biphenyl or any combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl, and *Indicates the binding site with the neighboring atoms. 2 . The organic light-emitting device according to claim 1 , wherein the emission layer comprises the organic metal compound represented by Formula 1. 3 .
3. The organic light-emitting device according to claim 1, wherein The emission layer includes a host and a dopant, and The dopant includes the organic metal compound represented by Formula 1. 4 . The organic light-emitting device according to claim 1 , wherein the emission layer emits blue light having a maximum emission wavelength in a range of 410 nm to 490 nm. The organic light-emitting device according to claim 3 , wherein the emission layer further comprises a delayed fluorescent material. 6 . An electronic device comprising the organic light-emitting device according to claim 1 .
7. The electronic device according to claim 6, further comprising: Thin film transistors, where The thin film transistor includes a source electrode and a drain electrode, and The first electrode of the organic light-emitting device is electrically connected to at least one of the source electrode and the drain electrode.
8. An electronic device comprising the organic light-emitting device according to any one of claims 1 to 5, 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 retractable display, a laser printer, a phone, a mobile phone, a tablet personal computer, a tablet phone, 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 tiled together, a theater screen, a stadium screen, a light therapy device, a sign, a car sensor, a home sensor or a solar cell.
9. An organometallic compound represented by Formula 1: Formula 1 Formula 3A Wherein in Formula 1 and Formula 3A, M is platinum, palladium, copper, silver, gold, rhodium, iridium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, A1, A2 and A4 are each independently C5-C 60 Carbocyclic or C1-C 60 Heterocyclic group, Y1, Y2 and Y4 are each independently C or N, T1 to T4 each indicate a chemical bond, L1 to L4 are each independently a single bond, *-O-*', *-S-*', *-C(R5)(R6)-*', *-C(R5)=*', *=C(R5)-*', *-C(R5)=C(R6)-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R5)-*', *-N(R5)-*', *-P(R5)-*', *-Si(R5)(R6)-*' or *-Ge(R5)(R6)-*', a1 to a4 are each independently an integer selected from 0 to 5, R 31 To R 36 Each is independently a group represented by Formula 3A, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted 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 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C3-C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryl, 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 C1-C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a a substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), R 31 To R 36 At least one of them is independently a group represented by Formula 3A, R1, R2, R4, R5 and R6 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, unsubstituted or substituted with 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 10 Cycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkyl, unsubstituted or substituted with at least one R 10a Substituted C3-C 10 Cycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 10 Heterocycloalkenyl, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryl, 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 C1-C 60 Heteroaryl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroaryloxy, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heteroarylthio, unsubstituted or substituted with at least one R 10a A substituted monovalent non-aromatic fused polycyclic group, unsubstituted or replaced by at least one R 10a a substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), n1, n2 and n4 are each independently an integer selected from 0 to 10, Two or more adjacent groups among R1, R2, R4, R5 and R6 are optionally bonded to each other to form an unsubstituted or substituted group. 10a Substituted C5-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, Z 31 To Z 37 Each independently is: hydrogen, 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, -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 or C6-C 60 Arylthio: 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, -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 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), 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, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, 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, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, 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, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, 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 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 alkoxy; or each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted by alkoxy, phenyl, biphenyl or any combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl, and *Indicates the binding site with the neighboring atoms.
10. The organometallic compound according to claim 9, wherein R 31 To R 36 Two or more of are each independently a group represented by Formula 3A.
11. The organometallic compound according to claim 9, wherein R 33 is a group represented by Formula 3A, and R 31 , R 32 , R 34 , R 35 and R 36 One of them is a group represented by Formula 3A.
12. The organometallic compound according to claim 9, wherein Z 31 To Z 37 Each independently is: hydrogen or deuterium; or Unsubstituted or deuterated C1-C 20 alkyl.
13. The organometallic compound according to claim 9, wherein M is Pt, Pd, Cu, Ag or Au.
14. The organometallic compound according to claim 9, wherein Two of T1 to T4 are each coordination bonds, and The rest of T1 to T4 are each a covalent bond.
15. The organometallic compound according to claim 9, wherein L1 to L4 are each independently a single bond, *-O-*', *-S-*', *-N(R5)-*', *-C(R5)(R6)-*', *-Si(R5)(R6)-*' or *-B(R5)-*', R5 and R6 are each the same as defined in Formula 1, and * and *' each indicate a binding site with an adjacent atom. The organometallic compound according to claim 9 , wherein a4 is 0.
17. The organometallic compound according to claim 9, wherein in Formula 1, a4 is 0, and Depend on The moiety represented by is a moiety represented by Formula 1A or Formula 1B: Wherein in Formula 1A and Formula 1B, Y 12 C(R 12 ) or N, Y 13 C(R 13 ) or N, Y 14 C(R 14 ) or N, Y 15 C(R 15 ) or N, Y 16 C(R 16 ) or N, Y 17 C(R 17 ) or N, R 11 To R 17 are each independently the same as defined with reference to R1 in Formula 1, and * and *' each indicate a binding site with an adjacent atom.
18. The organometallic compound according to claim 17, wherein R 11 is a group represented by one of Formula 10A to Formula 19A: Wherein in Formula 10A to Formula 19A, Z 11 To Z 13 Each independently corresponds to R in Formula 1 10a The same definition, d3 is an integer selected from 0 to 3, d4 is an integer selected from 0 to 4, d5 is an integer selected from 0 to 5, and *Indicates the binding site with the neighboring atoms.
19. The organometallic compound according to claim 9, wherein the organometallic compound represented by Formula 1 is represented by Formula 1-1 or Formula 1-2: Formula 1-1 Formula 1-2 In Formula 1-1 and Formula 1-2, M, T1 to T4, L2, and R 31 To R 36 Each is the same as defined in Formula 1, Y 12 C(R 12 ) or N, Y 13 C(R 13 ) or N, Y 14 C(R 14 ) or N, Y 15 C(R 15 ) or N, Y 16 C(R 16 ) or N, Y 17 C(R 17 ) or N, Y 21 C(R 21 ) or N, Y 22 C(R 22 ) or N, Y 23 C(R 23 ) or N, Y 41 C(R 41 ) or N, Y 42 C(R 42 ) or N, Y 43 C(R 43 ) or N, Y 44 C(R 44 ) or N, R 11 To R 17 Each is independently the same as defined with reference to R1 in Formula 1, R 21 To R 23 are each independently the same as defined with reference to R2 in Formula 1, and R 41 To R 44 Each is independently the same as defined with reference to R4 in Formula 1.
20. The organometallic compound according to claim 9, wherein the organometallic compound represented by Formula 1 is one of Compound 1 to Compound 90:
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Device for charging a robotic load handling device
KR1020230145425A