Light-emitting element, fused polycyclic compound for light-emitting element, and display device including light-emitting element
By using an emission layer composed of a specific fused polycyclic compound in the organic electroluminescent light emitting element, the problem of insufficient luminescence efficiency and service life in the prior art is solved, and more efficient luminescence and longer service life are achieved.
Patent Information
- Application Number
- CN202411826376.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-12-14
- Filing Date
- 2024-12-12
- Publication Date
- 2025-06-17
AI Technical Summary
The luminescence efficiency and service life of the existing organic electroluminescent light emitting elements are insufficient, making it difficult to achieve stable improvement.
The emission layer composed of specific fused polycyclic compounds is used to improve luminous efficiency and extend the service life of the component through its unique chemical structure and electronic state.
It significantly improves the luminous efficiency and component service life, and improves the overall performance of the display device.
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Figure CN120157692A_ABST
Abstract
Description
[0001] Cross - reference to related applications
[0002] This application claims the priority and benefit of Korean Patent Application No. 10 - 2023 - 0181640, filed with the Korean Intellectual Property Office on December 14, 2023, the entire contents of which are incorporated herein by reference. Technical field
[0003] One or more embodiments of the present disclosure relate to a light - emitting element, a fused polycyclic compound for a light - emitting element, and a display device including the light - emitting element. Background art
[0004] Recently, an organic electroluminescent display device as an image display device has been actively researched and developed. Different from a liquid crystal display device and the like, an organic electroluminescent display device is a self - emitting type or kind of display device, which recombines holes and electrons in an emission layer injected from a first electrode and a second electrode of the organic electroluminescent display device, respectively, and thus uses a light - emitting material (light - emitting dopant) in the emission layer to emit light to achieve display (e.g., display of an image).
[0005] When applying an organic electroluminescent light - emitting element to a display device, improvement in the luminous efficiency (e.g., high luminous efficiency) and the element service life (e.g., long element service life) of the organic electroluminescent light - emitting element is desired or required, and thus, the development of materials for an organic electroluminescent light - emitting element that can stably achieve such improvement has been continuously desired or pursued.
[0006] For example, recently, in order to realize an organic electroluminescent light - emitting element having high luminous efficiency, technologies based on phosphorescence using triplet energy levels or fluorescence emission using triplet - triplet annihilation (TTA), which is a phenomenon of generating singlet excitons by the collision of triplet excitons, have been actively developed or pursued, and the development of thermally activated delayed fluorescence (TADF) materials using the delayed fluorescence phenomenon has been carried out or pursued. Summary of the invention
[0007] One or more aspects of embodiments of the present disclosure relate to a light - emitting element having improved luminous efficiency and element service life.
[0008] One or more aspects of embodiments of the present disclosure relate to a fused polycyclic compound capable of improving the luminous efficiency and element service life of a light - emitting element including the fused polycyclic compound.
[0009] One or more aspects of embodiments of the present disclosure relate to a display device having excellent or appropriate display quality by including a light - emitting element having improved luminous efficiency and element service life.
[0010] Other aspects will be set forth in part in the following description, and in part will be obvious from the description, or can be learned by practice of the presented embodiments.
[0011] According to one or more embodiments of the present disclosure, a light-emitting element includes a first electrode, a second electrode facing the first electrode (e.g., opposite to the first electrode), and an emission layer between the first electrode and the second electrode, wherein the emission layer includes a fused polycyclic compound represented by Formula 1 as a first compound (first dopant).
[0012] Formula 1
[0013]
[0014] In Formula 1, X may be a direct bond, O, S, Se, CR 31 R 32 , PR 33 , SiR 34 R 35 , C═O, C═S or NR 36 , Z may be a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and R1 to R8, R a to R k and R 31 to R 36 may each independently be hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may be bonded to an adjacent group to form a ring, and if (e.g., when) any one selected from R1 to R8, R a to R k and R 31 to R 36 is bonded to an adjacent group to form a ring, the formed ring may not (e.g., does not) include two consecutive sp 3 hybridized carbons bonded to each other, and if (e.g., when) Z is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, then R5 may not be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
[0015] In one or more embodiments, the first compound represented by Formula 1 can be represented by any one selected from Formulas 2-1 to 2-8.
[0016] Formula 2-1
[0017]
[0018] Formula 2-2
[0019]
[0020] Formula 2-3
[0021]
[0022] Formula 2-4
[0023]
[0024] Formula 2-5
[0025]
[0026] Formula 2-6
[0027]
[0028] Formula 2-7
[0029]
[0030] Formula 2-8
[0031]
[0032] In Formulas 2-1 to 2-8, R9 to R 19 can each independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, Y1 and Y2 can each independently be O or S, n9 can be an integer selected from 0 to 5, n14 to n18 can each independently be an integer selected from 0 to 4, and n19 can be an integer selected from 0 to 3.
[0033] In Formulas 2-1 to 2-8, X, R1 to R8, R a to R k and R 31 to R 36 can each independently be the same as defined in Formula 1.
[0034] In one or more embodiments, the first compound represented by Formula 1 can be represented by Formula 3-1 or Formula 3-2.
[0035] Formula 3-1
[0036]
[0037] Formula 3-2
[0038]
[0039] In Formula 3-1 and Formula 3-2, A1 can be hydrogen, deuterium, a substituted or unsubstituted oxy group, or a substituted or unsubstituted amino group, A2 can be hydrogen, deuterium, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R m can be hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and m can be an integer selected from 0 to 4.
[0040] In Formula 3-1 and Formula 3-2, the same descriptions as defined in Formula 1 can apply to X, Z, R2 to R8, R a to R k and R 31 to R 36 .
[0041] In one or more embodiments, Z and A2 can be the same.
[0042] In one or more embodiments, the first compound represented by Formula 1 can be represented by any one selected from Formula 4-1 to Formula 4-4.
[0043] Formula 4-1
[0044]
[0045] Formula 4-1
[0046]
[0047] Formula 4-3
[0048]
[0049] Formula 4-4
[0050]
[0051] In Formula 4-1 to Formula 4-4, X1 to X5 can each independently be O, S, CR 26 R 27 or NR28 , R a1 to R k1 and R 20 to R 28 may each independently be hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may be bonded to an adjacent group to form a ring, n20 and n23 to n25 may each independently be an integer selected from 0 to 4, and n21 and n22 may each independently be an integer selected from 0 to 3.
[0052] In Formulas 4-1 to 4-4, the same descriptions as defined in Formula 1 apply to X, Z, R1 to R8, and R 31 to R 36 .
[0053] In one or more embodiments, the first compound represented by Formula 1 may be represented by Formula 5.
[0054] Formula 5
[0055]
[0056] In Formula 5, R x may be hydrogen, deuterium, a halogen, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may be bonded to an adjacent group to form a ring, and nx may be an integer selected from 0 to 5.
[0057] In Formula 5, the same descriptions as defined in Formula 1 apply to Z, R1 to R8, and R a to R k .
[0058] In one or more embodiments, the first compound represented by Formula 1 may be represented by Formula 6.
[0059] Formula 6
[0060]
[0061] In Formula 6, Z1 and Z2 can each independently be a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and R 41 to R 48 can each independently be hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or can bond with an adjacent group to form a ring.
[0062] In Formula 6, the same descriptions as defined in Formula 1 can apply to R1 to R8 and R a to R k .
[0063] In one or more embodiments, in Formula 6, R1 and R 41 can each independently be hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenoxy group, or a substituted or unsubstituted diphenylamino group.
[0064] In one or more embodiments, the first compound represented by Formula 1 can be represented by any one selected from Formulas 7-1 to 7-4.
[0065] Formula 7-1
[0066]
[0067] Formula 7-2
[0068]
[0069] Formula 7-3
[0070]
[0071] Formula 7-4
[0072]
[0073] In Formulas 7-1 to 7-4, A can be hydrogen or deuterium, R x1 , R x2 , R y1 and R y2may each independently be deuterium, a halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and R x3 , R x4 , R y3 and R y4 may each independently be deuterium, a halogen, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may be bonded to an adjacent group to form a ring.
[0074] In Formulas 7-1 to 7-4, the same descriptions as defined in Formula 1 apply to X, Z, R1 to R8, R a to R c and R 31 to R 36 .
[0075] In one or more embodiments, the first compound represented by Formula 1 may be represented by Formula 8-1 or Formula 8-2.
[0076] Formula 8-1
[0077]
[0078] Formula 8-2
[0079]
[0080] In Formulas 8-1 and 8-2, A may be hydrogen or deuterium, and R z may be deuterium, a halogen, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
[0081] In Formulas 8-1 and 8-2, the same descriptions as defined in Formula 1 apply to X, Z, R1 to R8, R d to R k and R 31 to R 36 .
[0082] In one or more embodiments, the emissive layer further comprises at least one selected from a second compound represented by formula HT-1, a third compound represented by formula ET-1, and a fourth compound represented by formula D-1.
[0083] Formula HT-1
[0084]
[0085] In formula HT-1, M1 to M8 may each independently be N or CR 51 , L1 may be a direct bond, a substituted or unsubstituted arylene having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene having 2 to 30 ring carbon atoms, Y a may be a direct bond, CR 52 R 53 or SiR 54 R 55 , Ar a may be a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and R 51 to R 55 may each independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thio, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boryl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 60 ring carbon atoms or substituted or unsubstituted heteroaryl having 2 to 60 ring carbon atoms, and / or may be bonded to an adjacent group to form a ring.
[0086] Formula ET-1
[0087]
[0088] In formula ET-1, at least one selected from Z a to Z c is N, and the remaining groups may be CR 56 , R 56 may be hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 60 ring carbon atoms or substituted or unsubstituted heteroaryl having 2 to 60 ring carbon atoms, b1 to b3 may each independently be an integer selected from 0 to 10, Ar b to Ar dEach of them can be independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and L2 to L4 can each be independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0089] Formula D-1
[0090]
[0091] In Formula D-1, Q1 to Q4 can each be independently C or N, C1 to C4 can each be independently a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms, L 11 to L 13 can each be independently a direct bond, *—O—*, *—S—*, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In L 11 to L 13 “-*” refers to the part connected to C1 to C4, b11 to b13 can each be independently 0 or 1, R 61 to R 66 can each be independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms. One or more selected from R 61 to R 66 can be independently bonded to adjacent groups to form a ring, and d1 to d4 can each be independently an integer selected from 0 to 4.
[0092] In one or more embodiments of the present disclosure, the display device includes a base layer, a circuit layer on the base layer, and a display device layer on the circuit layer and including a light-emitting element. The light-emitting element includes a first electrode, a second electrode facing the first electrode, and an emission layer between the first electrode and the second electrode and including a fused polycyclic compound represented by Formula 1 as the first compound.
[0093] In one or more embodiments, the light-emitting element may further include a capping layer on the second electrode, and for light in a wavelength range of about 550 nanometers (nm) to about 660 nm, the refractive index of the capping layer is about 1.6 or greater.
[0094] In one or more embodiments, the display device may further include a light control layer on the display device layer and including quantum dots. The light-emitting element may emit first color light, and the light control layer may include: a first light control component including first quantum dots that convert the first color light into second color light having a wavelength longer than that of the first color light; a second light control component including second quantum dots that convert the first color light into third color light having a wavelength longer than that of each of the first color light and the second color light; and a third light control component that transmits the first color light.
[0095] In one or more embodiments, the display device may further include a color filter layer. The color filter layer may include a first color filter configured to transmit the second color light, a second color filter configured to transmit the third color light, and a third color filter configured to transmit the first color light.
[0096] In one or more embodiments of the present disclosure, a fused polycyclic compound represented by Formula 1 is provided. BRIEF DESCRIPTION OF THE DRAWINGS
[0097] The accompanying drawings are included to provide a further understanding of the present disclosure, and are incorporated in and constitute a part of this disclosure. The drawings illustrate example embodiments of the present disclosure and, together with the description, are used to explain the principles of the present disclosure. The above and / or other aspects of the present disclosure should become apparent and understandable by the following description of the embodiments in conjunction with the accompanying drawings. In the drawings:
[0098] Figure 1 is a plan view of a display device according to one or more embodiments of the present disclosure;
[0099] Figure 2 is a cross-sectional view of a display device according to one or more embodiments of the present disclosure;
[0100] Figure 3 is a cross-sectional view schematically illustrating a light-emitting element according to one or more embodiments of the present disclosure;
[0101] Figure 4 is a cross-sectional view schematically illustrating a light-emitting element according to one or more embodiments of the present disclosure;
[0102] Figure 5 is a cross-sectional view schematically illustrating a light-emitting element according to one or more embodiments of the present disclosure;
[0103] Figure 6 A cross-sectional view of a light-emitting element according to one or more embodiments of the present disclosure for illustrative explanation;
[0104] Figure 7 and Figure 8 Each is a cross-sectional view of a display device according to one or more embodiments of the present disclosure;
[0105] Figure 9 A cross-sectional view of a display device according to one or more embodiments of the present disclosure for explanation;
[0106] Figure 10 A cross-sectional view of a display device according to one or more embodiments of the present disclosure for explanation; and
[0107] Figure 11 A view of a vehicle in which a display device according to one or more embodiments of the present disclosure is arranged. Detailed Embodiments
[0108] The present disclosure can be modified in one or more suitable ways and has various forms, and thus specific embodiments / example embodiments will be illustrated in the drawings and described in more detail in the detailed description of the present disclosure. However, it should be understood that it is not intended to limit the present disclosure to the specific forms disclosed, but is intended to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the present disclosure.
[0109] When interpreting each of the drawings, the same reference numerals are used to refer to the same elements. In the accompanying drawings, for the clarity of the present disclosure, the dimensions of each structure may be exaggeratedly illustrated. It will be understood that although terms such as "first" and / or "second" etc. may be used herein to describe one or more suitable components, these components should not be limited by these terms. These terms are only used to distinguish one component from another. For example, without departing from the scope of the example embodiments of the present disclosure, the first component may be referred to as the second component, and similarly, the second component may be referred to as the first component. As used herein, the singular forms "a", "an", and "the" are also intended to include the plural forms unless the context clearly indicates otherwise. Further, when describing the embodiments of the present disclosure, the use of "may" refers to "one or more embodiments of the present disclosure".
[0110] In the present disclosure, it will be understood that the terms "comprise / comprising", "include / including", and / or "have / has / having" are intended to indicate the presence of a feature, quantity, step, operation, component, part, and / or one or more (e.g., any suitable) combinations thereof disclosed in the present specification, but do not exclude the presence or addition of one or more other features, quantities, steps, operations, components, parts, and / or one or more (e.g., any suitable) combinations thereof. As used herein, the terms "and", "or", and "and / or" may include any and all combinations of one or more of the associated listed items. When used before / after a list of elements, expressions such as "at least one of", "one of", and "selected from" modify the entire list of elements, rather than individual elements of the list. For example, "at least one of a, b, and c", "at least one selected from a, b, and c", "at least one selected from a to c", etc. may indicate only a, only b, only c, both a and b (e.g., simultaneously), both a and c (e.g., simultaneously), both b and c (e.g., simultaneously), all of a, b, and c, or variants thereof. Depending on the context, " / " used herein may be interpreted as "and" or "or".
[0111] In the present disclosure, if (e.g., when) a layer, film, region, or plate is referred to as being "on" or "in an upper portion of" another layer, film, region, or plate, it may not only be "directly on" the layer, film, region, or plate, but there may also be one or more intervening layers, films, regions, or plates. In contrast, if (e.g., when) a layer, film, region, or plate is referred to as being "under" or "in a lower portion of" another layer, film, region, or plate, it may not only be directly below the layer, film, region, or plate, but there may also be one or more intervening layers, films, regions, or plates. Additionally, it will be understood that if (e.g., when) a part is referred to as being "on" another part, it may be disposed above the other part, or may also be disposed below the other part. In the present disclosure, "directly on" may mean that there are no additional layers, films, regions, plates, etc. between a layer, film, region, plate, etc. and other parts. For example, "directly on" may mean that two layers or two members are provided without using another member (such as an adhesive member) therebetween.
[0112] In the present disclosure, the term "substituted or unsubstituted" may refer to being substituted or unsubstituted by at least one substituent selected from the group consisting of deuterium, halogen, cyano, nitro, amino, amine group, silyl group, oxy group, thio group, sulfinyl group, sulfonyl group, carbonyl group, boron group, phosphinyl group, phosphinyl sulfide group, alkyl group, alkenyl group, alkynyl group, hydrocarbon ring group, aryl group, and heterocyclic group. Additionally, each of the substituents exemplified above may be substituted or unsubstituted. For example, biphenyl may be interpreted as an aryl group or a phenyl group substituted by a phenyl group.
[0113] In the present disclosure, the phrase "bonded to an adjacent group to form a ring" may refer to a group bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring group or a substituted or unsubstituted heterocyclic group. The hydrocarbon ring may include an aliphatic hydrocarbon ring and / or an aromatic hydrocarbon ring. The heterocyclic ring may include an aliphatic heterocyclic ring and / or an aromatic heterocyclic ring. The hydrocarbon ring and the heterocyclic ring may each be a monocyclic or polycyclic ring. Additionally, a ring formed by bonding adjacent groups to each other may be connected to another ring to form a spiro structure.
[0114] In the present disclosure, the term "adjacent group" may refer to a substituent substituted for an atom directly connected to an atom substituted by a corresponding substituent, another substituent substituted for an atom substituted by a corresponding substituent, or a substituent spatially located in the closest position to the corresponding substituent. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane may be interpreted as "adjacent groups" to each other. In one or more embodiments, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups" to each other.
[0115] In the present disclosure, examples of halogens may include fluorine, chlorine, bromine, or iodine.
[0116] In the present disclosure, the alkyl group may be straight-chain or branched-chain. The number of carbon atoms in the alkyl group may be from 1 to 50, from 1 to 30, from 1 to 20, from 1 to 10, or from 1 to 6. Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, and / or n-triacontyl, etc., but the embodiments of the present disclosure are not limited thereto.
[0117] In the present disclosure, the cycloalkyl group may refer to a cyclic alkyl group. The number of carbon atoms in the cycloalkyl group may be from 3 to 50, from 3 to 30, from 3 to 20, or from 3 to 10. Examples of the cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl, and / or bicycloheptyl, etc., but the embodiments of the present disclosure are not limited thereto.
[0118] In the present disclosure, the alkenyl group refers to a hydrocarbon group including at least one carbon-carbon double bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. The alkenyl group may be straight-chain or branched-chain. The number of carbon atoms in the alkenyl group is not specifically limited. For example, it may be from 2 to 30, from 2 to 20, or from 2 to 10. Examples of the alkenyl group may include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, and / or styrylvinyl, etc., but the embodiments of the present disclosure are not limited thereto.
[0119] In the present disclosure, an alkynyl group refers to a hydrocarbon group including at least one carbon-carbon triple bond in the middle or at the end of an alkyl group having two or more carbon atoms. The alkynyl group may be straight-chain or branched-chain. Although the number of carbon atoms in the alkynyl group is not particularly limited, it may be 2 to 30, 2 to 20, or 2 to 10. Examples of the alkynyl group may include ethynyl and / or propynyl, etc., but the embodiments of the present disclosure are not limited thereto.
[0120] In the present disclosure, a hydrocarbon ring group refers to any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 ring-forming carbon atoms.
[0121] In the present disclosure, an aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring-forming carbon atoms in the aryl group may be 6 to 30, 6 to 20, or 6 to 15. Examples of the aryl group may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, sexiphenyl, triphenylene, pyrenyl, benzofluoranthenyl, and / or 1,2-benzophenanthryl, etc., but the embodiments of the present disclosure are not limited thereto.
[0122] In the present disclosure, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of the substituted fluorenyl group are as follows. However, the embodiments of the present disclosure are not limited thereto.
[0123]
[0124] As used herein, a heterocyclic group refers to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, S, and Se as a heteroatom. The heterocyclic group includes an aliphatic heterocyclic group and / or an aromatic heterocyclic group. The aromatic heterocyclic group may be a heteroaryl group. The aliphatic heterocycle and the aromatic heterocycle may each be monocyclic or polycyclic.
[0125] In the present disclosure, the heterocyclic group may contain at least one of B, O, N, P, Si, S, and Se as a heteroatom. If (e.g., when) the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and may include a heteroaryl group. The number of ring-forming carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.
[0126] In the present disclosure, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si, S, and Se as a heteroatom. The number of ring-forming carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic group may include oxiranyl, thiiranyl, pyrrolidinyl, piperidinyl, tetrahydrofuranyl, tetrahydrothienyl, thianyl, tetrahydropyranyl, and / or 1,4-dioxanyl, etc., but the embodiments of the present disclosure are not limited thereto.
[0127] In the present disclosure, a heteroaryl may contain at least one of B, O, N, P, Si, S, and Se as a heteroatom. If (e.g., when) the heteroaryl contains two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other. The heteroaryl may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring-forming carbon atoms in the heteroaryl may be 2 to 30, 2 to 20, or 2 to 10. Examples of the heteroaryl may include thienyl, furyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzosilolyl, and / or dibenzofuryl, etc., but the embodiments of the present disclosure are not limited thereto.
[0128] In the present disclosure, the above description of an aryl can be applied to an arylene, except that the arylene is a divalent group. The above description of a heteroaryl can be applied to a heteroarylene, except that the heteroarylene is a divalent group.
[0129] In the present disclosure, a silyl may include an alkylsilyl and / or an arylsilyl. The alkyl in the alkylsilyl may be linear, branched, or cyclic. The number of carbon atoms in the alkylsilyl is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylsilyl is not particularly limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of the silyl may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and / or phenylsilyl, etc., but the embodiments of the present disclosure are not limited thereto.
[0130] In the present disclosure, the number of carbon atoms in the carbonyl is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl may have the following structure, but the embodiments of the present disclosure are not limited thereto.
[0131]
[0132] In the present disclosure, the number of carbon atoms in the sulfinyl or sulfonyl is not particularly limited, and may be, for example, 1 to 30. The sulfinyl may include an alkylsulfinyl and / or an arylsulfinyl. The sulfonyl may include an alkylsulfonyl and / or an arylsulfonyl.
[0133] In the present disclosure, a thio group may include an alkylthio group and / or an arylthio group. The thio group may refer to a sulfur atom bonded to an alkyl group or an aryl group defined above. The alkyl group in the alkylthio group may be linear, branched, or cyclic. The number of carbon atoms in the alkylthio group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylthio group is not particularly limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of the thio group may include methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, and naphthylthio, but the embodiments of the present disclosure are not limited thereto.
[0134] In the present disclosure, an oxy group may refer to an oxygen atom bonded to an alkyl group or an aryl group defined above. The oxy group may include an alkoxy group and / or an aryloxy group. The alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the aryloxy group is not particularly limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of the oxy group may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, and / or benzyloxy, etc., but the embodiments of the present disclosure are not limited thereto.
[0135] As used herein, a boron group may refer to a boron atom bonded to an alkyl group or an aryl group defined above. The boron group may include an alkylboron group and / or an arylboron group. The alkyl group in the alkylboron group may be linear, branched, or cyclic. The number of carbon atoms in the alkylboron group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylboron group is not particularly limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of the boron group may include dimethylboron, tert-butylmethylboron, diphenylboron, and / or phenylboron, etc., but the embodiments of the present disclosure are not limited thereto.
[0136] In the present disclosure, an amino group may include an alkylamino group and / or an arylamino group. The alkyl group in the alkylamino group may be linear, branched, or cyclic. The number of carbon atoms in the alkylamino group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylamino group is not particularly limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Examples of the amino group may include methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, and / or 9-methyl-anthrylamino, etc., but the embodiments of the present disclosure are not limited thereto.
[0137] In the present disclosure, a sulfinyl group may refer to -S(=O)- bonded to an alkyl or aryl group as defined above. The number of carbon atoms of the sulfinyl group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The sulfinyl group may include an alkylsulfinyl group and an arylsulfinyl group. For example, the sulfinyl group may have the following structures, but is not limited thereto.
[0138]
[0139] In the present disclosure, a sulfonyl group may refer to -S(=O)2- bonded to an alkyl or aryl group as defined above. The number of carbon atoms of the sulfonyl group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The sulfonyl group may include an alkylsulfonyl group and an arylsulfonyl group. For example, the sulfonyl group may have the following structures, but is not limited thereto.
[0140]
[0141] In the present disclosure, a phosphinyl group may refer to -P(=O)- bonded to an alkyl or aryl group as defined above. The number of carbon atoms of the phosphinyl group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphinyl group may include an alkylphosphinyl group and an arylphosphinyl group. For example, the phosphinyl group may have the following structures, but is not limited thereto.
[0142]
[0143] In the present disclosure, a thiophosphinyl group may refer to -P(=S)- bonded to an alkyl or aryl group as defined above. The number of carbon atoms of the thiophosphinyl group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The thiophosphinyl group may include an alkylthiophosphinyl group and an arylthiophosphinyl group. For example, the thiophosphinyl group may have the following structures, but is not limited thereto.
[0144]
[0145] In the present disclosure, the alkyl group in an alkoxy group, an alkylthio group, an alkylsulfonyl group, an alkylsulfinyl group, an alkylaryl group, an alkylamino group, an alkylboron group, an alkylsilyl group, an alkylphosphinyl group, an alkylthiophosphinyl group, and an alkylamino group may be the same as the examples of the above alkyl group.
[0146] In the present disclosure, the aryl group in an aryloxy group, an arylthio group, an arylsulfonyl group, an arylsulfinyl group, an arylamino group, an arylboron group, an arylsilyl group, an arylphosphinyl group, an arylthiophosphinyl group, and an arylamino group may be the same as the examples of the above aryl group.
[0147] In the present disclosure, a direct bond may refer to a single bond.
[0148] In the present disclosure, and "-*" refers to the position to be bonded.
[0149] Hereinafter, embodiments of the present disclosure will be described in more detail with reference to the accompanying drawings. In the present disclosure, the term "light-emitting device" may be used interchangeably with the term "light-emitting element".
[0150] Figure 1 A plan view of a display device DD according to one or more embodiments of the present disclosure is shown. Figure 2 A cross-sectional view of a display device DD according to one or more embodiments of the present disclosure is shown. Figure 2 To illustrate a part of Figure 1 a cross-sectional view taken along line I-I' of the display device.
[0151] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP may include light-emitting devices ED-1, ED-2, and ED-3. The display device DD may include a plurality of light-emitting devices ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP to control light reflected at the display panel DP due to external light. The optical layer PP may include, for example, a polarization layer and / or a color filter layer. In one or more embodiments, the optical layer PP may not be provided in the display device DD.
[0152] A base substrate BL may be disposed on the optical layer PP. The base substrate BL may be a member providing a base surface on which the optical layer PP is disposed. The base substrate BL may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. In one or more embodiments, the base substrate BL may not be provided.
[0153] The display device DD according to one or more embodiments may further include a filling layer. The filling layer may be disposed between the display device layer DP-ED and the base substrate BL. The filling layer may be an organic material layer. The filling layer may include at least one of an acrylic resin, a silicone resin, and an epoxy resin.
[0154] The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED. The display device layer DP-ED may include a pixel defining film PDL, light-emitting devices ED-1, ED-2, and ED-3 disposed between respective portions of the pixel defining film PDL, and a packaging layer TFE disposed on the light-emitting devices ED-1, ED-2, and ED-3.
[0155] The base layer BS can be a component that provides a base surface, on which a display device layer DP-ED is arranged. The base layer BS can be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base layer BS can be an inorganic layer, an organic layer, or a composite material layer.
[0156] In one or more embodiments, a circuit layer DP-CL can be arranged on the base layer BS, and the circuit layer DP-CL can include a plurality of transistors. Each of the transistors can include a control electrode, an input electrode, and an output electrode. For example, in some embodiments, the circuit layer DP-CL can include switching transistors and driving transistors for driving light-emitting devices ED-1, ED-2, and ED-3 of the display device layer DP-ED.
[0157] Each of the light-emitting devices ED-1, ED-2, and ED-3 can have a structure of one of the light-emitting elements (devices) ED according to Figures 3 to 6 the embodiments, which will be described in more detail later. Each of the light-emitting devices ED-1, ED-2, and ED-3 can include a first electrode EL1, a hole transport region HTR, respective ones of emission layers EML-R, EML-G, and EML-B, an electron transport region ETR, and a second electrode EL2.
[0158] Figure 2 One or more embodiments are illustrated in which the respective emission layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3 are arranged in an opening OH defined by a pixel defining film PDL, and the hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are each provided as a common layer in the entire light-emitting devices ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto. For example, in one or more embodiments, the hole transport region HTR and the electron transport region ETR can be provided by patterning inside the opening OH defined by the pixel defining film PDL. For example, in one or more embodiments, the hole transport region HTR, the respective emission layers EML-R, EML-G, and EML-B, and the electron transport region ETR of the light-emitting devices ED-1, ED-2, and ED-3 can be provided by patterning by an inkjet printing method.
[0159] The encapsulation layer TFE can cover the light-emitting devices ED-1, ED-2, and ED-3. The encapsulation layer TFE can seal the light-emitting devices ED-1, ED-2, and ED-3 in the display device layer DP-ED. The encapsulation layer TFE can be a thin-film encapsulation layer. The encapsulation layer TFE can be formed by laminating one or more layers. The encapsulation layer TFE can include at least one insulating layer. The encapsulation layer TFE according to one or more embodiments can include at least one inorganic film (hereinafter referred to as an encapsulation-inorganic film). The encapsulation layer TFE according to one or more embodiments can also include at least one organic film (hereinafter referred to as an encapsulation-organic film) and at least one encapsulation-inorganic film.
[0160] The encapsulation-inorganic film protects the display device layer DP-ED from moisture / oxygen, and the encapsulation-organic film protects the display device layer DP-ED from foreign substances (such as dust particles). The encapsulation-inorganic film can include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, and / or aluminum oxide, etc., but the embodiments of the present disclosure are not particularly limited thereto. In some embodiments, the encapsulation-organic film can include acrylic compounds and / or epoxy compounds, etc. In some embodiments, the encapsulation-organic film can include a photo-polymerizable organic material, but the embodiments of the present disclosure are not particularly limited thereto.
[0161] The encapsulation layer TFE can be disposed on the second electrode EL2 and can be disposed to fill the opening OH.
[0162] Reference Figure 1 and Figure 2 , the display device DD can include a non-light-emitting area NPXA and light-emitting areas PXA-R, PXA-G, and PXA-B. The light-emitting areas PXA-R, PXA-G, and PXA-B can be areas that emit light generated by the respective light-emitting devices ED-1, ED-2, and ED-3. The light-emitting areas PXA-R, PXA-G, and PXA-B can be separated and / or apart from each other on a plane (e.g., in a plan view) (e.g., spaced apart or separated).
[0163] Each of the light-emitting areas PXA-R, PXA-G, and PXA-B can be an area defined by a pixel-defining film PDL. The non-light-emitting area NPXA can be an area between adjacent light-emitting areas PXA-R, PXA-G, and PXA-B, and the non-light-emitting area NPXA corresponds to the pixel-defining film PDL. In one or more embodiments, the light-emitting areas PXA-R, PXA-G, and PXA-B can respectively correspond to pixels. The pixel-defining film PDL can divide the light-emitting devices ED-1, ED-2, and ED-3. The respective emission layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3 can be disposed in the openings OH defined by the pixel-defining film PDL and separated from each other.
[0164] The light-emitting regions PXA-R, PXA-G, and PXA-B can be divided into multiple groups according to the colors of the light generated by the light-emitting devices ED-1, ED-2, and ED-3. In Figure 1 and Figure 2 In the display device DD of one or more embodiments illustrated, three light-emitting regions PXA-R, PXA-G, and PXA-B that emit red light, green light, and blue light, respectively, are exemplarily illustrated. For example, the display device DD of one or more embodiments may include a red light-emitting region PXA-R, a green light-emitting region PXA-G, and a blue light-emitting region PXA-B that are separated from each other.
[0165] In the display device DD according to one or more embodiments, the plurality of light-emitting devices ED-1, ED-2, and ED-3 may emit light beams having different wavelengths from each other. For example, in one or more embodiments, the display device DD may include a first light-emitting device ED-1 that emits red light, a second light-emitting device ED-2 that emits green light, and a third light-emitting device ED-3 that emits blue light. For example, in one or more embodiments, the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B of the display device DD may correspond to the first light-emitting device ED-1, the second light-emitting device ED-2, and the third light-emitting device ED-3, respectively.
[0166] However, the embodiments of the present disclosure are not limited thereto, and the first to third light-emitting devices ED-1, ED-2, and ED-3 may emit light beams within substantially the same wavelength range or at least one light-emitting device may emit a light beam having a different wavelength range from other light-emitting devices. For example, in some embodiments, the first to third light-emitting devices ED-1, ED-2, and ED-3 may all emit blue light.
[0167] The light-emitting regions PXA-R, PXA-G, and PXA-B in the display device DD according to one or more embodiments may be arranged in a stripe form. Referring to Figure 1 , a plurality of red light-emitting regions PXA-R may be arranged with respect to each other along the second direction axis DR2, a plurality of green light-emitting regions PXA-G may be arranged with respect to each other along the second direction axis DR2, and a plurality of blue light-emitting regions PXA-B may be arranged with respect to each other along the second direction axis DR2. In addition, the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B may be alternately arranged in this order along the first direction axis DR1.
[0168] Figure 1 and Figure 2It is illustrated that all the light-emitting regions PXA-R, PXA-G, and PXA-B have substantially the same area, but the embodiments of the present disclosure are not limited thereto. Thus, depending on the wavelength range of the emitted light, the light-emitting regions PXA-R, PXA-G, and PXA-B may have different areas from each other. The areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may refer to the areas when viewed on a plane defined by a first direction axis DR1 and a second direction axis DR2 (e.g., the area in a plan view). A third direction axis DR3 may be perpendicular to the plane defined by the first direction axis DR1 and the second direction axis DR2.
[0169] In one or more embodiments, the arrangement forms of the light-emitting regions PXA-R, PXA-G, and PXA-B are not limited to Figure 1 the configurations illustrated in, and the arrangement order of the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B may be provided in one or more appropriate combinations according to the characteristics of the desired or required display quality in the display device DD. For example, in one or more embodiments, the arrangement form of the light-emitting regions PXA-R, PXA-G, and PXA-B may be a honeycomb arrangement form (e.g., an RGBG matrix, an RGBG structure, or an RGBG matrix structure) or a diamond (Diamond ) arrangement form (e.g., a display (e.g., an OLED display) including red, green, and blue (RGB) light-emitting regions arranged in a diamond shape). is a trademark officially registered by Samsung Display Co., Ltd. Diamond is a trademark of Samsung Display Co., Ltd.
[0170] In one or more embodiments, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in one or more embodiments, the area of the green light-emitting region PXA-G may be smaller than the area of the blue light-emitting region PXA-B, but the embodiments of the present disclosure are not limited thereto.
[0171] Hereinafter, Figures 3 to 6 cross-sectional views of light-emitting elements according to one or more embodiments of the present disclosure are schematically shown. The light-emitting element ED of one or more embodiments may include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 stacked in the recited order.
[0172] Compared with Figure 3 Figure 4A cross-sectional view of a light-emitting element ED according to one or more embodiments is illustrated, in which a hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and an electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Additionally, compared with Figure 3 compared with Figure 5 A cross-sectional view of a light-emitting element ED according to one or more embodiments is illustrated, in which a hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and an electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Compared with Figure 4 compared with Figure 6 A cross-sectional view of a light-emitting element ED according to one or more embodiments including a capping layer CPL disposed on a second electrode EL2 is illustrated.
[0173] The first electrode EL1 has conductivity (e.g., is a conductor). The first electrode EL1 can be formed of a metal material, a metal alloy, and / or a conductive compound. The first electrode EL1 can be an anode or a cathode. However, the embodiments of the present disclosure are not limited thereto. In one or more embodiments, the first electrode EL1 can be a pixel electrode. The first electrode EL1 can be a transmissive electrode, a transmissive-reflective electrode, or a reflective electrode. The first electrode EL1 can include at least one selected from silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), lithium fluoride (LiF), molybdenum (Mo), titanium (Ti), tungsten (W), indium (In), tin (Sn), and zinc (Zn), a compound of two or more selected therefrom, a mixture of two or more selected therefrom, and / or an oxide thereof.
[0174] If (e.g., when) the first electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO). If (e.g., when) the first electrode EL1 is a transmissive-reflective electrode or a reflective electrode, the first electrode EL1 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, and W, a compound or a mixture thereof (e.g., a mixture of Ag and Mg), or a material having a multilayer structure such as LiF / Ca (a stacked structure of LiF and Ca) or LiF / Al (a stacked structure of LiF and Al). In one or more embodiments, the first electrode EL1 may have a multilayer structure including a reflective film or a transmissive-reflective film formed of one or more of the above materials and a transparent conductive film formed of ITO, IZO, ZnO, and / or ITZO. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the embodiments of the present disclosure are not limited thereto. Additionally, the first electrode EL1 may include one of the above metal materials, one or more combinations of at least two of the above metal materials, and / or any oxide of the above metal materials. The thickness of the first electrode EL1 may be about 700 angstroms to about For example, in one or more embodiments, the thickness of the first electrode EL1 may be about to about
[0175] The hole transport region HTR may be provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a buffer layer, an emission assist layer, and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about to about
[0176] The hole transport region HTR may have: a single-layer structure including a single layer formed of a single material, a single-layer structure including a single layer formed of a plurality of different materials, or a multilayer structure including a plurality of layers formed of a plurality of different materials.
[0177] For example, in one or more embodiments, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or may have a single-layer structure formed of a hole injection material and a hole transport material. In one or more embodiments, the hole transport region HTR may have a single-layer structure formed of a plurality of different materials, or a structure in which a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / buffer layer, a hole injection layer HIL / buffer layer, a hole transport layer HTL / buffer layer, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL is stacked in order (e.g., in the recited order) from the first electrode EL1, but the embodiments of the present disclosure are not limited thereto.
[0178] The hole transport region HTR can be formed using one or more suitable methods, such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and / or laser-induced thermal imaging (LITI) method.
[0179] In one or more embodiments, the hole transport region HTR may include a compound represented by Formula H-1:
[0180] Formula H-1
[0181]
[0182] In Formula H-1, L1 and L2 may each independently be a direct bond, a substituted or unsubstituted arylene having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 30 ring carbon atoms. a and b may each independently be an integer selected from 0 to 10. In one or more embodiments, if (e.g., when) a or b is an integer of 2 or greater, then the plurality of L1 and the plurality of L2 may each independently be a substituted or unsubstituted arylene having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 30 ring carbon atoms.
[0183] In Formula H-1, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms. Additionally, in Formula H-1, Ar3 may be a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms.
[0184] In one or more embodiments, the compound represented by formula H-1 can be a monoamine compound. In one or more embodiments, the compound represented by formula H-1 can be a diamine compound, wherein at least one selected from Ar1 to Ar3 includes an amine group as a substituent. In one or more embodiments, the compound represented by formula H-1 can be a carbazole compound including a substituted or unsubstituted carbazolyl group in at least one of Ar1 and Ar2, or a fluorene compound including a substituted or unsubstituted fluorenyl group in at least one of Ar1 and Ar2.
[0185] The compound represented by formula H-1 can be any one of the compounds selected from the group of compounds H. However, the compounds listed in the group of compounds H are only examples, and the compound represented by formula H-1 is not limited to those compounds represented in the group of compounds H:
[0186] Group of compounds H
[0187]
[0188]
[0189] In one or more embodiments, the hole transport region HTR can include at least one selected from the following: phthalocyanine compounds such as copper phthalocyanine; N 1 ,N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4 -di-m-tolylbenzene-1,4-diamine)(DNTPD), 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine (NPB), a polyether ketone containing triphenylamine (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate] and / or dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), etc.
[0190] In one or more embodiments, the hole transport region HTR may include at least one selected from the following: carbazole derivatives such as N-phenylcarbazole or polyvinylcarbazole; fluorene derivatives; triphenylamine derivatives such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4',4''-tris(carbazol-9-yl)triphenylamine (TCTA), N,N'-bis(naphthalen-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), and / or 1,3-bis(carbazol-9-yl)benzene (mCP), etc.
[0191] In one or more embodiments, the hole transport region HTR may include at least one selected from the following: 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9'-bicarbazole (CCP), and 1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene (mDCP), etc.
[0192] The hole transport region HTR may include one or more of the above compounds of the hole transport region HTR in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.
[0193] The thickness of the hole transport region HTR may be about to about For example, about to about When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have, for example, about to about a thickness. When the hole transport region HTR includes the hole transport layer HTL, the hole transport layer HTL may have about to about a thickness. For example, if (for example, when) the hole transport region HTR includes the electron blocking layer EBL, then the electron blocking layer EBL may have about to about a thickness. If (for example, when) the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above ranges, satisfactory hole transport characteristics can be achieved without significantly increasing the driving voltage.
[0194] In one or more embodiments, in addition to the above materials, the hole transport region HTR may further include a charge generation material to increase conductivity (e.g., electrical conductivity). The charge generation material may be uniformly (e.g., substantially uniformly) or non-uniformly dispersed in the hole transport region HTR. The charge generation material may be, for example, a p-dopant. The p-dopant may include at least one of metal halides, quinone derivatives, metal oxides, and cyanide-containing compounds, but embodiments of the present disclosure are not limited thereto. For example, in one or more embodiments, the p-dopant may include metal halides such as CuI and / or RbI, quinone derivatives such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), metal oxides such as tungsten oxide and / or molybdenum oxide, and cyanide-containing compounds such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) and / or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropenylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9), etc., but embodiments of the present disclosure are not limited thereto.
[0195] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a buffer layer and an electron blocking layer EBL. The buffer layer may compensate for the resonance distance according to the wavelength of light emitted from the emission layer EML, and may thus increase the light emission efficiency. The materials that may be included in the hole transport region HTR may be used as the materials to be included in the buffer layer. The electron blocking layer EBL is a layer for preventing or reducing the injection of electrons from the electron transport region ETR into the hole transport region HTR.
[0196] The emission layer EML may be provided on the hole transport region HTR. The emission layer EML may have, for example, about to about or about to about of thickness. The emission layer EML may have: a single-layer structure including a single layer formed of a single material, a single-layer structure including a single layer formed of a plurality of different materials, or a multi-layer structure having a plurality of layers formed of a plurality of different materials.
[0197] The light-emitting element ED according to one or more embodiments may include a fused polycyclic compound represented by Formula 1 in at least one functional layer disposed between a first electrode EL1 and a second electrode EL2. In the light-emitting element ED according to one or more embodiments, the emission layer EML may include the fused polycyclic compound represented by Formula 1 according to one or more embodiments. In one or more embodiments, the emission layer EML may include the fused polycyclic compound represented by Formula 1 according to one or more embodiments as a light-emitting dopant (light-emitting material). The fused polycyclic compound represented by Formula 1 according to one or more embodiments may be a dopant material for the emission layer EML. In the present disclosure, as used herein, the fused polycyclic compound represented by Formula 1 according to one or more embodiments may be referred to as a first compound.
[0198] The fused polycyclic compound represented by Formula 1 according to one or more embodiments may include a fused structure in which a plurality of aromatic rings are fused via a boron atom and a nitrogen atom. The fused polycyclic compound represented by Formula 1 according to one or more embodiments may include a fused structure in which a plurality of aromatic rings are fused via one boron atom and two nitrogen atoms. The fused polycyclic compound represented by Formula 1 according to one or more embodiments may include a fused structure in which a plurality of aromatic rings are fused via a first boron atom, a first nitrogen atom, and a second nitrogen atom. For example, the fused polycyclic compound represented by Formula 1 according to one or more embodiments may include a fused ring formed by fusing a plurality of aromatic rings via one boron atom, a first nitrogen atom, and a second nitrogen atom.
[0199] The fused polycyclic compound represented by Formula 1 according to one or more embodiments may include a fused structure in which a first to third aromatic rings (i.e., a first aromatic ring, a second aromatic ring, and a third aromatic ring) are fused via a first boron atom, a first skeleton atom, and a second skeleton atom. The first aromatic ring, the second aromatic ring, and the third aromatic ring may each be connected to the first boron atom, the first aromatic ring and the third aromatic ring may be further connected via the first skeleton atom, and the second aromatic ring and the third aromatic ring may be further connected via the second skeleton atom. In one or more embodiments, as used herein, the first boron atom, the first skeleton atom, and the second skeleton atom, and the fused structure formed by fusing the first to third aromatic rings via the first boron atom, the first skeleton atom, and the second skeleton atom may be referred to as a "fused ring core". In one or more embodiments, the first skeleton atom may be a nitrogen atom. The second skeleton atom may be a nitrogen atom, a carbon atom, an oxygen atom, a sulfur atom, a selenium atom, or a phosphorus atom.
[0200] In one or more embodiments, the first to third aromatic rings may each independently be a substituted or unsubstituted monocyclic aromatic hydrocarbon ring having 6 to 30 ring carbon atoms. In one or more embodiments, the first to third aromatic hydrocarbon rings may each independently be a six-membered aromatic hydrocarbon ring. For example, in one or more embodiments, the first to third aromatic hydrocarbon rings may each independently be a benzene ring.
[0201] The fused polycyclic compound represented by Formula 1 according to one or more embodiments may include a first substituent attached to a first skeleton atom. The first substituent may include a biphenyl moiety and a second substituent attached to the biphenyl moiety. The first substituent may include a 2-biphenyl moiety, and the second substituent may be attached to the second carbon (2'-carbon position) of the 2-biphenyl moiety. For example, in the 2-biphenyl moiety of the first substituent, the second benzene ring may be attached to the second carbon (2-carbon position) of the first benzene ring (attached to the first skeleton atom), and the second substituent (such as an aryl or heteroaryl) may be attached to the second carbon (2'-carbon position) of the second benzene ring. In the present disclosure, the structure and carbon numbering of the first substituent may be the same as that described by Formula S.
[0202] Formula S
[0203]
[0204] For ease of explanation, in Formula S, for illustrative purposes, the 3 to 6 carbon positions and 3' to 6' carbon positions of the 2-biphenyl moiety are each illustrated as unsubstituted, but substituents may be substituted at each carbon position (e.g., present at each carbon position).
[0205] In Formula S, Z is the second substituent described above. Z may be, for example, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
[0206] In Formula S, -* is the position where the first skeleton atom is connected.
[0207] In one or more embodiments, the first substituent may be directly bonded to the first nitrogen atom of the fused ring nucleus without a linker (e.g., without an additional linker).
[0208] The fused polycyclic compound according to one or more embodiments may be represented by Formula 1.
[0209] Formula 1
[0210]
[0211] The fused polycyclic compound represented by Formula 1 according to one or more embodiments may include a structure in which three aromatic rings are fused via a boron atom, a first nitrogen atom, and a second skeletal atom included in X. In the present disclosure, as used herein, in Formula 1, the benzene ring substituted with the substituents represented by R d to R g may correspond to the first aromatic ring described above, the benzene ring substituted with the substituents represented by R h to R k may correspond to the second aromatic ring described above, and the benzene ring substituted with the substituents represented by R a to R c may correspond to the third aromatic ring described above. In Formula 1, the nitrogen atom may correspond to the first skeletal atom described above, and X may correspond to a chemical moiety including or consisting of the second skeletal atom described above. In Formula 1, the biphenyl moiety connected to the nitrogen atom and including the substituent Z may correspond to the first substituent, and the substituent Z may correspond to the second substituent.
[0212] In Formula 1, X may be a direct bond, O, S, Se, CR 31 R 32 , PR 33 , SiR 34 R 35 , C═O, C═S, or NR 36 . For example, in one or more embodiments, X may be O, S, Se, CR 31 R 32 , PR 33 , SiR 34 R 35 , C═O, or NR 36 .
[0213] In Formula 1, Z may be a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in one or more embodiments, Z may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted phenylthio group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
[0214] In Formula 1, R1 to R8, R a to R k and R 31 to R 36Each may independently be hydrogen, deuterium, a halogen, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. In one or more embodiments, any one of R1 to R8, R a to R k and R 31 to R 36 may be bonded to an adjacent group to form a ring. For example, in one or more embodiments, R1 may be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted oxy group, or a substituted or unsubstituted amino group. For example, in one or more embodiments, R2 to R8 may each independently be hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group. For example, in one or more embodiments, R a to R k may each independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenoxazinyl group, or a substituted or unsubstituted phenothiazinyl group. For example, in one or more embodiments, R 31 to R 36 may each independently be a substituted or unsubstituted methyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, or a substituted or unsubstituted quinquephenyl group. In one or more embodiments, adjacent R e and R f , R i and R j are each independently linked together to form an additional hydrocarbon ring group or heterocyclic group. In one or more embodiments, X may be NR 36 , and adjacent R 36 and R a , R a and R b are each independently linked together to form an additional hydrocarbon ring group or heterocyclic group.
[0215] In one or more embodiments, in Formula 1, if (e.g., when) any one selected from R1 to R8, R a to R k and R 31 to R 36 is linked to an adjacent group to form a ring, the formed ring does not include two consecutive sp 3 hybridized carbons bonded to each other. If (e.g., when) any one selected from R1 to R8, R a to R k and R 31 to R 36 is linked to an adjacent group to form a ring, the formed ring does not include a structure containing two consecutive sp 3 hybridized carbons bonded to each other as shown in Formula X.
[0216] Formula X
[0217]
[0218] Formula X shows the case where M1 to M4 are each any substituent, and the first carbon substituted by M1 and M2 and the second carbon substituted by M3 and M4 are both sp 3 hybridized carbons. In the fused polycyclic compound represented by Formula 1 according to one or more embodiments, if (e.g., when) any one selected from R1 to R8, R a to R k and R 31 to R 36 is bonded to an adjacent group to form a ring, the formed ring may not have a saturated hydrocarbon structure such as Formula X. In Formula X, -* is the connection position.
[0219] In one or more embodiments, in Formula 1, if (e.g., when) some of those selected from R1 to R8, R a to R k and R 31 to R 36 are each bonded to an adjacent group to form a ring, the formed ring may be an aromatic ring.
[0220] In one or more embodiments, in Formula 1, if (e.g., when) Z is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, then R5 may not be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms. In one or more embodiments, in Formula 1, if (e.g., when) Z is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, then R5 may be hydrogen or deuterium.
[0221] In one or more embodiments, in Formula 1, R d to R kEach may independently be hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, or any one of the substituents represented by Formulae a-1 to a-8.
[0222] Formula a-1
[0223]
[0224] Formula a-2
[0225]
[0226] Formula a-3
[0227]
[0228] Formula a-4
[0229]
[0230] Formula a-5
[0231]
[0232] Formula a-6
[0233]
[0234] Formula a-7
[0235]
[0236] Formula a-8
[0237]
[0238] In Formulae a-1 to a-8, *- indicates the position at which the fused polycyclic ring nucleus represented by Formula 1 is attached.
[0239] In one or more embodiments, in Formula 1, R a to R c may each independently be hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, or a substituted or unsubstituted tert-butyl group, or any one of the substituents represented by Formulae b-1 to b-9.
[0240] Formula b-1
[0241]
[0242] Formula b-2
[0243]
[0244] Formula b-3
[0245]
[0246] Formula b-4
[0247]
[0248] Formula b-5
[0249]
[0250] Formula b-6
[0251]
[0252] Formula b-7
[0253]
[0254] Formula b-8
[0255]
[0256] Formula b-9
[0257]
[0258] In Formulas b-1 to b-9, *- indicates the position where the fused ring nucleus of the fused polycyclic compound represented by Formula 1 is connected.
[0259] The fused polycyclic compound represented by Formula 1 according to one or more embodiments has a structure in which a first substituent is connected to the fused ring nucleus, and thus high luminous efficiency and long element service life can be achieved.
[0260] The fused polycyclic compound represented by Formula 1 according to one or more embodiments includes a "fused ring nucleus" having five rings, which is formed by fusing the first to third aromatic rings through a boron atom, a first backbone atom, and a second backbone atom. In addition, the fused polycyclic compound represented by Formula 1 according to one or more embodiments includes a first substituent connected to the first backbone atom of the fused ring nucleus. The fused polycyclic compound represented by Formula 1 according to one or more embodiments includes a first substituent, thereby enabling high luminous efficiency and long element service life.
[0261] The first substituent may include a 2-biphenyl moiety, and the second substituent may be connected to the second carbon of the 2-biphenyl moiety. The first substituent has a 2-biphenyl moiety represented by formula S, and is connected to a nitrogen atom as a first skeletal atom at the first carbon position (1-carbon position) of the 2-biphenyl moiety shown in formula S. The first substituent is substituted with a second substituent at the second carbon position (2'-carbon position), and the second substituent may be a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. The fused polycyclic compound represented by formula 1 according to one or more embodiments includes a first substituent connected to a nitrogen atom of a fused ring nucleus, and the trigonal planar structure of the boron atom can be effectively maintained by the steric effect caused by the first substituent having a high steric volume. The boron atom has an electron-deficient property due to an unoccupied p-orbital, and thus can form a bond with another nucleophile, and its structure can be changed to a tetrahedral structure, which can cause device degradation. According to one or more embodiments of the present disclosure, since the first substituent is used for the fused ring nucleus of the fused polycyclic compound, the unoccupied p-orbital of the boron atom can be effectively protected, and the degradation phenomenon caused by structural deformation can be prevented or reduced.
[0262] In addition, in the fused polycyclic compound represented by formula 1 according to one or more embodiments, due to the steric effect caused by the first substituent, the intermolecular reaction can be suppressed or reduced, and thus the aggregation and formation of excited molecules or excited complexes can be controlled, which can lead to an increase in luminescence efficiency. Since the fused polycyclic compound represented by formula 1 according to one or more embodiments has a bulky structure due to the introduction of the first substituent having a large volume, the intermolecular distance increases, and thus the Dexter energy transfer can be suppressed or reduced. Therefore, the increase in the concentration of triplet excitons in the fused polycyclic compound represented by formula 1 can be suppressed or reduced. A high concentration of triplet excitons in the excited state for a long time can cause the compound to decompose and generate high-energy hot excitons through triplet-triplet annihilation (TTA). Therefore, the structure of the surrounding compounds can be damaged or induced. In addition, triplet-triplet annihilation is a bimolecular reaction, which quickly depletes the triplet excitons for luminescence, and thus non-radiative transition can cause a decrease in luminescence efficiency. In the fused polycyclic compound represented by formula 1 according to one or more embodiments, due to the first substituent, the intermolecular distance increases, and thus the Dexter energy transfer can be suppressed or reduced. Therefore, the deterioration of the device service life of the fused polycyclic compound represented by formula 1 caused by the increase in the concentration of triplet excitons can be suppressed or reduced. Therefore, if (for example, when) the fused polycyclic compound represented by formula 1 according to one or more embodiments is used in the emission layer EML of the light-emitting device ED, not only the luminescence efficiency can be increased, but also the device service life can be improved.
[0263] Since the fused polycyclic compound represented by Formula 1 according to one or more embodiments includes a first substituent, characterized in that a higher excited triplet energy level (Tn energy level, where n is 2 or greater) adjacent to the lowest excited singlet energy level (S1 energy level) may exhibit a relatively low energy level. In one or more embodiments, in the fused polycyclic compound represented by Formula 1 according to one or more embodiments, the energy difference (ΔE S1Tn ) between the lowest excited singlet energy level (S1 energy level) and a higher excited triplet energy level (Tn energy level, where n is 2 or greater) adjacent to the lowest excited singlet energy level (S1 energy level) may be about 0.6 eV or less. In one or more embodiments, in the fused polycyclic compound represented by Formula 1 according to one or more embodiments, the energy difference (ΔE S1Tn ) between the lowest excited singlet energy level (S1 energy level) and a higher excited triplet energy level (Tn energy level) adjacent to the lowest excited singlet energy level (S1 energy level) may be about 0.2 eV or less. For example, in the fused polycyclic compound including a first substituent according to one or more embodiments, the energy difference (ΔE S1Tn ) between the lowest excited singlet energy level and the second excited triplet energy level (T2 energy level) may be about 0.2 eV or less.
[0264] In compounds exhibiting thermally activated delayed fluorescence characteristics, intersystem crossing (ISC) occurs in which an exciton transfers from the lowest excited singlet energy level to a higher excited triplet energy level. Thereafter, reverse intersystem crossing (RISC) occurs in which the exciton transfers from the higher excited triplet energy level to the lowest excited singlet energy level. Finally, the exciton transfers from the lowest excited singlet energy level to the ground state to exhibit / emmit delayed fluorescence. In the present text, the thermally activated delayed fluorescence mechanism may include passing through a higher excited triplet energy level (Tn energy level) and the lowest excited triplet energy level (T1 energy level) during the intersystem crossing (ISC) and reverse intersystem crossing (RISC) processes. Because the fused polycyclic compound represented by Formula 1 according to one or more embodiments includes a first substituent, characterized in that the higher excited triplet energy level (Tn energy level) adjacent to the lowest excited singlet energy level (S1 energy level) is low. Accordingly, the spin flip can be increased. As used herein, spin flip may refer to the following phenomenon: in which due to the spin-orbit coupling (SOC) between the lowest excited singlet energy level (S1 energy level) and the adjacent higher excited triplet energy level (Tn energy level), the exciton of the higher excited triplet energy level (Tn energy level) transfers to the lowest excited singlet energy level (S1 energy level). Therefore, because the fused polycyclic compound represented by Formula 1 according to one or more embodiments exhibits the characteristic that the higher excited triplet energy level (Tn energy level) adjacent to the lowest excited singlet energy level (S1 energy level) is low, the reverse intersystem crossing (RISC) rate can be increased from the higher excited triplet energy level (Tn energy level) to the lowest excited singlet energy level (S1 energy level), and the delayed fluorescence lifetime / service life (Tau, τ) can be reduced, which can lead to an improvement in the luminescence efficiency and element service life characteristics of the fused polycyclic compound represented by Formula 1.
[0265] According to one or more embodiments, the fused polycyclic compound represented by Formula 1 can be represented by any one selected from Formulas 2-1 to 2-8.
[0266] Formula 2-1
[0267]
[0268] Formula 2-2
[0269]
[0270] Formula 2-3
[0271]
[0272] Formula 2-4
[0273]
[0274] Formula 2-5
[0275]
[0276] Formula 2-6
[0277]
[0278] Formula 2-7
[0279]
[0280] Formula 2-8
[0281]
[0282] Formulas 2-1 to 2-8 are formulas showing specific embodiments of the substituent Z in Formula 1.
[0283] In Formulas 2-1 to 2-8, R9 to R 19 may each independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms. For example, in one or more embodiments, R9 to R 19 may each independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted methyl, a substituted or unsubstituted tert-butyl, or a substituted or unsubstituted phenyl.
[0284] In Formulas 2-5 and 2-8, Y1 and Y2 may each independently be O or S.
[0285] In Formula 2-1, n9 may be an integer selected from 0 to 5. If (for example, when) n9 in Formula 2-1 is 0, it means that the fused polycyclic compound according to one or more embodiments is not substituted by R9. The embodiment in which n9 in Formula 2-1 is 5 and all R9 are each hydrogen is the same as the embodiment in which n9 is 0. In Formula 2-1, if (for example, when) n9 is an integer of 2 or greater, the plurality of provided R9 may all be the same, or at least one selected from the plurality of R9 may be different.
[0286] In Formulas 2-5 to 2-8, n14 to n18 may each independently be an integer selected from 0 to 4. In Formulas 2-5 to 2-8, the embodiment in which n14 to n18 are each 0 means that the fused polycyclic compound according to one or more embodiments may not be substituted by R 14 to R 18 respectively. In Formulas 2-5 to 2-8, the embodiment in which n14 to n18 are each 4 and R 14 to R 18Embodiments in which each is hydrogen may be the same as embodiments in which n14 to n18 are each 0. In Formulas 2-5 to 2-8, if (e.g., when) n14 to n18 are each an integer of 2 or greater, then Rs provided in plurality 14 to R 18 may all be the same, or at least one selected from Rs provided in plurality 14 to R 18 may be different.
[0287] In Formula 2-8, n19 may be an integer selected from 0 to 3. In Formula 2-8, an embodiment in which n19 is 0 may mean that the fused polycyclic compound according to one or more embodiments is not substituted with R 19 . In Formula 2-8, an embodiment in which n19 is 3 and each of R 19 is a hydrogen atom may be the same as an embodiment in which n19 is 0. In Formula 2-8, if (e.g., when) n19 is an integer of 2 or greater, then Rs provided in plurality 19 may all be the same, or at least one selected from a plurality of Rs 19 may be different.
[0288] In Formulas 2-1 to 2-8, the descriptions defined in Formula 1 may be similarly applied to X, R1 to R8, R a to R k and R 31 to R 36 .
[0289] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from Formulas 3-1 and 3-2.
[0290] Formula 3-1
[0291]
[0292] Formula 3-2
[0293]
[0294] In Formula 3-1, A1 may be hydrogen, deuterium, a substituted or unsubstituted oxy group, or a substituted or unsubstituted amino group. For example, in one or more embodiments, A1 may be hydrogen, deuterium, a substituted or unsubstituted phenoxy group, or a substituted or unsubstituted diphenylamino group.
[0295] In Formula 3-2, A2 may be hydrogen, deuterium, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in one or more embodiments, A2 may be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted phenylthio group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
[0296] In one or more embodiments, in Formula 3-2, Z and A2 may be the same. For example, in some embodiments, Z and A2 may be phenyl groups having the same structure. For example, Z and A2 may each be an unsubstituted phenyl group.
[0297] In Formula 3-2, R m may be hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in one or more embodiments, R m may be hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.
[0298] In Formula 3-2, m may be an integer selected from 0 to 4. In Formula 3-2, an embodiment in which m is 0 may mean that the fused polycyclic compound according to one or more embodiments is not substituted by R m . In Formula 3-2, an embodiment in which m is 4 and each R m is hydrogen may be the same as an embodiment in which m is 0. In Formula 3-2, if (for example, when) m is an integer of 2 or greater, then the plurality of provided R m may all be the same, or at least one selected from the plurality of R m may be different.
[0299] In Formulas 3-1 and 3-2, the descriptions defined in Formula 1 may be similarly applied to X, Z, R2 to R8, R a to R k and R 31 to R 36 .
[0300] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from Formulas 4-1 to 4-4.
[0301] Formula 4-1
[0302]
[0303] Formula 4-2
[0304]
[0305] Formula 4-3
[0306]
[0307] Formula 4-4
[0308]
[0309] In Formulas 4-1 to 4-4, X1 to X5 can each independently be O, S, CR 26 R 27 or NR 28 . For example, in one or more embodiments, X1 to X5 can each be NR 28 .
[0310] In Formulas 4-1 to 4-4, R a1 to R k1 and R 20 to R 28 can each independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted amino, substituted or unsubstituted oxy, substituted or unsubstituted thio, substituted or unsubstituted carbonyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms. In one or more embodiments, adjacent groups selected from R a1 to R k1 can bond to form a ring. For example, in one or more embodiments, R a1 to R k1 can each independently be hydrogen, deuterium, halogen, substituted or unsubstituted oxy, substituted or unsubstituted thio, substituted or unsubstituted amino, substituted or unsubstituted boron, substituted or unsubstituted methyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted carbonyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted carbazolyl. For example, in one or more embodiments, R 20 to R 28 can each independently be substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, or substituted or unsubstituted quinquephenyl. In one or more embodiments, adjacent R e1and R f1 、R i1 and R j1 may be independently bonded to each other to form additional heterocycles. For example, in some embodiments, adjacent R e1 and R f1 、R i1 and R j1 may be independently bonded to each other to form a ring, thereby forming a benzofuran moiety.
[0311] In Formulas 4-2 to 4-4, n20 and n23 to n25 may each independently be an integer selected from 0 to 4. In Formulas 4-2 to 4-4, embodiments in which n20 and n23 to n25 are each 0 may refer to the fused polycyclic compounds according to one or more embodiments not being substituted by R 20 、R 23 to R 25 respectively. In Formulas 4-2 to 4-4, embodiments in which n20 and n23 to n25 are each 4 and R 20 、R 23 to R 25 are each hydrogen may be the same as the embodiments in which n20 and n23 to n25 are 0 respectively. In Formulas 4-2 and 4-4, if (e.g., when) n20 and n23 to n25 are each an integer of 2 or greater, then R 20 and R 23 to R 25 each provided in plurality may all be the same, or at least one selected from a plurality of R 20 and R 23 to R 25 may be different.
[0312] In Formulas 4-2 and 4-3, n21 and n22 may each independently be an integer selected from 0 to 3. In Formulas 4-2 and 4-3, embodiments in which n21 and n22 are each 0 may refer to the fused polycyclic compounds according to one or more embodiments not being substituted by R 21 and R 22 respectively. In Formulas 4-2 and 4-3, embodiments in which n21 and n22 are each 3 and R 21 and R 22 are each hydrogen may be the same as the embodiments in which n21 and n22 are 0 respectively. In Formulas 4-2 and 4-3, if (e.g., when) n21 and n22 are each an integer of 2 or greater, then R 21 and R 22 each provided in plurality may all be the same, or at least one selected from a plurality of R 21 and a plurality of R 22 may be different.
[0313] In Formulas 4-1 to 4-4, the descriptions defined in Formula 1 can be similarly applied to X, Z, R1 to R8, and R 31 to R 36 .
[0314] In one or more embodiments, the fused polycyclic compound represented by Formula 1 can be represented by Formula 5.
[0315] Formula 5
[0316]
[0317] In Formula 5, R x can be hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in one or more embodiments, R x can be hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted phenylthio group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
[0318] In Formula 5, nx can be an integer selected from 0 to 5. In Formula 5, an embodiment where nx is 0 may refer to the fused polycyclic compound according to one or more embodiments not being substituted by R x . In Formula 5, an embodiment where nx is 5 and each R x is hydrogen may be the same as the embodiment where nx is 0. In Formula 5, if (for example, when) nx is an integer of 2 or greater, then the multiple Rs provided x can all be the same, or at least one selected from the multiple Rs x can be different.
[0319] In Formula 5, the descriptions defined in Formula 1 can be similarly applied to Z, R1 to R8, and R a to R k .
[0320] In one or more embodiments, the fused polycyclic compound represented by Formula 1 can be represented by Formula 6.
[0321] Formula 6
[0322]
[0323] In Formula 6, Z1 and Z2 can each independently be a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in one or more embodiments, Z1 and Z2 can each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted phenylthio group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
[0324] In Formula 6, R 41 to R 48 can each independently be hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. In one or more embodiments, one or more selected from R 41 to R 48 can each independently bond to an adjacent group to form a ring. For example, in some embodiments, R 41 can be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted oxy group, or a substituted or unsubstituted amino group. For example, in some embodiments, R 42 to R 48 can each independently be hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.
[0325] In one or more embodiments, in Formula 6, if (for example, when) any one selected from R 41 to R 48 bonds to an adjacent group to form a ring, the formed ring does not include two consecutive sp 3 hybridized carbons bonded to each other. In one or more embodiments, if (for example, when) any one selected from R 41 to R 48 bonds to an adjacent group to form a ring, the formed ring does not include a structure containing two consecutive sp 3 hybridized carbons bonded to each other. In one or more embodiments, in Formula 6, if (for example, when) R41 to R 48 When some of them are each independently bonded to adjacent groups to form a ring, the formed ring can be an aromatic ring.
[0326] In one or more embodiments, in Formula 6, if (e.g., when) Z1 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, then R5 may not be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. In one or more embodiments, in Formula 6, if (e.g., when) Z1 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, then R5 may be hydrogen or deuterium.
[0327] In one or more embodiments, in Formula 6, if Z2 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, then R 45 may not be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. In one or more embodiments, in Formula 6, if Z2 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, then R 45 may be hydrogen or deuterium.
[0328] In one or more embodiments, in Formula 6, Z1 and Z2 can be the same. For example, in one or more embodiments, Z1 and Z2 can each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted phenylthio group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, or a substituted or unsubstituted carbazolyl group, and can have the same chemical structure.
[0329] In one or more embodiments, the fused polycyclic compound according to one or more embodiments can have an axisymmetric structure centered on the boron atom of the fused ring nucleus and the third aromatic ring. In one or more embodiments, the fused polycyclic compound can be represented by Formula 6, and R1 and R 41 can be the same, and Z1 and Z2 can have the same structure.
[0330] In Formula 6, the descriptions defined in Formula 1 can be similarly applied to R1 to R8 and R a to R k .
[0331] In one or more embodiments, the fused polycyclic compound represented by Formula 6 can be represented by Formula 6-1.
[0332] Formula 6-1
[0333]
[0334] In Formula 6-1, A3 and A4 can each independently be hydrogen, deuterium, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in one or more embodiments, A3 and A4 can each independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted phenylthio group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
[0335] In one or more embodiments, in Formula 6-1, Z1 and A3 can be the same. For example, in some embodiments, Z1 and A3 can each be a phenyl group having the same chemical structure. Z1 and A3 can each be an unsubstituted phenyl group. In one or more embodiments, in Formula 6-1, Z2 and A4 can be the same. For example, in some embodiments, Z2 and A4 can each be a phenyl group having the same chemical structure. For example, Z2 and A4 can each be an unsubstituted phenyl group.
[0336] In Formula 6-1, R 29 and R 30 can each independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in one or more embodiments, R 29 and R 30 can each independently be hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.
[0337] In Formula 6-1, n29 and n30 can each be an integer selected from 0 to 4. In Formula 6-1, the embodiment where n29 and n30 are each 0 can mean that the fused polycyclic compound according to one or more embodiments is not respectively substituted by R 29 and R 30 . In Formula 6-1, the embodiment where n29 and n30 are each 4 and R 29 and R 30 are each hydrogen can be the same as the embodiment where n29 and n30 are respectively 0. In Formula 6-1, if (for example, when) n29 and n30 are each an integer of 2 or greater, then the multiple R 29 and R 30 each provided can all be the same, or at least one selected from the multiple R 29 and the multiple R 30 can be different.
[0338] In Formula 6-1, the descriptions defined in Formula 1 and Formula 6 can be similarly applied to R2 to R8, R a to R k 、R 42 to R 48 、Z1 and Z2.
[0339] In one or more embodiments, the fused polycyclic compound represented by Formula 1 can be represented by any one selected from Formula 7-1 to Formula 7-4.
[0340] Formula 7-1
[0341]
[0342] Formula 7-2
[0343]
[0344] Formula 7-3
[0345]
[0346] Formula 7-4
[0347]
[0348] In Formula 7-1, A can be hydrogen or deuterium. Multiple A's can all be the same or can be different from each other. For example, in some embodiments, all A's can each be hydrogen. In some embodiments, all A's can each be deuterium.
[0349] In Formula 7-2 and Formula 7-3, R x1 、R x2 、R y1 and R y2 can each independently be deuterium, a halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in one or more embodiments, R x1 、R x2 、R y1 and R y2Each may independently be a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted N-carbazolyl group, a substituted or unsubstituted phenoxazinyl group, or a substituted or unsubstituted phenothiazinyl group. In one or more embodiments, the N-carbazolyl group may refer to a carbazolyl group connected to a fused ring nucleus according to one or more embodiments via a nitrogen atom. In one or more embodiments, R x1 、R x2 、R y1 and R y2 may each independently be any one selected from the substituents represented by the previously described formulas a-1 to a-8.
[0350] In formula 7-4, R x3 、R x4 、R y3 and R y4 may each independently be hydrogen, halogen, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. In one or more embodiments, one or more of R x3 、R x4 、R y3 and R y4 may independently bond to an adjacent group to form a ring. For example, in some embodiments, adjacent R x3 and R x4 bond to each other to form an additional heterocycle. In some embodiments, adjacent R y3 and R y4 bond to each other to form an additional heterocycle.
[0351] In formulas 7-1 to 7-4, the descriptions defined in formula 1 may be similarly applied to X, Z, R1 to R8, R a to R c and R 31 to R 36 .
[0352] In one or more embodiments, the fused polycyclic compound represented by formula 1 may be represented by formula 8-1 or formula 8-2.
[0353] Formula 8-1
[0354]
[0355] Formula 8-2
[0356]
[0357] In Formula 8-1, A can be hydrogen or deuterium. A plurality of A's can all be the same or can be different from each other. For example, in one or more embodiments, all of the A's can be hydrogen. In one or more embodiments, each of the A's can be deuterium.
[0358] In Formula 8-2, R z can be deuterium, a halogen, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. In one or more embodiments, R z may not be bonded to an adjacent group to form a ring. For example, in one or more embodiments, R z can be a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbonyl group, or a substituted or unsubstituted carbazolyl group. In one or more embodiments, R z can be an unsubstituted methyl group, an unsubstituted isopropyl group, or an unsubstituted tert-butyl group, or can be any one selected from the substituents represented by Formulae b-1 to b-9 described previously.
[0359] In Formula 8-1 and Formula 8-2, the descriptions defined in Formula 1 can be similarly applied to X, Z, R1 to R8, R d to R k and R 31 to R 36 .
[0360] In one or more embodiments, the fused polycyclic compound represented by Formula 1 according to one or more embodiments can include at least one deuterium as a substituent. The fused polycyclic compound represented by Formula 1 according to one or more embodiments can include a structure in which at least one hydrogen is substituted with deuterium.
[0361] The fused polycyclic compound according to one or more embodiments can be any one selected from the compounds present in Compound Group 1. At least one functional layer included in the light-emitting element ED according to one or more embodiments can include at least one fused polycyclic compound selected from the compounds present in Compound Group 1. The light-emitting element ED according to one or more embodiments can include at least one fused polycyclic compound selected from the compounds present in Compound Group 1 in the emission layer EML.
[0362] Compound Group 1
[0363]
[0364]
[0365]
[0366]
[0367]
[0368]
[0369]
[0370]
[0371]
[0372]
[0373]
[0374]
[0375] Among the exemplary compounds present in Compound Group 1, "D" refers to deuterium. "Ph" refers to unsubstituted phenyl. "Me" refers to methyl. "C6D5" refers to phenyl substituted with deuterium. "CD3" refers to methyl substituted with deuterium.
[0376] The emission spectrum of the fused polycyclic compound represented by Formula 1 according to one or more embodiments has a full width at half maximum (FWHM) of about 10 nm to about 50 nm or about 20 nm to about 40 nm. Since the FWHM of the emission spectrum of the first dopant / first compound represented by Formula 1 according to one or more embodiments falls within the above range, when (for example, when) the fused polycyclic compound represented by Formula 1 according to one or more embodiments is applied to a light-emitting element, the light-emitting element can have improved luminous efficiency. Additionally, when (for example, when) the fused compound according to one or more embodiments is used as a material for a blue light-emitting element, the element lifetime of the light-emitting element can be improved.
[0377] In one or more embodiments, the fused polycyclic compound represented by Formula 1 according to one or more embodiments can be a thermally activated delayed fluorescence emitting material. In one or more embodiments, the fused polycyclic compound represented by Formula 1 according to one or more embodiments can be the energy difference (ΔE) between the lowest excited triplet energy level (T1 level) and the lowest excited singlet energy level (S1 level) ST) is a thermally activated delayed fluorescence dopant of about 0.6 eV or less. In one or more embodiments, the fused polycyclic compound represented by Formula 1 according to one or more embodiments may have an energy difference (ΔE ST ) is a thermally activated delayed fluorescence dopant of about 0.2 eV or less. However, the embodiments of the present disclosure are not limited thereto.
[0378] In one or more embodiments, the fused polycyclic compound represented by Formula 1 according to one or more embodiments may include a first substituent and a second substituent within the compound. By controlling the number and position of substitution of the first substituent and the second substituent, the energy levels of the singlet state and the triplet state of the overall compound can be appropriately or suitably adjusted. Therefore, the fused polycyclic compound represented by Formula 1 according to one or more embodiments may have improved thermally activated delayed fluorescence characteristics.
[0379] The fused polycyclic compound represented by Formula 1 according to one or more embodiments may be a luminescent material having an emission peak wavelength in the wavelength region of about 430 nm to about 490 nm. For example, the fused polycyclic compound represented by Formula 1 according to one or more embodiments may be a blue thermally activated delayed fluorescence (TADF) dopant. However, the embodiments of the present disclosure are not limited thereto, and if (e.g., when) the fused polycyclic compound represented by Formula 1 according to one or more embodiments is used as a luminescent material, then the first dopant / first compound may be used as a dopant material, such as a red luminescent dopant or a green luminescent dopant that emits light in one or more appropriate wavelength regions.
[0380] In a light-emitting element ED according to one or more embodiments, the emission layer EML may emit delayed fluorescence. For example, in one or more embodiments, the emission layer EML may emit thermally activated delayed fluorescence (TADF).
[0381] In one or more embodiments, the emission layer EML of the light-emitting element ED may emit blue light. For example, the emission layer EML of the light-emitting element ED may emit blue light in the wavelength region of about 490 nm or less. However, the embodiments of the present disclosure are not limited thereto, and the emission layer EML may emit green light or red light.
[0382] In one or more embodiments, the fused polycyclic compound represented by Formula 1 according to one or more embodiments may be included in the emission layer EML. The fused polycyclic compound represented by Formula 1 according to one or more embodiments may be included in the emission layer EML as a dopant material. The fused polycyclic compound represented by Formula 1 according to one or more embodiments may be a thermally activated delayed fluorescence material. The fused polycyclic compound represented by Formula 1 according to one or more embodiments may be used as a thermally activated fluorescent dopant. For example, in a light-emitting device ED according to one or more embodiments, the emission layer EML may include at least one of the fused polycyclic compounds present in the previously described Compound Group 1 as a thermally activated delayed fluorescence dopant. However, the use of the fused polycyclic compound represented by Formula 1 according to one or more embodiments is not limited thereto.
[0383] In one or more embodiments, the light-emitting layer EML (i.e., the emission layer EML) may include a plurality of compounds. The light-emitting layer EML of one or more embodiments may include the fused polycyclic compound represented by Formula 1, i.e., the first compound. In addition, the light-emitting layer EML of one or more embodiments may include a second compound represented by Formula HT-1 and / or a third compound represented by Formula ET-1, and may further include a fourth compound represented by Formula D-1.
[0384] In one or more embodiments, the emission layer EML may include the first compound represented by Formula 1, and may further include at least one of the second compound represented by Formula HT-1, the third compound represented by Formula ET-1, and the fourth compound represented by Formula D-1.
[0385] In one or more embodiments, the second compound may be used as a hole-transporting host material for the emission layer EML.
[0386] Formula HT-1
[0387]
[0388] In Formula HT-1, M1 to M8 may each independently be N or CR 51 . For example, in one or more embodiments, all of M1 to M8 may be CR 51 . In one or more embodiments, any one selected from M1 to M8 may be N, and the remaining groups may be CR 51 .
[0389] In formula HT-1, L1 can be a direct bond, a substituted or unsubstituted arylene having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 30 ring carbon atoms. For example, in one or more embodiments, L1 can be a direct bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted divalent biphenyl, and / or a substituted or unsubstituted divalent carbazolyl, etc., but the embodiments of the present disclosure are not limited thereto.
[0390] In formula HT-1, Y a can be a direct bond, CR 52 R 53 or SiR 54 R 55 . For example, it can mean that two six-membered rings (e.g., two benzene rings) connected to the nitrogen atom in formula HT-1 are directly connected, connected. In one or more embodiments, in formula HT-1, if (e.g., when) Y a is a direct bond, the second compound represented by formula HT-1 can include a carbazole moiety.
[0391] In formula HT-1, Ar a can be a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms. For example, in one or more embodiments, Ar a can be a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, and / or a substituted or unsubstituted biphenyl, etc., but the embodiments of the present disclosure are not limited thereto.
[0392] In formula HT-1, R 51 to R 55 can each independently be hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted silyl, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 60 ring carbon atoms. In one or more embodiments, one or more selected from R 51 to R 55 can each independently bond to an adjacent group to form a ring. For example, in one or more embodiments, R 51 to R 55 can each independently be hydrogen or deuterium. In one or more embodiments, R 51 to R 55Each may independently be an unsubstituted methyl or an unsubstituted phenyl.
[0393] In one or more embodiments, the second compound represented by formula HT-1 may be any one selected from the compounds represented by Compound Group 2. The emission layer EML may include at least one of the compounds represented by Compound Group 2 as a hole transport host material.
[0394] Compound Group 2
[0395]
[0396]
[0397]
[0398] In the embodiment compounds present in Compound Group 2, "D" may refer to deuterium, and "Ph" may refer to a substituted or unsubstituted phenyl. For example, in the embodiment compounds present in Compound Group 2, "Ph" may refer to an unsubstituted phenyl.
[0399] In one or more embodiments, the emission layer EML may include a third compound represented by formula ET-1. For example, the third compound may be used as an electron transport host material for the emission layer EML.
[0400] Formula ET-1
[0401]
[0402] In formula ET-1, at least one selected from Z a to Z c may be N, and the remaining groups are CR 56 . For example, in one or more embodiments, any one selected from Z a to Z c (for example, one selected from Z a to Z c ) may be N, and the remaining groups (i.e., the remaining or unselected groups) may each independently be CR 56 . In those embodiments, the third compound represented by formula ET-1 may include a pyridine moiety. In one or more embodiments, two of the groups selected from Z a to Z c may be N, and the remaining groups may be CR 56 . In those embodiments, the third compound represented by formula ET-1 may include a pyrimidine moiety. In one or more embodiments, Z a to Z cIt may all be N. In those embodiments, the third compound represented by Formula ET-1 may include a triazine moiety.
[0403] In Formula ET-1, R 56 may be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms.
[0404] In Formula ET-1, b1 to b3 may each independently be an integer selected from 0 to 10.
[0405] In Formula ET-1, Ar b to Ar d may each independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in one or more embodiments, Ar b to Ar d may each independently be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazolyl group.
[0406] In Formula ET-1, L2 to L4 may each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In one or more embodiments, if (e.g., when) b1 to b3 are each an integer of 2 or greater, then L2 to L4 may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0407] In one or more embodiments, the third compound may be any one of the compounds selected from Compound Group 3. The light-emitting device ED of one or more embodiments may include at least one of the compounds selected from Compound Group 3.
[0408] Compound Group 3
[0409]
[0410]
[0411]
[0412] In the embodiment compounds presented in Compound Group 3, "D" refers to deuterium, and "Ph" refers to an unsubstituted phenyl group.
[0413] In one or more embodiments, the emission layer EML may include a second compound and a third compound, and the second compound and the third compound may form an exciplex. In the emission layer EML, the exciplex may be formed by a hole-transporting host and an electron-transporting host. In these embodiments, the triplet energy level of the exciplex formed by the hole-transporting host and the electron-transporting host may correspond to the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the electron-transporting host and the highest occupied molecular orbital (HOMO) energy level of the hole-transporting host.
[0414] For example, in one or more embodiments, the absolute value of the lowest excited triplet energy level (T1 energy level) of the exciplex formed by the hole-transporting host and the electron-transporting host may be from about 2.4 eV to about 3.0 eV. Additionally, the lowest excited triplet energy level (T1 energy level) of the exciplex may be a value less than the energy gap of each host material. The exciplex may have a lowest excited triplet energy level (T1 energy level) of about 3.0 eV or less, which is the energy gap between the hole-transporting host and the electron-transporting host.
[0415] In one or more embodiments, in addition to the first compound to the third compound as described above, the emission layer EML may include a fourth compound. The fourth compound may be used as a sensitizer for the emission layer EML. Energy may be transferred from the fourth compound to the first compound, thereby emitting light.
[0416] For example, in one or more embodiments, the emission layer EML may include an organometallic complex as the fourth compound, the organometallic complex containing platinum (Pt) as a central metal atom and ligands attached to the central metal atom. The emission layer EML in the light-emitting device ED of one or more embodiments may include a compound represented by Formula D-1 as the fourth compound:
[0417] Formula D-1
[0418]
[0419] In Formula D-1, Q1 to Q4 may each independently be C or N.
[0420] In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms.
[0421] In Formula D-1, L 11 to L 13 may each independently be a direct bond, *-O-*, *-S-*, A substituted or unsubstituted alkylene having 1 to 20 carbon atoms, a substituted or unsubstituted arylene having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 30 ring-forming carbon atoms. In L 11 to L 13 ,"-*" refers to a moiety linked to C1 to C4.
[0422] In formula D-1, b11 to b13 can each independently be 0 or 1. If (for example, when) b11 is 0, then C1 and C2 may not be connected to each other. If (for example, when) b12 is 0, then C2 and C3 may not be connected to each other. If (for example, when) b13 is 0, then C3 and C4 may not be connected to each other.
[0423] In formula D-1, R 61 to R 66 can each independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thio, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boryl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 60 ring-forming carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 60 ring-forming carbon atoms. In one or more embodiments, one or more selected from R 61 to R 66 can independently bond to an adjacent group to form a ring. In one or more embodiments, R 61 to R 66 can each independently be substituted or unsubstituted methyl or substituted or unsubstituted tert-butyl.
[0424] In formula D-1, d1 to d4 can each independently be an integer selected from 0 to 4. In formula D-1, if each of d1 to d4 is 0, then the fourth compound may not be substituted by each of R 61 to R 64 . Wherein each of d1 to d4 is 4 and R 61 to R 64 are each hydrogen may be the same as the embodiment wherein each of d1 to d4 is 0. When each of d1 to d4 is an integer of 2 or greater, then multiple R 61 to multiple R 64 can each be the same or at least one selected from multiple R 61 to multiple R 64 can be different from each other.
[0425] In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group or a substituted or unsubstituted heterocyclic group represented by any one selected from C-1 to C-4:
[0426]
[0427] In C-1 to C-4, P1 may be C-* or CR 74 , P2 may be N-* or NR 81 , P3 may be N-* or NR 82 , and P4 may be C-* or CR 88 . R 71 to R 88 may each independently be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may be bonded to an adjacent group to form a ring.
[0428] In addition, in C-1 to C-4, corresponds to the portion connected to Pt as the central metal atom, and "-*" corresponds to the portion connected to the adjacent cyclic groups C1 to C4 or the linker L 11 to L 13 .
[0429] The emission layer EML of one or more embodiments may include a first compound that is a fused polycyclic compound of the present disclosure and at least one selected from second to fourth compounds. For example, in one or more embodiments, the emission layer EML may include a first compound, a second compound, and a third compound. In the emission layer EML, the second compound and the third compound may form an exciplex, and energy may be transferred from the exciplex to the first compound to emit light.
[0430] In one or more embodiments, the emission layer EML may include a first compound, a second compound, a third compound, and a fourth compound. In the emission layer EML, the second compound and the third compound may form an exciplex, and energy may be transferred from the exciplex to the fourth compound and the first compound, thereby emitting light. In one or more embodiments, the fourth compound may be a sensitizer. The fourth compound included in the emission layer EML in the light-emitting element ED of one or more embodiments may be used as a sensitizer to transfer energy from the host to the first compound as a light-emitting dopant. For example, in some embodiments, the fourth compound used as a co-dopant accelerates the energy transfer to the first compound as a light-emitting dopant, thereby increasing the emission ratio of the first compound. Therefore, the emission layer EML of one or more embodiments may improve the light-emitting efficiency. Additionally, if (e.g., when) the energy transferred to the first compound increases, the excitons formed in the emission layer EML do not accumulate inside the emission layer EML and emit light quickly, and thus the degradation of the element may be reduced. Therefore, the element lifespan of the light-emitting element ED of one or more embodiments may be increased.
[0431] The light-emitting element ED of one or more embodiments may include all of the first compound, the second compound, the third compound, and the fourth compound, and the emission layer EML may include a combination of two host materials and two dopant materials. In the light-emitting element ED of one or more embodiments, the emission layer EML may simultaneously (e.g., synchronously) include the second compound and the third compound as two different hosts, the first compound that emits delayed fluorescence, and the fourth compound that is an organometallic complex, thereby exhibiting excellent or appropriate light-emitting efficiency characteristics.
[0432] In one or more embodiments, the fourth compound represented by Formula D-1 may include at least one selected from the compounds represented in Compound Group 4. The emission layer EML may include at least one selected from the compounds represented in Compound Group 4 as a sensitizer.
[0433] Compound Group 4
[0434]
[0435]
[0436] In the embodiment compounds present in Compound Group 4, "D" refers to deuterium.
[0437] When the emission layer EML in the light-emitting element ED of one or more embodiments includes all of the first compound, the second compound, the third compound, and the fourth compound, the content (e.g., amount) of the first compound may be about 0.1 wt% to about 5 wt% relative to the total weight (100 wt%) of the first compound, the second compound, the third compound, and the fourth compound. However, the embodiments of the present disclosure are not limited thereto. When the content (e.g., amount) of the first compound satisfies the above ratio, the energy transfer from the second compound and the third compound to the first compound can be increased, and thus the luminous efficiency and the element service life can be increased.
[0438] The content (e.g., amount) of the second compound and the third compound in the emission layer EML may be the remaining part excluding the weights of the first compound and the fourth compound. For example, relative to the total weight of 100 wt% of the first compound, the second compound, the third compound, and the fourth compound, the content of the second compound and the third compound in the emission layer EML may be about 65 wt% to about 95 wt%.
[0439] In the total weight of the second compound and the third compound, the weight ratio of the second compound to the third compound may be about 3:7 to about 7:3.
[0440] When the content of the second compound and the third compound satisfies the above ratio, the charge balance characteristics in the emission layer EML are improved, and thus the luminous efficiency and the element service life can be increased. When the content of the second compound and the third compound deviates from the above ratio range, the charge balance in the emission layer EML is broken, and thus the luminous efficiency can be reduced, and the light-emitting element ED can be easily deteriorated.
[0441] In one or more embodiments, when the emission layer EML further includes the fourth compound, the content (e.g., amount) of the fourth compound in the emission layer EML may be about 10 wt% to about 30 wt% relative to the total weight of 100 wt% of the first compound, the second compound, the third compound, and the fourth compound. However, the embodiments of the present disclosure are not limited thereto. When the content (e.g., amount) of the fourth compound satisfies the above content (e.g., amount), the energy transferred from the host to the first compound as a light-emitting dopant can be increased, thereby improving the emission ratio, and thus the luminous efficiency of the emission layer EML can be improved. When the first compound, the second compound, the third compound, and the fourth compound included in the emission layer EML satisfy the above content (e.g., amount) ratio range, excellent or appropriate luminous efficiency and long element service life of the light-emitting element can be achieved.
[0442] In the light-emitting element ED of one or more embodiments, the emission layer EML may include an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a 1,2-benzophenanthrene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. For example, in some embodiments, the emission layer EML may include one or more anthracene derivatives or one or more pyrene derivatives.
[0443] In Figures 3 to 6 each light-emitting element ED of the embodiments illustrated, in addition to the above host and dopant, the emission layer EML may further include a suitable host and dopant, and for example, in some embodiments, the emission layer EML may include a compound represented by Formula E-1. The compound represented by Formula E-1 can be used as a fluorescent host material.
[0444] Formula E-1
[0445]
[0446] In Formula E-1, R 31 to R 40 may each independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may be bonded to an adjacent group to form a ring. In one or more embodiments, one or more selected from R 31 to R 40 may each independently be bonded to an adjacent group to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocycle, or an unsaturated heterocycle.
[0447] In Formula E-1, c and d may each independently be an integer selected from 0 to 5.
[0448] The compound represented by Formula E-1 may be any one selected from Compound E1 to Compound E19:
[0449]
[0450]
[0451] In one or more embodiments, the emission layer EML may include a compound represented by Formula E-2a or Formula E-2b. The compound represented by Formula E-2a or Formula E-2b can be used as a phosphorescent host material.
[0452] Formula E-2a
[0453]
[0454] In formula E-2a, a can be an integer selected from 0 to 10, and L a can be a direct bond, a substituted or unsubstituted arylene having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene having 2 to 30 ring carbon atoms. In one or more embodiments, if (e.g., when) a is an integer of 2 or greater, then multiple L a can each independently be a substituted or unsubstituted arylene having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene having 2 to 30 ring carbon atoms.
[0455] In addition, in formula E-2a, A1 to A5 can each independently be N or CR i . R a to R i can each independently be hydrogen, deuterium, a substituted or unsubstituted amino group, a substituted or unsubstituted sulfide group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or can bond to an adjacent group to form a ring. In one or more embodiments, one or more selected from R a to R i can independently bond to an adjacent group to form a hydrocarbon ring group or a heterocyclic group containing N, O, and / or S etc. as ring atoms.
[0456] In one or more embodiments, in formula E-2a, two or three selected from A1 to A5 can be N, and the remaining groups can be CR i .
[0457] Formula E-2b
[0458]
[0459] In formula E-2b, Cbz1 and Cbz2 can each independently be an unsubstituted carbazolyl group or a carbazolyl group substituted with an aryl group having 6 to 30 ring carbon atoms. L b can be a direct bond, a substituted or unsubstituted arylene having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene having 2 to 30 ring carbon atoms. In one or more embodiments, b can be an integer selected from 0 to 10, and if (e.g., when) b is an integer of 2 or greater, then multiple L b can each independently be a substituted or unsubstituted arylene having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene having 2 to 30 ring carbon atoms.
[0460] The compound represented by Formula E-2a or Formula E-2b can be any one of the compounds selected from the group of compounds E-2. However, the compounds listed in the group of compounds E-2 are only examples, and the compounds represented by Formula E-2a or Formula E-2b are not limited to those represented in the group of compounds E-2.
[0461] Group of compounds E-2
[0462]
[0463]
[0464] In one or more embodiments, the emission layer EML may further include a material suitable in the art as a host material. For example, the emission layer EML may include at least one of bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis(carbazol-9-yl)benzene (mCP), 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF), 4,4',4”-tris(carbazol-9-yl)triphenylamine (TCTA), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) as a host material. However, the embodiments of the present disclosure are not limited thereto. For example, tris(8-hydroxyquinoline)aluminum (Alq3), 9,10-bis(naphthalen-2-yl)anthracene (ADN), 2-tert-butyl-9,10-bis(naphthalen-2-yl)anthracene (TBADN), distyrylarylene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), and / or octaphenylcyclotetrasiloxane (DPSiO4), etc. can be used as a host material.
[0465] In one or more embodiments, the emission layer EML may include a compound represented by Formula M-a. The compound represented by Formula M-a can be used as a phosphorescent dopant material.
[0466] Formula M-a
[0467]
[0468] In formula M-a, Y1 to Y4 and Z1 to Z4 can each independently be CR1 or N, and R1 to R4 can each independently be hydrogen, deuterium, a substituted or unsubstituted amino group, a substituted or unsubstituted sulfanyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or can be bonded to adjacent groups to form a ring. In formula M-a, m is 0 or 1, and n is 2 or 3. In formula M-a, if (for example, when) m is 0, then n is 3, and if (for example, when) m is 1, then n is 2.
[0469] The compound represented by formula M-a can be used as a phosphorescent dopant.
[0470] The compound represented by formula M-a can be any one selected from Compound M-a1 to Compound M-a25. However, Compound M-a1 to Compound M-a25 are only examples, and the compound represented by formula M-a is not limited to those compounds represented by Compound M-a1 to Compound M-a25.
[0471]
[0472]
[0473]
[0474] In one or more embodiments, the emission layer EML can include a compound represented by any one selected from formula F-a to formula F-c. The compounds represented by formula F-a to formula F-c can be used as fluorescent dopant materials.
[0475] Formula F-a
[0476]
[0477] In formula F-a, two of the selected R a to R j can each independently be substituted by *-NAr1Ar2. The other groups among R a to R j that are not substituted by *-NAr1Ar2 can each independently be hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
[0478] In *-NAr1Ar2, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms. For example, in some embodiments, at least one of Ar1 and Ar2 may be a heteroaryl containing O or S as a ring atom.
[0479] Formula F-b
[0480]
[0481] In formula F-b, R a and R b may each independently be hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and / or may be bonded to an adjacent group to form a ring. Ar1 to Ar4 may each independently be a substituted or unsubstituted aryl having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms.
[0482] In formula F-b, U and V may each independently be a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms. In some embodiments, at least one selected from Ar1 to Ar4 may be a heteroaryl containing O or S as a ring atom.
[0483] In formula F-b, the number of rings represented by U and V may each independently be 0 or 1. For example, in formula F-b, it means that if (for example, when) the number of U or V is 1, then one ring forms part of a fused ring in the part indicated by U or V, and if (for example, when) the number of U or V is 0, then the ring indicated by U or V does not exist. For example, if (for example, when) the number of U is 0 and the number of V is 1, or if (for example, when) the number of U is 1 and the number of V is 0, then the fused ring having a fluorene nucleus in formula F-b may be a cyclic compound having four rings. In one or more embodiments, if (for example, when) the number of each of U and V is 0, then the fused ring having a fluorene nucleus in formula F-b may be a cyclic compound having three rings. In one or more embodiments, if (for example, when) the number of each of U and V is 1, then the fused ring having a fluorene nucleus in formula F-b may be a cyclic compound having five rings.
[0484] Formula F-c
[0485]
[0486] In formula F-c, A1 and A2 can each independently be O, S, Se or NR m , and R m can be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. R1 to R 11 can each independently be hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or can be bonded to an adjacent group to form a ring.
[0487] In one or more embodiments, in formula F-c, A1 and A2 can each independently be bonded to a substituent of an adjacent ring to form a fused ring. For example, if (e.g., when) A1 and A2 can each independently be NR m , then A1 can be bonded to R4 or R5 to form a ring. Additionally, A2 can be bonded to R7 or R8 to form a ring.
[0488] In one or more embodiments, the emissive layer EML can further include one or more selected from the following as suitable dopant materials: styryl derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi), and 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), and / or pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene), etc.
[0489] In one or more embodiments, the emissive layer EML may further include a suitable phosphorescent dopant material. For example, metal complexes containing iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) may be used as phosphorescent dopants. For example, bis(4,6-difluorophenylpyridinato-N,C2)iridium(III) picolinate (FIrpic), bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III) (FIr6), or platinum octaethylporphyrin (PtOEP) may be used as phosphorescent dopants. However, the embodiments of the present disclosure are not limited thereto.
[0490] In one or more embodiments, the emissive layer EML may include a quantum dot material. In one or more embodiments, the quantum dots may have a core / shell structure. The core of the quantum dots may be selected from group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and / or combinations thereof (e.g., any suitable combination).
[0491] The group II-VI compounds may be selected from the group consisting of: binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof (e.g., any suitable mixture); ternary compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, and mixtures thereof (e.g., any suitable mixture); and quaternary compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and mixtures thereof (e.g., any suitable mixture).
[0492] The group III-VI compounds may include: binary compounds such as In2S3 and / or In2Se3; ternary compounds such as InGaS3 and / or InGaSe3, or any combination thereof.
[0493] The Group I-III-VI compounds may be selected from: ternary compounds selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2, and mixtures thereof (e.g., any suitable mixture); and / or quaternary compounds such as AgInGaS2 or CuInGaS2.
[0494] The Group III-V compounds may be selected from the group consisting of: binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof (e.g., any suitable mixture); ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof (e.g., any suitable mixture); and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof (e.g., any suitable mixture). In one or more embodiments, the Group III-V compounds may further include Group II metals. For example, InZnP etc. may be selected as the Group III-II-V compounds.
[0495] The Group IV-VI compounds may be selected from the group consisting of: binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof (e.g., any suitable mixture); ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof (e.g., any suitable mixture); and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof (e.g., any suitable mixture). The Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof (e.g., any suitable mixture). The Group IV compounds may be binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof (e.g., any suitable mixture).
[0496] Each element included in a multi-component compound (such as a binary compound, a ternary compound, or a quaternary compound) may be present in the particles in a substantially uniform or non-uniform concentration distribution. For example, the general formula refers to the type (species) of elements included in the compound, and the elemental ratios in the compound may vary. For example, AgInGaS2 may refer to AgIn x Ga 1-x S2 (where 0 < x < 1).
[0497] In one or more embodiments, the quantum dots may have a single structure or a core / shell dual structure in which the concentration of each element included in the quantum dots is substantially uniform. For example, the material included in the core may be different from the material included in the shell.
[0498] The shell of the quantum dots can be used as a protective layer to prevent or reduce the chemical denaturation of the core to maintain semiconductor properties, and / or a charge layer to impart electrophoretic properties to the quantum dots. The shell can be a single layer or multiple layers. The interface between the core and the shell may have a concentration gradient, where the concentration of the elements present in the shell becomes lower towards the center of the core.
[0499] In one or more embodiments, the quantum dots may have the above-described core / shell structure, which includes a core containing nanocrystals and a shell around the core (e.g., surrounding the core). Examples of the shell of the quantum dots may include metal oxides or non-metal oxides, semiconductor compounds, and / or combinations thereof (e.g., any suitable combination).
[0500] For example, the metal oxide or non-metal oxide used for the shell may be: binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and / or NiO; and / or ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and / or CoMn2O4, but the embodiments of the present disclosure are not limited thereto.
[0501] And, examples of semiconductor compounds suitable as the shell may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, and / or AlSb, etc., but the embodiments of the present disclosure are not limited thereto.
[0502] Each element included in a multi-component compound (such as a binary compound or a ternary compound) may be present in the particles in a substantially uniform or non-uniform concentration distribution. For example, the formula refers to the type (species) of elements included in the compound, and the elemental ratios in the compound may vary.
[0503] The quantum dots may have a full width at half maximum (FWHM) of the emission spectrum of about 45 nm or less, about 40 nm or less, or about 30 nm or less, and within the above ranges, the color purity or color reproducibility of the quantum dots can be improved. In addition, the light emitted by such quantum dots is emitted in all directions so that the wide viewing angle can be improved.
[0504] In addition, although the form (or shape) of the quantum dots is not particularly limited as long as it is a form commonly used in the art, in one or more embodiments, quantum dots in the form of spherical nanoparticles, cone nanoparticles, multi-arm nanoparticles, or cube nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates, etc. can be used.
[0505] When adjusting the size of the quantum dots or the element ratio in the quantum dot compound, the bandgap of the quantum dots can be controlled, and thus light within one or more appropriate wavelength ranges can be obtained in the quantum dot emission layer. Therefore, the quantum dots as described above (using quantum dots of different sizes or quantum dot compounds with different element ratios) can be used, and thus a light-emitting element that emits light within one or more appropriate wavelength ranges can be realized. For example, adjusting the size of the quantum dots and / or the element ratio in the quantum dot compound can ensure that the quantum dots emit red, green, and / or blue light. In one or more embodiments, the quantum dots can be configured to emit white light by combining light of one or more appropriate colors.
[0506] In Figures 3 to 6 each of the light-emitting elements ED in the embodiments illustrated in, an electron transport region ETR can be provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the embodiments of the present disclosure are not limited thereto.
[0507] The electron transport region ETR may have: a single-layer structure including a single layer formed of a single material, a single-layer structure including a single layer formed of a plurality of different materials, or a multi-layer structure including a plurality of layers formed of a plurality of different materials.
[0508] For example, in one or more embodiments, the electron transport region ETR may have a single-layer structure of an electron injection layer EIL or an electron transport layer ETL, or may have a single-layer structure formed of an electron injection material and an electron transport material. In one or more embodiments, the electron transport region ETR may have a single-layer structure formed of a plurality of different materials, or may have a structure in which the electron transport layer ETL / electron injection layer EIL or the hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL is stacked in order (e.g., in the recited order) from the emission layer EML, but the embodiments of the present disclosure are not limited thereto. The electron transport region ETR may have, for example, about to about in thickness.
[0509] The electron transport region ETR can be formed using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir - Blodgett (LB) method, inkjet printing, laser printing, and / or laser induced thermal imaging (LITI) method.
[0510] In one or more embodiments, the electron transport region ETR can include a compound represented by Formula ET - 2:
[0511] Formula ET - 2
[0512]
[0513] In Formula ET - 2, at least one selected from X1 to X3 can be N, and the remaining groups are CR a . R a can be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring - forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring - forming carbon atoms. Ar1 to Ar3 can each independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring - forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring - forming carbon atoms.
[0514] In Formula ET - 2, a to c can each independently be an integer selected from 0 to 10. In Formula ET - 2, L1 to L3 can each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring - forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring - forming carbon atoms. In one or more embodiments, if (for example, when) a to c can each independently be an integer of 2 or greater, then L1 to L3 can each independently be a substituted or unsubstituted arylene group having 6 to 30 ring - forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring - forming carbon atoms.
[0515] In one or more embodiments, the electron transport region (ETR) may include an anthracene compound. However, embodiments of the present disclosure are not limited thereto. For example, in some embodiments, the electron transport region (ETR) may include, for example, at least one selected from the following: tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridinyl)-benzene-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthoanthracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(biphenyl-4-yl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole t (Bu-PBD), bis(2-methyl-8-hydroxyquinolinato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum (BAlq), bis(benzoquinolinato-10-hydroxy)beryllium (Bebq2), 9,10-di(naphthalen-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB), and / or a mixture thereof (e.g., any suitable mixture) (or combination).
[0516] In one or more embodiments, the electron transport region (ETR) may include at least one selected from Compounds ET1 to ET36:
[0517]
[0518]
[0519]
[0520] In one or more embodiments, the electron transport region (ETR) may include metal halides such as LiF, NaCl, CsF, RbCl, RbI, CuI, and / or KI, lanthanide metals such as Yb, or co-deposited materials of metal halides and lanthanide metals. For example, in some embodiments, the electron transport region (ETR) may include KI:Yb, RbI:Yb, and / or LiF:Yb, etc. as co-deposited materials. In one or more embodiments, the electron transport region (ETR) may be formed using metal oxides such as Li2O and / or BaO, or lithium 8-hydroxyquinolate (Liq), etc., but the embodiments of the present disclosure are not limited thereto. In some embodiments, the electron transport region (ETR) may also be formed of a mixture material of an electron transport material and an insulating organometallic salt. The insulating organometallic salt may be a material having a band gap of about 4 eV or greater. For example, the insulating organometallic salt may include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates.
[0521] In one or more embodiments, in addition to one or more of the above materials, the electron transport region (ETR) may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and 4,7-diphenyl-1,10-phenanthroline (Bphen), but the embodiments of the present disclosure are not limited thereto.
[0522] The electron transport region (ETR) may include one or more of the above compounds of the electron transport region (ETR) in at least one of the electron injection layer (EIL), the electron transport layer (ETL), or the hole blocking layer (HBL).
[0523] When the electron transport region (ETR) includes the electron transport layer (ETL), the electron transport layer (ETL) may have a thickness of about to about For example, about to about . If the thickness of the electron transport layer (ETL) satisfies the foregoing range, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage. When the electron transport region (ETR) includes the electron injection layer (EIL), the electron injection layer (EIL) may have a thickness of about to about For example, about to about . If the thickness of the electron injection layer (EIL) satisfies the above range, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0524] The second electrode EL2 may be provided over the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but embodiments of the present disclosure are not limited thereto. For example, if (e.g., when) the first electrode EL1 is an anode, then the second electrode EL2 may be a cathode, and if (e.g., when) the first electrode EL1 is a cathode, then the second electrode EL2 may be an anode. The second electrode may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, a compound of two or more selected therefrom, a mixture of two or more selected therefrom, or an oxide thereof.
[0525] The second electrode EL2 may be a transmissive electrode, a transmissive-reflective electrode, or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may be formed of a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO), etc.
[0526] When the second electrode EL2 is a transmissive-reflective electrode or a reflective electrode, the second electrode EL2 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, and W, a (e.g., any suitable) compound or a mixture (e.g., any suitable mixture) thereof (e.g., AgMg, AgYb, or MgYb), or a material having a multilayer structure such as LiF / Ca (a stacked structure of LiF and Ca) or LiF / Al (a stacked structure of LiF and Al). In one or more embodiments, the second electrode EL2 may have a multilayer structure including a reflective film or a transmissive-reflective film formed of one or more of the above materials and a transparent conductive film formed of ITO, IZO, ZnO, and / or ITZO, etc. For example, the second electrode EL2 may include one of the above metal materials, a combination of at least two of the above metal materials, and / or one or more oxides of the above metal materials, etc.
[0527] In one or more embodiments, the second electrode EL2 may be connected to an auxiliary electrode. If (e.g., when) the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.
[0528] In one or more embodiments, a capping layer CPL may be further disposed over the second electrode EL2 of the light-emitting element ED. The capping layer CPL may include multiple layers or a single layer.
[0529] In one or more embodiments, the capping layer CPL may be an organic layer or an inorganic layer. For example, if (e.g., when) the capping layer CPL contains an inorganic material, the inorganic material may include an alkali metal compound (e.g., LiF), an alkaline earth metal compound (e.g., MgF2), SiON, SiN x and / or SiO y and the like.
[0530] For example, in some embodiments, if (e.g., when) the capping layer CPL includes an organic material, the organic material may include 2,2'-dimethyl-N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine (α-NPD), NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), and / or 4,4',4''-tris(carbazol-9-yl)triphenylamine (TCTA), etc., or an epoxy resin, or an acrylate (such as a methacrylate). However, the embodiments of the present disclosure are not limited thereto. For example, in one or more embodiments, the capping layer CPL may include at least one selected from Compound P1 to Compound P5:
[0531]
[0532]
[0533] In one or more embodiments, the refractive index of the capping layer CPL may be about 1.6 or greater. For example, in one or more embodiments, the refractive index of the capping layer CPL may be about 1.6 or greater with respect to light in the wavelength range of about 550 nm to about 660 nm.
[0534] Figures 7 to 10 Each of is a cross-sectional view of a display device according to one or more embodiments of the present disclosure. Hereinafter, when describing the display device of the embodiment with reference to Figures 7 to 10 for the sake of brevity, the repeated features already described in Figures 1 to 6 will not be described again, and their differences will be mainly described.
[0535] Referring to Figure 7 , according to one or more embodiments, the display device DD-a may include: a display panel DP including a display device layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL. In Figure 7 In one or more embodiments illustrated, the display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED, and the display device layer DP-ED may include a light-emitting device ED.
[0536] The light-emitting device ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emission layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emission layer EML, and a second electrode EL2 disposed on the electron transport region ETR. In one or more embodiments, the structure of any one of the above Figures 3 to 6 light-emitting elements may be similarly applied to the structure of the light-emitting device ED Figure 7 illustrated in
[0537] The emission layer EML of the light-emitting device ED included in the display device DD-a according to one or more embodiments may include the fused polycyclic compound represented by Formula 1 of the above one or more embodiments.
[0538] Referring to Figure 7 , the emission layer EML may be disposed in the opening OH defined by the pixel defining layer PDL. For example, the emission layer EML provided by being divided by the pixel defining layer PDL and corresponding to each of the light-emitting regions PXA-R, PXA-G, and PXA-B may emit light in substantially the same wavelength range. In the display device DD-a of one or more embodiments, the emission layer EML may emit blue light. In one or more embodiments, the emission layer EML may be provided as a common layer in the entire light-emitting regions PXA-R, PXA-G, and PXA-B.
[0539] The light control layer CCL may be disposed on the display panel DP. The light control layer CCL may include a light converter. The light converter may be a quantum dot and / or a phosphor, etc. The light converter may emit the provided light by converting its wavelength. For example, the light control layer CCL may include a layer containing quantum dots or a layer containing phosphors.
[0540] The light control layer CCL may include a plurality of light control components CCP1, CCP2, and CCP3. The light control components CCP1, CCP2, and CCP3 may be spaced apart from and / or separated from each other (e.g., spaced apart or separated).
[0541] Referring to Figure 7 , the division pattern BMP may be disposed between the light control components CCP1, CCP2, and CCP3 that are spaced apart from and / or separated from each other (e.g., spaced apart or separated), but the embodiments of the present disclosure are not limited thereto. Figure 7 It is illustrated that the division pattern BMP does not overlap with the light control components CCP1, CCP2, and CCP3. However, in some embodiments, at least a part of the edges of the light control components CCP1, CCP2, and CCP3 may overlap with the division pattern BMP.
[0542] The light control layer CCL may include a first light control component CCP1 containing a first quantum dot QD1 (which converts the first color light provided from the light emitting device ED into a second color light), a second light control component CCP2 containing a second quantum dot QD2 (which converts the first color light into a third color light), and a third light control component CCP3 that transmits the first color light.
[0543] In one or more embodiments, the first light control component CCP1 may provide red light as the second color light, and the second light control component CCP2 may provide green light as the third color light. The third light control component CCP3 may provide blue light by transmitting blue light as the first color light provided from the light emitting device ED. For example, in one or more embodiments, the first quantum dot QD1 may be a red quantum dot that emits red light, and the second quantum dot QD2 may be a green quantum dot that emits green light. The same method as the above-described quantum dots may be applied to the first quantum dot QD1 and the second quantum dot QD2.
[0544] In one or more embodiments, the light control layer CCL may further include a scatterer SP. The first light control component CCP1 may include the first quantum dot QD1 and the scatterer SP, the second light control component CCP2 may include the second quantum dot QD2 and the scatterer SP, and the third light control component CCP3 may not include (e.g., may exclude) any quantum dots, but includes the scatterer SP.
[0545] The scatterer SP may be inorganic particles. For example, the scatterer SP may include at least one of TiO2, ZnO, Al2O3, SiO2, and hollow sphere silica. In one or more embodiments, the scatterer SP may include any one selected from TiO2, ZnO, Al2O3, SiO2, and hollow sphere silica, or may be a mixture of at least two materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow sphere silica.
[0546] The first light control component CCP1, the second light control component CCP2, and the third light control component CCP3 may respectively include a base resin BR1, BR2, and BR3 in which the first quantum dot QD1, the second quantum dot QD2, and the scatterer SP are dispersed. In one or more embodiments, the first light control component CCP1 may include the first quantum dot QD1 and the scatterer SP dispersed in the first base resin BR1, the second light control component CCP2 may include the second quantum dot QD2 and the scatterer SP dispersed in the second base resin BR2, and the third light control component CCP3 may include the scatterer SP dispersed in the third base resin BR3.
[0547] The base resins BR1, BR2, and BR3 are media in which the first quantum dots QD1 and the second quantum dots QD2 and the scatterers SP are dispersed, and can be formed of one or more suitable resin compositions (which may generally be referred to as binders). For example, the base resins BR1, BR2, and BR3 can each independently be acrylic resins, urethane resins, silicone resins, and / or epoxy resins, etc. The base resins BR1, BR2, and BR3 can be transparent resins. In one or more embodiments, the first base resin BR1, the second base resin BR2, and the third base resin BR3 can be the same as or different from each other.
[0548] In one or more embodiments, the light control layer CCL can include the barrier layer BFL1. The barrier layer BFL1 can be used to prevent or reduce the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 can block the exposure of the light control components CCP1, CCP2, and CCP3 to moisture / oxygen. In one or more embodiments, the barrier layer BFL1 can cover the light control components CCP1, CCP2, and CCP3. In one or more embodiments, the barrier layer BFL2 can be provided between the light control components CCP1, CCP2, and CCP3 and the color filters CF1, CF2, and CF3.
[0549] The barrier layers BFL1 and BFL2 can include at least one inorganic layer. For example, in some embodiments, the barrier layers BFL1 and BFL2 can each include an inorganic material. For example, the barrier layers BFL1 and BFL2 can each independently include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, and / or a metal thin film that ensures light transmittance, etc. In one or more embodiments, the barrier layers BFL1 and BFL2 can further include an organic layer. The barrier layers BFL1 and BFL2 can be formed of a single layer or multiple layers.
[0550] In one or more embodiments of the display device DD-a, the color filter layer CFL can be disposed on the light control layer CCL. For example, in one or more embodiments, the color filter layer CFL can be directly disposed on the light control layer CCL. In these embodiments, the barrier layer BFL2 may not be provided.
[0551] The color filter layer CFL may include color filters CF1, CF2, and CF3. The color filter layer CFL may include a first color filter CF1 configured to transmit light of a second color, a second color filter CF2 configured to transmit light of a third color, and a third color filter CF3 configured to transmit light of a first color. For example, in one or more embodiments, the first color filter CF1 may be a red color filter, the second color filter CF2 may be a green color filter, and the third color filter CF3 may be a blue color filter. Each of the color filters CF1, CF2, and CF3 may include a polymerizable photosensitive resin and a pigment and / or a dye. The first color filter CF1 may include a red pigment and / or a red dye, the second color filter CF2 may include a green pigment and / or a green dye, and the third color filter CF3 may include a blue pigment and / or a blue dye.
[0552] In one or more embodiments, the third color filter CF3 may not include (e.g., may exclude) a pigment and / or a dye. The third color filter CF3 may include a polymerizable photosensitive resin and may not include (e.g., may exclude) any pigment and / or dye. The third color filter CF3 may be transparent. The third color filter CF3 may be formed of a transparent photosensitive resin.
[0553] Furthermore, in one or more embodiments, the first color filter CF1 and the second color filter CF2 may each be a yellow color filter. The first color filter CF1 and the second color filter CF2 may not be separated but may be provided as one color filter.
[0554] In one or more embodiments, the color filter layer CFL may further include a light-shielding member. The light-shielding member may be a black matrix. The light-shielding member may include an organic light-shielding material or an inorganic light-shielding material containing a black pigment and / or a black dye. The light-shielding member may prevent or reduce light leakage and may separate adjacent color filters CF1, CF2, and CF3.
[0555] The first to third color filters CF1, CF2, and CF3 may be respectively arranged corresponding to a red light-emitting region PXA-R, a green light-emitting region PXA-G, and a blue light-emitting region PXA-B.
[0556] In one or more embodiments, a base substrate BL may be arranged on the color filter layer CFL. The base substrate BL may be a member providing a base surface on which the color filter layer CFL and / or a light control layer CCL, etc. are arranged. The base substrate BL may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Additionally, in one or more embodiments, the base substrate BL may not be provided.
[0557] Figure 8A cross-sectional view of a part of a display device according to one or more embodiments is illustrated. In the display device DD-TD of one or more embodiments, the light-emitting device ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. The light-emitting device ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other, and a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 stacked in sequence in the thickness direction between the first electrode EL1 and the second electrode EL2. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include an emission layer EML( Figure 7 ) and a hole transport region HTR and an electron transport region ETR disposed with the emission layer EML( Figure 7 ) therebetween.
[0558] For example, the light-emitting device ED-BT included in the display device DD-TD of one or more embodiments may be a light-emitting device having a series structure and including a plurality of emission layers.
[0559] In Figure 8 one or more embodiments illustrated, all light beams emitted from the light-emitting structures OL-B1, OL-B2, and OL-B3 may be blue light. However, embodiments of the present disclosure are not limited thereto. For example, in one or more embodiments, the light beams emitted from the light-emitting structures OL-B1, OL-B2, and OL-B3 may have different wavelength ranges from each other. For example, in one or more embodiments, the light-emitting device ED-BT including a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 that emit light beams having different wavelength ranges from each other may emit white light (e.g., combined white light).
[0560] Charge generation layers CGL1 and CGL2 may be respectively disposed between two of the adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. The charge generation layers CGL1 and CGL2 may include a p-type or p-like charge (e.g., P charge) generation layer and / or an n-type or n-like charge (e.g., N charge) generation layer. At least one of the light-emitting structures OL-B1, OL-B2, or OL-B3 included in the display device DD-TD of one or more embodiments may include the fused polycyclic compound of the above one or more embodiments. For example, in one or more embodiments, at least one selected from the plurality of emission layers included in the light-emitting element ED-BT may include the fused polycyclic compound of the above one or more embodiments.
[0561] Referring to Figure 9 , the display device DD-b according to one or more embodiments may include light-emitting devices ED-1, ED-2, and ED-3 in which two emission layers are stacked. Compared with the display device DD illustrated in Figure 2 ,Figure 9 The display device DD-b described in Figure 9 is different in that each of the first to third light-emitting devices ED-1, ED-2, and ED-3 includes two emission layers stacked in the thickness direction. In each of the first to third light-emitting devices ED-1, ED-2, and ED-3, the two emission layers can emit light in substantially the same wavelength region.
[0562] In one or more embodiments, the first light-emitting device ED-1 may include a first red emission layer EML-R1 and a second red emission layer EML-R2. The second light-emitting device ED-2 may include a first green emission layer EML-G1 and a second green emission layer EML-G2. Additionally, the third light-emitting device ED-3 may include a first blue emission layer EML-B1 and a second blue emission layer EML-B2. The emission assist member OG may be disposed separately between the first red emission layer EML-R1 and the second red emission layer EML-R2, between the first green emission layer EML-G1 and the second green emission layer EML-G2, and between the first blue emission layer EML-B1 and the second blue emission layer EML-B2.
[0563] The emission assist member OG may include a single layer or multiple layers. The emission assist member OG may include a charge generation layer. In one or more embodiments, the emission assist member OG may include an electron transport region (not shown), a charge generation layer (not shown), and a hole transport region (not shown) stacked in sequence (e.g., in the recited order). The emission assist member OG may be provided as a common layer for the entire first to third light-emitting devices ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto, and the emission assist member OG may be provided by patterning within the opening OH defined by the pixel defining film PDL.
[0564] The first red emission layer EML-R1, the first green emission layer EML-G1, and the first blue emission layer EML-B1 may each be disposed between the emission assist member OG and the electron transport region ETR. The second red emission layer EML-R2, the second green emission layer EML-G2, and the second blue emission layer EML-B2 may each be disposed between the hole transport region HTR and the emission assist member OG.
[0565] For example, in one or more embodiments, the first light-emitting device ED-1 may include a first electrode EL1, a hole transport region HTR, a second red emission layer EML-R2, an emission assisting member OG, a first red emission layer EML-R1, an electron transport region ETR, and a second electrode EL2, which are stacked in sequence (e.g., in the recited order). The second light-emitting device ED-2 may include a first electrode EL1, a hole transport region HTR, a second green emission layer EML-G2, an emission assisting member OG, a first green emission layer EML-G1, an electron transport region ETR, and a second electrode EL2, which are stacked in sequence (e.g., in the recited order). The third light-emitting device ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue emission layer EML-B2, an emission assisting member OG, a first blue emission layer EML-B1, an electron transport region ETR, and a second electrode EL2, which are stacked in sequence (e.g., in the recited order).
[0566] In one or more embodiments, the optical assisting layer PL may be disposed on the display device layer DP-ED. The optical assisting layer PL may include a polarization layer. The optical assisting layer PL may be disposed on the display panel DP and control the light reflected at the display panel DP due to external light. In one or more embodiments, the optical assisting layer PL may not be provided in the display device.
[0567] Figure 9 At least one emission layer included in the display device DD-b shown in may include the fused polycyclic compound represented by Formula 1 in the above one or more embodiments. For example, in one or more embodiments, at least one of the first blue emission layer EML-B1 and the second blue emission layer EML-B2 may include the fused polycyclic compound represented by Formula 1 in one or more embodiments.
[0568] Unlike Figure 8 and Figure 9 different, Figure 10It is explained that the display device DD-c includes four light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. The light-emitting device ED-CT may include a first electrode EL1 and a second electrode EL2 facing each other, and first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 stacked between the first electrode EL1 and the second electrode EL2 in the thickness direction. The light-emitting structures OL-C1, OL-B1, OL-B2, and OL-B3 are stacked in sequence, and a charge generation layer CGL1 is disposed between the light-emitting structures OL-B1 and OL-C1, a charge generation layer CGL2 is disposed between the light-emitting structures OL-B1 and OL-B2, and a charge generation layer CGL3 is disposed between the light-emitting structures OL-B2 and OL-B3. In some embodiments, among the four light-emitting structures, the first to third light-emitting structures OL-B1, OL-B2, and OL-B3 may emit blue light, and the fourth light-emitting structure OL-C1 may emit green light. However, the embodiments of the present disclosure are not limited thereto, and the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light beams in different wavelength ranges.
[0569] The charge generation layers CGL1, CGL2, and CGL3 disposed between adjacent light-emitting structures OL-C1, OL-B1, OL-B2, and OL-B3 may include a p-type or p-like charge (e.g., P-charge) generation layer and / or an n-type or n-like charge (N-charge) generation layer.
[0570] At least one selected from the light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 included in the display device DD-c according to one or more embodiments may include the fused polycyclic compound represented by Formula 1 in the above one or more embodiments. For example, in one or more embodiments, at least one selected from the first to third light-emitting structures OL-B1, OL-B2, and OL-B3 may include the fused polycyclic compound represented by Formula 1 in the above one or more embodiments.
[0571] The above light-emitting device / component ED according to one or more embodiments of the present disclosure may include the fused polycyclic compound represented by Formula 1 in one or more embodiments in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2, and may thus exhibit excellent or appropriate light-emitting efficiency and improved element service life. For example, the fused polycyclic compound represented by Formula 1 in one or more embodiments may be included in the emission layer EML of the light-emitting device / component ED in one or more embodiments, and the light-emitting device / component ED in one or more embodiments may exhibit a long element service life.
[0572] In one or more embodiments, an electronic device may include: a display device including a plurality of light-emitting devices and a control component for controlling the display device. The electronic device according to one or more embodiments may be a device activated according to an electrical signal. The electronic device may include a display device according to one or more suitable embodiments. For example, the electronic device may include not only large electronic devices such as televisions, monitors, or outdoor billboards, but also small and medium-sized electronic devices such as personal computers, laptop computers, personal digital terminals, display devices for vehicles, game consoles, portable electronic devices, or cameras.
[0573] Figure 11 A view of a vehicle AM in which first to fourth display devices DD-1, DD-2, DD-3, and DD-4 are arranged is illustrated. At least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a configuration substantially the same as that of the display devices DD, DD-TD, DD-a, DD-b, and / or DD-c described in the reference Figure 1 , Figure 2 and Figures 7 to 10 .
[0574] Figure 11 The vehicle AM is illustrated, but this is for example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may be arranged in other transportation devices such as bicycles, motorcycles, trains, ships, and / or airplanes. Additionally, at least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 includes a configuration substantially the same as that of the display devices DD, DD-TD, DD-a, DD-b, and / or DD-c according to one or more embodiments and can be used in personal computers, laptop computers, personal digital terminals, game consoles, portable electronic devices, televisions, monitors, and / or outdoor billboards, etc. These are provided only as embodiments, and thus the display device can be used in other electronic devices unless departing from the present disclosure.
[0575] In one or more embodiments, at least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a light-emitting element ED according to one or more embodiments described in the reference Figures 3 to 6 . The light-emitting element ED according to one or more embodiments may include a fused polycyclic compound represented by Formula 1 according to one or more embodiments. At least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a light-emitting element ED including a fused polycyclic compound represented by Formula 1 according to one or more embodiments and may thus have an increased display life.
[0576] Reference Figure 11, the vehicle AM may include a steering wheel HA and a gearshift GR for driving the vehicle AM. Additionally, the vehicle AM may include a front window GL arranged to face the driver.
[0577] The first display device DD-1 may be arranged in a first area overlapping with the steering wheel HA. For example, the first display device DD-1 may be a digital instrument panel that displays first information of the vehicle AM. The first information may include a first scale indicating the driving speed of the vehicle AM, a second scale indicating the engine speed (i.e., revolutions per minute (RPM)), and / or an image indicating the fuel status, etc. The first scale and the second scale may each be indicated as a digital image.
[0578] The second display device DD-2 may be arranged in a second area facing the driver's seat and overlapping with the front window GL. The driver's seat may be a seat facing the steering wheel HA. For example, the second display device DD-2 may be a head-up display (HUD) that displays second information of the vehicle AM. The second display device DD-2 may be optically transparent. The second information may include a numerical value indicating the driving speed and may further include information such as the current time. In some embodiments, the second information of the second display device DD-2 may be projected onto the front window GL for display.
[0579] The third display device DD-3 may be arranged in a third area adjacent to the gearshift GR. For example, the third display device DD-3 may be arranged between the driver's seat and the passenger seat and may be a center information display (CID) of the vehicle AM for displaying third information. The passenger seat may be a seat separated from and / or apart from (e.g., spaced apart or separated) the driver's seat, and the gearshift GR is arranged between the passenger seat and the driver's seat. The third information may include information about traffic (e.g., navigation information), playing music or radio or video (or images), and / or the temperature inside the vehicle AM, etc.
[0580] The fourth display device DD-4 may be separated from and / or apart from (e.g., spaced apart or separated) the steering wheel HA and the gearshift GR, and may be arranged in a fourth area adjacent to the side of the vehicle AM. For example, the fourth display device DD-4 may be a digital side mirror that displays fourth information. The fourth display device DD-4 may display an image of the outside of the vehicle AM captured by a camera module CM arranged outside the vehicle AM. The fourth information may include an image of the outside of the vehicle AM.
[0581] The above first to fourth information may be examples, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may further display information about the inside and outside of the vehicle AM. The first to fourth information may each include different information. However, the embodiments of the present disclosure are not limited thereto, and a part of the first to fourth information may include the same information as each other.
[0582] Hereinafter, with reference to Examples and Comparative Examples, the fused polycyclic compound represented by Formula 1 and the light-emitting element according to one or more embodiments of the present disclosure will be described in more detail. In addition, the described Examples are only for understanding the present disclosure, and the scope of the present disclosure is not limited thereto.
[0583] Examples
[0584] 1. Synthesis of Fused Polycyclic Compound
[0585] First, the synthesis method of the fused polycyclic compound according to one or more embodiments will be described in more detail by exemplifying the synthesis methods of Compound 3, Compound 4, Compound 15, Compound 22, Compound 28, Compound 29, and Compound 54 of the Examples. In addition, the synthesis method of the fused polycyclic compound described later herein is provided as an Example, and thus the synthesis method of the fused polycyclic compound according to one or more embodiments of the present disclosure is not limited to the Examples.
[0586] (1) Synthesis of Intermediate Compounds 1a to 1c
[0587] Synthesis of Intermediate Compound 1a
[0588]
[0589] Under an argon (Ar) atmosphere, 2,6-dibromoaniline (25.1 g), 2-biphenylboronic acid (49.1 g), Pd(PPh3)4 (12.5 g), and K2CO3 (27.1 g) were placed in a 3000 mL three-necked flask, toluene (700 mL), EtOH (200 mL), and water (200 mL) were added, and the mixture was heated and refluxed for 12 hours. Then the temperature was restored to room temperature, then water was added, the product was extracted with CH2Cl2, the organic layer was collected, dried over MgSO4, and the solvent was removed by evaporation under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 31.4 g of Intermediate Compound 1a (yield: 78%). The mass number of Intermediate Compound 1a measured by fast atom bombardment mass spectrometry (FAB-MS) was 397.
[0590] Synthesis of Intermediate Compound 1b
[0591]
[0592] 2,6-Dibromo-4-tert-butylaniline (31.6 g) was used instead of 2,6-dibromoaniline, and intermediate compound 1b (33.0 g, yield 72%) was synthesized in substantially the same manner as intermediate compound 1a. The mass number of intermediate compound 1b measured by FAB-MS was 453.
[0593] Synthesis of intermediate compound 1c
[0594]
[0595] 2-Bromoaniline (17.2 g) and {2'-phenyl-[1,1'-biphenyl]-2-yl}boronic acid (33.9 g) were used instead of 2,6-dibromoaniline and 2-biphenylboronic acid, respectively, and intermediate compound 1c (16 g, yield 49%) was synthesized in substantially the same manner as intermediate compound 1a. The mass number of intermediate compound 1c measured by FAB-MS was 321.
[0596] (2) Synthesis of intermediate compounds 2a to 2e
[0597] Synthesis of intermediate compound 2a
[0598]
[0599] Under an Ar atmosphere, 1,3-dibromo-5-tert-butylbenzene (10.2 g), intermediate compound 1a (28.6 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) (2.1 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (Sphos) (1.6 g) and NaO t Bu (6.7 g) were placed in a 2000 mL three-necked flask, dissolved in toluene (350 mL), and the mixture was heated and refluxed for 2 hours. Then the temperature was restored to room temperature, water was added, the product was extracted with CH2Cl2, the organic layer was collected, dried over MgSO4, and the solvent was removed by evaporation under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 24.7 g of intermediate compound 2a (yield: 78%). The mass number of intermediate compound 2a measured by FAB-MS was 925.
[0600] Synthesis of intermediate compound 2b
[0601]
[0602] Intermediate compound 1b (32.5 g) was used instead of intermediate compound 1a, and intermediate compound 2b (29.4 g, yield 83%) was synthesized in substantially the same manner as intermediate compound 2a. The mass number of intermediate compound 2b measured by FAB-MS was 1036.
[0603] Synthesis of Intermediate Compound 2c
[0604]
[0605] Respectively use t Bu-C6H4-4-(C6H3-3,5-Br2) (12.3 g) and Intermediate Compound 1a (28.6 g) to replace 1,3-dibromo-5-tert-butylbenzene and Intermediate Compound 1a, and synthesize Intermediate Compound 2c (30.1 g, yield 88%) in substantially the same manner as Intermediate Compound 2a. The mass number of Intermediate Compound 2c measured by FAB-MS is 1001. t Bu-C6H4-4-(C6H3-3,5-Br2) was synthesized using the method described in the patent document (World Intellectual Property Organization, WO2013090185A1 2013-06-20), and the relevant part is incorporated herein by reference.
[0606] Synthesis of Intermediate Compound 2d
[0607]
[0608] Use 9-(3,5-dibromophenyl)-9H-carbazole (13.3 g) to replace 1,3-dibromo-5-tert-butylbenzene, and synthesize Intermediate Compound 2d (25.5 g, yield 72%) in substantially the same manner as Intermediate Compound 2a. The mass number of Intermediate Compound 2d measured by FAB-MS is 1033.
[0609] Synthesis of Intermediate Compound 2e
[0610]
[0611] Respectively use 3,5-dibromo-1,1'-biphenyl (10.3 g) and Intermediate Compound 1c (22.3 g) to replace 1,3-dibromo-5-tert-butylbenzene and Intermediate Compound 1a, and synthesize Intermediate Compound 2e (23.9 g, yield 91%) in substantially the same manner as Intermediate Compound 2a. The mass number of Intermediate Compound 2e measured by FAB-MS is 792.
[0612] (3) Synthesis of Intermediate Compounds 3a to 3g
[0613] Synthesis of Intermediate Compound 3a
[0614]
[0615] In an Ar atmosphere, intermediate compound 2a (22.6 g), I-C6H4-4- t Bu (86.3 g), CuI (14.1 g) and K2CO3 (20.3 g) were placed in a 1000 mL three-necked flask, and the mixture was heated and stirred at 190 °C for 96 hours. Then the temperature was restored to room temperature, water was added, the product was extracted with CH2Cl2, the organic layer was collected, dried over MgSO4, and the solvent was removed by evaporation under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 15.9 g of intermediate compound 3a (yield: 55%). The mass number of intermediate compound 3a measured by FAB-MS was 1189.
[0616] Synthesis of intermediate compound 3b
[0617]
[0618] Using intermediate compound 2c (24.5 g) instead of intermediate compound 2a, intermediate compound 3b (18.4 g, yield 59%) was synthesized in substantially the same manner as intermediate compound 3a. The mass number of intermediate compound 3b measured by FAB-MS was 1265.
[0619] Synthesis of intermediate compound 3c
[0620]
[0621] Using intermediate compound 2d (25.3 g) instead of intermediate compound 2a, intermediate compound 3c (20.1 g, yield 65%) was synthesized in substantially the same manner as intermediate compound 3a. The mass number of intermediate compound 3c measured by FAB-MS was 1298.
[0622] Synthesis of intermediate compound 3d
[0623]
[0624] Using 3-iodobenzofuran (86.3 g) instead of I-C6H4-4- t Bu, intermediate compound 3d (17.1 g, yield 56%) was synthesized in substantially the same manner as intermediate compound 3a. The mass number of intermediate compound 3d measured by FAB-MS was 1257.
[0625] Synthesis of intermediate compound 3e
[0626]
[0627] Intermediate compound 2b (25.4 g) and 1-chloro-3-iodobenzene (70.2 g) were used respectively instead of intermediate compound 2a and I-C6H4-4- t Bu, and intermediate compound 3e (17.9 g, yield 58%) was synthesized in substantially the same manner as intermediate compound 3a. The mass number of intermediate compound 3e measured by FAB-MS was 1265.
[0628] Synthesis of intermediate compound 3f
[0629]
[0630] 1-chloro-3-iodobenzene (70.2 g) was used instead of I-C6H4-4- t Bu, and intermediate compound 3f (16.8 g, yield 60%) was synthesized in substantially the same manner as intermediate compound 3a. The mass number of intermediate compound 3f measured by FAB-MS was 1144.
[0631] Synthesis of intermediate compound 3g
[0632]
[0633] Intermediate compound 2e (19.4 g) and 1-chloro-3-iodobenzene (70.2 g) were used respectively instead of intermediate compound 2a and I-C6H4-4- t Bu, and intermediate compound 3g (17.2 g, yield 69%) was synthesized in substantially the same manner as intermediate compound 3a. The mass number of intermediate compound 3g measured by FAB-MS was 1020.
[0634] (4) Synthesis of Example Compound 3, Example Compound 4, Example Compound 15, Example Compound 22 and Intermediate Compounds 28-1, 29-1, 54-1
[0635] Synthesis of Example Compound 3
[0636]
[0637] Under an Ar atmosphere, intermediate compound 3a (15.9 g) was placed in a 1000 mL three-necked flask and dissolved in o-dichlorobenzene (70 mL). The mixture was cooled to 0 °C in an ice bath, boron triiodide (15.7 g) was added thereto, and then the mixture was heated and stirred at 180 °C for 18 hours. Then the mixture was cooled to 0 °C in an ice bath, and triethylamine (100 mL) was added. The temperature was restored to room temperature, then water was added, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by evaporation under reduced pressure. The obtained crude product was purified by silica gel column chromatography (preparative HPLC (eluent: CHCl3)) and recrystallized from toluene to obtain 2.4 g of intermediate compound 3 (yield: 15%). The mass number of intermediate compound 3 measured by FAB-MS was 1197.
[0638] Synthesis of Example Compound 4
[0639]
[0640] Using intermediate compound 3b (16.9 g) instead of intermediate compound 3a, Example Compound 4 (3.6 g, yield 21%) was synthesized in substantially the same manner as Example Compound 3. The mass number of Example Compound 4 measured by FAB-MS was 1273.
[0641] Synthesis of Example Compound 15
[0642]
[0643] Using intermediate compound 3c (17.4 g) instead of intermediate compound 3a, Example Compound 15 (6.8 g, yield 39%) was synthesized in substantially the same manner as Example Compound 3. The mass number of Example Compound 15 measured by FAB-MS was 1307.
[0644] Synthesis of Example Compound 22
[0645]
[0646] Using intermediate compound 3d (16.8 g) instead of intermediate compound 3a, Example Compound 22 (2.4 g, yield 14%) was synthesized in substantially the same manner as Example Compound 3. The mass number of Example Compound 22 measured by FAB-MS was 1265.
[0647] Synthesis of Intermediate Compound 28-1
[0648]
[0649] Intermediate Compound 28-1 (4.5 g, yield 27%) was synthesized in substantially the same manner as Example Compound 3 using Intermediate Compound 3e (16.7 g) instead of Intermediate Compound 3a. The mass number of Intermediate Compound 28-1 measured by FAB-MS was 1,265.
[0650] Synthesis of intermediate compound 29-1
[0651]
[0652] Intermediate Compound 29-1 (4.1 g, yield 24%) was synthesized in substantially the same manner as Example Compound 3 using Intermediate Compound 3f (15.3 g) instead of Intermediate Compound 3a. The mass number of Intermediate Compound 29-1 measured by FAB-MS was 1178.
[0653] Synthesis of intermediate compound 54-1
[0654]
[0655] Intermediate Compound 54-1 (3.8 g, yield 28%) was synthesized in substantially the same manner as Example Compound 3 using Intermediate Compound 3g (13.6 g) instead of Intermediate Compound 3a. The mass number of Intermediate Compound 54-1 measured by FAB-MS was 1020.
[0656] (5) Synthesis of Example Compound 28, Example Compound 29 and Example Compound 54
[0657] Synthesis of Example Compound 28
[0658]
[0659] Under Ar atmosphere, intermediate compound 28-1 (4.5 g), carbazole (28.6 g), Pd(dba)2 (0.2 g), tri-tert-butylphosphine tetrafluoroborate ([P( t Bu)3H]BF4, 0.2g) and NaO t Bu (1.7g) is added in the three-necked flask of 500mL, is dissolved in toluene (20mL), and is heated and refluxed for 24 hours.After returning to room temperature, water is added, and CH is used Cl is extracted, organic layer is collected, and MgSO is used Dry, and remove solvent by evaporation under reduced pressure.The crude product obtained is purified by silica gel column chromatography to obtain 1.8g (yield 33%) of embodiment compound 28.The mass number of embodiment compound 28 measured by FAB-MS is 1527.
[0660] Synthesis of Example Compound 29
[0661]
[0662] The Example Compound 29 (2.3 g, yield 38%) was synthesized in substantially the same manner as Example Compound 28, using Intermediate Compound 29-1 (4.1 g) and 3,6-diphenylcarbazole (2.5 g) instead of Intermediate Compound 28-1 and carbazole, respectively. The mass number of Example Compound 29 measured by FAB-MS was 1719.
[0663] Synthesis of Example Compound 54
[0664]
[0665] The Example Compound 54 (4.5 g, yield 27%) was synthesized in substantially the same manner as Example Compound 28, using Intermediate Compound 54-1 (3.6 g) and 3,6-di-tert-butylcarbazole (2.2 g) instead of Intermediate Compound 28-1 and carbazole, respectively. The mass number of Example Compound 54 measured by FAB-MS was 1507.
[0666] 2. Fabrication and Evaluation of Light-Emitting Elements
[0667] A light-emitting element according to one or more embodiments was fabricated using the method described herein, the light-emitting element including a fused polycyclic compound according to one or more embodiments in the emission layer. The light-emitting elements according to Examples 1 to 7 were fabricated using, as dopant materials in the emission layer, the fused polycyclic compounds 3, 4, 15, 22, 28, 29, and 54, which are the fused polycyclic compounds of the example compounds described previously, respectively. The light-emitting elements according to Comparative Examples 1 to 9 correspond to the light-emitting elements fabricated using Comparative Example Compounds X1 to X9, respectively, as dopant materials in the emission layer.
[0668] Example Compounds
[0669]
[0670]
[0671] Comparative Example Compounds
[0672]
[0673]
[0674] Fabrication of Light-Emitting Elements
[0675] The first electrode with a thickness of 150 nm is formed using ITO. A hole injection layer with a thickness of 10 nm is formed on the first electrode using dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN). A hole transport layer with a thickness of 80 nm is formed on the hole injection layer using 2,2'-dimethyl-N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine (α-NPD). An emission auxiliary layer with a thickness of 5 nm is formed on the hole transport layer using 1,3-bis(N-carbazolyl)benzene (mCP). An emission layer with a thickness of 20 nm in which 3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl (mCBP) is doped with an example compound or a comparative example compound is formed on the emission auxiliary layer. An electron transport layer with a thickness of 30 nm is formed on the emission layer using 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi). An electron injection layer with a thickness of 0.5 nm is formed on the electron transport layer using LiF, and a second electrode with a thickness of 100 nm is formed on the electron injection layer using aluminum (Al). Each layer is formed by vapor deposition in a vacuum atmosphere.
[0676] Compounds for manufacturing light-emitting elements according to examples and comparative examples are disclosed herein. The materials used are appropriate materials, and commercial products are purified by sublimation for use in the manufacture of light-emitting elements.
[0677]
[0678] Evaluation of characteristics of light-emitting elements
[0679] The luminous efficiency and element lifetime of each of the light-emitting elements manufactured by using Example Compound 3, Example Compound 4, Example Compound 15, Example Compound 22, Example Compound 28, Example Compound 29, and Example Compound 54, and Comparative Example Compounds X-1 to X-9 described above were evaluated. The evaluation results of the light-emitting elements according to Examples 1 to 7 and Comparative Examples 1 to 9 are listed in Table 1. In Table 1, the relative external luminous efficiency (EQE 800尼特 ) and element lifetime (LT 50 ) of each of the manufactured light-emitting elements are shown. In Table 1, among the evaluation results of the characteristics of the light-emitting elements according to examples and comparative examples, the relative external luminous efficiency is the external quantum efficiency evaluated at 800 cd / m 2 (nit), and is a relative value with respect to the value of Comparative Example 1. Additionally, at 800 cd / m 2The luminance half-decay time in hours was evaluated at the initial luminance, and the value was listed as the element lifetime (LT 50 ).
[0680] Table 1
[0681]
[0682] Referring to the results in Table 1, it can be confirmed that, compared with the light-emitting elements according to the comparative examples, the light-emitting elements according to the examples (using a fused polycyclic compound according to one or more embodiments as the light-emitting material) each have improved luminous efficiency and element lifetime.
[0683] In an embodiment of the example compound, a nitrogen atom of a fused ring nucleus in which a boron atom is located at the center is connected to a first substituent, and thus the boron atom can be effectively protected. Therefore, high luminous efficiency and long element lifetime can be achieved.
[0684] Each of the example compounds includes a first substituent connected to a nitrogen atom of a fused ring nucleus in which a boron atom is located at the center. The first substituent includes a 2-biphenyl moiety and a second substituent connected to a second carbon of the 2-biphenyl moiety. The fused polycyclic compound represented by Formula 1 according to one or more embodiments includes a first substituent connected to a nitrogen atom of the fused ring nucleus, and the trigonal planar structure of the boron atom can be effectively maintained by the steric effect caused by the first substituent having a high spatial volume. Since the boron atom has an electron-deficient property due to the unoccupied p-orbital, if not properly protected, its structure can be changed to a tetrahedral structure by forming a bond with other nucleophiles, which can cause device degradation. According to the present disclosure, since the first substituent is introduced into the fused ring nucleus in the fused polycyclic compound represented by Formula 1 according to one or more embodiments, the unoccupied p-orbital of the boron atom can be effectively protected, and thus the degradation phenomenon caused by structural deformation can be prevented or reduced. In the example compounds, due to the structure with high steric hindrance, the intermolecular distance between adjacent molecules increases, which can suppress or reduce Dexter energy transfer. Therefore, the degradation of the element lifetime caused by an increase in the concentration of triplet excitons can be prevented or reduced. The light-emitting element according to one or more embodiments includes the fused polycyclic compound represented by Formula 1 according to one or more embodiments as a light-emitting dopant of a thermally activated delayed fluorescence (TADF) light-emitting element, and thus high luminous efficiency can be achieved in the blue light wavelength region, particularly in the deep blue light wavelength region.
[0685] Compared with the light-emitting element according to the embodiment, the light-emitting element according to Comparative Example 1 shows results of reduced element service life and light-emitting efficiency. The comparative compound X-1 contained in the light-emitting element according to Comparative Example 1 includes a condensed ring structure in which one boron atom and two nitrogen atoms are located at the center, but does not include the first substituent proposed in the present disclosure. Therefore, the effect of spatial protection of the boron atom within the plate-like structure of the condensed ring nucleus is reduced, and it is difficult to expect intermolecular interaction effects, etc. Therefore, when the comparative compound X-1 is applied to the light-emitting element, it can be confirmed that the light-emitting element has reduced light-emitting efficiency and element service life compared with the embodiment using the embodiment compound.
[0686] The comparative compound X-2 and the comparative compound X-4 contained in the light-emitting elements according to Comparative Example 2 and Comparative Example 4 respectively include structures similar to the first substituent of the compound used in the present disclosure. However, it can be seen that when these comparative compounds are applied to the respective light-emitting elements, the light-emitting elements may not have significantly improved light-emitting efficiency and element service life because the substituent substituted at the position of the second substituent (i.e., the Z position in Formula 1) is an alkyl group having a small steric volume.
[0687] In the comparative compound X-3 and the comparative compound X-9 contained in the light-emitting elements according to Comparative Example 3 and Comparative Example 9 respectively, an additional ring is formed in the molecular structure. On the other hand, the additional ring contains continuously arranged sp 3 hybridized carbon, and thus the quaternary carbon structure may deteriorate. Therefore, it can be confirmed that when these comparative compounds are applied to the light-emitting element, each of the light-emitting elements has relatively low light-emitting efficiency and element service life.
[0688] The comparative compound X-8 contained in the light-emitting element according to Comparative Example 8 includes a structure similar to the first substituent of the compound applied to the present disclosure. However, it can be confirmed that the substituent substituted at the position of the second substituent (i.e., the Z position in Formula 1) is a fluorine atom as a halogen atom and is an electrophilic substituent, which causes the emissive material to decompose by electron capture, and thus the element service life is significantly reduced.
[0689] The comparative compound X-5 and the comparative compound X-7 contained in the light-emitting elements according to Comparative Example 5 and Comparative Example 7 respectively include structures similar to the first substituent of the compound applied to the present disclosure. However, the comparative compound X-5 includes a phenyl substituent at a position other than the position of the second substituent (i.e., the Z position in Formula 1), and the comparative compound X-7 has phenyl substituents at both the Z position and the R5 position. It can be confirmed that when these comparative compounds are applied to the light-emitting element, the improvement in light-emitting efficiency and element service life is not significant compared with the embodiment compound.
[0690] The comparative compound X-6 contained in the light-emitting element of Comparative Example 6 includes a dibenzofuranyl group, which is bonded to the ortho position of the carbon atom connected to the N atom in the first substituent of the compound according to the present disclosure, and thus has a partially similar structure. However, compared with the compound of the example, due to the fused structure of the dibenzofuranyl group, the volume of the molecular structure is reduced. Therefore, it can be confirmed that when the comparative compound X-6 is applied to the light-emitting element, the luminous efficiency and the element service life are relatively lower than those of the compound of the example.
[0691] The light-emitting element according to one or more embodiments may exhibit improved element characteristics of high luminous efficiency and long element service life.
[0692] The fused polycyclic compound represented by Formula 1 according to one or more embodiments may be contained in the emission layer of the light-emitting element, and thus may contribute to improving the high luminous efficiency and long element service life of the light-emitting element.
[0693] By including the light-emitting element of the present disclosure, the display device according to one or more embodiments may exhibit excellent or appropriate display quality.
[0694] As used herein, the terms "substantially", "about" or similar terms are used as approximate terms rather than terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by a person of ordinary skill in the art. As used herein, "about" includes the recited value and means within an acceptable deviation of a particular value as determined by a person of ordinary skill in the art, taking into account the measurements being discussed and the errors associated with the measurement of a particular quantity (i.e., the limitations of the measurement system). For example, "about" may mean within one or more standard deviations of the recited value, or within ±30%, ±20%, ±10% or ±5% of the recited value.
[0695] In the context of the present application, and unless otherwise defined, the terms "use", "using" and "used" may be regarded as synonymous with the terms "utilize", "utilizing" and "utilized", respectively.
[0696] Any numerical range recited herein is intended to include all sub-ranges subsumed within the recited range having the same degree of numerical precision. For example, a range of "1.0 to 10.0" is intended to include all sub-ranges between and including the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited in this specification is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, the applicant reserves the right to amend this specification (including the claims) to expressly recite any sub-range subsumed within the ranges expressly recited herein.
[0697] In the present disclosure, when the particles (e.g., quantum dots) are spherical, "size" indicates the particle diameter or the average particle diameter, and when the particles are non-spherical, "size" indicates the major axis length or the average major axis length. The diameter (or size) of the particles can be measured using a scanning electron microscope or a particle size analyzer. As the particle size analyzer, for example, the HORIBA, LA-950 laser particle size analyzer can be used. When measuring the size of the particles using the particle size analyzer, the average particle diameter (or size) is referred to as D 50 . D 50 refers to the average diameter (or size) of the particles whose cumulative volume corresponds to 50 volume % in the particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50 % of the particles starting from the smallest particles in the distribution curve cumulated in the order of the smallest particle size to the largest particle size when the total number of the particles is 100 %.
[0698] The light-emitting element / device, display device, display apparatus, or any other related device / device or component according to an embodiment of the present disclosure described herein may be implemented using any suitable hardware, firmware (e.g., application specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the device may be formed on one integrated circuit (IC) chip or on separate IC chips. Further, the various components of the device may be implemented on a flexible printed circuit film, tape carrier package (TCP), or printed circuit board (PCB), or formed on a substrate. Further, the various components of the device may be processes or threads running on one or more processors in one or more computing devices, executing computer program instructions, and interacting with other system components to perform the various functions described herein. The computer program instructions are stored in a memory, which may be implemented in a computing device using a standard storage device, such as, for example, random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer-readable media, such as, for example, a CD-ROM or a flash drive, etc. And, those skilled in the art should recognize that, without departing from the scope of the embodiments of the present disclosure, the functions of various computing devices may be combined or integrated into a single computing device, or the functions of a dedicated computing device may be distributed over one or more other computing devices.
[0699] The description of the features or aspects in each embodiment should generally be considered applicable to other similar features or aspects in other embodiments.
[0700] So far, although one or more embodiments of the present disclosure have been described, it should be understood that the present disclosure should not be limited to these embodiments, but one or more appropriate changes and modifications may be made by those of ordinary skill in the art within the spirit and scope of the disclosure claimed below. Each appropriate feature of the various embodiments of the present disclosure may be partially or wholly combined or combined with each other, and may be interlocked and operated technically in various appropriate ways, and unless otherwise stated or implied, each embodiment may be implemented independently of each other or combined with each other in any suitable manner.
[0701] Therefore, the technical scope of the present disclosure is not intended to be limited to what is stated in the detailed description of the present disclosure, but is intended to be defined by the claims and their equivalents.
Claims
1. A fused polycyclic compound represented by Formula 1: Formula 1 In formula 1, X is direct connection, O, S, Se, CR 31 R 32 , PR 33 、SiR 34 R 35 , C=O, C=S or NR 36 , Z is a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R1 to R8, R a To R k and R 31 To R 36 each independently represents hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted boron, substituted or unsubstituted carbonyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and / or bonds with an adjacent group to form a ring, When selected from R1 to R8, R a To R k and R 31 To R 36 When any one of the groups is bonded to an adjacent group to form a ring, the formed ring does not include two consecutive sp 3 Hybridized carbon, and When Z is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, R5 is not a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
2. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by any one selected from Formula 2-1 to Formula 2-8: Formula 2-1 Formula 2-2 Formula 2-3 Formula 2-4 Formula 2-5 Formula 2-6 Formula 2-7 Formula 2-8 In Formula 2-1 to Formula 2-8, R9 to R 19 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, Y1 and Y2 are each independently O or S, n9 is an integer selected from 0 to 5, n14 to n18 are each independently an integer selected from 0 to 4, n19 is an integer selected from 0 to 3, and X, R1 to R8, R a To R k and R 31 To R 36 Same as defined in Formula 1.
3. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by Formula 3-1 or Formula 3-2: Formula 3-1 Formula 3-2 In formula 3-1 and formula 3-2, A1 is hydrogen, deuterium, a substituted or unsubstituted oxy group, or a substituted or unsubstituted amine group, A2 is hydrogen, deuterium, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted amine, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, R m is hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, m is an integer selected from 0 to 4, and X, Z, R2 to R8, R a To R k and R 31 To R 36 Same as defined in Formula 1.
4. The fused polycyclic compound according to claim 3, wherein In formula 3-2, Z and A2 are the same.
5. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by any one selected from Formula 4-1 to Formula 4-4: Formula 4-1 Formula 4-2 Formula 4-3 Formula 4-4 In Formula 4-1 to Formula 4-4, X1 to X5 are each independently O, S, CR 26 R 27 or NR 28 , R a1 To R k1 and R 20 To R 28 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted carbonyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and / or bonds with an adjacent group to form a ring, n20 and n23 to n25 are each independently an integer selected from 0 to 4, n21 and n22 are each independently an integer selected from 0 to 3, and X, Z, R1 to R8, and R 31 To R 36 Same as defined in Formula 1.
6. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by Formula 5: Formula 5 In formula 5, R x is hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted boron, substituted or unsubstituted carbonyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and / or bonds to an adjacent group to form a ring, nx is an integer selected from 0 to 5, and Z, R1 to R8 and R a To R k Same as defined in Formula 1.
7. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by Formula 6: Formula 6 In formula 6, Z1 and Z2 are each independently a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R 41 To R 48 each independently represents hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted boron, substituted or unsubstituted carbonyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and / or bonds with an adjacent group to form a ring, and R1 to R8 and R a To R k Same as defined in Formula 1.
8. The fused polycyclic compound according to claim 7, wherein In Formula 6, R1 and R 41 Each is independently hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted phenoxy or substituted or unsubstituted diphenylamino.
9. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by any one selected from Formula 7-1 to Formula 7-4: Formula 7-1 Formula 7-2 Formula 7-3 Formula 7-4 In equations 7-1 to 7-4, A is hydrogen or deuterium, R x1 , R x2 , R y1 and R y2 each independently represents deuterium, halogen, substituted or unsubstituted amine, substituted or unsubstituted carbonyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, R x3 , R x4 , R y3 and R y4 Each is independently deuterium, halogen, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted amine, substituted or unsubstituted carbonyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and / or bonds to an adjacent group to form a ring, and X, Z, R1 to R8, R a To R c and R 31 To R 36 Same as defined in Formula 1.
10. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is represented by Formula 8-1 or Formula 8-2: Formula 8-1 Formula 8-2 In equation 8-1 and equation 8-2, A is hydrogen or deuterium, R z is deuterium, halogen, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted amine, substituted or unsubstituted carbonyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring carbon atoms, and X, Z, R1 to R8, R d To R k and R 31 To R 36 Same as defined in Formula 1.
11. The fused polycyclic compound according to claim 1, wherein the fused polycyclic compound represented by Formula 1 is any one of the compounds selected from Compound Group 1: Compound Group 1 12. A light emitting element, comprising: a first electrode; a second electrode facing the first electrode; as well as an emitting layer between the first electrode and the second electrode, wherein the emission layer comprises the condensed polycyclic compound according to any one of claims 1 to 11 as a first compound.
13. The light-emitting element according to claim 11, wherein the emission layer further comprises at least one selected from the group consisting of a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula D-1: Formula HT-1 In formula HT-1, M1 to M8 are each independently N or CR 51 , L1 is a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, Y a For direct connection, CR 52 R 53 or SiR 54 R 55 , Ar a is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and R 51 To R 55 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thiol, substituted or unsubstituted oxy, substituted or unsubstituted amine, substituted or unsubstituted boron, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 60 ring carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 60 ring carbon atoms, and / or combines with an adjacent group to form a ring; Formula ET-1 In formula ET-1, Selected from Z a To Z c At least one of them is N, and the rest are CR 56 , R 56 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, b1 to b3 are each independently an integer selected from 0 to 10, Ar b To Ar d are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and L2 to L4 are each independently a directly linked, substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms; and Formula D-1 In formula D-1, Q1 to Q4 are each independently C or N, C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring group of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group of 2 to 30 ring carbon atoms, L 11 To L 13 Each is independently a direct connection, *-O-*, *-S-*, a substituted or unsubstituted alkylene group of 1 to 20 carbon atoms, a substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms, in which L 11 To L 13 In the table, "——*" refers to the part connected to C1 to C4. b11 to b13 are each independently 0 or 1, R 61 To R 66 Each of the following is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thiol, substituted or unsubstituted oxy, substituted or unsubstituted amine, substituted or unsubstituted boron, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 60 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 60 ring carbon atoms, selected from R 61 To R 66 One or more of may independently bond with an adjacent group to form a ring, and d1 to d4 are each independently an integer selected from 0 to 4.
14. A display device, comprising: basal layer; a circuit layer on the base layer; as well as A display device layer is on the circuit layer and includes the light emitting element according to claim 12 or 13.
15. The display device according to claim 14, wherein the display device further comprises a light control layer on the display device layer and comprising quantum dots, The light emitting element is configured to emit light of a first color, and The light control layer comprises: a first light control component including first quantum dots that convert the first color light into a second color light at a wavelength longer than the wavelength of the first color light; a second light control component including a second quantum dot that converts the first color light into a third color light at a wavelength longer than the wavelengths of the first color light and the second color light; as well as A third light control component is configured to transmit the first color light.