Light-emitting device including organometallic compound, electronic device and electronic equipment including light-emitting device, and organometallic compound
By using an organometallic compound represented by Formula 1 in the light-emitting device, the problems of insufficient color purity and driving voltage are solved, and the energy transfer efficiency and lifetime characteristics are improved.
Patent Information
- Application Number
- CN202510774262.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-06-12
- Filing Date
- 2025-06-11
- Publication Date
- 2025-12-12
AI Technical Summary
Existing light-emitting devices have shortcomings in terms of color purity and driving voltage, and their energy transfer efficiency needs to be improved.
Organometallic compounds represented by Formula 1, including combinations of metals such as platinum, iridium, palladium, cobalt, gold, nickel or silver with carbocyclic or heterocyclic groups, are used in the interlayer and emission layer of light-emitting devices to enhance exciton recombination efficiency and improve energy transfer.
It improves the color purity and driving voltage of the light-emitting device, while also improving energy transfer efficiency and lifespan characteristics.
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Figure CN121108196A_ABST
Abstract
Description
[0001] Cross-references to related applications
[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0076607, filed on June 12, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0003] The embodiments relate to light-emitting devices including organometallic compounds, electronic devices and electronic equipment including light-emitting devices, and organometallic compounds. Background Technology
[0004] The light-emitting device is a self-emitting device, which has a wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage and response speed.
[0005] In a light-emitting device, a first electrode is disposed on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode are sequentially disposed on the first electrode. Holes supplied from the first electrode move toward the emitter layer through the hole transport region, and electrons supplied from the second electrode move toward the emitter layer through the electron transport region. Charge carriers (such as holes and electrons) recombine in the emitter layer to generate excitons. These excitons transition from an excited state to the ground state, thereby generating light.
[0006] It should be understood that this background section is intended in part to provide useful background for understanding the art. However, this background section may also include ideas, concepts, or knowledge that were not part of what a person skilled in the art knew or understood prior to the corresponding valid application date of the subject matter disclosed herein. Summary of the Invention
[0007] The embodiments include: a light-emitting device including an organometallic compound, an electronic device and electronic equipment including a light-emitting device, and an organometallic compound.
[0008] Other aspects will be set forth in part in the description which follows and will be apparent in part from the description, or may be learned by practice of embodiments of this disclosure.
[0009] According to an embodiment, the light-emitting device may include:
[0010] First electrode,
[0011] The second electrode facing the first electrode.
[0012] An interlayer comprising an emission layer between the first and second electrodes, and
[0013] Organometallic compounds represented by Formula 1:
[0014] [Formula 1]
[0015]
[0016] In Equation 1,
[0017] M can be platinum (Pt), iridium (Ir), palladium (Pd), cobalt (Co), gold (Au), nickel (Ni), silver (Ag), or copper (Cu).
[0018] CY1 to CY5 can each be independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group,
[0019] X1 to X4 can each be C or N independently.
[0020] T1 and T2 can each be independently N(R6), C(R6)(R7), Si(R6)(R7), S, or O.
[0021] L1 and L2 can each independently be a single bond, *-N(R8)-*', *-B(R8)-*', *-P(R8)-*', *-C(R8)(R9)-*', *-Si(R8)(R9)-*', *-Ge(R8)(R9)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', or *-C(=S)-*'.
[0022] a1 to a5 can each be an integer selected from 0 to 10 independently.
[0023] R1 to R9 can each be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic group, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10aReplacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C7-C 60 Aryl, unsubstituted or with at least one R 10a Replacement C2-C 60 Heteroaryl groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), R 10a Possible forms:
[0024] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;
[0025] Each of the following C1-C that is not substituted or is substituted: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 heteroaryl, -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;
[0026] Each of the following C3-Cs that are not substituted or are substituted by: 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclyl, C1-C 60 heterocyclyl, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), or any combination thereof; or
[0027] -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
[0028] Q1to Q3, Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 may each independently be hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl, cyano; nitro; C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, or any combination thereof substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclyl, or C1-C 60 heterocyclyl; C7-C 60 aralkyl; or C2-C 60heteroarylalkyl.
[0029] In embodiments, the first electrode can be an anode; the second electrode can be a cathode; the interlayer can further include a hole transport zone between the first electrode and the emissive layer and an electron transport zone between the emissive layer and the second electrode; the hole transport zone can include a hole injection layer, a hole transport layer, an emissive auxiliary layer, an electron blocking layer, or any combination thereof; and the electron transport zone can include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
[0030] In embodiments, the interlayer can include an organometallic compound.
[0031] In embodiments, the emissive layer can include an organometallic compound.
[0032] In embodiments, the emissive layer can include a host and a dopant, and the dopant can include an organometallic compound.
[0033] According to embodiments, an electronic device can include a light emitting apparatus.
[0034] In embodiments, the electronic device can further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
[0035] According to embodiments, an electronic equipment can include a light emitting apparatus.
[0036] In embodiments, the electronic equipment 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 full transparent display, a partial transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet computer, a phablet computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall having multiple displays tiled together, a theater screen, a stadium screen, a light therapy device, or a signboard.
[0037] According to embodiments, an organometallic compound can be represented by Formula 1, which is explained herein.
[0038] In embodiments, Formula 1 can include deuterium, a cyano group, a carbazolyl group, a tert-butyl group, or any combination thereof.
[0039] In embodiments, in Formula 1, a cyclometallating group including M, X2, T1, T2, and X3may have a ring structure of 9 or more members.
[0040] In embodiments, CY1to CY5may each independently be phenyl, naphthyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, tetrahydronaphthyl, indolyl, benzoindolyl, naphthoindolyl, isoindolyl, benzoisoindolyl, naphthoisoindolyl, benzothiophyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiophyl, dibenzothiophenyl, dibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzoisothiazolyl, indazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinoxalyl, benzoquinoxalyl, quinazolyl, benzoquinazolyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthidinyl, imidazopyridyl, imidazopyrimidyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafuorenyl, azadibenzothiophyl, azadibenzothiophenyl, or azadibenzofuranyl.
[0041] In embodiments, in Formula 1, the moiety represented by may be a moiety represented by Formula 2, which is explained below.
[0042] In embodiments, R 12 may be a group represented by Formula 6, which is explained below.
[0043] In embodiments, in Formula 1, the moiety represented by may be a moiety represented by Formula 3, which is explained below.
[0044] In embodiments, in Formula 1, the moiety represented by may be a moiety represented by Formula 4, which is explained below.
[0045] In embodiments, in Formula 1, the moiety represented by may be a moiety represented by Formula 5, which is explained below.
[0046] In embodiments, in Formula 1, the moiety represented by may be a moiety represented by one of Formula 6-1 to Formula 6-6, which is explained below.
[0047] In embodiments, the organometallic compound can be one of Compound BD01 to Compound BD112, which are explained below.
[0048] It should be understood that the above embodiments describe only the general and explanatory sense and not for limiting purposes, and the present disclosure is not limited to the above-described embodiments. BRIEF DESCRIPTION OF DRAWINGS
[0049] The accompanying drawings are included to provide a further understanding of embodiments and are incorporated in and constitute a part of this specification. The drawings illustrate the principles of the disclosure and, although not to be limited thereto, serve to explain the principles and operations of embodiments of the disclosure. The above and other aspects and features of the disclosure will become more apparent when the embodiments thereof are described in detail in conjunction with the accompanying drawings, in which:
[0050] Figure 1 is a schematic cross-sectional view of a light emitting device according to an embodiment;
[0051] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment;
[0052] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment;
[0053] Figure 4 is a schematic perspective view of an electronic equipment according to an embodiment;
[0054] Figure 5 is a schematic perspective view of an exterior of a vehicle of an electronic equipment according to an embodiment; and
[0055] Figures 6A to 6C are each a schematic view of an interior of a vehicle according to an embodiment. DETAILED DESCRIPTION
[0056] The disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. The disclosure may, however, be embodied in different forms, and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the disclosure to those skilled in the art.
[0057] In the drawings, the size, proportions, and dimensions (e.g., thicknesses) of elements can be exaggerated for ease of description and for clarity. The same reference numbers and / or characters indicate the same elements throughout the figures.
[0058] In the description, it will be understood that when an element (or a region, layer, part, etc.) is referred to as being "on" another element (or a region, layer, part, etc.), it can be directly on the other element (or region, layer, part, etc.) or intervening elements (or regions, layers, parts, etc.) can be present. In the same manner, when an element (or a region, layer, part, etc.) is referred to as being "connected", or "coupled", to another element (or a region, layer, part, etc.), it can be directly connected or coupled to the other element (or region, layer, part, etc.) or intervening elements (or regions, layers, parts, etc.) can be present. In the same manner, when an element (or a region, layer, part, etc.) is referred to as "covering" another element (or a region, layer, part, etc.), it can directly cover the other element (or region, layer, part, etc.) or one or more intervening elements (or regions, layers, parts, etc.) can be present.
[0059] In the description, when an element is "directly on" another element, "directly connected to" another element, or "directly coupled to" another element, there is no intermediary element. For example, "directly on" can mean that two layers or two elements are disposed without any other element (such as an adhesive element) between them.
[0060] As used herein, expressions used in the singular, such as “a”, “an”, and “the”, are intended to also include the plural form unless the context clearly indicates otherwise.
[0061] As used herein, the term “and / or” includes any and all combinations of one or more related enumerated 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 or separating sense and can be understood as equivalent to “and / or”.
[0062] In the specification and claims, the term "at least one of..." is intended to include the meaning of "at least one selected from the group consisting of..." for the purposes of its meaning and interpretation. For example, "at least one of A, B, and C" can 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 any individual element in the list.
[0063] It will be understood that although the terms first, second, etc., may be used herein to describe various elements, these elements should not be limited by these terms. These terms are used only to distinguish one element from another. Therefore, without departing from the teachings of this disclosure, a first element may be referred to as a second element. Similarly, without departing from the scope of this disclosure, a second element may be referred to as a first element.
[0064] For ease of description, spatial relative terms such as “below,” “under,” “down,” “above,” or “above” may be used herein to describe the relationship between one element or component and another, as illustrated in the accompanying drawings. It will be understood that spatial relative terms are intended to encompass different orientations of the apparatus in use or operation, other than those depicted in the drawings. For example, in the case of flipping the apparatus illustrated in the drawings, an apparatus located “below” or “under” another apparatus may be placed “above” the other apparatus. Accordingly, the interpretative term “below” may include both a lower position and an upper position. The apparatus may also be oriented in other directions, and therefore the spatial relative terms may be interpreted differently depending on the orientation.
[0065] The terms "about" or "approximately," as used herein, include recited values and mean within an acceptable range of deviation of the recited value as determined by one of ordinary skill in the art considering the measurement in question and the error in half-value associated with the measurement of the recited quantity (e.g., limitations of the measurement system). For example, "about" can mean within one or more standard deviations of the recited value, or within ±20%, ±10%, or ±5% of the recited value.
[0066] It is to be understood that the terms "comprises", "comprising", "includes", "including", "has", "having", "contains" and "containing", or any other variation thereof, are intended to indicate the presence of the stated features, integers, steps, operations, elements, components, or combinations thereof, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.
[0067] Unless otherwise defined or implied herein, all terms used are intended to have the same meaning as commonly understood by one of ordinary skill in the art in the field of the disclosure. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and will not be interpreted in an idealized or overly formal sense unless expressly so defined in the specification.
[0068] According to an embodiment, the light-emitting device can include: a first electrode; a second electrode facing the first electrode; a sandwich layer between the first electrode and the second electrode and including an emission layer; and an organometallic compound represented by Formula 1:
[0069] [Formula 1]
[0070]
[0071] In Formula 1,
[0072] M can be platinum (Pt), iridium (Ir), palladium (Pd), cobalt (Co), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
[0073] CY1 to CY5 can each independently be C3-C 60 carbocyclyl or C1-C 60 heterocyclyl,
[0074] X1 to X4 can each independently be C or N,
[0075] T1 and T2 can each be independently N(R6), C(R6)(R7), Si(R6)(R7), S, or O.
[0076] L1 and L2 can each independently be a single bond, *-N(R8)-*', *-B(R8)-*', *-P(R8)-*', *-C(R8)(R9)-*', *-Si(R8)(R9)-*', *-Ge(R8)(R9)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', or *-C(=S)-*'.
[0077] a1 to a5 can each be an integer selected from 0 to 10 independently.
[0078] R1 to R9 can each be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic group, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C7-C 60 Aryl, unsubstituted or with at least one R 10a Replacement C2-C 60 Heteroaryl groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), R 10a Possible forms:
[0079] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;
[0080] Each of the following C1-C that is not substituted or is substituted: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 heteroaryl, -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;
[0081] Each of the following C3-Cs that are not substituted or are substituted by: 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 heteroaryl, -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
[0082] -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
[0083] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; each unsubstituted or replaced by deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aryl alkyl group; or C2-C 60 Heteroalkyl groups.
[0084] According to an embodiment, Formula 1 may include deuterium, cyano, carbazole, tert-butyl, or any combination thereof.
[0085] According to an embodiment, in Formula 1, the cyclic metallizing groups including M, X2, T1, T2 and X3 may have a 9-membered or more-membered ring structure.
[0086] According to the implementation method, M can be Pt.
[0087] According to the embodiments, CY1 to CY5 can each independently be cyclopentadienyl, adamantyl, norbornel, phenyl, pentanenyl, naphthyl, azuleyl, indaryl, acenaphthel, phenanthreneyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenantyl, perylene, penfenyl, heptanenyl, tetraphenyl, fraxyl, hexaphenyl, pentaphenyl, rubiginyl, keratyl, ovoleyl, indene, fluorenyl, spirodifluorenyl, benzofluorenyl, indene Phenanthryl, indo[anthracene]yl, tetrahydronaphthyl, pyrroleyl, thiopheneyl, furanyl, indoleyl, benzo[indoleyl], naphtho[indoleyl], isoindoleyl, benzo[isoindoleyl], naphtho[isoindoleyl], benzo[thiophene], benzo[furanyl], carbazoleyl, dibenzo[thiophene], dibenzo[furanyl], indo[carbazoleyl], benzo[furanyl], benzo[thiophene], benzo[thiophene], benzo[indo[carbazoleyl], benzo[indo[carbazoleyl] Benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiol, benzonaphthothiol, benzofuran-dibenzofuranyl, benzofuran-dibenzothiol, benzothiophene-dibenzothiol, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benzoisooxazolyl, benzothiazolyl, benzoisothiazolyl, indazole, pyridyl Pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cyclolinyl, phthalazinyl, naphthinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazoyl, azafluorenyl, azadibenzothiopheneyl, azadibenzothiopheneyl, or azadibenzofuranyl.
[0088] According to the embodiments, CY1 to CY5 can each independently be phenyl, naphthyl, phenanthryl, anthraceneyl, fluoranthyl, triphenylene, pyrene, tetrahydronaphthyl, indoleyl, benzo[a]indoleyl, naph[a]indoleyl, isoindoleyl, benzo[a]isoindoleyl, naph[a]isoindoleyl, benzo[a]thiophenyl, benzo[a]furanyl, carbazoleyl, dibenzo[a]thiophenyl, dibenzo[a]thiophenyl, dibenzo[a]furanyl, pyrazolyl, imidazoleyl, triazoleyl, oxazolyl, isoxazolyl, oxadiazoleyl, thiazolyl, isothiazolyl, thiazolyl, benzo[a]pyrazolyl, benzo[a]imidazolyl, benzo[a]oxazolyl Azolyl, benzoisoxazolyl, benzothiazolyl, benzoisothiazolyl, indazole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinel, cinolinyl, phthalazinyl, naphridinyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiophene, azadibenzothiophene, or azadibenzofuranyl.
[0089] According to embodiments, in Formula 1, the moiety represented by may be a moiety represented by Formula 2:
[0090] [Formula 2]
[0091]
[0092] In Formula 2,
[0093] X1may be the same as described herein,
[0094] R 11 and R 12 may each independently be the same as defined herein with reference to R1, CY 11 may be the same as defined herein with reference to CY1, a11may be an integer selected from 0 to 10,
[0095] * indicates a binding site to M, and
[0096] * indicates a binding site to L1.
[0097] According to embodiments, in Formula 2, R 12 may be a group represented by Formula 6: [Formula 6]
[0098]
[0099] In Formula 6,
[0100] R 61 to R 64 may each independently be the same as defined herein with reference to R1, a61and a62may each independently be an integer selected from 1 to 5, a63may be an integer selected from 1 to 3,
[0101] a64may be an integer selected from 1 to 4,
[0102] b1may be an integer selected from 0 to 10, and
[0103] * indicates a binding site to an adjacent atom.
[0104] According to embodiments, in Formula 1, R1may be a group represented by Formula 6.
[0105] According to embodiments, in Formula 1, the moiety represented by may be a moiety represented by Formula 3:
[0106] [Formula 3]
[0107]
[0108] In Formula 3,
[0109] X2may be the same as described herein,
[0110] Y 21 and Y 22 may each independently be C or N,
[0111] Y 23 may be C(R 23 ) or N,
[0112] Y 24 may be C(R 24 ) or N,
[0113] Y 25 may be C(R 25 ) or N,
[0114] R 23 to R 25 may each independently be the same as defined herein with reference to R2,
[0115] * indicates a binding site to L1,
[0116] *’ indicates a binding site to M, and
[0117] *” indicates a binding site to T1.
[0118] According to embodiments, in Formula 1, the moiety represented by may be a moiety represented by Formula 4:
[0119] [Formula 4]
[0120]
[0121] In Formula 4,
[0122] X3may be the same as described herein,
[0123] CY 31 and CY 32 may each independently be the same as defined herein with reference to CY3,
[0124] T3may be a single bond, N(R 33 ), C(R 33 )(R 34 ), Si(R 33 )(R 34 ), S, or O,
[0125] R 31 to R 34 may each independently be the same as defined herein with reference to R3,
[0126] a31 and a32 can each independently be an integer selected from 0 to 10,
[0127] * indicates a binding site with L2,
[0128] * indicates a binding site with M, and
[0129] * indicates a binding site with T2.
[0130] According to embodiments, in Formula 1, the moiety represented by may be a moiety represented by Formula 5:
[0131] [Formula 5]
[0132]
[0133] In Formula 5,
[0134] X4may be the same as described herein,
[0135] Y 41 may be C or N,
[0136] Y 42 may be C(R 42 ) or N,
[0137] Y 43 may be C(R 43 ) or N,
[0138] Y 44 may be C(R 44 ) or N,
[0139] Y 45 may be C(R 45 ) or N,
[0140] R 42 to R 45 may each independently be the same as defined herein with reference to R4,
[0141] * indicates a binding site with M, and
[0142] * indicates a binding site with L2.
[0143] According to embodiments, in Formula 1, the moiety represented by may be a moiety represented by one of Formulae 6-1 to 6-6:
[0144]
[0145]
[0146] In Formulae 6-1 to 6-6,
[0147] Y 51 may be C(R 51 ) or N,
[0148] Y 52 may be C(R 52 ) or N,
[0149] Y 53 may be C(R 53 ) or N,
[0150] Y 54 may be C(R 54 ) or N,
[0151] Y 55 may be C(R 55 ) or N,
[0152] Y 56 may be C(R 56 ) or N,
[0153] Y 57 may be C(R 57 ) or N,
[0154] Y 58 may be C(R 58 ) or N,
[0155] R 51 to R 59 may each independently be the same as defined herein with reference to R5,
[0156] a59may be an integer selected from 0 to 8, and
[0157] * and *' indicate the binding site to T1or T2, respectively.
[0158] According to embodiments, the bond between X1and M and the bond between X4and M can each be a coordinate bond, and the bond between X2and M and the bond between X3and M can each be a covalent bond.
[0159] According to embodiments, X1to X3may each be C, and X4may be N.
[0160] According to embodiments, X1may be a carbon atom of a carbene moiety.
[0161] According to embodiments, T1and T2may each independently be S or O.
[0162] According to embodiments, L1and L2may each independently be a single bond, *-N(R8)-*', *-B(R8)-*', *-C(R8)(R9)-*', *-Si(R8)(R9)-*', *-S-*', or *-O-*'.
[0163] According to embodiments, R1to R9may each independently be hydrogen, deuterium, cyano, t-butyl, or any combination thereof.
[0164] According to embodiments, R1to R9may each independently be:
[0165] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 alkyl;
[0166] substituted with at least one of deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, and pyrimidyl; 20 alkyl;
[0167] phenyl, biphenyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or azacarbazolyl, each unsubstituted or substituted with at least one of deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 alkyl, phenyl, biphenyl, C1-C 10 alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzo phenanthryl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalyl, quinazolyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, biscarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), and -B(Q 31 )(Q 32 ); or
[0168] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), or -B(Q1)(Q2), and
[0169] Q1to Q3and Q 31 to Q 33 may each independently be:
[0170] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or
[0171] each unsubstituted or substituted with at least one of deuterium, C1-C6alkyl, C1-C6haloalkyl, C1-C6hydroxyalkyl, C1-C6cyanoalkyl, C1-C6aminoalkyl, C1-C6dialkylaminylalkyl, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6hydroxyalkylcarbonyl, C1-C6cyanoalkylcarbonyl, C1-C6aminoalkylcarbonyl, C1-C6dialkylaminylalkylcarbonyl, -F, -Cl, -Br, -I, -OH, -CN, or -NO2; 10 alkyl, phenyl, and biphenyl.
[0172] According to embodiments, R1to R9may each independently be:
[0173] hydrogen, deuterium, -F, -Cl, -Br, -I, or cyano;
[0174] each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -OH, -CN, or -NO2;
[0175] each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -OH, -CN, -NO2, C1-C6alkyl, C1-C6haloalkyl, C1-C6hydroxyalkyl, C1-C6cyanoalkyl, C1-C6aminoalkyl, C1-C6dialkylaminylalkyl, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6hydroxyalkylcarbonyl, C1-C6cyanoalkylcarbonyl, C1-C6aminoalkylcarbonyl, C1-C6dialkylaminylalkylcarbonyl, phenyl, biphenyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or azacarbazolyl; or
[0176] -Si(Q1)(Q2)(Q3), and
[0177] Q1to Q3may each be the same as defined herein.
[0178] According to embodiments, the organometallic compound represented by Formula 1 can be any one of compounds BD01 to compounds BD112:
[0179]
[0180]
[0181]
[0182]
[0183]
[0184]
[0185] In the compound BD01 to the compound BD112, M is Pt.
[0186] The organometallic compound represented by Formula 1 can include a moiety consisting of T1-CY5-T2 in Formula 1, which increases a difference (ΔE) between a highest occupied molecular orbital (HOMO) energy level and a lowest unoccupied molecular orbital (LUMO) energy level, thereby more effectively shortening a maximum emission wavelength.
[0187] In an embodiment, the organometallic compound represented by Formula 1 can improve color purity and driving voltage of a light-emitting device. In a light-emitting device including the organometallic compound represented by Formula 1, energy can be easily transferred within the light-emitting device, thereby improving a lifespan characteristic.
[0188] A person of ordinary skill in the art can easily understand a method of synthesizing the organometallic compound represented by Formula 1 by referring to the synthesis examples and / or embodiments described herein.
[0189] At least one organometallic compound represented by Formula 1 can be used in a light-emitting device (e.g., an organic light-emitting device). Accordingly, according to an embodiment, a light-emitting device can include a first electrode; a second electrode facing the first electrode; a sandwich layer between the first electrode and the second electrode and including an emission layer; and an organometallic compound represented by Formula 1.
[0190] According to an embodiment,
[0191] The first electrode of the light-emitting device can be an anode,
[0192] The second electrode of the light-emitting device can be a cathode,
[0193] The sandwich layer can further include a hole transport zone between the first electrode and the emission layer and an electron transport zone between the emission layer and the second electrode,
[0194] The hole transport zone can include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and
[0195] The electron transport zone can include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
[0196] According to an embodiment, the interlayer can include an organometallic compound represented by Formula 1.
[0197] According to an embodiment, the emission layer can include an organometallic compound represented by Formula 1.
[0198] According to an embodiment, the emission layer can include a host and a dopant, and the dopant can include an organometallic compound represented by Formula 1.
[0199] According to an embodiment, the emission layer can emit blue light.
[0200] According to an embodiment, the dopant can be a phosphorescent dopant.
[0201] According to an embodiment, the emission layer can further include a first host and a second host, wherein the first host can be a hole transport compound including at least one electron donating group, and the second host can be an electron transport compound including at least one electron withdrawing group.
[0202] According to an embodiment, the emission layer can further include a third compound, and the third compound can be a metal-containing compound.
[0203] According to an embodiment, the third compound can be used as a sensitizer. For example, the third compound can be used as a phosphorescent sensitizer.
[0204] According to an embodiment, the third compound can not emit light.
[0205] In an embodiment, the emission layer can further include at least one of an auxiliary dopant and a sensitizer.
[0206] According to an embodiment, the auxiliary dopant and the sensitizer can each independently be an organometallic compound including platinum and a tetradentate ligand bonded to the platinum, wherein the tetradentate ligand can include a carbene moiety chemically bonded to the platinum. In an embodiment, the auxiliary dopant and / or the sensitizer can include the third compound.
[0207] According to an embodiment, the first host and the second host can be used as an exciton complex host.
[0208] In the specification, the term "electron donating group" can be any group having an electron donating ability, and for example, can be a π-electron rich C3-C 60 cyclic group or an amine group, but embodiments are not limited thereto. The electron donating group can be a cyclic group other than a π-electron deficient nitrogen-containing C1-C 60 cyclic group.
[0209] The term "electron-withdrawing group" can be any group having an electron-withdrawing ability, and for example, can be -F, -CFH2, -CF2H, -CF3, -CN, -NO2, a π-electron deficient nitrogen-containing C1-C 60 Embodiments are not limited thereto, however.
[0210] With regard to a light-emitting pathway in the light-emitting device according to embodiments, the first host and the second host can form an exciplex (a first process), energy can be transferred from the exciplex to the third compound (a second process), and energy can be transferred from the third compound to the organometallic compound (a third process).
[0211] According to embodiments, the amount of the third compound can be in the range of about 0 parts by weight to about 50 parts by weight, based on total 100 parts by weight of the emission layer.
[0212] According to embodiments, the first host can include at least one carbazole moiety, and the second host can include at least one azine moiety.
[0213] In embodiments, the first host can be represented by Formula 301-1A or Formula 301-2A:
[0214] [Formula 301-1A]
[0215]
[0216] [Formula 301-2A]
[0217]
[0218] In Formula 301-1A and Formula 301-2A,
[0219] Ring A 301 to Ring A 304 may each independently be unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclyl or unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclyl,
[0220] X 301 may be O, S, N[(L 304 ) xb4 -R 304a ], C(R 304a )(R 304b ) or Si(R 304a )(R 304b ),
[0221] X 302 may be a single bond, O, S, N[(L305 ) xb5 -R 305a ]、C(R 305a (R) 305b ) or Si(R 305a (R) 305b ),
[0222] X 303 Can be a single bond, O, S, N[(L 306 ) xb6 -R 306a ]、C(R 306a (R) 306b ) or Si(R 306a (R) 306b ),
[0223] xb22 and xb23 can each be an integer selected from 0 to 10 independently.
[0224] L 301 To L 307 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0225] xb1 to xb7 can each be an integer selected from 0 to 5 independently.
[0226] R 301 To R 303 R 304a To R 306a R 304b To R 306b and R 311 To R 314 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60heterocyclyl, unsubstituted or substituted by at least one R 10a substituted C7-C 60 aralkyl, -C(Q1)(Q2)(Q3), -Si(Q 301 )(Q 302 )(Q 303 ), -N(Q 301 )(Q 302 ), -B(Q 301 )(Q 302 ), -C(=O)(Q 301 ), -S(=O)2(Q 301 ), or -P(=O)(Q 301 )(Q 302 ), and
[0227] Q 301 to Q 303 may each independently be the same as described with reference to Q1.
[0228] In an embodiment, the first host can be one of compounds HTH1 to HTH56, but embodiments are not limited thereto:
[0229]
[0230]
[0231]
[0232] In an embodiment, the second host can be represented by formula 302:
[0233] [Formula 302]
[0234]
[0235] In formula 302,
[0236] X 321 may be C(R 321 ) or N,
[0237] X 322 may be C(R 322 ) or N,
[0238] X 323 may be C(R 323 ) or N,
[0239] X 321 to X 323 may each be N,
[0240] L 324 to L 326Each can be independently a single bond, unsubstituted, or bonded by at least one R. 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, *-C(Q) 321 (Q) 322 )-*'、*-Si(Q 321 (Q) 322 )-*'、*-B(Q 321 )-*' or *-N(Q 321 )-*',
[0241] n324 to n326 can each be an integer selected from 1 to 5 independently.
[0242] R 321 To R 326 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic group, unsubstituted or with at least one R 10a Replacement C7-C 60 Aryl groups, -C(Q1)(Q2)(Q3), -Si(Q 323 (Q) 324 (Q) 325 -N(Q) 323 (Q) 324 -B(Q) 323 (Q) 324 -C(=O)(Q) 323 -S(=O)2(Q) 323 ) or -P(=O)(Q 323 (Q) 324 ),
[0243] Q 321 To Q 325 and R 321 To R326 Two or more adjacent groups may optionally be bonded to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C2-C 30 Heterocyclic group,
[0244] * and *' each indicate the binding site with the adjacent atom.
[0245] R 10a It may be the same as described in this article, and
[0246] Q 321 To Q 325 Each can be independently identical to the description in reference Q1.
[0247] In this embodiment, the second body may be one of compounds ETH1 to ETH86, but the embodiment is not limited to this:
[0248]
[0249]
[0250]
[0251]
[0252] In an embodiment, the third compound may be represented by formula 401A: [Formula 401A]
[0253] M 401 (L 401 ) xc1 (L 402 ) xc2
[0254]
[0255]
[0256] In Equations 401A and 402A to 402D,
[0257] M 401 These can be transition metals in the first row, the second row, or the third row of the periodic table.
[0258] L 401 It can be a ligand represented by one of formulas 402A to 402D.
[0259] L 402It can be a monodentate, bidentate, or tripentate ligand.
[0260] xc1 can be 1 or 2.
[0261] xc2 can be an integer selected from 0 to 4.
[0262] A 401 To A 404 Each can be independently classified as C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group,
[0263] T 401 To T 404 Each can independently be a single bond, double bond, *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', or *-C(R)-*'. 405 (R) 406 )-*'、*-C(R 405 )=C(R 406 )-*'、*-C(R 405 )=*'、*-Si(R 405 (R) 406 )-*'、*-B(R 405 )-*'、*-N(R 405 )-*' or *-P(R 405 )-*',
[0264] k401 to k404 can each be independently 1, 2, or 3.
[0265] Y 401 To Y 404 Each can be an independent single bond (e.g., a covalent or coordinate bond), *-O-*', *-S-*', *-C(R)', etc. 407 (R) 408 )-*'、*-Si(R 407 (R) 408 )-*'、*-B(R 407 )-*'、*-N(R 407 )-*' or *-P(R 407 )-*',
[0266] In Equations 402A to 402D, *1, *2, *3, and *4 each indicate the same as M in Equation 401A. 401 binding sites,
[0267] R 401 To R 408 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic group, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C7-C 60 Aryl groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0268] R 401 To R 408 They may optionally bond to each other to form unsubstituted or by at least one R 10a Replacement C5-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0269] b401 to b404 can each be an integer selected from 0 to 10 independently.
[0270] * and *' each indicate the binding site with the adjacent atom, and
[0271] Q1 to Q3 and R 10a Each can be the same as described in this article.
[0272] According to an embodiment, the compound represented by formula 401A may be a carbene complex.
[0273] In the specification, the term "carbaene complex" may refer to a complex comprising a metal and a ligand bonded to the metal, wherein at least one bond between the metal and the ligand is a bond between the carbon atoms of the metal and the carbaene moiety.
[0274] In embodiments, the sensitizing agent can include a compound represented by Formula 401A.
[0275] In embodiments, the third compound can include one of compounds PD1 through PD41, but embodiments are not limited thereto:
[0276]
[0277]
[0278]
[0279] In embodiments, R 301 to R 303 , R 304a to R 306a , R 304b to R 306b , and R 311 to R 314 , R 321 to R 326 , and R 401 to R 408 in Formula 301-1A and Formula 301-2A can each independently be:
[0280] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 alkyl, or C1-C 20 alkoxy;
[0281] C1-C 20 alkyl or C1-C 20 alkoxy each unsubstituted or substituted with hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, or any combination thereof;
[0282] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10alkyl, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 alkyl, C1-C 31 alkyl, C1-C 32 alkyl, C1-C 33 alkyl, C1-C 31 alkyl, C1-C 32 alkyl, C1-C 31 alkyl, C1-C 31 alkyl, C1-C 31 alkyl, C1-C 32) or any combination thereof; or
[0283] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=0)(Q1), -S(=0)2(Q1), or -P(=0)(Q1)(Q2), and each of Q1to Q3is the same as described herein:
[0284] Q1to Q3and Q 31 to Q 33 may each be the same as described herein.
[0285] In embodiments, R 301 to R 303 , R 304a to R 306a , R 304b to R 306b , and R 311 to R 314 , R 321 to R 326 , and R 401 to R 408 may each independently be:
[0286] hydrogen, deuterium, -F, -CI, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy;
[0287] a group represented by one of Formulae 9-1 to 9-61 or a group represented by one of Formulae 10-1 to 10-348; or
[0288] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=0)(Q1), -S(=0)2(Q1), or -P(=0)(Q1)(Q2), wherein Q1to Q3are each the same as described herein:
[0289]
[0290]
[0291]
[0292]
[0293]
[0294]
[0295]
[0296]
[0297]
[0298] In Formulae 9-1 to 9-61 and 10-1 to 10-348, * indicates a bonding site with an adjacent atom, Ph represents a phenyl group, TMS represents a trimethylsilyl group, and D represents a deuterium atom, and
[0299] Q1 to Q3 can each be the same as described herein.
[0300] According to an embodiment, the electron transport zone of the light-emitting device can include a hole blocking layer, and the hole blocking layer can include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. For example, the hole blocking layer can contact (e.g., directly contact) the emission layer.
[0301] According to an embodiment, the light-emitting device can include a capping layer outside of the first electrode and / or the second electrode.
[0302] In an embodiment, the light-emitting device can further include at least one of a first capping layer outside of the first electrode and a second capping layer outside of the second electrode, and the organometallic compound represented by Formula 1 can be included in at least one of the first capping layer and the second capping layer. The first capping layer and / or the second capping layer can be the same as described herein.
[0303] According to an embodiment, the light-emitting device can include:
[0304] a first capping layer outside of the first electrode and including the organometallic compound represented by Formula 1;
[0305] a second capping layer outside of the second electrode and including the organometallic compound represented by Formula 1; or
[0306] the first capping layer and the second capping layer.
[0307] In the specification, the term "(interlayer and / or capping layer) includes an organometallic compound represented by Formula 1" can be understood as "(interlayer and / or capping layer) can include one organometallic compound represented by Formula 1 or two or more different organometallic compounds each independently represented by Formula 1".
[0308] In embodiments, the interlayer and / or the capping layer can include only compound BD01 as the organometallic compound. For example, compound BD01 can be present in an emissive layer of the light-emitting device. In embodiments, the interlayer can include compound BD01 and compound BD02 as the organometallic compounds. For example, compound BD01 and compound BD-02 can be present in the same layer (e.g., both compound BD01 and compound BD02 can be present in the emissive layer), or can be present in different layers (e.g., compound BD01 can be present in the emissive layer, and compound BD02 can be present in the electron transport region).
[0309] In the description, the term “interlayer” can be a single layer and / or multiple layers between the first electrode and the second electrode of the light-emitting device.
[0310] According to embodiments, an electronic device can include a light-emitting device. The electronic device can further include a thin-film transistor. For example, the electronic device can further include a thin-film transistor including a source electrode and a drain electrode, in which the first electrode of the light-emitting device can be electrically connected to the source electrode or the drain electrode. In embodiments, the electronic device can further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. The electronic device can be the same as described herein.
[0311] According to embodiments, an electronic equipment can include a light-emitting device. For example, the electronic equipment can include an electronic device including the light-emitting device. In embodiments, the electronic equipment 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 full transparent display, a partial transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet computer, a phablet computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall having a plurality of displays spliced together, a theater screen, a stadium screen, a phototherapy device, or a signboard.
[0312] [ Figure 1 Description of the Drawings]
[0313] Figure 1 is a schematic cross-sectional view of a light-emitting device 10 according to embodiments. The light-emitting device 10 can include a first electrode 110, an interlayer 130, and a second electrode 150.
[0314] Hereinafter, a structure of a light-emitting device 10 according to embodiments and a method of manufacturing the light-emitting device 10 will be described with reference to Figure 1
[0315] [First Electrode 110]
[0316] In Figure 1 In embodiments, a substrate can be further included under the first electrode 110 or on the second electrode 150. In embodiments, the substrate can be a glass substrate or a plastic substrate. In embodiments, the substrate can be a flexible substrate and can include a plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0317] The first electrode 110 can be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 can be a high work function material that facilitates injection of holes.
[0318] The first electrode 110 can be a reflective electrode, a transreflective electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material for forming the first electrode 110 can include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In embodiments, when the first electrode 110 is a transreflective electrode or a reflective electrode, the material for forming the first electrode 110 can 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.
[0319] The first electrode 110 can have a single layer structure composed of a single layer or a multi-layer structure including a plurality of layers. For example, the first electrode 110 can have a three-layer structure of ITO / Ag / ITO.
[0320] [Interlayer 130]
[0321] The interlayer 130 can be disposed on the first electrode 110. The interlayer 130 can include an emission layer.
[0322] The interlayer 130 can further include a hole transport zone between the first electrode 110 and the emission layer and an electron transport zone between the emission layer and the second electrode 150.
[0323] In addition to various organic materials, the interlayer 130 can further include a metal-containing compound such as an organic metal compound or an inorganic material such as a quantum dot, etc.
[0324] In an embodiment, the interlayer 130 may include two or more emitting units stacked between the first electrode 110 and the second electrode 150, and at least one charge generating layer between adjacent emitting units in the two or more emitting units. When the interlayer 130 includes two or more emitting units and at least one charge generating layer as described above, the light-emitting device 10 may be a series light-emitting device.
[0325] [Hole transport region in interlayer 130]
[0326] Hole transport regions may have: a single-layer structure consisting of a single layer (composed of a single material), a single-layer structure consisting of a single layer containing different materials, or a multi-layer structure including multiple layers containing different materials.
[0327] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof.
[0328] 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 / electron blocking layer structure, wherein the layers of each structure may be stacked from the first electrode 110 in the order described therein, but the structure of the hole transport region is not limited thereto.
[0329] In an implementation, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0330] [Formula 201]
[0331]
[0332] [Formula 202]
[0333]
[0334] In equations 201 and 202,
[0335] L 201 To L 204 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0336] L 205 It can be *-O-*', *-S-*', or *-N(Q) 201)-*', unsubstituted or by at least one R 10a Replacement C1-C 20 Alkylene, unsubstituted, or with at least one R 10a Replacement C2-C 20 alkenyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0337] xa1 to xa4 can each be an integer selected from 0 to 5 independently.
[0338] xa5 can be an integer selected from 1 to 10.
[0339] R 201 To R 204 and Q 201 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0340] R 201 and R 202 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups (e.g., carbazole group, etc.) (e.g., compound HT16, etc.),
[0341] R 203 and R 204 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, and
[0342] na1 can be an integer selected from 1 to 4.
[0343] In embodiments, 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:
[0344]
[0345] In Formula CY201 to Formula CY217, R 10b and R 10c may each independently be the same as described herein with reference to R 10a , ring CY 201 to ring CY 204 may each independently be a C3-C 20 carbocyclyl or C1-C 20 heterocyclyl, and at least one hydrogen in Formula CY201 to Formula CY217 can be unsubstituted or substituted with R 10a as described above.
[0346] According to an embodiment, ring CY 201 to ring CY 204 in Formula CY201 to Formula CY217 can each independently be a phenyl, naphthyl, phenanthryl, or anthryl.
[0347] According to an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 can include at least one of the groups represented by Formula CY201 to Formula CY203.
[0348] According to an embodiment, the compound represented by Formula 201 can include at least one of the groups represented by Formula CY201 to Formula CY203 and at least one of the groups represented by Formula CY204 to Formula CY217.
[0349] According to an embodiment, in Formula 201, xa1may be 1, R 201 may be a group represented by one of Formula CY201 to Formula CY203, xa2may be 0, and R 202 may be a group represented by one of Formula CY204 to Formula CY207.
[0350] According to an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 can each not include the group represented by Formula CY201 to Formula CY203.
[0351] According to an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 can each not include the group represented by Formula CY201 to Formula CY203, and can each independently include at least one of the groups represented by Formula CY204 to Formula CY217.
[0352] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 can each not include the group represented by Formula CY201 to Formula CY217.
[0353] In embodiments, the hole transport region may include one of compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiroTPD, spiroNPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tris(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:
[0354]
[0355]
[0356]
[0357]
[0358]
[0359] The thickness of the hole transport region can be approximately to approximately Within a certain range. For example, the thickness of the hole transport region can be approximately... to approximately Within the range. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer can be approximately... to approximately Within a certain range, and the thickness of the hole transport layer can be approximately... to approximately Within a certain range. For example, the thickness of the hole injection layer can be approximately... to approximately Within a certain range. For example, the thickness of the hole transport layer can be approximately... to approximately Within the above range, when the thicknesses of the hole transport region, hole injection layer, and hole transport layer are within the above range, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0360] The emission assist layer can increase luminous efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block electron leakage from the emission layer to the hole transport region. Materials that may be included in the hole transport region may be included in both the emission assist layer and the electron blocking layer.
[0361] [p-dopant]
[0362] In addition to the materials described above, the hole transport region may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer composed of the charge-generating material).
[0363] The charge-generating material can be, for example, a p-doped agent.
[0364] For example, the lowest unoccupied molecular orbital (LUMO) energy level of a p-doped agent can be less than or equal to about -3.5 eV.
[0365] According to embodiments, p-dopers may include quinone derivatives, cyano-containing compounds, compounds including elements EL1 and EL2, or any combination thereof.
[0366] Examples of quinone derivatives may include TCNQ and F4-TCNQ.
[0367] Examples of cyano-containing compounds may include HAT-CN and compounds represented by formula 221, etc.
[0368]
[0369] [Equation 221]
[0370]
[0371] In Equation 221,
[0372] R 221 To R 223 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, and
[0373] R 221 To R 223 At least one of them can be independently replaced by C3-C respectively. 60 Carbocyclic or C1-C 60 Heterocyclic groups: cyano; -F; -Cl; -Br; -I; C1-C substituted with cyano, -F, -Cl, -Br, -I or any combination thereof 20 Alkyl groups; or any combination thereof.
[0374] In a compound comprising elements EL1 and EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a nonmetal, a metalloid, or any combination thereof.
[0375] Examples of metals can 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.); post-transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); and lanthanides (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.
[0376] Examples of metalloids can include silicon (Si), antimony (Sb), and tellurium (Te), etc.
[0377] Examples of non-metals can include oxygen (O) and halogens (e.g., F, Cl, Br, I, etc.), etc.
[0378] For example, a compound including element EL1 and element EL2 can include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, a metal iodide, etc.), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, etc.), a metal telluride, or any combination thereof.
[0379] Examples of metal oxides can include tungsten oxides (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxides (e.g., VO, V2O3, VO2, V2O5, etc.), molybdenum oxides (e.g., MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), and rhenium oxides (e.g., ReO3, etc.), etc.
[0380] Examples of metal halides can include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides, etc.
[0381] Examples of alkali metal halides can include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI, etc.
[0382] Examples of alkali metal halides can include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2, among others.
[0383] Examples of transition metal halides can include titanium halides (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3, VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halides (e.g., TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halides (e.g., WF3, WCl3, WBr3, WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr2, ReI2, etc.), ferrous halides (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halides (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halides (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halides (e.g., PtF2, PtCl2, PtBr2, PtI2, 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.), among others.
[0384] Examples of post-transition metal halides can include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (e.g., InI3, etc.), and tin halides (e.g., SnI2, etc.), etc.
[0385] Examples of lanthanide metal halides can include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3, etc.
[0386] Examples of metalloid halides can include antimony halides (e.g., SbCl5, etc.), etc.
[0387] Examples of metal tellurides can include alkali metal tellurides (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), post-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.
[0388] [emissive layer in interlayer 130]
[0389] When the light emitting device 10 is a full color light emitting device, the emissive layer can be patterned into a red emissive layer, a green emissive layer, and / or a blue emissive layer according to the sub-pixels. In an embodiment, the emissive layer can have a stack structure of two or more layers among a red emissive layer, a green emissive layer, and a blue emissive layer, where the two or more layers can be in contact with each other or can be separated from each other to emit white light. In an embodiment, the emissive layer can include two or more materials among a red light emitting material, a green light emitting material, and a blue light emitting material, where the two or more materials can be mixed with each other in a single layer to emit white light.
[0390] The emissive layer can include a host and a dopant. The dopant can include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0391] The amount of the dopant in the emission layer can range from about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the host.
[0392] In an embodiment, the emission layer can include a quantum dot.
[0393] In an embodiment, the emission layer can include a delayed fluorescence material. The delayed fluorescence material can be used as a host or as a dopant in the emission layer.
[0394] The thickness of the emission layer can range from about to about . For example, the thickness of the emission layer can range from about to about . When the thickness of the emission layer is within any of the above ranges, excellent light emitting properties can be obtained without a significant increase in driving voltage.
[0395] [Host]
[0396] In an embodiment, the host can further include a compound represented by Formula 301:
[0397] [Formula 301]
[0398] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21
[0399] In Formula 301,
[0400] Ar 301 and L 301 may each independently be C3-C 10a carbocyclyl unsubstituted or substituted with at least one R 60 , or C1-C 10a heterocyclyl unsubstituted or substituted with at least one R 60 ,
[0401] xb11may be 1, 2, or 3,
[0402] xb1may be an integer selected from 0 to 5,
[0403] R 301 may be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C1-C 10a alkyl unsubstituted or substituted with at least one R 60 , C2-C 10a alkenyl unsubstituted or substituted with at least one R 60 , or C3-C 10a substituted C2-C 60 alkynyl, unsubstituted or substituted with at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclyl, unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclyl, -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 ),
[0404] xb21may be an integer selected from 1 to 5, and
[0405] Q 301 to Q 303 may each independently be the same as described herein with reference to Q1.
[0406] In embodiments, in Formula 301, when xb11is 2 or more, two or more Ar 301 may be connected to each other via a single bond.
[0407] In embodiments, the host can include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0408] [Formula 301-1]
[0409]
[0410] [Formula 301-2]
[0411]
[0412] In Formula 301-1 and Formula 301-2,
[0413] Ring A 301 to Ring A 304 may each independently be unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclyl, unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclyl,
[0414] X 301 It can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 (R) 305 ) or Si(R 304 (R) 305 ),
[0415] xb22 and xb23 can each be 0, 1, or 2 independently.
[0416] L 301 xb1 and R 301 Each can be independently identical to the one described in this article.
[0417] L 302 To L 304 Each can be used independently with reference to L in this article. 301 The descriptions are the same.
[0418] xb2 to xb4 can each be independently identical to the description in this paper with reference to xb1, and
[0419] R 302 To R 305 and R 311 To R 314 Each can be used independently with reference to R in this article. 301 The descriptions are the same.
[0420] In embodiments, the host may include alkaline earth metal complexes, post-transition metal complexes, or any combination thereof. For example, the host may include Be complexes (e.g., compound H55), Mg complexes, Zn complexes, or any combination thereof.
[0421] In embodiments, the main body may include one of compounds H1 to H128, 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), 9,10-bis(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-bis(9-carbazolyl)benzene (mCP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP), or any combination thereof:
[0422]
[0423]
[0424]
[0425]
[0426]
[0427]
[0428] [Phosphorescent dopant]
[0429] The phosphorescent dopant can include at least one transition metal as a central metal.
[0430] The phosphorescent dopant can include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0431] The phosphorescent dopant can be electrically neutral.
[0432] In an embodiment, the phosphorescent dopant can include an organometallic compound represented by Formula 401:
[0433] [Formula 401]
[0434] M(L 401 ) xc1 (L 402 ) xc2
[0435] [Formula 402]
[0436]
[0437] In Formula 401 and Formula 402,
[0438] M can be a transition metal (for example, iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
[0439] L 401 may be a ligand represented by Formula 402, and xc1may be 1, 2, or 3, wherein when xc1is 2 or more, two or more L 401 may be the same as or different from each other,
[0440] L 402 may be an organic ligand, and xc2may be 0, 1, 2, 3, or 4, and when xc2is 2 or more, two or more L 402 may be the same as or different from each other,
[0441] X 401 and X 402 may each independently be nitrogen or carbon,
[0442] Ring A 401 and Ring A402 Each can be independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group,
[0443] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 411 )-*'、*-C(Q 411 (Q) 412 )-*'、
[0444] *-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 ) = *' or * = C = *',
[0445] X 403 and X 404 Each can be an independent chemical bond (e.g., covalent or coordinate), O, S, N (Q) 413 ), B(Q) 413 ), P(Q 413 ), C(Q 413 (Q) 414 ) or Si(Q 413 (Q) 414 ),
[0446] Q 411 To Q 414 Each can be independently identical to the one described in reference Q1 in this document.
[0447] R 401 and R 402 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -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 ),
[0448] Q 401 To Q 403 Each can be independently identical to the one described in reference Q1 in this document.
[0449] xc11 and xc12 can each independently be an integer selected from 0 to 10, and
[0450] In Equation 402, * and *' each indicate the binding site with M in Equation 401.
[0451] For example, in equation 402, X 401 It can be nitrogen, and X 402 It can be carbon, or X 401 and X 402 Each can be nitrogen.
[0452] In the implementation, in formula 401, when xc1 is 2 or greater, two or more L 401 The two rings A in 401 Optionally via T as a linking group 402 Connected to each other, or two rings A 402 Optionally via T as a linking group 403 They are interconnected (see compounds PD1 through PD4 and PD7). T 402 and T 403 Each can be used independently with reference to T in this article. 401 The descriptions are the same.
[0453] In Equation 401, L 402 It can be an organic ligand. For example, L... 402 It may include halogen groups, diketone groups (e.g., acetylacetone groups), carboxylic acid groups (e.g., pyridine carboxyl groups), -C (=O), isonitrile groups, -CN groups, phosphorus-containing groups (e.g., phosphin groups, phosphite groups, etc.) or any combination thereof.
[0454] In this embodiment, the phosphorescent dopant may include, for example, one or any combination of compounds PD1 to PD39:
[0455]
[0456]
[0457]
[0458] [Fluorescent dopant]
[0459] Fluorescent dopants may include amine-containing compounds, styrene-containing compounds, or any combination thereof.
[0460] In an embodiment, the fluorescent dopant may include an amine-containing compound represented by formula 501:
[0461] [Formula 501]
[0462]
[0463] In Equation 501,
[0464] Ar 501 L 501 To L 503 R 501 and R 502 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0465] xd1 to xd3 can each be independently 0, 1, 2, or 3, and
[0466] xd4 can be 1, 2, 3, 4, 5 or 6.
[0467] In the implementation, in formula 501, Ar 501 It can be a fused ring group in which three or more monocyclic groups are fused together (e.g., anthracene, 1,2-benzophenanthrene, pyrene, etc.).
[0468] In an implementation, xd4 can be 2 in Equation 501.
[0469] In this embodiment, the fluorescent dopant may include one of compounds FD1 to FD37, DPVBi, DPAVBi, or any combination thereof:
[0470]
[0471]
[0472]
[0473] [Delayed fluorescence materials]
[0474] The emission layer may include a delayed fluorescence material.
[0475] In the specification, the delayed fluorescence material can be selected from any compound that can emit delayed fluorescence based on the delayed fluorescence emission mechanism.
[0476] Depending on the type of other material included in the emission layer, the delayed fluorescence material included in the emission layer can serve as a host or as a dopant.
[0477] According to an embodiment, a difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material can 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 fluorescence material and the singlet energy level (eV) of the delayed fluorescence material is in the above range, upconversion of the delayed fluorescence material from the triplet state to the singlet state can be effectively induced, and thus, the light emitting device 10 can have improved light emitting efficiency.
[0478] In an embodiment, the delayed fluorescence material can include a material including at least one electron donor (e.g., a π-electron rich C3-C 60 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 C1-C 60 cyclic group, etc.) or a material including a C8-C 60 polycyclic group in which two or more cyclic groups are fused while sharing boron (B), etc.
[0479] In an embodiment, the delayed fluorescence material can include, for example, at least one of Compound DF1 to Compound DF14:
[0480]
[0481]
[0482] [Quantum Dot]
[0483] The emission layer can include a quantum dot.
[0484] In the specification, the quantum dot can be a crystal of a semiconductor compound, and can include any material capable of emitting light of various emission wavelengths according to the size of the crystal.
[0485] The diameter of the quantum dot can be, for example, in the range of about 1 nm to about 10 nm.
[0486] The quantum dot can be synthesized through a wet chemical process, a metal organic chemical vapor deposition (MOCVD) process, a molecular beam epitaxy (MBE) process, or any process similar thereto.
[0487] The wet-chemical process is a method including mixing a precursor material with an organic solvent and growing quantum dot particles. When the quantum dot particles grow, the organic solvent naturally serves as a dispersant coordinated on the surface of the quantum dot particles and controls the growth of the quantum dot particles, so that the growth of the quantum dot particles can be controlled by a process that is less costly and can be more easily performed than a gas phase deposition method such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
[0488] The quantum dots can include a Group II-VI semiconductor compound, a Group III-V semiconductor compound, a Group III-VI semiconductor compound, a Group I-III-VI semiconductor compound, a Group IV-VI semiconductor compound, a Group IV element or compound, or any combination thereof.
[0489] Examples of the Group II-VI semiconductor compound can include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, etc.; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, etc.; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, etc.; and any combination thereof.
[0490] Examples of Group III-V semiconductor compounds can include binary compounds such as GaN, GaP, GaAs, GaSb, AIN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and the like; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, and the like; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and the like; and any combination thereof. In embodiments, the Group III-V semiconductor compound can further include a Group II element. Examples of Group III-V semiconductor compounds further including a Group II element can include InZnP, InGaZnP, and InAlZnP, and the like.
[0491] Examples of Group III-VI semiconductor compounds can include binary compounds such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, and the like; ternary compounds such as InGaS3, InGaSe3, and the like; and any combination thereof.
[0492] Examples of Group I-III-VI semiconductor compounds can include ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, and the like; quaternary compounds such as AgInGaS, AgInGaS2, AgInGaSe, AgInGaSe2, CuInGaS, CuInGaS2, and the like; and any combination thereof.
[0493] Examples of Group IV-VI semiconductor compounds can include binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, and the like; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and the like; quaternary compounds such as SnPbSSe, SnPbSeTe, SnPbSTe, and the like; and any combination thereof.
[0494] Examples of Group IV elements or compounds can include single element materials such as Si, Ge, and the like; binary compounds such as SiC, SiGe, and the like; or any combination thereof.
[0495] Each element included in a compound (such as a binary compound, a ternary compound, or a quaternary compound) can be present in the particle at a uniform concentration or a non-uniform concentration.
[0496] In embodiments, the quantum dot can have a single structure in which the concentration of each element in the quantum dot is uniform, or the quantum dot can have a core-shell structure. For example, the material included in the core and the material included in the shell can be different from each other.
[0497] The shell of the quantum dot can serve as a protective layer that prevents chemical denaturation of the core to maintain semiconductor properties and / or can serve as a charging layer that imparts electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient in which the concentration of the material present in the shell decreases toward the center of the core.
[0498] Examples of the shell of the quantum dot can include metal oxides, metalloid oxides, non-metal oxides, semiconductor compounds, and any combination thereof. Examples of the metal oxides, metalloid oxides, or non-metal oxides can include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, etc.; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, etc.; and any combination thereof.
[0499] Examples of the semiconductor compounds can 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, and any combination thereof as described above. For example, the semiconductor compound can include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, and any combination thereof.
[0500] The quantum dot can have a full width at half maximum (FWHM) of a maximum emission wavelength spectrum that is less than or equal to about 45 nm. For example, the quantum dot can have a FWHM of the maximum emission wavelength spectrum that is less than or equal to about 40 nm. For example, the quantum dot can have a FWHM of the maximum emission wavelength spectrum that is less than or equal to about 30 nm. When the FWHM of the maximum emission wavelength spectrum of the quantum dot is within any of these ranges, the quantum dot can have improved color purity or improved color reproducibility. Light emitted by the quantum dot can be emitted in all directions so that a wide viewing angle can be improved.
[0501] In an embodiment, the quantum dot can be in the form of a spherical nanoparticle, a pyramidal nanoparticle, a multi-armed nanoparticle, a cubic nanoparticle, a nanotube, a nanowire, a nanofiber, or a nanoplate, etc.
[0502] Since the energy band gap can be adjusted by controlling the size of the quantum dot, light having various wavelength bands can be obtained from the quantum dot emission layer. Accordingly, by using quantum dots of different sizes, a light emitting device that emits light of various wavelength bands can be implemented. In detail, the size of the quantum dot can be selected to emit red light, green light, and / or blue light. In an embodiment, the size of the quantum dot can be configured to emit white light by combining light of various colors.
[0503] [Electron transport zone in interlayer 130]
[0504] The electron transport zone can have a single layer structure composed of a single layer (composed of a single material), a single layer structure composed of a single layer including different materials, or a multi-layer structure including a plurality of layers including different materials.
[0505] The electron transport zone can include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0506] In an embodiment, the electron transport zone can 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, in which each layer of each structure can be stacked in the order of its respective recitation from the emission layer, but the structure of the electron transport zone is not limited thereto.
[0507] The electron transport zone (e.g., the buffer layer, the hole blocking layer, the electron control layer, or the electron transport layer in the electron transport zone) can include a nitrogen-containing C1-C 60 The metal-free compound of the cyclic group.
[0508] In an embodiment, the electron transport zone can include a compound represented by Formula 601:
[0509] [Formula 601]
[0510] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0511] In Formula 601,
[0512] Ar 601 and L 601 may each independently be unsubstituted or substituted with at least one R10a substituted C3-C 60 carbocyclyl or heterocyclyl, each of which is unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclyl,
[0513] xe11may be 1, 2, or 3,
[0514] xe1may be 0, 1, 2, 3, 4, or 5,
[0515] R 601 may be unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclyl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclyl, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), or -P(=O)(Q 601 )(Q 602 ),
[0516] Q 601 to Q 603 may each independently be the same as described herein with reference to Q1,
[0517] xe21may be 1, 2, 3, 4, or 5, and
[0518] Ar 601 , L 601 , and R 601 may each independently be unsubstituted or substituted by at least one R 10a substituted π- deficient nitrogen-containing C1-C 60 cyclic group.
[0519] In embodiments, in Formula 601, when xe11is 2 or greater, two or more Ar 601 may be connected to each other via a single bond.
[0520] In embodiments, in Formula 601, Ar 601 may be unsubstituted or substituted by at least one R 10a anthracenyl.
[0521] In embodiments, the electron transport zone can include a compound represented by Formula 601-1:
[0522] [Formula 601-1]
[0523]
[0524] In Equation 601-1,
[0525] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and X 614 To X 616 At least one of them can be N,
[0526] L 611 To L 613 Each can be used independently with reference to L in this article. 601 The descriptions are the same.
[0527] xe611 to xe613 can each be independently identical to the description in this document with reference to xe1.
[0528] R 611 To R 613 Each can be used independently with reference to R in this article. 601 The descriptions are the same, and
[0529] R 614 To R 616 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group.
[0530] In the implementation, in formulas 601 and 601-1, xe1 and xe611 to xe613 can each be 0, 1 or 2 independently.
[0531] In embodiments, the electron transport region may include one of compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
[0532]
[0533]
[0534]
[0535] The thickness of the electron transport region can be approximately to approximately Within a certain range. For example, the thickness of the electron transport region can be approximately... to approximately Within the range. 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, hole blocking layer, or electron control layer can each be independently within approximately [a certain range]. to approximately Within a certain range, and the thickness of the electron transport layer can be approximately... to approximately Within a certain range. For example, the thickness of the buffer layer, hole blocking layer, or electronic control layer can each be independently within approximately [a certain range]. to approximately Within a certain range. For example, the thickness of the electron transport layer can be approximately... to approximately Within the above range, when the thickness of the buffer layer, hole blocking layer, electron control layer, electron transport layer and / or electron transport region is within the above range, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.
[0536] In addition to the materials mentioned above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further include a metallic material.
[0537] Metal-containing materials may include alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The metal ion in an alkali metal complex may be Li, Na, K, Rb, or Cs ions, and the metal ion in an alkaline earth metal complex may be Be, Mg, Ca, Sr, or Ba ions. The ligands coordinated to the metal ions of the alkali metal complex or alkaline earth metal complex may independently include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, cyclopentadiene, or any combination thereof.
[0538] For example, metallic materials may include Li complexes. Li complexes may include, for example, compounds ET-D1(Liq) or ET-D2:
[0539]
[0540] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may contact (e.g., directly contact) the second electrode 150.
[0541] The electron injection layer can have a single layer structure composed of a single layer (consisting of a single material), a single layer structure composed of a single layer comprising different materials, or a multi-layer structure including multiple layers comprising different materials.
[0542] The electron injection layer can 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.
[0543] The alkali metal can include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal can include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal can include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0544] The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound can be an oxide, a halide (e.g., fluoride, chloride, bromide, iodide, etc.), or a telluride of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
[0545] The alkali metal-containing compound can include an alkali metal oxide such as Li2O, Cs2O, K2O, etc.; an alkali metal halide such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, etc.; or any combination thereof. The alkaline earth metal-containing compound can include an alkaline earth metal oxide such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying the condition of 0 < x < 1) or Ba x Ca 1-x O (where x is a real number satisfying the condition of 0 < x < 1), etc. The rare earth metal-containing compound can include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In embodiments, the rare earth metal-containing compound can include a lanthanide telluride. Examples of the lanthanide telluride can include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3, etc.
[0546] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may include: alkali metal ions, alkaline earth metal ions, or rare earth metal ions; and ligands bonded to the metal ions (e.g., hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthridine, cyclopentadiene, or any combination thereof).
[0547] In embodiments, the electron injection layer may consist of alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof as described above. In embodiments, the electron injection layer may further include organic materials (e.g., compounds represented by Formula 601).
[0548] According to embodiments, 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 alkali metals, alkaline earth metals, rare earth metals, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposition layer, an RbI:Yb co-deposition layer, or a LiF:Yb co-deposition layer, etc.
[0549] When the electron injection layer further includes organic materials, alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof may be uniformly or non-uniformly dispersed in the matrix including the organic materials.
[0550] The thickness of the electron injection layer can be approximately to approximately Within a certain range. For example, the thickness of the electron-injected layer can be approximately... to approximately Within the range described above, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage when the thickness of the electron injection layer is within any of the above-mentioned range.
[0551] [Second electrode 150]
[0552] The second electrode 150 may be disposed on the interlayer 130 having the structure described above. The second electrode 150 may be a cathode serving 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, alloy, conductive compound, or any combination thereof.
[0553] The second electrode 150 can include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 can be a transmissive electrode, a transreflective electrode, or a reflective electrode.
[0554] The second electrode 150 can have a single layer structure or a multi-layer structure.
[0555] [Cap Layer]
[0556] The light emitting device 10 can include a first cap layer outside the first electrode 110 and / or a second cap layer outside the second electrode 150. For example, the light emitting device 10 can have a structure in which the first cap layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked in this recited order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second cap layer are stacked in this recited order, or a structure in which the first cap layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second cap layer are stacked in this recited order.
[0557] Light generated in the emission layer of the interlayer 130 of the light emitting device 10 can pass through the first electrode 110, which can be a transreflective electrode or a transmissive electrode, and pass through the first cap layer. Light generated in the emission layer of the interlayer 130 of the light emitting device 10 can pass through the second electrode 150, which can be a transreflective electrode or a transmissive electrode, and pass through the second cap layer.
[0558] The first cap layer and the second cap layer can increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light emitting device 10 is increased, so that the light emitting efficiency of the light emitting device 10 can be improved.
[0559] The first cap layer and the second cap layer can each include a material having a refractive index greater than or equal to about 1.6 (with respect to a wavelength of about 589 nm).
[0560] The first cap layer and the second cap layer can each independently be an organic cap layer including an organic material, an inorganic cap layer including an inorganic material, or an organic-inorganic composite cap layer including an organic material and an inorganic material.
[0561] At least one of the first cap layer and the second cap layer can 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 can each be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.
[0562] According to embodiments, at least one of the first capping layer and the second capping layer can each independently include an amine-containing compound.
[0563] In embodiments, at least one of the first capping layer and the second capping layer can each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0564] According to embodiments, at least one of the first capping layer and the second capping layer can each independently include one of compounds HT28 to HT33, one of compounds CP1 to CP6, β-NPB, or any combination thereof:
[0565]
[0566]
[0567] [Membrane]
[0568] The organometallic compound represented by Formula 1 can be included in various membranes. Embodiments provide a membrane including the organometallic compound represented by Formula 1. The membrane can 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 polarizing layer, a quantum dot-containing layer, etc.), a light blocking member (e.g., a light reflecting layer, a light absorbing layer, etc.), or a protective member (e.g., an insulating layer, a dielectric layer, etc.), etc.
[0569] [Electronic device]
[0570] The light emitting device can be included in various electronic devices. For example, the electronic device including the light emitting device can be a light emitting device or an authentication device, etc.
[0571] In addition to the light emitting device, the electronic device (e.g., a light emitting device) can 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 can be arranged in at least one direction in which light emitted from the light emitting device travels. For example, the light emitted from the light emitting device can be blue light or white light. The light emitting device can be the same as described herein. According to embodiments, the color conversion layer can include quantum dots. The quantum dots can be, for example, quantum dots as described herein.
[0572] The electronic device can include a substrate. The substrate can include a plurality of sub-pixels, the color filter can include a plurality of color filter regions respectively corresponding to the plurality of sub-pixels, and the color conversion layer can include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixels.
[0573] A pixel defining film can be arranged between the plurality of sub-pixels to define each sub-pixel.
[0574] The color filter can 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 can further include a plurality of color conversion regions and a light-shielding pattern disposed between the plurality of color conversion regions.
[0575] The color filter region (or the color conversion region) can include a first region emitting first color light, a second region emitting second color light, and / or a third region emitting third color light, wherein the first color light, the second color light, and / or the third color light can have different maximum emission wavelengths from each other. In an embodiment, the first color light can be red light, the second color light can be green light, and the third color light can be blue light. In an embodiment, the color filter region (or the plurality of color conversion regions) can include quantum dots. In an embodiment, the first region can include red quantum dots, the second region can include green quantum dots, and the third region can not include quantum dots. The quantum dots can be the same as described herein. The first region, the second region, and / or the third region can each include a scatterer.
[0576] In an embodiment, the light emitting device can emit first light, the first region can absorb the first light to emit first-first color light, the second region can absorb the first light to emit second-first color light, and the third region can absorb the first light to emit third-first color light. In an embodiment, the first-first color light, the second-first color light, and the third-first color light can have different maximum emission wavelengths. For example, the first light can be blue light, the first-first color light can be red light, the second-first color light can be green light, and the third-first color light can be blue light.
[0577] In addition to the light emitting device as described above, the electronic device can further include a thin film transistor. The thin film transistor can include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode can be electrically connected to any one of the first electrode and the second electrode of the light emitting device.
[0578] The thin film transistor can further include a gate electrode or a gate insulating film, etc.
[0579] The active layer can include crystalline silicon, amorphous silicon, an organic semiconductor, or an oxide semiconductor, etc.
[0580] The electronic device can further include a sealing portion for sealing the light emitting device. The sealing portion can be disposed between the color filter and / or the color conversion layer and the light emitting device. The sealing portion can allow light from the light emitting device to be extracted to the outside, and can prevent environmental air and / or moisture from penetrating into the light emitting device. The sealing portion can be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion can be a thin film encapsulation layer including at least one layer of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device can be flexible.
[0581] According to the use of the electronic device, various functional layers can be further included on the sealing part in addition to the color filter and / or the color conversion layer. Examples of the functional layer can include a touch screen layer, a polarizing layer, and the like. The touch screen layer can be a pressure sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication device can be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (e.g., a fingertip, a pupil, or the like).
[0582] In addition to the light emitting device as described above, the authentication device can further include a biometric information collector.
[0583] The electronic device can be applied to various displays, light sources, lighting devices, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical tools (e.g., electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various measuring tools, meters (e.g., meters for vehicles, aircraft, and ships), and projectors, and the like.
[0584] [Electronic appliances]
[0585] The light emitting device can be included in various electronic appliances.
[0586] In an embodiment, the electronic appliance including the light emitting device can be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor lamp, an outdoor lamp, a signal lamp, a head-up display, a full transparent display, a partial transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall having a plurality of displays spliced together, a theater screen, a stadium screen, a light therapy device, or a signboard.
[0587] The light emitting device can have excellent luminous efficiency and long lifespan, and thus the electronic appliance including the light emitting device can have characteristics such as high brightness, high resolution, and low power consumption.
[0588] [ Figure 2 and Figure 3 Description]
[0589] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment.
[0590] Figure 2An electronic device can include a substrate 100, a thin film transistor (TFT), a light emitting device, and a sealing portion 300 sealing the light emitting device.
[0591] The substrate 100 can be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 can be disposed on the substrate 100. The buffer layer 210 can prevent penetration of impurities through the substrate 100 and can provide a flat surface on the substrate 100.
[0592] The TFT can be disposed on the buffer layer 210. The TFT can include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0593] The active layer 220 can include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and can include a source region, a drain region, and a channel region.
[0594] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 can be disposed on the active layer 220, and the gate electrode 240 can be disposed on the gate insulating film 230.
[0595] An interlayer insulating film 250 can be disposed on the gate electrode 240. The interlayer insulating film 250 can be disposed between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260, and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
[0596] The source electrode 260 and the drain electrode 270 can be disposed on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 can be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 can contact exposed portions of the source region and the drain region of the active layer 220, respectively.
[0597] The TFT can be electrically connected to the light emitting device to drive the light emitting device, and can be covered and protected by a passivation layer 280. The passivation layer 280 can include an inorganic insulating film, an organic insulating film, or any combination thereof. The light emitting device can be provided on the passivation layer 280. The light emitting device can include a first electrode 110, an interlayer 130, and a second electrode 150.
[0598] The first electrode 110 can be disposed on the passivation layer 280. The passivation layer 280 can not completely cover the drain electrode 270 and can expose a portion of the drain electrode 270. The first electrode 110 can be connected (e.g., electrically connected) to the exposed portion of the drain electrode 270.
[0599] A pixel defining film 290, including insulating material, may be disposed on the first electrode 110. The pixel defining film 290 may expose an area of the first electrode 110, and an interlayer 130 may be formed in the exposed area of the first electrode 110. The pixel defining film 290 may be a polyimide or polyacrylic acid organic film. Although not explicitly stated... Figure 2 As shown, however, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel-defining film 290, thus being provided as a common layer.
[0600] The second electrode 150 may be disposed on the interlayer 130, and a capping layer 170 may further be included on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0601] A sealing portion 300 may be disposed on the capping layer 170. The sealing portion 300 may be disposed on the light-emitting device to protect it from moisture and / or oxygen. The sealing portion 300 may include an inorganic film, which includes silicon nitride (SiN). x ), silicon dioxide (SiO) x Indium tin oxide, indium zinc oxide, or any combination thereof; organic membranes, including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate, polyacrylic acid, etc.), epoxy resins (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of inorganic and organic membranes.
[0602] Figure 3 This is a schematic cross-sectional view of an electronic device according to an embodiment.
[0603] Figure 3 electronic devices and Figure 2 The electronic device may differ at least in that it further includes a light-shielding pattern 500 and a functional area 400 on the sealed portion 300. The functional area 400 may be a color filter area, a color conversion area, or a combination of both. According to an embodiment, Figure 3 The light-emitting device included in the electronic device may be a series light-emitting device.
[0604] [ Figure 4 [Description]
[0605] Figure 4 This is a schematic perspective view of an electronic device 1 including a light-emitting device according to an embodiment.
[0606] The electronic device 1 can be not only a portable electronic apparatus such as a mobile phone, a smart phone, a tablet computer, a mobile communication terminal, an electronic notebook computer, an electronic book, a portable multimedia player (PMP), a navigation device, or an ultra-mobile personal computer (UMPC), but also various products such as a television, a laptop computer, a monitor, a billboard, or an Internet of Things (IoT) device. The electronic device 1 can be any such product or a part thereof as described above.
[0607] In an embodiment, the electronic device 1 can 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 the wearable device. However, embodiments are not limited thereto.
[0608] In an embodiment, examples of the electronic device 1 can include an instrument panel and a center information display (CID) on a center console or an instrument panel of a vehicle, an in-vehicle rearview mirror display replacing a side mirror of a vehicle, an entertainment display for a rear seat of a vehicle, a display disposed on a backrest of a front seat, a head-up display (HUD) installed in front of a vehicle or projected on a front window glass, or a computer-generated hologram augmented reality head-up display (CGH AR HUD). For the convenience of explanation, Figure 4 An embodiment in which the electronic device 1 is a smart phone is illustrated.
[0609] The electronic device 1 can include a display area DA and a non-display area NDA outside the display area DA. The display device can implement an image through a two-dimensional pixel array disposed in the display area DA.
[0610] The non-display area NDA can be an area in which an image is not displayed, and can surround (e.g., completely surround) the display area DA. A driver for providing an electrical signal or power to a display element disposed in the display area DA can be disposed in the non-display area NDA. A pad to which an electronic element or a printed circuit substrate can be electrically connected can be disposed in the non-display area NDA.
[0611] In the electronic device 1, a length in the x-axis direction and a length in the y-axis direction can be different from each other. In an embodiment, as illustrated in FIG. 1A, the length in the x-axis direction can be shorter than the length in the y-axis direction. In an embodiment, as illustrated in FIG. 1B, the length in the x-axis direction can be the same as the length in the y-axis direction. In an embodiment, as illustrated in FIG. 1C, the length in the x-axis direction can be longer than the length in the y-axis direction. Figure 4
[0612] [ Figure 5 and Figures 6A to 6C description]
[0613] Figure 5 FIG. 1 is a schematic perspective view of the exterior of a vehicle 1000 according to an embodiment. Figures 6A to 6C FIG. 2 is a schematic view of the interior of the vehicle 1000 according to an embodiment.
[0614] Reference Figure 5 , Figure 6A , Figure 6B and Figure 6C Embodiments of the vehicle 1000 can refer to various devices for moving an object to be transported, such as a person, an object, or an animal, from a starting point to a destination point. The vehicle 1000 can include a vehicle traveling on a road or a track, a ship moving on the ocean or a river, and an airplane flying in the air using air, etc.
[0615] The vehicle 1000 can travel on a road or a track. The vehicle 1000 can move in a selectable direction according to rotation of at least one wheel. Examples of the vehicle 1000 can include a three- or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover, a bicycle, and a train traveling on a track.
[0616] The vehicle 1000 can include a body having an interior and an exterior, and a chassis as a part other than the body in which mechanical devices required for driving are installed. The exterior of the body of the vehicle 1000 can include a front panel, a hood, a roof panel, a rear panel, a trunk, and a pillar provided at a boundary between doors, etc. The chassis of the vehicle 1000 can include a power generation device, a power transmission device, a driving device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, front and rear wheels, and left and right wheels, etc.
[0617] The vehicle 1000 can include a side window glass 1100, a front window glass 1200, a side mirror 1300, an instrument panel 1400, a center console 1500, a passenger seat instrument panel 1600, and a display device 2.
[0618] The side window glass 1100 and the front window glass 1200 can be divided by a pillar disposed between the side window glass 1100 and the front window glass 1200.
[0619] The side window glass 1100 can be installed on a side of the vehicle 1000. In an embodiment, the side window glass 1100 can be installed on a door of the vehicle 1000. A plurality of side window glasses 1100 can be provided and can face each other. In an embodiment, the side window glass 1100 can include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 can be disposed adjacent to the instrument panel 1400, and the second side window glass 1120 can be disposed adjacent to the passenger seat instrument panel 1600.
[0620] In an embodiment, the side window glasses 1100 can be spaced apart from each other in the x-axis direction or a direction opposite to the x-axis direction. For example, the first side window glass 1110 and the second side window glass 1120 can be spaced apart from each other in the x-axis direction or a direction opposite to the x-axis direction. For example, a virtual straight line L connecting the side window glasses 1100 can extend in the x-axis direction or a direction opposite to the x-axis direction. For example, a virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other can extend in the x-axis direction or a direction opposite to the x-axis direction.
[0621] The front window glass 1200 can be installed at a front portion of the vehicle 1000. The front window glass 1200 can be disposed between the side window glasses 1100 facing each other.
[0622] The side mirror 1300 can provide a rear view of the vehicle 1000. The side mirror 1300 can be installed on an outside of a vehicle body. In an embodiment, a plurality of side mirrors 1300 can be provided. For example, one of the plurality of side mirrors 1300 can be disposed at an outer side of the first side window glass 1110, and another of the plurality of side mirrors 1300 can be disposed at an outer side of the second side window glass 1120.
[0623] The instrument panel 1400 can be disposed in front of a steering wheel. The instrument panel 1400 can include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a steering signal indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a trip recorder, an automatic shift lever indicator light, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0624] The center console 1500 can include a control panel on which buttons for adjusting an audio device, an air conditioning device, and a seat heater are disposed. The center console 1500 can be disposed at a side of the instrument panel 1400.
[0625] The passenger seat instrument panel 1600 can be spaced apart from the instrument panel 1400, and the center console 1500 can be disposed between the instrument panel 1400 and the passenger seat instrument panel 1600. In an embodiment, the instrument panel 1400 can be disposed to correspond to a driver seat (not shown), and the passenger seat instrument panel 1600 can be disposed to correspond to a passenger seat (not shown). In an embodiment, the instrument panel 1400 can be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 can be adjacent to the second side window glass 1120.
[0626] In an embodiment, the display device 2 can include the display panel 3, and the display panel 3 can display an image. The display device 2 can be disposed inside the vehicle 1000. In an embodiment, the display device 2 can be disposed between side windows 1100 facing each other. The display device 2 can be disposed on at least one of the instrument panel 1400, the center console 1500, and the passenger seat panel 1600.
[0627] The display device 2 can include an organic light emitting display device, an inorganic electroluminescence (EL) display device, or a quantum dot display device, etc. Hereinafter, an organic light emitting display device including a light emitting device according to the disclosure will be described as an example, but various types of display devices as described above can be used in an embodiment.
[0628] Referring to Figure 6A , the display device 2 can be disposed on the center console 1500. In an embodiment, the display device 2 can display navigation information. In an embodiment, the display device 2 can display information on audio settings, video settings, or vehicle settings.
[0629] Referring to Figure 6B , the display device 2 can be disposed on the instrument panel 1400. When the display device 2 is disposed on the instrument panel 1400, the instrument panel 1400 can display driving information, etc. through the display device 2. For example, the instrument panel 1400 can display driving information, etc. numerically. The instrument panel 1400 can display vehicle information and driving information numerically as an image. For example, a needle and a meter of a tachometer and various warning lamps or icons can be displayed by a digital signal.
[0630] Referring to Figure 6C , the display device 2 can be disposed on the passenger seat panel 1600. The display device 2 can be embedded in the passenger seat panel 1600 or can be disposed on the passenger seat panel 1600. In an embodiment, the display device 2 disposed on the passenger seat panel 1600 can display an image related to information displayed on the instrument panel 1400 and / or information displayed on the center console 1500. In an embodiment, the display device 2 disposed on the passenger seat panel 1600 can display information different from information displayed on the instrument panel 1400 and / or information displayed on the center console 1500.
[0631] [Manufacturing method]
[0632] Each layer included in the hole transport zone, the emission layer, and each layer included in the electron transport zone can be formed in a selected zone by using an appropriate method selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging.
[0633] When the layers comprising the hole transport region, the emitter layer, and the layers comprising the electron transport region are formed by vacuum deposition, the deposition can be carried out at a deposition temperature of about 100°C to about 500°C, and at a deposition temperature of about 10°C. -8 To about 10 -3 The vacuum degree and about to approximately The deposition rate is determined by the material to be included in the layer to be formed and the structure of the layer to be formed.
[0634] [Terminology limitations]
[0635] As used in this article, the term "C3-C" 60 A "carbocyclic group" can be a cyclic group consisting only of carbon atoms as cyclic atoms and having 3 to 60 carbon atoms, and as used herein by the term "C1-C". 60 A "heterocyclic group" can be a cyclic group having 1 to 60 carbon atoms and, in addition to carbon atoms, having at least one heteroatom as a cyclic atom. (C3-C) 60 Carbocyclic groups and C1-C 60 Heterocyclic groups can be monocyclic groups consisting of a single ring or polycyclic groups in which two or more rings are fused together. For example, C1-C 60 Heterocyclic groups can have 3 to 61 cyclic atoms.
[0636] As used in this article, the term "cyclic group" can refer to C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group.
[0637] As used in this article, “π-electron-rich C3-C” 60 "Cyclic group" can be a cyclic group having 3 to 60 carbon atoms and may not include *-N=*' as a cyclic moiety, and as used herein, "a nitrogen-containing C1-C group lacking π electrons". 60 The "cyclic group" may be a heterocyclic group having 1 to 60 carbon atoms and may include *-N=*' as the cyclic part.
[0638] In the implementation,
[0639] C3-C 60 The carbocyclic group can be a T1 group, or a group in which two or more T1 groups are fused together (e.g., cyclopentadienyl, adamantyl, norbornel, phenyl, pentaenyl, naphthyl, azuleyl, indaryl, acenaphthel, phenanthrene, anthreneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenantyl, perylene, penfenyl, heptaenyl, tetraphenyl, framyl, hexaphenyl, pentaphenyl, rubidyl, keratyl, ovoleyl, indole, fluorenyl, spirodifluorenyl, benzofluorenyl, indolephenyl or indoleanthryl).
[0640] C1-C 60 The heterocyclic group can be a T2 group, wherein two or more T2 groups are fused together, or wherein one or more T2 groups and one or more T1 groups are fused together (e.g., pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiophene, benzofuranyl, carbazole, dibenzothiophene, dibenzofuranyl, dibenzofuranyl, indocarbazole, indolecarbazole, benzofuranyl, benzothiophenecarbazole, benzothiophenecarbazole, benzoindocarbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthophene, benzonaphthothiophene, benzofuranyl, benzofuranyl dibenzofuranyl, benzofuranyl dibenzofuranyl). benzothiophene, benzothiophene, dibenzothiophene, pyrazolyl, imidazole, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benzoisooxazolyl, benzothiazolyl, benzoisothiazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzo[] Quinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cenolinyl, phthalazinyl, naphthidyl, imidazopyridyl, imidazopyrimidyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazoyl, azafluorenyl, azadibenzothiophenyl, azadibenzofuranyl, etc.
[0641] C3-C rich in π electrons 60 The cyclic group can be a T1 group, wherein two or more T1 groups are fused together, a T3 group, wherein two or more T3 groups are fused together, or wherein one or more T3 groups and one or more T1 groups are fused together (e.g., C3-C). 60 Carbocyclic, 1H-pyrrole, thiorrole, borocyclopentadienyl, 2H-pyrrole, 3H-pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiorrole, benzothiophene, benzofuranyl, carbazole, dibenzothiorrole, dibenzothiophene, dibenzofuranyl, indole-carbazole, benzofuran-carbazole, benzothiophene-carbazole, benzothiorrole-carbazole, benzoindole-carbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthophene, benzonaphthorrole, benzofuran-dibenzofuranyl, benzofuran-dibenzothiophene, benzothiophene-dibenzothiophene, etc.), and
[0642] Nitrogen-containing C1-C lacking π electrons 60The cyclic group can be a T4group, a group in which two or more T4groups are fused to each other, a group in which one or more T4groups and one or more T1groups are fused to each other, a group in which one or more T4groups and one or more T3groups are fused to each other, or a group in which one or more T4groups, one or more T1groups, and one or more T3groups are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, benzoisothiazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiophenyl, azadibenzothiophenyl, azadibenzofuranyl, and the like), wherein
[0643] The T1group can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutene, cyclopentene, cyclopentadiene, cyclohexene, cyclohexadiene, cycloheptene, adamantane, norbornane (or bicyclo[2.2.1]heptane), norbornene, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane, or phenyl,
[0644] The T2group can be furanyl, thienyl, 1H-pyrrolyl, thiopyrrolyl, borolyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiopyrrolyl, azaborolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl, or dihydropyridazinyl,
[0645] The T3group can be furanyl, thienyl, 1H-pyrrolyl, thiopyrrolyl, or borolyl, and
[0646] The T4group can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiopyrrolyl, azaborolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, or tetrazinyl.
[0647] The terms "cyclic group," "C3-C 60 carbocyclyl," "C1-C 60 heterocyclyl," "π-electron rich C3-C 60 cyclic group," and "π-electron deficient nitrogen-containing C1-C 60 cyclic group" can each be a group that is fused to any cyclic group, monovalent group, or polyvalent group (e.g., divalent group, trivalent group, tetravalent group, etc.) according to the structure of the formula in which the corresponding term is used. For example, "phenyl" can be benzo, phenyl, or phenylene, etc., which can be readily understood by one of ordinary skill in the art according to the structure of the formula in which "phenyl" is used.
[0648] In embodiments, examples of monovalent C3-C 60 carbocyclyl and monovalent C1-C 60 heterocyclyl can include C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, and monovalent non-aromatic fused heteropolycyclic group.
[0649] examples of divalent C3-C 60 carbocyclyl and divalent C1-C 60 heterocyclyl can include C3-C 10 cycloalkylene, C1-C 10 heterocycloalkylene, C3-C 10 cycloalkenylene, C1-C 10 heterocycloalkenylene, C6-C 60 arylene, C1-C 60 heteroarylene, divalent non-aromatic fused polycyclic group, and divalent non-aromatic fused heteropolycyclic group.
[0650] The term "C1-C 60 alkyl" as used herein can be a straight-chain or branched monovalent aliphatic hydrocarbon group having 1 to 60 carbon atoms, and examples thereof can include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, t-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, t-hexyl, n-heptyl, isohexyl, sec-heptyl, t-heptyl, n-octyl, isooctyl, sec-octyl, t-octyl, n-nonyl, isononyl, sec-nonyl, t-nonyl, n-decyl, isodecyl, sec-decyl, t-decyl, and the like. The term "C1-C 60 alkylene" as used herein can be a divalent group having the same structure as C1-C 60 alkyl.
[0651] As used in this article, the term "C2-C" 60 "Alkenyl" can be in C2-C 60 Alkyl groups are monovalent hydrocarbon groups with one or more carbon-carbon double bonds in the middle or at the end, and examples may include vinyl, propenyl, and butenyl groups, etc. The term "C2-C" is used herein. 60 "Alkenyl" can be C2-C 60 Alkenes have divalent groups with the same structure.
[0652] As used in this article, the term "C2-C" 60 "Alkyne group" can be at C2-C 60 Alkyl groups have one or more carbon-carbon triple bonds in the middle or at the end, and examples may include ethynyl and propynyl groups, etc. As used herein, the term "C2-C" is used... 60 "Isynyl group" can be related to C2-C 60 The alkynyl group is a divalent group with the same structure.
[0653] As used in this article, the term "C1-C" 60 "Alkoxy" can be composed of -O(A 101 (where A) 101 Can be C1-C 60 Alkyl groups are monovalent groups, and examples of them may include methoxy, ethoxy, and isopropoxy groups.
[0654] As used in this article, the term "C3-C" 10 "Cycloalkyl" can be a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples of it 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. The term "C3-C" as used herein... 10 "Cycloalkylene" can be C3-C 10 Cycloalkyl groups have the same divalent structure.
[0655] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" can be a monovalent cyclic group having 1 to 10 carbon atoms and further including at least one heteroatom as a cyclic atom in addition to the carbon atoms, and examples may include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiopheneyl, etc. The term "C1-C" as used herein... 10 "Heterocyclic alkyl" can be C1-C 10 Heterocyclic alkyl groups have divalent groups with the same structure.
[0656] The term C3-C used in this article 10 Cycloalkenyl groups can be monovalent cyclic groups having 3 to 10 carbon atoms and at least one carbon-carbon double bond in their cyclic structure, and are non-aromatic; examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl, etc. As used herein, the term "C3-C" is used... 10 "Iridylene" can be related to C3-C 10 Cycloalkenyl groups are divalent groups with the same structure.
[0657] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" can be a monovalent cyclic group having 1 to 10 carbon atoms, further including at least one heteroatom as a cyclic atom in addition to the carbon atoms, and having at least one double bond in its ring structure. C1-C 10 Examples of heterocyclic alkenyl groups may include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiopheneyl, etc., as used herein with the term "C1-C". 10 "Heterocyclic alkenyl" can be C1-C 10 Heterocyclic alkenyl groups are divalent groups with the same structure.
[0658] As used in this article, the term "C6-C" 60 "Aryl" can be a monovalent group in a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein in the term "C6-C". 60 "Arylene" can be a divalent group in a carbocyclic aromatic system with 6 to 60 carbon atoms. (C6-C) 60 Examples of aryl groups may include phenyl, pentanenyl, naphthyl, azulel, indole, acenaphthel, phenanthyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentanenyl, heptanenyl, tetraphenyl, framyl, hexaphenyl, pentaphenyl, rubiginyl, myristyl, and ovoleyl, etc. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the rings can fused together.
[0659] As used in this article, the term "C1-C" 60 "Heteroaryl" can be a monovalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a cyclizing atom in addition to carbon atoms. The term "C1-C" is used herein. 60 "Hypo-heteroaryl" can be a divalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a cyclic atom in addition to carbon atoms. C1-C 60Examples of heteroaryl groups can include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, and naphthyridinyl groups, and the like. When C1-C 60 Heteroaryl and C1-C 60 When each heteroarylene group includes two or more rings, the individual rings can be fused to one another.
[0660] The term "monovalent non-aromatic fused polycyclic group" as used herein can be a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to one another, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of monovalent non-aromatic fused polycyclic groups can include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl, and indenanthracenyl groups, and the like. The term "divalent non-aromatic fused polycyclic group" as used herein can be a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.
[0661] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein can be a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings fused to one another, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and no aromaticity in its entire molecular structure. Examples of monovalent non-aromatic fused heteropolycyclic groups can include pyrrolyl, thiophenyl, furanyl, indolyl, benzoindolyl, naphthoindolyl, isoindolyl, benzoisoindolyl, naphthoisoindolyl, benzothiopyrrolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiopyrrolyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azaf luorenyl, azadibenzothiopyrrolyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzothiopyrrolocarbazolyl, benzindolocarbazolyl, benzo carbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzonaphthothiopyrrolyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, and benzothiophenodibenzothiophenyl groups, and the like. The term "divalent non-aromatic fused heteropolycyclic group" as used herein can be a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group as described above.
[0662] The term "C6-C 60 "Aryloxy" can be -O(A 102(where A) 102 It can be C6-C 60 Aryl) groups, and as used herein, the term "C6-C" 60 "Arylthio" can be formed by -S(A 103 (where A) 103 It can be C6-C 60 (aryl) represents a group.
[0663] As used in this article, the term "C7-C" 60 "Aryl" can be composed of -(A 104 A 105 (where A) 104 Can be C1-C 54 Alkylene, and A 105 It can be C6-C 59 Aryl) group, and as used herein, the term "C2-C" 60 "Heteroarylene" can be composed of -(A 106 (A) 107 (where A) 106 Can be C1-C 59 Alkylene, and A 107 Can be C1-C 59 (Heteroaryl) represents a group.
[0664] As used in this article, the term "C3-C" 60 "Carbocyclic group" includes C3-C 50 carbonyl group, C3-C 40 carbonyl group, C3-C 30 carbonyl group, C3-C 20 carbonyl group or C3-C 10 carbon cyclo group;
[0665] The term "C1-C" 60 "Heterocyclic groups" include C1-C 50 Heterocyclic groups, C1-C 40 Heterocyclic groups, C1-C 30 Heterocyclic groups, C1-C 20 Heterocyclic groups or C1-C 10 Heterocyclic groups;
[0666] The term "C1-C" 60 "alkyl" includes C1-C 50 Alkyl, C1-C 30 Alkyl, C1-C 20 Alkyl or C1-C 10 alkyl;
[0667] The term "C2-C" 60 "Alkenyl" includes C2-C 30alkenyl, C2-C 20 alkenyl or C2-C 10 alkenyl;
[0668] The term "C2-C 60 alkynyl" includes C2-C 30 alkynyl, C2-C 20 alkynyl or C2-C 10 alkynyl;
[0669] The term "C1-C 60 alkoxy" includes C1-C 30 alkoxy, C1-C 20 alkoxy or C1-C 10 alkoxy;
[0670] The term "C6-C 60 aryl" includes C6-C 50 aryl, C6-C 40 aryl, C6-C 30 aryl, C6-C 20 aryl or C6-C 15 aryl;
[0671] The term "C1-C 60 heteroaryl" includes C1-C 50 heteroaryl, C1-C 40 heteroaryl, C1-C 30 heteroaryl, C1-C 20 heteroaryl or C1-C 10 heteroaryl;
[0672] "monovalent non-aromatic fused polycyclic group" includes C8-C 60 monovalent non-aromatic fused polycyclic group, C8-C 50 monovalent non-aromatic fused polycyclic group, C8-C 40 monovalent non-aromatic fused polycyclic group, C8-C 30 monovalent non-aromatic fused polycyclic group or C8-C 20 monovalent non-aromatic fused polycyclic group;
[0673] The term "monovalent non-aromatic fused heteropolycyclic group" includes C1-C 60 monovalent non-aromatic fused heteropolycyclic group, C1-C 50 monovalent non-aromatic fused heteropolycyclic group, C1-C 40 monovalent non-aromatic fused heteropolycyclic group, C1-C 30 monovalent non-aromatic fused heteropolycyclic group or C1-C 20 monovalent non-aromatic fused heteropolycyclic group;
[0674] The term "C6-C 60"Aryloxy groups" include C6-C 50 Aryloxy group, C6-C 40 Aryloxy group, C6-C 30 Aryloxy group, C6-C 20 Aryloxy or C6-C 15 aryloxy;
[0675] The term "C6-C" 60 "Arylthio" includes C6-C 50 Arylthio, C6-C 40 Arylthio, C6-C 30 Arylthio, C6-C 20 Aryl thiols or C6-C 15 Arylthio;
[0676] The term "C7-C" 60 "Aryl" includes C7-C 50 Aryl group, C7-C 40 Aryl group, C7-C 30 Aryl group, C7-C 20 Aryl or C7-C 15 Aryl alkyl groups; and
[0677] The term "C2-C" 60 "Heteroarylene" includes C2-C 50 Heteroaryl, C2-C 40 Heteroaryl, C2-C 30 Heteroaryl, C2-C 20 Heteroaryl or C2-C 15 Heteroalkyl groups.
[0678] In the specification, the group "R" 10a "Can be:
[0679] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;
[0680] Each of the following C1-C that is not substituted or is substituted: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 heteroaryl, -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;
[0681] Each of the following C3-Cs that are not substituted or are substituted by: 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 heteroaryl, -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
[0682] -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)(Q31 )(Q 32 )。
[0683] In the specification, Q1to Q3, Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 may each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, or any combination thereof, each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclyl, or C1-C 60 heterocyclyl; C7-C 60 aralkyl; or C2-C 60 heteroaralkyl.
[0684] As used herein, the term “heteroatom” can be any atom other than a carbon atom and a hydrogen atom. Examples of heteroatoms can include O, S, N, P, Si, B, Ge, Se, and any combination thereof.
[0685] As used herein, the term “first row transition metal” can be scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and zinc (Zn), and the like. As used herein, the term “second row transition metal” can be yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), and cadmium (Cd), and the like. Examples of the term “third row transition metal” as used herein can include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and gold (Au), and the like.
[0686] In the specification, the term “Ph” refers to phenyl, the term “Me” refers to methyl, the term “Et” refers to ethyl, the term “tert-Bu” or “Bu t ” each refers to a tert-butyl group, and the term “OMe” refers to methoxy.
[0687] As used herein, the term “biphenyl” can be “phenyl substituted with phenyl.” For example, “biphenyl” can be phenyl substituted with C6-C 60 aryl as a substituent.
[0688] The term "triphenyl" as used herein can be "phenyl substituted with biphenyl". For example, "triphenyl" can be phenyl having substituted with C6-C 60 C6-C 60 Phenyl substituted with aryl as a substituent.
[0689] Unless otherwise defined, the symbols *,'and " as used herein each refer to the bonding site to the adjacent atom in the corresponding formula or moiety.
[0690] In the specification, the terms "x-axis", "y-axis", and "z-axis" as used herein are not limited to three axes in an orthogonal coordinate system (e.g., a Cartesian coordinate system), and can be interpreted in a broader sense than the three axes in the aforementioned orthogonal coordinate system. For example, the x-axis, the y-axis, and the z-axis can describe axes orthogonal to each other, or can describe axes in different directions that are not orthogonal to each other.
[0691] In the specification, "an integer selected from 0 to 10" refers to an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10. The above description of the numerical range is equally applicable to any numerical range appearing in the specification, for example, an integer selected from 0 and 1, an integer selected from 0 to 2, an integer selected from 0 to 3, an integer selected from 0 to 4, an integer selected from 0 to 5, an integer selected from 0 to 6, an integer selected from 0 to 7, an integer selected from 0 to 8, an integer selected from 0 to 9, and an integer selected from 0 to 10, and the like.
[0692] Hereinafter, the compound and the light-emitting device according to the embodiments will be described in more detail with reference to synthesis examples and examples. The phrase "use B instead of A" used in the description of the synthesis examples refers to replacement of A with B in the same molar equivalent.
[0693] [Synthesis Examples and Examples]
[0694] Synthesis Example 1 (Compound BD01)
[0695] [Scheme 1]
[0696]
[0697] [Scheme 2]
[0698]
[0699] Synthesis of intermediate compound BD01-1
[0700] Intermediate compound BD01-1 (1.0 eq), phenylboronic acid (2.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3(2.0 eq) were dissolved in a solution containing tetrahydrofuran and H2O in a weight ratio of 4:1 (0.1 M), and the resulting reaction solution was stirred at 80 °C for 12 hours. The reaction mixture was subjected to a three-time extraction process using ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD01-2 (yield 90%).
[0701] Synthesis of intermediate compound BD01-2
[0702] Intermediate compound BD01-1 (1.0 eq), phenylboronic acid (2.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3(2.0 eq) were dissolved in a solution containing tetrahydrofuran and H2O in a weight ratio of 4:1 (0.1 M), and the resulting reaction solution was stirred at 80 °C for 12 hours. The reaction mixture was subjected to a three-time extraction process using ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD01-2 (yield 90%).
[0703] Synthesis of intermediate compound BD01-3
[0704] Intermediate compound BD01-2 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd2(dba)3(0.1 eq), SPhos (0.15 eq), and sodium tert-butoxide (4.0 eq) were dissolved in toluene (0.1 M), and the resulting reaction mixture was stirred at 120 °C for 12 hours. The reaction mixture was cooled at room temperature, filtered through celite using dichloromethane, and subjected to a three-time extraction process using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD01-3 (yield 78%).
[0705] Synthesis of intermediate compound BD01-4
[0706] Intermediate compound BD01-3 (1.0 eq), tin (3.0 eq), and HCl (12 M, 5.0 eq) were dissolved in ethanol (0.12 M), and the resulting reaction mixture was stirred at 80 °C for 12 hours. The reaction mixture was neutralized using NaOH and subjected to a three-time extraction process using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD01-4 (yield 75%).
[0707] Synthesis of intermediate compound BD01-5
[0708] Dissolve 2-methoxy-9H-carbazole (1.0 eq), 2-bromopyridine (1.2 eq), Pd2(dba)3 (0.02 eq), SPhos (0.04 eq) and NaOtBu (1.6 eq) in toluene (0.2 M) and stir the resulting reaction mixture at 110 °C for 12 hours. Perform a three-time extraction process on the reaction mixture by using ethyl acetate and water to obtain the organic layer. Dry the obtained organic layer using magnesium sulfate, concentrate and perform column chromatography to synthesize intermediate compound BD01-5 (yield 84%).
[0709] Synthesis of intermediate compound BD01-6
[0710] Dissolve intermediate compound BD01-5 (1.0 eq) in dichloromethane (0.1 M), add to it dropwise a solution of boron tribromide 1.0 M in dichloromethane (2.0 eq) at 0 °C and stir the resulting reaction mixture at room temperature for 5 hours. Neutralize the reaction mixture using NaOH and perform a three-time extraction process by using dichloromethane and water to obtain the organic layer. Dry the obtained organic layer using magnesium sulfate, concentrate and perform column chromatography to synthesize intermediate compound BD01-6 (yield 69%).
[0711] Synthesis of intermediate compound BD01-7
[0712] Dissolve intermediate compound BD01-6 (1.0 eq), 1-bromo-2-methoxybenzene (2.0 eq), CuI (0.2 eq), 2-picolinic acid (0.2 eq) and K3PO4 (2.0 eq) in dimethyl sulfoxide (0.15 M) and stir the resulting reaction mixture at 100 °C for 7 hours. Perform a three-time extraction process on the reaction mixture by using ethyl acetate and water to obtain the organic layer. Dry the obtained organic layer using magnesium sulfate, concentrate and perform column chromatography to synthesize intermediate compound BD01-7 (yield 60%).
[0713] Synthesis of intermediate compound BD01-8
[0714] Dissolve intermediate compound BD01-7 (1.0 eq) in dichloromethane (0.1 M), add to it dropwise a solution of boron tribromide 1.0 M in dichloromethane (2.0 eq) at 0 °C and stir the resulting reaction mixture at room temperature for 5 hours. Neutralize the reaction mixture using NaOH and perform a three-time extraction process by using dichloromethane and water to obtain the organic layer. Dry the obtained organic layer using magnesium sulfate, concentrate and perform column chromatography to synthesize intermediate compound BD01-8 (yield 55%).
[0715] Synthesis of intermediate compound BD01-9
[0716] Intermediate compound BD01-8 (1.0 eq), 1,3-dibromo benzene (2.0 eq), Cul (0.2 eq), 2-picolinic acid (0.2 eq) and K3PO4 (2.0 eq) were dissolved in dimethyl sulfoxide (0.15 M) and the resulting reaction mixture was stirred at 100 °C for 7 h. The reaction mixture was subjected to three extraction processes using ethyl acetate and water to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and subjected to column chromatography to synthesize intermediate compound BD01-9 (yield 64%).
[0717] Synthesis of intermediate compound BD01-10
[0718] Intermediate compound BD01-9 (1.0 eq), intermediate compound BD01-4 (1.3 eq), Pd2(dba)3 (0.05 eq), sodium tert-butoxide (2.0 eq) and XPhos (0.15 eq) were dissolved in 1,4-dioxane (0.1 M) and the resulting reaction mixture was stirred at 110 °C for 4 h. The reaction mixture was cooled at room temperature and subjected to three extraction processes using dichloromethane and water to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and subjected to column chromatography to synthesize intermediate compound BD01-10 (yield 87%).
[0719] Synthesis of intermediate compound BD01-11
[0720] Intermediate compound BD01-10 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq) and the resulting reaction mixture was stirred at 80 °C for 12 h. The reaction mixture was subjected to three extraction processes using dichloromethane and water to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and subjected to column chromatography to synthesize intermediate compound BD01-11 (yield 89%).
[0721] Synthesis of compound BD01
[0722] Intermediate compound BD01-11 (1.0 eq), K2PtCl4 (1.1 eq) and 2,6-dimethylpyridine (4.0 eq) were dissolved in o-dichlorobenzene (o-DCB) (0.05 M) and the resulting reaction mixture was stirred at 120 °C for 12 h. The reaction mixture was cooled at room temperature and subjected to Si filtration using dichloromethane and n-hexane to remove o-DCB therefrom to synthesize compound BD01 (yield 55%).
[0723] Synthesis Example 2 (Compound BD52) [Scheme 1]
[0724]
[0725] [Scheme 2]
[0726]
[0727]
[0728] Synthesis of intermediate compound BD52-1
[0729] Dissolved 2,6-dibromoaniline (2.0 eq), (phenyl-d5)boronic acid (1.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3(2.0 eq) in a solution (0.1 M) containing tetrahydrofuran and H2O in a weight ratio of 4:1, and the resulting reaction solution was stirred at 80°C for 12 hours. The reaction mixture was subjected to a three-time extraction process using ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD52-1 (yield 75%).
[0730] Synthesis of intermediate compound BD52-2
[0731] Dissolved intermediate compound BD52-1 (1.0 eq), (3,5-di-tert-butylphenyl)boronic acid (2.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3(2.0 eq) in a solution (0.1 M) containing tetrahydrofuran and H2O in a weight ratio of 4:1, and the resulting reaction solution was stirred at 80°C for 12 hours. The reaction mixture was subjected to a three-time extraction process using ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD52-2 (yield 96%).
[0732] Synthesis of intermediate compound BD52-3
[0733] Dissolved intermediate compound BD52-2 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd2(dba)3(0.1 eq), SPhos (0.15 eq), and sodium tert-butoxide (4.0 eq) in toluene (0.1 M), and the resulting reaction mixture was stirred at 120°C for 12 hours. The reaction mixture was cooled at room temperature, filtered through diatomite by using dichloromethane, and subjected to a three-time extraction process using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD52-3 (yield 81%).
[0734] Synthesis of intermediate compound BD52-4
[0735] Intermediate compound BD52-3 (1.0 eq), tin (3.0 eq) and HCI (12 M, 5.0 eq) were dissolved in ethanol (0.12 M) and the resulting reaction mixture was stirred at 80 °C for 12 hours. The reaction mixture was neutralized using NaOH and a three-time extraction process using dichloromethane and water was performed to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD52-4 (yield 79%).
[0736] Synthesis of intermediate compound BD52-5
[0737] 2-Methoxy-9H-carbazole (1.0 eq), 2-bromo-4-(tert-butyl)pyridine (1.2 eq), Pd2(dba)3 (0.02 eq), SPhos (0.04 eq) and NaOtBu (1.6 eq) were dissolved in toluene (0.2 M) and the resulting reaction mixture was stirred at 110 °C for 12 hours. A three-time extraction process using ethyl acetate and water was performed on the reaction mixture to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD52-5 (yield 81%).
[0738] Synthesis of intermediate compound BD52-6
[0739] Intermediate compound BD52-5 (1.0 eq) was dissolved in dichloromethane (0.1 M) and to this, a solution of boron tribromide 1.0 M in dichloromethane (2.0 eq) was added dropwise at 0 °C and the resulting reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was neutralized using NaOH and a three-time extraction process using dichloromethane and water was performed to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD52-6 (yield 70%).
[0740] Synthesis of intermediate compound BD52-7
[0741] Intermediate compound BD52-6 (1.0 eq), 2-bromo-5-(tert-butyl)-l-methoxybenzene (2.0 eq), Cul (0.2 eq), 2-picolinic acid (0.2 eq), and K3PO4 (2.0 eq) were dissolved in dimethyl sulfoxide (0.15 M), and the resulting reaction mixture was stirred at 100 °C for 7 hours. The reaction mixture was subjected to a three-time extraction process using ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD52-7 (yield 66%).
[0742] Synthesis of intermediate compound BD52-8
[0743] Intermediate compound BD52-7 (1.0 eq) was dissolved in dichloromethane (0.1 M), to which a solution of boron tribromide 1.0 M in dichloromethane (2.0 eq) was added dropwise at 0 °C, and the resulting reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was neutralized using NaOH, and subjected to a three-time extraction process using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD52-8 (yield 53%).
[0744] Synthesis of intermediate compound BD52-9
[0745] Intermediate compound BD52-8 (1.0 eq), 1,3-dibromo benzene (2.0 eq), Cul (0.2 eq), 2-picolinic acid (0.2 eq), and K3PO4 (2.0 eq) were dissolved in dimethyl sulfoxide (0.15 M), and the resulting reaction mixture was stirred at 100 °C for 7 hours. The reaction mixture was subjected to a three-time extraction process using ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD52-9 (yield 61%).
[0746] Synthesis of intermediate compound BD52-10
[0747] Intermediate compound BD52-9 (1.0 eq), intermediate compound BD52-4 (1.3 eq), Pd2(dba)3 (0.05 eq), sodium tert-butoxide (2.0 eq), and XPhos (0.15 eq) were dissolved in 1,4-dioxane (0.1 M), and the resulting reaction mixture was stirred at 110 °C for 4 hours. The reaction mixture was cooled at room temperature, and subjected to a three-time extraction process using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD52-10 (yield 78%).
[0748] Synthesis of intermediate compound BD52-11
[0749] Intermediate compound BD52-10 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq) and the resulting reaction mixture was stirred at 80 °C for 12 hours. A three-time extraction process was performed on the reaction mixture by using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and column chromatography was performed to synthesize intermediate compound BD52-11 (yield 88%).
[0750] Synthesis of compound BD52
[0751] Intermediate compound BD52-11 (1.0 eq), K2PtCl4 (1.1 eq), and 2,6-dimethylpyridine (4.0 eq) were dissolved in o-DCB (0.05 M) and the resulting reaction mixture was stirred at 120 °C for 12 hours. The reaction mixture was cooled at room temperature and Si filtration was performed using dichloromethane and n-hexane to remove o-DCB therefrom to synthesize compound BD52 (yield 52%).
[0752] Synthesis Example 3 (compound BD58)
[0753] [Scheme 1]
[0754]
[0755]
[0756] [Scheme 2]
[0757]
[0758] Synthesis of intermediate compound BD58-1
[0759] 2,6-Dibromoaniline (2.0 eq), (phenyl-d5)boronic acid (1.0 eq), Pd(PPh3)4 (0.05 eq), and K2CO3 (2.0 eq) were dissolved in a solution containing tetrahydrofuran and H2O in a weight ratio of 4:1 (0.1 M) and the resulting reaction solution was stirred at 80 °C for 12 hours. A three-time extraction process was performed on the reaction mixture by using ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and column chromatography was performed to synthesize intermediate compound BD58-1 (yield 75%).
[0760] Synthesis of intermediate compound BD58-2
[0761] Intermediate compound BD58-1 (1.0 eq), (3,5-di-tert-butylphenyl)boronic acid (2.0 eq), Pd(PPh3)4(0.05 eq), and K2CO3(2.0 eq) were dissolved in a solution containing a 4:1 weight ratio of tetrahydrofuran and H2O (0.1 M), and the resulting reaction solution was stirred at 80 °C for 12 hours. A three-time extraction process was performed on the reaction mixture by using ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and column chromatography was performed, thereby synthesizing intermediate compound BD58-2 (yield 96%).
[0762] Synthesis of intermediate compound BD58-3
[0763] Intermediate compound BD58-2 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd2(dba)3(0.1 eq), SPhos (0.15 eq), and sodium tert-butoxide (4.0 eq) were dissolved in toluene (0.1 M), and the resulting reaction mixture was stirred at 120 °C for 12 hours. The reaction mixture was cooled at room temperature, filtered through diatomite by using dichloromethane, and a three-time extraction process was performed by using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and column chromatography was performed, thereby synthesizing intermediate compound BD58-3 (yield 81%).
[0764] Synthesis of intermediate compound BD58-4
[0765] Intermediate compound BD58-3 (1.0 eq), tin (3.0 eq), and HCl (12 M, 5.0 eq) were dissolved in ethanol (0.12 M), and the resulting reaction mixture was stirred at 80 °C for 12 hours. The reaction mixture was neutralized using NaOH, and a three-time extraction process was performed by using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and column chromatography was performed, thereby synthesizing intermediate compound BD58-4 (yield 79%).
[0766] Synthesis of intermediate compound BD58-5
[0767] 2-Methoxy-9H-carbazole (1.0 eq), 2-bromopyridine (1.2 eq), Pd2(dba)3(0.02 eq), SPhos (0.04 eq), and NaOtBu (1.6 eq) were dissolved in toluene (0.2 M), and the resulting reaction mixture was stirred at 110 °C for 12 hours. A three-time extraction process was performed on the reaction mixture by using ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and column chromatography was performed, thereby synthesizing intermediate compound BD58-5 (yield 84%).
[0768] Synthesis of intermediate compound BD58-6
[0769] Intermediate compound BD58-5 (1.0 eq) was dissolved in dichloromethane (0.1 M) to which a solution of boron tribromide 1.0 M in dichloromethane (2.0 eq) was added dropwise at 0 °C and the resulting reaction mixture was stirred at room temperature for 5 h. The reaction mixture was neutralized using NaOH and a three-time extraction process using dichloromethane and water was performed to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD58-6 (yield 69%).
[0770] Synthesis of intermediate compound BD58-7
[0771] Intermediate compound BD58-6 (1.0 eq), 3-bromo-4-methoxybenzonitrile (2.0 eq), CuI (0.2 eq), 2-picolinic acid (0.2 eq) and K3PO4 (2.0 eq) were dissolved in dimethyl sulfoxide (0.15 M) and the resulting reaction mixture was stirred at 100 °C for 7 h. A three-time extraction process using ethyl acetate and water was performed on the reaction mixture to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD58-7 (yield 64%).
[0772] Synthesis of intermediate compound BD58-8
[0773] Intermediate compound BD58-7 (1.0 eq) was dissolved in dichloromethane (0.1 M) to which a solution of boron tribromide 1.0 M in dichloromethane (2.0 eq) was added dropwise at 0 °C and the resulting reaction mixture was stirred at room temperature for 5 h. The reaction mixture was neutralized using NaOH and a three-time extraction process using dichloromethane and water was performed to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD58-8 (yield 59%).
[0774] Synthesis of intermediate compound BD58-9
[0775] Intermediate compound BD58-8 (1.0 eq), 1,3-dibromo benzene (2.0 eq), CuI (0.2 eq), 2-picolinic acid (0.2 eq) and K3PO4 (2.0 eq) were dissolved in dimethyl sulfoxide (0.15 M) and the resulting reaction mixture was stirred at 100 °C for 7 h. A three-time extraction process using ethyl acetate and water was performed on the reaction mixture to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD58-9 (yield 61%).
[0776] Synthesis of intermediate compound BD58-10
[0777] Intermediate compound BD58-9 (1.0 eq), intermediate compound BD58-4 (1.3 eq), Pd2(dba)3 (0.05 eq), sodium tert-butoxide (2.0 eq), and XPhos (0.15 eq) were dissolved in 1,4-dioxane (0.1 M), and the resulting reaction mixture was stirred at 110 °C for 4 hours. The reaction mixture was cooled at room temperature, and an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and column chromatography was performed, thereby synthesizing intermediate compound BD58-10 (yield 84%).
[0778] Synthesis of intermediate compound BD58-11
[0779] Intermediate compound BD58-10 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq), and the resulting reaction mixture was stirred at 80 °C for 12 hours. An extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and column chromatography was performed, thereby synthesizing intermediate compound BD58-11 (yield 91%).
[0780] Synthesis of compound BD58
[0781] Intermediate compound BD58-11 (1.0 eq), K2PtCl4 (1.1 eq), and 2,6-dimethylpyridine (4.0 eq) were dissolved in o-DCB (0.05 M), and the resulting reaction mixture was stirred at 120 °C for 12 hours. The reaction mixture was cooled at room temperature, and Si filtration was performed using dichloromethane and n-hexane to remove o-DCB therefrom, thereby synthesizing compound BD58 (yield 56%).
[0782] Synthesis Example 4 (compound BD71) [Scheme 1]
[0783]
[0784] [Scheme 2]
[0785]
[0786] Synthesis of intermediate compound BD71-1
[0787] Intermediate compound BD71-1 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd2(dba)3 (0.1 eq), SPhos (0.15 eq), and sodium tert-butoxide (4.0 eq) were dissolved in toluene (0.1 M), and the resulting reaction mixture was stirred at 120 °C for 12 hours. The reaction mixture was cooled at room temperature, filtered through celite by using dichloromethane, and subjected to a three-time extraction process by using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD71-2 (yield 85%).
[0788] Synthesis of intermediate compound BD71-2
[0789] Intermediate compound BD71-1 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd2(dba)3 (0.1 eq), SPhos (0.15 eq), and sodium tert-butoxide (4.0 eq) were dissolved in toluene (0.1 M), and the resulting reaction mixture was stirred at 120 °C for 12 hours. The reaction mixture was cooled at room temperature, filtered through celite by using dichloromethane, and subjected to a three-time extraction process by using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD71-2 (yield 85%).
[0790] Synthesis of intermediate compound BD71-3
[0791] Intermediate compound BD71-2 (1.0 eq), tin (3.0 eq), and HCl (12 M, 5.0 eq) were dissolved in ethanol (0.12 M), and the resulting reaction mixture was stirred at 80 °C for 12 hours. The reaction mixture was neutralized using NaOH and subjected to a three-time extraction process by using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD71-3 (yield 87%).
[0792] Synthesis of intermediate compound BD71-4
[0793] 2-Methoxy-9H-carbazole (1.0 eq), 2-bromo-4-(tert-butyl)pyridine (1.2 eq), Pd2(dba)3 (0.02 eq), SPhos (0.04 eq), and NaOtBu (1.6 eq) were dissolved in toluene (0.2 M), and the resulting reaction mixture was stirred at 110 °C for 12 hours. The reaction mixture was subjected to a three-time extraction process by using ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD71-4 (yield 81%).
[0794] Synthesis of intermediate compound BD71-5
[0795] Intermediate compound BD71-4 (1.0 eq) was dissolved in dichloromethane (0.1 M) to which a solution of boron tribromide 1.0 M in dichloromethane (2.0 eq) was added dropwise at 0 °C and the resulting reaction mixture was stirred at room temperature for 5 h. The reaction mixture was neutralized using NaOH and a three-time extraction process using dichloromethane and water was performed to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD71-5 (yield 71%).
[0796] Synthesis of intermediate compound BD71-6
[0797] Intermediate compound BD71-5 (1.0 eq), 6-bromo-7-methoxy-1,2,3,4- tetrahydronaphthalene (2.0 eq), CuI (0.2 eq), 2-picolinic acid (0.2 eq) and K3PO4 (2.0 eq) were dissolved in dimethyl sulfoxide (0.15 M) and the resulting reaction mixture was stirred at 100 °C for 7 h. A three-time extraction process using ethyl acetate and water was performed on the reaction mixture to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD71-6 (yield 65%).
[0798] Synthesis of intermediate compound BD71-7
[0799] Intermediate compound BD71-6 (1.0 eq) was dissolved in dichloromethane (0.1 M) to which a solution of boron tribromide 1.0 M in dichloromethane (2.0 eq) was added dropwise at 0 °C and the resulting reaction mixture was stirred at room temperature for 5 h. The reaction mixture was neutralized using NaOH and a three-time extraction process using dichloromethane and water was performed to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD71-7 (yield 56%).
[0800] Synthesis of intermediate compound BD71-8
[0801] Intermediate compound BD71-7 (1.0 eq), 1,3-dibromo benzene (2.0 eq), CuI (0.2 eq), 2-picolinic acid (0.2 eq) and K3PO4 (2.0 eq) were dissolved in dimethyl sulfoxide (0.15 M) and the resulting reaction mixture was stirred at 100 °C for 7 h. A three-time extraction process using ethyl acetate and water was performed on the reaction mixture to obtain the organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD71-8 (yield 63%).
[0802] Synthesis of intermediate compound BD71-9
[0803] Intermediate compound BD71-8 (1.0 eq), intermediate compound BD71-3 (1.3 eq), Pd2(dba)3 (0.05 eq), sodium tert-butoxide (2.0 eq), and XPhos (0.15 eq) were dissolved in 1,4-dioxane (0.1 M), and the resulting reaction mixture was stirred at 110 °C for 4 hours. The reaction mixture was cooled at room temperature, and a three-time extraction process was performed using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and column chromatography was performed, thereby synthesizing intermediate compound BD71-9 (yield 79%).
[0804] Synthesis of intermediate compound BD71-10
[0805] Intermediate compound BD71-9 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq), and the resulting reaction mixture was stirred at 80 °C for 12 hours. A three-time extraction process was performed on the reaction mixture using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and column chromatography was performed, thereby synthesizing intermediate compound BD71-10 (yield 89%).
[0806] Synthesis of compound BD71
[0807] Intermediate compound BD71-10 (1.0 eq), K2PtCl4 (1.1 eq), and 2,6-dimethylpyridine (4.0 eq) were dissolved in o-DCB (0.05 M), and the resulting reaction mixture was stirred at 120 °C for 12 hours. The reaction mixture was cooled at room temperature, and Si filtration was performed using dichloromethane and n-hexane to remove o-DCB therefrom, thereby synthesizing compound BD71 (yield 53%).
[0808] Synthesis Example 5 (compound BD86)
[0809] [Scheme 1]
[0810]
[0811] [Scheme 2]
[0812]
[0813] Synthesis of intermediate compound BD86-1
[0814] Intermediate compound BD86-1 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd2(dba)3 (0.1 eq), SPhos (0.15 eq), and sodium tert-butoxide (4.0 eq) were dissolved in toluene (0.1 M), and the resulting reaction mixture was stirred at 120 °C for 12 h. The reaction mixture was cooled at room temperature, filtered through celite by using dichloromethane, and subjected to a three-time extraction process by using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD86-2 (yield 80%).
[0815] Synthesis of intermediate compound BD86-2
[0816] Intermediate compound BD86-1 (1.0 eq), 1-bromo-2-nitrobenzene (1.5 eq), Pd2(dba)3 (0.1 eq), SPhos (0.15 eq), and sodium tert-butoxide (4.0 eq) were dissolved in toluene (0.1 M), and the resulting reaction mixture was stirred at 120 °C for 12 h. The reaction mixture was cooled at room temperature, filtered through celite by using dichloromethane, and subjected to a three-time extraction process by using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD86-2 (yield 80%).
[0817] Synthesis of intermediate compound BD86-3
[0818] Intermediate compound BD86-2 (1.0 eq), tin (3.0 eq), and HC1 (12 M, 5.0 eq) were dissolved in ethanol (0.12 M), and the resulting reaction mixture was stirred at 80 °C for 12 h. The reaction mixture was neutralized using NaOH and subjected to a three-time extraction process by using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD86-3 (yield 84%).
[0819] Synthesis of intermediate compound BD86-4
[0820] 2-Methoxy-9H-carbazole (1.0 eq), 2-bromopyridine (1.2 eq), Pd2(dba)3 (0.02 eq), SPhos (0.04 eq), and NaOtBu (1.6 eq) were dissolved in toluene (0.2 M), and the resulting reaction mixture was stirred at 110 °C for 12 h. The reaction mixture was subjected to a three-time extraction process by using ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and subjected to column chromatography, thereby synthesizing intermediate compound BD86-4 (yield 84%).
[0821] Synthesis of intermediate compound BD86-5
[0822] Intermediate compound BD86-4 (1.0 eq) was dissolved in dichloromethane (0.1 M) to which a solution of boron tribromide 1.0 M in dichloromethane (2.0 eq) was added dropwise at 0 °C and the resulting reaction mixture was stirred at room temperature for 5 h. The reaction mixture was neutralized using NaOH and an organic layer was obtained by performing a three-time extraction process using dichloromethane and water. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD86-5 (yield 67%).
[0823] Synthesis of intermediate compound BD86-6
[0824] Intermediate compound BD86-5 (1.0 eq), 1-bromo-2-methoxynaphthalene (2.0 eq), CuI (0.2 eq), 2-picolinic acid (0.2 eq) and K3PO4 (2.0 eq) were dissolved in dimethyl sulfoxide (0.15 M) and the resulting reaction mixture was stirred at 100 °C for 7 h. An organic layer was obtained by performing a three-time extraction process using ethyl acetate and water. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD86-6 (yield 61%).
[0825] Synthesis of intermediate compound BD86-7
[0826] Intermediate compound BD86-6 (1.0 eq) was dissolved in dichloromethane (0.1 M) to which a solution of boron tribromide 1.0 M in dichloromethane (2.0 eq) was added dropwise at 0 °C and the resulting reaction mixture was stirred at room temperature for 5 h. The reaction mixture was neutralized using NaOH and an organic layer was obtained by performing a three-time extraction process using dichloromethane and water. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD86-7 (yield 57%).
[0827] Synthesis of intermediate compound BD86-8
[0828] Intermediate compound BD86-7 (1.0 eq), 1,3-dibromobenzene (2.0 eq), CuI (0.2 eq), 2-picolinic acid (0.2 eq) and K3PO4 (2.0 eq) were dissolved in dimethyl sulfoxide (0.15 M) and the resulting reaction mixture was stirred at 100 °C for 7 h. An organic layer was obtained by performing a three-time extraction process using ethyl acetate and water. The obtained organic layer was dried using magnesium sulfate, concentrated and column chromatography was performed to synthesize intermediate compound BD86-8 (yield 62%).
[0829] Synthesis of intermediate compound BD86-9
[0830] Intermediate compound BD86-8 (1.0 eq), intermediate compound BD86-3 (1.3 eq), Pd2(dba)3 (0.05 eq), sodium tert-butoxide (2.0 eq), and XPhos (0.15 eq) were dissolved in 1,4-dioxane (0.1 M), and the resulting reaction mixture was stirred at 110°C for 4 hours. The reaction mixture was cooled at room temperature, and an extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and column chromatography was performed, thereby synthesizing intermediate compound BD86-9 (yield 81%).
[0831] Synthesis of intermediate compound BD86-10
[0832] Intermediate compound BD86-9 (1.0 eq) and triethyl orthoformate (50.0 eq) were dissolved in HCl (35%, 1.2 eq), and the resulting reaction mixture was stirred at 80°C for 12 hours. An extraction process was performed three times using dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate, concentrated, and column chromatography was performed, thereby synthesizing intermediate compound BD86-10 (yield 90%).
[0833] Synthesis of compound BD86
[0834] Intermediate compound BD86-10 (1.0 eq), K2PtCl4 (1.1 eq), and 2,6-dimethylpyridine (4.0 eq) were dissolved in o-DCB (0.05 M), and the resulting reaction mixture was stirred at 120°C for 12 hours. The reaction mixture was cooled at room temperature, and Si filtration was performed using dichloromethane and n-hexane to remove o-DCB therefrom, thereby synthesizing compound BD86 (yield 54%).
[0835] For the compounds synthesized in Synthesis Example 1 to Synthesis Example 5, H NMR and high resolution mass (HR-MS) were measured, and the results are shown in Table 1. By referring to the synthesis path and raw materials, a person skilled in the art can easily identify the synthesis method of a compound other than the compounds synthesized in Synthesis Example 1 to Synthesis Example 5. 1 H NMR and high resolution mass (HR-MS) were measured, and the results are shown in Table 1. By referring to the synthesis path and raw materials, a person skilled in the art can easily identify the synthesis method of a compound other than the compounds synthesized in Synthesis Example 1 to Synthesis Example 5.
[0836] [Table 1]
[0837]
[0838]
[0839] [Assessment Example 1]
[0840] The LUMO level, HOMO level, and band gap of the compounds in the synthetic and comparative examples were measured using the methods described in Table 2, and the results are shown in Table 3.
[0841] [Table 2]
[0842]
[0843] [Table 3]
[0844] Compound HOMO level (eV) LUMO level (eV) Band gap (eV) Synthesis Example 1 -5.66 -2.06 3.60 Synthesis Example 2 -5.63 -2.05 3.58 Synthesis Example 3 -5.85 -2.19 3.66 Synthesis Example 4 -5.64 -1.92 3.72 Synthesis Example 5 -5.67 -2.08 3.59 Comparative Compound 1 -5.38 -2.00 3.38 Comparative Compound 2 -5.88 -2.33 3.55
[0845] [Comparative Compound 1]
[0846]
[0847] [Comparative Compound 2]
[0848]
[0849] [Example 1]
[0850] As the anode, Corning 15Ω / cm 2 The ITO glass substrate was cut to a size of 50mm × 50mm × 0.7mm, ultrasonicated with isopropanol and pure water for 5 minutes each, and cleaned by exposure to ultraviolet light and ozone for 30 minutes. The ITO glass substrate was then fed into a vacuum deposition apparatus.
[0851] 2-TNATA is deposited on an ITO anode formed on a glass substrate to form a structure with... A hole injection layer of a certain thickness is formed, and NPB is deposited on the hole injection layer to form a hole injection layer with [missing information]. A hole transport layer of a certain thickness.
[0852] Compounds ETH2 and HTH29 (as the main components) and compound BD01 (as a dopant) were co-deposited on the hole transport layer in a weight ratio of 5:5 to form a structure with... The thickness of the emission layer.
[0853] Alq3 was deposited on the emitter layer to form a structure with... An electron transport layer of a certain thickness is formed by depositing LiF on the electron transport layer to create an electron transport layer with... An electron-injected layer of a certain thickness was formed, and Al was vacuum-deposited onto the electron-injected layer to form a layer with [missing information]. The LiF / Al electrode (cathode) of a certain thickness is used to complete the fabrication of the light-emitting device.
[0854]
[0855] [Examples 2 to 5, Comparative Example 1 and Comparative Example 2]
[0856] The light-emitting devices of Examples 2 to 5, Comparative Example 1 and Comparative Example 2 were manufactured in substantially the same manner as in Example 1, except that compounds BD52, BD58, BD71, BD86, Comparative Example Compound 1 and Comparative Example Compound 2 were used instead of compound BD01 in Example 1.
[0857] [Evaluation Example 2]
[0858] To evaluate the characteristics of the light-emitting devices manufactured according to Examples 1 to 5, Comparative Example 1, and Comparative Example 2, measurements were taken at 10 mA / cm². 2 The driving voltage and maximum emission wavelength at the current density were determined, and the results are shown in Table 4. The driving voltage of the light-emitting device was measured using a source meter (Keithley Instrument, Inc., 2400 series), and the maximum emission wavelength was measured using a Hamamatsu Quantaurus-QY Absolute PL quantum yield spectrometer (equipped with a xenon light source, monochromator, photon multichannel analyzer, and integrating sphere, and using PLQY measurement software (Hamamatsu Optoelectronics Co., Ltd., Shizuoka, Japan)). During the measurement, the excitation wavelength was scanned from 320 nm to 380 nm at 10 nm intervals, and the spectrum measured at an excitation wavelength of 340 nm was used to obtain the maximum emission wavelength (emission peak wavelength) for each compound. The results are summarized in Table 4. To measure the device lifetime (T... 90 , h), calculate the time required to reach 90% of the initial brightness.
[0859] [Table 4]
[0860]
[0861]
[0862] [Comparative Compound 1]
[0863]
[0864] [Comparative Compound 2]
[0865]
[0866] According to Table 4, it can be seen that, compared with the light-emitting devices of Comparative Example 1 and Comparative Example 2, the light-emitting devices of Examples 1 to 5 have better device characteristics by exhibiting improved lifespan and color purity.
[0867] The use of the organic metal compound can ensure the manufacture of a light emitting device having high color purity and a short maximum emission wavelength, and a high-quality electronic device and electronic equipment including the light emitting device.
[0868] Embodiments have been disclosed herein and, although the terms are employed in the description, they are used in a generic and descriptive sense only and not for purposes of limitation, unless otherwise specifically indicated. In some instances, features, characteristics or elements described in connection with an embodiment can be used alone or in combination with features, characteristics or elements described in connection with other embodiments, unless otherwise specifically indicated. Accordingly, one of ordinary skill in the art will recognize that various changes can be made without departing from the spirit and scope of the disclosure.
Claims
1. A light-emitting device comprising: a first electrode; a second electrode facing the first electrode; a sandwich layer between the first electrode and the second electrode and including an emissive layer; and an organometallic compound represented by Formula 1: Formula 1 wherein in Formula 1, M is platinum, iridium, palladium, cobalt, gold, nickel, silver, or copper, X1to X4are each independently C or N, CY1to CY5are each independently C3-C 60 carbocyclyl or C1-C 60 heterocyclyl, T1and T2are each independently N(R6), C(R6)(R7), Si(R6)(R7), S, or O, L1and L2are each independently a single bond, *-N(R8)-*, *-B(R8)-*, *-P(R8)-*, *-C(R8)(R9)-*, *-Si(R8)(R9)-*, *-Ge(R8)(R9)-*, *-S-*', *-Se-*', *-O-*', *-C(=O)-*, *-S(=O)-*, *-S(=O)2-*', or *-C(=S)-*, a1to a5are each independently an integer selected from 0 to 10, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, or a nitro group; R1 to R9 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic group, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C7-C 60 Aryl, unsubstituted or with at least one R 10a Replacement C2-C 60 Heteroalkyl groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), R 10a is:
2. The light-emitting device according to claim 1, wherein Each of the following C1-C that is not substituted or is substituted: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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 of the following C3-Cs that are not substituted or are substituted: 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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 ), and Q1to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently: hydrogen; deuterium; -F; -CI; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, or any combination thereof, unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclyl, or C1-C 60 heterocyclyl; C7-C 60 aralkyl; or C2-C 60 heteroaralkyl. the first electrode is an anode, the second electrode is a cathode, the sandwich layer further includes: a hole transport region between the first electrode and the emissive layer; and an electron transport region between the emissive layer and the second electrode, the hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
3. The light-emitting device according to claim 1, wherein the sandwich layer includes the organometallic compound.
4. The light-emitting device according to claim 1, wherein the emissive layer includes the organometallic compound.
5. The light-emitting device according to claim 1, wherein the emissive layer includes a host and a dopant, and the dopant includes the organometallic compound.
6. An electronic device including the light-emitting device according to any one of claims 1 to 5.
7. The electronic device according to claim 6, further comprising: a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
8. An electronic equipment including the light-emitting device according to any one of claims 1 to 5. 9.The electronic device of claim 8, wherein the electronic device is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a full transparent display, a partial transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet computer, a phablet computer, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional display, a virtual reality display, an augmented reality display, a vehicle, a video wall having a plurality of displays spliced together, a theater screen, a stadium screen, a light therapy device, or a signboard. 10.An organometallic compound represented by formula 1: Formula 1 wherein in formula 1, M is platinum, iridium, palladium, cobalt, gold, nickel, silver, or copper, CY1to CY5are each independently C3-C 60 carbocyclyl or C1-C 60 heterocyclyl, X 1 to X 4 are each independently C or N, T 1 and T 2 are each independently N(R 6), C(R 6)(R 7), Si(R 6)(R 7), S, or O, L 1 and L 2 are each independently a single bond, *-N(R 8)-*, *-B(R 8)-*, *-P(R 8)-*, *-C(R 8)(R 9)-*, *-Si(R 8)(R 9)-*, *-Ge(R 8)(R 9)-*, *-S-**, *-Se-**, *-O-**, *-C(=O)-*, *-S(=O)-*, *-S(=O) 2-**, or *-C(=S)-*, a 1 to a 5 are each independently an integer selected from 0 to 10, R1 to R9 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic group, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C7-C 60 Aryl, unsubstituted or with at least one R 10a Replacement C2-C 60 Heteroalkyl groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), R 10a is: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, or a nitro group; Each of the following C1-C that is not substituted or is substituted: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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 of the following C3-Cs that are not substituted or are substituted: 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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 ), and Q1to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently: hydrogen; deuterium; -F; -CI; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, or any combination thereof, unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclyl, or C1-C 60 heterocyclyl; C7-C 60 aralkyl; or C2-C 60 heteroaralkyl. 11.The organometallic compound of claim 10, wherein formula 1 includes deuterium, a cyano group, a carbazolyl group, a tert-butyl group, or any combination thereof. 12.The organometallic compound of claim 10, wherein in formula 1, a cyclometallating group including M, X 2, T 1, T 2, and X 3 has a ring structure of 9 or more members.
13. The organometallic compound according to claim 10, wherein CY1 to CY5 are each independently cyclopentadienyl, adamantyl, norbornyl, phenyl, pentalenyl, naphthyl, azulene, indacenyl, acenaphthyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzo phenanthryl, perylenyl, pentaphenyl, heptalene, tetracene, coronene, ovalene, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl, indenoanthracenyl, tetrahydronaphthyl, pyrrolyl, thiophenyl, furanyl, indolyl, benzoindolyl, naphthoindolyl, isoindolyl, benzoisoindolyl, naphthoisoindolyl, benzothiazolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiazolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothienocarbazolyl, benzothiazolocarbazolyl, benzoindolocarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzonaphthothiazolyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, benzothienodibenzothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, indazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinoxalyl, benzoquinoxalyl, quinazolyl, benzoquinazolyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthpyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafuorenyl, azadibenzothiazolyl, azadibenzothiophenyl, or azadibenzofuranyl.
14. The organometallic compound according to claim 10, wherein the moiety represented by ###0000072### in formula 1 is a moiety represented by formula 2: ###0000073### ###0000074### Formula 2 wherein in Formula 2, X1 is the same as defined in Formula 1, R 11 and R 12 each independently is the same as defined above for R1in formula 1, CY 11 the same as defined with reference to CY1 in formula 1, a11 is an integer selected from 0 to 10, * indicates a binding site with M, and * indicates a binding site with L1.
15. The organometallic compound of claim 14, wherein R 12 is a group represented by formula 6: Formula 6 wherein in Formula 6, R 61 to R 64 each independently the same as defined with reference to R1in Formula 1, a61 and a62 are each independently an integer selected from 1 to 5, a63 is an integer selected from 1 to 3, a64 is an integer selected from 1 to 4, b1 is an integer selected from 0 to 10, and * indicates a binding site with an adjacent atom.
16. The organometallic compound according to claim 10, wherein in formula 1, by The part represented is the part represented by Equation 3: Formula 3 wherein in Formula 3, X2 is the same as defined in Formula 1, Y 21 and Y 22 each independently C or N, Y 23 is C(R 23 ) or N, Y 24 is C(R 24 ) or N, Y 25 is C(R 25 ) or N, R 23 to R 25 each is the same as defined with reference to R2in Formula 1, * indicates a binding site with L1, * indicates a binding site with M, and * indicates a binding site with T1.
17. The organometallic compound of claim 10, wherein the moiety represented by ###0000441### in Formula 1 is a moiety represented by Formula 4: ###0000442### Formula 4 Formula 4 Formula 4 wherein in Formula 4, X3 is the same as defined in Formula 1, CY 31 and CY 32 each independently the same as defined with reference to CY3in Formula 1, T3is a single bond, N(R 33 ), C(R 33 )(R 34 ), Si(R 33 )(R 34 ), S, or O, R 31 to R 34 each independently the same as defined with reference to R3in Formula 1, a31 and a32 are each independently an integer selected from 0 to 10, * indicates a binding site with L2, * indicates a binding site with M, and * indicates a binding site with T2.
18. The organometallic compound of claim 10, wherein the moiety represented by ###0000465### in Formula 1 is a moiety represented by Formula 5: ###0000466### Formula 5 Formula 5 Formula 5 wherein in Formula 5, X4 is the same as defined in Formula 1, Y 41 is C or N, Y 42 is C(R 42 ) or N, Y 43 is C(R 43 ) or N, Y 44 is C(R 44 ) or N, Y 45 is C(R 45 ) or N, R 42 to R 45 each is the same as defined with reference to R4in Formula 1, * indicates a binding site with M, and * indicates a binding site with L2.
19. The organometallic compound according to claim 10, wherein the moiety represented by in formula 1 is a moiety represented by one of formulae 6-1 to 6-6: 6-1 6-2 6-3 6-4 6-5 6-6 wherein in Formulae 6-1 to 6-6, Y 51 is C(R 51 ) or N, Y 52 is C(R 52 ) or N, Y 53 is C(R 53 ) or N, Y 54 is C(R 54 ) or N, Y 55 is C(R 55 ) or N, Y 56 is C(R 56 ) or N, Y 57 is C(R 57 ) or N, Y 58 is C(R 58 ) or N, R 51 to R 59 each independently the same as defined with reference to R5in Formula 1, a59 is an integer selected from 0 to 8, and a60 is an integer selected from 0 to 8. * and * each separately indicate a binding site to T1 or T2.
20. The organometallic compound of claim 10, wherein the organometallic compound is one of Compound BD01 to Compound BD112: In Compound BD01 to Compound BD112, M is Pt.
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System and method to support AI-based interactive services for home appliances
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