Organometal compound, light-emitting device including the organometal compound, and electronic device and
By using organometallic compounds that meet specific conditions as interlayer materials in the light emitting device, the problem of high capacitance and charge amount is solved, and a light emitting device with low capacitance and low charge amount is realized, which improves the display quality and efficiency.
Patent Information
- Application Number
- CN202510026871.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-01-08
- Filing Date
- 2025-01-08
- Publication Date
- 2025-07-08
AI Technical Summary
Existing light emitting devices have high demands in terms of capacitance and charge, which affects the display quality and efficiency.
The composition of the emission layer is optimized to reduce capacitance and charge amounts by using an organometallic compound that meets specific conditions A and B as the interlayer material of the emission layer, including a blue phosphorescent dopant or sensitizer.
By using organometallic compounds that meet conditions A and B, the capacitance and charge amount of the light emitting device are significantly reduced, the display quality is improved, the RC delay is reduced, and the luminous efficiency is improved.
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Figure CN120271633A_ABST
Abstract
Description
[0001] Cross - reference to related applications
[0002] This application claims the priority and benefit of Korean Patent Application No. 10 - 2024 - 0003124, filed with the Korean Intellectual Property Office on January 8, 2024, the entire content of which is incorporated herein by reference. Technical field
[0003] Embodiments relate to an organometallic compound, a light - emitting device including the organometallic compound, and an electronic device and electronic apparatus including the light - emitting device. Background art
[0004] A light - emitting device (e.g., an organic light - emitting device) is a self - emitting device having a wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed.
[0005] The light - emitting device may include a first electrode, a hole - transport region, an emission layer, an electron - transport region, and a second electrode, which may be sequentially arranged. Holes injected from the first electrode may move toward the emission layer through the hole - transport region. Electrons injected from the second electrode may move toward the emission layer through the electron - transport region. Charge carriers, such as holes and electrons, may recombine in the emission layer to generate excitons. When the excitons transition from the excited state to the ground state, light may be generated.
[0006] It should be understood that this background - art section is intended to provide useful background for understanding the technology. However, this background - art section may also include ideas, concepts, or knowledge that were not known or understood by those skilled in the art before the effective filing date of the subject matter disclosed herein. Summary of the invention
[0007] Embodiments provide a light - emitting device that emits blue phosphorescence and has a low capacitance and a low charge amount, an electronic device having improved display quality by including the light - emitting device, and an organometallic compound (blue phosphorescent dopant or sensitizer) that satisfies conditions for reducing the capacitance and charge amount of the light - emitting device.
[0008] Additional aspects will be set forth in part in the description that follows and in part will be obvious from the description, or may be learned by practice of the embodiments of the present disclosure.
[0009] According to an embodiment, the light - emitting device may include a first electrode, a second electrode facing the first electrode, and a sandwich structure between the first electrode and the second electrode and including an emission layer, wherein the sandwich structure includes an organometallic compound represented by Formula 1 and satisfying Condition A and Condition B.
[0010] [Formula 1]
[0011]
[0012] [Condition A]
[0013] In Formula 1, the part represented by is the part represented by Formula 1-1 or Formula 1-2.
[0014] [Formula 1-1]
[0015]
[0016] [Formula 1-2]
[0017]
[0018] [Condition B]
[0019] At least one of R2 with a quantity of a2 is each independently deuterium, methyl, ethyl, propyl, methyl substituted with at least one deuterium, ethyl substituted with at least one deuterium, or propyl substituted with at least one deuterium.
[0020] In Formula 1, Formula 1-1, and Formula 1-2,
[0021] M can be platinum (Pt), palladium (Pd), gold (Au), silver (Ag), nickel (Ni), or copper (Cu),
[0022] X1 to X4 can each independently be carbon (C) or nitrogen (N),
[0023] T1 can be a single bond, O, N(Z1), or C(Z1)(Z2),
[0024] Ring CY1 to Ring CY4 and Ring CY 11 to Ring CY 16 can each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0025] Z1, Z2, R1 to R4, and R 1a to R 1f can 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 10aSubstituted C3-C 60 carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 heterocyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0026] Multiple Rs 1a may optionally be bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group, 10a Substituted C1-C 60 heterocyclic group,
[0027] Multiple Rs 1b may optionally be bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group, 10a Substituted C1-C 60 heterocyclic group,
[0028] Multiple Rs 1c may optionally be bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group, 10a Substituted C1-C 60 heterocyclic group,
[0029] Multiple Rs 1d may optionally be bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group, 10a Substituted C1-C 60 heterocyclic group,
[0030] Multiple Rs 1e may optionally be bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group, 10a Substituted C1-C 60 heterocyclic group,
[0031] Multiple Rs 1f may optionally be bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60A carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0032] a1 to a4 and b1 to b6 can each independently be an integer selected from 0 to 20,
[0033] R 10a can be:
[0034] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0035] each unsubstituted or substituted by the following C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0036] each unsubstituted or substituted by the following C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl or C2-C 60 heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl group, -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
[0037] -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 ),
[0038] Q1 to Q3, Q 11 to Q 13 、Q 21 to Q 23 and Q 31 to Q 33 may each independently be:
[0039] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group or nitro group; or
[0040] Each unsubstituted or substituted C1-C 60 Alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl group or C2-C 60 Heteroarylalkyl group: deuterium, -F, cyano group, C1-C 60 Alkyl group, C1-C 60 Alkoxy group, phenyl group, biphenyl group or any combination thereof,
[0041] *Indicates the bonding site of M in Formula 1, and
[0042] *’ indicates the bonding site of the ring CY2 in Formula 1.
[0043] In an embodiment, the light-emitting device may further include: a second compound including at least one π-deficient nitrogen-containing C1-C 60 heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound as a delayed fluorescence compound, or any combination thereof, wherein
[0044] the organometallic compound, the second compound, the third compound, and the fourth compound represented by Formula 1 may be different from each other, and Formula 3 is explained below.
[0045] In an embodiment, the second compound may include a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof; and the fourth compound may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
[0046] In an embodiment, the emission layer may include: an organometallic compound represented by Formula 1; and a second compound, a third compound, a fourth compound, or any combination thereof; and the emission layer may emit blue light.
[0047] According to an embodiment, the electronic device may include a light-emitting device and a thin-film transistor electrically connected to the light-emitting device.
[0048] According to an embodiment, the electronic device may include a light-emitting device, wherein the electronic device may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall including a plurality of displays spliced together, a theater screen, a stadium screen, a light therapy device, or a signboard.
[0049] According to an embodiment, the organometallic compound may be represented by Formula 1 and may satisfy Condition A and Condition B, wherein Formula 1 and Condition A and Condition B are explained herein.
[0050] In an embodiment, in Formula 1, X1 may be a carbon atom of a carbene moiety.
[0051] In an embodiment, in Formula 1, ring CY1 may be a nitrogen-containing C1-C 60 heterocyclic group.
[0052] In an embodiment, rings CY 11 to ring CY 13 in Formula 1-1 may be the same as each other; and rings CY 14 to ring CY 16 in Formula 1-2 may be the same as each other.
[0053] In an embodiment, at least one of Condition 1 to Condition 3, which will be explained below, may be satisfied.
[0054] In an embodiment, in Formula 1-2, the ring formed by CY1-CY 14 -CY 15 -CY 16 surrounding may be a 9-membered ring.
[0055] In an embodiment, in Formula 1, the part represented by may be a part represented by one of Formula 1A to Formula 1C, which will be explained below.
[0056] In an embodiment, in Formula 1A and Formula 1B, the part represented by
[0057] may be a part represented by Formula AS, which will be explained below.
[0058] In an embodiment, in Formula 1C:
[0059] X 13 e may be C(R 13 e), and R 13 e may be a phenyl group substituted with at least one of deuterium and tert-butyl;
[0060] X 14 f may be C(R 14 f), and R 14 f may be a phenyl group substituted with at least one of deuterium and tert-butyl; or
[0061] X 13 e may be C(R 13 e), X 14 f may be C(R 14 f), and R 13 e and R 14 f may each independently be a phenyl group substituted with at least one of deuterium and tert-butyl.
[0062] In an embodiment, in Formula 1, the part represented by may be a part represented by Formula 2-1, which will be explained below.
[0063] In an embodiment, in Formula 1, ring CY3 may be:
[0064] a C2-C8 monocyclic group; or
[0065] a C4-C polycyclic group in which two or three C2-C8 monocyclic groups are fused to each other 20 polycyclic group.
[0066] In an embodiment, in Formula 1, the moiety represented by may be a moiety represented by one of Formulas 3A to 3F, which will be explained below.
[0067] In an embodiment, in Formula 1, the moiety represented by may be a moiety represented by Formula 4-1, which will be explained below.
[0068] In an embodiment, the organometallic compound represented by Formula 1 is one of Compounds BD1 to BD27, which will be explained below.
[0069] It should be understood that the above embodiments are described only in a general and illustrative sense and not for the purpose of limitation, and the present disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS
[0070] The accompanying drawings are included to provide a further understanding of the embodiments, and the accompanying drawings are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the present disclosure and their principles. By describing its embodiments in detail with reference to the accompanying drawings, the above and other aspects and features of the present disclosure will become more apparent, wherein:
[0071] Figure 1 is a graph showing the results of measuring the amount of charge (i.e., the corresponding capacitance) of a light-emitting device including an organometallic compound, according to the structure of the organometallic compound;
[0072] Figure 2 is a schematic cross-sectional view of a light-emitting device according to an embodiment;
[0073] Figure 3 is a schematic cross-sectional view of an electronic device according to an embodiment;
[0074] Figure 4 is a schematic cross-sectional view of an electronic device according to another embodiment;
[0075] Figure 5 is a schematic perspective view of an electronic apparatus including a light-emitting device according to an embodiment;
[0076] Figure 6Schematic perspective view of the exterior of a vehicle as an electronic device including a light-emitting device according to an embodiment; and
[0077] Figures 7A to 7C Each is a schematic diagram of the interior of a vehicle according to an embodiment Figure 6 in Detailed Description
[0078] The present disclosure will now be described more fully hereinafter with reference to the accompanying drawings in which embodiments are shown. However, the present disclosure may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the disclosure to those skilled in the art.
[0079] In the drawings, for ease of description and for clarity, the dimensions (e.g., thickness), ratios, and dimensions of elements may be exaggerated. The same reference numerals and / or the same reference characters refer to the same elements throughout.
[0080] In the description, it will be understood that when an element (or region, layer, component, etc.) is referred to as being "on" another element (or region, layer, component, etc.), "connected to" or "coupled to" another element (or region, layer, component, etc.), it may be directly on the other element (or region, layer, component, etc.), directly connected to or directly coupled to the other element (or region, layer, component, etc.), or there may be one or more intervening elements (or regions, layers, components, etc.) therebetween. In a similar sense, when an element (or region, layer, component, etc.) is described as "covering" another element (or region, layer, component, etc.), it may directly cover the other element (or region, layer, component, etc.), or there may be one or more intervening elements (or regions, layers, components, etc.) therebetween.
[0081] In the description, when an element is "directly on" another element, "directly connected to" or "directly coupled to" another element, there is no intervening element. For example, "directly on" may mean that two layers or two elements are provided without another element (such as an adhesive element) therebetween.
[0082] As used herein, expressions used in the singular form, such as "a", "an", and "the", are also intended to include the plural form unless the context clearly indicates otherwise.
[0083] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. For example, "A and / or B" may be understood to mean "A, B, or A and B". The terms "and" and "or" may be used in a conjunctive sense or a disjunctive sense and may be understood to be equivalent to "and / or".
[0084] In the specification and claims, for purposes of their meaning and interpretation, the term "at least one of..." is intended to include the meaning of "at least one selected from the group consisting of...". For example, "at least one of A, B, and C" can be understood to mean only A, only B, only C, or any combination of two or more of A, B, and C, such as ABC, ACC, BC, or CC. When following a list of elements, the term "at least one of..." modifies the entire list of elements and not a single element of the list.
[0085] It will be understood that although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. Thus, without departing from the teachings of the present disclosure, a first element may be referred to as a second element. Similarly, without departing from the scope of the present disclosure, a second element may be referred to as a first element.
[0086] For ease of description, spatial relative terms such as "below", "beneath", "under", "above", or "on" etc. may be used herein to describe the relationship between one element or component and another element or component as illustrated in the figures. It will be understood that, in addition to the orientation depicted in the figures, spatial relative terms are also intended to encompass different orientations of the device in use or operation. For example, in the case of flipping the device illustrated in the figures, a device located "below" or "beneath" another device may be positioned "above" the other device. Accordingly, the illustrative term "below" can include both lower and upper positions. The device may also be oriented in other directions and, thus, the spatial relative terms may be differently interpreted depending on the orientation.
[0087] As used herein, the term "about" or "approximately" includes the recited value and means within an acceptable deviation range determined by a person of ordinary skill in the art in view of the measurement being discussed and the errors associated with the measurement of the recited quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations of the recited value, or within ±20%, ±10%, or ±5% of the recited value.
[0088] It should be understood that the terms "comprises", "comprising", "includes", "including", "have", "having", "contains", and "containing", etc. are intended to indicate the presence of the recited features, integers, steps, operations, elements, components, or any combination thereof in the present disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or any combination thereof.
[0089] Unless otherwise defined or implied herein, all terms used (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. 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 should not be interpreted in an idealized or overly formal sense unless clearly defined in the specification.
[0090] According to an embodiment, the light-emitting device may include:
[0091] a first electrode;
[0092] a second electrode facing the first electrode; and
[0093] a sandwich layer between the first electrode and the second electrode and including an emission layer, wherein
[0094] the sandwich layer includes an organometallic compound represented by Formula 1 and satisfying Condition A and Condition B:
[0095] [Formula 1]
[0096]
[0097] [Condition A]
[0098] In Formula 1, the moiety represented by may be a moiety represented by Formula 1-1 or Formula 1-2;
[0099] [Formula 1-1]
[0100]
[0101] [Formula 1-2]
[0102]
[0103] [Condition B]
[0104] At least one of R2 with a quantity of a2 may each independently be deuterium, methyl, ethyl, propyl, methyl substituted with at least one deuterium, ethyl substituted with at least one deuterium, or propyl substituted with at least one deuterium.
[0105] In Formula 1, Formula 1-1, and Formula 1-2,
[0106] M may be platinum (Pt), palladium (Pd), gold (Au), silver (Ag), nickel (Ni), or copper (Cu),
[0107] X1 to X4 may each independently be carbon (C) or nitrogen (N),
[0108] T1 can be a single bond, O, N(Z1) or C(Z1)(Z2),
[0109] Ring CY1 to ring CY4 and ring CY 11 to ring CY 16 can each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0110] Z1, Z2, R1 to R4 and R 1a to R 1f can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, an unsubstituted or at least one R 10a substituted C1-C 60 alkyl, an unsubstituted or at least one R 10a substituted C2-C 60 alkenyl, an unsubstituted or at least one R 10a substituted C2-C 60 alkynyl, an unsubstituted or at least one R 10a substituted C1-C 60 alkoxy, an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group, an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0111] Multiple Rs 1a can optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0112] Multiple Rs 1b can optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0113] Multiple Rs 1c can optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C60 a carbocyclic group or an unsubstituted or at least one R- 10a substituted C1-C 60 heterocyclic group,
[0114] multiple Rs 1d may optionally be bonded to each other to form an unsubstituted or at least one R- 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R- 10a substituted C1-C 60 heterocyclic group,
[0115] multiple Rs 1e may optionally be bonded to each other to form an unsubstituted or at least one R- 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R- 10a substituted C1-C 60 heterocyclic group,
[0116] multiple Rs 1f may optionally be bonded to each other to form an unsubstituted or at least one R- 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R- 10a substituted C1-C 60 heterocyclic group,
[0117] a1 to a4 and b1 to b6 may each independently be an integer selected from 0 to 20,
[0118] R 10a may be:
[0119] deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;
[0120] each unsubstituted or substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q11 )(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;
[0121] Each unsubstituted or substituted C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group or C2-C 60 heteroaralkyl group: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, -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
[0122] -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),
[0123] Q1 to Q3, Q 11 to Q 13 and Q 21 to Q 23 and Q 31 to Q 33 may each independently be:
[0124] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; or
[0125] each unsubstituted or substituted by the following C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl or C2-C 60 heteroaralkyl: deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl or any combination thereof,
[0126] * indicates the bonding site to M in Formula 1, and
[0127] *’ indicates the bonding site to ring CY2 in Formula 1.
[0128] Formula 1, Formula 1-1 and Formula 1-2 are the same as those described in the specification, respectively.
[0129] Since the light-emitting device includes an organometallic compound represented by Formula 1 and satisfying Condition A and Condition B, the light-emitting device may have a low capacitance and a low charge amount.
[0130] In an embodiment, the emission layer may include an organometallic compound represented by Formula 1.
[0131] In an embodiment, the light-emitting device may further include: a second compound including at least one π-deficient nitrogen-containing C1-C 60 heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence (e.g., a delayed fluorescence compound) or any combination thereof, wherein the organometallic compound represented by Formula 1, the second compound, the third compound and the fourth compound may be different from each other:
[0132] [Formula 3]
[0133]
[0134] In Formula 3,
[0135] Ring CY 71 and Ring CY 72 may each independently be a π - electron - rich C3 - C 60 cyclic group or a pyridyl group,
[0136] X 71 may be: a single bond; or a linking group including O, S, N, B, C, Si, or any combination thereof, and
[0137] * indicates the bonding site to any atom included in the remainder of the third compound other than Formula 3.
[0138] In an embodiment, the organometallic compound represented by Formula 1 and the second to fourth compounds may each include at least one deuterium atom.
[0139] In an embodiment, the second compound and the third compound may each include at least one silicon atom.
[0140] In an embodiment, the interlayer (e.g., the emissive layer) may include: the organometallic compound represented by Formula 1; the organometallic compound represented by Formula 1 and the second compound; the organometallic compound represented by Formula 1 and the third compound; the organometallic compound represented by Formula 1 and the fourth compound; the organometallic compound represented by Formula 1, the second compound, and the third compound; the organometallic compound represented by Formula 1, the second compound, and the fourth compound; the organometallic compound represented by Formula 1, the third compound, and the fourth compound; or the organometallic compound represented by Formula 1 and the second to fourth compounds.
[0141] In an embodiment, the second compound and the third compound may form an exciplex.
[0142] In an embodiment, the fourth compound may be used to improve the color purity, luminous efficiency, and / or lifetime characteristics of the light - emitting device.
[0143] In an embodiment, the highest occupied molecular orbital (HOMO) energy level of the organometallic compound represented by Formula 1 may be in the range of about - 5.35 eV to about - 5.15 eV. For example, the HOMO energy level of the organometallic compound represented by Formula 1 may be in the range of about - 5.30 eV to about - 5.20 eV.
[0144] In an embodiment, the lowest unoccupied molecular orbital (LUMO) energy level of the organometallic compound represented by Formula 1 may be in the range of about - 2.20 eV to about - 1.80 eV. For example, the LUMO energy level of the organometallic compound represented by Formula 1 may be in the range of about - 2.15 eV to about - 1.90 eV.
[0145] The HOMO and LUMO energy levels can be evaluated by cyclic voltammetry analysis of the organometallic compound represented by Formula 1, respectively.
[0146] In an embodiment, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of a film including the organometallic compound represented by Formula 1 can be in the range of about 430 nm to about 475 nm. For example, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of a film including the organometallic compound represented by Formula 1 can be in the range of about 440 nm to about 475 nm. For example, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of a film including the organometallic compound represented by Formula 1 can be in the range of about 450 nm to about 475 nm. For example, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of a film including the organometallic compound represented by Formula 1 can be in the range of about 430 nm to about 470 nm. For example, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of a film including the organometallic compound represented by Formula 1 can be in the range of about 440 nm to about 470 nm. For example, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of a film including the organometallic compound represented by Formula 1 can be in the range of about 450 nm to about 470 nm. For example, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of a film including the organometallic compound represented by Formula 1 can be in the range of about 430 nm to about 465 nm. For example, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of a film including the organometallic compound represented by Formula 1 can be in the range of about 440 nm to about 465 nm. For example, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of a film including the organometallic compound represented by Formula 1 can be in the range of about 450 nm to about 465 nm. For example, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of a film including the organometallic compound represented by Formula 1 can be in the range of about 430 nm to about 460 nm. For example, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of a film including the organometallic compound represented by Formula 1 can be in the range of about 440 nm to about 460 nm. For example, the maximum emission wavelength (or emission peak wavelength) of the emission spectrum of a film including the organometallic compound represented by Formula 1 can be in the range of about 450 nm to about 460 nm.
[0147] In an embodiment, the full width at half maximum (FWHM) of the emission spectrum of a film including the organometallic compound represented by Formula 1 may be less than or equal to about 40 nm. For example, the FWHM of the emission spectrum of a film including the organometallic compound represented by Formula 1 may be in the range of about 5 nm to about 40 nm. For example, the FWHM of the emission spectrum of a film including the organometallic compound represented by Formula 1 may be in the range of about 10 nm to about 40 nm. For example, the FWHM of the emission spectrum of a film including the organometallic compound represented by Formula 1 may be in the range of about 15 nm to about 40 nm. For example, the FWHM of the emission spectrum of a film including the organometallic compound represented by Formula 1 may be in the range of about 20 nm to about 40 nm. For example, the FWHM of the emission spectrum of a film including the organometallic compound represented by Formula 1 may be in the range of about 5 nm to about 37 nm. For example, the FWHM of the emission spectrum of a film including the organometallic compound represented by Formula 1 may be in the range of about 10 nm to about 37 nm. For example, the FWHM of the emission spectrum of a film including the organometallic compound represented by Formula 1 may be in the range of about 15 nm to about 37 nm. For example, the FWHM of the emission spectrum of a film including the organometallic compound represented by Formula 1 may be in the range of about 20 nm to about 37 nm.
[0148] The maximum emission wavelength and the FWHM of the emission spectrum of the organometallic compound represented by Formula 1 may be evaluated for a film including the organometallic compound represented by Formula 1.
[0149] In an embodiment, the emission layer may include: an organometallic compound represented by Formula 1; and a second compound, a third compound, a fourth compound, or any combination thereof, wherein the emission layer may emit blue light.
[0150] In an embodiment, the maximum emission wavelength of the blue light may be in the range of about 390 nm to about 500 nm. For example, the maximum emission wavelength of the blue light may be in the range of about 410 nm to about 490 nm. For example, the maximum emission wavelength of the blue light may be in the range of about 430 nm to about 480 nm. For example, the maximum emission wavelength of the blue light may be in the range of about 440 nm to about 475 nm. For example, the maximum emission wavelength of the blue light may be in the range of about 455 nm to about 470 nm.
[0151] In an embodiment, the full width at half maximum (FWHM) of the emission spectrum of the blue light may be less than or equal to about 40 nm. For example, the FWHM of the emission spectrum of the blue light may be in the range of about 5 nm to about 40 nm. For example, the FWHM of the emission spectrum of the blue light may be in the range of about 10 nm to about 40 nm. For example, the FWHM of the emission spectrum of the blue light may be in the range of about 15 nm to about 40 nm. For example, the FWHM of the emission spectrum of the blue light may be in the range of about 20 nm to about 40 nm. For example, the FWHM of the emission spectrum of the blue light may be in the range of about 5 nm to about 37 nm. For example, the FWHM of the emission spectrum of the blue light may be in the range of about 10 nm to about 37 nm. For example, the FWHM of the emission spectrum of the blue light may be in the range of about 15 nm to about 37 nm. For example, the FWHM of the emission spectrum of the blue light may be in the range of about 20 nm to about 37 nm.
[0152] In an embodiment, the blue light may be deep blue light.
[0153] In an embodiment, the CIEx coordinate of the blue light (e.g., the bottom emission CIEx coordinate) may be in the range of about 0.125 to about 0.140. For example, the CIEx coordinate of the blue light (e.g., the bottom emission CIEx coordinate) may be in the range of about 0.130 to about 0.140.
[0154] In an embodiment, the CIEy coordinate of the blue light (e.g., the bottom emission CIEy coordinate) may be in the range of about 0.120 to about 0.210.
[0155] In an embodiment, the second compound may include a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof.
[0156] In an embodiment, the second compound may include a compound represented by Formula 2:
[0157] [Formula 2]
[0158]
[0159] In Formula 2,
[0160] L 51 to L 53 may each independently be a single bond, an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0161] b51 to b53 may each independently be an integer selected from 1 to 5,
[0162] X54 can be N or C(R 54 ), X 55 can be N or C(R 55 ), X 56 can be N or C(R 56 ), and X 54 to X 56 in at least one of which can each be N, and
[0163] R 51 to R 56 can each independently be the same as those described with reference to R 10a in the specification.
[0164] In an embodiment, the third compound can include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
[0165] [Formula 3-1]
[0166]
[0167] [Formula 3-2]
[0168]
[0169] [Formula 3-3]
[0170]
[0171] [Formula 3-4]
[0172]
[0173] [Formula 3-5]
[0174]
[0175] In Formulas 3-1 to 3-5,
[0176] ring CY 71 to ring CY 74 can each independently be an electron-rich C3-C 60 cyclic group or pyridyl,
[0177] X 82 can be a single bond, O, S, N[(L 82 ) b82 -R 82 , C(R 82a )(R 82b ), or Si(R 82a )(R 82b ),
[0178] X 83 can be a single bond, O, S, N[(L 83 ) b83 -R 83 , C(R 83a )(R 83b ) or Si(R 83a )(R 83b ),
[0179] X 84 can be O, S, N[(L 84 ) b84 -R 84 , C(R 84a )(R 84b ) or Si(R 84a )(R 84b ),
[0180] X 85 can be C or Si,
[0181] L 81 to L 85 can each independently be a single bond, *-C(Q4)(Q5)-*’, *-Si(Q4)(Q5)-*’, an unsubstituted or at least one R 10a substituted π - electron - rich C3 - C 60 cyclic group or an unsubstituted or at least one R 10a substituted pyridyl group, where Q4 and Q5 can each independently be the same as described for Q1,
[0182] b81 to b85 can each independently be an integer selected from 1 to 5,
[0183] R 71 to R 74 , R 81 to R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b can each independently be the same as described for R1,
[0184] a71 to a74 can each independently be an integer selected from 0 to 20, and
[0185] R 10a can be as described in the specification.
[0186] In an embodiment, the third compound may not be CBP or mCBP:
[0187]
[0188] In an embodiment, the difference between the triplet energy level (eV) and the singlet energy level (eV) of the fourth compound can be in the range of about 0 eV to about 0.5 eV. For example, the difference between the triplet energy level (eV) and the singlet energy level (eV) of the fourth compound can be in the range of about 0 eV to about 0.3 eV.
[0189] In an embodiment, the fourth compound can be a compound including at least one cyclic group, and the cyclic group includes boron (B) and nitrogen (N) as ring-forming atoms.
[0190] For example, the fourth compound can be a compound containing a C8-C 60 polycyclic group, and the C8-C 60 polycyclic group includes at least two cyclic groups fused to each other and sharing boron (B).
[0191] In an embodiment, the fourth compound can include a polycyclic ring in which at least one third ring can be fused to at least one fourth ring,
[0192] the third ring can be cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, adamantyl, norbornenyl, norbornyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl, and
[0193] the fourth ring can be 1,2-azaborolyl, 1,3-azaborolyl, 1,4-azaborolyl, 1,2-dihydro-1,2-azaborolyl, 1,4-oxaborolyl, 1,4-thiaboryl or 1,4-dihydroboryl.
[0194] In an embodiment, the fourth compound can include a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
[0195] [Formula 502]
[0196]
[0197] [Formula 503]
[0198]
[0199] In Formula 502 and Formula 503,
[0200] Ring A 501 to Ring A 504 can each independently be a C3-C 60 carbocyclic group or a C1-C60 Heterocyclic group
[0201] Y 505 may be O, S, N(R 505 ), B(R 505 ), C(R 505a )(R 505b ), or Si(R 505a )(R 505b ),
[0202] Y 506 may be O, S, N(R 506 ), B(R 506 ), C(R 506a )(R 506b ), or Si(R 506a )(R 506b ),
[0203] Y 507 may be O, S, N(R 507 ), B(R 507 ), C(R 507a )(R 507b ), or Si(R 507a )(R 507b ),
[0204] Y 508 may be O, S, N(R 508 ), B(R 508 ), C(R 508a )(R 508b ), or Si(R 508a )(R 508b ),
[0205] Y 51 and Y 52 may each independently be B, P(=O), or S(=O),
[0206] R 500a , R 500b , R 501 to R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b may each independently be the same as described for R1, and
[0207] a501 to a504 may each independently be an integer selected from 0 to 20.
[0208] In an embodiment, the light-emitting device may satisfy at least one of Conditions 11 to 14:
[0209] [Condition 11]
[0210] The LUMO energy level (eV) of the third compound > the LUMO energy level (eV) of the organometallic compound represented by Formula 1;
[0211] [Condition 12]
[0212] The LUMO energy level (eV) of the organometallic compound represented by Formula 1 > the LUMO energy level (eV) of the second compound;
[0213] [Condition 13]
[0214] The HOMO energy level (eV) of the organometallic compound represented by Formula 1 > the HOMO energy level (eV) of the third compound; and
[0215] [Condition 14]
[0216] The HOMO energy level (eV) of the third compound > the HOMO energy level (eV) of the second compound.
[0217] The HOMO energy level and the LUMO energy level of each of the organometallic compound represented by Formula 1, the second compound, and the third compound may each be negative values and may be measured according to methods in the relevant art.
[0218] In an embodiment, the absolute value of the difference between the LUMO energy level of the organometallic compound represented by Formula 1 and the LUMO energy level of the second compound may be in the range of about 0.1 eV to about 1.0 eV, and / or the absolute value of the difference between the LUMO energy level of the organometallic compound represented by Formula 1 and the LUMO energy level of the third compound may be about 0.1 eV to about 1.0 eV.
[0219] In an embodiment, the absolute value of the difference between the HOMO energy level of the organometallic compound represented by Formula 1 and the HOMO energy level of the second compound may be less than or equal to about 1.25 eV (e.g., about 0.2 eV to about 1.25 eV), and / or the absolute value of the difference between the HOMO energy level of the organometallic compound represented by Formula 1 and the HOMO energy level of the third compound may be less than or equal to about 1.25 eV (e.g., about 0.2 eV to about 1.25 eV).
[0220] When the relationship between the LUMO energy level and the HOMO energy level satisfies the conditions as described above, balance between holes and electrons injected into the emission layer can be achieved.
[0221] The light-emitting device may have the structure of the first embodiment or the second embodiment.
[0222] [First Embodiment]
[0223] According to the first embodiment, the emission layer may include an organometallic compound represented by Formula 1 and a host, where the organometallic compound represented by Formula 1 and the host may be different from each other, and the emission layer may emit phosphorescence or fluorescence emitted from the organometallic compound represented by Formula 1. The phosphorescence or fluorescence emitted from the organometallic compound represented by Formula 1 may be blue light.
[0224] For example, according to the first embodiment, the organometallic compound represented by Formula 1 may be a dopant (or emitter). In an embodiment, the organometallic compound represented by Formula 1 may be a phosphorescent dopant (or phosphorescent emitter).
[0225] The emission layer may further include a co-dopant different from each of the organometallic compound represented by Formula 1 and the host. The co-dopant may effectively transfer energy to the organometallic compound represented by Formula 1 that can act as a dopant, and thus improve the luminescence efficiency of the organometallic compound represented by Formula 1.
[0226] In an embodiment, the co-dopant may be a compound that emits delayed fluorescence. The co-dopant may be a compound including at least one cyclic group that includes boron (B) and nitrogen (N) as ring-forming atoms. The co-dopant in the first embodiment may include, for example, a fourth compound represented by Formula 502 or Formula 503.
[0227] [Second Embodiment]
[0228] According to the second embodiment, the emission layer may include an organometallic compound represented by Formula 1, a host, and a dopant (or emitter), where the organometallic compound represented by Formula 1, the host, and the dopant may be different from each other, and the emission layer may emit phosphorescence or fluorescence (e.g., delayed fluorescence) emitted from the dopant.
[0229] In an embodiment, the organometallic compound represented by Formula 1 in the second embodiment may not be a dopant, but may be used as a co-dopant that transfers energy to the dopant (or emitter).
[0230] In another embodiment, the organometallic compound represented by Formula 1 in the second embodiment may be used as a dopant and may also be used as a co-dopant that transfers energy to the dopant.
[0231] The phosphorescence or fluorescence emitted from the dopant in the second embodiment may be blue light, such as blue phosphorescence or blue fluorescence (e.g., blue delayed fluorescence).
[0232] The dopant in the second embodiment may be any phosphorescent dopant material (e.g., an organometallic compound represented by Formula 1, an organometallic compound represented by Formula 401, or any combination thereof) or any fluorescent dopant material (e.g., a compound represented by Formula 501, a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof).
[0233] In the first and second embodiments, the blue light may have a maximum emission wavelength in the range of about 390 nm to about 500 nm. For example, the blue light in the first and second embodiments may be blue light having a maximum emission wavelength in the range of about 410 nm to about 490 nm. For example, the blue light in the first and second embodiments may be blue light having a maximum emission wavelength in the range of about 430 nm to about 480 nm. For example, the blue light in the first and second embodiments may be blue light having a maximum emission wavelength in the range of about 440 nm to about 475 nm. For example, the blue light in the first and second embodiments may be blue light having a maximum emission wavelength in the range of about 455 nm to about 470 nm.
[0234] The host in the first and second embodiments may be any host material (e.g., a compound represented by Formula 301, a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof).
[0235] The host in the first and second embodiments may be a second compound, a third compound, or any combination thereof.
[0236] In an embodiment, the light-emitting device may further include a capping layer outside the first electrode and / or outside the second electrode.
[0237] For example, the light-emitting device may further include at least one of a first capping layer outside the first electrode and a second capping layer outside the second electrode.
[0238] At least one of the first capping layer and the second capping layer may include an organometallic compound represented by Formula 1. According to an embodiment, the light-emitting device may further include a first capping layer outside the first electrode, and the first capping layer may include an organometallic compound represented by Formula 1. According to another embodiment, the light-emitting device may further include a second capping layer outside the second electrode, and the second capping layer may include an organometallic compound represented by Formula 1. According to another embodiment, the light-emitting device may further include a first capping layer outside the first electrode and a second capping layer outside the second electrode, and at least one of the first capping layer and the second capping layer may include an organometallic compound represented by Formula 1. The first capping layer and / or the second capping layer may each be the same as those described herein.
[0239] In an embodiment, the light-emitting device may include:
[0240] a first capping layer outside the first electrode and including an organometallic compound represented by Formula 1;
[0241] a second capping layer outside the second electrode and including an organometallic compound represented by Formula 1; or
[0242] both the first capping layer and the second capping layer.
[0243] As used herein, the expression “(the interlayer and / or the capping layer) includes an organometallic compound represented by Formula 1” may mean that (the interlayer and / or the capping layer) may include one kind of organometallic compound represented by Formula 1 or two or more different kinds of organometallic compounds each represented by Formula 1.
[0244] In an embodiment, the interlayer and / or the capping layer may include only Compound BD1 as the organometallic compound represented by Formula 1. Compound BD1 may be included in the emission layer of the light-emitting device.
[0245] In another embodiment, the interlayer may include Compound BD1 and Compound BD2 as the organometallic compounds represented by Formula 1. Compound BD1 and Compound BD2 may be included in the same layer (e.g., both Compound BD1 and Compound BD2 may be included in the emission layer), or may be included in different layers (e.g., Compound BD1 may be included in the emission layer and Compound BD2 may be included in the electron transport region).
[0246] As used herein, the term “interlayer” refers to a single layer and / or multiple layers between the first electrode and the second electrode of the light-emitting device.
[0247] According to an embodiment, the electronic device may include: a light-emitting device and a thin-film transistor electrically connected to the light-emitting device. For example, the thin-film transistor may include a source electrode and a drain electrode, and the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. The electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. Further details regarding the electronic device may be the same as those described herein.
[0248] According to an embodiment, the electronic device may include a light-emitting device and may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall including a plurality of displays spliced together, a theater screen, a stadium screen, a light therapy device, or a signboard.
[0249] According to an embodiment, the organometallic compound may be represented by Formula 1 and may satisfy both Condition A and Condition B. Formula 1 may be the same as that described herein.
[0250] By referring to the synthesis examples and / or examples provided below, those of ordinary skill in the art may recognize the synthesis method of the organometallic compound represented by Formula 1.
[0251] Description of the formula
[0252] According to an embodiment, the organometallic compound may be represented by Formula 1 and may satisfy Condition A and Condition B:
[0253] [Formula 1]
[0254]
[0255] [Condition A]
[0256] In Formula 1, the moiety represented by
[0257]
[0258] may be a moiety represented by Formula 1-1 or Formula 1-2;
[0259] [Formula 1-1]
[0260]
[0261] [Formula 1-2]
[0262]
[0263] [Condition B]
[0264] At least one of the R2s in the amount of a2 may each independently be deuterium, methyl, ethyl, propyl, methyl substituted with at least one deuterium, ethyl substituted with at least one deuterium, or propyl substituted with at least one deuterium.
[0265] In Formula 1, Formula 1-1, and Formula 1-2,
[0266] M can be platinum (Pt), palladium (Pd), gold (Au), silver (Ag), nickel (Ni), or copper (Cu),
[0267] X1 to X4 can each independently be carbon (C) or nitrogen (N),
[0268] T1 can be a single bond, O, N(Z1), or C(Z1)(Z2),
[0269] Ring CY1 to Ring CY4 and Ring CY 11 to Ring CY 16 can each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0270] Z1, Z2, R1 to R4, and R 1a to R 1f can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, an unsubstituted or at least one R 10a substituted C1-C 60 alkyl, an unsubstituted or at least one R 10a substituted C2-C 60 alkenyl, an unsubstituted or at least one R 10a substituted C2-C 60 alkynyl, an unsubstituted or at least one R 10a substituted C1-C 60 alkoxy, an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group, an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2),
[0271] Multiple Rs 1a can optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0272] Multiple Rs 1b can optionally be bonded to each other to form an unsubstituted or at least one R 10aSubstituted C3-C 60 carbocyclic group or unsubstituted or substituted by at least one R 10a Substituted C1-C 60 heterocyclic group,
[0273] multiple Rs 1c optionally bond to each other to form an unsubstituted or substituted by at least one R 10a Substituted C3-C 60 carbocyclic group or unsubstituted or substituted by at least one R 10a Substituted C1-C 60 heterocyclic group,
[0274] multiple Rs 1d optionally bond to each other to form an unsubstituted or substituted by at least one R 10a Substituted C3-C 60 carbocyclic group or unsubstituted or substituted by at least one R 10a Substituted C1-C 60 heterocyclic group,
[0275] multiple Rs 1e optionally bond to each other to form an unsubstituted or substituted by at least one R 10a Substituted C3-C 60 carbocyclic group or unsubstituted or substituted by at least one R 10a Substituted C1-C 60 heterocyclic group,
[0276] multiple Rs 1f optionally bond to each other to form an unsubstituted or substituted by at least one R 10a Substituted C3-C 60 carbocyclic group or unsubstituted or substituted by at least one R 10a Substituted C1-C 60 heterocyclic group,
[0277] a1 to a4 and b1 to b6 can each independently be an integer selected from 0 to 20,
[0278] R 10a can be:
[0279] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0280] each unsubstituted or substituted by the following C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, -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;
[0281] each unsubstituted or substituted C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group or C2-C 60 heteroaralkyl group: deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, -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
[0282] -Si(Q 31 )(Q 32 )(Q33 )、 -N(Q 31 )(Q 32 )、 -B(Q 31 )(Q 32 )、 -C(=O)(Q 31 )、 -S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ),
[0283] Q1 to Q3, Q 11 to Q 13 、Q 21 to Q 23 and Q 31 to Q 33 may each independently be:
[0284] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; or
[0285] each unsubstituted or substituted by the following C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl or C2-C 60 heteroaralkyl: deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl or any combination thereof,
[0286] * indicates the bonding site to M in formula 1, and
[0287] *' indicates the bonding site to ring CY2 in formula 1.
[0288] In an embodiment, in formula 1, at least one of the bond between X1 and M, the bond between X2 and M, the bond between X3 and M, and the bond between X4 and M may each independently be a coordination bond.
[0289] In an embodiment, in formula 1, X1 may be the carbon atom of a carbene moiety.
[0290] In an embodiment, in formula 1, at least one of X1 to X4 may each be N. For example, X4 may be N.
[0291] In an embodiment, in formula 1, T1 may be a single bond, O, N(Z1) or C(Z1)(Z2), where Z1 and Z2 may be:
[0292] Hydrogen or deuterium; or
[0293] A methyl, ethyl, propyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, or triazinyl group, each unsubstituted or substituted with at least one deuterium atom.
[0294] In an embodiment, Z1 and Z2 may not be bonded to each other.
[0295] For example, in Formula 1, T1 may be O.
[0296] In an embodiment, Ring CY1 to Ring CY4 and Ring CY 11 to Ring CY 16 may each independently be:
[0297] A C2-C8 monocyclic group; or
[0298] A C4-C polycyclic group in which two or three C2-C8 monocyclic groups are fused to each other 20 polycyclic group.
[0299] As used above, the term "C2-C8 monocyclic group" may refer to a non-fused ring group and may be, for example, cyclopentadienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, cyclohexadienyl, phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, cycloheptadienyl, or cyclooctadienyl.
[0300] In an embodiment, Ring CY1 may be a nitrogen-containing C1-C 60 heterocyclic group. For example, Ring CY1 may include a nitrogen-containing 5-membered ring. As another example, Ring CY1 may be a fused ring including a 5-membered ring and a 6-membered ring. In an embodiment, Ring CY1 may be a 5-membered ring containing X1, a 5-membered ring containing X1 fused to at least one 6-membered ring, or a 6-membered ring containing X1.
[0301] In an embodiment, Ring CY1 in Formula 1 may be a 5-membered ring containing X1 or a 5-membered ring containing X1 fused to at least one 6-membered ring, where
[0302] The 5-membered ring containing X1 may be pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, or thiadiazolyl, and
[0303] The 6-membered ring containing X1 or the 6-membered ring optionally fused to the 5-membered ring containing X1 may be phenyl, pyridyl, or pyrimidinyl.
[0304] For example, Ring CY1 may be imidazolyl, triazolyl, benzimidazolyl, naphthimidazolyl, or imidazopyridyl.
[0305] In an embodiment, in Formula 1-1, Ring CY11 to ring CY 13 may be the same as each other.
[0306] In an embodiment, in Formula 1-2, ring CY 14 to ring CY 16 may be the same as each other.
[0307] In an embodiment, ring CY 11 to ring CY 16 may each include a phenyl group. For example, ring CY 11 to ring CY 16 may each be a phenyl group or a fused ring group (wherein cyclopentadienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, cyclohexadienyl, phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, cycloheptadienyl or cyclooctadienyl may be fused with the phenyl group).
[0308] In an embodiment, ring CY 11 to ring CY 16 may each be a phenyl group,
[0309] A plurality of R1a may optionally be bonded to each other to form a cyclopentadienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, cyclohexadienyl, phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, cycloheptadienyl or cyclooctadienyl which is unsubstituted or substituted by at least one R 10 a, and
[0310] A plurality of R1c may optionally be bonded to each other to form a cyclopentadienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, cyclohexadienyl, phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, cycloheptadienyl or cyclooctadienyl which is unsubstituted or substituted by at least one R 10 a.
[0311] In an embodiment, in Formula 1-2, the ring formed by CY1-CY 14 -CY 15 -CY 16 surrounded may be a 9-membered ring. The 9-membered ring formed by CY1-CY 14 -CY 15 -CY 16 surrounded may be a C9 carbocyclic group.
[0312] In an embodiment, in Formula 1, the moiety represented by may be a moiety represented by one of Formula 1A to Formula 1C:
[0313] [Formula 1A]
[0314]
[0315] [Formula 1B]
[0316]
[0317] [Formula 1C]
[0318]
[0319] In Formula 1A, Formula 1B, and Formula 1C,
[0320] X 11 can be N or C(R 11 ), X 12 can be N or C(R 12 ), X 13 can be N or C(R 13 ), X 14 can be N or C(R 14 ), X 15 can be N or C(R 15 ), X 16 can be N or C(R 16 ), X 17 can be N or C(R 17 ), X 18 can be N or C(R 18 ), X 19 can be N or C(R 19 ), X 11d can be N or C(R 11d ), X 12d can be N or C(R 12d ), X 13d can be N or C(R 13d ), X 14d can be N or C(R 14d ), X 11e can be N or C(R 11e ), X 12e can be N or C(R 12e ), X 13e can be N or C(R 13e ), X 14e can be N or C(R 14e ), X 11f can be N or C(R 11f ), X 12f can be N or C(R 12f ), X 13f can be N or C(R 13f ), and X 14fIt can be N or C(R 14f ),
[0321] R 11 to R 16 can each independently be the same as described for R1 in Formula 1,
[0322] R 17 to R 19 can each independently be the same as described for R 1b in Formula 1-1,
[0323] R 11d to R 14d can each independently be the same as described for R 1d in Formula 1-2,
[0324] R 11e to R 14e can each independently be the same as described for R 1e in Formula 1-2,
[0325] R 11f to R 14f can each independently be the same as described for R 1f in Formula 1-2, and
[0326] b1 and b3 are each independently an integer selected from 0 to 20.
[0327] In an embodiment, in Formula 1A and Formula 1B,
[0328] X 18 can be C(R 18 ), and
[0329] R 18 can each be an unsubstituted or substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl or any combination thereof.
[0330] For example, R 18 can be tert-butyl.
[0331] In an embodiment, the organometallic compound represented by Formula 1 may satisfy at least one of Conditions 1 to 3:
[0332] [Condition 1]
[0333] In Formula 1-1, a plurality of Rs 1a may be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group;
[0334] [Condition 2]
[0335] In Formula 1-1, at least one R 1b may be tert-butyl; and
[0336] [Condition 3]
[0337] In Formula 1-1, a plurality of Rs 1c may be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group.
[0338] In an embodiment, the organometallic compound represented by Formula 1 may satisfy at least one of Conditions 1A to 3A:
[0339] [Condition 1A]
[0340] In Formula 1-1, a plurality of Rs 1a may be bonded to each other to form a cyclopentadienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, cyclohexadienyl, phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, cycloheptadienyl or cyclooctadienyl which is each unsubstituted or substituted by at least one R 10a ;
[0341] [Condition 2A]
[0342] In Formulas 1A and 1B, X 18 may be C(R 18 ), and R 18 may be tert-butyl; and
[0343] [Condition 3A]
[0344] In Formula 1-1, a plurality of Rs 1ccan be bonded to each other to form an unsubstituted or at least one R-substituted cyclopentadienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, cyclohexadienyl, phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, cycloheptadienyl or cyclooctadienyl. 10a
[0345] In an embodiment, in Formula 1-1, Formula 1A and Formula 1B, at least one R 1a can be deuterium; or multiple Rs 1a can be bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group. 10a 60
[0346] For example, in Formula 1-1, Formula 1A and Formula 1B, one, two, three, four or five Rs 1a can each be deuterium; or multiple Rs 1a can be bonded to each other to form an unsubstituted or at least one R-substituted cyclopentadienyl, cyclohexadienyl or cycloheptadienyl. 10a
[0347] In an embodiment, in Formula 1-1, Formula 1A and Formula 1B, at least one R 1c can be tert-butyl, or multiple Rs 1c can be bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group. 10a 60
[0348] For example, in Formula 1-1, Formula 1A and Formula 1B, one, two, three, four or five Rs 1c can each be tert-butyl; or multiple Rs 1c can be bonded to each other to form an unsubstituted or at least one R-substituted cyclopentadienyl, cyclohexadienyl or cycloheptadienyl. 10a
[0349] In an embodiment, in Formula 1, Formula 1-1, Formula 1-2, Formula 1A, Formula 1B and Formula 1C, multiple R1s may not be directly bonded to each other; multiple R2s may not be directly bonded to each other; multiple R3s may not be directly bonded to each other; multiple R4s may not be directly bonded to each other; multiple Rs 1d may not be directly bonded to each other; multiple Rs 1e may not be directly bonded to each other; multiple Rs 1f may not be directly bonded to each other; R 11 and R 12 may not be directly bonded to each other; R 13 and R 14 may not be directly bonded to each other; R 14 and R 15 may not be directly bonded to each other; and R 15 and R 16 may not be directly bonded to each other.
[0350] In embodiments, in Formula 1-1, multiple Rs 1a are bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group. Examples of the compound may include Compound BD23:
[0351]
[0352] In embodiments, in Formula 1-1, multiple Rs 1c are bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group. Examples of the compound may include Compound BD21:
[0353]
[0354] In embodiments, in Formula 1-1, multiple Rs 1a are bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, and in Formula 1-1, multiple Rs 1c are bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group. Examples of the compound may include Compound BD24:
[0355]
[0356] In an embodiment, in Formula 1A and Formula 1B, by
[0357] The portion represented may be the portion represented by formula AS:
[0358] [Formula AS]
[0359]
[0360] In formula AS,
[0361] X 17 、X 18 and X 19 may each be the same as defined in formula 1A and formula 1B,
[0362] X 11a may be N or C(R 11a ), X 12a may be N or C(R 12a ), X 13a may be N or C(R 13a ), X 14a may be N or C(R 14a ), X 15a may be N or C(R 15a ), X 11c may be N or C(R 11c ), X 12c may be N or C(R 12c ), X 13c may be N or C(R 13c ), X 14c may be N or C(R 14c ), and X 15c may be N or C(R 15c ),
[0363] R 11a to R 15a may each independently be the same as described with reference to R 1a in formula 1-1,
[0364] R 11c to R 15c may each independently be the same as described with reference to R 1c in formula 1-1,
[0365] R 11a and R 12a 、R 12a and R 13a 、R 13a and R 14a as well as R 14a and R 15a may each optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60A carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0366] R 11c and R 12c 、R 12c and R 13c 、R 13c and R 14c and R 14c and R 15c may each optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, and
[0367] * indicates the bonding site to the ring CY1 in Formula 1.
[0368] In an embodiment, the moiety represented by Formula AS may be the moiety represented by Formula AS1:
[0369] [Formula AS1]
[0370]
[0371] In Formula AS1,
[0372] X 17 、X 18 and X 19 may each be the same as defined in Formulas 1A and 1B,
[0373] R 11a to R 15a may each independently be the same as described with reference to R 1a in Formula 1-1,
[0374] R 11c to R 15c may each independently be the same as described with reference to R 1c in Formula 1-1,
[0375] R 13a and R 14a may optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C2-C8 monocyclic group, and
[0376] R 13c and R 14c may optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C2-C8 monocyclic group.
[0377] In an embodiment, in formula AS1, R 13a , R 14a , R 12c , R 13c and R 14c may each independently be unsubstituted or substituted by the following C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl or any combination thereof.
[0378] In an embodiment, in formula AS1, R 11a to R 15a at least one of which may each independently be deuterium or deuterium-substituted C1-C 60 alkyl, and R 11c to R 15c at least one of which may be tert-butyl.
[0379] In an embodiment, in formula 1C,
[0380] X 13e may be C(R 13e ), and R 13e may be phenyl substituted by at least one of deuterium and tert-butyl;
[0381] X 14f may be C(R 14f ), and R 14f may be phenyl substituted by at least one of deuterium and tert-butyl; or
[0382] X 13e may be C(R 13e ), X 14f may be C(R 14f ), and R 13e and R 14f may each independently be phenyl substituted by at least one of deuterium and tert-butyl.
[0383] For example, R 13e and R 14f may each independently be composed of A group represented, where * indicates the bonding site to an adjacent atom.
[0384] In an embodiment, ring CY2 can be phenyl, pyridyl, pyrimidinyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, dibenzosilolyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzocarbazolyl, benzofluorenyl, naphthobenzosilolyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzocarbazolyl, dibenzofluorenyl, dinaphthosilolyl, azadibenzofuranyl, azadibenzothiophenyl, azacarbazolyl, azafuorenyl, azadibenzosilolyl, azanaphthobenzofuranyl, azanaphthobenzothiophenyl, azabenzocarbazolyl, azabenzofluorenyl, azanaphthobenzosilolyl, azadinaphthofuranyl, azadinaphthothiophenyl, azadibenzocarbazolyl, azadibenzofluorenyl or azadinaphthosilolyl.
[0385] In an embodiment, in Formula 1, the moiety represented by can be the moiety represented by Formula 2-1:
[0386] [Formula 2-1]
[0387]
[0388] In Formula 2-1,
[0389] X 21 can be N or C(R 21 ), X 22 can be N or C(R 22 ), X 23 can be N or C(R 23 ), and X2 is the same as defined in Formula 1,
[0390] R 21 to R 23 can each independently be the same as described for R2 in Formula 1,
[0391] R 21 and R 22 at least one of which can each independently be deuterium, methyl, ethyl, propyl, methyl substituted with at least one deuterium, ethyl substituted with at least one deuterium or propyl substituted with at least one deuterium,
[0392] * indicates the bonding site to M in Formula 1,
[0393] *’ indicates the bonding site to ring CY1 in Formula 1, and
[0394] *” indicates the bonding site to T1 in Formula 1.
[0395] In an embodiment, in Formula 1, ring CY3 can be:
[0396] a C2-C8 monocyclic group; or
[0397] a C4-C polycyclic group in which two or three C2-C8 monocyclic groups are fused to each other 20 polycyclic group.
[0398] In an embodiment, in Formula 1, ring CY3 may be phenyl, pyridyl, pyrimidinyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, dibenzosilolyl, azadibenzofuranyl, azadibenzothiophenyl, azacarbazolyl, azafuorenyl or azadibenzosilolyl.
[0399] In an embodiment, in Formula 1, the moiety represented by may be a moiety represented by one of Formula 3A to Formula 3F:
[0400] [Formula 3A]
[0401]
[0402] [Formula 3B]
[0403]
[0404] [Formula 3C]
[0405]
[0406] [Formula 3D]
[0407]
[0408] [Formula 3E]
[0409]
[0410] [Formula 3F]
[0411]
[0412] In Formulas 3A to 3F,
[0413] X 31 may be N or C(R 31 ), X 32 may be N or C(R 32 ), X 33 may be N or C(R 33 ), X 34 may be N or C(R 34 ), X 35 may be N or C(R 35 ), X 36 may be N or C(R 36 ), and X37 may be N or C(R 37 ),
[0414] R 31 to R 37 may each independently be the same as described for R3 in Formula 1,
[0415] * indicates the bonding site to M in Formula 1,
[0416] *’ indicates the bonding site to T1 in Formula 1, and
[0417] *” indicates the bonding site to ring CY4 in Formula 1.
[0418] In an embodiment, in Formulas 3A to 3F, X 31 to X 37 at least one of which may each be N.
[0419] In an embodiment, in Formulas 3A to 3F, R 31 to R 37 at least one of which may be deuterium.
[0420] In an embodiment, in Formula 1, ring CY4 may be phenyl, pyridyl, pyrimidinyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, dibenzosilolyl, azadibenzofuranyl, azadibenzothiophenyl, azacarbazolyl, azaf luorenyl or azadibenzosilolyl.
[0421] In an embodiment, in Formula 1, the moiety represented by may be the moiety represented by Formula 4-1:
[0422] [Formula 4-1]
[0423]
[0424] In Formula 4-1,
[0425] X 41 may be N or C, X 42 may be N or C(R 42 ), X 43 may be N or C(R 43 ), X 44 may be N or C(R 44 ), and X 45 may be N or C(R 45 ),
[0426] R 42 to R 45 may each independently be the same as described for R4 in Formula 1, and X4 is the same as defined in Formula 1,
[0427] *Indicates the bonding site of M in Formula 1, and
[0428] *’ indicates the bonding site of the ring CY3 in Formula 1.
[0429] In an embodiment, in Formula 4-1, R 42 to R 45 at least one of which may each independently be an unsubstituted or substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl or any combination thereof. For example, R 43 may be tert-butyl.
[0430] In an embodiment, the organometallic compound represented by Formula 1 may satisfy Condition B-1:
[0431] [Condition B-1]
[0432] In Formula 1, at least one of the R2s in number a2 may each independently be deuterium, methyl, ethyl, propyl, methyl substituted with at least one deuterium, ethyl substituted with at least one deuterium, or propyl substituted with at least one deuterium.
[0433] In an embodiment, the organometallic compound represented by Formula 1 may satisfy Condition B-2:
[0434] [Condition B-2]
[0435] In Formula 1, at least one of the R2s in number a2 may each independently be deuterium, methyl, ethyl, methyl substituted with at least one deuterium, or ethyl substituted with at least one deuterium.
[0436] In an embodiment, the organometallic compound represented by Formula 1 may satisfy Condition B-3:
[0437] [Condition B-3]
[0438] In Formula 1, at least one of the R2s in number a2 may each independently be -CH3, -CH2D, -CHD2 or -CD3.
[0439] Corresponding to where in Condition A, in Formula 1 by The represented portion may be an organometallic compound represented by Formula 1, which is an embodiment of the portion represented by Formula 1-1, and may satisfy Condition B-1, Condition B-2, and Condition B-3.
[0440] In an embodiment, the organometallic compound represented by Formula 1 may include at least one deuterium atom.
[0441] In an embodiment, the organometallic compound represented by Formula 1 may satisfy both Condition A and Condition B. For example, the organometallic compound represented by Formula 1 is significantly different from a compound that does not satisfy any of Condition A and Condition B, a compound that satisfies Condition A but does not satisfy Condition B, or a compound that does not satisfy Condition A but satisfies Condition B.
[0442] Figure 1 It is a graph showing the result of measuring the charge amount (i.e., the corresponding capacitance) of a light-emitting device including an organometallic compound according to the structure of the organometallic compound.
[0443] Reference Figure 1 , when measuring the capacitance by applying a voltage to a light-emitting device (e.g., including a second compound to a fourth compound) including a blue phosphorescent dopant (or sensitizer) that does not satisfy both Condition A and Condition B, the injection of holes may be relatively fast in the low voltage region. As a result, a hump may occur in the low voltage region, leading to an increase in capacitance and charge amount. In this regard, the charge amount can be calculated according to Equation 1 of Evaluation Example 1 described below. When the capacitance and charge amount increase, RC delay may occur at a high scan rate.
[0444] Therefore, in order to provide a light-emitting device with low capacitance and low charge amount, a case where the negative giant surface potential (negative GSP) effect increases, which slows down the injection of holes, can be considered. The negative GSP can move the region where the hump occurs to a high voltage region by slowing down the injection of holes, and can reduce the maximum value of the capacitance (C max ).
[0445] Reference Figure 1 , when measuring the capacitance by applying a voltage to a light-emitting device (e.g., including a second compound to a fourth compound) including a blue phosphorescent dopant (or sensitizer) that satisfies Condition A but does not satisfy Condition B, or including a blue phosphorescent dopant (or sensitizer) that does not satisfy Condition A but satisfies Condition B, the negative GSP effect may occur.
[0446] As a blue phosphorescent dopant (or sensitizer), a light-emitting device including an organometallic compound represented by Formula 1 that satisfies both Condition A and Condition B (e.g., including a second compound to a fourth compound) exhibits a large negative GSP effect, which not only shifts the region where a hump occurs to a high-voltage region, but also can effectively reduce the maximum value of capacitance (C max ). Therefore, the organometallic compound represented by Formula 1 that satisfies both Condition A and Condition B can improve the capacitance and charge amount of the light-emitting device. As a result, the possibility of RC delay in an electronic device including the light-emitting device can be effectively reduced, thereby improving the display quality. For example, an embodiment can determine conditions for the structure of a blue phosphorescent dopant (or sensitizer) for improving the capacitance and charge amount of the light-emitting device.
[0447] [Examples of Compounds]
[0448] In an embodiment, the organometallic compound represented by Formula 1 can be one of Compound BD1 to Compound BD27.
[0449]
[0450]
[0451]
[0452] Among Compound BD1 to Compound BD16 and Compound BD25 to Compound BD27,
[0453] Ar1 can be a group represented by .
[0454] Ar2 can be a group represented by .
[0455] Ar3 can be a group represented by .
[0456] Ar4 can be a group represented by , and
[0457] * in Ar1 to Ar4 indicates the bonding site with an adjacent atom.
[0458] In an embodiment, the second compound can be one of Compound ETH1 to Compound ETH100.
[0459]
[0460]
[0461]
[0462]
[0463] In an embodiment, the third compound may be one of compounds HTH1 to HTH46.
[0464]
[0465]
[0466] In an embodiment, the fourth compound may be one of compounds DFD1 to DFD30.
[0467]
[0468]
[0469] Among compounds ETH1 to ETH100, compounds HTH1 to HTH46, and compounds DFD1 to DFD30, Me represents methyl, Ph represents phenyl, D represents deuterium, D4 represents substitution with four deuterium atoms, and D5 represents substitution with five deuterium atoms. For example, the group represented by -Ph-D5 and the group represented by may each be the same as the group represented by respectively.
[0470] Figure 2 description]
[0471] Figure 2 is a schematic cross-sectional view of the light-emitting device 10 according to an embodiment. The light-emitting device 10 may include a first electrode 110, an intermediate layer, and a second electrode 150. The intermediate layer may include a hole transport region 120, an emission layer 130, and an electron transport region 140.
[0472] Hereinafter, with reference to Figure 2 the structure and manufacturing method of the light-emitting device 10 according to an embodiment will be described.
[0473] [First electrode 110]
[0474] In Figure 2 a substrate may be further included under the first electrode 110 or on the second electrode 150. In an embodiment, the substrate may be a glass substrate or a plastic substrate. In an embodiment, the substrate may be a flexible substrate. For example, the substrate may 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.
[0475] The first electrode 110 can be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, a high work function material that facilitates hole injection can be used as the material for forming the first electrode 110.
[0476] The first electrode 110 can be a reflective electrode, a semi-transmissive 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 semi-transmissive 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.
[0477] The first electrode 110 can have a single-layer structure composed of a single layer or a multi-layer structure including multiple layers. In an embodiment, the first electrode 110 can have a three-layer structure of ITO / Ag / ITO.
[0478] [Interlayer]
[0479] The interlayer can be disposed on the first electrode 110. The interlayer can include a hole transport region 120, an emission layer 130, and an electron transport region 140.
[0480] The interlayer can include various organic materials, metal-containing compounds (such as, organometallic compounds), inorganic materials (such as, quantum dots), and the like.
[0481] In an embodiment, the interlayer can include at least two emission units stacked between the first electrode 110 and the second electrode 150 and at least one charge generation layer between adjacent emission units among the two or more emission units. As described above, when the interlayer includes at least two emission units and at least one charge generation layer, the light-emitting device 10 can be a tandem light-emitting device.
[0482] [Hole transport region 120]
[0483] The hole transport region 120 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 multiple layers containing different materials.
[0484] The hole transport region 120 can include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof.
[0485] In an embodiment, the hole transport region 120 may have a multi-layer structure including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, where the layers of each structure may be stacked from the first electrode 110 in the order described for each, but the structure of the hole transport region 120 is not limited thereto.
[0486] In an embodiment, the hole transport region 120 may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0487] [Formula 201]
[0488]
[0489] [Formula 202]
[0490]
[0491] In Formulas 201 and 202,
[0492] L 201 to L 204 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0493] L 205 may be *-O-*’, *-S-*’, *-N(Q 201 )-*’, an unsubstituted or at least one R 10a substituted C1-C 20 alkylene group, an unsubstituted or at least one R 10a substituted C2-C 20 alkenylene group, an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0494] xa1 to xa4 may each independently be an integer selected from 0 to 5,
[0495] xa5 may be an integer selected from 1 to 10,
[0496] R 201 to R 204 and Q 201may each independently be unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group or unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group,
[0497] R 201 and R 202 may optionally be linked to each other via a single bond, an unsubstituted or R-substituted C1-C5 alkylene group or an unsubstituted or R-substituted C2-C5 alkenylene group to form an unsubstituted or R-substituted C8-C 10a substituted C1-C5 alkylene group or an unsubstituted or R 10a substituted C2-C5 alkenylene group to form an unsubstituted or R 10a substituted C8-C 60 polycyclic group (e.g., carbazolyl) (e.g., compound HT16),
[0498] R 203 and R 204 may optionally be linked to each other via a single bond, an unsubstituted or R 10a substituted C1-C5 alkylene group or an unsubstituted or R 10a substituted C2-C5 alkenylene group to form an unsubstituted or R 10a substituted C8-C 60 polycyclic group, and
[0499] na1 may be an integer selected from 1 to 4.
[0500] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of the groups represented by Formula CY201 to Formula CY217:
[0501]
[0502] In Formulas CY201 to CY217, R 10b and R 10c may each independently be the same as described for reference R 10a The ring CY 201 to the ring CY 204 may each independently be a C3-C 20 carbocyclic group or a C1-C 20 heterocyclic group, and at least one hydrogen in Formulas CY201 to CY217 may be unsubstituted or substituted by R as described herein 10a substituted.
[0503] In an embodiment, in Formulas CY201 to CY217, the ring CY 201 to the ring CY 204Each may independently be phenyl, naphthyl, phenanthryl, or anthryl.
[0504] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may include at least one of the groups represented by Formula CY201 to Formula CY203.
[0505] In an embodiment, the compound represented by Formula 201 may include at least one of the groups represented by Formula CY201 to Formula CY203 and at least one of the groups represented by Formula CY204 to Formula CY217.
[0506] In an embodiment, in Formula 201, xa1 may be 1, and R 201 may be a group represented by one of Formula CY201 to Formula CY203, xa2 may be 0, and R 202 may be a group represented by one of Formula CY204 to Formula CY207.
[0507] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the groups represented by Formula CY201 to Formula CY203.
[0508] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the groups represented by Formula CY201 to Formula CY203, and may each independently include at least one of the groups represented by Formula CY204 to Formula CY217.
[0509] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the groups represented by Formula CY201 to Formula CY217.
[0510] In an embodiment, the hole transport region 120 may include one of Compound HT1 to Compound HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4’,4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), or any combination thereof:
[0511]
[0512]
[0513]
[0514]
[0515]
[0516] The thickness of the hole transport region 120 can be in the range of about to about For example, the thickness of the hole transport region 120 can be in the range of about to about When the hole transport region 120 includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer can be in the range of about to about and the thickness of the hole transport layer can be in the range of about to about For example, the thickness of the hole injection layer can be in the range of about to about For example, the thickness of the hole transport layer can be in the range of about to about When the thickness of the hole transport region 120, the thickness of the hole injection layer, and the thickness of the hole transport layer are within the above ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0517] The emission assist layer can be used to increase the light emission efficiency by compensating for the optical resonance distance according to the wavelength of the light emitted by the emission layer 130. The electron blocking layer can be used to prevent electrons from the emission layer 130 from leaking into the hole transport region 120. The materials that can be included in the hole transport region 120 can be included in the emission assist layer and the electron blocking layer.
[0518] [p-dopant]
[0519] In addition to the aforementioned materials, the hole transport region 120 can further include a charge generation material for improving the conductive characteristics. The charge generation material can be uniformly or non-uniformly dispersed in the hole transport region 120 (e.g., in the form of a single layer composed of the charge generation material).
[0520] The charge generation material can be, for example, a p-dopant.
[0521] For example, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant can be less than or equal to about -3.5 eV.
[0522] In an embodiment, the p-dopant can include a quinone derivative, a cyanide-containing compound, a compound including element EL1 and element EL2, or any combination thereof.
[0523] Examples of the quinone derivatives may include TCNQ and F4-TCNQ.
[0524] Examples of the cyano group-containing compounds may include HAT-CN and the compound represented by Formula 221.
[0525]
[0526] [Formula 221]
[0527]
[0528] In Formula 221,
[0529] R 221 to R 223 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, and
[0530] R 221 to R 223 at least one of which may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group each substituted by the following: cyano group; -F; -Cl; -Br; -I; a C1-C 20 alkyl group substituted by a cyano group, -F, -Cl, -Br, -I or any combination thereof; or any combination thereof.
[0531] In the compound including element EL1 and element 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.
[0532] Examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); post-transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); and lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
[0533] Examples of metalloids may include silicon (Si), antimony (Sb), and tellurium (Te).
[0534] Examples of non-metals may include oxygen (O) and halogens (e.g., F, Cl, Br, I, etc.).
[0535] Examples of compounds including element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or any combination thereof.
[0536] Examples of metal oxides may 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.), rhenium oxides (e.g., ReO3, etc.), etc.
[0537] Examples of metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.
[0538] Examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.
[0539] Examples of alkaline earth metal halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2.
[0540] Examples of transition metal halides may 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.).
[0541] Examples of post-transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (e.g., InI3, etc.), tin halides (e.g., SnI2, etc.), etc.
[0542] Examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, etc.
[0543] Examples of metalloid halides may include antimony halides (e.g., SbCl5, etc.).
[0544] Examples of metal tellurides may 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.).
[0545] [Emission layer 130]
[0546] When the light-emitting device 10 is a full-color light-emitting device, the emission layer 130 may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer according to sub-pixels. In an embodiment, the emission layer 130 may have a stacked structure of two or more layers among a red emission layer, a green emission layer, and a blue emission layer, where the two or more layers may be in contact with each other or may be separated from each other to emit white light. In an embodiment, the emission layer 130 may include two or more materials among a red light-emitting material, a green light-emitting material, and a blue light-emitting material, where the two or more materials may be mixed with each other in a single layer to emit white light.
[0547] The emission layer 130 may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0548] Based on 100 parts by weight of the host, the amount of the dopant in the emission layer 130 can be in the range of about 0.01 part by weight to about 15 parts by weight.
[0549] In an embodiment, the emission layer 130 may include quantum dots.
[0550] The emission layer 130 may include a delayed fluorescence material. The delayed fluorescence material may be used as a host or a dopant in the emission layer 130.
[0551] The thickness of the emission layer 130 may be in the range of about to about . For example, the thickness of the emission layer 130 may be in the range of about to about . When the thickness of the emission layer 130 is within the above range, excellent light-emitting characteristics can be obtained without significantly increasing the driving voltage.
[0552] [Host]
[0553] In an embodiment, the host may include a compound represented by Formula 301:
[0554] [Formula 301]
[0555] [Ar 301 xb11 -[(L 301 ) xb1 -R 301 xb21 .
[0556] In Formula 301,
[0557] Ar 301 and L 301 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0558] xb11 may be 1, 2 or 3,
[0559] xb1 may be an integer selected from 0 to 5,
[0560] R 301 may be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, an unsubstituted or at least one R 10a substituted C1-C 60 alkyl group, an unsubstituted or at least one R 10a substituted C2-C 60 alkenyl group, an unsubstituted or at least one R10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, -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 ),
[0561] xb21 may be an integer selected from 1 to 5, and
[0562] Q 301 To Q 303 Each may independently be the same as described with reference to Q1.
[0563] In an embodiment, in Formula 301, when xb11 is 2 or greater, two or more Ar 301 Can be connected to each other via a single bond.
[0564] In an embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0565] [Formula 301-1]
[0566]
[0567] [Formula 301-2]
[0568]
[0569] In Formula 301-1 and Formula 301-2,
[0570] Ring A 301 To Ring A 304 may be each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60Heterocyclic group
[0571] X 301 can be O, S, N[(L 304 ) xb4 -R 304 , C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0572] xb22 and xb23 can each independently be 0, 1 or 2,
[0573] L 301 , xb1 and R 301 can each be the same as described in the specification,
[0574] L 302 to L 304 can each independently be the same as that described with reference to L 301 .
[0575] xb2 to xb4 can each independently be the same as that described with reference to xb1, and
[0576] R 302 to R 305 and R 311 to R 314 can each independently be the same as that described with reference to R 301 .
[0577] In an embodiment, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In an embodiment, the host may include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0578] In an embodiment, the host may include one of compounds H1 to H128, 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-bis(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis(carbazol-9-yl)benzene (mCP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), or any combination thereof:
[0579]
[0580]
[0581]
[0582]
[0583]
[0584]
[0585]
[0586] [Phosphorescent dopant]
[0587] The phosphorescent dopant may include at least one transition metal as the central metal.
[0588] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0589] The phosphorescent dopant may be electrically neutral.
[0590] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0591] [Formula 401]
[0592] M(L 401 ) xc1 (L 402 ) xc2
[0593] [Formula 402]
[0594]
[0595] In Formulas 401 and 402,
[0596] M may be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
[0597] L 401 may be a ligand represented by Formula 402, and xc1 may be 1, 2, or 3, where when xc1 is 2 or greater, two or more L 401 may be the same as or different from each other,
[0598] L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3, or 4, where when xc2 is 2 or greater, two or more L 402 may be the same as or different from each other,
[0599] X 401 and X 402 may each independently be nitrogen or carbon,
[0600] Ring A 401 and Ring A 402 can each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0601] T 401 can be a single bond, *-O-*’, *-S-*’, *-C(=O)-*’, *-N(Q 411 ))-*’, *-C(Q 411 )(Q 412 )-*’, *-C(Q 411 )=C(Q 412 )-*’, *-C(Q 411 )=*’ or *=C=*’,
[0602] X 403 and X 404 can each independently be a chemical bond (e.g., a covalent bond or a coordination bond), O, S, N(Q 413 ), B(Q 413 ), P(Q 413 ), C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),
[0603] Q 411 to Q 414 can each independently be the same as described for reference Q1,
[0604] R 401 and R 402 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, an unsubstituted or at least one R 10a substituted C1-C 20 alkyl group, an unsubstituted or at least one R 10a substituted C1-C 20 alkoxy group, an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group, an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q401 ), -S(=O)2(Q 401 ), or -P(=O)(Q 401 )(Q 402 ),
[0605] Q 401 to Q 403 can each independently be the same as described with reference to Q1,
[0606] xc11 and xc12 can each independently be an integer selected from 0 to 10, and
[0607] * and *' in formula 402 each indicate the bonding site to M in formula 401.
[0608] For example, in formula 402, X 401 can be nitrogen and X 402 can be carbon, or X 401 and X 402 can each be nitrogen.
[0609] In an embodiment, in formula 401, when xc1 is 2 or greater, two or more of the two rings A 401 in L 401 can optionally be connected together by T 402 as a linking group, and the two rings A 402 can optionally be connected together by T 403 as a linking group (see compound PD1 to compound PD4 and compound PD7). T 402 and T 403 can each independently be the same as described with reference to T 401 described.
[0610] In formula 401, L 402 can be an organic ligand. In an embodiment, L 402 can include a halogen group, a diketone group (e.g., acetylacetonate group), a carboxylic acid group (e.g., picolinate group), -C(=O), an isocyano group, a -CN group, a phosphorus-containing group (e.g., phosphine group, phosphite group, etc.) or any combination thereof.
[0611] In an embodiment, the phosphorescent dopant can include, for example, one or any combination of compounds PD1 to PD39:
[0612]
[0613]
[0614]
[0615] [Fluorescent dopant]
[0616] The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
[0617] In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:
[0618] [Formula 501]
[0619]
[0620] In Formula 501,
[0621] Ar 501 , L 501 to L 503 , R 501 and R 502 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0622] xd1 to xd3 may each independently be 0, 1, 2, or 3, and
[0623] xd4 may be 1, 2, 3, 4, 5, or 6.
[0624] In an embodiment, in Formula 501, Ar 501 may be a fused ring group in which three or more monocyclic groups are fused together (e.g., anthryl, 1,2-benzophenanthryl, pyrenyl, etc.).
[0625] In an embodiment, in Formula 501, xd4 may be 2.
[0626] In an embodiment, the fluorescent dopant may include one of Compound FD1 to Compound FD37, DPVBi, DPAVBi, or any combination thereof:
[0627]
[0628]
[0629]
[0630] [Thermally activated delayed fluorescence material]
[0631] The emission layer 130 may include a thermally activated delayed fluorescence material.
[0632] In an embodiment, the thermally activated delayed fluorescence material may be selected from compounds capable of emitting thermally activated delayed fluorescence based on the thermally activated delayed fluorescence emission mechanism.
[0633] The delayed fluorescence material included in the emission layer 130 can be used as a host or a dopant, depending on the type of other materials included in the emission layer 130.
[0634] 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 in the range of about 0 eV to about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material is within the above range, upconversion from the triplet state to the singlet state of the delayed fluorescence material can occur effectively, and thus, the light-emitting device 10 can have improved luminous efficiency.
[0635] 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 ring group such as a carbazolyl group) and at least one electron acceptor (e.g., a sulfinyl 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 ring groups that are fused to each other and share boron (B).
[0636] In an embodiment, the delayed fluorescence material can include, for example, at least one of Compounds DF1 to DF14:
[0637]
[0638]
[0639] [Quantum dots]
[0640] The emission layer 130 can include quantum dots.
[0641] In the specification, the quantum dots can be crystals of semiconductor compounds. Depending on the size of the crystals, the quantum dots can emit light of various emission wavelengths. By adjusting the ratio of the elements constituting the quantum dots, the quantum dots can also emit light of various emission wavelengths.
[0642] The diameter of the quantum dots can be in the range of, for example, about 1 nm to about 10 nm.
[0643] The quantum dots can be synthesized by a wet chemical process, a metal - organic chemical vapor deposition (MOCVD) process, a molecular beam epitaxy (MBE) process, or any process similar thereto.
[0644] The wet chemical process is a method that includes mixing precursor materials with an organic solvent and growing quantum dot particle crystals. When the quantum dot particle crystals grow, the organic solvent is naturally used as a dispersant coordinated on the surface of the quantum dot particle crystals, and the growth of the quantum dot particle crystals is controlled so that the growth of the quantum dot particle crystals can be controlled by a process that is less costly and easier to perform than vapor deposition methods (such as, for example, metalorganic chemical vapor deposition (MOCVD) process or molecular beam epitaxy (MBE) process).
[0645] Quantum dots can include Group II-VI semiconductor compounds, Group III-V semiconductor compounds, Group III-VI semiconductor compounds, Group I-III-VI semiconductor compounds, Group IV-VI semiconductor compounds, Group IV elements or compounds, or any combination thereof.
[0646] Examples of Group II-VI semiconductor compounds can include: binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; or any combination thereof.
[0647] Examples of group III-V semiconductor compounds can include: binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb; or any combination thereof. In an embodiment, the group III-V semiconductor compound may further include a group II element. Examples of group III-V semiconductor compounds further including a group II element can include InZnP, InGaZnP, and InAlZnP.
[0648] Examples of group III-VI semiconductor compounds can include: binary compounds such as GaS, Ga2S3, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, etc.; ternary compounds such as InGaS3, InGaSe3, etc.; or any combination thereof.
[0649] 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, AgAlO2, etc.; quaternary compounds such as AgInGaS2, AgInGaSe2, etc.; or any combination thereof.
[0650] 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; or any combination thereof.
[0651] Examples of Group IV elements or compounds may include: single-element materials such as Si, Ge, etc.; binary compounds such as SiC, SiGe, etc.; or any combination thereof.
[0652] Each element included in a compound (e.g., a binary compound, a ternary compound, or a quaternary compound) may be present in the particles at a uniform concentration or a non-uniform concentration. In an embodiment, the above formula refers to the type of elements included in the compound, where the element ratio in the compound may vary. For example, AgInGaS2 may refer to AgIn x Ga 1-x S2 (where 0 < x < 1).
[0653] In an embodiment, the quantum dots may have a single structure in which the concentration of each element in the quantum dots is uniform, or the quantum dots may have a core-shell structure. In an embodiment, in the case where the quantum dots have a core-shell structure, the material included in the core and the material included in the shell may be different from each other.
[0654] The shell of the quantum dots can be used as a protective layer to prevent chemical denaturation of the core to maintain semiconductor characteristics, and / or can be used as a charging layer to impart electrophoretic characteristics to the quantum dots. The shell can be a single layer or multiple layers. The interface between the core and the shell may have a concentration gradient in which the concentration of the material present in the shell decreases towards the center of the core.
[0655] Examples of the shell of the quantum dots may include metal oxides, non-metal oxides, semiconductor compounds, or any combination thereof. Examples of metal oxides or non-metal oxides may include: binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, etc.; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, etc.; or any combination thereof.
[0656] Examples of semiconductor compounds may include Group III-VI semiconductor compounds, Group II-VI semiconductor compounds, Group III-V semiconductor compounds, Group I-III-VI semiconductor compounds, Group IV-VI semiconductor compounds, or any combination thereof as described herein. For example, semiconductor compounds may 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.
[0657] The quantum dots may have a full width at half maximum (FWHM) of the emission wavelength spectrum less than or equal to about 45 nm. For example, the quantum dots may have an FWHM of the emission wavelength spectrum less than or equal to about 40 nm. For example, the quantum dots may have an FWHM of the emission wavelength spectrum less than or equal to about 30 nm. When the FWHM of the emission wavelength spectrum of the quantum dots is within any of these ranges, the quantum dots may have improved color purity and / or improved color reproducibility. The light emitted by the quantum dots may be emitted in all directions, improving the wide viewing angle.
[0658] In an embodiment, the quantum dots may be in the form of spheres, cones, multi-armed forms, or cubes, or the quantum dots may be in the form of nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates.
[0659] Since the band gap can be controlled by adjusting the size of the quantum dots or the ratio of elements in the quantum dot compound, light of various wavelengths can be obtained from the emission layer 130 containing the quantum dots. Therefore, by using the aforementioned quantum dots (using quantum dots of different sizes or quantum dots with different element ratios in the quantum dot compound), a light-emitting device that emits light of various wavelengths can be implemented. In an embodiment, the size of the quantum dots or the ratio of elements in the quantum dot compound may be selected to emit red, green, and / or blue light. In an embodiment, the size of the quantum dots may be configured to emit white light through a combination of lights of various colors.
[0660] [Electron transport region 140]
[0661] The electron transport region 140 may have a single-layer structure composed of a single layer including a single material, a single-layer structure composed of a single layer including different materials, or a multi-layer structure including multiple layers containing different materials.
[0662] The electron transport region 140 may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0663] In an embodiment, the electron transport region 140 may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, where the layers of each structure may be sequentially stacked from the emission layer 130 in the order in which they are respectively described, but the structure of the electron transport region 140 is not limited thereto.
[0664] The electron transport region 140 (e.g., the buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region 140) may include a metal-free compound including at least one π-deficient nitrogen-containing C1-C 60 heterocyclic group.
[0665] In an embodiment, the electron transport region 140 may include a compound represented by Formula 601.
[0666] [Formula 601]
[0667] [Ar 601 xe11 -[(L 601 ) xe1 -R 601 xe21
[0668] In Formula 601,
[0669] Ar 601 and L 601 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0670] xe11 can be 1, 2, or 3,
[0671] xe1 can be 0, 1, 2, 3, 4, or 5,
[0672] R 601 can be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group, an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), or -P(=O)(Q 601 )(Q 602 ),
[0673] Q 601 to Q 603 can each independently be the same as described for reference Q1,
[0674] xe21 can be 1, 2, 3, 4, or 5, and
[0675] Ar 601 、L 601 and R 601 at least one of which can each independently be an unsubstituted or at least one R 10a substituted π-deficient nitrogen-containing C1-C 60 heterocyclic group.
[0676] In an embodiment, in Formula 601, when xe11 is 2 or greater, two or more Ar 601 may be linked together via a single bond.
[0677] In an embodiment, in Formula 601, Ar 601 may be unsubstituted or substituted by at least one R 10a substituted anthryl.
[0678] In an embodiment, the electron transport region 140 may include a compound represented by Formula 601-1:
[0679] [Formula 601-1]
[0680]
[0681] In Formula 601-1,
[0682] 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 at least one of X 614 to X 616 may each be N,
[0683] L 611 to L 613 may each independently be the same as described with reference to L 601 ,
[0684] xe611 to xe613 may each independently be the same as described with reference to xe1,
[0685] R 611 to R 613 may each independently be the same as described with reference to R 601 , and
[0686] R 614 to R 616 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group or unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group.
[0687] In an embodiment, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 can each independently be 0, 1, or 2.
[0688] In an embodiment, the electron transport region 140 can include one of Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
[0689]
[0690]
[0691]
[0692]
[0693] The thickness of the electron transport region 140 can be in the range of about to about For example, the thickness of the electron transport region 140 can be in the range of about to about When the electron transport region 140 includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the thickness of the hole blocking layer, or the thickness of the electron control layer can each independently be in the range of about to about and the thickness of the electron transport layer can be in the range of about to about For example, the thickness of the buffer layer, the thickness of the hole blocking layer, or the thickness of the electron control layer can each independently be in the range of about to about For example, the thickness of the electron transport layer can be in the range of about to about When the thickness of the buffer layer, the thickness of the hole blocking layer, the thickness of the electron control layer, the thickness of the electron transport layer, and / or the thickness of the electron transport region 140 are within these ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.
[0694] In addition to the aforementioned materials, the electron transport region 140 (e.g., the electron transport layer in the electron transport region 140) can further include a metal-containing material.
[0695] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, an Rb ion, or a Cs ion, and the metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, an Sr ion, or a Ba ion.
[0696] The ligand coordinated with the metal ion of the alkali metal complex or with the metal ion of the alkaline earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0697] In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1(Liq) or compound ET-D2:
[0698]
[0699] The electron transport region 140 may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may contact (e.g., directly contact) the second electrode 150.
[0700] The electron injection layer may have a single-layer structure composed of a single layer (composed of a single material), a single-layer structure composed of a single layer including different materials, or a multi-layer structure including multiple layers containing different materials.
[0701] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0702] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0703] The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
[0704] The alkali metal compound may include: alkali metal oxides such as Li2O, Cs2O or K2O; alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI or KI; or any combination thereof. The alkaline earth metal compound may include alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1) or Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1). The rare earth metal compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3 or any combination thereof. In an embodiment, the rare earth metal compound may include lanthanide metal tellurides. Examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3 and Lu2Te3.
[0705] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include: alkali metal ions, alkaline earth metal ions or rare earth metal ions; and ligands bonded to the metal ions (e.g., hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof).
[0706] The electron injection layer may be composed of an alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof as described above. In an embodiment, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
[0707] In an embodiment, the electron injection layer may be composed of an alkali metal compound (e.g., an alkali metal halide); or the electron injection layer may be composed of an alkali metal compound (e.g., an alkali metal halide) and an alkali metal, alkaline earth metal, rare earth metal or any combination thereof. In an embodiment, the electron injection layer may be a KI:Yb co-deposited layer, a RbI:Yb co-deposited layer or a LiF:Yb co-deposited layer, etc.
[0708] When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0709] The thickness of the electron injection layer may be in the range of about to about For example, the thickness of the electron injection layer may be in the range of about to about When the thickness of the electron injection layer is within any of the above ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0710] [Second Electrode 150]
[0711] The second electrode 150 may be disposed over the electron transport region 140. The second electrode 150 may be a cathode serving as an electron injection electrode. When the second electrode 150 is a cathode, the material used to form the second electrode 150 may include a material having a low work function, such as a metal, an alloy, a conductive compound, or any combination thereof.
[0712] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0713] The second electrode 150 may have a single-layer structure or a multi-layer structure.
[0714] [Capping Layer]
[0715] The light-emitting device 10 may include a first capping layer outside the first electrode 110, and / or a second capping layer outside the second electrode 150. For example, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer, and the second electrode 150 are stacked in this order, a structure in which the first electrode 110, the interlayer, the second electrode 150, and the second capping layer are stacked in this order, or a structure in which the first capping layer, the first electrode 110, the interlayer, the second electrode 150, and the second capping layer are stacked in this order.
[0716] The light generated in the emission layer 130 of the light-emitting device 10 can pass through the first electrode 110 (which can be a semi-transmissive electrode or a transmissive electrode), and pass through the first capping layer to the outside. The light generated in the emission layer 130 of the light-emitting device 10 can pass through the second electrode 150 (which can be a semi-transmissive electrode or a transmissive electrode), and pass through the second capping layer to the outside.
[0717] The first capping layer and the second capping layer can each increase the external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, thereby increasing the luminous efficiency of the light-emitting device 10.
[0718] The first capping layer and the second capping layer can each include a material having a refractive index greater than or equal to about 1.2 (relative to a wavelength of about 460 nm).
[0719] 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.
[0720] At least one of the first capping layer and the second capping layer can each independently include a carbocyclic compound, a heterocyclic compound, an amino group-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 amino group-containing compound can each optionally be 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 amino group-containing compound.
[0721] 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.
[0722] In an embodiment, at least one of the first capping layer and the second capping layer can each independently include one of Compound HT28 to Compound HT33, one of Compound CP1 to Compound CP6, β-NPB, or any combination thereof:
[0723]
[0724] [Film]
[0725] The electronic device can further include a film. The film 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, or a quantum dot-containing layer, etc.), a light-blocking member (e.g., a light reflection layer or a light absorption layer, etc.), a protection member (e.g., an insulating layer or a dielectric layer, etc.).
[0726] [Electronic device]
[0727] The light-emitting device 10 may be included in various electronic devices. In an embodiment, the electronic device including the light-emitting device 10 may be a display device or an authentication device.
[0728] In addition to the light-emitting device 10, the electronic device (e.g., a display device) may further include a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and / or the color conversion layer may be disposed in at least one direction in which the light emitted from the light-emitting device 10 travels. For example, the light emitted from the light-emitting device 10 may be blue light or white light. The light-emitting device 10 may be the light-emitting device described herein. In an embodiment, the color conversion layer may include quantum dots. The quantum dots may be, for example, the quantum dots described herein.
[0729] The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixels, the color filter may include a plurality of color filter regions respectively corresponding to the plurality of sub-pixels, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixels.
[0730] A pixel defining film may be disposed between the plurality of sub-pixels to define each sub-pixel.
[0731] The color filter may further include a plurality of color filter regions and a plurality of light-shielding patterns disposed between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a plurality of light-shielding patterns disposed between the plurality of color conversion regions.
[0732] The plurality of color filter regions (or the plurality of color conversion regions) may include a first region that emits a first color light, a second region that emits a second color light, and / or a third region that emits a third color light, where the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths from each other. In an embodiment, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the plurality of color filter regions (or the plurality of color conversion regions) may include quantum dots. In an embodiment, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. The quantum dots may be the quantum dots described herein. The first region, the second region, and / or the third region may each further include a scatterer.
[0733] In an embodiment, the light-emitting device 10 may emit first light, a first region may absorb the first light to emit first-first color light, a second region may absorb the first light to emit second-first color light, and a third region may absorb the first light to emit third-first color light. In an embodiment, the first-first color light, the second-first color light, and the third-first color light may have maximum emission wavelengths different from each other. In an embodiment, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
[0734] In addition to the light-emitting device 10, the electronic device may further include a thin-film transistor. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode 110 and the second electrode 150 of the light-emitting device 10.
[0735] The thin-film transistor may further include a gate electrode, a gate insulating film, and the like.
[0736] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and the like.
[0737] The electronic device may further include a sealing portion for sealing the light-emitting device 10. The sealing portion may be disposed between the color filter and / or the color conversion layer and the light-emitting device 10. The sealing portion may allow the light from the light-emitting device 10 to be extracted to the outside, and may prevent environmental air and / or moisture from penetrating into the light-emitting device 10. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic device may be flexible.
[0738] According to the use of the electronic device, in addition to the color filter and / or the color conversion layer, various functional layers may be further included on the sealing portion. Examples of the functional layer may include a touch screen layer and a polarization layer. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (such as a fingertip, a pupil, etc.).
[0739] In addition to the light-emitting device 10 as described above, the authentication device may further include a biometric information collector.
[0740] The electronic device can be applied to various displays, light sources, lighting devices, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical tools (e.g., electronic thermometers, sphygmomanometers, glucometers, pulse measurement devices, pulse wave measurement devices, electrocardiogram monitors, ultrasonic diagnostic devices or endoscope monitors), fish finders, various measuring tools, meters (e.g., meters for vehicles, aircraft, and ships), and projectors, etc.
[0741] [Electronic equipment]
[0742] The light-emitting device 10 can be included in various electronic equipment.
[0743] For example, the electronic equipment including the light-emitting device 10 can be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall including a plurality of displays spliced together, a theater screen or a stadium screen, a light therapy device or a signboard.
[0744] Because the light-emitting device 10 has improved color purity, improved luminous efficiency, improved lifespan, etc., the electronic equipment including the light-emitting device 10 can have high brightness, high resolution, and low power consumption.
[0745] Figure 3 and Figure 4 description]
[0746] Figure 3 is a schematic cross-sectional view of an electronic device according to an embodiment.
[0747] Figure 3 The electronic device in can include a substrate 100, a thin film transistor TFT, a light-emitting device, and a packaging part 300.
[0748] 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 the penetration of impurities through the substrate 100 and can provide a flat surface on the substrate 100.
[0749] 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.
[0750] The active layer 220 may include an inorganic semiconductor (e.g., silicon or polysilicon), an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0751] The gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be provided on the active layer 220, and the gate electrode 240 may be provided on the gate insulating film 230.
[0752] The interlayer insulating film 250 may be provided on the gate electrode 240. The interlayer insulating film 250 may be located between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260, and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
[0753] The source electrode 260 and the drain electrode 270 may be provided on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may 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 may respectively contact the exposed portions of the source region and the drain region of the active layer 220.
[0754] The TFT may be electrically connected to the light-emitting device to drive the light-emitting device, and may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light-emitting device may be provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an interlayer, and a second electrode 150.
[0755] The first electrode 110 may be provided on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270 and may expose a part of the drain electrode 270. The first electrode 110 may be electrically connected to the exposed portion of the drain electrode 270.
[0756] The pixel defining film 290 including an insulating material may be provided on the first electrode 110. The pixel defining film 290 may expose a specific region of the first electrode 110, and the interlayer may be formed in the exposed region of the first electrode 110. The pixel defining film 290 may be a polyimide-based organic film or a polyacrylic acid organic film. Although not shown in Figure 3 , at least some layers of the interlayer may extend to the upper portion of the pixel defining film 290 and may be provided in the form of a common layer.
[0757] The second electrode 150 may be provided on the interlayer, and a capping layer 170 may further be included on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0758] The encapsulation part 300 may be disposed on the cover layer 170. The encapsulation part 300 may be disposed on the light-emitting device to protect the light-emitting device from moisture and / or oxygen. The encapsulation part 300 may include: an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate or polyacrylic acid, etc.), epoxy resin (e.g., aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or any combination of the inorganic film and the organic film.
[0759] Figure 4 is a schematic cross-sectional view of an electronic device according to another embodiment.
[0760] Figure 4 The electronic device in Figure 3 may be different from the electronic device in Figure 4 at least in that it further includes a light-shielding pattern 500 and a functional region 400 on the encapsulation part 300. The functional region 400 may be a color filter region, a color conversion region, or a combination of the color filter region and the color conversion region. In an embodiment,
[0761] Figure 5 description of
[0762] Figure 5 is a schematic perspective view of an electronic apparatus 1 including a light-emitting device according to an embodiment. The electronic apparatus 1, which may be a device for displaying moving images or still images, may be not only a portable electronic device such as a mobile phone, a smart phone, a tablet computer, a mobile communication terminal, an electronic notebook computer, an e-book, a portable multimedia player (PMP), a navigation device, or an ultra-mobile personal computer (UMPC), but also various products such as a television, a laptop computer, a monitor, a billboard, or an Internet of Things (IoT) device. The electronic apparatus 1 may be such a product or any part thereof.
[0763] The electronic apparatus 1 may be a wearable device (e.g., a smart watch, a watch phone, a glasses-type display, or a head-mounted display (HMD)) or a part of a wearable device. However, the embodiment is not limited thereto.
[0764] In an embodiment, the electronic device 1 can be an instrument panel of a vehicle, a center information display (CID) arranged on a center console or an instrument panel of the vehicle, an in-vehicle mirror display replacing a side view mirror of the vehicle, an entertainment display for a rear seat of the vehicle, a display arranged on a backrest of a front seat of the vehicle, a head-up display (HUD) mounted in front of the vehicle or projected on a front windshield, or a computer-generated hologram augmented reality head-up display (CGH AR HUD). For the sake of convenience of explanation, Figure 5 An embodiment is illustrated in which the electronic device 1 is a smart phone.
[0765] The electronic device 1 can include a display area DA and a non-display area NDA outside the display area DA. The electronic device 1 can implement an image by pixels of a two-dimensional array arranged in the display area DA.
[0766] The non-display area NDA can be an area where no image is displayed and can surround (e.g., completely surround) the display area DA. A driver for providing an electrical signal or power to a display element arranged in the display area DA can be arranged in the non-display area NDA. Pads for electrically connecting electronic components or a printed circuit board can be arranged in the non-display area NDA.
[0767] In the electronic device 1, the length in the x-axis direction and the length in the y-axis direction can be different from each other. In an embodiment, as Figure 5 shown, the length in the x-axis direction can be less 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 an embodiment, the length in the x-axis direction can be greater than the length in the y-axis direction.
[0768] Figure 6 and Figures 7A to 7C description]
[0769] Figure 6 FIG. is a schematic perspective view of the exterior of a vehicle 1000 as an electronic device including a light-emitting device according to an embodiment. Figures 7A to 7C Each is a schematic diagram of the interior of the vehicle 1000 in Figure 6 according to an embodiment.
[0770] Referring to Figure 6 and Figures 7A to 7C , embodiments 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 vehicles traveling on roads or tracks, boats moving on the sea or a river, and airplanes flying in the air using the action of air, etc.
[0771] The vehicle 1000 can travel on a road or a track. The vehicle 1000 can move in a selectable direction according to the rotation of at least one wheel. Examples of the vehicle 1000 can include a three-wheeled vehicle or a four-wheeled vehicle, an engineering machine, a two-wheeled vehicle, a prime mover, a bicycle, and a train traveling on a track.
[0772] The vehicle 1000 can include a body having an interior and an exterior, and a chassis that is a part outside the body and on which mechanical equipment necessary for driving is installed. The exterior of the vehicle body can include a front panel, an engine hood, a roof panel, a rear panel, a trunk, and pillars provided at the boundaries between the doors, etc. The chassis of the vehicle 1000 can include a power generation device, a power transmission device, a drive 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.
[0773] 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.
[0774] The side window glasses 1100 and the front window glass 1200 can be separated by pillars arranged between the side window glasses 1100 and the front window glass 1200.
[0775] The side window glasses 1100 can be installed on the sides of the vehicle 1000. In an embodiment, the side window glasses 1100 can be installed on the doors 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 arranged adjacent to the instrument panel 1400, and the second side window glass 1120 can be arranged adjacent to the passenger seat instrument panel 1600.
[0776] In an embodiment, the side window glasses 1100 can be spaced apart from each other in the x-axis direction or in the direction opposite to the x-axis direction (-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 in the -x-axis direction. For example, an imaginary straight line L connecting the side window glasses 1100 can extend in the x-axis direction or in the -x-axis direction. In an embodiment, an imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 can extend in the x-axis direction or in the -x-axis direction.
[0777] The front window glass 1200 can be installed in the front of the vehicle 1000. The front window glass 1200 can be arranged between the side window glasses 1100 that face each other.
[0778] The side mirror 1300 can provide a view of the rear of the vehicle 1000. The side mirror 1300 can be mounted on the exterior of the vehicle body. In an embodiment, multiple side mirrors 1300 can be provided. One of the multiple side mirrors 1300 can be arranged outside the first side window glass 1110. Another one of the multiple side mirrors 1300 can be arranged outside the second side window glass 1120.
[0779] The instrument panel 1400 can be arranged 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 indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a driving record system, an automatic gear selector indicator, a door open warning light, an oil warning light, and / or a low fuel warning light.
[0780] 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 can be provided. The center console 1500 can be arranged on one side of the instrument panel 1400.
[0781] The passenger seat instrument panel 1600 can be spaced apart from the instrument panel 1400, and the center console 1500 is arranged between the passenger seat instrument panel 1600 and the instrument panel 1400. In an embodiment, the instrument panel 1400 can be arranged corresponding to the driver's seat (not shown), and the passenger seat instrument panel 1600 can be arranged corresponding to the 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.
[0782] In an embodiment, the display device 2 can include a display panel 3, and the display panel 3 can display an image. The display device 2 can be arranged inside the vehicle 1000. In an embodiment, the display device 2 can be arranged between the side window glasses 1100 facing each other. The display device 2 can be arranged on at least one of the instrument cluster 1400, the center console 1500, and the passenger seat instrument panel 1600.
[0783] The display device 2 can include an organic light emitting display device, an inorganic electroluminescent (EL) display device, a quantum dot display device, etc. Hereinafter, as the display device 2 according to an embodiment, a light emitting display device including a light emitting device according to an embodiment will be described as an example. However, various types of display devices as described herein can be used in an embodiment.
[0784] Reference Figure 7A , the display device 2 can be provided on the center console 1500. In an embodiment, the display device 2 can display navigation information. In an embodiment, the display device 2 can display information about audio settings, video settings, or vehicle settings.
[0785] ReferenceFigure 7B The display device 2 can be arranged on the dashboard 1400. In an embodiment, the dashboard 1400 can display driving information and the like through the display device 2. For example, the dashboard 1400 can implement driving information digitally. The dashboard 1400 can digitally display vehicle information and driving information as images. In an embodiment, the pointer and meter of the tachometer and various warning light icons can be displayed through digital signals.
[0786] Reference Figure 7C The display device 2 can be arranged on the passenger seat dashboard 1600. The display device 2 can be embedded in the passenger seat dashboard 1600 or arranged on the passenger seat dashboard 1600. In an embodiment, the display device 2 arranged on the passenger seat dashboard 1600 can display an image related to the information displayed on the dashboard 1400 and / or the information displayed on the center console 1500. In an embodiment, the display device 2 arranged on the passenger seat dashboard 1600 can display information different from the information displayed on the dashboard 1400 and / or the information displayed on the center console 1500.
[0787] [Manufacturing method]
[0788] By using various methods (such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI)), the layers included in the hole transport region 120, the emission layer 130, and the layers included in the electron transport region 140 can be formed in a selected region.
[0789] When forming the layers included in the hole transport region 120, the emission layer 130, and the layers included in the electron transport region 140 by vacuum deposition, depending on the materials included in the layer to be formed and the structure of the layer to be formed, the deposition can be performed at a deposition temperature of about 100 °C to about 500 °C, a vacuum degree of about 10 -8 torr to about 10 -3 torr, and a deposition rate of about / s to about / s.
[0790] [Definition of terms]
[0791] As used herein, the term "C3-C 60 carbocyclic group" can be a cyclic group composed only of carbon atoms as ring-forming atoms and having 3 to 60 carbon atoms. For example, C3-C 50 carbocyclic group, C3-C 40 carbocyclic group, C3-C 30 carbocyclic group, C3-C 20 carbocyclic group, or C3-C 10 carbocyclic group.
[0792] As used herein, the term "C1-C 60 heterocyclic group" may be a cyclic group having 1 to 60 carbon atoms and may further include at least one heteroatom as a ring-forming atom in addition to carbon atoms. For example, C1-C 50 heterocyclic group, C1-C 40 heterocyclic group, C1-C 30 heterocyclic group, C1-C 20 heterocyclic group or C1-C 10 heterocyclic group.
[0793] C3-C 60 carbocyclic group and C1-C 60 heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are fused to each other. For example, C1-C 60 heterocyclic group may have 3 to 61 ring-forming atoms.
[0794] As used herein, the term "cyclic group" may be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group.
[0795] As used herein, the term "π-electron-rich C3-C 60 cyclic group" may be a cyclic group having 3 to 60 carbon atoms and may not include *-N=*' as a ring-forming moiety.
[0796] As used herein, the term "nitrogen-containing π-electron-deficient C1-C 60 heterocyclic group" may be a heterocyclic group having 1 to 60 carbon atoms and may include *-N=*' as a ring-forming moiety.
[0797] In an embodiment,
[0798] C3-C 60 carbocyclic group may be a T1 group, or a group in which two or more T1 groups are fused to each other (e.g., cyclopentadienyl, adamantyl, norbornyl, phenyl, pentaphenylenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, perylenyl, pentaphenyl, heptaphenylenyl, tetracenyl, picenyl, hexaphenyl, pentacenyl, rubicenyl, corannulenyl, ovalenyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indeno[1,2,3-cd]anthracenyl or indeno[1,2,3-def]phenanthrenyl),
[0799] C1-C 60The heterocyclic group may be a T2 group, a group in which two or more T2 groups are fused to each other, or a group in which at least one T2 group and at least one T1 group are fused to each other (e.g., pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthylindolyl, isoindolyl, benzisoindolyl, naphthylisoindolyl, benzosilolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuryl, indolocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilolocarbazolyl, benzindolocarbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, benzonaphthosilolyl, benzofurodibenzofuryl, benzofurodibenzothienyl, benzothienodibenzothienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafuryl, azadibenzosilolyl, azadibenzothienyl, azadibenzofuryl, xanthenyl, etc.).
[0800] The π - electron - rich C3 - C 60 The cyclic group may be a T1 group, a group in which two or more T1 groups are fused to each other, a T3 group, a group in which two or more T3 groups are fused to each other, or a group in which at least one T3 group and at least one T1 group are fused to each other (e.g., C3 - C 60 carbocyclic group, 1H - pyrrolyl, silolyl, borole, 2H - pyrrolyl, 3H - pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthylindolyl, isoindolyl, benzisoindolyl, naphthylisoindolyl, benzosilolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuryl, indolocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilolocarbazolyl, benzindolocarbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, benzonaphthosilolyl, benzofurodibenzofuryl, benzofurodibenzothienyl, benzothienodibenzothienyl, etc.).
[0801] The π - electron - deficient nitrogen - containing C1 - C 60The heterocyclic group may be a T4 group, a group in which two or more T4 groups are fused to each other, a group in which at least one T4 group and at least one T1 group are fused to each other, a group in which at least one T4 group and at least one T3 group are fused to each other, or a group in which at least one T4 group, at least one T1 group, and at least one T3 group are fused to each other (for example, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorene, azadibenzosilolyl, azadibenzothiophenyl, azadibenzofuranyl, etc.).
[0802] The T1 group may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, or phenyl.
[0803] The T2 group may be furyl, thienyl, 1H-pyrrolyl, silolyl, borole, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilolyl, azaborole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridyl, dihydropyridyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl, or dihydropyridazinyl.
[0804] The T3 group may be furyl, thienyl, 1H-pyrrolyl, silolyl, or borole.
[0805] The T4 group may be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilolyl, azaborole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or tetrazinyl.
[0806] As used herein, the terms "cyclic group", "C3-C60 "carbocyclic group", "C1-C" 60 "heterocyclic group", "π-electron rich C3-C" 60 "cyclic group" or "nitrogen-containing π-electron deficient C1-C" 60 "heterocyclic group" refers to a monovalent or polyvalent group (e.g., divalent, trivalent, tetravalent, etc.) that is fused (e.g., joined together) with a cyclic group, depending on the structure of the formula in which the corresponding term is used.
[0807] In an embodiment, "phenyl" may be benzo group, phenyl or phenylene, etc., which can be readily understood by those of ordinary skill in the art according to the structure of the formula including "phenyl".
[0808] Monovalent C3-C 60 carbocyclic group or monovalent C1-C 60 Examples of the heterocyclic group may include C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group.
[0809] Divalent C3-C 60 carbocyclic group or divalent C1-C 60 Examples of the heterocyclic group may include C3-C 10 subcycloalkyl, C1-C 10 subheterocycloalkyl, C3-C 10 subcycloalkenyl, C1-C 10 subheterocycloalkenyl, C6-C 60 subaryl, C1-C 60 subheteroaryl, divalent non-aromatic fused polycyclic group and divalent non-aromatic fused heteropolycyclic group.
[0810] As used herein, the term "C1-C" 60 "alkyl" may be a straight-chain or branched-chain aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, e.g., C1-C 50 alkyl, C1-C 30 alkyl, C1-C 20 alkyl or C1-C 10alkyl, and examples thereof may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, and tert-decyl.
[0811] As used herein, the term "C1-C 60 alkylene" may be a divalent group having the same structure as C1-C 60 alkyl.
[0812] As used herein, the term "C2-C 60 alkenyl" may be a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end of C2-C 60 alkyl, for example, C2-C 30 alkenyl, C2-C 20 alkenyl or C2-C 10 alkenyl, and examples thereof may include vinyl, propenyl, and butenyl.
[0813] As used herein, the term "C2-C 60 alkenylene" may be a divalent group having the same structure as C2-C 60 alkenyl.
[0814] As used herein, the term "C2-C 60 alkynyl" may be a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end of C2-C 60 alkyl, for example, C2-C 30 alkynyl, C2-C 20 alkynyl or C2-C 10 alkynyl, and examples thereof may include ethynyl and propynyl.
[0815] As used herein, the term "C2-C 60 alkynylene" may be a divalent group having the same structure as C2-C 60 alkynyl.
[0816] As used herein, the term "C1-C 60 alkoxy" may be a monovalent group represented by -O(A 101 )(where A 101 may be C1-C 60 alkyl), for example, C1-C 30 alkoxy, C1-C 20 alkoxy or C1-C 10an alkoxy group, and examples thereof may include a methoxy group, an ethoxy group, and an isopropoxy group.
[0817] As used herein, the term "C3-C 10 cycloalkyl" may be a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group.
[0818] As used herein, the term "C3-C 10 subcycloalkyl" may be a divalent group having the same structure as C3-C 10 cycloalkyl.
[0819] As used herein, the term "C1-C 10 heterocycloalkyl" may be a monovalent cyclic group having 1 to 10 carbon atoms and further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and examples thereof may include a 1,2,3,4-oxadiazolyl group, a tetrahydrofuryl group, and a tetrahydrothienyl group.
[0820] As used herein, the term "C1-C 10 subheterocycloalkyl" may be a divalent group having the same structure as C1-C 10 heterocycloalkyl.
[0821] As used herein, the term "C3-C 10 cycloalkenyl" may be a monovalent cyclic group having 3 to 10 carbon atoms, at least one carbon-carbon double bond, and no aromaticity in its ring structure, and examples thereof may include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.
[0822] As used herein, the term "C3-C 10 subcycloalkenyl" may be a divalent group having the same structure as C3-C 10 cycloalkenyl.
[0823] As used herein, the term "C1-C 10 heterocycloalkenyl" may be a monovalent cyclic group having 1 to 10 carbon atoms, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and having at least one double bond. Examples of C1-C 10 heterocycloalkenyl may include a 4,5-dihydro-1,2,3,4-oxadiazolyl group, a 2,3-dihydrofuryl group, and a 2,3-dihydrothienyl group.
[0824] As used herein, the term "C1-C 10"Hetrocycloalkenylene" may be a divalent group having the same structure as the cycloalkenylene. 10 The cycloalkenylene has the same structure as the divalent group.
[0825] As used herein, the term "C6-C 60 Aryl" may be a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. For example, C6-C 50 Aryl, C6-C 40 Aryl, C6-C 30 Aryl, C6-C 20 Aryl or C6-C 15 Aryl.
[0826] As used herein, the term "C6-C 60 Arylene" may be a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms.
[0827] C6-C 60 Examples of C6-C aryl may include phenyl, pentaphenylenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthrenyl, perylenyl, pentaphenyl, heptaphenylenyl, tetraphenylenyl, picenyl, hexaphenylenyl, pentaphenyl, rubicenyl, coronenyl, and ovalenyl.
[0828] When C6-C 60 Aryl and C6-C 60 Arylene each include two or more rings, each of the two or more rings may be fused to each other.
[0829] As used herein, the term "C1-C 60 Heteroaryl" may be a monovalent group of a heteroaromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a ring-forming atom in addition to carbon atoms. For example, C1-C 50 Heteroaryl, C1-C 40 Heteroaryl, C1-C 30 Heteroaryl, C1-C 20 Heteroaryl or C1-C 10 Heteroaryl.
[0830] As used herein, the term "C1-C 60 Heteroarylene" may be a divalent group of a heteroaromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a ring-forming atom in addition to carbon atoms.
[0831] C1-C 60Examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, and naphthyridinyl.
[0832] When C1-C 60 When the heteroaryl group and the C1-C 60 When each of the heteroaryl group and the C1-C heteroarylene group includes two or more rings, each of the two or more rings may be fused to each other.
[0833] As used herein, the term "monovalent non-aromatic fused polycyclic group" may be a monovalent group having two or more rings fused to each other, with only carbon atoms (e.g., 8 to 60 carbon atoms) as ring-forming atoms and having no aromaticity in its molecular structure when considered as a whole, e.g., C8-C 60 The monovalent non-aromatic fused polycyclic group, C8-C 50 The monovalent non-aromatic fused polycyclic group, C8-C 40 The monovalent non-aromatic fused polycyclic group, C8-C 30 The monovalent non-aromatic fused polycyclic group or C8-C 20 The monovalent non-aromatic fused polycyclic group. Examples of the monovalent non-aromatic fused polycyclic group may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenoanthracenyl, and indenoacenaphthylenyl.
[0834] As used herein, the term "divalent non-aromatic fused polycyclic group" may be a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.
[0835] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" may be a monovalent group having two or more rings fused to each other, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms (e.g., having 1 to 60 carbon atoms) and having no aromaticity in its molecular structure when considered as a whole, e.g., C1-C 60 The monovalent non-aromatic fused heteropolycyclic group, C1-C 50 The monovalent non-aromatic fused heteropolycyclic group, C1-C 40 The monovalent non-aromatic fused heteropolycyclic group, C1-C 30 The monovalent non-aromatic fused heteropolycyclic group or C1-C 20Monovalent non-aromatic fused heteropolycyclic group. Examples of the monovalent non-aromatic fused heteropolycyclic group may include pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthylindolyl, isoindolyl, benzisoindolyl, naphthylisoindolyl, benzosilolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuryl, azacarbazolyl, azafuryl, azadibenzosilolyl, azadibenzothienyl, azadibenzofuryl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indolocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilolocarbazolyl, benzindolocarbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, benzonaphthosilolyl, benzofurodibenzofuryl, benzofurodibenzothienyl, and benzothienodibenzothienyl.
[0836] As used herein, the term "divalent non-aromatic fused heteropolycyclic group" may be a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.
[0837] As used herein, the term "C6-C 60 aryloxy" may be a group represented by -O(A 102 )(where A 102 may be C6-C 60 aryl), for example, C6-C 50 aryloxy, C6-C 40 aryloxy, C6-C 30 aryloxy, C6-C 20 aryloxy or C6-C 15 aryloxy.
[0838] As used herein, the term "C6-C 60 arylthio" may be a group represented by -S(A 103 )(where A 103 may be C6-C 60 aryl), for example, C6-C 50 arylthio, C6-C 40 arylthio, C6-C 30 arylthio, C6-C 20 arylthio or C6-C 15 arylthio.
[0839] As used herein, the term "C7-C 60 aralkyl" may be represented by -(A104 )(A 105 )(wherein A 104 may be a C1-C 54 alkylene group, and A 105 may be a C6-C 59 aryl group), for example, a C7-C 50 aralkyl group, a C7-C 40 aralkyl group, a C7-C 30 aralkyl group, a C7-C 20 aralkyl group, or a C7-C 15 aralkyl group.
[0840] As used herein, the term "C2-C 60 heteroaralkyl" may be a group 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), for example, a C2-C 50 heteroaralkyl group, a C2-C 40 heteroaralkyl group, a C2-C 30 heteroaralkyl group, a C2-C 20 heteroaralkyl group, or a C2-C 15 heteroaralkyl group.
[0841] In the specification, the group term "R 10a " may be:
[0842] deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro;
[0843] each unsubstituted or substituted by the following C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0844] Each unsubstituted or substituted C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group or C2-C 60 heteroaralkyl group: deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, -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
[0845] -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 ).
[0846] In the specification, groups Q1 to Q3, Q11 to Q 13 、Q 21 to Q 23 and Q 31 to Q 33 may each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; or unsubstituted or substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl or C2-C 60 heteroaralkyl: deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl or any combination thereof.
[0847] As used herein, the term "heteroatom" can be any atom other than a carbon atom and a hydrogen atom. Examples of heteroatoms can include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0848] As used herein, the term "transition metal" can include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and gold (Au).
[0849] Throughout the specification, "D" refers to deuterium, "Ph" refers to phenyl, "Me" refers to methyl, "Et" refers to ethyl, "tert-Bu", " t Bu" or "Bu t " each refers to tert-butyl, and "OMe" refers to methoxy.
[0850] As used herein, the term "biphenyl" can be "phenyl-substituted phenyl". For example, "biphenyl" can be a substituted phenyl having a C6-C 60 aryl as a substituent.
[0851] As used herein, the term "terphenyl" can be "biphenyl-substituted phenyl". For example, the term "terphenyl" can be a substituted phenyl, where the substituent is a C6-C 60 aryl-substituted C6-C 60 aryl, and a substituted phenyl where there are two substituents, and each substituent is a C6-C 60 aryl.
[0852] Unless otherwise specified, as used herein, the symbols *, *', and *" each refer to the bonding site of an adjacent atom in the corresponding formula or moiety.
[0853] In the specification, the x-axis, y-axis, and z-axis are not limited to the three axes in an orthogonal coordinate system (e.g., a Cartesian coordinate system), and 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.
[0854] Hereinafter, the organometallic 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.
[0855] Synthesis Example 1 (Synthesis of Compound BD1)
[0856] Synthesis of Intermediate I-1-1
[0857]
[0858] 55 g of 1-bromo-2-fluoro-3-nitrobenzene (1.0 equivalent (eq)), 2-bromophenylboronic acid (1.2 eq), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.05 eq), and sodium carbonate (2.0 eq) were suspended in a 0.25 M mixed solution of 800 ml of dioxane (i.e., 1,4-dioxane) and 200 ml of distilled water, and heated to 100 °C for 12 hours in an N2 atmosphere. After cooling the mixture to room temperature (r.t.), distilled water was added thereto, the organic layer was extracted using ethyl acetate, and the extracted organic layer was washed with an aqueous saturated sodium chloride solution and dried over magnesium sulfate. The resulting product was purified by column chromatography (dichloromethane / hexane (volume ratio 1:99)) to obtain Intermediate I-1-1 (yield: 97%).
[0859] Synthesis of Intermediate I-1-2
[0860]
[0861] Intermediate I-1-1 (1.0 eq), bis(pinacolato)diboron (B2Pin2) (1.2 eq), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl2) (0.05 eq) and potassium acetate (KOAc) (2.0 eq) were suspended in 0.2 M dioxane and heated to 100 °C under a N2 atmosphere for 12 h. After cooling the mixture to room temperature (r.t.), distilled water was added thereto, the organic layer was extracted with ethyl acetate, and the extracted organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The resultant was purified by column chromatography (methylene chloride / hexane (volume ratio 1:99)) to obtain Intermediate I-1-2 (yield: 77%).
[0862] Synthesis of Intermediate I-1-3
[0863]
[0864] Intermediate I-1-2 (1.0 eq), 1-bromo-2-iodobenzene (3.0 eq), Pd(dppf)Cl2 (0.05 eq) and tripotassium phosphate (K3PO4) (3.0 eq) were suspended in a 0.1 M mixed solution of 400 ml of dioxane and 100 ml of distilled water and heated to 100 °C under a N2 atmosphere for 5 h. After cooling the mixture to room temperature (r.t.), distilled water was added thereto, the organic layer was extracted with ethyl acetate, and the extracted organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The resultant was purified by column chromatography (methylene chloride / hexane (volume ratio 1:99)) to obtain Intermediate I-1-3 (yield: 74%).
[0865] Synthesis of Intermediate I-1-4
[0866]
[0867] 2-Bromo-6-chloroaniline (1.0 eq), B2Pin2 (1.2 eq), Pd(dppf)Cl2 (0.05 eq) and KOAc (2.0 eq) were suspended in 0.2 M dioxane and heated to 100 °C under a N2 atmosphere for 12 h. After cooling the mixture to room temperature (r.t.), distilled water was added thereto, the organic layer was extracted with ethyl acetate, and the extracted organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The resultant was purified by column chromatography (methylene chloride / hexane (volume ratio 1:99)) to obtain Intermediate I-1-4 (yield: 77%).
[0868] Synthesis of Intermediate I-1-5
[0869]
[0870] Intermediate I-1-3 (1.0 eq), Intermediate I-1-4 (1.1 eq), chloro(2-dicyclohexylphosphino-2’,6’-dimethoxy-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(II) (SphosPdG2) (0.05 eq) and K3PO4 (6.0 eq) were suspended in a mixed solution of 400 ml of tetrahydrofuran (THF) and 100 ml of distilled water, and heated to 60 °C in an N2 atmosphere for 3 hours. After cooling the mixture to room temperature (r.t.), distilled water was added thereto, the organic layer was extracted using ethyl acetate, and the extracted organic layer was washed with an aqueous saturated sodium chloride solution and dried over magnesium sulfate. The resultant was purified by column chromatography (dichloromethane / hexane (volume ratio 1:99)) to obtain Intermediate I-1-5 (yield: 74%).
[0871] Synthesis of Intermediate I-1-6
[0872]
[0873] Intermediate I-1-5 (1.0 eq) and cesium carbonate (3.0 eq) were suspended in dimethyl sulfoxide (DMSO), and heated to 150 °C in an N2 atmosphere for 3 hours. After cooling the mixture to room temperature (r.t.), distilled water was added thereto, the organic layer was extracted using ethyl acetate, and the extracted organic layer was washed with an aqueous saturated sodium chloride solution and dried over magnesium sulfate. The resultant was purified by column chromatography (dichloromethane / hexane (volume ratio 1:99)) to obtain Intermediate I-1-6 (yield: 73%).
[0874] Synthesis of Intermediate I-1-7
[0875]
[0876] Intermediate I-1-6 (1.0 eq), 3,5-di-tert-butylphenylboronic acid (1.2 eq), SphosPdG2 (0.1 eq) and K3PO4 (7.0 eq) were suspended in a mixed solution of 150 ml of THF and 300 ml of distilled water, and heated to 90 °C in an N2 atmosphere for 3 hours. After cooling the mixture to room temperature (r.t.), distilled water was added thereto, the organic layer was extracted using ethyl acetate, and the extracted organic layer was washed with an aqueous saturated sodium chloride solution and dried over magnesium sulfate. The resultant was purified by column chromatography (dichloromethane / hexane (volume ratio 1:99)) to obtain Intermediate I-1-7 (yield: 98%).
[0877] Synthesis of Intermediate I-1-8
[0878]
[0879] Dissolve intermediate I-1-7 (1.0 eq) in 0.1 M ethanol, and dropwise add an aqueous solution of 37% hydrochloric acid by mass fraction (5.0 eq) thereto. Add tin (3.0 eq) to the reaction mixture and stir at 80 °C for 12 hours by raising the temperature. When the reaction is completed, cool the reaction result to room temperature and neutralize with 1 N sodium hydroxide solution. Extract the organic layer with dichloromethane and distilled water, and dry the extracted organic layer with magnesium sulfate to obtain intermediate I-1-8 (yield: 71%). Without further purification, use the obtained intermediate I-1-8 for the next reaction.
[0880] Synthesis of intermediate I-1-9
[0881]
[0882] Suspend intermediate I-1-8 (1.0 eq), 2-(5-bromo-2-methylphenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-D4-carbazole (1.1 eq), tris(dibenzylideneacetone) dipalladium(0) (Pd2(dba)3) (0.05 eq), 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl (SPhos) (0.1 eq) and sodium tert-butoxide (NaO t Bu) (2.0 eq) in 250 ml of toluene, and heat to 110 °C for 5 hours in an N2 atmosphere. After cooling the mixture to room temperature, extract the organic layer with ethyl acetate and water, and wash the extracted organic layer with an aqueous saturated sodium chloride solution and dry with magnesium sulfate. Purify the resulting product by column chromatography (ethyl acetate / hexane (volume ratio 10:90)) to obtain intermediate I-1-9 (yield: 88%).
[0883] Synthesis of intermediate I-1-10
[0884]
[0885] Dissolve intermediate I-1-9 (1.0 eq) in 25 ml of triethyl orthoformate (HC(OEt)3) (50.0 eq), and dropwise add 5 ml of 12 N hydrochloric acid (1.2 eq) thereto. Heat the reaction mixture to 80 °C and stir for 12 hours. When the reaction is completed, remove the solvent therefrom under reduced pressure, and extract the organic layer with ethyl acetate and distilled water. Dry the organic layer with magnesium sulfate, and purify the resulting product by column chromatography (methanol / dichloromethane (volume ratio 5:95)) to obtain intermediate I-1-10 (yield: 82%).
[0886] Synthesis of Compound BD1
[0887]
[0888] Intermediate I-1-10 (1.0 eq), 2,6-dimethylpyridine (2.0 eq) and potassium tetrachloroplatinate (K2PtCl4) (1.05 eq) were suspended in 200 ml of ortho-dichlorobenzene (ODCB), and stirred at 125 °C for 24 hours by raising the temperature. When the reaction was completed, the solvent was removed therefrom under reduced pressure, and the organic layer was extracted with ethyl acetate and distilled water. The resulting product was dried over magnesium sulfate and purified by column chromatography (dichloromethane / hexane (volume ratio 50:50)) to obtain Compound BD1 (yield: 47%).
[0889] Synthesis Example 2 (Synthesis of Compound BD3)
[0890] Compound BD3 (yield: 74%) was obtained in substantially the same manner as in Synthesis Example 1, except that 3,5-di-tert-butylphenylboronic acid-D3 was used instead of 3,5-di-tert-butylphenylboronic acid in the synthesis of Intermediate I-1-7 in Synthesis Example 1.
[0891]
[0892] Synthesis Example 3 (Synthesis of Compound BD17)
[0893] Synthesis of Intermediate I-17-1
[0894]
[0895] 15 g of 2,6-dibromo-4-tert-butylaniline (1.0 eq), phenyl-D5-boronic acid (1.1 eq), tetrakis(triphenylphosphine)palladium(0) (0.020 eq) and potassium carbonate (2.0 eq) were suspended in a mixed solution of 300 ml of THF and 100 ml of distilled water, and heated to 80 °C in a nitrogen atmosphere for 24 hours. After the mixture was cooled to room temperature, 300 ml of distilled water was added thereto, the organic layer was extracted with ethyl acetate, and the extracted organic layer was washed with an aqueous saturated sodium chloride solution and dried over magnesium sulfate. The resulting product was purified by column chromatography (dichloromethane / hexane (volume ratio 1:99)) to obtain Intermediate I-17-1 (yield: 81%).
[0896] Synthesis of Intermediate I-17-2
[0897]
[0898] Intermediate I-17-1 (1.0 eq), 3,5-di-tert-butylphenylboronic acid (1.0 eq), tetrakis(triphenylphosphine)palladium(0) (0.020 eq), and potassium carbonate (2.0 eq) were suspended in a mixed solution of 300 ml of THF and 100 ml of distilled water and heated to 80 °C for 24 hours under a nitrogen atmosphere. After the mixture was cooled to room temperature, 250 ml of distilled water was added thereto, the organic layer was extracted with ethyl acetate, and the extracted organic layer was washed with an aqueous saturated sodium chloride solution and dried over magnesium sulfate. The resulting product was purified by column chromatography (dichloromethane / hexane (volume ratio 1:99)) to obtain Intermediate I-17-2 (yield: 89%).
[0899] Synthesis of Intermediate I-17-3
[0900]
[0901] Intermediate I-17-2 (1.0 eq), 1-bromo-2-nitrobenzene (1.1 eq), Pd2(dba)3 (0.020 eq), SPhos (0.040 eq), and sodium tert-butoxide (1.6 eq) were suspended in toluene solvent and heated to 120 °C for 12 hours under a nitrogen atmosphere. After the mixture was cooled to room temperature, 300 ml of distilled water was added thereto, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with an aqueous saturated sodium chloride solution and dried over magnesium sulfate. The resulting product was purified by column chromatography (ethyl acetate / hexane (volume ratio 5:95)) to obtain Intermediate I-17-3 (yield: 78%).
[0902] Synthesis of Intermediate I-17-4
[0903]
[0904] Intermediate I-17-3 (1.0 eq) was dissolved in 300 ml of ethanol, and 3.2 ml of 37% hydrochloric acid aqueous solution by mass fraction was added dropwise thereto. Tin (1.0 eq) was added to the reaction mixture, and the mixture was stirred at 80 °C for 10 hours by raising the temperature. When the reaction was completed, the reaction product was cooled to room temperature and neutralized with 1 N sodium hydroxide solution. The organic layer was extracted with dichloromethane and distilled water, and the extracted organic layer was dried over magnesium sulfate to obtain Intermediate I-17-4 (yield: 75%). The obtained Intermediate I-17-4 was used in the next reaction without further purification.
[0905] Synthesis of Intermediate I-17-5
[0906]
[0907] 9-(4-(tert-Butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-D4-2-ol (1.0 eq), 4-bromo-2-fluoro-1-methylbenzene (1.1 eq) and potassium phosphate (2.0 eq) were suspended in 100 ml of dimethylformamide and heated at 160 °C for 8 hours under a nitrogen atmosphere. After cooling the mixture to room temperature, the solvent was removed by drying under reduced pressure, and the organic layer was extracted with ethyl acetate and water, and the extracted organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The resulting product was purified by column chromatography (ethyl acetate / hexane (volume ratio 10:90)) to obtain Intermediate I-17-5 (yield: 76%).
[0908] Synthesis of Intermediate I-17-6
[0909]
[0910] Intermediate I-17-4 (1.0 eq), Intermediate I-17-5 (1.1 eq), Pd2(dba)3 (0.050 eq), SPhos (0.075 eq) and sodium tert-butoxide (2.0 eq) were suspended in 100 ml of toluene and heated at 110 °C for 4 hours under a nitrogen atmosphere. After cooling the mixture to room temperature, the organic layer was extracted with ethyl acetate and water, and the extracted organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The resulting product was purified by column chromatography (ethyl acetate / hexane (volume ratio 10:90)) to obtain Intermediate I-17-6 (yield: 59%).
[0911] Synthesis of Intermediate I-17-7
[0912]
[0913] Intermediate I-17-6 (1.0 eq) was dissolved in 40 ml of triethyl orthoformate (50 eq), and 0.98 ml of 12 N hydrochloric acid (1.2 eq) was added dropwise thereto. The reaction mixture was heated to 80 °C and stirred for 12 hours. When the reaction was completed, the solvent was removed therefrom under reduced pressure, and the organic layer was extracted with ethyl acetate and distilled water. The organic layer was dried over magnesium sulfate, and the resulting product was purified by column chromatography (methanol / dichloromethane (volume ratio 5:95)) to obtain Intermediate I-17-7 (yield: 91%).
[0914] Synthesis of Compound BD17
[0915]
[0916] Intermediate I-17-7 (1.00 eq), sodium acetate (3.00 eq), and Pt(COD)Cl2 (1.05 eq) were suspended in 85 ml of 1,4-dioxane and stirred at 120 °C for 12 h by raising the temperature. When the reaction was completed, the solvent was removed therefrom under reduced pressure, and the organic layer was extracted with ethyl acetate and distilled water. The resultant was dried over magnesium sulfate and purified by column chromatography (dichloromethane / hexane (volume ratio 50:50)) to obtain Compound BD17 (yield: 39%).
[0917] Synthesis Example 4 (Synthesis of Compound BD18)
[0918] Compound BD18 (yield: 45%) was obtained in substantially the same manner as in Synthesis Example 3, except that 9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-2-ol was used instead of 9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-D4-2-ol in the synthesis of Intermediate I-17-5 in Synthesis Example 3.
[0919] Synthesis Example 5 (Synthesis of Compound BD23)
[0920] Synthesis of Intermediate I-23-1
[0921]
[0922] Compound 23-a (1.0 eq), B2Pin2 (1.2 eq), Pd(dppf)Cl2 (0.05 eq), and KOAc (2.0 eq) were suspended in 0.2 M dioxane and heated at 120 °C for 12 h in an N2 atmosphere. After the mixture was cooled to room temperature (r.t.), distilled water was added thereto, the organic layer was extracted with ethyl acetate, and the extracted organic layer was washed with an aqueous saturated sodium chloride solution and dried over magnesium sulfate. The resultant was purified by column chromatography (dichloromethane / hexane (volume ratio 1:99)) to obtain Intermediate I-23-1 (yield: 76%).
[0923] Synthesis of Intermediate I-23-2
[0924]
[0925] Suspend 12 g of intermediate I-23-1 (1.0 eq), 3-bromo-3’,5’-di-tert-butyl-[1,1’-biphenyl]-2-amine (1.1 eq), tetrakis(triphenylphosphine)palladium(0) (0.020 eq) and potassium carbonate (2.0 eq) in a mixed solution of 300 ml of THF and 100 ml of distilled water, and heat to 80 °C in a nitrogen atmosphere for 24 h. After cooling the mixture to room temperature, add 300 ml of distilled water thereto, extract the organic layer by using ethyl acetate, and wash the extracted organic layer with an aqueous solution of saturated sodium chloride and dry with magnesium sulfate. Purify the resultant thus obtained by column chromatography (dichloromethane / hexane (volume ratio 1:99)) to obtain intermediate I-23-2 (yield: 81%).
[0926] Synthesis of intermediate I-23-3
[0927]
[0928] Suspend intermediate I-23-2 (1.0 eq), 1-bromo-2-nitrobenzene (1.1 eq), Pd2(dba)3 (0.050 eq), SPhos (0.075 eq) and sodium tert-butoxide (2.0 eq) in 100 ml of toluene, and heat to 110 °C in a nitrogen atmosphere for 4 h. After cooling the mixture to room temperature, extract the organic layer by using ethyl acetate and water, and wash the extracted organic layer with an aqueous solution of saturated sodium chloride and dry with magnesium sulfate. Purify the resultant thus obtained by column chromatography (ethyl acetate / hexane (volume ratio 10:90)) to obtain intermediate I-23-3 (yield: 59%).
[0929] Synthesis of intermediate I-23-4
[0930]
[0931] Dissolve intermediate I-23-3 (1.0 eq) in 300 ml of ethanol, and dropwise add 3.2 ml of an aqueous solution of 37% hydrochloric acid by mass fraction thereto. Add tin (1.0 eq) to the reaction mixture, and stir at 80 °C for 10 h by raising the temperature. When the reaction is completed, cool the reaction result to room temperature and neutralize with 1 N sodium hydroxide solution, extract the organic layer by using dichloromethane and distilled water, and dry the extracted organic layer with magnesium sulfate to obtain intermediate I-23-4 (yield: 77%). Use the obtained intermediate I-23-4 in the next reaction without further purification.
[0932] Synthesis of intermediate I-23-5
[0933]
[0934] Intermediate I-23-4 (1.0 eq), Intermediate I-17-5 (1.1 eq), Pd2(dba)3 (0.050 eq), XPhos (0.075 eq) and sodium tert-butoxide (2.0 eq) were suspended in 100 ml of 1,4-dioxane and heated to 110 °C for 4 hours under a nitrogen atmosphere. After the mixture was cooled to room temperature, the organic layer was extracted using ethyl acetate and water, and the extracted organic layer was rinsed with an aqueous saturated sodium chloride solution and dried over magnesium sulfate. The resulting product was purified by column chromatography (ethyl acetate / hexane (volume ratio 10:90)) to obtain Intermediate I-23-5 (yield: 66%).
[0935] Synthesis of Intermediate I-23-6
[0936]
[0937] Intermediate I-23-5 (1.0 eq) was dissolved in 40 ml of triethyl orthoformate (50 eq), and 0.98 ml of 12 N hydrochloric acid (1.2 eq) was added dropwise thereto. The reaction mixture was heated to 80 °C and stirred for 12 hours. When the reaction was completed, the solvent was removed therefrom under reduced pressure, and the organic layer was extracted using ethyl acetate and distilled water. The organic layer was dried over magnesium sulfate, and the resulting product was purified by column chromatography (methanol / dichloromethane (volume ratio 5:95)) to obtain Intermediate I-23-6 (yield: 90%).
[0938] Synthesis of Compound BD23
[0939]
[0940] Intermediate I-23-6 (1.00 eq), 2,6-dimethylpyridine (3.00 eq) and potassium tetrachloroplatinate (K2PtCl4) (1.05 eq) were suspended in 85 ml of ODCB and stirred at 125 °C for 24 hours by raising the temperature. When the reaction was completed, the solvent was removed therefrom under reduced pressure, and the organic layer was extracted using ethyl acetate and distilled water. The resulting product was dried over magnesium sulfate and purified by column chromatography (dichloromethane / hexane (volume ratio 50:50)) to obtain Compound BD23 (yield: 45%).
[0941] Synthesis Example 6 (Synthesis of Compound BD24)
[0942] Synthesis of Intermediate I-24-1
[0943]
[0944] Compound 24-a (1.0 eq), B2Pin2 (1.2 eq), Pd(dppf)Cl2 (0.05 eq) and KOAc (2.0 eq) were suspended in 0.2 M dioxane and heated at 120 °C for 12 h under N2 atmosphere. After cooling the mixture to room temperature (r.t.), distilled water was added thereto, the organic layer was extracted with ethyl acetate, and the extracted organic layer was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The resulting product was purified by column chromatography (dichloromethane / hexane (volume ratio 1:99)) to obtain Intermediate I-24-1 (yield: 79%).
[0945] Synthesis of Intermediate I-24-2
[0946]
[0947] 14 g of Intermediate I-24-1 (1.0 eq), 2,6-dibromo-4-(tert-butyl)-N-(2-nitrophenyl)aniline (1.1 eq), chlorophenylallyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]palladium(II) (CX31) (0.020 eq) and sodium carbonate (2.0 eq) were suspended in a dioxane solution and heated at 110 °C for 24 h under nitrogen atmosphere. After cooling the mixture to room temperature, 300 ml of distilled water was added thereto, the organic layer was extracted with ethyl acetate, and the extracted organic layer was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The resulting product was purified by column chromatography (dichloromethane / hexane (volume ratio 1:99)) to obtain Intermediate I-24-2 (yield: 74%).
[0948] Synthesis of Intermediate I-24-3
[0949]
[0950] Intermediate I-24-2 (1.0 eq) was dissolved in 300 ml of ethanol, and 3.2 ml of 37% aqueous hydrochloric acid solution by mass fraction was added dropwise thereto. Tin (1.0 eq) was added to the reaction mixture, and the mixture was stirred at 80 °C for 10 h by raising the temperature. When the reaction was completed, the reaction product was cooled to room temperature and neutralized with 1 N sodium hydroxide solution. The organic layer was extracted with dichloromethane and distilled water, and the extracted organic layer was dried over magnesium sulfate to obtain Intermediate I-24-3 (yield: 71%). The obtained Intermediate I-24-3 was used for the next reaction without further purification.
[0951] Synthesis of Intermediate I-24-4
[0952]
[0953] Intermediate I-24-3 (1.0 eq), Intermediate I-17-5 (1.1 eq), Pd2(dba)3 (0.050 eq), SPhos (0.075 eq), and sodium tert-butoxide (2.0 eq) were suspended in 100 ml of toluene and heated to 110 °C for 4 hours under a nitrogen atmosphere. After cooling the mixture to room temperature, the organic layer was extracted using ethyl acetate and water, and the extracted organic layer was washed with an aqueous saturated sodium chloride solution and dried over magnesium sulfate. The resulting product was purified by column chromatography (ethyl acetate / hexane (volume ratio 10:90)) to obtain Intermediate I-24-4 (yield: 70%).
[0954] Synthesis of Intermediate I-24-5
[0955]
[0956] Intermediate I-24-4 (1.0 eq) was dissolved in 40 ml of triethyl orthoformate (50 eq), and 0.98 ml of 12 N hydrochloric acid (1.2 eq) was added dropwise thereto. The reaction mixture was heated to 80 °C and stirred for 12 hours. When the reaction was completed, the solvent was removed therefrom under reduced pressure, and the organic layer was extracted using ethyl acetate and distilled water. The organic layer was dried over magnesium sulfate, and the resulting product was purified by column chromatography (methanol / dichloromethane (volume ratio 5:95)) to obtain Intermediate I-24-5 (yield: 81%).
[0957] Synthesis of Compound BD24
[0958]
[0959] Intermediate I-24-5 (1.00 eq), 2,6-dimethylpyridine (3.00 eq), and potassium tetrachloroplatinate (K2PtCl4) (1.05 eq) were suspended in 85 ml of ODCB and stirred at 125 °C for 24 hours by raising the temperature. When the reaction was completed, the solvent was removed therefrom under reduced pressure, and the organic layer was extracted using ethyl acetate and distilled water. The resulting product was dried over magnesium sulfate and purified by column chromatography (dichloromethane / hexane (volume ratio 50:50)) to obtain Compound BD24 (yield: 47%).
[0960] Those skilled in the art can easily identify the synthesis methods of compounds other than the compounds of Synthesis Examples 1 to 6 by referring to the synthetic routes and raw materials.
[0961] Comparative Example 1
[0962] As the anode, formed thereon The ITO glass substrate (a product of Corning Inc.) was cut into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, rinsed by ultraviolet irradiation and ozone exposure for 30 minutes, and then mounted on a vacuum deposition apparatus.
[0963] 2-TNATA was vacuum deposited on the anode to form a hole injection layer with a thickness of 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 transport layer with a thickness of Compound CE1, compound ETH2 (second compound), compound HTH42 (third compound), and compound DFD30 (fourth compound) were vacuum deposited on the hole transport layer to form an emission layer with a thickness of
[0964] In this regard, based on the total amount of the emission layer (100 wt%), the amount of compound CE1 was 13 wt%, based on the total amount of the emission layer (100 wt%), the amount of compound DFD30 was 1.5 wt%, and the weight ratio of compound ETH2 to compound HTH42 was adjusted to 4:6. The organometallic compounds used to form the emission layer are shown in Table 1. Compound ETH34 was vacuum deposited on the emission layer to form a hole blocking layer with a thickness of
[0965] ET46 and Liq were vacuum deposited on the hole blocking layer at a weight ratio of 4:6 to form an electron transport layer with a thickness of Yb was vacuum deposited on the electron transport layer to form an electron injection layer with a thickness of and Mg was vacuum deposited thereon to form a cathode with a thickness of thereby completing the fabrication of the light-emitting device. Comparative Examples 2 to 8
[0966]
[0967] The light-emitting device was fabricated in substantially the same manner as in Comparative Example 1, except that the organometallic compounds shown in Table 1 were used instead of compound CE1 when forming the emission layer.
[0968] Table 1
[0969] Table 1
[0970] Number Organometallic compound Comparative Example 1 CE1 Comparative Example 2 CE2 Comparative Example 3 CE3 Comparative Example 4 CE4 Comparative Example 5 CE5 Comparative Example 6 CE6 Comparative Example 7 CE7 Comparative Example 8 CE8
[0971]
[0972] Ar5 in compound CE2 is composed of The group represented, and the * in Ar5 indicates the bonding site to the adjacent atom.
[0973] Examples 1 to 19
[0974] The light-emitting device was fabricated in substantially the same manner as in Comparative Example 1, except that the organometallic compound shown in Table 2 was used instead of Compound CE1 when forming the emission layer.
[0975] Table 2
[0976] Number Organometallic compound Example 1 BD1 Example 2 BD3 Example 3 BD5 Example 4 BD7 Example 5 BD9 Example 6 BD12 Example 7 BD15 Example 8 BD16 Example 9 BD17 Example 10 BD18 Example 11 BD19 Example 12 BD20 Example 13 BD21 Example 14 BD22 Example 15 BD23 Example 16 BD24 Example 17 BD25 Example 18 BD26 Example 19 BD27
[0977]
[0978]
[0979]
[0980] In compounds BD1, BD5, and BD25 to BD27, Ar1 is the group represented by In compounds BD3 and BD7, Ar2 is the group represented by In compound BD9, Ar3 is the group represented by In compounds BD12, BD15, and BD16, Ar4 is the group represented by and the * in Ar1 to Ar4 indicates the bonding site to the adjacent atom.
[0981] Evaluation Example 1
[0982] The capacitance was measured by applying a voltage of -4V to 6V at 500 Hz to the light-emitting devices fabricated in Comparative Examples 1 to 8 and Examples 1 to 19 using the Alpha-A high-performance frequency analyzer equipment of Novocontrol Technologies, and the charge amount was calculated using Equation 1:
[0983] [Equation 1]
[0984]
[0985] In Equation 1,
[0986] Q refers to the charge amount,
[0987] C refers to the capacitance,
[0988] V1 is set to -2V,
[0989] V2 is the voltage corresponding to the maximum value of the capacitance (C max ) and
[0990] dV is the measurement interval of the voltage and is set to 0.1 V.
[0991] In Table 3, the maximum value of the capacitance (C max ) and the calculated charge amount (Q) measured for each light-emitting device are shown. The maximum value of the capacitance (C max ) and each of the charge amounts (Q) are the average values of 25 evaluations for each light-emitting device. The maximum value of the capacitance (100%) relative to Comparative Example 1 represents the relative maximum value of the capacitance (relative C max ), and the charge amount (100%) relative to Comparative Example 1 represents the relative charge amount (relative Q).
[0992] Table 3
[0993]
[0994] It was confirmed from Table 3 that the light-emitting devices according to Embodiments 1 to 19 exhibited both a reduced maximum value of capacitance and a reduced charge amount as compared with the light-emitting devices according to Comparative Examples 1 to 8.
[0995] Since the organometallic compound represented by Formula 1 satisfies both Condition A and Condition B, the injection of holes can be relatively slowed down. Therefore, the hump that may occur in the low voltage region can be shifted to the high voltage region, and the maximum value of the capacitance can be reduced. In an embodiment, the maximum value of the capacitance and the charge amount of the light-emitting device including the organometallic compound represented by Formula 1 can be reduced. As a result, the possibility of RC delay in the electronic device including the light-emitting device can be reduced, thereby improving the display quality.
[0996] Embodiments have been disclosed herein, and although terms are employed, they are used and interpreted only in a general and descriptive sense and not for purposes of limitation. In some cases, as will be apparent to those of ordinary skill in the art, features, characteristics, and / or elements described in connection with an embodiment may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments unless otherwise specifically indicated. Accordingly, those of ordinary skill in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of the present disclosure.
Claims
1. A light-emitting device, comprising: A first electrode; A second electrode facing the first electrode; And A laminate between the first electrode and the second electrode and including an emission layer, wherein The laminate includes an organometallic compound represented by Formula 1 and satisfying Condition A and Condition B: Formula 1 Condition A In Formula 1, the part represented by is the part represented by Formula 1-1 or Formula 1-2; Formula 1-1 Formula 1-2 Condition B At least one of a2 number of R2 is independently deuterium, methyl, ethyl, propyl, methyl substituted with at least one deuterium, ethyl substituted with at least one deuterium, or propyl substituted with at least one deuterium, Wherein in Formula 1, Formula 1-1, and Formula 1-2, M is Pt, Pd, Au, Ag, Ni, or Cu, X1 to X4 are each independently C or N, T1 is a single bond, O, N(Z1), or C(Z1)(Z2), Ring CY1 to ring CY4 and ring CY 11 to ring CY 16 each independently represents a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group, Z1, Z2, R1 to R4 and R 1a to R 1f each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkyl, 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 60 carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), Multiple Rs 1a Optionally bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group, 10a 60 Multiple Rs 1b Optionally bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, Multiple Rs 1c Optionally bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, Multiple Rs 1d Optionally bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group, 10a 60 Multiple Rs 1e Optionally bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group, 10a 60 Multiple Rs 1f Optionally bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, a1 to a4 and b1 to b6 are each independently an integer selected from 0 to 20, R 10a is as follows: Deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro; Each unsubstituted or substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; Each unsubstituted or substituted C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group or C2-C 60 heteroaralkyl group: deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro; or Each unsubstituted or substituted C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl group or C2-C 60 heteroaralkyl group: deuterium, -F, cyano group, C1-C 60 alkyl group, C1-C 60 alkoxy group, phenyl group, biphenyl group or any combination thereof, * indicates the bonding site to M in Formula 1, and *’ indicates the bonding site to the ring CY2 in Formula 1.
2. The light-emitting device according to claim 1, further comprising: comprising at least one second compound having a nitrogen-containing C1-C 60 heterocyclic group lacking π electrons, a third compound comprising a group represented by Formula 3, a fourth compound which is a delayed fluorescence compound, or any combination thereof, wherein The organometallic compound, the second compound, the third compound, and the fourth compound are different from each other: Formula 3 Wherein in Formula 3, Ring CY 71 and Ring CY 72 each independently is a π - electron - rich C3 - C 60 cyclic group or pyridyl group, X 71 is: a single bond; or a linking group comprising O, S, N, B, C, Si or any combination thereof, and * indicates the bonding site to an atom included in the remaining part of the third compound other than Formula 3.
3. The light-emitting device according to claim 2, wherein The second compound includes pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or any combination thereof, and The fourth compound is a compound including at least one cyclic group, and the cyclic group includes B and N as ring-forming atoms.
4. The light-emitting device according to claim 2, wherein the emission layer includes: The organometallic compound; And The second compound, the third compound, the fourth compound, or any combination thereof, and The emission layer emits blue light.
5. An electronic device, comprising: The light-emitting device according to any one of claims 1 to 4; And A thin-film transistor electrically connected to the light-emitting device.
6. An electronic apparatus, comprising the light-emitting device according to any one of claims 1 to 4, wherein The electronic apparatus is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet computer, a phablet, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional display, a virtual reality display, an augmented reality display, a vehicle, a video wall including a plurality of displays spliced together, a theater screen, a stadium screen, a light therapy device, or a signboard.
7. An organometallic compound represented by Formula 1 and satisfying Condition A and Condition B: Formula 1 Condition A In Formula 1, the part represented by is the part represented by Formula 1-1 or Formula 1-2; Formula 1-1 Formula 1-2 Condition B At least one of R2 with a quantity of a2 is each independently deuterium, methyl, ethyl, propyl, methyl substituted with at least one deuterium, ethyl substituted with at least one deuterium, or propyl substituted with at least one deuterium, wherein in Formula 1, Formula 1-1, and Formula 1-2, M is Pt, Pd, Au, Ag, Ni, or Cu, X1 to X4 are each independently C or N, T1 is a single bond, O, N(Z1), or C(Z1)(Z2), Ring CY1 to Ring CY4 and Ring CY 11 to Ring CY 16 are each independently a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group, Z1, Z2, R1 to R4 and R 1a to R 1f each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkyl, 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 60 carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), Multiple Rs 1a Optionally bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group, 10a 60 Multiple Rs 1b Optionally bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, Multiple Rs 1c Optionally bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, Multiple Rs 1d Optionally bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group, 10a 60 Multiple Rs 1e Optionally bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group, 10a 60 Multiple Rs 1f Optionally bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, a1 to a4 and b1 to b6 are each independently an integer selected from 0 to 20, R 10a is: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro; Each unsubstituted or substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; Each unsubstituted or substituted C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group or C2-C 60 heteroaralkyl group: deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 Each independently is: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro; or Each unsubstituted or substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl or C2-C 60 heteroaralkyl: deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl or any combination thereof, * indicates the bonding site to M in Formula 1, and *’ indicates the bonding site to ring CY2 in Formula 1.
8. The organometallic compound according to claim 7, wherein in Formula 1, X1 is the carbon atom of the carbene moiety.
9. The organometallic compound according to claim 7, wherein in Formula 1, ring CY1 is a nitrogen-containing C1-C 60 heterocyclic group.
10. The organometallic compound according to claim 7, wherein The ring CY in Formula 1-1 11 to the ring CY 13 are identical to each other, and Ring CY in Formula 1-2 14 to Ring CY 16 are identical to each other.
11. The organometallic compound according to claim 7, wherein at least one of Condition 1 to Condition 3 is satisfied: Condition 1 In Formula 1-1, a plurality of Rs 1a are bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group; Condition 2 In Formula 1-1, at least one R 1b is a tert-butyl group; and Condition 3 In Formula 1-1, a plurality of Rs 1c are bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group.
12. The organometallic compound according to claim 7, wherein in Formula 1-2, the ring formed by CY1-CY 14 -CY 15 -CY 16 surrounding is a 9-membered ring.
13. The organometallic compound according to claim 7, wherein in Formula 1, the moiety represented by is a moiety represented by one of Formulae 1A to 1C: Formula 1A Formula 1B Formula 1C wherein in Formula 1A, Formula 1B and Formula 1C, X 11 is N or C(R 11 ), X 12 is N or C(R 12 ), X 13 is N or C(R 13 ), X 14 is N or C(R 14 ), X 15 is N or C(R 15 ) X 16 is N or C(R 16 ), X 17 is N or C(R 17 ), X 18 is N or C(R 18 ) X 19 is N or C(R 19 ), X 11d is N or C(R 11d ) X 12d is N or C(R 12d ), X 13d is N or C(R 13d ), X 14d is N or C(R 14d ) X 11e is N or C(R 11e ) X 12e is N or C(R 12e ) X 13e is N or C(R 13e ) X 14e is N or C(R 14e ), X 11f is N or C(R 11f ), X 12f is N or C(R 12f ), X 13f is N or C(R 13f ) X 14f is N or C(R 14f ) R 11 to R 16 each independently is the same as defined by reference R1 in Formula 1, R 17 to R 19 each independently corresponds to the reference R in Formula 1-1 1b and is defined to be the same R 11d to R 14d each independently corresponds to the reference R in Formula 1-2 1d and is defined to be the same R 11e to R 14e Each independently corresponds to the reference R in Formula 1-2 1e as defined, R 11f to R 14f Each independently corresponds to the reference R in Formula 1-2 1f as defined, and b1 and b3 are each independently an integer selected from 0 to 20.
14. The organometallic compound according to claim 13, wherein in Formula 1A and Formula 1B, the moiety represented by is the moiety represented by Formula AS: Formula AS wherein in Formula AS, X 17 , X 18 and X 19 are each the same as defined in Formula 1A and Formula 1B, X 11a is N or C(R 11a ) X 12a is N or C(R 12a ), X 13a is N or C(R 13a ), X 14a is N or C(R 14a ) X 15a is N or C(R 15a ), X 11c is N or C(R 11c ) X 12c is N or C(R 12c ), X 13c is N or C(R 13c ) X 14c is N or C(R 14c ), X 15c is N or C(R 15c ) R 11a to R 15a each independently is the same as that defined by reference R in Formula 1-1 1a and is defined as follows R 11c to R 15c each independently corresponds to the reference R in Formula 1-1 1c and is defined in the same way R 11a and R 12a 、R 12a and R 13a 、R 13a and R 14a and R 14a and R 15a each optionally bond to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, R 11c and R 12c 、R 12c and R 13c 、R 13c and R 14c and R 14c and R 15c each optionally bond to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, and * indicates the bonding site to ring CY1 in Formula 1.
15. The organometallic compound according to claim 13, wherein in Formula 1C, X 13e is C(R 13e ), and R 13e is phenyl substituted by at least one of deuterium and tert-butyl; X 14f is C(R 14f ), and R 14f is a phenyl group substituted with at least one of deuterium and tert-butyl; or X 13e is C(R 13e ), X 14f is C(R 14f ), and R 13e and R 14f are each independently a phenyl group substituted with at least one of deuterium and tert-butyl.
16. The organometallic compound according to claim 7, wherein in Formula 1, the moiety represented by is the moiety represented by Formula 2-1: Formula 2-1 wherein in Formula 2-1, X 21 is N or C(R 21 ), X 22 is N or C(R 22 ), X 23 is N or C(R 23 ) X2 is the same as defined in Formula 1, R 21 to R 23 each independently is the same as defined by reference R2 in Formula 1, R 21 and R 22 each independently is deuterium, methyl, ethyl, propyl, methyl substituted with at least one deuterium, ethyl substituted with at least one deuterium or propyl substituted with at least one deuterium, * indicates the bonding site to M in Formula 1, *’ indicates the bonding site to ring CY1 in Formula 1, and *” indicates the bonding site to T1 in Formula 1.
17. The organometallic compound according to claim 7, wherein in Formula 1, ring CY3 is: a C2-C8 monocyclic group; or A C4-C polycyclic group in which two or three C2-C8 monocyclic groups are fused to each other 20 polycyclic group.
18. The organometallic compound according to claim 7, wherein in Formula 1, the moiety represented by is a moiety represented by one of Formula 3A to Formula 3F: Formula 3A Formula 3B Formula 3C Formula 3D Formula 3E Formula 3F wherein in Formula 3A to Formula 3F, X 31 is N or C(R 31 ), X 32 is N or C(R 32 ) X 33 is N or C(R 33 ), X 34 is N or C(R 34 ) X 35 is N or C(R 35 ), X 36 is N or C(R 36 ), X 37 is N or C(R 37 ), R 31 to R 37 each independently is the same as defined by reference R3 in Formula 1, * indicates the bonding site to M in Formula 1, *’ indicates the bonding site to T1 in Formula 1, and *” indicates the bonding site to ring CY4 in Formula 1.
19. The organometallic compound according to claim 7, wherein in Formula 1, the moiety represented by is the moiety represented by Formula 4-1: Formula 4-1 wherein in Formula 4-1, X 41 is N or C, X 42 is N or C(R 42 ), X 43 is N or C(R 43 ), X 44 is N or C(R 44 ), X 45 is N or C(R 45 ), X4 is the same as defined in Formula 1, R 42 to R 45 each independently is the same as defined by reference R4 in Formula 1, * indicates the bonding site to M in Formula 1, and *’ indicates the bonding site to ring CY3 in Formula 1.
20. The organometallic compound according to claim 7, wherein the organometallic compound is one of Compound BD1 to Compound BD27: Among compounds BD1 to BD16 and compounds BD25 to BD27, Ar1 is a group represented by Ar2 is a group represented by and Ar3 is a group represented by and Ar4 is a group represented by and * in Ar1 to Ar4 indicates the bonding site to the adjacent atom.
Citation Information
Patent Citations
Bonding method of wrapping paper for filter rod
KR1020240003124A