Light-emitting device including fused ring compound, electronic device and electronic equipment including light-emitting device, and fused ring compound
By introducing fused ring compounds into the light emitting device, optimizing the hole and electron transport zones, the shortcomings of the existing devices in terms of viewing angle, contrast and response speed are solved, and the photoelectric characteristics with higher performance are achieved.
Patent Information
- Application Number
- CN202411839183.6
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-01-18
- Filing Date
- 2024-12-13
- Publication Date
- 2025-07-18
AI Technical Summary
The existing light emitting devices have shortcomings in viewing angle, contrast, response time, brightness, driving voltage and response speed, and it is difficult to meet high-performance requirements.
Using a light emitting device structure including a fused ring compound, by providing a sandwich between the first electrode and the second electrode, the interlayer containing a fused ring compound is optimized to optimize the hole and electron transport region, and carrier recombination efficiency and light emission performance are improved.
The viewing angle, contrast and response speed of the light emitting device are improved, the driving voltage is reduced, and the color purity and life characteristics are enhanced.
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Figure CN120344085A_ABST
Abstract
Description
[0001] Cross - reference to related applications
[0002] This application claims priority and the benefit of Korean Patent Application No. 10 - 2024 - 0008281, filed on January 18, 2024, with the Korean Intellectual Property Office, the entire content of which is incorporated herein by reference. Technical field
[0003] Embodiments relate to a light - emitting device including a polycyclic compound, an electronic device and electronic apparatus including the light - emitting device, and the polycyclic compound. Background art
[0004] A light - emitting device is a self - emitting device having a wide viewing angle, high contrast ratio, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed.
[0005] In a light - emitting device, a first electrode may be disposed on a substrate, and a hole - transport region, an emission layer, an electron - transport region, and a second electrode may be sequentially disposed on the first electrode. Holes provided from the first electrode move through the hole - transport region toward the emission layer, and electrons provided from the second electrode move through the electron - transport region toward the emission layer. Charge carriers, such as holes and electrons, recombine in the emission layer to generate excitons. The excitons may transition from an excited state to a ground state, thereby generating light.
[0006] It should be understood that this background - art section is intended to provide, in part, 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 relevant art before the effective filing date of the corresponding subject matter disclosed herein. Summary of the invention
[0007] Embodiments include: a light - emitting device including a polycyclic compound, an electronic device and electronic apparatus including the light - emitting device, and the polycyclic compound.
[0008] Additional aspects will be set forth in part in the following description, 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:
[0010] a first electrode,
[0011] a second electrode facing the first electrode,
[0012] a sandwich structure between the first electrode and the second electrode and including an emission layer, and
[0013] a polycyclic compound represented by Formula 1:
[0014] [Formula 1]
[0015]
[0016] In Formula 1,
[0017] Ar0 may be a group represented by Formula 2,
[0018] [Formula 2]
[0019]
[0020] In Formula 1 and Formula 2,
[0021] CY1 to CY3 may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0022] W1 may be a single bond, O, S, N(R4), N(Ar1), C(R4)(R5) or Si(R4)(R5),
[0023] W2 may be a single bond, O, S, N(R6), N(Ar2), C(R6)(R7) or Si(R6)(R7),
[0024] a1 and a2 may each independently be 0 or 1,
[0025] When a1 is 0, *-(W1) a1 -' may not exist,
[0026] When a2 is 0, *-(W2) a2 -' may not exist,
[0027] The sum of a1 and a2 may be 1 or greater,
[0028] Ar1 and Ar2 may each independently be a group represented by Formula 2,
[0029] The * in Formula 2 indicates the binding site to the adjacent nitrogen atom,
[0030] R1 to R3 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, 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 10aSubstituted C3-C 60 carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 heterocyclic group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) or M(L1) n1 (L2) n2 ,
[0031] provided that at least one of R1 to R3 may each independently be M(L1) n1 (L2) n2 ,
[0032] M may be a transition metal,
[0033] L1 and L2 may each independently be a monodentate ligand, bidentate ligand, tridentate ligand, tetradentate ligand, pentadentate ligand or hexadentate ligand,
[0034] n1 may be an integer selected from 0 to 6,
[0035] n2 may be an integer selected from 0 to 6,
[0036] when n1 is 2 or greater, two or more L1s may be the same or different from each other,
[0037] when n2 is 2 or greater, two or more L2s may be the same or different from each other,
[0038] the sum of n1 and n2 may be 1 or greater,
[0039] b1 to b3 may each independently be an integer selected from 1 to 10,
[0040] b21 and b23 may each independently be an integer selected from 1 to 5,
[0041] b22 may be an integer selected from 1 to 3,
[0042] when b1 is 2 or greater, two or more R1s may be the same or different from each other,
[0043] when b2 is 2 or greater, two or more R2s may be the same or different from each other,
[0044] when b3 is 2 or greater, two or more R3s may be the same or different from each other,
[0045] when b21 is 2 or greater, two or more R 21 may be the same or different from each other,
[0046] When b22 is 2 or greater, two or more Rs 22 may be the same as or different from each other,
[0047] When b23 is 2 or greater, two or more Rs 23 may be the same as or different from each other,
[0048] Two or more of the plurality of R1s may be connected to each other through a first linking group or may combine with each other to form a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group,
[0049] Two or more of the plurality of R2s may be connected to each other through a first linking group or may combine with each other to form a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group,
[0050] Two or more of the plurality of R3s may be connected to each other through a first linking group or may combine with each other to form a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group,
[0051] The first linking group may be a single bond, a double bond, *-O-*, *-S-*, *-C(=O)-*, *-S(=O)-*, *-C(R8)(R9)-*, *-C(R8)=C(R9)-*, *-C(R8)=*, *-Si(R8)(R9)-*, *-B(R8)-*, *-N(R8)-*, *-P(R8)-*, a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group,
[0052] R4 to R9 and R 21 to R 23 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a 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 R 10a substituted C2-C 60 alkynyl group, an unsubstituted or at least one R 10a substituted C1-C 60 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 60a heterocyclic group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0053] R 10a may be:
[0054] deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, an amidino group, a hydrazino group or a hydrazono group;
[0055] each unsubstituted or substituted by the following C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group or C1-C 60 alkoxy group: deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro 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 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;
[0056] each unsubstituted or substituted by the following 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, a hydroxy group, a cyano group, a 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 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
[0057] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and
[0058] Q1 to Q3, Q 11 to Q 13 、Q 21 to Q 23 and Q 31 to Q 33 can each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy group; cyano group; nitro group; C1-C that is unsubstituted or substituted by deuterium, -F, cyano group, C1-C 60 alkyl group, C1-C 60 alkoxy group, phenyl group, biphenyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, triazinyl group or any combination thereof 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 or C1-C 60 heterocyclic group; C7-C 60 arylalkyl group; or C2-C 60 heteroarylalkyl group.
[0059] In an embodiment, the first electrode may be an anode; the second electrode may be a cathode; the interlayer may further include a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode; the hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof; and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
[0060] In an embodiment, the interlayer may include a polycyclic compound represented by Formula 1.
[0061] In an embodiment, the emission layer may include a polycyclic compound represented by Formula 1.
[0062] In an embodiment, the emission layer may include a host and a dopant, and the dopant may include a polycyclic compound represented by Formula 1.
[0063] According to an embodiment, the electronic device may include a light-emitting device.
[0064] In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touchscreen layer, a polarization layer, or any combination thereof.
[0065] According to an embodiment, the electronic apparatus may include a light-emitting device.
[0066] In an embodiment, the electronic apparatus 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 having a plurality of displays tiled together, a theater screen, a stadium screen, a light therapy device, or a sign.
[0067] According to an embodiment, the polycyclic compound may be represented by Formula 1, which is explained herein.
[0068] In an embodiment, the polycyclic compound represented by Formula 1 may include at least one deuterium.
[0069] In an embodiment, CY1 to CY3 may each independently be a cyclopentadienyl group, an adamantyl group, a norbornyl group, a phenyl group, a pentaphenylenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthylenyl group, a phenalenyl group, a phenanthryl group, an anthryl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a 1,2-benzophenanthryl group, a perylenyl group, a pentaphenyl group, a heptaphenylenyl group, a tetracenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, an indenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, an indenoanthracenyl group, an indenoanthryl group, a pyrrolyl group, a thienyl group, a furyl group, an indolyl group, a benzindolyl group, a naphthylindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthylisoindolyl group, a benzosilolyl group, a benzothienyl group, a benzofuryl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothienyl group, a dibenzofuryl group, an indacarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuryl group, a benzonaphthothienyl group, a benzonaphthosilolyl group, a benzofurodibenzofuryl group, a benzofurodibenzothienyl group, a benzothienodibenzothienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a benzothiazolyl group, a benzisothiazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a phenanthrolinyl group, a cinnolinyl group, a phthalazinyl group, a naphthyridinyl group, an imidazopyridyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an azacarbazolyl group, an azafuryl group, an azadibenzosilolyl group, an azadibenzothienyl group or an azadibenzofuryl group.
[0070] In an embodiment, the sum of a1 and a2 may be 1, W1 may be N(Ar1), and W2 may be N(Ar2).
[0071] In an embodiment, M may be platinum (Pt), palladium (Pd), cobalt (Co), gold (Au), iridium (Ir), rhenium (Re), nickel (Ni), silver (Ag) or copper (Cu).
[0072] In an embodiment, L1 may be a group represented by one of Formula 3A to Formula 3E; and L2 may be *1-F, *1-Cl, *1-Br, *1-I, *1-C(R 41 )(R 42 )(R 43 ), *1-O(R 41 ) or a group represented by one of Formula 4A to Formula 4F, where Formula 3A to Formula 3E and Formula 4A to Formula 4F are explained below.
[0073] In an embodiment, n1 can be 0 and n2 can be 2; n1 can be 1 and n2 can be 0; n1 can be 1 and n2 can be 1; n1 can be 1 and n2 can be 2; n1 can be 2 and n2 can be 0; or n1 can be 3 and n2 can be 0.
[0074] In an embodiment, the polycyclic compound represented by Formula 1 can be represented by one of Formula 1A-1 to Formula 1A-11, Formula 1B-1 to Formula 1B-3, and Formula 1C-1, which are explained below.
[0075] In an embodiment, at least one of R1 to R3 can each independently be deuterium, -F, cyano, tert-butyl, carbazolyl, or any combination thereof.
[0076] In an embodiment, R4 to R9 and R 21 to R 23 can each independently be:
[0077] hydrogen, deuterium, -F, or cyano;
[0078] unsubstituted or substituted C1-C 20 alkyl: deuterium, -F, cyano, or any combination thereof; or
[0079] each unsubstituted or substituted phenyl, naphthyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or azacarbazolyl: deuterium, -F, cyano, C1-C 20 alkyl, deuterated C1-C 20 alkyl, fluorinated C1-C 20 alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorene, dibenzosilolyl, or any combination thereof.
[0080] In an embodiment, the polycyclic compound represented by Formula 1 can be one of Compounds 1 to 40, which are explained below.
[0081] It should be understood that the above embodiments are described only in a general and explanatory sense and not for the purpose of limitation, and the present disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS
[0082] The accompanying drawings are included to provide a further understanding of the embodiments, and the accompanying drawings are incorporated into and constitute a part of this specification. The drawings illustrate embodiments of the present disclosure and their principles. By referring to the accompanying drawings and describing the embodiments of the present disclosure in detail, the above and other aspects and features of the present disclosure will become more apparent, wherein:
[0083] Figure 1 A schematic cross-sectional view of the structure of a light-emitting device according to an embodiment;
[0084] Figure 2 A schematic cross-sectional view of the structure of an electronic device according to an embodiment;
[0085] Figure 3 A schematic cross-sectional view of the structure of an electronic device according to another embodiment;
[0086] Figure 4 A schematic perspective view of an electronic device according to an embodiment;
[0087] Figure 5 A schematic perspective view of the exterior of a vehicle as an electronic device including a light-emitting device according to an embodiment; and
[0088] Figures 6A to 6C Each is a schematic view of the interior of a vehicle according to an embodiment. Detailed Embodiments
[0089] 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 present disclosure to those skilled in the art.
[0090] In the drawings, for ease of description and for clarity, the dimensions (e.g., thickness), ratios, and dimensions of elements may be enlarged. The same reference numerals and / or the same reference characters refer to the same elements throughout.
[0091] In the description, it will be understood that when an element (or region, layer, part, etc.) is referred to as being "on," "connected to," or "coupled to" another element (or region, layer, part, etc.), it may be directly on, connected to, or coupled to the other element (or region, layer, part, etc.), or there may be one or more intervening elements (or regions, layers, parts, etc.) therebetween. In a similar sense, when an element (or region, layer, part, etc.) is described as "covering" another element (or region, layer, part, etc.), it may directly cover the other element (or region, layer, part, etc.), or there may be one or more intervening elements (or regions, layers, parts, etc.) therebetween.
[0092] In the description, when an element is "directly on", "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 disposed without another element (such as an adhesive element) therebetween.
[0093] As used herein, the singular forms of the expressions such as "a", "an", and "the" are intended to also include the plural forms unless the context clearly indicates otherwise.
[0094] 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" can be understood to mean "A, B, or A and B". The terms "and" and "or" can be used in a conjunctive sense or a disjunctive sense and can be understood to be equivalent to "and / or".
[0095] 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.
[0096] 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.
[0097] For ease of description, the spatially relative terms such as "beneath", "below", "under", "above", or "over" 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, the spatially relative terms are 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 "beneath" or "below" another device may be positioned "above" the other device. Accordingly, the illustrative term "beneath" can include both a lower position and an upper position. The device may also be oriented in other directions, and thus the spatially relative terms may be differently interpreted depending on the orientation.
[0098] As used herein, the term "about" or "approximate" includes the stated value and means within an acceptable deviation range of the recited value as determined by a person of ordinary skill in the art, taking into account the measurements discussed and the errors associated with the measurements of the recited quantity (e.g., limitations of the measurement system). For example, "about" can mean within one or more standard deviations of the stated value, or within ±20%, ±10%, or ±5% of the stated value.
[0099] It should be understood that the terms "comprise", "comprising", "include", "including", "have", "having", "contains", and "containing", etc. are intended to indicate the presence of the specified features, integers, steps, operations, elements, components, or any combination thereof in the present disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or any combination thereof.
[0100] Unless otherwise defined or implied herein, all terms used (including technical and scientific terms) have the same meaning as commonly understood by a person 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 consistent with their meaning in the context of the relevant art and should not be interpreted in an ideal or overly formal sense unless clearly defined in the specification.
[0101] According to an embodiment, the light-emitting device may include: a first electrode; a second electrode facing the first electrode; a sandwich layer between the first electrode and the second electrode and including an emission layer; and a polycyclic compound represented by Formula 1:
[0102] [Formula 1]
[0103]
[0104] In Formula 1, Ar0 may be a group represented by Formula 2:
[0105] [Formula 2]
[0106]
[0107] In Formula 1 and Formula 2,
[0108] CY1 to CY3 may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0109] W1 can be a single bond, O, S, N(R4), N(Ar1), C(R4)(R5), or Si(R4)(R5),
[0110] W2 can be a single bond, O, S, N(R6), N(Ar2), C(R6)(R7), or Si(R6)(R7),
[0111] a1 and a2 can each independently be 0 or 1,
[0112] When a1 is 0, *-(W1) a1 -*' may not exist,
[0113] When a2 is 0, *-(W2) a2 -*' may not exist,
[0114] The sum of a1 and a2 can be 1 or greater,
[0115] Ar1 and Ar2 can each independently be a group represented by Formula 2,
[0116] The * in Formula 2 indicates the binding site to the adjacent nitrogen atom,
[0117] R1 to R3 can each independently be 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or M(L1) n1 (L2) n2 ,
[0118] Provided that at least one of R1 to R3 can each independently be M(L1) n1 (L2) n2 ,
[0119] M can be a transition metal,
[0120] L1 and L2 can each independently be a monodentate ligand, bidentate ligand, tridentate ligand, tetradentate ligand, pentadentate ligand or hexadentate ligand,
[0121] n1 can be an integer selected from 0 to 6,
[0122] n2 can be an integer selected from 0 to 6,
[0123] When n1 is 2 or greater, two or more L1s can be the same as or different from each other,
[0124] When n2 is 2 or greater, two or more L2s can be the same as or different from each other,
[0125] The sum of n1 and n2 can be 1 or greater,
[0126] b1 to b3 can each independently be an integer selected from 1 to 10,
[0127] b21 and b23 can each independently be an integer selected from 1 to 5,
[0128] b22 can be an integer selected from 1 to 3,
[0129] When b1 is 2 or greater, two or more R1s can be the same as or different from each other,
[0130] When b2 is 2 or greater, two or more R2s can be the same as or different from each other,
[0131] When b3 is 2 or greater, two or more R3s can be the same as or different from each other,
[0132] When b21 is 2 or greater, two or more Rs 21 can be the same as or different from each other,
[0133] When b22 is 2 or greater, two or more Rs 22 can be the same as or different from each other,
[0134] When b23 is 2 or greater, two or more Rs 23 can be the same as or different from each other,
[0135] Two or more of the plurality of R1s can be connected to each other through a first linking group or can combine with each other to form a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group,
[0136] Two or more of the plurality of R2s can be connected to each other through a first linking group or can combine with each other to form a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group,
[0137] Two or more of the plurality of R3s may be connected to each other through a first linking group or may combine with each other to form a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group,
[0138] The first linking group may be a single bond, a double bond, *-O-*, *-S-*, *-C(=O)-*, *-S(=O)-*, *-C(R8)(R9)-*, *-C(R8)=C(R9)-*, *-C(R8)=*, *-Si(R8)(R9)-*, *-B(R8)-*, *-N(R8)-*, *-P(R8)-*, a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group,
[0139] R4 to R9 and R 21 to R 23 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a 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 R 10a substituted C2-C 60 alkynyl group, an unsubstituted or at least one R 10a substituted C1-C 60 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0140] R 10a may be:
[0141] deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group or a hydrazono group;
[0142] each unsubstituted or substituted by the following C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group or a C1-C 60Alkoxy: 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;
[0143] Each unsubstituted or substituted C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 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 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or
[0144] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and
[0145] Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 can each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group or C1-C 60 heterocyclic group; C7-C 60 aralkyl; or C2-C 60 heteroaralkyl.
[0146] In an embodiment, the fused-ring compound represented by Formula 1 may include at least one deuterium.
[0147] In an embodiment, CY1 to CY3 may each independently be each 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, coronenyl, ovalenyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl, indenanthryl, pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthylindolyl, isoindolyl, benzisoindolyl, naphthylisoindolyl, benzosilolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuryl, indacarbazolyl, 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 or azadibenzofuryl.
[0148] In an embodiment, CY1 to CY3 may each independently be phenyl, pentaphenylenyl, naphthyl, azulenyl, indacenyl, acenaphthylenyl, phenalenyl, phenanthryl, anthryl, pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzosilolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuryl, indacarbazolyl, 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 or azadibenzofuryl.
[0149] In an embodiment, in Formula 1, a1 may be 1 and a2 may be 0; or a1 may be 0 and a2 may be 1.
[0150] In an embodiment, in Formula 1, the sum of a1 and a2 may be 1, W1 may be N(Ar1), and W2 may be N(Ar2).
[0151] In an embodiment, Ar0 and Ar1 may be the same as each other; or Ar0 and Ar2 may be the same as each other.
[0152] In an embodiment, M may be platinum (Pt), palladium (Pd), cobalt (Co), gold (Au), iridium (Ir), rhenium (Re), nickel (Ni), silver (Ag) or copper (Cu).
[0153] In an embodiment, L1 may be a group represented by one of Formulae 3A to 3E; and L2 may be *1-F, *1-Cl, *1-Br, *1-I, *1-C(R 41 )(R 42 )(R 43 ), *1-O(R 41 ) or a group represented by one of Formulae 4A to 4F:
[0154]
[0155]
[0156] In Formulas 3A to 3E and Formulas 4A to 4F,
[0157] *1, *2, *3, and *4 each indicate a binding site to M,
[0158] Y 31 to Y 34 may each independently be a single bond, *-O-*', *-S-*', *-C(R 35 )(R 36 ))-*', *-Si(R 35 )(R 36 ))-*', *-B(R 35 ))-*', *-N(R 35 ))-*' or *-P(R 35 ))-*',
[0159] Z 41 and Z 42 may each independently be a single bond, *-O-*', *-S-*', *-B(R 44 ))-*', *-N(R 44 ))-*' or *-P(R 44 ))-*',
[0160] A 31 to A 34 and A 41 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,
[0161] a31 to a34 and d41 may each independently be an integer selected from 1 to 3,
[0162] T 31 to T 34 may each independently be a single bond, double bond, *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', *-C(R 37 )(R 38 ))-*', *-C(R 37 ))=C(R 38 ))-*', *-C(R 37 ))=*', *-Si(R 37 )(R 38 ))-*', *-B(R 37)-'、-N(R 37 )-' or -P(R 37 )-',
[0163] U 41 and U 42 can each independently be -O-', -S-', -C(=O)-', -S(=O)-', -C(R 45 )(R 46 )-', -C(R 45 )=C(R 46 )-', -C(R 45 )= ', -Si(R 45 )(R 46 )-', -B(R 45 )-', -N(R 45 )-', or -P(R 45 )-',
[0164] X can be C, P or As,
[0165] b31 to b34 can each independently be an integer selected from 0 to 10,
[0166] R 31 to R 38 and R 41 to R 46 can each independently be 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0167] R 10a can be:
[0168] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino or hydrazono;
[0169] C1-C, each unsubstituted or substituted by the following 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;
[0170] C3-C, each unsubstituted or substituted by the following 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 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21)(Q 22 )、 -B(Q 21 )(Q 22 )、 -C(=O)(Q 21 )、 -S(=O)2(Q 21 )、 -P(=O)(Q 21 )(Q 22 ) or any combination thereof; or
[0171] -Si(Q 31 )(Q 32 )(Q 33 )、 -N(Q 31 )(Q 32 )、 -B(Q 31 )(Q 32 )、 -P(Q 31 )(Q 32 )、 -C(=O)(Q 31 )、 -S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and
[0172] Q1 to Q3, Q 11 to Q 13 、 Q 21 to Q 23 and Q 31 to Q 33 can each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C that is unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof-substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group or C1-C 60 heterocyclic group; C7-C 60 aralkyl; or C2-C 60 heteroaralkyl.
[0173] In an embodiment, in Formula 1,
[0174] n1 can be 0, and n2 can be 2;
[0175] n1 can be 1, and n2 can be 0;
[0176] n1 can be 1, and n2 can be 1;
[0177] n1 can be 1, and n2 can be 2;
[0178] n1 can be 2, and n2 can be 0; or
[0179] n1 can be 3, and n2 can be 0.
[0180] In an embodiment, the condensed ring compound represented by Formula 1 can be represented by one of Formula 1A-1 to Formula 1A-11, Formula 1B-1 to Formula 1B-3, and Formula 1C-1:
[0181]
[0182]
[0183]
[0184]
[0185] In Formula 1A-1 to Formula 1A-11, Formula 1B-1 to Formula 1B-3, and Formula 1C-1,
[0186] Ar0, CY2, CY3, W2, a2, R2, R3, b2, and b3 can each be the same as those described herein,
[0187] M1 can be platinum (Pt), palladium (Pd), cobalt (Co), gold (Au), iridium (Ir), rhenium (Re), nickel (Ni), silver (Ag), or copper (Cu),
[0188] M2 can be gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
[0189] M3 can be iridium (Ir) or rhenium (Re),
[0190] X1 to X6 can each independently be C or N,
[0191] X 51 and X 52 can each independently be C, P, or As,
[0192] Y 51 to Y 56 can each independently be a single bond, *-O-*', *-S-*', *-C(R 57 )(R 58 ))-*', *-Si(R 57 )(R 58 )-*', *-B(R 57 )-*', *-N(R 57 )-*', or *-P(R 57)-*',
[0193] A 51 to A 53 、A 55 and A 56 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,
[0194] T 51 to T 54 may each independently be a single bond, a double bond, *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', *-C(R 59 )(R 60 ))-*', *-C(R 59 ))=C(R 60 ))-*', *-C(R 59 ))=*', *-Si(R 59 )(R 60 ))-*', *-B(R 59 ))-*', *-N(R 59 ))-*' or *-P(R 59 ))-*',
[0195] Z 51 to Z 54 may each independently be a single bond, *-O-*', *-S-*', *-B(R 61 ))-*', *-N(R 61 ))-*' or *-P(R 61 ))-*',
[0196] U 51 and U 52 may each independently be *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', *-C(R 62 )(R 63 ))-*', *-C(R 62 ))=C(R 63 ))-*', *-C(R 62 ))=*', *-Si(R 62 )(R 63 ))-*', *-B(R 62 ))-*', *-N(R 62 ))-*' or *-P(R 62 ))-*',
[0197] a51 to a54 can each independently be an integer selected from 1 to 3,
[0198] b51 to b53, b55 and b56 can each independently be an integer selected from 0 to 10,
[0199] d51 and d52 can each independently be an integer selected from 1 to 3, and
[0200] R 51 to R 63 can each independently be 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2).
[0201] In an embodiment, R 51 to R 63 can each independently be hydrogen, deuterium, -F, cyano, unsubstituted or substituted by at least one R 10a substituted C1-C 20 alkyl, 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.
[0202] In an embodiment, R 51 to R 63 can each independently be:
[0203] hydrogen, deuterium, -F or cyano;
[0204] methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl or 1,2-dimethylpropyl, each unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; or
[0205] phenyl, naphthyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, azadibenzofuranyl, azadibenzothiophenyl or azacarbazolyl, each unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl or phenyl.
[0206] In an embodiment, the polycyclic compound represented by Formula 1 may include at least one carbazolyl or at least one tert-butyl.
[0207] In an embodiment, at least one of R1 to R3 may each independently be deuterium, -F, cyano, tert-butyl, carbazolyl or any combination thereof.
[0208] In an embodiment, R4 to R9 and R 21 to R 23 may each independently be hydrogen, deuterium, -F, cyano, unsubstituted or substituted with at least one R 10a substituted C1-C 20 alkyl, unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclic group or unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclic group.
[0209] In an embodiment, R4 to R9 and R 21 to R 23 may each independently be:[[]]
[0210] hydrogen, deuterium, -F or cyano;
[0211] unsubstituted or substituted with the following C1-C 20 alkyl: deuterium, -F, cyano or any combination thereof; or
[0212] phenyl, naphthyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, azadibenzofuranyl, azadibenzothiophenyl or azacarbazolyl, each unsubstituted or substituted with: deuterium, -F, cyano, C1-C 20Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, dibenzosilolyl or any combination thereof.
[0213] In an embodiment, R4 to R9 and R 21 to R 23 can each independently be:
[0214] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;
[0215] Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl or 1,2-dimethylpropyl, each unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro; or
[0216] Phenyl, naphthyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, azadibenzofuranyl, azadibenzothiophenyl or azacarbazolyl, each unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl or phenyl.
[0217] In an embodiment, R4 to R9 and R 21 to R 23 can each independently be:
[0218] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano or C1-C 20 alkyl;
[0219] C1-C 20 alkyl substituted by: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, nitro, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl and pyrimidinyl, at least one of;
[0220] Each unsubstituted or substituted phenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, azadibenzofuranyl, azadibenzothiophenyl or azacarbazolyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, C1-C 20 alkyl, phenyl, biphenyl, C1-C 10 alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthrenyl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), and -B(Q 31 )(Q 32 ), at least one of; or
[0221] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2) or -B(Q1)(Q2), and
[0222] Q1 to Q3 and Q 31 to Q 33 may each independently be:
[0223] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H or -CD2CDH2; or
[0224] each unsubstituted or substituted n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl: deuterium, C1-C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl and at least one of triazinyl.
[0225] In an embodiment, R4 to R9 and R 21 to R 23 may each independently be:
[0226] hydrogen, deuterium, -F or cyano;
[0227] methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl or 1,2-dimethylpropyl, each unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; or
[0228] phenyl, naphthyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, azadibenzofuranyl, azadibenzothiophenyl or azacarbazolyl, each unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl or phenyl.
[0229] In an embodiment, the polycyclic compound represented by Formula 1 may be one of Compounds 1 to 40:
[0230]
[0231]
[0232] As a compound having the structure represented by Formula 1, the polycyclic compound may include a group represented by Formula 2 and an organometallic moiety represented by (M(L1) n1 (L2) n2 ). Accordingly, the polycyclic compound represented by Formula 1 can increase the reverse intersystem crossing (RISC) rate and τD through the heavy atom effect, reduce the density of triplet excitons, thereby suppressing material deterioration in the light-emitting device.
[0233] Accordingly, the polycyclic compound represented by Formula 1 can achieve improved color purity and lower driving voltage of the light-emitting device. In a light-emitting device including the polycyclic compound represented by Formula 1 according to an embodiment, energy can be easily transferred therein, thereby improving the lifetime characteristics.
[0234] By referring to the following Synthesis Examples and / or Examples, the synthesis method of the polycyclic compound represented by Formula 1 can be recognized by those of ordinary skill in the art.
[0235] At least one of the polycyclic compounds represented by Formula 1 can be used in a light-emitting device (e.g., an organic light-emitting device). Accordingly, on the other hand, there is provided a light-emitting device, which may include: a first electrode; a second electrode facing the first electrode; a laminate between the first electrode and the second electrode and including an emission layer; and a polycyclic compound represented by Formula 1.
[0236] In an embodiment,
[0237] The first electrode of the light-emitting device can be an anode,
[0238] The second electrode of the light-emitting device can be a cathode, and
[0239] The laminate may further include a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode,
[0240] The hole transport region can include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and
[0241] The electron transport region can include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
[0242] In an embodiment, the laminate may include a polycyclic compound represented by Formula 1.
[0243] In an embodiment, the emission layer may include a polycyclic compound represented by Formula 1.
[0244] In an embodiment, the light-emitting device may further include a capping layer outside the second electrode, and the capping layer may include a polycyclic compound represented by Formula 1.
[0245] In an embodiment, the light-emitting device may further include:
[0246] A first capping layer outside the first electrode; and
[0247] A second capping layer outside the second electrode,
[0248] wherein the polycyclic compound represented by Formula 1 may be included in the first capping layer or the second capping layer.
[0249] In an embodiment, the emission layer may include a host and a dopant, and the dopant may include a polycyclic compound represented by Formula 1.
[0250] In an embodiment, the emission layer may emit blue light.
[0251] In an embodiment, the dopant may be a phosphorescent dopant or a delayed fluorescence dopant.
[0252] In an embodiment, the host may include a first host including at least one electron-donating group and a second host including at least one electron-withdrawing group.
[0253] In an embodiment, the emissive layer may further include a sensitizer.
[0254] In an embodiment, the emissive layer may further include a delayed fluorescence material.
[0255] In an embodiment, the emissive layer may include a first host and a second host, wherein the first host may be a hole-transporting compound including at least one electron-donating group, and the second host may be an electron-transporting compound including at least one electron-withdrawing group.
[0256] In an embodiment, the emissive layer may further include a third compound, wherein the third compound may be a metal-containing compound.
[0257] In an embodiment, the third compound may be used as a sensitizer, such as a phosphorescent sensitizer.
[0258] In an embodiment, the third compound may not emit light.
[0259] In an embodiment, the emissive layer may further include at least one of an auxiliary dopant and a sensitizer.
[0260] In an embodiment, the auxiliary dopant and the sensitizer may each independently be an organometallic compound including platinum (Pt) and a tetradentate ligand chemically bonded to Pt, wherein the tetradentate ligand may include a carbene moiety chemically bonded to Pt. In an embodiment, the auxiliary dopant and / or the sensitizer may include a third compound.
[0261] In an embodiment, the first host and the second host may form an exciplex.
[0262] In the specification, the term "electron-donating group" may be any group having an electron-donating ability, and for example, may be a π-electron-rich C3-C 60 cyclic group or an amino group, but the embodiment is not limited thereto. The electron-donating group may be a cyclic group other than a π-electron-deficient nitrogen-containing C1-C 60 cyclic group.
[0263] In the specification, the term "electron-withdrawing group" may be any group having an electron-withdrawing ability, and for example, may be -F, -CFH2, -CF2H, -CF3, -CN, -NO2, a π-electron-deficient nitrogen-containing C1-C 60 cyclic group or any combination thereof. However, the embodiment is not limited thereto.
[0264] Regarding the light emission path in the light-emitting device according to the embodiment, the first host and the second host may form an exciplex (first step), energy may be transferred from the exciplex to the third compound (second step), and energy may be transferred from the third compound to the polycyclic compound represented by Formula 1 (third step).
[0265] In an embodiment, based on a total of 100 parts by weight of the emission layer, the amount of the third compound may be in the range of about 0 parts by weight to about 50 parts by weight.
[0266] In an embodiment, the first host may include at least one carbazole moiety, and the second host may include at least one azine moiety.
[0267] In an embodiment, the first host may be represented by Formula 301-1A or Formula 301-2A:
[0268] [Formula 301-1A]
[0269]
[0270] [Formula 301-2A]
[0271]
[0272] In Formula 301-1A and Formula 301-2A,
[0273] Ring A 301 to Ring A 304 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,
[0274] X 301 may be O, S, N[(L 304 ) xb4 -R 304a , C(R 304a )(R 304b ) or Si(R 304a )(R 304b ),
[0275] X 302 may be a single bond, O, S, N[(L 305 ) xb5 -R 305a , C(R 305a )(R 305b ) or Si(R 305a )(R 305b ),
[0276] X 303 may be a single bond, O, S, N[(L 306 ) xb6 -R 306a , C(R 306a )(R 306b ) or Si(R 306a )(R 306b ),
[0277] xb22 and xb23 can each independently be an integer selected from 0 to 10,
[0278] L 301 to L 307 can 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,
[0279] xb1 to xb7 can each independently be an integer selected from 0 to 5,
[0280] R 301 to R 303 , R 304a to R 306a , R 304b to R 306b and R 311 to R 314 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, 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 R 10a substituted C2-C 60 alkynyl group, an unsubstituted or at least one R 10a substituted C1-C 60 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, -C(Q 301 )(Q 302 )(Q 303 ), -Si(Q 301 )(Q 302 )(Q 303 ), -N(Q 301 )(Q302 ), -B(Q 301 )(Q 302 ), -C(=O)(Q 301 ), -S(=O)2(Q 301 ) or -P(=O)(Q 301 )(Q 302 ), and
[0281] Q 301 to Q 303 may each independently be the same as described with reference to Q1.
[0282] In an embodiment, the first subject may be one of Compounds HTH1 to HTH56, but the embodiment is not limited thereto:
[0283]
[0284]
[0285] In an embodiment, the second subject may be represented by Formula 302:
[0286] [Formula 302]
[0287]
[0288] In Formula 302,
[0289] X 321 may be C(R 321 )) or N,
[0290] X 322 may be C(R 322 )) or N,
[0291] X 323 may be C(R 323 )) or N,
[0292] X 321 to X 323 at least one of which may each be N,
[0293] L 324 to L 326 may each independently be a single bond, 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, *-C(Q 321 )(Q 322 ))-*', *-Si(Q 321 )(Q 322)-*', *-B(Q 321 )-*' or *-N(Q 321 )-*',
[0294] n324 to n326 can each independently be an integer selected from 1 to 5,
[0295] R 321 to R 326 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, 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, -C(Q 323 )(Q 324 )(Q 325 )、-Si(Q 323 )(Q 324 )(Q 325 )、-N(Q 323 )(Q 324 )、-B(Q 323 )(Q 324 )、-C(=O)(Q 323 )、-S(=O)2(Q 323 ) or -P(=O)(Q 323 )(Q 324 ),
[0296] Q 321 to Q 325 and R 321 to R 326 Two or more adjacent groups in 10a and R 30 can optionally be bonded to each other to form an unsubstituted or at least one R-substituted C5-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C2-C 30 heterocyclic group,
[0297] * and *' each indicate the binding site to the adjacent atom,
[0298] R 10a may be the same as those described herein, and
[0299] Q 321 to Q 325 may each independently be the same as those described with reference to Q1.
[0300] In an embodiment, the second subject may be one of Compounds ETH1 to ETH86, but the embodiment is not limited thereto:
[0301]
[0302]
[0303]
[0304] In an embodiment, the third compound may be represented by Formula 401A:
[0305] [Formula 401A]
[0306] M 401 (L 401 ) xc1 (L 402 ) xc2
[0307]
[0308]
[0309] In Formula 401A and Formulas 402A to 402D,
[0310] M 401 may be a first-row transition metal of the periodic table, a second-row transition metal of the periodic table, or a third-row transition metal of the periodic table,
[0311] L 401 may be a ligand represented by one of Formulas 402A to 402D,
[0312] L 402 may be a monodentate ligand, a bidentate ligand, or a tridentate ligand,
[0313] xc1 may be 1 or 2,
[0314] xc2 may be an integer selected from 0 to 4,
[0315] A 401 to A 404 may each independently be a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group,
[0316] T 401 to T 404 may each independently be a single bond, a double bond, *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', *-C(R 405 )(R 406 )-*', *-C(R 405 )=C(R 406 )-*', *-C(R 405 )=*', *-Si(R 405 )(R 406 )-*', *-B(R 405 )-*', *-N(R 405 )-*' or *-P(R 405 )-*',
[0317] k401 to k404 may each independently be 1, 2 or 3,
[0318] Y 401 to Y 404 may each independently be a single bond (e.g., a covalent bond or a coordination bond), *-O-*', *-S-*', *-C(R 407 )(R 408 )-*', *-Si(R 407 )(R 408 )-*', *-B(R 407 )-*', *-N(R 407 )-*' or *-P(R 407 )-*',
[0319] *1, *2, *3 and *4 in Formula 402A to Formula 402D each indicate the binding site to M in Formula 401A 401 the binding site,
[0320] R 401 to R 408 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, 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-C60 A carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 A heterocyclic group, unsubstituted or substituted by at least one R 10a substituted C6-C 60 An aryloxy group, unsubstituted or substituted by at least one R 10a substituted C6-C 60 An arylthio group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0321] R 401 to R 408 may optionally be bonded to each other to form an unsubstituted or at least one R-substituted C5-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,
[0322] b401 to b404 may each independently be an integer selected from 0 to 10,
[0323] * and *' each indicate a binding site to an adjacent atom,
[0324] Q1 to Q3 and R 10a may each independently be the same as described herein.
[0325] In an embodiment, the compound represented by Formula 401A may be a carbene complex.
[0326] As used herein, the term "carbene complex" may be a complex including a metal and a ligand bonded to the metal, wherein at least one bond between the metal and the ligand is a bond between the metal and a carbon atom of a carbene moiety.
[0327] In an embodiment, the third compound may include the compound represented by Formula 401A.
[0328] In an embodiment, the third compound may include one of Compound PD1 to Compound PD41, but the embodiment is not limited thereto:
[0329]
[0330]
[0331]
[0332] In an embodiment, R in Formula 301-1A and Formula 301-2A 301 to R 303 、R 304a to R 306a 、R 304b to R 306b and R 311 to R 314 ,R in Formula 302 321 to R 326 ,and R in Formula 401A and Formula 402A to Formula 402D 401 to R 408 may each independently be:
[0333] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl or C1-C 20 alkoxy;
[0334] C1-C 20 alkyl or C1-C 20 alkoxy each substituted with: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl or any combination thereof;
[0335] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10Alkylphenyl, naphthyl, tetrahydronaphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafuranyl or azadibenzosilolyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 alkylphenyl, naphthyl, tetrahydronaphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafuranyl, azadibenzosilolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31)、 -P(=O)(Q 31 )(Q 32 ) or any combination thereof; or
[0336] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), and
[0337] Q1 to Q3 and Q 31 to Q 33 may each be the same as those described herein.
[0338] In an embodiment, R 301 to R 303 , R 304a to R 306a , R 304b to R 306b and R 311 to R 314 , R in formula 302 321 to R 326 , and R 401 to R 408 in formula 401A and formulae 402A to 402D may each independently be:
[0339] hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy;
[0340] a group represented by one of formulae 9-1 to 9-61 or a group represented by one of formulae 10-1 to 10-348; or
[0341] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2):
[0342]
[0343]
[0344]
[0345]
[0346]
[0347]
[0348]
[0349]
[0350]
[0351] In Formulas 9-1 to 9-61 and 10-1 to 10-348, * indicates a binding site to an adjacent atom, "Ph" represents a phenyl group, "D" represents a deuterium atom, and "TMS" represents a trimethylsilyl group, and
[0352] Q1 to Q3 may each be the same as those described herein.
[0353] In an embodiment, the electron transport region of the light-emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide compound, a silicon-containing compound, or any combination thereof. In an embodiment, the hole blocking layer may contact (e.g., directly contact) the emission layer.
[0354] In an embodiment, the light-emitting device may further include a capping layer outside the first electrode or outside the second electrode.
[0355] In an embodiment, the light-emitting device may further include at least one of a first capping layer outside the first electrode and a second capping layer outside the second electrode, and at least one of the first capping layer and the second capping layer may include a polycyclic compound represented by Formula 1. The first capping layer and / or the second capping layer may be the same as those described herein.
[0356] In an embodiment, the light-emitting device may further include:
[0357] A first capping layer outside the first electrode and including a polycyclic compound represented by Formula 1;
[0358] A second capping layer outside the second electrode and including a polycyclic compound represented by Formula 1; or
[0359] Both the first capping layer and the second capping layer.
[0360] The expression "(the interlayer and / or the capping layer) includes at least one polycyclic compound represented by Formula 1" may include the following embodiments: wherein "(the interlayer and / or the capping layer) may include one polycyclic compound represented by Formula 1 or two or more different polycyclic compounds each independently represented by Formula 1".
[0361] In an embodiment, the interlayer and / or the capping layer may include only Compound 1 as the polycyclic compound represented by Formula 1. For example, Compound 1 may be present in the emission layer of the light-emitting device. In an embodiment, the interlayer may include Compound 1 and Compound 2 as the polycyclic compound represented by Formula 1. For example, Compound 1 and Compound 2 may be present in the same layer (e.g., both Compound 1 and Compound 2 may be present in the emission layer), or may be present in different layers (e.g., Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
[0362] In the specification, the term "interlayer" may be a single layer and / or multiple layers between the first electrode and the second electrode of the light-emitting device.
[0363] According to another embodiment, the electronic device may include a light-emitting device. The electronic device may further include a thin-film transistor. For example, the electronic device may further include a thin-film transistor including a source electrode and a drain electrode, wherein the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touchscreen layer, a polarization layer, or any combination thereof. The electronic device may be the same as those described herein.
[0364] According to another embodiment, the electronic apparatus may include a light-emitting device. For example, the electronic apparatus may include an electronic device including a light-emitting device. In an embodiment, the electronic apparatus 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 having a plurality of displays tiled together, a theater screen, a stadium screen, a light therapy device, or a signboard.
[0365] Figure 1 description]
[0366] Figure 1 is a schematic cross-sectional view of a light-emitting device 10 according to an embodiment. The light-emitting device 10 includes a first electrode 110, an interlayer 130, and a second electrode 150.
[0367] Hereinafter, reference will be made to Figure 1 describe the structure of the light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10.
[0368] [First electrode 110]
[0369] In Figure 1 , a substrate may be further included under the first electrode 110 or on the second electrode 150. In an embodiment, the substrate may be a glass substrate or a plastic substrate. In an embodiment, the substrate may be a flexible substrate and may include a plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0370] The first electrode 110 may be formed, for example, by depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that facilitates hole injection.
[0371] The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. In an embodiment, when the first electrode 110 is a transmissive electrode, the material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In an embodiment, when the first electrode 110 is a transflective electrode or a reflective electrode, the material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
[0372] The first electrode 110 may have a single-layer structure composed of a single layer or a multilayer structure including multiple layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.
[0373] [Interlayer 130]
[0374] The interlayer 130 may be disposed on the first electrode 110. The interlayer 130 may include an emission layer.
[0375] The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 150.
[0376] In addition to various organic materials, the interlayer 130 may further include a metal-containing compound (such as an organometallic compound) or an inorganic material (such as a quantum dot), etc.
[0377] In an embodiment, the interlayer 130 may include two or more emission units stacked between the first electrode 110 and the second electrode 150, and at least one charge generation layer between adjacent units among the two or more emission units. When the interlayer 130 includes two or more emission units and at least one charge generation layer as described above, the light-emitting device 10 may be a series light-emitting device.
[0378] [Hole transport region in the interlayer 130]
[0379] The hole transport region may have a single-layer structure composed of layers (composed of a single material), a single-layer structure composed of layers including different materials, or a multi-layer structure including multiple layers (including different materials).
[0380] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof.
[0381] In an embodiment, the hole transport region may have a multi-layer structure including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assist layer structure, a hole injection layer / emission assist layer structure, a hole transport layer / emission assist layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, where the layers in each structure may be stacked from the first electrode 110 in the order described for each, but the structure of the hole transport region is not limited thereto.
[0382] In an embodiment, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0383] [Formula 201]
[0384]
[0385] [Formula 202]
[0386]
[0387] In Formula 201 and Formula 202,
[0388] 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,
[0389] L 205 may be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or at least one R10a Substituted C1-C 20 alkylene, unsubstituted or substituted by at least one R 10a Substituted C2-C 20 alkenylene, 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,
[0390] xa1 to xa4 can each independently be an integer selected from 0 to 5,
[0391] xa5 can be an integer selected from 1 to 10,
[0392] R 201 to R 204 and Q 201 can 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,
[0393] R 201 and R 202 can optionally be linked to each other via a single bond, unsubstituted or substituted by at least one R 10a substituted C1-C5 alkylene or unsubstituted or substituted by at least one R 10a substituted C2-C5 alkenylene to form an unsubstituted or substituted by at least one R 10a substituted C8-C 60 polycyclic group (e.g., carbazolyl, etc.) (e.g., compound HT16, etc.),
[0394] R 203 and R 204 can optionally be linked to each other via a single bond, unsubstituted or substituted by at least one R 10a substituted C1-C5 alkylene or unsubstituted or substituted by at least one R 10a substituted C2-C5 alkenylene to form an unsubstituted or substituted by at least one R 10a substituted C8-C 60 polycyclic group, and
[0395] na1 can be an integer selected from 1 to 4.
[0396] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 can each independently include at least one of the groups represented by Formula CY201 to Formula CY217:
[0397]
[0398] In Formulas CY201 to CY217, R 10b and R 10c may each independently be the same as described with reference to R 10a and 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 10a
[0399] In an embodiment, in Formulas CY201 to CY217, the ring CY 201 to the ring CY 204 may each independently be phenyl, naphthyl, phenanthryl or anthracenyl.
[0400] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of the groups represented by Formulas CY201 to CY203.
[0401] In an embodiment, the compound represented by Formula 201 may include at least one of the groups represented by Formulas CY201 to CY203 and at least one of the groups represented by Formulas CY204 to CY217.
[0402] In an embodiment, in Formula 201, xa1 may be 1, R 201 may be one of the groups represented by Formulas CY201 to CY203, xa2 may be 0, and R 202 may be one of the groups represented by one of Formulas CY204 to CY207.
[0403] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the groups represented by Formulas CY201 to CY203.
[0404] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the groups represented by Formulas CY201 to CY203, and may each independently include at least one of the groups represented by Formulas CY204 to CY217.
[0405] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the groups represented by Formulas CY201 to CY217.
[0406] In an embodiment, the hole transport region 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:
[0407]
[0408]
[0409]
[0410]
[0411]
[0412] The thickness of the hole transport region may be in the range of about to about For example, the thickness of the hole transport region may be in the range of about to about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be in the range of about to about and the thickness of the hole transport layer may be in the range of about to about For example, the thickness of the hole injection layer may be in the range of about to about For example, the thickness of the hole transport layer may be in the range of about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0413] The emission assisting layer can increase the light emission efficiency by compensating for the optical resonance distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block the leakage of electrons from the emission layer to the hole transport region. The materials that can be included in the hole transport region can be included in the emission assisting layer and the electron blocking layer.
[0414] [p-dopant]
[0415] In addition to the aforementioned materials, the hole transport region may further include a charge generation material for improving the conductive properties. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer composed of the charge generation material).
[0416] The charge generation material may be, for example, a p-dopant.
[0417] For example, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level less than or equal to about -3.5 eV.
[0418] In an embodiment, the p-dopant may include a quinone derivative, a cyanide compound, a compound including element EL1 and element EL2, or any combination thereof.
[0419] Examples of the quinone derivative may include TCNQ, F4-TCNQ, etc.
[0420] Examples of the cyanide compound may include HAT-CN and the compound represented by Formula 221:[[]][Formula 221][[]]
[0421]
[0422] [Formula 221]
[0423]
[0424] In Formula 221,
[0425] 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
[0426] 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: a 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.
[0427] 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 non-metal, a metalloid, or any combination thereof.
[0428] 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.); etc.
[0429] Examples of metalloids may include silicon (Si), antimony (Sb), tellurium (Te), etc.
[0430] Examples of non-metals may include oxygen (O) and halogens (e.g., F, Cl, Br, I, etc.).
[0431] For example, a compound 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.
[0432] 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.), and rhenium oxides (e.g., ReO3, etc.).
[0433] Examples of metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides, etc.
[0434] 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, etc.
[0435] 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, etc.
[0436] 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.), etc.
[0437] Examples of post-transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (e.g., InI3, etc.), and tin halides (e.g., SnI2, etc.).
[0438] Examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3.
[0439] Examples of metalloid halides may include antimony halides (e.g., SbCl5, etc.).
[0440] 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.).
[0441] [Emission layer in the interlayer 130]
[0442] When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer according to sub-pixels. In an embodiment, the emission layer may have a stacked structure in which two or more of the red emission layer, the green emission layer, and the blue emission layer may be in contact with each other or may be separated from each other to emit white light. In an embodiment, the emission layer may have a structure in which two or more of the red light-emitting material, the green light-emitting material, and the blue light-emitting material may be mixed with each other in a single layer to emit white light.
[0443] In an embodiment, the emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0444] Based on 100 parts by weight of the host, the amount of the dopant in the emission layer can be in the range of about 0.01 part by weight to about 15 parts by weight.
[0445] In an embodiment, the emission layer can include quantum dots.
[0446] In an embodiment, the emission layer can include a delayed fluorescence material. The delayed fluorescence material can be used as the host or the dopant in the emission layer.
[0447] The thickness of the emission layer can be in the range of about to about . For example, the thickness of the emission layer can be in the range of about to about . When the thickness of the emission layer is within any of these ranges, excellent light-emitting characteristics can be obtained without significantly increasing the driving voltage.
[0448] [Host]
[0449] In an embodiment, the host can further include a compound represented by Formula 301:
[0450] [Formula 301]
[0451] [Ar 301 xb11 -[(L 301 ) xb1 -R 301 xb21 .
[0452] In Formula 301,
[0453] Ar 301 and L 301 can 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,
[0454] xb11 can be 1, 2, or 3,
[0455] xb1 can be an integer selected from 0 to 5,
[0456] R 301 can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, 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, 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(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 ),
[0457] xb21 can be an integer selected from 1 to 5, and
[0458] Q 301 to Q 303 can each independently be the same as described for Q1.
[0459] 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.
[0460] In an embodiment, the host can include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0461] [Formula 301-1]
[0462]
[0463] [Formula 301-2]
[0464]
[0465] In Formula 301-1 and Formula 301-2,
[0466] Ring A 301 to Ring A 304 can 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,
[0467] X 301 may be O, S, N[(L 304 ) xb4 -R 304 , C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0468] xb22 and xb23 may each independently be 0, 1 or 2,
[0469] L 301 , xb1 and R 301 may each be the same as described herein,
[0470] L 302 to L 304 may each independently be the same as that described with reference to L 301 .
[0471] xb2 to xb4 may each independently be the same as that described with reference to xb1, and
[0472] R 302 to R 305 and R 311 to R 314 may each independently be the same as that described herein with reference to R 301 .
[0473] In an embodiment, the host may include an alkaline earth metal complex, a post-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.
[0474] 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(9-carbazolyl)benzene (mCP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), or any combination thereof:
[0475]
[0476]
[0477]
[0478]
[0479]
[0480]
[0481]
[0482] [Phosphorescent dopant]
[0483] In an embodiment, the phosphorescent dopant may include at least one transition metal as a central metal.
[0484] 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.
[0485] The phosphorescent dopant may be electrically neutral.
[0486] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0487] [Formula 401]
[0488] M(L 401 ) xc1 (L 402 ) xc2
[0489] [Formula 402]
[0490]
[0491] In Formulas 401 and 402,
[0492] M may be a transition metal (e.g., Ir, Pt, Pd, Os, Ti, Au, Hf, Eu, Tb, Rh, Re, or Tm),
[0493] 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,
[0494] 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,
[0495] X 401 and X 402 may each independently be nitrogen or carbon,
[0496] Ring A 401and ring A 402 may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0497] T 401 may 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=*',
[0498] X 403 and X 404 may 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 ),
[0499] Q 411 to Q 414 may each independently be the same as described with reference to Q1,
[0500] R 401 and R 402 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, 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)(Q 401 ), -S(=O)2(Q 401) or -P(=O)(Q 401 )(Q 402 ),
[0501] Q 401 to Q 403 may each independently be the same as described with reference to Q1,
[0502] xc11 and xc12 may each independently be an integer selected from 0 to 10, and
[0503] * and *' in Formula 402 each indicate a binding site to M in Formula 401.
[0504] For example, in Formula 402, X 401 may be nitrogen and X 402 may be carbon, or X 401 and X 402 may each be nitrogen.
[0505] In an embodiment, in Formula 401, when xc1 is 2 or greater, two or more of the two rings A in L 401 may optionally be connected to each other via T as a linking group 401 , or two or more of the two rings A in L 402 401 may optionally be connected to each other via T as a linking group 402 403 402 403 (see Compounds PD1 to PD4 and Compound PD7). T 402 and T 403 may each independently be the same as described with reference to T 401 .
[0506] In Formula 401, L 402 may be an organic ligand. For example, L 402 may 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., a phosphine group, a phosphite group, etc.) or any combination thereof.
[0507] In an embodiment, the phosphorescent dopant may include, for example, one or any combination of Compounds PD1 to PD39:
[0508]
[0509]
[0510]
[0511] [Fluorescent dopant]
[0512] The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
[0513] In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:
[0514] [Formula 501]
[0515]
[0516] In Formula 501,
[0517] 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.
[0518] xd1 to xd3 may each independently be 0, 1, 2, or 3, and
[0519] xd4 may be 1, 2, 3, 4, 5, or 6.
[0520] 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.).
[0521] In an embodiment, in Formula 501, xd4 may be 2.
[0522] In an embodiment, the fluorescent dopant may include one of Compounds FD1 to FD37, DPVBi, DPAVBi, or any combination thereof:
[0523]
[0524]
[0525]
[0526] [Thermally activated delayed fluorescence material]
[0527] In an embodiment, the emissive layer may include a thermally activated delayed fluorescence material.
[0528] In the present specification, 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.
[0529] Depending on the type of other materials included in the emission layer, the delayed fluorescence material included in the emission layer can be used as a host or a dopant.
[0530] 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 satisfies the above range, the up-conversion from the triplet state to the singlet state of the delayed fluorescence material can occur effectively. Thus, the light-emitting device 10 can have improved luminous efficiency.
[0531] 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, etc.) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a π - electron deficient nitrogen - containing C1 - C 60 ring group, etc.); or a material including a C8 - C 60 polycyclic group in which two or more ring groups are fused while sharing boron (B).
[0532] In an embodiment, the delayed fluorescence material can include, for example, at least one of Compound DF1 to Compound DF14:
[0533]
[0534]
[0535] [Quantum dots]
[0536] In an embodiment, the emission layer can include quantum dots.
[0537] In the specification, the quantum dots can be crystals of semiconductor compounds and can include any material capable of emitting light of various emission wavelengths according to the size of the crystals.
[0538] The diameter of the quantum dots can be in the range of, for example, about 1 nm to about 10 nm.
[0539] The quantum dots can be synthesized by a wet chemical process, a metalorganic chemical vapor deposition (MOCVD) process, a molecular beam epitaxy (MBE) process, or any process similar thereto.
[0540] 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 naturally serves as a dispersant coordinated on the surface of the quantum dot particle crystals and controls the growth of the quantum dot particle crystals 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 metalorganic chemical vapor deposition or molecular beam epitaxy.
[0541] 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.
[0542] Examples of Group II-VI semiconductor compounds can include: binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, and MgZnS; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and HgZnSTe; or any combination thereof.
[0543] Examples of group III-V semiconductor compounds may include: binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, etc.; or any combination thereof. In an embodiment, the 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 may include InZnP, InGaZnP, InAlZnP, etc.
[0544] Examples of group III-VI semiconductor compounds may include: binary compounds such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, etc.; ternary compounds such as InGaS3, InGaSe3, etc.; or any combination thereof.
[0545] Examples of group I-III-VI semiconductor compounds may include: ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, etc.; or any combination thereof.
[0546] Examples of group IV-VI semiconductor compounds may include: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, etc.; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, etc.; quaternary compounds such as SnPbSSe, SnPbSeTe, SnPbSTe, etc.; or any combination thereof.
[0547] 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.
[0548] For example, each element included in a compound such as a binary compound, a ternary compound, or a quaternary compound may be present in the particles at a uniform concentration or at a non-uniform concentration.
[0549] In an embodiment, the quantum dots may have a single structure (wherein 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.
[0550] The shell of the quantum dots may serve as a protective layer for preventing chemical denaturation of the core to maintain semiconductor properties, and / or may serve as a charging layer for imparting electrophoretic properties to the quantum dots. The shell may be single-layered or multi-layered. The interface between the core and the shell may have a concentration gradient, where the concentration of the material present in the shell decreases towards the center of the core.
[0551] Examples of the shell of the quantum dots may include metal oxides, metalloid oxides, non-metal oxides, semiconductor compounds, or any combination thereof. Examples of metal oxides, metalloid oxides, or non-metal oxides may include: binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and NiO; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and CoMn2O4; or any combination thereof.
[0552] Examples of the semiconductor compounds as described above may include group II-VI semiconductor compounds, group III-V semiconductor compounds, group III-VI semiconductor compounds, group I-III-VI semiconductor compounds, group IV-VI semiconductor compounds, or any combination thereof. Examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0553] The full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dots may be less than or equal to about 45 nm. For example, the FWHM of the emission wavelength spectrum of the quantum dots may be less than or equal to about 40 nm. For example, the FWHM of the emission wavelength spectrum of the quantum dots may be less than or equal to about 30 nm. When the quantum dots have an FWHM of the emission wavelength spectrum within any of these ranges, the color purity or color reproducibility of the quantum dots may be improved. The light emitted by the quantum dots may be emitted in all directions, such that a wide viewing angle may be improved.
[0554] In an embodiment, the quantum dots may be nanoparticles, nanotubes, nanowires, nanofibers, nanoplatelets, etc., or the quantum dots may be in the form of spherical particles, cone particles, multi-armed particles, or cubic particles.
[0555] By controlling the size of the quantum dots, the band gap may be adjustable so that light with various wavelength bands can be obtained from the emission layer including the quantum dots. Accordingly, by using quantum dots of different sizes, a light-emitting device that emits light with various wavelength bands can be implemented. In an embodiment, the size of the quantum dots 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 by combining lights of various colors.
[0556] [Electron transport region in interlayer 130]
[0557] The electron transport region may have a single-layer structure composed of layers (composed of a single material), a single-layer structure composed of layers including different materials, or a multi-layer structure including multiple layers (including different materials).
[0558] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0559] In an embodiment, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, and the layers of each structure may be stacked from the emission layer in the order described respectively, but the structure of the electron transport region is not limited thereto.
[0560] In an embodiment, the electron transport region (e.g., the buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a metal-free compound including at least one nitrogen-containing C1-C 60 aromatic ring group lacking π electrons.
[0561] In an embodiment, the electron transport region may include a compound represented by Formula 601:
[0562] [Formula 601]
[0563] [Ar 601 xe11 -[(L 601 ) xe1 -R 601 xe21 .
[0564] In Formula 601,
[0565] Ar 601 and L 601 may each independently be unsubstituted or substituted by at least one R 10a -C3-C 60 carbocyclic group or unsubstituted or substituted by at least one R 10a -C1-C 60 heterocyclic group,
[0566] xe11 may be 1, 2 or 3,
[0567] xe1 may be 0, 1, 2, 3, 4 or 5,
[0568] R 601 may be unsubstituted or substituted by at least one R 10a -C3-C 60 carbocyclic group, unsubstituted or substituted by at least one R 10a -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 ),
[0569] Q 601 to Q 603 may each independently be the same as described with reference to Q1,
[0570] xe21 may be 1, 2, 3, 4 or 5, and
[0571] Ar 601 、L 601 and R 601 at least one of which may each independently be unsubstituted or substituted by at least one R 10a substituted π-deficient nitrogen-containing C1-C 60 cyclic group.
[0572] In an embodiment, in Formula 601, when xe11 is 2 or greater, two or more Ar 601 may be connected to each other via a single bond.
[0573] In an embodiment, in Formula 601, Ar 601 may be unsubstituted or substituted by at least one R 10a substituted anthryl group.
[0574] In an embodiment, the electron transport region may include a compound represented by Formula 601-1:
[0575] [Formula 601-1]
[0576]
[0577] In formula 601-1,
[0578] X 614 can be N or C(R 614 ), X 615 can be N or C(R 615 ), and X 616 can be N or C(R 616 ), where at least one of X 614 to X 616 can each be N,
[0579] L 611 to L 613 can each independently be the same as described with reference to L 601 .
[0580] Xe611 to xe613 can each independently be the same as described with reference to xe1
[0581] R 611 to R 613 can each independently be the same as described with reference to R 601 , and
[0582] R 614 to R 616 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclic group or unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclic group.
[0583] In an embodiment, in formula 601 and formula 601-1, xe1 and xe611 to xe613 can each independently be 0, 1, or 2.
[0584] In an embodiment, the electron transport region can include one of compounds ET1 to compound 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:
[0585]
[0586]
[0587]
[0588] The thickness of the electron transport region can be in the range of about to about For example, the thickness of the electron transport region can be in the range of about to about When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer 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 hole blocking layer, or 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 hole blocking layer, the electron control layer, the electron transport layer, and / or the electron transport region is within the above ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.
[0589] In addition to the foregoing materials, the electron transport region (e.g., the electron transport layer in the electron transport region) can further include a metal-containing material.
[0590] The metal-containing material can include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkali metal complex can be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the metal ion of the alkaline earth metal complex can be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the metal ion of the alkaline earth metal complex can 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.
[0591] In an embodiment, the metal-containing material can include a Li complex. The Li complex can include, for example, compound ET-D1 (Liq) or compound ET-D2:
[0592]
[0593] The electron transport region can include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer can contact (e.g., directly contact) the second electrode 150.
[0594] The electron injection layer may have a single-layer structure composed of layers (composed of a single material), a single-layer structure composed of layers including different materials, or a multi-layer structure including multiple layers (including different materials).
[0595] In an embodiment, the electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0596] 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.
[0597] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may be oxides, halides (e.g., fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
[0598] 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) and Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1), etc. The rare earth metal compound may include 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, etc.
[0599] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may include: alkali metal ions, alkaline earth metal ions, or rare earth metal ions; and ligands bonded to the metal ions (e.g., hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof).
[0600] In an embodiment, the electron injection layer may be composed of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In an embodiment, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
[0601] In an embodiment, the electron injection layer may be composed of an alkali metal-containing compound (e.g., an alkali metal halide), or the electron injection layer may be composed of an alkali metal-containing compound (e.g., an alkali metal halide) and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In an embodiment, the electron injection layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, etc.
[0602] When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0603] 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 these ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0604] [Second Electrode 150]
[0605] The second electrode 150 may be disposed on the interlayer 130 having the aforementioned structure. 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 materials having a low work function, such as metals, alloys, conductive compounds, or any combination thereof.
[0606] The second electrode 150 may include Li, Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, Yb, Ag-Yb, ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a transmissive-reflective electrode, or a reflective electrode.
[0607] The second electrode 150 may have a single-layer structure or a multi-layer structure.
[0608] [Capping layer]
[0609] The light-emitting device 10 may include a first capping layer outside the first electrode 110 and / or a second capping layer outside the second electrode 150. In an embodiment, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked in this order, a structure in which the first electrode 110, the interlayer 130, 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 130, the second electrode 150, and the second capping layer are stacked in this order.
[0610] The light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted to the outside through the first electrode 110 that can serve as a semi-transmissive electrode or a transmissive electrode and through the first capping layer. The light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted to the outside through the second electrode 150 that can serve as a semi-transmissive electrode or a transmissive electrode and through the second capping layer.
[0611] The first capping layer and the second capping layer may each increase the external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 can be increased, and accordingly, the light-emitting efficiency of the light-emitting device 10 can be improved.
[0612] The first capping layer and the second capping layer may each include a material having a refractive index greater than or equal to about 1.6 (relative to a wavelength of about 589 nm).
[0613] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
[0614] At least one of the first capping layer and the second capping layer may 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 may optionally be substituted with substituents including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amino group-containing compound.
[0615] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0616] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include one of Compound HT28 to Compound HT33, one of Compound CP1 to Compound CP6, β-NPB, or any combination thereof:
[0617]
[0618] [Film]
[0619] The polycyclic compound represented by Formula 1 may be included in various films. Accordingly, another embodiment provides a film including the polycyclic compound represented by Formula 1. The film may 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 layer containing quantum dots, etc.), a light blocking member (e.g., a light reflection layer or a light absorption layer, etc.), or a protective member (e.g., an insulating layer or a dielectric layer, etc.).
[0620] [Electronic Device]
[0621] The light-emitting device may be included in various electronic devices. For example, the electronic device including the light-emitting device may be a light-emitting device or an authentication device, etc.
[0622] In addition to the light-emitting device, the electronic device (e.g., a light-emitting device) may further include a color filter, a color conversion layer, or both 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 travels. For example, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be the same as that described herein. In an embodiment, the color conversion layer may include quantum dots. The quantum dots may be, for example, the aforementioned quantum dots.
[0623] 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.
[0624] The pixel defining layer may be disposed between the plurality of sub-pixels to define each sub-pixel.
[0625] The color filter may further include a plurality of color filter regions and a light-shielding pattern therebetween, and the color conversion layer may further include a plurality of color conversion regions and a light-shielding pattern therebetween.
[0626] The color filter region (or color conversion region) may include a first region emitting first color light, a second region emitting second color light, and / or a third region emitting third color light, where the first color light, the second color light, and / or the third color light 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 color filter region (or color conversion region) may include quantum dots. In an embodiment, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. The quantum dots may be the same as those described herein. The first region, the second region, and / or the third region may each further include a scatterer.
[0627] In an embodiment, in a light-emitting device emitting first light, the first region may absorb the first light to emit first-first color light, the second region may absorb the first light to emit second-first color light, and the third region may absorb the first light to emit third-first color light. The first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths from each other. In an embodiment, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
[0628] In addition to the foregoing light-emitting device, the electronic device may further include a thin-film transistor. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, where any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light-emitting device.
[0629] The thin-film transistor may further include a gate electrode, a gate insulating film, etc.
[0630] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, etc.
[0631] The electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be disposed between the color filter and / or color conversion layer and the light-emitting device. The sealing portion may allow the light from the light-emitting device to be extracted to the outside, and may prevent environmental air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.
[0632] In addition to the color filter and / or color conversion layer, various functional layers may be further included on the sealing portion according to the use of the electronic device. 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 (e.g., a fingertip, a pupil, etc.).
[0633] In addition to the light-emitting device as described above, the authentication device may further include a biometric information collector.
[0634] The electronic device may 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 machines, 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 measurement tools, meters (e.g., meters for vehicles, aircraft, and ships), and projectors, etc.
[0635] [Electronic equipment]
[0636] The light-emitting device may be included in various types of electronic equipment.
[0637] For example, the electronic equipment including the light-emitting 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 having a plurality of displays tiled together, a theater screen, a stadium screen, a light therapy device, or a signboard.
[0638] The light-emitting device may have excellent luminous efficiency and a long lifespan, and thus electronic equipment including the light-emitting device may have characteristics such as high brightness, high resolution, and low power consumption.
[0639] Figure 2 and Figure 3 description of]
[0640] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment.
[0641] Figure 2 The electronic device of includes a substrate 100, a thin film transistor (TFT), a light-emitting device, and a sealing portion 300 that seals the light-emitting device.
[0642] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 may prevent the penetration of impurities through the substrate 100 and provide a flat surface on the substrate 100.
[0643] The TFT may be disposed on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0644] The active layer 220 may include an inorganic semiconductor (such as silicon or polysilicon), an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0645] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be disposed on the active layer 220, and the gate electrode 240 may be disposed on the gate insulating film 230.
[0646] An interlayer insulating film 250 may be disposed on the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 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.
[0647] The source electrode 260 and the drain electrode 270 may be disposed 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.
[0648] 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 130, and a second electrode 150.
[0649] The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270 and may expose a part of the drain electrode 270. The first electrode 110 may be electrically connected to the exposed portion of the drain electrode 270.
[0650] The pixel defining layer 290 including an insulating material may be disposed on the first electrode 110. The pixel defining layer 290 may expose a region of the first electrode 110, and the interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide-based organic film or a polyacrylate-based organic film. Although not shown in Figure 2 , at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 and be provided in the form of a common layer.
[0651] The second electrode 150 may be disposed on the interlayer 130, and a capping layer 170 may be further included on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0652] The sealing part 300 may be located on the capping layer 170. The sealing part 300 may be disposed on the light-emitting device to protect the light-emitting device from moisture and / or oxygen. The sealing 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, polyvinyl sulfonate, polyformaldehyde, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), epoxy resin (e.g., aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or any combination of an inorganic film and an organic film.
[0653] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment.
[0654] Figure 3 The electronic device of Figure 2 may be different from the electronic device of Figure 3 at least in that a light-shielding pattern 500 and a functional region 400 are further included on the sealing part 300. The functional region 400 may be a color filter region, a color conversion region, or a combination of a color filter region and a color conversion region. In an embodiment, Figure 3 the light-emitting device included in the electronic device of
[0655] Figure 4 description of
[0656] Figure 4Schematic perspective view of an electronic device 1 including a light-emitting device according to an embodiment.
[0657] The electronic device 1, which can be a device for displaying moving images or still images, can be not only a portable electronic device such as a mobile phone, a smartphone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook computer, an e-book, a portable multimedia player (PMP), a navigation device, or a ultra-mobile PC (UMPC), but also various products or a part thereof, such as a television, a laptop computer, a monitor, a billboard, or an Internet of Things (IoT) device. In an embodiment, the electronic device 1 can be a wearable device or a part thereof, such as a smart watch, a watch phone, a glasses-type display, or a head-mounted display (HMD). However, the embodiment is not limited thereto.
[0658] Examples of the electronic device 1 can include an instrument panel of a vehicle, a center console of a vehicle or a center information display on the instrument panel, an in-vehicle rearview mirror display replacing a side-view mirror of a vehicle, an entertainment display arranged for a rear seat of a vehicle or arranged on the backrest of a front seat, a head-up display (HUD) mounted in front of a vehicle or projected on a windshield, or a computer-generated holographic augmented reality head-up display (CGH AR HUD). For ease of explanation, Figure 4 the case where the electronic device 1 is a smartphone is illustrated.
[0659] The electronic device 1 can include a display area DA and a non-display area NDA outside the display area DA. The display device can implement an image through a two-dimensional array of pixels arranged in the display area DA.
[0660] The non-display area NDA can be an area that does not display an image and can surround the display area DA. A driver for supplying an electrical signal or power to a display element arranged in the display area DA can be arranged in the non-display area NDA. A pad can be arranged in the non-display area NDA, and the pad can be electrically connected to an electronic component or a printed circuit board.
[0661] 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 4 shown, the length in the x-axis direction can be shorter 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 longer than the length in the y-axis direction.
[0662] Figure 5 and Figures 6A to 6C description of
[0663] Figure 5 Schematic diagram of the exterior of a vehicle 1000 as an electronic device including a light-emitting device according to an embodiment. Figures 6A to 6C Schematic diagrams of the interior of the vehicle 1000 according to respective embodiments.
[0664] See Figure 5 、 Figure 6A 、 Figure 6B and Figure 6C ,the vehicle 1000 may 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 point. The vehicle 1000 may include vehicles traveling on roads or tracks, vessels moving on the ocean or rivers, and airplanes flying in the air by utilizing the action of air, etc.
[0665] The vehicle 1000 may travel on a road or track. The vehicle 1000 may move in a selectable direction according to the rotation of at least one wheel. In an embodiment, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, construction machinery, a two-wheeled vehicle, a prime mover device, a bicycle, and a train traveling on a track.
[0666] The vehicle 1000 may include a body having an interior and an exterior, and a chassis that does not include the body portion where the mechanical equipment required for driving is installed as other components. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and pillars provided at the boundaries between doors, etc. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a driving device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, front wheels and rear wheels, and left wheels and right wheels, etc.
[0667] The vehicle 1000 may include side window glass 1100, 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.
[0668] The side window glass 1100 and the front window glass 1200 may be separated by pillars arranged between the side window glass 1100 and the front window glass 1200.
[0669] The side window glass 1100 may be installed on one side of the vehicle 1000. In an embodiment, the side window glass 1100 may be installed on the door of the vehicle 1000. A plurality of side window glass 1100 may be provided and may face each other. In an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be arranged adjacent to the instrument panel 1400, and the second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.
[0670] In an embodiment, the side window glasses 1100 may be spaced apart from each other in the x-axis direction or the -x-axis direction (a direction opposite to the x-axis direction). In an embodiment, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x-axis direction or the -x-axis direction. For example, a virtual straight line L connecting the side window glasses 1100 may extend in the x-axis direction or the -x-axis direction. In an embodiment, a virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend in the x-axis direction or the -x-axis direction.
[0671] The front window glass 1200 may be installed in front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.
[0672] The side mirror 1300 may provide a rear view of the vehicle 1000. The side mirror 1300 may be installed on an outer portion of the vehicle body. In an embodiment, a plurality of side mirrors 1300 may be provided. One of the plurality of side mirrors 1300 may be disposed outside the first side window glass 1110, and another of the plurality of side mirrors 1300 may be disposed outside the second side window glass 1120.
[0673] The instrument panel 1400 may be disposed in front of the steering wheel. The instrument panel 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a speedometer, an automatic shift lever indicator, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0674] The center console 1500 may include a control panel on which buttons for adjusting an audio device, an air conditioning device, and a seat heater are provided. The center console 1500 may be disposed on one side of the instrument panel 1400.
[0675] The passenger seat instrument panel 1600 may be spaced apart from the instrument panel 1400, and the center console 1500 is disposed between the instrument panel 1400 and the passenger seat instrument panel 1600. In an embodiment, the instrument panel 1400 may be disposed corresponding to the driver's seat (not shown), and the passenger seat instrument panel 1600 may be disposed corresponding to the passenger seat (not shown). In an embodiment, the instrument panel 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.
[0676] In an embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be disposed inside the vehicle 1000. In an embodiment, the display device 2 may be disposed between side window glasses 1100 facing each other. The display device 2 may be disposed on at least one of the instrument panel 1400, the center console 1500, and the passenger seat instrument panel 1600.
[0677] The display device 2 may include an organic light-emitting display device, an inorganic electroluminescent display device, a quantum dot display device, etc. Hereinafter, an organic light-emitting display device including a light-emitting device according to an embodiment will be described as an example of the display device 2. However, the foregoing various types of display devices may be used in the embodiment.
[0678] See Figure 6A , the display device 2 may be disposed on the center console 1500. In an embodiment, the display device 2 may display navigation information. In an embodiment, the display device 2 may display information regarding audio settings, video settings, or vehicle settings.
[0679] See Figure 6B , the display device 2 may be disposed on the instrument panel 1400. In an embodiment, the instrument panel 1400 may display driving information and the like through the display device 2. For example, the instrument panel 1400 may digitize the driving information. The instrument panel 1400 may digitally display vehicle information and driving information as images. In an embodiment, the pointer and instrument of the tachometer and various appropriate warning lights or icons may be displayed through digital signals.
[0680] See Figure 6C , the display device 2 may be disposed on the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or disposed on the passenger seat instrument panel 1600. In an embodiment, the display device 2 disposed on the passenger seat instrument panel 1600 may display an image related to the information displayed on the instrument panel 1400 and / or the information displayed on the center console 1500. In an embodiment, the display device 2 disposed on the passenger seat instrument panel 1600 may display information different from the information displayed on the instrument panel 1400 and / or the information displayed on the center console 1500.
[0681] [Manufacturing Method]
[0682] The layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region may be formed in a selected region by using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.
[0683] When forming the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region by vacuum deposition, depending on the materials to be included in the layer to be formed and the structure of the layer to be formed, at a deposition temperature in the range of about 100 °C to about 500 °C, at a vacuum degree in the range of about -8 torr to about -3 torr, and at a deposition rate in the range of about to about deposition is carried out.
[0684] [Definition of Terms]
[0685] As used herein, the term "C3-C 60 carbocyclic group" may be a cyclic group composed of only 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, and as used herein, the term "C1-C 60 heterocyclic group" may be a cyclic group having 1 to 60 carbon atoms and further having heteroatoms as ring-forming atoms in addition to carbon. 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. The C3-C 60 carbocyclic group and the C1-C 60 heterocyclic group may each be a monocyclic group composed of one ring or a polycyclic group in which two or more rings are fused to each other. In an embodiment, the number of ring-forming atoms of the C1-C 60 heterocyclic group may be 3 to 61.
[0686] As used herein, the term "cyclic group" may be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group.
[0687] 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, and as used herein, the term "π-electron-deficient nitrogen-containing C1-C 60 cyclic group" may be a heterocyclic group having 1 to 60 carbon atoms and may include *-N=*' as a ring-forming moiety.
[0688] In an embodiment,
[0689] C3-C 60 The carbocyclic group may be a T1 group, or a group in which two or more T1 groups are fused to each other (for example, cyclopentadienyl, adamantyl, norbornyl, phenyl, pentaphenylenyl, naphthyl, azulenyl, indacenyl, acenaphthylenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, perylenyl, pentaphenylene, heptaphenylenyl, tetracenyl, picenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indeno[1,2,3-cd]phenanthryl or indeno[1,2,3-cd]anthracenyl),
[0690] C1-C 60 The heterocyclic group may be a T2 group, a group in which at least two T2 groups are fused to each other, or a group in which at least one T2 group and at least one T1 group are fused to each other (for example, pyrrolyl, thienyl, furyl, indolyl, benzoindolyl, naphthoindolyl, isoindolyl, benzoisoindolyl, naphthoisoindolyl, benzothiophen-2-yl, benzothienyl, benzofuryl, carbazolyl, dibenzothiophen-2-yl, dibenzothienyl, dibenzofuryl, indacarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzothiophen-2-ylcarbazolyl, benzoindolocarbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, benzonaphthothiophen-2-yl, 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, azadibenzothiophen-2-yl, azadibenzothienyl or azadibenzofuryl, etc.),
[0691] 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 (for example, C3-C 60a carbocyclic group, 1H-pyrrolyl, silolyl, borolyl, 2H-pyrrolyl, 3H-pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthindolyl, isoindolyl, benzoisoindolyl, naphthoisoindolyl, benzosilolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuryl, indolocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilolocarbazolyl, benzindolocarbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, benzonaphthosilolyl, benzofurodibenzofuryl, benzofurodibenzothienyl or benzothienodibenzothienyl, etc.)
[0692] a π-deficient nitrogen-containing C1-C 60 The cyclic group may be a T4 group, a group in which at least two T4 groups are fused to each other, a group in which at least one T4 group and at least one T1 group are fused to each other, a group in which at least one T4 group and at least one T3 group are fused to each other, or a group in which at least one T4 group, at least one T1 group and at least one T3 group are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, benzoisothiazolyl, 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 and azadibenzofuryl, etc.)
[0693] wherein the T1 group may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo[2.2.1]heptane) group, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl or phenyl
[0694] The T2 group can be a furyl group, a thienyl group, a 1H-pyrrolyl group, a silolyl group, a borole group, a 2H-pyrrolyl group, a 3H-pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, an aza-silolyl group, an aza-borole group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a tetrazinyl group, a pyrrolidinyl group, an imidazolidinyl group, a dihydropyrrolyl group, a piperidinyl group, a tetrahydropyridyl group, a dihydropyridyl group, a hexahydropyrimidinyl group, a tetrahydropyrimidinyl group, a dihydropyrimidinyl group, a piperazinyl group, a tetrahydropyrazinyl group, a dihydropyrazinyl group, a tetrahydropyridazinyl group or a dihydropyridazinyl group,
[0695] The T3 group can be a furyl group, a thienyl group, a 1H-pyrrolyl group, a silolyl group or a borole group, and
[0696] The T4 group can include a 2H-pyrrolyl group, a 3H-pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, an aza-silolyl group, an aza-borole group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group or a tetrazinyl group.
[0697] As used herein, the terms "cyclic group", "C3-C 60 carbocyclic group", "C1-C 60 heterocyclic group", "π-electron-rich C3-C 60 cyclic group" or "nitrogen-containing π-electron-deficient C1-C 60 cyclic group" can each be a group fused to an arbitrary cyclic group, monovalent group or polyvalent group (e.g., divalent group, trivalent group, tetravalent group, etc.) according to the structure of the formula using the corresponding term. For example, as used herein, "phenyl" can be a benzo group, a phenyl group or a phenylene group, etc., and those of ordinary skill in the art can easily understand these groups according to the structure of the formula including "phenyl".
[0698] Examples of the monovalent C3-C 60 carbocyclic group or monovalent C1-C 60 heterocyclic group can include C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group. Examples of the divalent C3-C 60 carbocyclic group or divalent C1-C 60 heterocyclic group can include C3-C 10 subcycloalkyl group, C1-C 10Azacycloalkyl, C3-C 10 Cycloalkenylene, C1-C 10 Azacycloalkenylene, C6-C 60 Arylene, C1-C 60 Heteroarylene, divalent non-aromatic fused polycyclic group, and divalent non-aromatic fused heteropolycyclic group.
[0699] As used herein, the term "C1-C 60 alkyl" may be a straight-chain or branched-chain monovalent aliphatic hydrocarbon group having 1 to 60 carbon atoms. For example, C1-C 50 alkyl, C1-C 30 alkyl, C1-C 20 alkyl, or C1-C 10 alkyl, and examples thereof may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, and tert-decyl. As used herein, the term "C1-C 60 alkylene" may be a divalent group having substantially the same structure as C1-C 60 alkyl.
[0700] 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, etc. As used herein, the term "C2-C 60 alkenylene" may be a divalent group having substantially the same structure as C2-C 60 alkenyl.
[0701] 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, etc. As used herein, the term "C2-C 60 alkynylene" may be a divalent group having substantially the same structure as C2-C 60An alkynyl group is a divalent group having substantially the same structure.
[0702] As used herein, the term "C1-C 60 alkoxy" may be a monovalent group represented by -O(A 101 )(where A 101 may be a C1-C 60 alkyl group), for example, C1-C 30 alkoxy, C1-C 20 alkoxy or C1-C 10 alkoxy, and examples thereof may include methoxy, ethoxy, and isopropoxy, etc.
[0703] 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 cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl, etc. As used herein, the term "C3-C 10 subcycloalkyl" may be a divalent group having substantially the same structure as C3-C 10 cycloalkyl.
[0704] As used herein, the term "C1-C 10 heterocycloalkyl" may be a monovalent cyclic group having 1 to 10 carbon atoms that further includes at least one heteroatom as a ring-forming atom in addition to carbon atoms, and examples thereof may include 1,2,3,4-oxadiazolyl, tetrahydrofuryl, and tetrahydrothienyl, etc. As used herein, the term "C1-C 10 subheterocycloalkyl" may be a divalent group having substantially the same structure as C1-C 10 heterocycloalkyl.
[0705] As used herein, the term "C3-C 10 cycloalkenyl" may be a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its cyclic structure and having no aromaticity, and examples thereof may include cyclopentenyl, cyclohexenyl, and cycloheptenyl, etc. As used herein, the term "C3-C 10 subcycloalkenyl" may be a divalent group having substantially the same structure as C3-C 10 cycloalkenyl.
[0706] As used herein, the term "C1-C 10"Heterocycloalkenyl" may be a monovalent cyclic group of 1 to 10 carbon atoms that further includes at least one heteroatom as a ring-forming atom and at least one double bond in its cyclic structure. C1-C 10 Examples of heterocycloalkenyl may include 4,5-dihydro-1,2,3,4-oxadiazolyl, 2,3-dihydrofuranyl, 2,3-dihydrothienyl, and the like. As used herein, the term "C1-C 10 "Heterocycloalkenylene" may be a divalent group having substantially the same structure as C1-C 10 heterocycloalkenyl.
[0707] 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. And 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. C6-C 60 Examples of aryl may include phenyl, pentacenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthrenyl, perylenyl, pentaphenyl, heptacenyl, tetracenyl, picenyl, hexaphenyl, pentaphenyl, rubicenyl, corannulenyl, and ovalenyl, and the like. When C6-C 60 aryl and C6-C 60 arylene each include two or more rings, the two or more rings may be fused to each other respectively.
[0708] As used herein, the term "C1-C 60 "Heteroaryl" may be a monovalent group of a heteroaromatic system having 1 to 60 carbon atoms that further includes at least one heteroatom as a ring-forming atom. For example, C1-C 50 heteroaryl, C1-C 40 heteroaryl, C1-C 30 heteroaryl, C1-C 20 heteroaryl, or C1-C 10 heteroaryl. As used herein, the term "C1-C 60 "Heteroarylene" may be a divalent group of a heteroaromatic system having 1 to 60 carbon atoms that further includes at least one heteroatom as a ring-forming atom. C1-C 60Examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, etc. When C1-C 60 the heteroaryl group and C1-C 60 the heteroarylene group each include two or more rings, and the two or more rings may be fused to each other respectively.
[0709] 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 as ring-forming atoms and generally no aromaticity in the molecular structure (e.g., having 8 to 60 carbon atoms), e.g., C8-C 60 monovalent non-aromatic fused polycyclic group, C8-C 50 monovalent non-aromatic fused polycyclic group, C8-C 40 monovalent non-aromatic fused polycyclic group, C8-C 30 monovalent non-aromatic fused polycyclic group or C8-C 20 monovalent non-aromatic fused polycyclic group. Examples of monovalent non-aromatic fused polycyclic groups may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenoanthracenyl, indenoacenaphthylenyl, etc. As used herein, the term "divalent non-aromatic fused polycyclic group" may be a divalent group having substantially the same structure as the above monovalent non-aromatic fused polycyclic group.
[0710] 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 and generally having no aromaticity in its molecular structure (e.g., having 1 to 60 carbon atoms), e.g., C1-C 60 monovalent non-aromatic fused heteropolycyclic group, C1-C 50 monovalent non-aromatic fused heteropolycyclic group, C1-C 40 monovalent non-aromatic fused heteropolycyclic group, C1-C 30 monovalent non-aromatic fused heteropolycyclic group or C1-C 20Monovalent non-aromatic fused heteropolycyclic group. Examples of monovalent non-aromatic fused heteropolycyclic groups 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. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" may be a divalent group having substantially the same structure as the monovalent non-aromatic fused heteropolycyclic group.
[0711] 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, and 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.
[0712] As used herein, the term "C7-C 60 aralkyl" may be represented by -(A 104 )(A 105 )(where A 104may be C1-C 54 alkylene, and A 105 may be C6-C 59 aryl) - represented group, for example, C7-C 50 aralkyl, C7-C 40 aralkyl, C7-C 30 aralkyl, C7-C 20 aralkyl or C7-C 15 aralkyl, and as used herein the term "C2-C 60 heteroaralkyl" may be represented by -(A 106 )(A 107 )(wherein A 106 may be C1-C 59 alkylene, and A 107 may be C1-C 59 heteroaryl) - represented group, for example, C2-C 50 heteroaralkyl, C2-C 40 heteroaralkyl, C2-C 30 heteroaralkyl, C2-C 20 heteroaralkyl or C2-C 15 heteroaralkyl.
[0713] In the specification, the term "R 10a " may be:
[0714] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino or hydrazono;
[0715] 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;
[0716] 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
[0717] -Si(Q 31 )(Q 32 )(Q 33 )、 -N(Q 31 )(Q 32 )、 -B(Q 31 )(Q 32 )、 -P(Q 31 )(Q 32 )、 -C(=O)(Q 31 )、 -S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 )。
[0718] In the specification, groups Q1 to Q3, Q 11 to Q 13, Q 21 to Q 23 and Q 31 to Q 33 may each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; each unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof-substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group or C1-C 60 heterocyclic group; C7-C 60 aralkyl; or C2-C 60 heteroaralkyl.
[0719] As used herein, the term "heteroatom" may be any atom other than a carbon atom and a hydrogen atom. Examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se and any combination thereof.
[0720] As used herein, the term "first row transition metal" includes titanium (Ti), vanadium (V), cadmium (Cr) and / or manganese (Mn), etc., and the term "second row transition metal" as used herein includes yttrium (Y), zirconium (Zr), niobium (Nb) and / or molybdenum (Mo), etc., and the term "third row transition metal" as used herein may include Hf, Ta, W, Re, Os, Ir, Pt and Au, etc.
[0721] In the specification, the term "Ph" refers to phenyl, the term "Me" refers to methyl, the term "Et" refers to ethyl, "tert-Bu" and "Bu t " each refer to tert-butyl, and "OMe" refers to methoxy.
[0722] As used herein, the term "biphenyl" may be "phenyl substituted by phenyl". For example, "biphenyl" may be a substituted phenyl having a C6-C 60 aryl as a substituent.
[0723] As used herein, the term "terphenyl" may be "phenyl substituted by biphenyl". For example, "terphenyl" may be a substituted phenyl having a C6-C 60 aryl substituted by a C6-C 60 aryl as a substituent.
[0724] Unless otherwise defined, the symbols *, *' and *" as used herein each refer to a binding site to an adjacent atom in the corresponding formula or moiety.
[0725] 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 may be interpreted in a broader sense than the three axes in the aforementioned orthogonal coordinate system. For example, the x-axis, y-axis, and z-axis may describe axes that are orthogonal to each other, or may describe axes in different directions that are not orthogonal to each other.
[0726] Hereinafter, the compound according to the embodiment and the light-emitting device according to the embodiment will be described in detail with reference to the following synthesis examples and examples. The phrase "using B instead of A" used in describing the synthesis examples means using B instead of A with the same molar equivalent.
[0727] [Synthesis Examples and Examples]
[0728] Synthesis Example 1 (Compound 1)
[0729]
[0730] Synthesis of intermediate compound 1-a
[0731] Under argon atmosphere, N1,N3-bis([1,1':3',1"-terphenyl]-2'-yl)-5-(tert-butyl)-N1-(3-chlorophenyl)benzene-1,3-diamine (10 g, 13.5 mmol), 7-bromo-3-(tert-butyl)-17-phenyl-17l4,18l4-benzo[4,5]imidazo[3,2-a]indolizino[3',2',1':4,5]chromeno[4,3,2-cd]indoleplatin (10.3 g, 13.5 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (P(t-Bu)3) (1.6 mL, 3.8 mM) were added. mol) and sodium tert-butoxide (NatBuO) (11.5g, 120mmol) were added to a 2L flask and dissolved in 300mL of o-xylene. The reaction solution was stirred at 140°C for 2 hours. After the reaction solution was cooled, water (1L) and ethyl acetate (300mL) were added thereto to perform an extraction process. The organic layer thus collected was dried with MgSO4 and filtered. The filtrate was decompressed to remove the solvent, and the solid thus obtained was purified by column chromatography (by using silica gel using CH2Cl2 and hexane as a developing solvent) to obtain intermediate compound 1-a (white solid, 13.4g, 70%).
[0732] ESI-LCMS:[M] + :C 86 H 68 ClN5OPt.1416.4859.
[0733] Synthesis of intermediate compound 1-b
[0734] Under argon atmosphere, in 1L flask, intermediate compound 1-a (10g, 7mmol) was dissolved in 200mL of o-dichlorobenzene, and BBr (1.5 equivalents) was added thereto. The reaction solution was stirred at 140°C for 12 hours. After cooling the reaction solution, triethylamine was added thereto to terminate the reaction, and the resulting solution was decompressed to remove the solvent. The solid thus obtained was purified by column chromatography (by utilizing silica gel using CH2Cl2 and hexane as developing solvents), thereby obtaining intermediate compound 1-b (yellow solid, 2.5g, 25%).
[0735] ESI-LCMS:[M] + :C 86 H 65 BClN5OPt.1424.4641.
[0736] Synthesis of compound 1
[0737] Under argon atmosphere, intermediate compound 1-b (2g, 1.4mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.3g, 1.4mmol), Pd2dba3 (0.06g, 0.07mmol), tri-tert-butylphosphine (0.06mL, 0.14mmol) and sodium tert-butoxide (0.29g, 3mmol) were added to a 2L flask and dissolved in 30mL of o-xylene. The reaction solution was stirred at 140°C for 2 hours. After cooling the reaction solution, water (1L) and ethyl acetate (300mL) were added thereto to perform an extraction process. The organic layer thus collected was dried with MgSO4 and filtered. The filtrate was decompressed to remove the solvent, and the solid thus obtained was purified by column chromatography (by using silica gel using CH2Cl2 and hexane as developing solvents) to obtain compound 1 (yellow solid, 1.6g, 75%).
[0738] ESI-LCMS:[M] + :C 98 H 65 D8BN6OPt.1563.6117
[0739] 1H-NMR (CDCl3): d=8.57(d,1H),7.84(d,2H),7.74(s,1H),7.55(m,6H),7.43(s,4H),7.32(m,12H),7. 23(s,1H),7.18(m,3H),7.12(m,8H),7.05(t,1H),7.01(s,2H),6.95(m,4H),1.32(s,9H),1.22(s,9H)
[0740] Synthesis Example 2 (Compound 20)
[0741]
[0742] Synthesis of intermediate compound 20-a
[0743] Under argon atmosphere, N1,N3-di([1,1':3',1"-terphenyl]-2'-yl)-5-(tert-butyl)-N1-(3-chlorophenyl)benzene-1,3-diamine (10 g, 13.5 mmol), 2-iodo-5,5-diphenyl-5H-414,514,614-[1,2,5]diazaplatinum[2,3,4,5-lmn][1,10]phenanthroline (10.3 g, 13.5 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (1 1.5g, 120mmol) was added to a 2L flask and dissolved in 300mL of o-xylene. The reaction solution was stirred at 140°C for 2 hours. After the reaction solution was cooled, water (1L) and ethyl acetate (300mL) were added thereto to perform an extraction process. The organic layer thus collected was dried with MgSO4 and filtered. The filtrate was decompressed to remove the solvent, and the solid thus obtained was purified by column chromatography (using CH2Cl2 and hexane as the silica gel developing solvent) to obtain intermediate compound 20-a (white solid, 10.8g, 64%).
[0744] ESI-LCMS:[M] + :C 76 H 59 ClN4Pt.1257.5127
[0745] Synthesis of intermediate compound 20-b
[0746] Under argon atmosphere, in 1L flask, intermediate compound 20-a (10g, 8mmol) was dissolved in 200mL of o-dichlorobenzene, and BBr (1.5 equivalents) was added thereto. The reaction solution was stirred at 140 ° C for 12 hours. After cooling the reaction solution, triethylamine was added thereto to terminate the reaction, and the resulting solution was decompressed to remove the solvent. The solid thus obtained was purified by column chromatography (by utilizing silica gel using CH2Cl2 and hexane as developing solvents), so as to obtain intermediate compound 20-b (yellow solid, 1.6g, 19%).
[0747] ESI-LCMS:[M] + :C 76 H 56 BClN4Pt.1265.3992.
[0748] Synthesis of compound 20
[0749] Under argon atmosphere, intermediate compound 20-b (1.5 g, 1.2 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.27 g, 1.2 mmol), Pd2dba3 (0.06 g, 0.07 mmol), tri-tert-butylphosphine (0.06 mL, 0.14 mmol) and sodium tert-butoxide (0.29 g, 3 mmol) were added to a 2L flask and dissolved in 30 mL of o-xylene. The reaction solution was stirred at 140 ° C for 2 hours. After the reaction solution was cooled, water (1 L) and ethyl acetate (300 mL) were added thereto to perform an extraction process. The organic layer thus collected was dried with MgSO4 and filtered. The filtrate was decompressed to remove the solvent, and the solid thus obtained was purified by column chromatography (by using silica gel using CH2Cl2 and hexane as developing solvents) to obtain compound 20 (yellow solid, 1.2 g, 72%).
[0750] ESI-LCMS:[M] + :C 88 H 56 D8BN5Pt.1404.5434
[0751] 1 H-NMR (CDCl3): d=8.69(s,1H),8.61(d,1H),8.33(d,1H),8.20(d,4H),7.96(d,1H),7.85 (d,1H),7.59(d,1H),7.43(m,15H),7.28(m,11H),7.10(m,8H),7.08(s,2H),1.36(s,9H)
[0752] Synthesis Example 3 (Compound 25)
[0753]
[0754] Synthesis of intermediate compound 25-a
[0755] Under argon atmosphere, N1,N3-di([1,1':3',1"-terphenyl]-2'-yl)-5-(tert-butyl)-N1-(3-chlorophenyl)benzene-1,3-diamine (10 g, 13.5 mmol), 2-bromo-5-(1,3-diphenyl-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-2-yl)-5H-414,614-imidazo[1,5,4,3-lmn][1,10]phenanthroline gold complex (7.4 g, 13.5 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol) and sodium tert-butoxide (11.5g, 120mmol) are added in a 2L flask, and dissolved in 300mL of o-xylene. The reaction solution is stirred at 140°C for 2 hours. After cooling the reaction solution, water (1L) and ethyl acetate (300mL) are added thereto to perform an extraction process on it. The organic layer thus collected is dried with MgSO4, and filtered. The filtrate is decompressed to remove the solvent, and the solid thus obtained is purified by column chromatography (by utilizing the silica gel using CH2Cl2 and hexane as developing solvent), so as to obtain intermediate compound 25-a (white solid, 10.8g, 58%).
[0756] ESI-LCMS:[M] + C 81 H 62 AuClN8.1378.4545
[0757] Synthesis of intermediate compound 25-b
[0758] Under argon atmosphere, in 1L flask, intermediate compound 25-a (10g, 7.3mmol) was dissolved in 200mL of o-dichlorobenzene, and BBr3 (1.5 equivalents) was added thereto. The reaction solution was stirred at 140°C for 12 hours. After cooling the reaction solution, triethylamine was added thereto to terminate the reaction, and the resulting solution was decompressed to remove the solvent. The solid thus obtained was purified by column chromatography (by utilizing silica gel using CH2Cl2 and hexane as developing solvents), thereby obtaining intermediate compound 25-b (yellow solid, 1.4g, 14%).
[0759] ESI-LCMS:[M] + :C 81 H 59 AuBClN8.1386.4337.
[0760] Synthesis of compound 25
[0761] Under argon atmosphere, intermediate compound 25-b (1.4 g, 1 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.17 g, 1 mmol), Pd2dba3 (0.06 g, 0.07 mmol), tri-tert-butylphosphine (0.06 mL, 0.14 mmol) and sodium tert-butoxide (0.29 g, 3 mmol) were added to a 2 L flask and dissolved in 30 mL of o-xylene. The reaction solution was stirred at 140 ° C for 2 hours. After cooling the reaction solution, water (1 L) and ethyl acetate (300 mL) were added thereto to perform an extraction process. The organic layer thus collected was dried with MgSO4 and filtered. The filtrate was decompressed to remove the solvent, and the solid thus obtained was purified by column chromatography (by using silica gel using CH2Cl2 and hexane as developing solvents) to obtain compound 25 (yellow solid, 1.2 g, 78%).
[0762] ESI-LCMS:[M] + :C 93 H 59 D8AuBN9.1525.5818
[0763] 1 H-NMR (CDCl3): d=8.89(m,2H),8.50(d,1H),8.21(d,4H),7.99(d,1H),7.80(d,1H),7.63(t,2H),7.4 8(m,2H),7.40(m,22H),7.33(m,2H),7.23(s,1H),7.15(m,8H),7.09(m,2H),7.00(s,2H),1.36(s,9H)
[0764] Synthesis Example 4 (Compound 37)
[0765]
[0766] Synthesis of intermediate compound 37-a
[0767] Under argon atmosphere, N1,N3-bis([1,1':3',1"-terphenyl]-2'-yl)-5-(tert-butyl)-N1-(3-chlorophenyl)benzene-1,3-diamine (10 g, 13.5 mmol), 8-bromo-5-(1,5-dimethyl-1H-1,214,3-triazol-2-yl)-2-methyl-5-(114-pyridin-1-yl)-5H-614,1114-[1,2,3]triazolo[2',1':1,2][1,2,4]triazolo[4,5-a]pyridinepalladium (7.04 g, 13.5 mmol), PD2DBA3 (1.6 g, 1.9 mmol), tri-tert-butyl-N1-(3-chlorophenyl)benzene-1,3-diamine (10 g, 13.5 mmol), 8-bromo-5-(1,5-dimethyl-1H-1,214,3-triazol-2-yl)-2-methyl-5-(114-pyridin-1-yl)-5H-614,1114-[1,2,3]triazolo[2',1':1,2][1,2,4]triazolo[4,5-a]pyridinepalladium (7.04 g, 13.5 mmol), In 20% butyl phosphine (1.6mL, 3.8mmol) and sodium tert-butoxide (11.5g, 120mmol) are added in a 2L flask, and dissolved in 300mL of o-xylene. The reaction solution was stirred for 2 hours at 140°C. After the reaction solution was cooled, water (1L) and ethyl acetate (300mL) were added thereto to perform an extraction process thereon. The organic layer thus collected was dried with MgSO4, and filtered. The filtrate was decompressed to remove the solvent, and the solid thus obtained was purified by column chromatography (by utilizing CH2Cl2 and hexane as the silica gel of a developing solvent), so as to obtain intermediate compound 37-a (white solid, 9.8g, 62%).
[0768] ESI-LCMS:[M] + :C 69 H 61 C1N 10 Pd.1170.3872
[0769] Synthesis of intermediate compound 37-b
[0770] Under argon atmosphere, in 1L flask, intermediate compound 37-a (9.8g, 8.4mmol) was dissolved in 200mL of o-dichlorobenzene, and BBr (1.5 equivalents) was added thereto. The reaction solution was stirred at 140 ° C for 12 hours. After cooling the reaction solution, triethylamine was added thereto to terminate the reaction, and the resulting solution was decompressed to remove the solvent. The solid thus obtained was purified by column chromatography (by utilizing silica gel using CH2Cl2 and hexane as developing solvents), so as to obtain intermediate compound 37-b (yellow solid, 2.16g, 22%).
[0771] ESI-LCMS:[M] + :C 69 H 58 BCN 10 Pd.1178.3783.
[0772] Synthesis of compound 37
[0773] Under argon atmosphere, intermediate compound 37-b (2g, 1.7mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.3g, 1.7mmol), pd2dba3 (0.06g, 0.07mmol), tri-tert-butylphosphine (0.06mL, 0.14mmol) and sodium tert-butoxide (0.29g, 3mmol) were added to a 2L flask and dissolved in 30mL of o-xylene. The reaction solution was stirred at 140°C for 2 hours. After cooling the reaction solution, water (1L) and ethyl acetate (300mL) were added thereto to perform an extraction process on it. The organic layer thus collected was dried with MgSO4 and filtered. The filtrate was decompressed to remove the solvent, and the solid thus obtained was purified by column chromatography (by using silica gel using CH2Cl2 and hexane as developing solvents) to obtain compound 37 (yellow solid, 1.56g, 70%).
[0774] ESI-LCMS:[M] + :C 81 H 58 D8B 11 Pd.1317.5117
[0775] 1 H-NMR (CDCl3): d=8.98(m,1H),8.59(d,2H),8.46(s,1H),8.30(s,1H),8.11(d,4H),7.84(m,2H),7.43 (m,14H),7.35(m,4H),7.23(s,1H),7.13(m,12H),7.06(s,2H),3.78(s,3H),2.42(s,6H),1.33(s,9H)
[0776] The synthesis methods of compounds other than the compounds of Synthesis Examples 1 to 4 can be easily recognized by those skilled in the art by referring to the synthesis routes and raw materials.
[0777] Evaluation Example 1
[0778] For the compounds of Synthesis Examples and Comparative Examples, the HOMO energy level and the absorption wavelength (λ Abs ), emission wavelength (λ emi ), anti-system crossing rate (k risc ) and delayed fluorescence lifetime (τD), and the results are shown in Table 1.
[0779] The λ was measured by using the Labsolution UV-Vis software using a UV-1800 UV / Visible scanning spectrophotometer manufactured by SHIMADZU. Abs, the spectrophotometer is equipped with a deuterium / tungsten-halogen light source and a silicon photodiode. By using the FluorEssence software of the fluoromax+ spectrophotometer manufactured by HORIBA to measure λ emi , the spectrophotometer is equipped with a xenon light source and a monochromator. By using the SmartManager software of the SP2 electrochemical workstation manufactured by ZIVE LAB to measure the HOMO energy level. By using the PLQY measurement software of the Quantaurus-QY AbsolutePL quantum yield spectrophotometer manufactured by Hamamatsu to measure k risc , the spectrophotometer is equipped with a xenon light source, a monochromator, a photon multi-channel analyzer, and an integrating sphere. By using the fluorescence lifetime spectrophotometer (C11367-01) manufactured by Hamamatsu to measure τD, that is, the delayed fluorescence lifetime, at 300K.
[0780] [Table 1]
[0781]
[0782]
[0783] Example 1
[0784] As the anode, a glass substrate (product of Corning Inc.) with a 15 Ω / cm 2 ITO electrode formed thereon was cut into a size of 50 mm x 50 mm x 0.7 mm, cleaned by ultrasonic treatment in isopropyl alcohol and pure water for 5 minutes each, irradiated with ultraviolet light, and exposed to ozone for 30 minutes, and then installed on a vacuum deposition apparatus.
[0785] NPD was deposited on the anode to form a hole injection layer with a thickness, compound HT6 was deposited on the hole injection layer to form a hole transport layer with a thickness, and CzSi was deposited on the hole transport layer to form an electron blocking layer with a thickness.
[0786] A host mixture in which compound HTH53 and compound ETH66 were mixed at a weight ratio of 1:1, compound PD33 and compound 1 were co-deposited on the electron blocking layer at a weight ratio of 85:14:1 to form an emission layer with a thickness. Compound TSPO1 was deposited on the emission layer to form a hole blocking layer with a thickness. Compound TPBi was deposited on the hole blocking layer to form an electron transport layer with a thickness, and LiF was deposited on the electron transport layer to form a an electron injection layer having a thickness. Formed using Al to have a LiF / Al electrode (cathode) having a thickness. Formed using compound HT28 thereon to have a capping layer having a thickness, thereby preparing a light-emitting device. Each layer is formed by vacuum deposition.
[0787] Examples 2 to 4 and Comparative Examples 1 to 5
[0788] The light-emitting devices of Examples 2 to 4 and Comparative Examples 1 to 5 were each manufactured in substantially the same manner as in Example 1, except that when forming the emission layer, compound 20, compound 25, compound 37, and Comparative Example compounds A to E were each used instead of compound 1.
[0789]
[0790] Evaluation Example 2
[0791] To evaluate the characteristics of the light-emitting devices manufactured according to Examples 1 to 4 and Comparative Examples 1 to 5, the driving voltage, top emission efficiency, and device lifetime were measured at a current density of 10 mA / cm 2 and the results are shown in Table 2. The driving voltage and top emission efficiency of the light-emitting devices were measured using a V7000 OLED IVL test system (Polaronix). To evaluate the device lifetime, a value obtained by comparing the time taken to reach 95% of the initial luminance in Comparative Example 1 with the time measured in each of Examples 1 to 4 and Comparative Examples 2 to 5 was calculated.
[0792] [Table 2]
[0793]
[0794]
[0795]
[0796] Referring to Table 2, the light-emitting devices of Examples 1 to 4 exhibited a lower driving voltage, a higher top emission efficiency, and a longer device lifetime compared to Comparative Examples 1 to 5, generally showing better device characteristics.
[0797] According to the embodiment, the use of the polycyclic compound represented by Formula 1 can ensure the manufacture of a light-emitting device having high luminous efficiency and long lifetime, as well as high-quality electronic devices and electronic appliances including the light-emitting device.
[0798] Embodiments have been disclosed herein, and although terms are employed, they are used and interpreted in a general and descriptive sense only and not for purposes of limitation. In some instances, 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 singly or in combination with features, characteristics and / or elements described in connection with other embodiments, unless specifically indicated otherwise. 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; A laminate between the first electrode and the second electrode and including an emission layer; And A polycyclic compound represented by Formula 1: Formula 1 Wherein in Formula 1, Ar0 is a group represented by Formula 2, Formula 2 Wherein in Formula 1 and Formula 2, CY1 to CY3 are each independently a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group, W1 is a single bond, O, S, N(R4), N(Ar1), C(R4)(R5) or Si(R4)(R5), W2 is a single bond, O, S, N(R6), N(Ar2), C(R6)(R7) or Si(R6)(R7), a1 and a2 are each independently 0 or 1, When a1 is 0, *-(W1) a1 -*' does not exist, When a2 is 0, *-(W2) a2 -*' does not exist, The sum of a1 and a2 is 1 or greater, Ar1 and Ar2 are each independently a group represented by Formula 2, The * in Formula 2 indicates the binding site to the adjacent nitrogen atom, R1 to R3 are each independently 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) or M(L1) n1 (L2) n2 , wherein at least one of R1 to R3 is independently M(L1) n1 (L2) n2 , M is a transition metal, L1 and L2 are each independently a monodentate ligand, bidentate ligand, tridentate ligand, tetradentate ligand, pentadentate ligand or hexadentate ligand, n1 is an integer selected from 0 to 6, n2 is an integer selected from 0 to 6, When n1 is 2 or greater, two or more L1s are the same or different from each other, When n2 is 2 or greater, two or more L2s are the same or different from each other, The sum of n1 and n2 is 1 or greater, b1 to b3 are each independently an integer selected from 1 to 10, b21 and b23 are each independently an integer selected from 1 to 5, b22 is an integer selected from 1 to 3, When b1 is 2 or greater, two or more R1s are the same or different from each other, When b2 is 2 or greater, two or more R2s are the same or different from each other, When b3 is 2 or greater, two or more R3s are the same or different from each other, When b21 is 2 or greater, two or more Rs 21 are the same as or different from each other, When b22 is 2 or greater, two or more Rs 22 are the same as or different from each other, When b23 is 2 or greater, two or more Rs 23 are the same as or different from each other, Two or more of the plurality of R1 are connected to or combined with each other through a first linking group to form a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group, Two or more of the plurality of R2 are connected to or combined with each other through a first linking group to form a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group, Two or more of the plurality of R3 are connected or bonded to each other through a first linking group to form a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group, The first linking group is a single bond, a double bond, *-O-*, *-S-*, *-C(=O)-*, *-S(=O)-*, *-C(R8)(R9)-*, *-C(R8)=C(R9)-*, *-C(R8)=*, *-Si(R8)(R9)-*, *-B(R8)-*, *-N(R8)-*, *-P(R8)-*, C3-C 30 carbocyclic group or C1-C 30 heterocyclic group, R4 to R9 and R 21 to R 23 are each independently 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), R 10a is: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino or hydrazono; 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; 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 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; each unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group or C1-C 60 heterocyclic group; C7-C 60 aralkyl; or C2-C 60 heteroaralkyl.
2. The light-emitting device according to claim 1, wherein: The first electrode is an anode, The second electrode is a cathode, The laminate further includes: A hole transport region between the first electrode and the emission layer; and An electron transport region between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer or any combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer or any combination thereof.
3. The light-emitting device according to claim 1, wherein the laminate includes the polycyclic compound represented by Formula 1.
4. The light-emitting device according to claim 1, wherein the emission layer includes the polycyclic compound represented by Formula 1.
5. The light-emitting device according to claim 1, wherein: The emission layer includes a host and a dopant, and The dopant includes the polycyclic compound represented by Formula 1.
6. An electronic device, comprising the light-emitting device according to any one of claims 1 to 5.
7. The electronic device according to claim 6, further comprising: A color filter, a color conversion layer, a touch screen layer, a polarization layer or any combination thereof.
8. An electronic apparatus, comprising the light-emitting device according to any one of claims 1 to 5.
9. The electronic device according to claim 8, wherein the electronic device is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a 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 having a plurality of displays tiled together, a theater screen, a stadium screen, a light therapy device, or a signboard.
10. A polycyclic compound represented by Formula 1: Formula 1 Wherein in Formula 1, Ar0 is a group represented by Formula 2, Formula 2 Wherein in Formulas 1 and 2, CY1 to CY3 are each independently a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group, W1 is a single bond, O, S, N(R4), N(Ar1), C(R4)(R5), or Si(R4)(R5), W2 is a single bond, O, S, N(R6), N(Ar2), C(R6)(R7), or Si(R6)(R7), a1 and a2 are each independently 0 or 1, When a1 is 0, *-(W1) a1 -*' does not exist, When a2 is 0, *-(W2) a2 -*' does not exist The sum of a1 and a2 is 1 or greater, Ar1 and Ar2 are each independently a group represented by Formula 2, The * in Formula 2 indicates the binding site to the adjacent nitrogen atom, R1 to R3 are each independently 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) or M(L1) n1 (L2) n2 , wherein at least one of R1 to R3 is independently M(L1) n1 (L2) n2 , M is a transition metal, L1 and L2 are each independently a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, or a hexadentate ligand, n1 is an integer selected from 0 to 6, n2 is an integer selected from 0 to 6, When n1 is 2 or greater, two or more L1s are the same or different from each other, When n2 is 2 or greater, two or more L2s are the same or different from each other, The sum of n1 and n2 is 1 or greater, b1 to b3 are each independently an integer selected from 1 to 10, b21 and b23 are each independently an integer selected from 1 to 5, b22 is an integer selected from 1 to 3, When b1 is 2 or greater, two or more R1s are the same or different from each other, When b2 is 2 or greater, two or more R2s are the same or different from each other, When b3 is 2 or greater, two or more R3s are the same or different from each other, When b21 is 2 or greater, two or more Rs 21 are the same as or different from each other, When b22 is 2 or greater, two or more Rs 22 are the same as or different from each other, When b23 is 2 or greater, two or more Rs 23 are the same as or different from each other, Two or more of the plurality of R1s are connected to or combined with each other through a first linking group to form a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group, Two or more of the plurality of R2s are connected to or combined with each other through a first linking group to form a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group, Two or more of the plurality of R3 are connected or bonded to each other through a first linking group to form a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group, The first linking group is a single bond, a double bond, *-O-*, *-S-*, *-C(=O)-*, *-S(=O)-*, *-C(R8)(R9)-*, *-C(R8)=C(R9)-*, *-C(R8)=*, *-Si(R8)(R9)-*, *-B(R8)-*, *-N(R8)-*, *-P(R8)-*, C3-C 30 carbocyclic group or C1-C 30 heterocyclic group, R4 to R9 and R 21 to R 23 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), R 10a is: Deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazino, or hydrazono; 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; Each unsubstituted or substituted with the following 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 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 each independently is: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; each unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group or C1-C 60 heterocyclic group; C7-C 60 aralkyl; or C2-C 60 heteroaralkyl.
11. The polycyclic compound according to claim 10, wherein the polycyclic compound represented by Formula 1 includes at least one deuterium.
12. The polycyclic compound according to claim 10, wherein each of CY1 to CY3 is independently cyclopentadienyl, adamantyl, norbornyl, phenyl, pentaphenylenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, perylenyl, pentaphenyl, heptaphenylenyl, tetracenyl, picenyl, hexacenyl, rubicenyl, coronenyl, ovalenyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenoanthryl, indenoacenaphthylenyl, pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthylindolyl, isoindolyl, benzisoindolyl, naphthylisoindolyl, benzosilolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuryl, indacarbazolyl, 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 or azadibenzofuryl.
13. The polycyclic compound according to claim 10, wherein: The sum of a1 and a2 is 1, W1 is N(Ar1), and W2 is N(Ar2).
14. The polycyclic compound according to claim 10, wherein M is platinum, palladium, cobalt, gold, iridium, rhenium, nickel, silver or copper.
15. The polycyclic compound according to claim 10, wherein: L1 is a group represented by one of Formula 3A to Formula 3E, and L2 is *1-F, *1-Cl, *1-Br, *1-I, *1-C(R 41 )(R 42 )(R 43 ), *1-O(R 41 ), or a group represented by one of Formula 4A to Formula 4F: wherein in Formula 3A to Formula 3E and Formula 4A to Formula 4F, *1, *2, *3 and *4 each indicate a binding site to M, Y 31 to Y 34 each independently represents a single bond, *-O-*', *-S-*', *-C(R 35 )(R 36 )-*', *-Si(R 35 )(R 36 )-*', *-B(R 35 )-*', *-N(R 35 )-*' or *-P(R 35 )-*', Z 41 and Z 42 each independently represents a single bond, *-O-*', *-S-*', *-B(R 44 )-*', *-N(R 44 )-*' or *-P(R 44 )-*', A 31 to A 34 and A 41 each independently is 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, a31 to a34 and d41 are each independently an integer selected from 1 to 3, T 31 to T 34 each independently represents a single bond, a double bond, *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', *-C(R 37 )(R 38 )-*', *-C(R 37 )=C(R 38 )-*', *-C(R 37 )=*', *-Si(R 37 )(R 38 )-*', *-B(R 37 )-*', *-N(R 37 )-*' or *-P(R 37 )-*', U 41 and U 42 each independently is *-O-*, *-S-*, *-C(=O)-*, *-S(=O)-*, *-C(R 45 )(R 46 )-*, *-C(R 45 )=C(R 46 )-*, *-C(R 45 )=*, *-Si(R 45 )(R 46 )-*, *-B(R 45 )-*, *-N(R 45 )-* or *-P(R 45 )-*, X is C, P or As, b31 to b34 are each independently an integer selected from 0 to 10, R 31 to R 38 and R 41 to R 46 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), R 10a is: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino or hydrazonyl; 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; Each unsubstituted or substituted by the following 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 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ) and Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 each independently is: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; each unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof-substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group or C1-C 60 heterocyclic group; C7-C 60 aralkyl; or C2-C 60 heteroaralkyl.
16. The polycyclic compound according to claim 15, wherein: n1 is 0 and n2 is 2; n1 is 1 and n2 is 0; n1 is 1 and n2 is 1; n1 is 1 and n2 is 2; n1 is 2 and n2 is 0; or n1 is 3 and n2 is 0.
17. The polycyclic compound according to claim 10, wherein the polycyclic compound represented by Formula 1 is represented by one of Formula 1A-1 to Formula 1A-11, Formula 1B-1 to Formula 1B-3, and Formula 1C-1: Wherein in Formula 1A-1 to Formula 1A-11, Formula 1B-1 to Formula 1B-3, and Formula 1C-1, Ar0, CY2, CY3, W2, a2, R2, R3, b2, and b3 are the same as those defined in Formula 1, M1 is platinum, palladium, cobalt, gold, iridium, rhenium, nickel, silver, or copper, M2 is gold, nickel, silver, or copper, M3 is iridium or rhenium, X1 to X6 are each independently C or N, X 51 and X 52 each independently is C, P or As, Y 51 to Y 56 each independently represents a single bond, *-O-*', *-S-*', *-C(R 57 )(R 58 )-*', *-Si(R 57 )(R 58 )-*', *-B(R 57 )-*', *-N(R 57 )-*' or *-P(R 57 )-*', A 51 to A 53 、A 55 and A 56 each independently is 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, T 51 to T 54 each independently represents a single bond, a double bond, *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', *-C(R 59 )(R 60 )-*', *-C(R 59 )=C(R 60 )-*', *-C(R 59 )=*', *-Si(R 59 )(R 60 )-*', *-B(R 59 )-*', *-N(R 59 )-*' or *-P(R 59 )-*', Z 51 to Z 54 each independently represents a single bond, *-O-*', *-S-*', *-B(R 61 )-*', *-N(R 61 )-*' or *-P(R 61 )-*', U 51 and U 52 each independently is *-O-*, *-S-*, *-C(=O)-*, *-S(=O)-*, *-C(R 62 )(R 63 )-*, *-C(R 62 )=C(R 63 )-*, *-C(R 62 )=*, *-Si(R 62 )(R 63 )-*, *-B(R 62 )-*, *-N(R 62 )-* or *-P(R 62 )-*, a51 to a54 are each independently an integer selected from 1 to 3, b51 to b53, b55, and b56 are each independently an integer selected from 0 to 10, d51 and d52 are each independently an integer selected from 1 to 3, and R 51 to R 63 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, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2).
18. The polycyclic compound according to claim 10, wherein at least one of R1 to R3 is each independently deuterium, -F, cyano, tert-butyl, carbazolyl, or any combination thereof.
19. The fused-ring compound according to claim 10, wherein R4 to R9 and R 21 to R 23 are each independently: Hydrogen, deuterium, -F, or cyano; Unsubstituted or substituted C1-C 20 alkyl: deuterium, -F, cyano, or any combination thereof; or Each unsubstituted or substituted phenyl, naphthyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, azadibenzofuranyl, azadibenzothiophenyl or azacarbazolyl group: deuterium, -F, cyano, C1-C 20 alkyl, deuterated C1-C 20 alkyl, fluorinated C1-C 20 alkyl, phenyl, deuterated phenyl, fluorinated phenyl, (C1-C 20 alkyl)phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorene, dibenzosilolyl or any combination thereof.
20. The polycyclic compound according to claim 10, wherein the polycyclic compound represented by Formula 1 is one of Compound 1 to Compound 40:
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KR1020240008281A