Light-emitting device including organometallic compound, electronic device including light-emitting device, electronic equipment including light-emitting device, and organometallic compound
By introducing an organometallic compound represented by Formula 1 as the emission layer material in the light-emitting device, the limitations of brightness and response speed in the prior art are solved, achieving more efficient carrier recombination and lower driving voltage, thus improving the light-emitting performance.
Patent Information
- Application Number
- CN202510982846.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-07-16
- Filing Date
- 2025-07-16
- Publication Date
- 2026-01-16
AI Technical Summary
Existing light-emitting devices have limitations in improving brightness, driving voltage, and response speed, and lack effective materials to improve carrier recombination efficiency.
An emitting layer containing an organometallic compound, specifically an organometallic compound represented by Formula 1, is used as the emitting layer to enhance carrier recombination and light emission.
It improves the brightness and response speed of the light-emitting device, reduces the driving voltage, enhances the carrier recombination efficiency, and improves the overall light-emitting performance.
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Figure CN121342881A_ABST
Abstract
Description
[0001] Cross-references to related applications
[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0094005, filed on July 16, 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 including light-emitting devices, and electronic equipment including light-emitting devices, as well as 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 may be disposed on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode may be sequentially disposed on the first electrode. Holes supplied from the first electrode move towards the emitter layer through the hole transport region, and electrons supplied from the second electrode move towards the emitter layer through the electron transport region. Charge carriers (such as holes and electrons) recombine in the emitter layer to generate excitons. Excitons can transition from an excited state to a ground state, thereby generating light.
[0006] It should be understood that this background section is intended in part to provide 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 comprising an organometallic compound, an electronic device comprising a light-emitting device, and electronic equipment comprising a light-emitting device, as well as an organometallic compound.
[0008] Other aspects will be set forth in part in the description which follows and in part will be obvious from the description or may be learned by practice of embodiments of this disclosure.
[0009] According to an embodiment, the light-emitting device may include: a first electrode, a second electrode facing the first electrode, an interlayer between the first and second electrodes and including an emitting layer, and an organometallic compound represented by Formula 1:
[0010] [Formula 1]
[0011]
[0012] [Formula 1A]
[0013]
[0014] In Formula 1, A can be a group represented by Formula 1A.
[0015] In Formula 1 and Formula 1A,
[0016] M can be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
[0017] X1to X4may each independently be C or N,
[0018] The bond between X1and M can be a coordinate bond,
[0019] One of the bonds between X2and M, the bond between X3and M, and the bond between X4and M can be a coordinate bond, and the remaining two thereof can each be a covalent bond,
[0020] Rings CY1to CY4, rings Ar1to Ar4, and ring Ar7may each independently be a C3-C 60 carbocyclyl group or a C1-C 60 heterocyclyl group,
[0021] L1to L3may each independently be a single bond, *-C(R 1a )(R 1b )-*’, *-C(R 1a )=*’, *=C(R 1a )-*’, *-C(R 1a )=C(R 1b )-*’, *-C(=O)-*’, *-C(=S)-*’, *-C≡C-*’, *-B(R 1a )-*’, *-N(R 1a )-*’, *-O-*’, *-P(R 1a )-*’, *-Si(R 1a )(R 1b )-*’, *-P(=O)(R 1a )-*’, *-S-*’, *-S(=O)-*’, *-S(=O)2-*’, or *-Ge(R 1a )(R 1b )-*’, where * and *’ each indicate a bonding site with an adjacent atom,
[0022] n1to n3may each independently be an integer selected from 1 to 5,
[0023] R1to R4, R 1a , R 1b , T1to T4, T 51 to T54 T 61 To T 63 T7 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or modified by 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),
[0024] a1 to a4 can each be an integer selected from 0 to 10 independently.
[0025] b1 through b4 and b7 can each be an integer selected from 0 to 10 independently.
[0026] R1 to R4, T1 to T4, T 51 To T 54 T 61 To T 63 Two or more of T7 may optionally be bonded together to form an unsubstituted or R-terminated compound. 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,
[0027] The * in Equation 1A indicates the binding site with loop CY1 in Equation 1.
[0028] R 10a Possible forms:
[0029] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;
[0030] 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 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, 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;
[0031] 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, 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 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 21 heteroaryloxy, C1-C 22 heteroaryloxy, C1-C 23 heteroaryloxy, C1-C 21 heteroaryloxy, C1-C 22 heteroaryloxy, C1-C 21 heteroaryloxy, C1-C 22 heteroaryloxy, C1-C 21 heteroaryloxy, C1-C 21 heteroaryloxy, C1-C 21 heteroaryloxy, C1-C 22 heteroaryloxy, C1-C heteroaryloxy, C1-C
[0032] heteroaryloxy, C1-C 31 heteroaryloxy, C1-C 32 heteroaryloxy, C1-C 33 heteroaryloxy, C1-C 31 heteroaryloxy, C1-C 32 heteroaryloxy, C1-C 31 heteroaryloxy, C1-C 32 heteroaryloxy, C1-C 31 heteroaryloxy, C1-C 31 heteroaryloxy, C1-C 31 heteroaryloxy, C1-C 32 heteroaryloxy, C1-C heteroaryloxy, C1-C
[0033] heteroaryloxy, C1-C 11 heteroaryloxy, C1-C 13 heteroaryloxy, C1-C 21 heteroaryloxy, C1-C 23 heteroaryloxy, C1-C 31 heteroaryloxy, C1-C 33 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C 60 heteroaryloxy, C1-C
[0034] In an embodiment, 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 emission layer and an electron transport zone between the emission layer and the second electrode; 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 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.
[0035] In an embodiment, the emission layer can include an organometallic compound represented by Formula 1.
[0036] In an embodiment, the emission layer can include a host and a dopant, and the dopant can include an organometallic compound represented by Formula 1.
[0037] In an embodiment, the dopant can further include a delayed fluorescence material.
[0038] In an embodiment, the host can include a first host compound and a second host compound; the first host compound can be a hole transport host; the hole transport host can be represented by one of Formulae 311-1 to 311-6 explained below; the second host compound can be an electron transport host; and the electron transport host can be represented by one of Formulae 312-1 to 312-4 and 313 explained below.
[0039] According to an embodiment, an electronic device can include a light emitting apparatus.
[0040] In an embodiment, the electronic device can further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof.
[0041] According to an embodiment, an electronic equipment can include a light emitting apparatus.
[0042] In an embodiment, 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 light therapy device, or a signboard.
[0043] According to an embodiment, the organometallic compound can be represented by Formula 1 explained herein.
[0044] In the implementation method, in formula 1A, by The part represented and by The represented parts can be different from each other, and * indicates the binding site with adjacent atoms.
[0045] In the embodiments, X1 may be C, and the ring CY1 may be imidazole, triazole, benzimidazole, naphzimidazole or imidazolepyridinyl.
[0046] In the implementation method, in Equation 1, by The part represented can be one of the parts represented by equations CY1(1) to CY1(5) as explained below.
[0047] In the implementation method, R1 to R4, R 1a R 1b T1 to T4, T 51 To T 54 T 61 To T 63 The T7 and T7 can be used independently as follows:
[0048] Hydrogen, deuterium, -F, -Cl, -Br or -I;
[0049] Unsubstituted or substituted C1-C 20 Alkyl groups: 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, pyrimidinyl, or any combination thereof; or
[0050] Each of the following unsubstituted or substituted phenyl, biphenyl, terphenyl, C1-C 10 Alkylphenyl or naphthyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, C1-C 10 Alkylphenyl or any combination thereof.
[0051] In the implementation, T1 to T4 can each be independently:
[0052] Hydrogen, deuterium, -F or cyano; or
[0053] C1-C6alkyl unsubstituted or substituted with deuterium, -F, cyano, or any combination thereof; 20 C1-C6alkyl unsubstituted or substituted with deuterium, -F, cyano, or any combination thereof;
[0054] In embodiments, each of ring CY2to ring CY4may be independently phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2-benzo[ghi]phenyl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, thienyl, furanyl, indolyl, benzoborolyl, benzophospholyl, indenyl, benzothiazolyl, benzogermyl, benzothienyl, benzoselenophenyl, benzofuranyl, carbazolyl, dibenzoborolyl, dibenzophospholyl, fluorenyl, dibenzothiazolyl, dibenzogermyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuranyl, dibenzothiophene-5-oxide, 9H-fluoren-9-one, dibenzothiophene-5,5-dioxide, azaindolyl, azabenzoborolyl, azabenzophospholyl, azaindenyl, azabenzothiazolyl, azabenzogermyl, azabenzothienyl, azabenzoselenophenyl, azabenzofuranyl, azacarbazolyl, azadibenzoborolyl, azadibenzophospholyl, azafuorenyl, azadibenzothiazolyl, azadibenzogermyl, azadibenzothienyl, azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophene-5-oxide, azo-9H-fluoren-9-one, azadibenzothiophene-5,5-dioxide, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolyl, or 5,6,7,8-tetrahydroquinolyl.
[0055] In embodiments, in formula 1, A can be a group represented by one of formula 1A-11 to formula 1A-17 explained below.
[0056] In embodiments, in formula 1, A can be a group represented by one of formula 1A-21 to formula 1A-27 explained below.
[0057] In embodiments, ring Ar7may be phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, or isoquinolyl.
[0058] In embodiments, the organometallic compound represented by formula 1 can be represented by formula 1-1 or formula 1-2 explained below.
[0059] In an embodiment, the organometallic compound represented by Formula 1 can be one of Compound 1 to Compound 168 explained below.
[0060] It should be understood that the above-mentioned embodiments are described in general and explanatory terms and are not intended to limit the disclosure, or the right by way of limitation, and that the disclosure is not restricted to the above-mentioned embodiments. BRIEF DESCRIPTION OF DRAWINGS
[0061] 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 embodiments of the disclosure and, together with the description, serve to explain the principles of the disclosure. The above and other aspects and features of the disclosure will become more apparent from the following detailed description, taken in conjunction with the accompanying drawings, in which:
[0062] Figure 1 is a schematic cross-sectional view of a light emitting device according to an embodiment;
[0063] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment;
[0064] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment;
[0065] Figure 4 is a schematic perspective view of an electronic appliance including a light emitting device according to an embodiment;
[0066] Figure 5 is a schematic perspective view of an exterior of a vehicle as an electronic appliance including a light emitting device according to an embodiment; and
[0067] Figures 6A to 6C each is a schematic view of an interior of a vehicle according to an embodiment. DETAILED DESCRIPTION
[0068] The disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments of the disclosure 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.
[0069] In the drawings, the size, proportions, and dimensions (e.g., thicknesses) of elements can be exaggerated for ease of description and for clarity. Throughout, like elements and / or like reference characters designate the same elements throughout.
[0070] In the specification, it will be understood that when an element (or components, layer, part, etc.) is referred to as being "on" another element (or components, layer, part, etc.), it can be directly on another element (or components, layer, part, etc.) or intervening elements (or components, layer, part, etc.) can also be present. In the same manner, when an element (or components, layer, part, etc.) is referred to as being "connected," or "coupled," to another element (or components, layer, part, etc.), it can be directly connected or coupled to the other element (or components, layer, part, etc.) or intervening elements (or components, layer, part, etc.) can also be present. In the same manner, when an element (or components, layer, part, etc.) is referred to as "covering" another element (or components, layer, part, etc.), it can be directly covering the other element (or components, layer, part, etc.) or one or more intervening elements (or components, layer, part, etc.) can also be present.
[0071] In the specification, when an element is "directly on" another element, "directly connected to" or "directly coupled to" another element, there are no intervening elements. For example, "directly on" can mean that two layers or two elements are disposed without additional elements (such as an adhesive element) between them.
[0072] In the specification, expressions such as "a", "an" and "the" used in a singular sense are intended to also include the plural form, unless the context clearly indicates otherwise.
[0073] In the specification, the term "and / or" includes any and all combinations of one or more of the associated listed items. For example, "A and / or B" can be understood to mean "A, B, or A and B." The terms "and" and "or" can be used in an inclusive and exclusive sense, and can be understood to be equivalent to "and / or."
[0074] In the specification and claims, the term "at least one of" is intended to include the meaning of "at least one of the group consisting of", for purposes of its meaning and interpretation. For example, "at least one of A, B, and C" can be understood to mean A alone, B alone, C alone, or any combination of two or more of A, B, and C, such as ABC, ACC, BC, or CC. The term "at least one of" modifies the entire list of elements that it precedes, and does not modify the individual elements of the list.
[0075] It will be understood that, although the terms first, second, etc. can be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. Thus, a first element could be termed a second element without departing from the teachings of the present disclosure. Similarly, a second element could be termed a first element without departing from the scope of the present disclosure.
[0076] For ease of description, spatially relative terms, such as "below", "under", "lower", "above", "on", or the like, can be used herein for describing the relationship between one element or component and another element or component as illustrated in the figures. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientations depicted in the figures. For example, in the case of an object that is turned over, the object that is below or under another object, when in the orientation as illustrated in the figures, can be above or on the other object when the device is turned over. Accordingly, the illustrative term "below" can include both a lower position and an upper position. The device can also be oriented in other directions, and as such the spatially relative terms can be interpreted differently depending on the orientation of the device.
[0077] 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 the measurement of the quantity that is recited (e.g., limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the recited value.
[0078] It will be understood that the terms "comprises", "comprising", "includes", "including", "has", "having", "contains" and "containing" or the like, are intended to mean that the features, integers, steps, operations, elements, components or the like, recited in the disclosure are present, but not excluding the presence of one or more other features, integers, steps, operations, elements, components or the like, or the possibility of adding one or more other features, integers, steps, operations, elements, components or the like, to the features, integers, steps, operations, elements, components or the like, recited in the disclosure.
[0079] Unless otherwise defined or specified herein, all terms used using (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. 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.
[0080] According to an embodiment, a light emitting device (e.g., an organic 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.
[0081] Hereinafter, the organometallic compound represented by Formula 1 is described in detail:
[0082] [Formula 1]
[0083]
[0084] In Formula 1, M can be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu).
[0085] In an embodiment, M can be Pt or Pd. In an embodiment, M can be Pt.
[0086] In Formula 1, X1to X4may each independently be C or N. In Formula 1, the bond between X1and M can be a coordinate bond; and one of the bonds between X2and M, the bond between X3and M, and the bond between X4and M can be a coordinate bond, and the remaining two can each be a covalent bond.
[0087] In an embodiment, X1may be C, and the bond between X1and M can be a coordinate bond.
[0088] In an embodiment, X2may be C, and the bond between X2and M can be a covalent bond.
[0089] In an embodiment, X3may be C, and the bond between X3and M can be a covalent bond.
[0090] In an embodiment, X4may be N, and the bond between X4and M can be a coordinate bond.
[0091] In Formula 1, ring CY1to ring CY4may each independently be C3-C 60 carbocyclyl or C1-C 60 heterocyclyl.
[0092] In an embodiment, ring CY1may be imidazolyl, triazolyl, benzimidazolyl, naphthimidazolyl, or imidazopyridinyl.
[0093] In an embodiment, in Formula 1, the moiety represented by may be a moiety represented by one of Formula CY1(1) to Formula CY1(5):
[0094]
[0095] In Formula CY1(1) to Formula CY1(5),
[0096] A can be the same as described herein,
[0097] X 11 may be C(R 11 ) or N, X 12 may be C(R 12 ) or N, X 13 may be C(R 13 ) or N, X 14 may be C(R 14) or N, X 15 may be C(R 15 ) or N, and X 16 may be C(R 16 ) or N,
[0098] R 11 to R 16 may each independently be the same as described for R1, and
[0099] * and *' each indicate a binding site to an adjacent atom.
[0100] In embodiments, ring CY2to ring CY4may each independently be phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2-benzo- phenanthryl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, thienyl, furanyl, indolyl, benzoborolyl, benzo phospholyl, indenyl, benzothiazolyl, benzogermanolyl, benzothienyl, benzoselenophenyl, benzofuranyl, carbazolyl, dibenzoborolyl, dibenzophospholyl, fluorenyl, dibenzothiazolyl, dibenzogermanolyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuranyl, dibenzothiophene-5-oxideyl, 9H-fluoren-9-onyl, dibenzothiophene-5,5-dioxideyl, azaindolyl, azabenzoborolyl, azabenzophospholyl, azaindenyl, azabenzothiazolyl, azabenzogermanolyl, azabenzothienyl, azabenzoselenophenyl, azabenzofuranyl, azacarbazolyl, azadibenzoborolyl, azadibenzophospholyl, azaf luorenyl, azadibenzothiazolyl, azadibenzogermanolyl, azadibenzothienyl, azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophene-5-oxideyl, azo-9H-fluoren-9-onyl, azadibenzothiophene-5,5-dioxideyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolyl, or 5,6,7,8-tetrahydroquinolyl.
[0101] In embodiments, ring CY2may be phenyl, naphthyl, or 1,2,3,4-tetrahydronaphthyl.
[0102] In embodiments, ring CY3may be indolyl, indenyl, carbazolyl, fluorenyl, azaindolyl, azaindenyl, or azacarbazolyl.
[0103] In embodiments, the ring CY4may be pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, or isoquinolinyl.
[0104] In embodiments, in Formula 1, the moiety represented by may be a moiety represented by one of Formula CY2(1) to Formula CY2(13):
[0105]
[0106] In Formula CY2(1) to CY2(13),
[0107] Z 21 may be B(R 27 ), C(R 27 )(R 28 ), N(R 27 ), O, S, or Si(R 27 )(R 28 ), Z 22 may be C(R 27 ), N, or Si(R 27 ),
[0108] R 21 to R 28 may each independently be the same as described with reference to R2, and
[0109] *, *, and *” each indicate a binding site to an adjacent atom.
[0110] In embodiments, in Formula 1, the moiety represented by may be a moiety represented by Formula CY3(1):
[0111]
[0112] In Formula CY3(1),
[0113] X 31 may be C(R 31 ) or N, X 32 may be C(R 32 ) or N, X 33 may be C(R 33 ) or N, X 34 may be C(R 34 ) or N, X 35 may be C(R 35 ) or N, and X 36 may be C(R 36 ) or N,
[0114] R 31 to R 36each independently of the other, the same as described with reference to R3, and
[0115] *and *' each indicate a binding site to an adjacent atom.
[0116] In embodiments, in formula 1, the moiety represented by may be a moiety represented by formula CY4(1):
[0117]
[0118] In formula CY4(1),
[0119] X 41 may be C(R 41 ) or N, X 42 may be C(R 42 ) or N, X 43 may be C(R 43 ) or N, and X 44 may be C(R 44 ) or N,
[0120] R 41 to R 44 each independently of the other, the same as described with reference to R4, and
[0121] *and *' each indicate a binding site to an adjacent atom.
[0122] In formula 1, L1to L3may each independently be a single bond, *-C(R 1a )(R 1b )- *', *-C(R 1a )= *', =C(R 1a )- *', *-C(R 1a )=C(R 1b )- *', *-C(=0)- *', *-C(=S)- *', *-C=C- *', *-B(R 1a )- *', *-N(R 1a )- *', *-0- *', *-P(R 1a )- *', *-Si(R 1a )(R 1b )- *', *-P(=0)(R 1a )- *', *-S- *', *-S(=0)- *', *-S(=0)2- *' or *-Ge(R 1a )(R 1b )- *', wherein *and *' each indicate a binding site to an adjacent atom.
[0123] In embodiments, L1and L3may each be a single bond.
[0124] In embodiments, L2may be *-C(R 1a )(R 1b )-', *-B(R 1a )-', *-N(R 1a )-', *-O-*, *-P(R 1a )-', *-Si(R 1a )(R 1b )-', or *-S-*'. In embodiments, L2may be *-O-*' or *-S-*'.
[0125] In Formula 1, n1 to n3 indicate the number of L1 to L3, respectively, and n1 to n3 can each independently be an integer selected from 1 to 5. In embodiments, n1 to n3 can each be 1.
[0126] In Formula 1, when n1 is 1 and L1 is a single bond, *-(L1) n1 -*' can be a single bond; when n2 is 1 and L2 is a single bond, *-(L2) n2 -*' can be a single bond; and when n3 is 1 and L3 is a single bond, *-(L3) n3 -*' can be a single bond.
[0127] In Formula 1, when n1 is 2 or more than 2, two or more L1 can be the same as or different from each other; when n2 is 2 or more than 2, two or more L2 can be the same as or different from each other; and when n3 is 2 or more than 2, two or more L3 can be the same as or different from each other.
[0128] In Formula 1, R1 to R4, R 1a , and R 1b may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a -substituted C1-C 60 alkyl, unsubstituted or substituted with at least one R 10a -substituted C2-C 60 alkenyl, unsubstituted or substituted with at least one R 10a -substituted C2-C 60 alkynyl, unsubstituted or substituted with at least one R 10a -substituted C1-C 60 alkoxy, unsubstituted or substituted with at least one R 10a -substituted C3-C 60 carbocyclyl, unsubstituted or substituted with at least one R 10a -substituted C1-C 60 heterocyclyl, unsubstituted or substituted with at least one R 10a -substituted C6-C 60aryloxy, 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, -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).
[0129] In the implementation method, R1 to R4, R 1a and R 1b Each can be independently:
[0130] Hydrogen, deuterium, -F, -Cl, -Br or -I;
[0131] Unsubstituted or substituted C1-C 20 Alkyl groups: 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, pyrimidinyl, or any combination thereof; or
[0132] Each of the following unsubstituted or substituted phenyl, biphenyl, terphenyl, C1-C 10 Alkylphenyl or naphthyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, C1-C 10 Alkylphenyl or any combination thereof.
[0133] In Equation 1, two or more of R1 to R4 may optionally be bonded to each other to form an unsubstituted or bonded compound 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.
[0134] In Formula 1, a1to a4may each independently be an integer selected from 0 to 10.
[0135] In Formula 1, A can be a group represented by Formula 1A:
[0136] [Formula 1A]
[0137]
[0138] In Formula 1A, * indicates a binding site with the ring CY1in Formula 1.
[0139] In embodiments, in Formula 1A, the moiety represented by and the moiety represented by may be different from each other, where * indicates a binding site with an adjacent atom.
[0140] In Formula 1A, the ring Ar1to the ring Ar4and the ring Ar7may each independently be a C3-C 60 carbocyclyl group or a C1-C 60 heterocyclyl group.
[0141] In embodiments, the ring Ar1to the ring Ar4and the ring Ar7may each independently be a phenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, or an isoquinolyl group.
[0142] In embodiments, in Formula 1, A can be a group represented by one of Formula 1A-11 to Formula 1A-17:
[0143]
[0144] In Formula 1A-11 to Formula 1A-17,
[0145] Y 11 may be N or C(T 11 ), Y 12 may be N or C(T 12 ), Y 13 may be N or C(T 13 ), and Y 14 may be N or C(T 14 ),
[0146] Y 21 may be N or C(T 21 ), Y 22 may be N or C(T 22 ), Y 23 may be N or C(T 23 ), and Y 24 may be N or C(T 24 ),
[0147] Y 31 may be N or C(T 31 ), Y 32 may be N or C(T 32 ), Y 33 may be N or C(T 33 ), and Y 34 may be N or C(T 34 ),
[0148] Y 41 may be N or C(T 41 ), Y 42 may be N or C(T 42 ), Y 43 may be N or C(T 43 ), and Y 44 may be N or C(T 44 ),
[0149] T 11 to T 14 may each independently be the same as described with reference to T1,
[0150] T 21 to T 24 may each independently be the same as described with reference to T2,
[0151] T 31 to T 34 may each independently be the same as described with reference to T3,
[0152] T 41 to T 44 may each independently be the same as described with reference to T4,
[0153] rings Ar7, T 51 to T 54 , T 61 to T 63 , T7, and b7may each be the same as described herein, and
[0154] * indicates a binding site with ring CY1in Formula 1.
[0155] In embodiments, rings Ar1to Ar4and Ar7may each independently be phenyl.
[0156] In embodiments, in Formula 1, A can be a group represented by one of Formula 1A-21 to Formula 1A-27:
[0157]
[0158]
[0159] In formula 1A-21 to formula 1A-27,
[0160] T 11 to T 14 may each independently be the same as described with reference to T1,
[0161] T 21 to T 24 may each independently be the same as described with reference to T2,
[0162] T 31 to T 34 may each independently be the same as described with reference to T3,
[0163] T 41 to T 44 may each independently be the same as described with reference to T4,
[0164] ring Ar7, T 51 to T 54 , T 61 to T 63 , T7and b7may each be the same as described herein, and
[0165] * indicates the binding site to the ring CY1in formula 1.
[0166] In formula 1A, T1to T4, T 51 to T 54 , T 61 to T 63 and T7may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted with at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted with at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted with at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclyl, unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclyl, unsubstituted or substituted with at least one R 10a substituted C6-C 60 aryloxy, unsubstituted or substituted with at least one R 10a substituted C6-C 60 arylthio, unsubstituted or substituted with at least one R 10aReplacement C7-C 60 Aryl, unsubstituted or with at least one R 10a Replacement C2-C 60 Heteroaryl, -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).
[0167] In the implementation, T1 to T4, T 51 To T 54 T 61 To T 63 The T7 and T7 can be used independently as follows:
[0168] Hydrogen, deuterium, -F, -Cl, -Br or -I;
[0169] Unsubstituted or substituted C1-C 20 Alkyl groups: 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, pyrimidinyl, or any combination thereof; or
[0170] Each of the following unsubstituted or substituted phenyl, biphenyl, terphenyl, C1-C 10 Alkylphenyl or naphthyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, C1-C 10 Alkylphenyl or any combination thereof.
[0171] In the implementation, T1 to T4 can each be independently:
[0172] Hydrogen, deuterium, -F or cyano; or
[0173] Unsubstituted or substituted C1-C with deuterium, -F, cyano, or any combination thereof 20 alkyl.
[0174] In Equation 1A, T1 to T4, T 51 To T 54 T 61To T 63 Two or more of T7 may optionally be bonded together to form an unsubstituted or R-terminated compound. 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.
[0175] In Equation 1A, b1 to b4 and b7 can each be an integer selected from 0 to 10 independently.
[0176] In the instruction manual, R 10a Possible forms:
[0177] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;
[0178] 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, 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;
[0179] 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C60 aralkyl or C2-C 60 heteroaralkyl: deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclyl, C1-C 60 heterocyclyl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), or any combination thereof; or
[0180] -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
[0181] 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; -CI; -Br; -I; hydroxyl; cyano; nitro; or C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, or any combination thereof substituted;60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclyl, C1-C 60 heterocyclyl, C7-C 60 aralkyl or C2-C 60 heteroaralkyl.
[0182] In embodiments, the organometallic compound represented by Formula 1 can be represented by Formula 1-1 or Formula 1-2:
[0183] [Formula 1-1]
[0184]
[0185] [Formula 1-2]
[0186]
[0187] In Formula 1-1 and Formula 1-2,
[0188] M, A, L1 to L3, and n1 to n3 can each be the same as described herein,
[0189] X 11 may be C(R 11 ) or N, X 12 may be C(R 12 ) or N, X 13 may be C(R 13 ) or N, and X 14 may be C(R 14 ) or N,
[0190] X 21 may be C(R 21 ) or N, X 22 may be C(R 22 ) or N, and X 23 may be C(R 23 ) or N,
[0191] X 31 may be C(R 31 ) or N, X 32 may be C(R 32 ) or N, X 33 may be C(R 33 ) or N, X 34 may be C(R 34 ) or N, X 35 may be C(R 35 ) or N, and X 36 may be C(R 36) or N,
[0192] X 41 may be C(R 41 ) or N, X 42 may be C(R 42 ) or N, X 43 may be C(R 43 ) or N, and X 44 may be C(R 44 ) or N,
[0193] R 11 to R 14 may each independently be the same as described with reference to R1,
[0194] R 21 to R 23 may each independently be the same as described with reference to R2,
[0195] R 31 to R 36 may each independently be the same as described with reference to R3, and
[0196] R 41 to R 44 may each independently be the same as described with reference to R4.
[0197] In embodiments, the organometallic compound represented by Formula 1 can be one of Compound 1 to Compound 168:
[0198]
[0199]
[0200]
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210] In an embodiment, the organometallic compound represented by Formula 1 can emit phosphorescent blue light or fluorescent blue light.
[0211] In an embodiment, the organometallic compound represented by Formula 1 can emit light having a maximum emission wavelength in a range of about 380 nm to about 495 nm. For example, the organometallic compound represented by Formula 1 can emit light having a maximum emission wavelength in a range of about 400 nm to about 490 nm. For example, the organometallic compound represented by Formula 1 can emit light having a maximum emission wavelength in a range of about 420 nm to about 485 nm. For example, the organometallic compound represented by Formula 1 can emit light having a maximum emission wavelength in a range of about 425 nm to about 480 nm. For example, the organometallic compound represented by Formula 1 can emit light having a maximum emission wavelength in a range of about 430 nm to about 475 nm or about 440 nm to about 475 nm.
[0212] In an embodiment, in Formula 1A, the moiety represented by may be different from the moiety represented by For example, the group represented by Formula 1A can have an asymmetric structure with respect to a symmetry axis as shown below:
[0213] [Formula 1A]
[0214]
[0215] Since the organometallic compound represented by Formula 1 includes the group represented by Formula 1A, which is asymmetric and bulky, intermolecular Dexter energy transfer can be reduced, and since intramolecular motion is inhibited, a Stokes shift can be reduced. Accordingly, the organometallic compound represented by Formula 1 can exhibit improved photoluminescence quantum yield (PLQY) and material stability.
[0216] Therefore, when the organometallic compound represented by Formula 1 is used as a dopant of an emission layer, a light-emitting device having high light-emitting efficiency and / or long lifespan can exhibit a shortened emission wavelength and improved color purity.
[0217] A person of ordinary skill in the art can recognize a method of synthesizing the organometallic compound represented by Formula 1 by referring to the synthesis examples and / or embodiments provided below.
[0218] According to an embodiment, a light-emitting device (e.g., an organic light-emitting device) can include at least one organometallic compound represented by Formula 1. 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.
[0219] 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 disposed between the first electrode and the emission layer and an electron transport zone disposed between the emission layer and the second electrode; 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 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.
[0220] In embodiments, the interlayer can include an organometallic compound represented by Formula 1.
[0221] In embodiments, the emission layer can include an organometallic compound represented by Formula 1.
[0222] In embodiments, the emission layer can emit red light, green light, blue light, and / or white light. For example, the emission layer can emit blue light. The blue light can have a maximum emission wavelength in a range of, for example, about 400 nm to about 480 nm.
[0223] In embodiments, the emission layer can include a host and a dopant, and the dopant can include an organometallic compound represented by Formula 1. For example, the organometallic compound represented by Formula 1 can be used as a dopant.
[0224] In embodiments, the light emitting device can further include a capping layer disposed outside of the first electrode and / or outside of the second electrode.
[0225] For example, the light emitting device can further include at least one of a first capping layer disposed outside of the first electrode and a second capping layer disposed outside of the second electrode, wherein the organometallic compound represented by Formula 1 can be included in at least one of the first capping layer and the second capping layer. Further details regarding the first capping layer and / or the second capping layer can be the same as described herein.
[0226] In embodiments, the light emitting device can further include a first capping layer disposed outside of the first electrode. For example, the first capping layer can include an organometallic compound represented by Formula 1.
[0227] In embodiments, the light emitting device can further include a second capping layer disposed outside of the second electrode. For example, the second capping layer can include an organometallic compound represented by Formula 1.
[0228] In embodiments, the light emitting device can further include a first capping layer disposed outside of the first electrode and a second capping layer disposed outside of the second electrode. For example, at least one of the first capping layer and the second capping layer can each independently include an organometallic compound represented by Formula 1.
[0229] In the specification, the term “(interlayer and / or capping layer) includes an organic metal compound represented by Formula 1” can be understood as “(interlayer and / or capping layer) can include one kind of organic metal compound represented by Formula 1 or two or more different kinds of organic metal compounds each independently represented by Formula 1”.
[0230] In the specification, the term “interlayer” can refer to a single layer and / or multiple layers between the first electrode and the second electrode of the light-emitting device.
[0231] According to another embodiment, 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, wherein the first electrode of the light-emitting device can be electrically connected to the source electrode or the drain electrode. In an embodiment, the electronic device can further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. More details about the electronic device can be the same as described herein.
[0232] According to another embodiment, an electronic device can include a light-emitting device.
[0233] In an embodiment, the electronic device can be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a 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. More details about the electronic device can be the same as described herein.
[0234] [ Figure 1 Description of the Drawings]
[0235] Figure 1 is a schematic cross-sectional view of a light-emitting device 10 according to an embodiment. The light-emitting device 10 includes a first electrode 110, an interlayer 130, and a second electrode 150.
[0236] Hereinafter, a structure of a light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10 are described with reference to Figure 1
[0237] [First Electrode 110]
[0238] In Figure 1 In an embodiment, a substrate can be further included under the first electrode 110 or on the second electrode 150. The substrate can be a glass substrate or a plastic substrate. In an embodiment, 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.
[0239] 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.
[0240] 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. 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.
[0241] 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. In an embodiment, the first electrode 110 can have a three-layer structure of ITO / Ag / ITO.
[0242] [Interlayer 130]
[0243] The interlayer 130 is disposed on the first electrode 110. The interlayer 130 includes an emission layer.
[0244] The interlayer 130 can further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150.
[0245] In addition to various organic materials, the interlayer 130 can further include a metal-containing compound such as an organic metal compound represented by Formula 1 or an inorganic material such as a quantum dot, etc.
[0246] In an embodiment, the interlayer 130 can include two or more emission units stacked between the first electrode 110 and the second electrode 150, and at least one charge generation layer each between adjacent ones of the two or more emission units. When the interlayer 130 includes two or more emission units and at least one charge generation layer as described above, the light emitting device 10 can be a tandem light emitting device.
[0247] [hole transport zone in interlayer 130]
[0248] The hole transport zone 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 containing different materials, or a multi-layer structure including a plurality of layers containing different materials.
[0249] 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.
[0250] In an embodiment, the hole transport zone can have 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, in which each layer of each structure can be stacked in the order of its respective recitation from the first electrode 110, but the structure of the hole transport zone is not limited thereto.
[0251] In an embodiment, the hole transport zone can include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0252] [Formula 201]
[0253]
[0254] [Formula 202]
[0255]
[0256] In Formula 201 and Formula 202,
[0257] L 201 to L 204 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,
[0258] L 205 may be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or substituted with at least one R 10a substituted C1-C 20 alkylene, unsubstituted or substituted with at least one R 10a substituted C2-C 20 alkenylene, unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclyl, or unsubstituted or substituted with at least one R10a Replacement C1-C 60 Heterocyclic group,
[0259] xa1 to xa4 can each be an integer selected from 0 to 5 independently.
[0260] xa5 can be an integer selected from 1 to 10.
[0261] 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,
[0262] 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 bonded to each other 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.),
[0263] 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 bonded to each other to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, and
[0264] na1 can be an integer selected from 1 to 4.
[0265] 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:
[0266]
[0267] In equations CY201 to CY217, R 10b and R 10c Each can be independently compared with reference R. 10a The descriptions are the same, CY ring 201 To CY204 Each can be independently C3-C 20 Carbocyclic or C1-C 20 Heterocyclic group, and at least one hydrogen in formulas CY201 to CY217 may be unsubstituted or R-substituted. 10a replace.
[0268] In the implementation, in formulas CY201 to CY217, the ring CY 201 To CY 204 Each can be independently phenyl, naphthyl, phenanthryl or anthracene.
[0269] 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 CY203.
[0270] In an embodiment, the compound represented by formula 201 may include at least one of the groups represented by formulas CY201 to CY203 and at least one of the groups represented by formulas CY204 to CY217.
[0271] In the implementation, in formula 201, xa1 can be 1, R 201 It can be a group represented by one of the formulas CY201 to CY203, xa2 can be 0, and R 202 It can be a group represented by one of the formulas CY204 to CY207.
[0272] In an embodiment, the compound represented by formula 201 and the compound represented by formula 202 may each not include the groups represented by formulas CY201 to CY203.
[0273] In an embodiment, the compound represented by formula 201 and the compound represented by formula 202 may each not include the groups represented by formulas CY201 to CY203, and may each independently include at least one of the groups represented by formulas CY204 to CY217.
[0274] In embodiments, the compounds represented by formula 201 and the compounds represented by formula 202 may each not include the groups represented by formulas CY201 to CY217.
[0275] 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), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), or any combination thereof:
[0276]
[0277]
[0278]
[0279]
[0280]
[0281] 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.
[0282] 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.
[0283] [p-dopant]
[0284] In addition to these materials, the hole transport region may further include charge-generating materials for improving conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer composed of charge-generating materials).
[0285] The charge-generating material can be, for example, a p-doped agent.
[0286] 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.
[0287] In embodiments, p-dopersive agents may include quinone derivatives, cyano-containing compounds, compounds comprising elements EL1 and EL2, or any combination thereof.
[0288] Examples of quinone derivatives may include TCNQ and F4-TCNQ.
[0289] Examples of cyano-containing compounds may include HAT-CN and compounds represented by formula 221:
[0290]
[0291] [Equation 221]
[0292]
[0293] In Equation 221,
[0294] 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
[0295] 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.
[0296] 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.
[0297] 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.).
[0298] Examples of metalloids can include silicon (Si), antimony (Sb), and tellurium (Te).
[0299] Examples of nonmetals can include oxygen (O) and halogens (e.g., F, Cl, Br, I, etc.).
[0300] Examples of compounds including an element EL1 and an element EL2 can include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or any combination thereof.
[0301] 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.).
[0302] Examples of metal halides can include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.
[0303] 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.
[0304] Examples of alkaline earth 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.
[0305] 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.).
[0306] Examples of the post-transition metal halide can include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (e.g., InI3, etc.), and tin halides (e.g., SnI2, etc.).
[0307] Examples of the lanthanide metal halide can include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3.
[0308] Examples of the metalloid halide can include antimony halides (e.g., SbCl5, etc.).
[0309] Examples of the metal telluride 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.).
[0310] [emissive layer in interlayer 130]
[0311] 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 of the red emissive layer, the green emissive layer, and the 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 of the red light emitting material, the green light emitting material, and the blue light emitting material, where the two or more materials can be mixed with each other in a single layer to emit white light. For example, the emissive layer can emit blue light.
[0312] In an embodiment, the emissive layer can include the organometallic compound represented by Formula 1 as described herein.
[0313] The emissive layer can include a host and a dopant.
[0314] In an embodiment, the dopant can include an organic metal compound represented by Formula 1 as described herein. In this regard, the dopant can include a phosphorescent dopant, a fluorescent dopant, a delayed fluorescence material, or any combination thereof, in addition to the organic metal compound represented by Formula 1. The emission layer can further include a phosphorescent dopant, a fluorescent dopant, etc., in addition to the organic metal compound represented by Formula 1. The phosphorescent dopant and the fluorescent dopant will be described later.
[0315] The amount of the dopant in the emission layer can be in the range of about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the host.
[0316] In an embodiment, the emission layer can include a quantum dot.
[0317] 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.
[0318] The thickness of the emission layer can be in the range of about to about . For example, the thickness of the emission layer can be in the range of about to about . When the thickness of the emission layer is in any of the above ranges, excellent light emitting characteristics can be obtained without a significant increase in driving voltage.
[0319] [Host]
[0320] The host can include, for example, a carbazole-containing compound, an anthracene-containing compound, or any combination thereof.
[0321] In an embodiment, the host can include a compound represented by Formula 301:
[0322] [Formula 301]
[0323] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0324] In Formula 301,
[0325] 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 ,
[0326] xb11 can be 1, 2, or 3.
[0327] xb1 can be an integer selected from 0 to 5.
[0328] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or 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 groups, -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 ),
[0329] xb21 can be an integer selected from 1 to 5, and
[0330] Q 301 To Q 303 Each can be independently identical to the description in Q1.
[0331] In the implementation, in formula 301, when xb11 is 2 or greater, two or more Ar 301 They can be connected to each other via a single key.
[0332] In embodiments, the main body may include a compound represented by formula 301-1, a compound represented by formula 301-2, or any combination thereof:
[0333] [Formula 301-1]
[0334]
[0335] [Formula 301-2]
[0336]
[0337] In Formula 301-1 and Formula 301-2,
[0338] 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 heterocyclyl, each of which is unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclyl,
[0339] X 301 may be O, S, N[(L 304 ) xb4 -R 304 ], C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0340] xb22and xb23may each independently be 0, 1 or 2,
[0341] L 301 , xb1and R 301 may each be the same as described in the specification,
[0342] L 302 to L 304 may each independently be the same as described with reference to L 301 ,
[0343] xb2to xb4may each independently be the same as described with reference to xb1, and
[0344] R 302 to R 305 and R 311 to R 314 may each independently be the same as described with reference to R 301 .
[0345] In embodiments, the host can include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. In embodiments, the host can include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0346] In an embodiment, the host can include one of compounds H1 to H128; 9,10-di(2-naphthyl)anthracene (ADN); 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN); 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN); 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP); 1,3-bis(9-carbazolyl)benzene (mCP); 1,3,5-tris(carbazol-9-yl)benzene (TCP); or any combination thereof:
[0347]
[0348]
[0349]
[0350]
[0351]
[0352]
[0353]
[0354] In an embodiment, the host can include a first host compound and a second host compound.
[0355] In an embodiment, the first host compound can be a hole transport host.
[0356] In an embodiment, the second host compound can be an electron transport host.
[0357] In the specification, the term "hole transport host" can refer to a compound including a hole transport moiety.
[0358] In the specification, the term "electron transport host" can refer not only to a compound including an electron transport moiety, but also to a bipolar compound having a bipolar property.
[0359] In the specification, the terms "hole transport host" and "electron transport host" can each be understood according to a relative difference between hole mobility and electron mobility in the hole transport host and the electron transport host. For example, even when an electron transport host does not include an electron transport moiety, a bipolar compound exhibiting a relatively high electron mobility than a hole transport host can be used as an electron transport host.
[0360] In an embodiment, the hole transport host can be represented by one of formulas 311-1 to 311-6, and the electron transport host can be represented by one of formulas 312-1 to 312-4 and 313:
[0361] [Formula 311-1]
[0362]
[0363] [Formula 311-2]
[0364]
[0365] [Formula 311-3]
[0366]
[0367] [Formula 311-4]
[0368]
[0369] [Formula 311-5]
[0370]
[0371] [Formula 311-6]
[0372]
[0373] [Formula 312-1]
[0374]
[0375] [Formula 312-2]
[0376]
[0377] [Formula 312-3]
[0378]
[0379] [Formula 312-4]
[0380]
[0381] [Formula 313]
[0382]
[0383] [Formula 313A]
[0384]
[0385] In Formulae 311-1 to 311-6, 312-1 to 312-4, 313, and 313A,
[0386] Ar 301 may be unsubstituted or substituted with at least one R 10a substituted C3-C60 carbocyclyl or C1-C 10a substituted C1-C 60 heterocyclyl,
[0387] A 301 to A 304 may each independently be C3-C 60 carbocyclyl or C1-C 60 heterocyclyl,
[0388] X 301 may be O, S, N[(L 304 ) xb4 -R 304 ], C[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ] or Si[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ],
[0389] X 302 , Y 301 and Y 302 may each independently be a single bond, O, S, N[(L 305 ) xb5 -R 305 ], C[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ], Si[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ] or S(=O)2,
[0390] xb1to xb5may each independently be 0, 1, 2, 3, 4 or 5,
[0391] xb6may be 1, 2, 3, 4 or 5,
[0392] X 321 to X 328 may each independently be N or C[(L 324 ) xb24 -R 324 ],
[0393] Y 321 may be *-O-*', *-S-*', *-N[(L 325 ) xb25 -R 325 ]-*', *-C[(L 325 ) xb25 -R 325 ][(L 326 ) xb26 -R 326 ]-*', *-C[(L 325 ) xb25 -R 325 ] = C[(L 326 ) xb26 -R 326 ]-*', *-C[(L 325 ) xb25 -R 325 ] = N-*' or *-N = C[(L 326 ) xb26 -R 326 ]-*',
[0394] k21may be 0, 1 or 2, wherein when k21is 0, Y 321 may be absent,
[0395] xb21to xb26may each independently be 0, 1, 2, 3, 4 or 5,
[0396] A 31 , A 32 and A 34 may each independently be C3-C 60 carbocyclyl or C1-C 30 heterocyclyl,
[0397] A 33 may be a group represented by formula 313A,
[0398] X 31 may be N[(L 335 ) xb35 -(R 335 )], O, S, Se, C[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )], or Si[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )],
[0399] xb31 to xb36 can each be independently 0, 1, 2, 3, 4 or 5.
[0400] xb42 to xb44 can each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
[0401] L 301 To L 306 L 321 To L 326 and L 331 To L 336 Each can be independently a single bond, unsubstituted, or bonded 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 C2-C 20 alkyne group, unsubstituted or with at least one R 10a Replacement C3-C 10 Cycloalkylene, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkenyl, unsubstituted or with at least one R 10a Replacement C1-C 10 Heterocyclic alkenyl, unsubstituted or with at least one R 10a Replacement C6-C 60 aryl, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Substituted divalent nonaromatic fused polycyclic groups or unsubstituted groups or groups modified by at least one R 10a Substituted divalent non-aromatic fused heterocyclic groups,
[0402] R 301 To R 305 R 311 To R 314 R 321 To R 326 and R 331 To R 336 Each group can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60alkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 10 cycloalkyl, unsubstituted or substituted by at least one R 10a substituted C1-C 10 heterocycloalkyl, unsubstituted or substituted by at least one R 10a substituted C3-C 10 cycloalkenyl, unsubstituted or substituted by at least one R 10a substituted C1-C 10 heterocycloalkenyl, unsubstituted or substituted by at least one R 10a substituted C6-C 60 aryl, unsubstituted or substituted by at least one R 10a substituted C6-C 60 aryloxy, unsubstituted or substituted by at least one R 10a substituted C6-C 60 arylthio, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heteroaryl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heteroaryloxy, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heteroarylthio, unsubstituted or substituted by at least one R 10a substituted monovalent non-aromatic fused polycyclic radical, unsubstituted or substituted by at least one R 10a substituted monovalent non-aromatic fused heteropolycyclic radical, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) or -P(=S)(Q1)(Q2),
[0403] R 321 to R 326 two or more adjacent radicals from the group consisting of R 10a substituted C3-C 60 carbocyclic radical or unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic radical,
[0404] R 10a may be:
[0405] deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, or nitro;
[0406] each unsubstituted or substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy: deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbocyclyl, C1-C 60 heterocyclyl, C6-C 60 aryloxy, C6-C 60 aralkyl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, C7-C 60 aralkyl, C2-C 60 heteroarylalkyl, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ), or any combination thereof;
[0407] each unsubstituted or substituted C3-C 60 carbocyclyl, C1-C 60 heterocyclyl, C6-C 60 aryloxy, C6-C 60 aralkyl, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, C7-C 60 aralkyl, or C2-C 60 heteroarylalkyl: deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclyl, C1-C 60 heterocyclyl, C6-C 60Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, 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
[0408] -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
[0409] 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; or 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 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups.
[0410] In an embodiment, the first host compound and the second host compound can form an exciplex.
[0411] [Phosphorescent dopant]
[0412] The phosphorescent dopant can include at least one transition metal as a central metal.
[0413] 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.
[0414] The phosphorescent dopant can be electrically neutral.
[0415] In an embodiment, the phosphorescent dopant can include an organometallic compound represented by Formula 1.
[0416] In an embodiment, the phosphorescent dopant can include an organometallic compound represented by Formula 401:
[0417] [Formula 401]
[0418] M(L 401 ) xc1 (L 402 ) xc2
[0419] [Formula 402]
[0420]
[0421] In Formula 401 and Formula 402,
[0422] M can be a transition metal (for example, Ir, Pt, Pd, Os, Ti, Au, Hf, Eu, Tb, Rh, Re, or Tm),
[0423] 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,
[0424] L 402 may be an organic ligand, and xc2may be 0, 1, 2, 3, or 4, wherein when xc2is 2 or more, two or more L 402 may be the same as or different from each other,
[0425] X 401 and X 402 may each independently be nitrogen or carbon,
[0426] Ring A 401 and Ring A 402 may each independently be C3-C 60Carbocyclic or C1-C 60 Heterocyclic group,
[0427] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 411 )-*'、*-C(Q 411 (Q) 412 )-*'、
[0428] *-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 ) = *' or * = C = *',
[0429] 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 ),
[0430] Q 411 To Q 414 Each can be independently identical to the description in reference Q1.
[0431] 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 ),
[0432] Q 401 To Q 403 Each can be independently identical to the description in reference Q1.
[0433] xc11 and xc12 can each be an integer selected from 0 to 10 independently, and
[0434] In Equation 402, * and *' each indicate the binding site with M in Equation 401.
[0435] In the implementation, in formula 402, X 401 It can be nitrogen and X 402 It can be carbon, or X 401 and X 402 Each can be nitrogen.
[0436] 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 independently compared with reference T 401 The descriptions are the same.
[0437] In Equation 401, L 402 It can be an organic ligand. In the embodiment, L... 402 It may include halogen groups, diketone groups (e.g., acetylacetonate groups), carboxylic acid groups (e.g., pyridine carboxyl groups), -C (=O), isonitrile groups, -CN groups, phosphorus groups (e.g., phosphine groups, phosphite groups, etc.) or any combination thereof.
[0438] In this embodiment, the phosphorescent dopant may include, for example, one or any combination of compounds PD1 to PD39:
[0439]
[0440]
[0441]
[0442] [Fluorescent dopant]
[0443] Fluorescent dopants may include amine-containing compounds, styrene-containing compounds, or any combination thereof.
[0444] In embodiments, the fluorescent dopant can include a compound represented by Formula 501:
[0445] [Formula 501]
[0446]
[0447] In Formula 501,
[0448] Ar 501 , L 501 to L 503 , R 501 , and R 502 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,
[0449] xd1to xd3may each independently be 0, 1, 2, or 3, and
[0450] xd4may be 1, 2, 3, 4, 5, or 6.
[0451] In embodiments, in Formula 501, Ar 501 may be a fused ring group in which three or more monocyclic groups are fused together (e.g., anthracenyl, 1,2-phenanthryl, pyrenyl, etc.).
[0452] In embodiments, in Formula 501, xd4may be 2.
[0453] In embodiments, the fluorescent dopant can include one of compounds FD1 to FD37; DPVBi; DPAVBi; or any combination thereof:
[0454]
[0455]
[0456]
[0457]
[0458] [Delayed fluorescence material]
[0459] The emission layer can further include a delayed fluorescence material.
[0460] In the specification, the delayed fluorescence material can be selected from a compound capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0461] 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.
[0462] In an embodiment, the 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 at least about 0 eV and not greater than 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 satisfies the above range, upconversion of the delayed fluorescence material from the triplet state to the singlet state can effectively occur, and thus, the light-emitting efficiency of the light-emitting device 10 can be improved.
[0463] 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) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, and a π-electron deficient nitrogen-containing C1-C 60 heterocyclic group, etc.); or a material including a C8-C 60 polycyclic group including at least two cyclic groups fused to each other while sharing boron (B).
[0464] In an embodiment, the delayed fluorescence material can include at least one of Compound DF1 to Compound DF9:
[0465]
[0466] [Quantum dots]
[0467] The emission layer can include quantum dots.
[0468] In the specification, the quantum dots can be crystals of a semiconductor compound. The quantum dots can emit light of various emission wavelengths according to the size of the crystals. By adjusting the element ratio of the quantum dot compound, the quantum dots can emit light of various emission wavelengths.
[0469] The diameter of the quantum dots can be, for example, in the range of about 1 nm to about 10 nm.
[0470] The quantum dots 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.
[0471] 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 can naturally serve as a dispersant coordinated on the surface of the quantum dot particles and control the growth of the quantum dot particles. Accordingly, the wet-chemical process can control the growth of the quantum dot particles by a low-cost process that can be easily performed compared to a vapor deposition method such as a metal organic chemical vapor deposition (MOCVD) process, a molecular beam epitaxy (MBE) process, etc.
[0472] 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.
[0473] Examples of the Group II-VI semiconductor compound can include: a binary compound such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; a ternary compound such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; a quaternary compound such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; and any combination thereof.
[0474] Examples of Group III-V semiconductor compounds can include binary compounds such as GaN, GaP, GaAs, GaSb, AIN, AIP, AIAs, AISb, InN, InP, InAs, or InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AINP, AINAs, AlNSb, AIPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb, etc.; 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, InAlZnP, etc.
[0475] Examples of Group III-VI semiconductor compounds can include binary compounds such as GaS, Ga2S3, GaSe, Ga2Se3, GaTe, InS, InSe, In2Se3, and InTe, etc.; ternary compounds such as InGaS3and InGaSe3, etc.; and any combination thereof.
[0476] Examples of Group I-III-VI semiconductor compounds can include ternary compounds such as AgInS, AgInS2, AgInSe2, AgGaS, AgGaS2, AgGaSe2, CuInS, CuInS2, CuInSe2, CuGaS2, CuGaSe2, CuGaO2, AgGaO2, or AgAlO2, etc.; quaternary compounds such as AgInGaS2or AgInGaSe2, etc.; or any combination thereof.
[0477] Examples of Group IV-VI semiconductor compounds can include binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe; quaternary compounds such as SnPbSSe, SnPbSeTe, or SnPbSTe; and any combination thereof.
[0478] Examples of the Group IV element or compound can include: a single element material such as Si or Ge; a binary compound such as SiC or SiGe; and any combination thereof.
[0479] Each element included in a compound such as a binary compound, a ternary compound, or a quaternary compound can exist in the particle in a uniform concentration or in a non-uniform concentration. The chemical formula of the quantum dot compound as described above can each refer to the kind of elements included in each compound, in which the element ratio of the compound can vary. For example, AgInGaS2may be expressed as AgIn X Ga 1-X S2(wherein x is a real number satisfying 0 < x < 1).
[0480] In an embodiment, 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, when the quantum dot has a core-shell structure, the material included in the core and the material included in the shell can be different from each other.
[0481] The shell of the quantum dot can serve as a protective layer that prevents chemical degeneration of the core to maintain a semiconductor property and / or can serve as a charging layer that imparts an electrophoretic property 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 element of the material present in the shell decreases toward the center of the core.
[0482] Examples of the shell of the quantum dot can include a metal oxide, a metalloid oxide, a non-metal oxide, a semiconductor compound, and any combination thereof. Examples of the metal oxide or the non-metal oxide can include: a binary compound such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, or NiO; a ternary compound such as MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4; and any combination thereof. Examples of the semiconductor compound 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, and any combination thereof as described herein. For example, the semiconductor compound can include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaS, GaSe, AgGaS, AgGaS2, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0483] The full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dots can be equal to or less than about 45 nm. For example, the FWHM of the emission wavelength spectrum of the quantum dots can be equal to or less than about 40 nm. For example, the FWHM of the emission wavelength spectrum of the quantum dots can be equal to or less than about 30 nm. The FWHM of the emission wavelength spectrum of the quantum dots can be within any of the above ranges, which can increase color purity or color reproducibility. Light emitted by the quantum dots can be emitted in all directions, such that wide viewing angles can be improved.
[0484] In embodiments, the quantum dots can be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles; nanotubes; nanowires; nanofibers; or nanoplates.
[0485] By adjusting the size of the quantum dots, the energy band gap can be adjusted, and thus, light of various wavelengths can be obtained from the quantum dot emission layer. Accordingly, by using quantum dots as described above (by using quantum dots of different sizes or changing the elemental ratio of the quantum dot compound), a light emitting device capable of emitting light of various wavelengths can be implemented. In embodiments, the size of the quantum dots or the elemental ratio of the quantum dot compound can be adjusted so that red light, green light, and / or blue light can be emitted. In embodiments, the quantum dots can be configured to emit white light through a combination of light of various colors.
[0486] [Electron transport zone in interlayer 130]
[0487] 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.
[0488] 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.
[0489] In embodiments, 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, but the structure of the electron transport zone is not limited thereto.
[0490] 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 A metal-free compound of the heterocyclyl group.
[0491] In embodiments, the electron transport zone can include a compound represented by Formula 601:
[0492] [Formula 601]
[0493] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0494] In Equation 601,
[0495] Ar 601 and L 601 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,
[0496] xe11 can be 1, 2, or 3.
[0497] xe1 can be 0, 1, 2, 3, 4, or 5.
[0498] R 601 It can be unsubstituted or 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, -Si(Q) 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) or -P(=O)(Q 601 (Q) 602 ),
[0499] Q 601 To Q 603 Each can be independently identical to the description in reference Q1.
[0500] xe21 can be 1, 2, 3, 4, or 5, and
[0501] Ar 601 L 601 and R 601 At least one of them can be independently unsubstituted or by at least one R. 10a Substituted π-electron-deficient nitrogen-containing C1-C 60 Heterocyclic group.
[0502] In an implementation, in formula 601, when xe11 is 2 or greater, two or more Ar 601may be connected together via a single bond.
[0503] In embodiments, in Formula 601, Ar 601 may be unsubstituted or substituted with at least one R 10a substituted anthracenyl.
[0504] In embodiments, the electron transport zone can include a compound represented by Formula 601-1:
[0505] [Formula 601-1]
[0506]
[0507] In Formula 601-1,
[0508] X 614 may be N or C(R 614 ), X 615 may be N or C(R 615 ), X 616 may be N or C(R 616 ), and X 614 at least one of X 616 may each be N,
[0509] L 611 to L 613 may each independently be the same as L 601 described above with reference to L
[0510] xe611 to xe613 may each independently be the same as xe1 described above with reference to Formula 601,
[0511] R 611 to R 613 may each independently be the same as R 601 described above with reference to R
[0512] R 614 to R 616 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, 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.
[0513] In embodiments, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
[0514] 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, TSPO1, TPBI, or any combination thereof:
[0515]
[0516]
[0517]
[0518]
[0519] 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 these ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage when the thickness of the buffer layer, hole blocking layer, electron control layer, electron transport layer, and / or electron transport region is within these ranges.
[0520] 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.
[0521] The metal-containing material can include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkali metal complex can be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the metal ion of the alkaline earth metal complex can be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. The ligand coordinated to the metal ion of the alkali metal complex or the ligand coordinated to the metal ion of the alkaline earth metal complex can each independently include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyl-oxazole, a hydroxyphenyl-thiazole, a hydroxyphenyl-oxadiazole, a hydroxyphenyl-thiadiazole, a hydroxyphenyl-pyridine, a hydroxyphenyl-benzimidazole, a hydroxyphenyl-benzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
[0522] In embodiments, the metal-containing material can include a Li complex. The Li complex can include, for example, compound ET-D1 (Liq) or compound ET-D2:
[0523]
[0524] The electron transport region can include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer can directly contact the second electrode 150.
[0525] 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 including different materials, or a multi-layer structure including multiple layers including different materials.
[0526] 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.
[0527] 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.
[0528] The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound can include an oxide, a halide (e.g., a fluoride, a chloride, a bromide, an iodide, etc.), or a telluride of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
[0529] The alkali metal-containing compound can include an alkali metal oxide such as Li2O, Cs2O, or K2O; an alkali metal halide such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI; or any combination thereof. The alkaline earth metal-containing compound can include an alkaline earth metal oxide such as BaO, SrO, CaO, Bax Sr 1-x O (wherein x is a real number satisfying 0 < x < 1) or Ba x Ca 1-x O (wherein x is a real number satisfying 0 < x < 1). 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 lanthanide tellurides. Examples of lanthanide tellurides 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.
[0530] The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex can include: an alkali metal ion, an alkaline earth metal ion, or a rare earth metal ion; and a ligand (e.g., a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyl-oxazole, a hydroxyphenyl-thiazole, a hydroxyphenyl-oxadiazole, a hydroxyphenyl-thiadiazole, a hydroxyphenyl-pyridine, a hydroxyphenyl-benzimidazole, a hydroxyphenyl-benzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof) bonded to the metal ion.
[0531] In embodiments, the electron injection layer can be composed of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal containing compound, an alkaline earth metal containing compound, a rare earth metal containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In embodiments, the electron injection layer can further include an organic material (e.g., a compound represented by Formula 601).
[0532] In embodiments, the electron injection layer can be composed of an alkali metal containing compound (e.g., an alkali metal halide); or the electron injection layer can be composed of an alkali metal containing compound (e.g., an alkali metal halide) and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer can be a KI:Yb co-deposited layer or a RbI:Yb co-deposited layer, etc.
[0533] When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal containing compound, the alkaline earth metal containing compound, the rare earth metal containing compound, the alkali metal complex, the alkaline earth metal complex, the rare earth metal complex, or any combination thereof can be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0534] 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 range described above.
[0535] [Second electrode 150]
[0536] The second electrode 150 may be disposed on the interlayer 130. The second electrode 150 may be a cathode serving as an electron injection electrode. When the second electrode 150 is a cathode, the second electrode 150 may comprise a material having a low work function, such as a metal, alloy, conductive compound, or any combination thereof.
[0537] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmission electrode, a transmission-reflection electrode, or a reflection electrode.
[0538] The second electrode 150 may have a single-layer structure or a multi-layer structure.
[0539] [Capping layer]
[0540] The light-emitting device 10 may include a first capping layer disposed outside the first electrode 110 and / or a second capping layer disposed outside the second electrode 150. In an embodiment, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked in the order described herein, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in the order described herein, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in the order described herein.
[0541] Light generated in the emitting layer of the interlayer 130 of the light-emitting device 10 can be extracted to the outside through a first electrode 110, which may be a transmissive or reflective electrode, and through a first capping layer. Light generated in the emitting layer of the interlayer 130 of the light-emitting device 10 can be extracted to the outside through a second electrode 150, which may be a transmissive or reflective electrode, and through a second capping layer.
[0542] The first capping layer and the second capping layer can each increase external emission efficiency according to the principle of constructive interference. Accordingly, 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.
[0543] The first capping layer and the second capping layer can each include a material having a refractive index equal to or greater than about 1.6 (with respect to a wavelength of about 589 nm).
[0544] The first capping layer and the second capping layer can each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
[0545] At least one of the first capping layer and the second capping 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 be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one of the first capping layer and the second capping layer can each independently include an amine-containing compound.
[0546] In an embodiment, 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.
[0547] In an embodiment, 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:
[0548]
[0549]
[0550] [Membrane]
[0551] The organometallic compound represented by Formula 1 can be included in various membranes.
[0552] Accordingly, according to an embodiment, a membrane can include the organometallic compound represented by Formula 1. The membrane can be, for example, an optical member (or a light control device) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarization layer, a quantum dot-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.
[0553] [Electronic device]
[0554] 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.
[0555] 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 disposed in at least one traveling direction of light emitted from the light emitting device. For example, the light emitted from the light emitting device can be blue light or white light. Further details regarding the light emitting device can be the same as described herein. In an embodiment, the color conversion layer can include quantum dots. The quantum dots can be, for example, quantum dots as described herein.
[0556] 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.
[0557] A pixel defining film can be disposed between the plurality of sub-pixels to define each sub-pixel.
[0558] The color filter can further include a plurality of color filter regions and a light blocking 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 blocking pattern disposed between the plurality of color conversion regions.
[0559] 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, where the first color light, the second color light, and / or the third color light can have different maximum emission wavelengths. 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 color conversion region) can include quantum dots. For example, 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. Further details regarding the quantum dots can be the same as described herein. The first region, the second region, and / or the third region can each further include a scatterer.
[0560] 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. 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.
[0561] In addition to the light-emitting device 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, where 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.
[0562] The thin film transistor can further include a gate electrode or a gate insulating film, etc.
[0563] The active layer can include crystalline silicon, amorphous silicon, an organic semiconductor, or an oxide semiconductor, etc.
[0564] The electronic device can further include a sealing portion for sealing the light-emitting device. The sealing portion can be arranged between the color filter and / or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and at the same time, prevents environmental air and 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 of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device can be flexible.
[0565] According to the use of the electronic device, various functional layers can be further included on the sealing portion in addition to the color filter and / or the color conversion layer. Examples of the functional layer can include a touch screen layer and a polarizing layer. 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 a biometric authentication device, for example, which authenticates an individual by using biometric information of a living body (e.g., a fingertip, a pupil, etc.).
[0566] In addition to the light-emitting device described above, the authentication device can further include a biometric information collector.
[0567] 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, etc.
[0568] [Electronic appliances]
[0569] The light-emitting device can be included in various electronic appliances.
[0570] In an embodiment, the electronic device 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 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 light therapy device, or a signboard.
[0571] Because the light emitting device has excellent effects in terms of light emitting efficiency and long lifespan, the electronic device including the light emitting device can have characteristics of high brightness, high resolution, and low power consumption.
[0572] [ Figure 2 and Figure 3 description]
[0573] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment.
[0574] Figure 2 The electronic device (e.g., a light emitting device) includes a substrate 100, a thin film transistor (TFT), a light emitting device, and a sealing part 300 sealing the light emitting device.
[0575] 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.
[0576] 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.
[0577] The active layer 220 can include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and the active layer 220 can include a source region, a drain region, and a channel region.
[0578] 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.
[0579] The 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 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240, the source electrode 260, and the drain electrode 270 from each other.
[0580] 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 the exposed portions of the source region and the drain region of the active layer 220, respectively.
[0581] The TFT can be electrically connected to the light emitting device to drive the light emitting device, and can be covered and protected by the 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 the first electrode 110, the interlayer 130, and the second electrode 150.
[0582] 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.
[0583] A pixel defining film 290 including an insulating material can be disposed on the first electrode 110. The pixel defining film 290 can expose a region of the first electrode 110, and the interlayer 130 can be formed in the exposed region of the first electrode 110. The pixel defining film 290 can be a polyimide-based organic film or a polyacrylic-based organic film. Although not shown in FIG. 1, at least some layers of the interlayer 130 can extend beyond the upper portion of the pixel defining film 290 to be provided in the form of a common layer. Figure 2
[0584] The second electrode 150 can be disposed on the interlayer 130, and a capping layer 170 can be further included on the second electrode 150. The capping layer 170 can be formed to cover the second electrode 150.
[0585] A sealing portion 300 can be located on the capping layer 170. The sealing portion 300 can be provided on the light emitting device to protect the light emitting device from moisture and / or oxygen. The sealing portion 300 can include an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyformaldehyde, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate and / or polyacrylic acid), an epoxy resin (e.g., an aliphatic glycidyl ether (AGE) ), or any combination thereof; or a combination of an inorganic film and an organic film.
[0586] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment.
[0587] Figure 3 The electronic device (e.g., a light emitting device) of Figure 2 The light emitting device of can differ at least in that the sealing part 300 further includes the light blocking pattern 500 and the functional area 400. The functional area 400 can be a color filter area, a color conversion area, or a combination of a color filter area and a color conversion area. In an embodiment, Figure 3 The light emitting device included in the electronic device of can be a serial light emitting device.
[0588] [ Figure 4 The description of
[0589] Figure 4 is a schematic perspective view of an electronic appliance 1 including a light emitting device according to an embodiment.
[0590] The electronic appliance 1 can be a device that displays a moving image or a still image, and can be not only a portable electronic appliance 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 appliance 1 can be any product as described above or a part thereof.
[0591] In an embodiment, the electronic appliance 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 a wearable device. However, embodiments are not limited thereto.
[0592] In an embodiment, an example of the electronic equipment 1 can include an instrument panel of a vehicle, a center information display (CID) arranged on a center console or an instrument panel of a vehicle, an in-vehicle rearview mirror display instead of a side mirror of a vehicle, an entertainment display for a rear seat of a vehicle, a display arranged on a backrest of a front seat of a vehicle, a head-up display (HUD) installed in a 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 equipment 1 is a smartphone is illustrated.
[0593] The electronic equipment 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 by a two-dimensional pixel array arranged in the display area DA.
[0594] The non-display area NDA is an area in which an image is not displayed, and can surround (for example, completely surround) the display area DA. A driver that supplies an electric signal or power to a display element arranged in the display area DA can be arranged in the non-display area NDA. A pad to which an electronic element or a printed circuit board can be electrically connected can be arranged in the non-display area NDA.
[0595] In the electronic equipment 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 shown in Figure 4 , the length in the x-axis direction can be smaller than the length in the y-axis direction. In an embodiment, the length in the x-axis direction can be the same as the length in the y-axis direction. In another embodiment, the length in the x-axis direction can be greater than the length in the y-axis direction.
[0596] [ Figure 5 and Figures 6A to 6C ]
[0597] Figure 5 is a schematic perspective view of the outside of a vehicle 1000 as an electronic equipment including a light emitting device according to an embodiment. Figures 6A to 6C Each is a schematic view of the inside of the vehicle 1000 according to an embodiment.
[0598] Referring to Figure 5 , Figure 6A , Figure 6B and Figure 6C , an embodiment of the vehicle 1000 can include 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. Examples of the vehicle 1000 can include a vehicle that travels on a road or a track, a ship that moves on an ocean or a river, and an airplane that flies in the air using air, etc.
[0599] The vehicle 1000 can travel on a road or a track. The vehicle 1000 can move in a selected or given direction according to rotation of at least one wheel. In an embodiment, 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.
[0600] The vehicle 1000 can include a body having an inside and an outside, and a chassis as a part other than the body in which mechanical devices required for driving are installed. The outside of the body 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 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.
[0601] The vehicle 1000 can include side window glasses 1100, a front window glass 1200, side mirrors 1300, an instrument panel 1400, a center console 1500, a passenger seat instrument panel 1600, and a display device 2.
[0602] The side window glasses 1100 and the front window glass 1200 can be divided by a pillar disposed between the side window glasses 1100 and the front window glass 1200.
[0603] The side window glasses 1100 can be installed on a side of the vehicle 1000. In an embodiment, the side window glasses 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 glasses 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.
[0604] In an embodiment, the side window glasses 1100 can be spaced apart from each other in an x-axis direction or a direction opposite to the x-axis direction. In an embodiment, 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 the 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 the 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 the direction opposite to the x-axis direction.
[0605] The front window glass 1200 can be installed at a front of the vehicle 1000. The front window glass 1200 can be disposed between the side window glasses 1100 facing each other.
[0606] The side mirror 1300 can provide a rear view of the vehicle 1000. The side mirror 1300 can be mounted on the outside of the 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 outside the first side window glass 1110, and another of the plurality of side mirrors 1300 can be disposed outside the second side window glass 1120.
[0607] The instrument panel 1400 can be disposed in front of the steering wheel. The instrument panel 1400 can include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn signal indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a speedometer, an automatic shift lever indicator, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0608] 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 provided. The center console 1500 can be disposed at a side of the instrument panel 1400.
[0609] 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.
[0610] In an embodiment, the display apparatus 2 can include a display panel 3, and the display panel 3 can display an image. The display apparatus 2 can be disposed inside the vehicle 1000. In an embodiment, the display apparatus 2 can be disposed between the side window glasses 1100 facing each other. The display apparatus 2 can be disposed on at least one of the instrument panel 1400, the center console 1500, and the passenger seat instrument panel 1600.
[0611] The display apparatus 2 can include an organic light emitting display apparatus, an inorganic electroluminescent display apparatus, or a quantum dot display apparatus, etc. Hereinafter, an organic light emitting display apparatus including a light emitting device according to an embodiment will be described as an example of the display apparatus 2. However, various types of display apparatuses as described above can be used in an embodiment.
[0612] Referring to Figure 6A , the display apparatus 2 can be disposed on the center console 1500. In an embodiment, the display apparatus 2 can display navigation information. In an embodiment, the display apparatus 2 can display information about an audio setting, a video setting, or a vehicle setting.
[0613] Referring toFigure 6B The display apparatus 2 can be disposed on the instrument panel 1400. The instrument panel 1400 can display driving information, etc. through the display apparatus 2. For example, the instrument panel 1400 can digitally implement driving information, etc. The instrument panel 1400 can digitally implement vehicle information and driving information as an image. In an embodiment, a needle of a tachometer and meters and various warning lamps or icons can be displayed through digital signals.
[0614] Reference Figure 6C The display apparatus 2 can be disposed on the passenger seat panel 1600. The display apparatus 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 apparatus 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 apparatus 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.
[0615] [Manufacturing method]
[0616] The layer constituting the hole transport zone, the emission layer, and the layer constituting the electron transport zone can be formed in a selected zone by using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging, etc.
[0617] When the layer constituting the hole transport zone, the emission layer, and the layer constituting the electron transport zone are formed by vacuum deposition, the deposition can be performed at a deposition temperature in the range of about 100°C to about 500°C, a vacuum degree in the range of about 10 -8 tor to about 10 -3 tor, and a deposition speed in the range of about to about , depending on the material to be included in the layer to be formed and the structure of the layer to be formed.
[0618] [Definition of terms]
[0619] The term "C3-C 60 carbocyclyl" as used herein can be a cyclic group consisting of carbon atoms as the only ring-forming atoms and having 3 to 60 carbon atoms. The term "C1-C 60 heterocyclyl" as used herein can be a cyclic group having 1 to 60 carbon atoms and further having at least one heteroatom as a ring-forming atom in addition to carbon atoms. C3-C 60 carbocyclyl" and "C1-C 60Heterocyclyl groups can each be monocyclic groups consisting of one ring or polycyclic groups in which two or more rings are fused with one another. In embodiments, C1-C 60 The number of ring-forming atoms in a heterocyclyl group can be 3 to 61.
[0620] As used herein, the term "cyclic group" can be a C3-C 60 carbocyclyl group or a C1-C 60 heterocyclyl group.
[0621] As used herein, the term "π-electron rich C3-C 60 cyclic group" can be a cyclic group having 3 to 60 carbon atoms and can not include *-N=* as a ring-forming moiety. As used herein, the term "π-electron deficient nitrogen-containing C1-C 60 heterocyclyl group" can be a heterocyclyl group having 1 to 60 carbon atoms and can include *-N=* as a ring-forming moiety.
[0622] C3-C 60 A carbocyclyl group can be a T1 group, or a group in which two or more T1 groups are fused with one another (e.g., a cyclopentadienyl group, an adamantyl group, a norbornyl group, a phenyl group, a pentacene group, a naphthyl group, an azulene group, an indacene group, a triphenylene group, a phenalenyl group, a phenanthrene group, an anthracene group, a fluoranthenyl group, a triphenylene group, a pyrene group, a 1,2- benzophenanthryl group, a perylene group, a pentaphene group, a heptacene group, a naphthacene group, a coronene group, a ovalene group, an indenyl group, a fluorene group, a spirobifluorene group, a benzofluorene group, an indenophenanthrene group, or an indenoanthracene group),
[0623] C1-C 60The heterocyclic group can be a T2 group, wherein two or more T2 groups are fused together, or wherein at least one T2 group and at least one T1 group are fused together (e.g., pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiophene, benzofuranyl, carbazole, dibenzothiophene, dibenzothiophene, dibenzofuranyl, indocarbazole, indolecarbazole, benzofuranocarbazole, benzothiophenecarbazole, benzothiophenecarbazole, benzoindocarbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthophene, benzonaphthothiophene, benzofuranodibenzofuranyl, benzofuranodibenzofuranyl). Thiophene, benzothiophene, dibenzothiophene, pyrazolyl, imidazole, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benzoisooxazolyl, benzothiazolyl, benzoisothiazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinoline, Phinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cenolinyl, phthalazinyl, naphthidyl, imidazopyridyl, imidazopyrimidyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazoyl, azafluorenyl, azadibenzothiophenyl, azadibenzofuranyl, etc.
[0624] C3-C rich in π electrons 60 The cyclic group may 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 at least one T3 group and at least one T1 group 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 or benzothiophene-dibenzothiophene, etc.
[0625] Nitrogen-containing C1-C lacking π electrons 60The heterocyclyl group can be a group in which two or more T4groups are fused to each other, a group in which at least one T4group and at least one T1group are fused to each other, a group in which at least one T4group and at least one T3group are fused to each other, or a group in which at least one T4group, at least one T1group, and at least one T3group are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, benzoisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiophenyl, and azadibenzofuranyl, etc.), wherein
[0626] 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,
[0627] 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, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl, or dihydropyridazinyl,
[0628] The T3group can be furanyl, thienyl, 1H-pyrrolyl, thiopyrrolyl, or borolyl, and
[0629] The T4group can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiopyrrolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or tetrazinyl.
[0630] Based on the structure of the formula using the corresponding terminology, such as the terms "cyclic group" and "C3-C" used in this article. 60 "Carbocyclic group", "C1-C" 60 Heterocyclic groups, π-electron-rich C3-C 60 "Cyclic groups" and "nitrogen-containing C1-C groups lacking π electrons" 60 "Heterocyclic group" can refer to any group fused with any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.). In embodiments, "phenyl" can be benzo[a], phenyl, or phenylene, etc., which can be readily understood by those skilled in the art based on the structure of formulas including "phenyl".
[0631] Unit price C3-C 60 Carbocyclic groups and monovalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups. Divalent C3-C 60 Carbocyclic groups and divalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkenyl, C6-C 60 aryl, C1-C 60 Hypoaryl, divalent non-aromatic fused polycyclic groups and divalent non-aromatic fused heterocyclic groups.
[0632] As used in this article, the term "C1-C" 60 "Alkyl" can be a straight-chain or branched monovalent aliphatic hydrocarbon group having 1 to 60 carbon atoms, and examples may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, and tert-decyl. The term "C1-C" as used herein... 60 "alkylene" can be C1-C 60 Alkyl groups have the same structure as divalent groups.
[0633] As used in this article, the term "C2-C" 60 "Alkenyl" can be in C2-C 60 The alkyl group has at least one carbon-carbon double bond at its middle or end, and examples may include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Alkenyl" can be C2-C 60 Alkenes have divalent groups with the same structure.
[0634] As used in this article, the term "C2-C" 60 "Alkyne group" can be at C2-C 60 The alkyl group has at least one monovalent hydrocarbon group with a carbon-carbon triple bond in the middle or at the end, and examples may include ethynyl and propynyl groups. 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.
[0635] 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.
[0636] 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.
[0637] 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. 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.
[0638] As used in this article, the term "C3-C" 10"Cycloalkenyl" can be a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its cyclic structure, and is non-aromatic, and examples may include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C3-C" is used as is herein. 10 "Iridylene" can be related to C3-C 10 Cycloalkenyl groups are divalent groups with the same structure.
[0639] 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. The term "C1-C" is used herein. 10 "Heterocyclic alkenyl" can be C1-C 10 Heterocyclic alkenyl groups are divalent groups with the same structure.
[0640] 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, anthrayl, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentanenyl, heptanenyl, tetraphenyl, framyl, hexaphenyl, pentaphenyl, rubiginyl, myristyl, and ovoleyl. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the two or more rings can fused together.
[0641] 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. As used herein, the term "C1-C" is used in this context. 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 may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzo[a]quinolinyl, isoquinolinyl, benzo[a]isoquinolinyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, cyclolinyl, phenanthrolinel, phthalazinyl, and naphthidyl. When C1-C 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the two or more rings can fused together.
[0642] As used herein, the term "monovalent nonaromatic fused polycyclic group" can be a monovalent group having two or more rings fused together, with only carbon atoms (e.g., having 8 to 60 carbon atoms) as cyclic atoms, and having no aromaticity in its molecular structure when considered as a whole. Examples of monovalent nonaromatic fused polycyclic groups may include indenyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, indo[a]phenanthryl, and indo[a]anthrayl. As used herein, the term "divalent nonaromatic fused polycyclic group" can be a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.
[0643] As used herein, the term “monovalent nonaromatic fused heterocyclic group” can be a monovalent group having two or more rings fused together, further including at least one heteroatom as a cyclic atom in addition to carbon atoms (e.g., 1 to 60 carbon atoms), and having no aromaticity in its molecular structure when considered as a whole. Examples of monovalent non-aromatic fused heterocyclic groups may include pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiophene, benzofuranyl, carbazole, dibenzothiophene, dibenzofuranyl, azacarbazole, azafluorenyl, azadibenzothiophene, azadibenzothiophene, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, isothiazolyl, oxadiazolyl, thiazolyl Benzopyrazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, benzooxadiazolyl, benzothiadiazolyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indolecarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzothiophenocarbazolyl, benzoindolocarbazolyl, benzocarbazolyl, benzonaphthiophenyl, benzonaphthiophenyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, and benzothiophenodibenzothiophenyl. As used herein, the term "divalent nonaromatic fused heteropolycyclic group" can refer to a divalent group having the same structure as a monovalent nonaromatic fused heteropolycyclic group.
[0644] As used in this article, the term "C6-C" 60Aryloxy" can be a radical represented by -O(A 102 )(wherein A 102 may be a C6-C 60 aryl group), and as used herein the term "C6-C 60 Arylthio" can be a radical represented by -S(A 103 )(wherein A 103 may be a C6-C 60 aryl group).
[0645] As used herein the term "C7-C 60 Aralkyl" can be a radical represented by -(A 104 )A 105 )(wherein A 104 may be a C1-C 54 alkylene group, and A 105 may be a C6-C 59 aryl group), and as used herein the term "C2-C 60 Heteroaralkyl" can be a radical represented by -(A 106 )(A 107 )(wherein A 106 may be a C1-C 59 alkylene group, and A 107 may be a C1-C 59 heteroaryl group).
[0646] In the description, the group "R 10a " can be:
[0647] deutero, -F, -CI, -Br, -I, hydroxyl, cyano, or nitro;
[0648] each unsubstituted or substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy: deutero, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbocyclyl, C1-C 60 heterocyclyl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0649] each unsubstituted or substituted with C3-C 60 carbocyclyl, C1-C 60 heterocyclyl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, C7-C 60 aralkyl, or C2-C 60 heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclyl, C1-C 60 heterocyclyl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ) or any combination thereof; or
[0650] -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q31 -S(=O)2(Q) 31 ) or -P(=O)(Q 31 (Q) 32 ).
[0651] In the instruction manual, 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; or 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 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups.
[0652] As used herein, the term "heteroatom" can refer to any atom other than carbon and hydrogen. Examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, and any combination thereof.
[0653] Examples of "transition metals" in the specification may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and gold (Au).
[0654] In the specification, the term "Ph" refers to phenyl, the term "Me" refers to methyl, the term "Et" refers to ethyl, and the terms "tert-Bu" and "Bu" are used interchangeably. t Each refers to tert-butyl, and the term "OMe" refers to methyl methacrylate (MMA).
[0655] As used herein, the term "biphenyl" can mean "phenyl substituted with a phenyl group." For example, "biphenyl" can refer to a phenyl group having a C6-C ratio. 60 Aryl groups are substituted phenyl groups.
[0656] As used herein, the term "terphenyl" can mean "phenyl substituted with biphenyl." For example, "terphenyl" can be a phenyl group having a C6-C substituted structure. 60 Aryl-substituted C6-C 60 Aryl groups are substituted phenyl groups.
[0657] In the specification, unless otherwise defined, the symbols *, * and * each indicate a bonding site to an adjacent atom in a corresponding formula or moiety.
[0658] 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, y-axis, and z-axis can describe axes that are orthogonal to each other, or can describe axes in different directions that are not orthogonal to each other.
[0659] As used herein, the term "C3-C 60 C3-C 50 C3-C 40 C3-C 30 C3-C 20 C3-C 10 C3-C
[0660] The term "C1-C 60 C1-C 50 C1-C 40 C1-C 30 C1-C 20 C1-C 10 C1-C
[0661] The term "C1-C 60 C1-C 50 C1-C 30 C1-C 20 C1-C 10 C1-C
[0662] The term "C2-C 60 C2-C 30 C2-C 20 C2-C 10 C2-C
[0663] The term "C2-C 60 C2-C 30 C2-C 20 C2-C 10 C2-C
[0664] The term "C1-C 60 C1-C 30 C1-C 20 C1-C 10alkoxy;
[0665] 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;
[0666] 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;
[0667] The term "monovalent non-aromatic fused multicyclic group" includes C8-C 60 monovalent non-aromatic fused multicyclic group, C8-C 50 monovalent non-aromatic fused multicyclic group, C8-C 40 monovalent non-aromatic fused multicyclic group, C8-C 30 monovalent non-aromatic fused multicyclic group or C8-C 20 monovalent non-aromatic fused multicyclic group;
[0668] 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;
[0669] The term "C6-C 60 aryloxy" includes C6-C 50 aryloxy, C6-C 40 aryloxy, C6-C 30 aryloxy, C6-C 20 aryloxy or C6-C 15 aryloxy;
[0670] The term "C6-C 60 arylthio" includes C6-C 50 arylthio, C6-C 40 arylthio, C6-C 30 arylthio, C6-C 20 arylthio or C6-C15 arylthio;
[0671] The term "C7-C 60 aralkyl" includes C7-C 50 aralkyl, C7-C 40 aralkyl, C7-C 30 aralkyl, C7-C 20 aralkyl or C7-C 15 aralkyl; and
[0672] The term "C2-C 60 heteroaralkyl" includes C2-C 50 heteroaralkyl, C2-C 40 heteroaralkyl, C2-C 30 heteroaralkyl, C2-C 20 heteroaralkyl or C2-C 15 heteroaralkyl.
[0673] In the specification, "an integer selected from 0 to 20" means an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20. 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, an integer selected from 0 to 10, an integer selected from 0 to 11, an integer selected from 0 to 12, an integer selected from 0 to 13, an integer selected from 0 to 14, an integer selected from 0 to 15, an integer selected from 0 to 16, an integer selected from 0 to 17, an integer selected from 0 to 18, and an integer selected from 0 to 19, and the like.
[0674] Hereinafter, the compound according to the embodiment and the light-emitting device according to the embodiment will be described in detail with reference to the following synthesis examples and examples. The phrase "use B instead of A" used in describing the synthesis examples means replacement of A with B in the same molar equivalent.
[0675] [Examples]
[0676] [Synthesis Example 1: Synthesis of Compound 1]
[0677]
[0678] (Synthesis of Intermediate 1-a)
[0679] Dissolved 9-bromoanthracene (1.0 equivalent) and anthracene (10 equivalents) in toluene (0.1 M) and irradiated with a xenon lamp at 110°C for 12 hours under a nitrogen atmosphere and stirred to obtain a reaction product. The reaction product was cooled to room temperature and a three-time extraction process was performed using ethyl acetate (EA) and water to obtain an organic layer. The organic layer thus obtained was dried by using magnesium sulfate and concentrated, and column chromatography (EA:hexane = 1:50 by volume) was used to obtain the intermediate compound 1-a (yield: 83%).
[0680] (Synthesis of intermediate 1-b)
[0681] Dissolved intermediate 1-a (1.0 equivalent), bis(diphenylphosphino)ferrocene palladium dichloride (Pd(dppf)Cl2, 0.05 equivalent), bis(pinacolato)diboron (B2(pin)2, 1.5 equivalents), and potassium acetate (3.0 equivalents) in 1,4-dioxane and stirred at 100°C overnight to obtain a reaction product. After cooling the reaction product to room temperature, distilled water was added thereto, and a three-time extraction process was performed thereon by using EA to obtain an organic layer. The organic layer thus obtained was dried by using magnesium sulfate and concentrated, and column chromatography (EA:hexane = 1:50 by volume) was used to obtain intermediate 1-b (yield: 72%).
[0682] (Synthesis of intermediate 1-b)
[0683] Dissolved intermediate 1-b (1.0 equivalent), CX31 (Umicore, 0.05 equivalent), potassium carbonate (3.0 equivalents), and 3-bromo-3',5'-di-tert-butyl-(1,1'-biphenyl)-2-amine (1.2 equivalents) in 1,4-dioxane:water (volume ratio of 1,4-dioxane:water = 3:1) and stirred at 100°C for 18 hours to obtain a reaction product. After cooling the reaction product to room temperature, distilled water was added thereto, and a three-time extraction process was performed thereon by using EA to obtain an organic layer. The organic layer thus obtained was dried by using magnesium sulfate and concentrated, and column chromatography (MC:hexane = 10:90 by volume) was used to obtain intermediate 1-c (yield: 65%).
[0684] (Synthesis of intermediate 1-b)
[0685] Intermediate 1-c (1.0 equivalent), 1-bromo-2-nitrobenzene (2 equivalents), 2- dicyclohexylphosphino-2',6'-dimethoxybiphenyl (Sphos, 0.10 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.05 equivalent), and sodium tert-butoxide (NaOtBu, 3 equivalents) were dissolved in toluene and stirred at 110°C for 16 hours to obtain a reaction product. After the reaction product was cooled to room temperature, distilled water was added thereto, and a three-time extraction process was performed thereto by using EA to obtain an organic layer. The organic layer thus obtained was dried by using magnesium sulfate and concentrated, and column chromatography (MC: volume ratio of hexane = 10:90) was used to obtain intermediate 1-d (yield: 75%).
[0686] (Synthesis of intermediate 1-e)
[0687] Intermediate 1-d (1.0 equivalent) and tin (5 equivalents) were dissolved in ethanol (EtOH) and stirred. Hydrogen chloride (12M) was added thereto, and the mixture was stirred at 80°C for 20 hours to obtain a reaction product. After the reaction product was cooled to room temperature, distilled water was added thereto, and a three-time extraction process was performed thereto by using EA to obtain an organic layer. The organic layer thus obtained was dried by using magnesium sulfate and concentrated, and column chromatography (MC: volume ratio of hexane = 10:90) was used to obtain intermediate 1-e (yield: 73%).
[0688] (Synthesis of intermediate 1-f)
[0689] Intermediate 1-e (1.0 equivalent), 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H- carbazole (1.0 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.05 equivalent), XPhos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 0.10 equivalent), and sodium tert-butoxide (2.0 equivalents) were dissolved in 1,4-dioxane (0.1M) and stirred at 110°C for 3 hours to obtain a reaction product. After the reaction product was cooled to room temperature, distilled water was added thereto, and a three-time extraction process was performed thereto by using EA to obtain an organic layer. The organic layer thus obtained was dried by using magnesium sulfate and concentrated, and column chromatography (MC: volume ratio of hexane = 10:90) was used to obtain intermediate 1-f (yield: 71%).
[0690] (Synthesis of intermediate 1-g)
[0691] The intermediate 1-f (1.0 equivalent) was dissolved in triethyl orthoformate (30 equivalents), and thereto was added 37% HCl (1.5 equivalents), followed by stirring at 80°C overnight to obtain a reaction product. After cooling the reaction product at room temperature, and removing triethyl orthoformate in the reaction product, distilled water was added thereto, and it was subjected to a three-time extraction process by using EA to obtain an organic layer. The thus obtained organic layer was dried by using magnesium sulfate and concentrated, and column chromatography (MC: volume ratio of methanol = 98:2) was used to obtain the intermediate 1-g (yield: 82%).
[0692] (Synthesis of Compound 1)
[0693] The intermediate 1-g (1.0 equivalent), potassium tetrachloroplatinate (II) (K2PtCl4, 1.1 equivalent), and 2,6-dimethylpyridine (4.0 equivalents) were dissolved in 1,2-dichlorobenzene (o-DCB, 0.05 M), and stirred at 120°C overnight in a nitrogen atmosphere to obtain a reaction product. After cooling the reaction product at room temperature, and concentrating and removing 1,2-dichlorobenzene in the reaction product, distilled water was added thereto, and it was subjected to a three-time extraction process by using EA to obtain an organic layer. The thus obtained organic layer was dried by using magnesium sulfate and concentrated, and column chromatography (MC: volume ratio of hexane = 10:90) was used to obtain Compound 1 (yield: 59%).
[0694] [Synthesis Example 2: Synthesis of Compound 3]
[0695]
[0696] Compound 3 was synthesized in a substantially similar manner to the synthesis of Compound 1 (yield: 64%), except that 2-(3-bromophenoxy)-9-(4-(methyl-d3)pyridin-2-yl)-9H-carbazole was used instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole in the synthesis of the intermediate 3-f.
[0697] [Synthesis Example 3: Synthesis of Compound 9]
[0698]
[0699] Compound 9 was synthesized in a substantially similar manner to the synthesis of Compound 1 (yield: 55%), except that 1-bromoanthracene was used instead of 9-bromoanthracene in the synthesis of the intermediate 9-a, and 2-(3-bromophenoxy)-9-(5-(3-(tert-butyl)phenyl)pyridin-2-yl)-9H-carbazole was used instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole in the synthesis of the intermediate 9-f.
[0700] [Synthesis Example 4: Synthesis of Compound 17]
[0701]
[0702] Compound 17 was synthesized in substantially the same manner as the synthesis of Compound 1 (yield: 58%), except that 2-bromoanthracene was used instead of 9-bromoanthracene in the synthesis of intermediate 17-a; and 2-(3-bromophenoxy)-9-(5-(3-(tert-butyl)phenyl)-4-(methyl-d3)pyridin-2-yl)-9H-carbazole was used instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole in the synthesis of intermediate 17-f.
[0703] [Synthesis Example 5: Synthesis of Compound 21]
[0704]
[0705] Compound 21 was synthesized in substantially the same manner as the synthesis of Compound 1 (yield: 60%), except that 2-bromoanthracene was used instead of 9-bromoanthracene in the synthesis of intermediate 21-a; and 2-(3-bromophenoxy)-9-(5-(3-(tert-butyl)phenyl)-4-(methyl-d3)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 was used instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole in the synthesis of intermediate 21-f.
[0706] [Synthesis Example 6: Synthesis of Compound 29]
[0707]
[0708] Compound 29 was synthesized in substantially the same manner as the synthesis of Compound 1 (yield: 49%), except that 9-phenylanthracene was used instead of anthracene in the synthesis of intermediate 29-a; and 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 was used instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole in the synthesis of 29-f.
[0709] [Synthesis Example 7: Synthesis of Compound 33]
[0710]
[0711] Compound 33 was synthesized in a substantially similar manner to the synthesis of Compound 1 (yield: 55%) except that 2-bromoanthracene was used instead of 9-bromoanthracene in the synthesis of intermediate 33-a; and 2-(3-bromophenoxy)-9-(5-(3-(tert-butyl)phenyl)pyridin-2-yl)-9H-carbazole was used instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole in the synthesis of intermediate 33-f.
[0712] [Synthesis Example 8: Synthesis of Compound 37]
[0713]
[0714] Compound 37 was synthesized in a substantially similar manner to the synthesis of Compound 1 (yield: 61%) except that 9,10-diphenylanthracene was used instead of anthracene in the synthesis of intermediate 37-a, 3-bromo-3',5,5'-tri-tert-butyl-[1,1'-biphenyl]-2-amine was used instead of 3-bromo-3',5'-di-tert-butyl-(1,1'-biphenyl)-2-amine in the synthesis of intermediate 37-c; and 2-(3-bromophenoxy)-9-(4-(tert-butyl)-5-(3-(tert-butyl)phenyl)pyridin-2-yl)-9H-carbazole was used instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole in the synthesis of intermediate 37-f.
[0715] [Synthesis Example 9: Synthesis of Compound 66]
[0716]
[0717] Compound 66 was synthesized in a substantially similar manner to the synthesis of Compound 1 (yield: 55%) except that 1-bromoanthracene and 9,10-dimethylanthracene were used instead of 9-bromoanthracene and anthracene, respectively, in the synthesis of intermediate 66-a; 3-bromo-3',5'-bis(methyl-d3)-[1,1'-biphenyl]-2-amine was used instead of 3-bromo-3',5'-di-tert-butyl-(1,1'-biphenyl)-2-amine in the synthesis of intermediate 66-c; and 2-(3-bromo-4-(methyl-d3)phenoxy)-9-(5-(4-(tert-butyl)phenyl)-4-(methyl-d3)pyridin-2-yl)-9H-carbazole was used instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole in the synthesis of intermediate 66-f.
[0718] [Synthesis Example 10: Synthesis of Compound 116]
[0719]
[0720] Compound 116 was synthesized in a substantially similar manner to the synthesis of Compound 1, except that 9-bromo-2,7-dimethylanthracene was used instead of 9-bromoanthracene in the synthesis of intermediate 116-a; 3-bromo-5-(tert-butyl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-2-amine was used instead of 3-bromo-3',5'-di-tert-butyl-(1,1'-biphenyl)-2-amine in the synthesis of intermediate 116-c; and 2-(3-bromophenoxy)-9-(5-(methyl-d3)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 was used instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole in the synthesis of intermediate 116-f (yield: 58%).
[0721] For the compounds synthesized in Synthesis Example 1 to Synthesis Example 10, 1H NMR and high resolution mass spectrum (HR-MS) were measured, and the results are shown in Table 1. Those skilled in the art can easily recognize the synthesis methods of other compounds other than the compounds synthesized in Synthesis Example 1 to Synthesis Example 10, with reference to these synthesis routes and starting materials.
[0722] [Table 1]
[0723]
[0724]
[0725] [Assessment Example 1: Assessment of properties of organometallic compounds]
[0726] The HOMO level value and LUMO level value and the maximum emission wavelength of Compound 1, Compound 3, Compound 9, Compound 17, Compound 21, Compound 29, Compound 33, Compound 37, Compound 66, and Compound 116, and Comparative Compound A and Comparative Compound B were measured according to the method shown in Table 2, and the results thereof are shown in Table 3.
[0727] [Table 2]
[0728]
[0729] [Table 3]
[0730]
[0731]
[0732] [Example 1]
[0733] A 15 Ω / cm2 The indium tin oxide (ITO) glass substrate (a Corning product) was cut to a size of 50mm × 50mm × 0.7mm, ultrasonically treated with isopropanol and pure water for 5 minutes each, rinsed by irradiation with ultraviolet light and exposure to ozone for 30 minutes, and then mounted on a vacuum deposition equipment.
[0734] 2-TNATA was vacuum deposited onto the anode to form a structure with... A hole injection layer of a certain thickness was formed, and 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as "NPB") was vacuum deposited on the hole injection layer to form a hole injection layer with a certain thickness. A hole transport layer of a certain thickness.
[0735] Compound 1 (an organometallic compound represented by Formula 1), compound ETH66 (the second compound), and compound HTH29 (the third compound) were vacuum deposited on the hole transport layer to form a structure with... The emitter layer has a thickness of 13 wt%. Here, based on the total weight of the emitter layer (100 wt%), the amount of compound 1 is 13 wt%, and the weight ratio of compound ETH66 to compound HTH29 is adjusted to 3.5:6.5.
[0736] Compound ETH34 was vacuum-deposited onto the emitter layer to form a structure with... A hole-blocking layer of a certain thickness was formed, and compounds ET46 and Liq were vacuum-deposited onto the hole-blocking layer at a weight ratio of 4:6 to form a hole-blocking layer with a certain thickness. An electron transport layer of a certain thickness. Yb is vacuum deposited onto the electron transport layer to form an electron transport layer with... An electron-injected layer of a certain thickness is formed, and Mg is vacuum-deposited on it to form a layer with [missing information]. A cathode of a certain thickness is used to complete the manufacturing of the light-emitting device.
[0737]
[0738] [Examples 2 to 10, and Comparative Examples 1 and 2]
[0739] The light-emitting device was manufactured in a manner substantially similar to that of Example 1, except that the compounds in Table 4 were used instead of compound 1 when forming the emitting layer.
[0740] [Evaluation Example 2: Evaluation of the characteristics of a light-emitting device]
[0741] The light-emitting devices manufactured in Examples 1 to 10, and Comparative Examples 1 and 2, were measured at 1000 cd / m² using a Keithley MU 236 and a PR650 luminance meter, respectively. 2 Driving voltage, luminous efficiency, maximum emission wavelength and lifetime (T)95 ). The results are shown in Table 4. In Table 4, the lifetime (T 95 ) is the time (hours) taken for the measured luminance to reach 95% of the initial luminance from the initial luminance.
[0742] [Table 4]
[0743]
[0744] As shown in Table 4, it was confirmed that the light-emitting devices of Embodiments 1 to 10 have superior luminous efficiency and lifetime characteristics compared to the light-emitting devices of Comparative Examples 1 and 2.
[0745] By using the organometallic compound represented by Formula 1, a light-emitting device having improved color purity, high luminous efficiency, and long lifetime, and a high-quality electronic device and electronic equipment including the light-emitting device can be manufactured.
[0746] 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, in light of the overall disclosure, various changes and modifications can be made therein without departing from the spirit and scope of the disclosure as set forth in the claims.
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 emission layer; and an organometallic compound represented by Formula 1: Formula 1 Formula 1A wherein in Formula 1, A is a group represented by Formula 1A, wherein in Formula 1 and Formula 1A, M is platinum, palladium, gold, nickel, silver, or copper, X1to X4are each independently C or N, the bond between X1and M is a coordinate bond, one of the bonds between X2and M, the bond between X3and M, and the bond between X4and M is a coordinate bond, and the remaining two thereof are each a covalent bond, n1to n3are each independently an integer selected from 1 to 5, each of the rings CY1to CY4, Ar1to Ar4, and Ar7is independently C3-C 60 carbocyclyl or C1-C 60 heterocyclyl, L1to L3are each independently a single bond, *-C(R 1a )(R 1b )-*, *-C(R 1a )=*, *=C(R 1a )-*, *-C(R 1a )=C(R 1b )-*, *-C(=0)-*, *-C(=S)-*, *-C=C-*, *-B(R 1a )-*, *-N(R 1a )-*, *-0-*, *-P(R 1a )-*, *-Si(R 1a )(R 1b )-*, *-P(=0)(R 1a )-*, *-S-*, *-S(=0)-*, *-S(=0)2-*, or *-Ge(R 1a )(R 1b )-*, wherein each of *and *indicates a bonding site to an adjacent atom, a1to a4are each independently an integer selected from 0 to 10, R1to R4, R 1a , R 1b , T1to T4, T 51 to T 54 , T 61 to T 63 , and T7are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted with at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted with at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted with at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclyl, unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclyl, unsubstituted or substituted with at least one R 10a substituted C6-C 60 aryloxy, unsubstituted or substituted with at least one R 10a substituted C6-C 60 arylthio, unsubstituted or substituted with at least one R 10a substituted C7-C 60 aralkyl, unsubstituted or substituted with at least one R 10a substituted C2-C 60 heteroaralkyl, -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), b1to b4and b7are each independently an integer selected from 0 to 10, * in Formula 1A indicates a binding site to the ring CY1in Formula 1, R1 to R4, T1 to T4, T 51 To T 54 T 61 To T 63 And two or more of T7 are optionally bonded together to form an unsubstituted or R-type compound. 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, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, or a nitro group; R 10a is:
2. The light-emitting device of 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 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, 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 by: 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, 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; or 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, 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 emission layer; and an electron transport region between the emission layer and the second electrode, the hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
3. The light-emitting device of claim 1, wherein the emission layer includes the organometallic compound represented by Formula 1.
4. The light-emitting device of claim 1, wherein the emission layer includes a host and a dopant, and the dopant includes the organometallic compound represented by Formula 1.
5. The light-emitting device of claim 4, wherein the dopant further includes a delayed fluorescence material.
6. The light-emitting device of claim 4, wherein the host includes a first host compound and a second host compound, the first host compound is a hole transport host, the hole transport host is represented by one of Formulae 311-1 to 311-6, the second host compound is an electron transport host, and the electron transport host is represented by one of Formulae 312-1 to 312-4 and 313: Formula 311-1 Formula 311-2 Formula 311-3 Formula 311-4 Formula 311-5 Formula 311-6 Formula 312-1 Formula 312-2 Formula 312-3 Formula 312-4 Formula 313 Formula 313A wherein in Formulae 311-1 to 311-6, Formulae 312-1 to 312-4, Formula 313, and Formula 313A, xb1to xb5are each independently 0, 1, 2, 3, 4, or 5, xb6is 1, 2, 3, 4, or 5, Ar 301 unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclyl or unsubstituted or substituted C1-C 10a substituted C1-C 60 heterocyclyl, A 301 to A 304 each independently C3-C 60 carbocyclyl or C1-C 60 heterocyclyl, X 301 is O, S, N[(L 304 ) xb4 -R 304 ], C[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ] or Si[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ], X 302 , Y 301 and Y 302 are each independently a single bond, O, S, N[(L 305 ) xb5 -R 305 ], C[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ], Si[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ] or S(=O)2, xb21to xb26are each independently 0, 1, 2, 3, 4, or 5, xb31to xb36are each independently 0, 1, 2, 3, 4, or 5, X 321 to X 328 each independently N or C[(L 324 ) xb24 -R 324 ], Y 321 is *-O-*', *-S-*', *-N[(L 325 ) xb25 -R 325 ]-*' or *-C[(L 325 ) xb25 -R 325 ][(L 326 ) xb26 -R 326 ]-*' or *-C[(L 325 ) xb25 -R 325 ] = C[(L 326 ) xb26 -R 326 ]-*' or *-C[(L 325 ) xb25 -R 325 ] = N-*' or *-N = C[(L 326 ) xb26 -R 326 ]-*' k21 is 0, 1, or 2, wherein when k21 is 0, Y 321 is absent, A 31 , A 32 and A 34 are each independently C3-C 60 carbocyclyl or C1-C 30 heterocyclyl, A 33 is a group represented by formula 313A, X 31 is N[(L 335 ) xb35 -(R 335 )], O, S, Se, C[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )] or Si[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )], each of xb42 to xb44 is independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, L 301 To L 306 L 321 To L 326 and L 331 To L 336 Each is independently a single bond, unsubstituted, or affected 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 C2-C 20 alkyne group, unsubstituted or with at least one R 10a Replacement C3-C 10 Cycloalkylene, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkenyl, unsubstituted or with at least one R 10a Replacement C1-C 10 Heterocyclic alkenyl, unsubstituted or with at least one R 10a Replacement C6-C 60 aryl, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Substituted divalent nonaromatic fused polycyclic groups or unsubstituted groups or groups modified by at least one R 10a Substituted divalent non-aromatic fused heterocyclic groups, R 301 To R 305 R 311 To R 314 R 321 To R 326 and R 331 To R 336 Each of these groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, 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 10 Cycloalkyl, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkenyl, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkenyl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl thiols, unsubstituted or with at least one R 10a Substituted monovalent nonaromatic fused polycyclic groups, unsubstituted or substituted with at least one R 10a a substituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), R 321 To R 326 Two or more adjacent groups in a compound are optionally bonded to each other to form an unsubstituted compound or a compound with at least one R group. 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, R 10a for: hydrogen, deuterium, -F, -Cl, -Br, or -I; 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, 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 by: 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, 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; or 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, C1-C 60 heterocyclyl, C7-C 60 aralkyl, or C2-C 60 heteroaralkyl.
7. An electronic device comprising the light-emitting device according to any one of claims 1 to 6.
8. An electronic appliance comprising the light-emitting device according to any one of claims 1 to 6.
9. An organometallic compound represented by Formula 1: Formula 1 Formula 1A wherein in Formula 1, A is a group represented by Formula 1A, wherein in Formula 1 and Formula 1A, M is platinum, palladium, gold, nickel, silver, or copper, each of X1to X4is independently C or N, the bond between X1and M is a coordinate bond, one of the bonds between X2and M, the bond between X3and M, and the bond between X4and M is a coordinate bond, and the remaining two thereof are each a covalent bond, each of the rings CY1to CY4, Ar1to Ar4, and Ar7is independently C3-C 60 carbocyclyl or C1-C 60 heterocyclyl, L1 to L3 are each independently a single bond, *-C(R) 1a (R) 1b )-*'、*-C(R 1a )=*'、*=C(R 1a )-*'、*-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*'、*-N(R 1a )-*'、*-O-*'、*-P(R 1a )-*'、*-Si(R 1a (R) 1b )-*'、*-P(=O)(R 1a )-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R 1a (R) 1b )-*', where * and *' each indicate a binding site with an adjacent atom. each of n1to n3is independently an integer selected from 1 to 5, R1 to R4, R 1a R 1b T1 to T4, T 51 To T 54 T 61 To T 63 T7 and T7 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or modified by 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, 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), each of a1to a4is independently an integer selected from 0 to 10, each of b1to b4and b7is independently an integer selected from 0 to 10, R1 to R4, T1 to T4, T 51 To T 54 T 61 To T 63 Two or more of T7 are optionally bonded to each other to form an unsubstituted or R-terminated compound. 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, *in Formula 1A indicates a binding site to the ring CY1in Formula 1, R 10a is: hydrogen, deuterium, -F, -Cl, -Br, or -I; 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, 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 by: 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, 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, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, 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; or 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, C1-C 60 heterocyclyl, C7-C 60 aralkyl, or C2-C 60 heteroaralkyl.
10. The organometallic compound according to claim 9, wherein in Formula 1A, The moiety represented by and the moiety represented by are different from each other, and *indicates a binding site to an adjacent atom.
11. The organometallic compound according to claim 9, wherein X1is C, and the ring CY1is an imidazolyl group, a triazolyl group, a benzoimidazolyl group, a naphthoimidazolyl group, or an imidazopyridinyl group.
12. The organometallic compound of claim 9, wherein in formula 1, by The part represented is one of the parts represented by equations CY1(1) to CY1(5): wherein in Formula CY1(1) to Formula CY1(5), A is the same as defined in Formula 1, X 11 is C(R 11 ) or N, X 12 is C(R 12 ) or N, X 13 is C(R 13 ) or N, X 14 is C(R 14 ) or N, X 15 is C(R 15 ) or N, X 16 is C(R 16 ) or N, R 11 to R 16 each independently the same as defined in relation to R1in Formula 1, and *and *' each indicate a binding site to an adjacent atom.
13. The organometallic compound of claim 9, wherein R1through R4, R 1a , R 1b , T1through T4, T 51 through T 54 , T 61 through T 63 , and T7are each independently: hydrogen, deuterium, -F, -Cl, -Br, or -I; Unsubstituted or substituted C1-C 20 Alkyl groups: 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, pyrimidinyl, or any combination thereof; or each unsubstituted or substituted phenyl, biphenyl, terphenyl, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, C1-C 20 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, C1-C 14. The organometallic compound according to claim 9, wherein each of T1to T4is independently: hydrogen, deuterium, -F, or -Cl; or hydrogen, deuterium, -F, or -Cl; or C1-C6alkyl unsubstituted or substituted with deuterium, -F, cyano, or any combination thereof; 20 alkyl.
15. The organometallic compound according to claim 9, wherein each of the rings CY2 to CY4 is independently phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, thienyl, furanyl, indolyl, benzoborolyl, benzophospholyl, indenyl, benzothiazolyl, benzogermanolyl, benzothienyl, benzoselenophenyl, benzofuranyl, carbazolyl, dibenzoborolyl, dibenzophospholyl, fluorenyl, dibenzothiazolyl, dibenzogermanolyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuranyl, dibenzothiophene-5-oxideyl, 9H-fluoren-9-onyl, dibenzothiophene-5,5-dioxideyl, azaindolyl, azabenzoborolyl, azabenzophospholyl, azaindenyl, azabenzothiazolyl, azabenzogermanolyl, azabenzothienyl, azabenzoselenophenyl, azabenzofuranyl, azacarbazolyl, azadibenzoborolyl, azadibenzophospholyl, azafiuorenyl, azadibenzothiazolyl, azadibenzogermanolyl, azadibenzothienyl, azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophene-5-oxideyl, azo-9H-fluoren-9-onyl, azadibenzothiophene-5,5-dioxideyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolyl, or 5,6,7,8-tetrahydroquinolyl.
16. The organometallic compound according to claim 9, wherein in Formula 1, A is a group represented by one of Formula 1A-11 to Formula 1A-17: Formula 1A-11 Formula 1A-12 Formula 1A-13 Formula 1A-14 Formula 1A-15 Formula 1A-16 Formula 1A-17 wherein in Formula 1A-11 to Formula 1A-17, * indicates a binding site to the ring CY1 in Formula 1.
17. The organometallic compound according to claim 9, wherein in Formula 1, A is a group represented by one of Formula 1A-21 to Formula 1A-27: Formula 1A-21 Formula 1A-22 Formula 1A-23 Formula 1A-24 Formula 1A-25 Formula 1A-26 Formula 1A-27 wherein in Formula 1A-21 to Formula 1A-27, * indicates a binding site to the ring CY1 in Formula 1. Y 11 is N or C(T 11 ), Y 12 is N or C(T 12 ), Y 13 is N or C(T 13 ), Y 14 is N or C(T 14 ), Y 21 is N or C(T 21 ), Y 22 is N or C(T 22 ), Y 23 is N or C(T 23 ), Y 24 is N or C(T 24 ), Y 31 is N or C(T 31 ), Y 32 is N or C(T 32 ), Y 33 is N or C(T 33 ), Y 34 is N or C(T 34 ), Y 41 is N or C(T 41 ), Y 42 is N or C(T 42 ), Y 43 is N or C(T 43 ), Y 44 is N or C(T 44 ), T 11 to T 14 each independently the same as defined with respect to T1in Formula 1A, T 21 to T 24 each independently the same as defined with respect to T2in Formula 1A, T 31 to T 34 each independently the same as defined with respect to T3in Formula 1A, T 41 to T 44 each independently the same as defined for T4in Reference Formula 1A, ring Ar7, T 51 to T 54 , T 61 to T 63 , T7and b7are each the same as defined in Formula 1A, and 18. The organometallic compound according to claim 9, wherein the ring Ar7 is phenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, or isoquinolyl.
19. The organometallic compound according to claim 9, wherein the organometallic compound represented by Formula 1 is represented by Formula 1-1 or Formula 1-2: Formula 1-1 Formula 1-2 wherein in Formula 1-1 and Formula 1-2, T 11 to T 14 each independently the same as defined with respect to T1in Formula 1A, T 21 to T 24 each independently the same as defined with respect to T2in Formula 1A, T 31 to T 34 each independently the same as defined with respect to T3in Formula 1A, T 41 to T 44 each independently the same as defined for T4in Reference Formula 1A, ring Ar7, T 51 to T 54 , T 61 to T 63 , T7and b7are each the same as defined in Formula 1A, and M, A, L1to L3, and n1to n3are each the same as defined in Formula 1, X 11 is C(R 11 ) or N, X 12 is C(R 12 ) or N, X 13 is C(R 13 ) or N, X 14 is C(R 14 ) or N, X 21 is C(R 21 ) or N, X 22 is C(R 22 ) or N, X 23 is C(R 23 ) or N, X 31 is C(R 31 ) or N, X 32 is C(R 32 ) or N, X 33 is C(R 33 ) or N, X 34 is C(R 34 ) or N, X 35 is C(R 35 ) or N, X 36 is C(R 36 ) or N, X 41 is C(R 41 ) or N, X 42 is C(R 42 ) or N, X 43 is C(R 43 ) or N, X 44 is C(R 44 ) or N, R 11 to R 14 each independently the same as R1in reference to Formula 1, R 21 to R 23 each independently the same as R2in reference to Formula 1, R 31 to R 36 each independently the same as defined for R3in Reference Formula 1, and R 41 to R 44 each independently the same as defined for R4in Reference Formula 1.
20. The organometallic compound of claim 9, wherein the organometallic compound represented by Formula 1 is one of Compound 1 to Compound 168: ###0009### Compound 1 ###0010### Compound 2 ###0011### Compound 3 ###0012### Compound 4 ###0013### Compound 5 ###0014### Compound 6 ###0015### Compound 7 ###0016### Compound
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Method for dispersing a self-emulsifying crosslinking agent, the resulting crosslinking agent dispersion and its application in an E-coat having a low baking temperature
KR1020240094005A