Light-emitting element, fused polycyclic compound for light-emitting element, and display device including light-emitting element
By using specific fused polycyclic compounds in the emitting layer of the organic electroluminescent device, the problems of high driving voltage, low emission efficiency and short life in the prior art are solved, and a high-efficiency and long-life luminescence effect is achieved.
Patent Information
- Application Number
- CN202411159273.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-08-24
- Filing Date
- 2024-08-22
- Publication Date
- 2025-02-28
AI Technical Summary
The existing organic electroluminescent devices have shortcomings in driving voltage, emission efficiency and life, making it difficult to achieve stable and efficient display.
An emission layer composed of a specific fused polycyclic compound is adopted, which improves emission efficiency and extends the lifetime of the component through the fused structure of boron atoms, nitrogen atoms and aromatic rings.
The emission efficiency and life of the light emitting element are significantly improved and the display quality is improved.
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Abstract
Description
[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0110961 filed in the Korean Intellectual Property Office on August 24, 2023, the entire contents of which are incorporated herein by reference. Technical Field
[0002] One or more embodiments of the present disclosure herein relate to a light emitting element, a fused polycyclic compound used in the light emitting element, and a display device including the light emitting element. Background Art
[0003] Recently, the development of organic electroluminescent devices as image display devices is actively underway. The organic electroluminescent device is different from the liquid crystal display device and is a self-luminescent device in which holes and electrons injected from the first electrode and the second electrode are respectively recombined in the emission layer of the organic electroluminescent device, so that the light-emitting material including the organic compound in the emission layer emits light to realize display (e.g., display of an image).
[0004] In applying organic electroluminescent devices to display apparatuses, it is desired or required to reduce driving voltage and increase emission efficiency and lifetime of the organic electroluminescent devices, and thus development of materials for organic electroluminescent devices that stably achieve these requirements is constantly desired or pursued.
[0005] For example, recently, in order to realize an organic electroluminescent device with relatively high emission efficiency, technology of phosphorescent emission utilizing the energy of a triplet state or fluorescent emission utilizing a phenomenon in which singlet excitons are generated by collision of triplet excitons (triplet-triplet annihilation, TTA) is being developed, and development of thermally activated delayed fluorescence (TADF) materials utilizing the delayed fluorescence phenomenon is being actively pursued. Summary of the invention
[0006] One or more aspects of the embodiments of the present disclosure relate to a light emitting element having improved emission efficiency and element lifetime.
[0007] One or more aspects of the embodiments of the present disclosure relate to a fused polycyclic compound that can improve the emission efficiency and element life of a light emitting element.
[0008] One or more aspects of an embodiment of the present disclosure are directed to a display device having excellent or suitable display quality by including a light emitting element having improved emission efficiency and lifetime.
[0009] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments.
[0010] According to one or more embodiments of the present disclosure, a light emitting element includes a first electrode, a second electrode on the first electrode, and an emission layer between the first electrode and the second electrode, wherein the emission layer includes a first compound represented by Formula 1.
[0011] Formula 1
[0012]
[0013] In Formula 1, X can be O or S, Ar 1 and Ar 2 may be independently 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 1 , R 2 and R a To R k Each may independently be hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring-forming carbon atoms, and may optionally combine with an adjacent group to form (or provide) a ring, n1 may be an integer from 0 to 2, and n2 may be an integer from 0 to 4.
[0014] In one or more embodiments, the first compound represented by Formula 1 may be represented by Formula 2.
[0015] Formula 2
[0016]
[0017] In formula 2, R 3 It can be hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring-forming carbon atoms, and can optionally combine with adjacent groups to form (or provide) a ring, and n3 can be an integer from 0 to 5.
[0018] In formula 2, for X, Ar 1 , R 1 , R 2 , R a To R k , n1 and n2, the same content defined in formula 1 can be applied.
[0019] In one or more embodiments, the first compound represented by Formula 1 may be represented by Formula 3-1 or Formula 3-2.
[0020] Formula 3-1
[0021]
[0022] Formula 3-2
[0023]
[0024] In Formula 3-1 and Formula 3-2, R 4 To R 6 Each may independently be hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted sulfenyl, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring-forming carbon atoms, n4 may be an integer from 0 to 5, n5 may be an integer from 0 to 3, and n6 may be an integer from 0 to 4.
[0025] In formula 3-1 and formula 3-2, for X, Ar 1 , R 1 , R 2 , R a To R k , n1 and n2, the same content defined in formula 1 can be applied.
[0026] In one or more embodiments, the first compound represented by Formula 1 may be represented by Formula 4.
[0027] Formula 4
[0028]
[0029] In formula 4, R 7 It can be hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted sulfenyl, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring-forming carbon atoms, and can optionally combine with adjacent groups to form (or provide) a ring, and n7 can be an integer from 0 to 5.
[0030] In formula 4, for X, Ar 2 , R 1 , R 2 , R aTo R k , n1 and n2, the same content defined in formula 1 can be applied.
[0031] In one or more embodiments, the first compound represented by Formula 1 may be represented by Formula 5-1 or Formula 5-2.
[0032] Formula 5-1
[0033]
[0034] Formula 5-2
[0035]
[0036] In Formula 5-1 and Formula 5-2, Y can be O or S, R 8 To R 12 may be independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms, R 13 It can be hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring-forming carbon atoms, and can optionally combine with adjacent groups to form (or provide) a ring, n8 can be an integer from 0 to 3, n12 can be an integer from 0 to 4, n9, n10 and n13 can each independently be an integer from 0 to 5, and n11 can be an integer from 0 to 2.
[0037] In Formula 5-1 and Formula 5-2, for X, Ar 2 , R 1 , R 2 , R a To R k , n1 and n2, the same content defined in formula 1 can be applied.
[0038] In one or more embodiments, the first compound represented by Formula 1 may be represented by one selected from Formula 6-1 to Formula 6-4.
[0039] Formula 6-1
[0040]
[0041] Formula 6-2
[0042]
[0043] Formula 6-3
[0044]
[0045] Formula 6-4
[0046]
[0047] In equations 6-1 to 6-4, R x1 , R x2 , R y1 and R y2 may be independently deuterium, halogen, substituted or unsubstituted amine, substituted or unsubstituted silyl, 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 and R x4 Each may independently be deuterium, a halogen, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, 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, and may optionally combine with an adjacent group to form (or provide) a ring.
[0048] In Formula 6-1 to Formula 6-4, for X, Ar 1 ,Ar 2 , R 1 , R 2 , R a To R c , n1 and n2, the same content defined in formula 1 can be applied.
[0049] In one or more embodiments, in Formula 6-1 to Formula 6-4, R x1 , R x2 , R y1 and R y2 Each of them may independently be a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted N-carbazolyl group or a substituted or unsubstituted acridinyl group.
[0050] In one or more embodiments, the first compound represented by Formula 1 may be represented by Formula 7.
[0051] Formula 7
[0052]
[0053] In formula 7, R z It may be deuterium, halogen, substituted or unsubstituted amine, 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.
[0054] In formula 7, for X, Ar 1 ,Ar 2 , R 1 , R 2 , R d To R k , n1 and n2, the same content defined in formula 1 can be applied.
[0055] In one or more embodiments, in Formula 7, R z It may be 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 dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted xanthyl group, or a substituted or unsubstituted indolocarbazolyl group.
[0056] In one or more embodiments, the first compound represented by Formula 1 may be represented by Formula 8.
[0057] Formula 8
[0058]
[0059] In formula 8, for X, Ar 1 ,Ar 2 , R 1 , R 2 , R a To R k and n2, the same content defined in equation 1 can be applied.
[0060] In one or more embodiments, the emission layer may further include 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.
[0061] Formula HT-1
[0062]
[0063] In formula HT-1, M 1 To M 8 can be independently N or CR 51 , L 1It can 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, Y a Can be direct key, CR 52 R 53 or SiR 54 R 55 ,Ar a may be 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 of them may independently be 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-forming carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 60 ring-forming carbon atoms, and may optionally combine with adjacent groups to form (or provide) a ring.
[0064] Formula ET-1
[0065]
[0066] In formula ET-1, Z is selected from a To Z c At least one of them is N, and the rest can be CR 56 , R 56 may be hydrogen, deuterium, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring carbon atoms, b1 to b3 may each independently be an integer of 0 to 10, Ar b To Ar d and L may each independently be 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 L 2 To L 4 Each of them may 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.
[0067] Formula D-1
[0068]
[0069] In formula D-1, Q 1To Q 4 may be independently C or N, C1 to C4 may be independently substituted or unsubstituted hydrocarbon rings of 5 to 30 ring carbon atoms or substituted or unsubstituted heterocyclic rings of 2 to 30 ring carbon atoms, L 11 To L 13 Can be directly connected, *-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, b1 to b3 may all independently be 0 or 1, R 61 To R 66 D1 to D4 may each independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted sulfenyl, 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-forming carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 60 ring-forming carbon atoms, and D1 to D4 may each independently be an integer from 0 to 4.
[0070] A display device according to one or more embodiments of the present disclosure includes a substrate layer, a circuit layer on the substrate 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 on the first electrode, and an emission layer between the first electrode and the second electrode and including a first compound represented by Formula 1.
[0071] In one or more embodiments, the light emitting element may further include a capping layer on the second electrode. The capping layer may have a refractive index of about 1.6 or more with respect to light in a wavelength range of about 550 nm to about 660 nm.
[0072] In one or more embodiments, the display device may further include a light control layer, which is on the display device layer and includes quantum dots. The light emitting element may emit a first color light, and the light control layer may include a first light control unit, a second light control unit, and a third light control unit, the first light control unit including a first quantum dot that converts the first color light into a second color light in a wavelength region longer than the wavelength region of the first color light, the second light control unit including a second quantum dot that converts the first color light into a third color light in a wavelength region longer than the wavelength region of the first color light and the wavelength region of the second color light, and the third light control unit transmits the first color light.
[0073] In one or more embodiments, the display device may further include a color filter layer on the light control layer. The color filter layer may include a first filter configured to transmit the second color light, a second filter configured to transmit the third color light, and a third filter configured to transmit the first color light.
[0074] According to one or more embodiments of the present disclosure, the fused polycyclic compound may be represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS
[0075] The accompanying drawings are included to provide a further understanding of the present disclosure, and the accompanying drawings are incorporated into and constitute a part of the present disclosure. The accompanying 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 understood from the following description of the embodiments in conjunction with the accompanying drawings. In the accompanying drawings:
[0076] Figure 1 is a plan view of a display device according to one or more embodiments of the present disclosure;
[0077] Figure 2 is a cross-sectional view of a display device according to one or more embodiments of the present disclosure;
[0078] Figure 3 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0079] Figure 4 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0080] Figure 5 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0081] Figure 6 is a cross-sectional view schematically showing a light emitting element according to one or more embodiments of the present disclosure;
[0082] Figure 7 and Figure 8 are cross-sectional views of display devices according to one or more embodiments of the present disclosure;
[0083] Fig. 9 is a cross-sectional view showing a display device according to one or more embodiments of the present disclosure;
[0084] Fig.10 is a cross-sectional view showing a display device according to one or more embodiments of the present disclosure; and
[0085] Fig.11is a diagram showing a vehicle in which a display device according to one or more embodiments is arranged. DETAILED DESCRIPTION
[0086] The present disclosure can be modified in one or more suitable ways and has many forms, and therefore specific / exemplary 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 particular forms disclosed, but is intended to cover all modifications, equivalents and substitutes falling within the spirit and scope of the present disclosure.
[0087] When explaining each in the accompanying drawings, the same reference numerals are used to refer to the same elements. In the accompanying drawings, for the sake of clarity of the present disclosure, the size of each structure can be exaggeratedly shown. It will be understood that, although the terms "first" and / or "second" etc. can be used 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 component. For example, without departing from the scope of the exemplary embodiments of the present disclosure, the first component can be named as the second component, and similarly, the second component can be named as the first component. As used herein, unless the context clearly indicates otherwise, the singular forms "one", "one (kind / person)" and "the (said)" are intended to also include plural forms. In addition, when describing an embodiment of the present disclosure, the use of "can" refers to "one or more embodiments of the present disclosure".
[0088] In the present disclosure, it will be understood that the terms "including and variations thereof", "comprising and variations thereof" and / or "having and variations thereof" and the like indicate the presence of the features, quantities, steps, operations, components, parts (components) or combinations thereof disclosed in the disclosure, but do not exclude the possibility of the presence or addition of one or more other features, quantities, steps, operations, components, parts (components) or 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. Expressions such as "at least one (of) ...", "one (of) ..." and "selected from ..." modify the entire column of elements when they are after / before a column of elements, without modifying the individual elements of the column. 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 represent only a, only b, only c, (e.g., simultaneously) both a and b, (e.g., simultaneously) both a and c, (e.g., simultaneously) both b and c, all of a, b and c, or variations thereof. Depending on the circumstances, the " / " used herein may be interpreted as "and" or "or".
[0089] In the present disclosure, if a layer, film, region or plate is referred to as being "on" another layer, film, region or plate or "in the upper part of" another layer, film, region or plate, it may not only be "directly on" the layer, film, region or plate, but one or more intervening layers, films, regions or plates may also be present (for example, when a layer, film, region or plate is referred to as being "on" another layer, film, region or plate or "in the upper part of" another layer, film, region or plate, it may not only be "directly on" the layer, film, region or plate, but one or more intervening layers, films, regions or plates may also be present). In contrast, if a layer, film, region or plate is referred to as being "below" another layer, film, region or plate, or "in the lower portion of" another layer, film, region or plate, it may not only be directly below the layer, film, region or plate, but one or more intervening layers, films, regions or plates may also be present (for example, when a layer, film, region or plate is referred to as being "below" another layer, film, region or plate, or "in the lower portion of" another layer, film, region or plate, it may not only be directly below the layer, film, region or plate, but one or more intervening layers, films, regions or plates may also be present). In one or more embodiments, it will be understood that if a part (component) is referred to as being "on" another part (component), it may be arranged above the other part (component), or it may also be arranged below the other part (component) (for example, when a part (component) is referred to as being "on" another part (component), it may be arranged above the other part (component), or it may also be arranged below the other part (component)). In one or more embodiments, "directly on..." may mean that there are no additional layers, films, regions, plates, etc. between a layer, film, region, plate, etc. and another part (component). For example, "directly on..." may mean that two layers or two members are disposed without using an additional member (such as an adhesive member) therebetween.
[0090] In the present disclosure, the term "substituted or unsubstituted" may refer to being unsubstituted or substituted with (e.g., selected from) at least one substituent in the group consisting of deuterium, halogen, cyano, nitro, amino (amine), silyl, oxy, sulfenyl, sulfinyl, sulfonyl, carbonyl, boryl, phosphine oxide, phosphine sulfide, alkyl, alkenyl, alkynyl, hydrocarbon ring, aryl and heterocyclic groups. In one or more embodiments, each of the substituents exemplified above may be substituted or unsubstituted. For example, biphenyl may be interpreted as an aryl or phenyl substituted with a phenyl.
[0091] In the present disclosure, the phrase "bonds to an adjacent group to form (or provide) a ring" may refer to a group bonding to an adjacent group to form (or provide) a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The hydrocarbon ring may include an aliphatic hydrocarbon ring and / or an aromatic hydrocarbon ring. The heterocycle may include an aliphatic heterocycle and / or an aromatic heterocycle. The hydrocarbon ring and the heterocycle may both be monocyclic or polycyclic. In one or more embodiments, the ring formed by the adjacent groups bonded to each other may be connected to another ring to form (or provide) a spiro structure.
[0092] In the present disclosure, the term "adjacent group" may refer to a substituent that replaces an atom directly connected to an atom substituted with a corresponding substituent, another substituent that replaces an atom substituted with a corresponding substituent, or a substituent that is spatially positioned closest 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.
[0093] In the present disclosure, examples of halogen may include fluorine, chlorine, bromine, or iodine.
[0094] In the present disclosure, the alkyl group may be linear or branched. The carbon number in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 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-butyloctyl, 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-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heonicosyl, 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.
[0095] In the present disclosure, cycloalkyl may refer to a cyclic alkyl. The number of carbons in the cycloalkyl may be 3 to 50, 3 to 30, 3 to 20, or 3 to 10. Examples of cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl, and / or bicycloheptyl, but embodiments of the present disclosure are not limited thereto.
[0096] In the present disclosure, alkenyl 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 linear or branched. The number of carbon atoms in the alkenyl group is not particularly limited, for example, it may be 2 to 30, 2 to 20 or 2 to 10. Examples of alkenyl groups may include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl and / or styrylvinyl, etc., but embodiments of the present disclosure are not limited thereto.
[0097] In the present disclosure, alkynyl 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 2 or more carbon atoms. The alkynyl group may be straight chain or branched. Although the number of carbon atoms is not particularly limited, it may be 2 to 30, 2 to 20, or 2 to 10. Examples of alkynyl groups may include ethynyl and / or propynyl, etc., but embodiments of the present disclosure are not limited thereto.
[0098] In the present disclosure, the 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.
[0099] In the present disclosure, aryl 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 carbon atoms in the aryl group may be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, and / or Base, etc., but the embodiments of the present disclosure are not limited thereto.
[0100] In the present disclosure, the fluorenyl group may be substituted, and two substituents may be combined with each other to form (or provide) a spiro structure. Examples of substituted fluorenyl groups are as follows. However, embodiments of the present disclosure are not limited thereto.
[0101]
[0102] The heterocyclic group used herein 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 may include an aliphatic heterocyclic group and / or an aromatic heterocyclic group. The aromatic heterocyclic group may be a heteroaryl. The aliphatic heterocyclic ring and the aromatic heterocyclic ring may both be monocyclic or polycyclic.
[0103] In the present disclosure, the heterocyclic group may contain at least one of B, O, N, P, Si, Se and S as a heteroatom. If the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other (for example, 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 carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10.
[0104] In the present disclosure, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si, Se, and S as a heteroatom. The number of ring 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 an oxirane group, an oxirane group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, a thianyl group, a tetrahydropyranyl group, and / or a 1,4-dioxanyl group, but the embodiments of the present disclosure are not limited thereto.
[0105] In the present disclosure, the heteroaryl group may contain at least one of B, O, N, P, Si, Se and S as a heteroatom. If the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other (for example, when the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other). The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20 or 2 to 10. Examples of heteroaryl groups may include thienyl, furanyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiphenyl, benzofuranyl, phenanthroline, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzothiole, dibenzofuranyl, xanthene and / or indolocarbazolyl, etc., but the embodiments of the present disclosure are not limited thereto.
[0106] In the disclosure, the above description of the aryl group can be applied to the arylene group except that the arylene group is a divalent group. The above description of the heteroaryl group can be applied to the heteroarylene group except that the heteroarylene group is a divalent group.
[0107] In the present disclosure, the silyl group may include an alkylsilyl group and / or an arylsilyl group. Examples of the silyl group may include a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group and / or a phenylsilyl group, etc., but the embodiments of the present disclosure are not limited thereto.
[0108] In the present disclosure, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have the following structure, but embodiments of the present disclosure are not limited thereto.
[0109]
[0110] In the present disclosure, the number of carbon atoms in the sulfinyl group or the sulfonyl group is not particularly limited, and for example, may be 1 to 30. The sulfinyl group may include an alkylsulfinyl group and / or an arylsulfinyl group. The sulfonyl group may include an alkylsulfonyl group and / or an arylsulfonyl group.
[0111] In the present disclosure, the 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. Examples of the thio group may include a methylthio group, an ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, an octylthio group, a dodecylthio group, a cyclopentylthio group, a cyclohexylthio group, a phenylthio group, and a naphthylthio group, but the embodiments of the present disclosure are not limited thereto.
[0112] In the present disclosure, an oxy group may refer to an oxygen atom bonded to an alkyl or aryl group defined above. The oxy group may include an alkoxy group and / or an aryloxy group. The alkoxy group may be a straight chain, a branched chain, or a ring. 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. Examples of oxy groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, and / or benzyloxy, etc., but embodiments of the present disclosure are not limited thereto.
[0113] The boryl group used herein may refer to a boron atom bonded to an alkyl or aryl group defined above. Boryl groups may include alkyl boryl groups and / or aryl boryl groups. Examples of boryl groups may include dimethyl boryl groups, methyl boryl groups, tert-butyl methyl boryl groups, diphenyl boryl groups and / or phenyl boryl groups, but embodiments of the present disclosure are not limited thereto.
[0114] In the present disclosure, the number of carbon atoms in the amine group is not particularly limited, for example, it can be 1 to 30. The amine group can include an alkylamine group and / or an arylamine group. Examples of the amine group can include a methylamine group, a dimethylamine group, an aniline group, a diphenylamine group, a naphthylamine group and / or a 9-methyl-anthrylamine group, but the embodiments of the present disclosure are not limited thereto.
[0115] In the present disclosure, the alkyl group among the alkoxy group, the alkylthio group, the alkylsulfinyl group, the alkylsulfonyl group, the alkylaryl group, the alkylamino group, the alkylboryl group, the alkylsilyl group, and the alkylamine group may be the same as exemplified above.
[0116] In the present disclosure, the aryl group among the aryloxy group, the arylthio group, the arylsulfinyl group, the arylsulfonyl group, the arylamino group, the arylboryl group, the arylsilyl group, and the arylamine group may be the same as exemplified above.
[0117] In the present disclosure, a direct bond may refer to a single bond.
[0118] In this disclosure, and "-*" indicate where to link.
[0119] 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".
[0120] Figure 1 is a plan view showing a display device DD according to one or more embodiments of the present disclosure. Figure 2 is a cross-sectional view of a display device DD according to one or more embodiments. Figure 2 It is shown along Figure 1 A cross-sectional view of a portion of the display device DD taken along line II'.
[0121] The display device DD may include a display panel DP and an optical layer PP arranged on the display panel DP on a third direction axis DR3. 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 arranged on the display panel DP to control light reflected in the display panel DP due to external light. The optical layer PP may include, for example, a polarizing 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.
[0122] The base substrate BL may be disposed on the optical layer PP. The base substrate BL may be a member that provides 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.
[0123] The display device DD according to one or more embodiments may further include a filling layer. The filling layer may be arranged 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 siloxane resin, and an epoxy resin.
[0124] The display panel DP may include a base layer BS, a circuit layer DP-CL disposed 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 portions of the pixel defining film PDL, and an encapsulation layer TFE disposed on the light emitting devices ED-1, ED-2, and ED-3.
[0125] The base layer BS may be a member that provides a base surface on which the display device layer DP-ED is arranged. The base layer BS 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 layer BS may be an inorganic layer, an organic layer, or a composite material layer.
[0126] In one or more embodiments, the circuit layer DP-CL may be arranged on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors. Each of the transistors may include a control electrode, an input electrode, and an output electrode. For example, in some embodiments, the circuit layer DP-CL may include a switching transistor and a driving transistor for driving the light emitting devices ED-1, ED-2, and ED-3 of the display device layer DP-ED.
[0127] Each of the light emitting devices ED-1, ED-2, and ED-3 may have a configuration according to the configuration to be described later. Figures 3 to 6 The structure of one of the light emitting elements (devices) ED of the embodiment. Each of the light emitting devices ED-1, ED-2 and ED-3 may include a first electrode EL1, a hole transport region HTR, a corresponding emission layer EML-R, EML-G or EML-B, an electron transport region ETR and a second electrode EL2.
[0128] Figure 2 An embodiment is shown in which the corresponding emission layers EML-R, EML-G and EML-B of the light-emitting devices ED-1, ED-2 and ED-3 are arranged in the opening OH defined in the pixel defining film PDL, and the hole transport region HTR, the electron transport region ETR and the second electrode EL2 are set 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 to this. 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 in the pixel defining film PDL. For example, in some embodiments, the hole transport region HTR, the corresponding 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 in an inkjet printing method.
[0129] The encapsulation layer TFE may cover the light emitting devices ED-1, ED-2 and ED-3. The encapsulation layer TFE may seal the light emitting devices ED-1, ED-2 and ED-3. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be formed by stacking one or more layers. The encapsulation layer TFE may include at least one insulating layer. In some embodiments, the encapsulation layer TFE may include at least one inorganic film (hereinafter, encapsulation-inorganic film). In some embodiments, the encapsulation layer TFE may include at least one organic film (hereinafter, encapsulation-organic film) and at least one encapsulation-inorganic film.
[0130] The encapsulation-inorganic film protects the light-emitting devices ED-1, ED-2, and ED-3 from moisture / oxygen, and the encapsulation-organic film protects the light-emitting devices ED-1, ED-2, and ED-3 from foreign matter such as dust particles. The encapsulation-inorganic film may 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 may include an acrylic compound and / or an epoxy compound, etc. In some embodiments, the encapsulation-organic film may include a photopolymerizable organic material, but the embodiments of the present disclosure are not particularly limited thereto.
[0131] The encapsulation layer TFE may be disposed on the second electrode EL2 , and may be disposed to fill the opening OH.
[0132] Reference Figure 1 and Figure 2 , the display device DD may 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 may be areas in which light generated by the corresponding light emitting devices ED-1, ED-2, and ED-3 is emitted. The light emitting areas PXA-R, PXA-G, and PXA-B may be spaced and / or separated from each other on a plane (e.g., in a plan view).
[0133] Each of the light-emitting regions PXA-R, PXA-G, and PXA-B may be a region divided by a pixel-defining film PDL. The non-light-emitting region NPXA may be a region corresponding to the pixel-defining film PDL between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B. In one or more embodiments, the light-emitting regions PXA-R, PXA-G, and PXA-B may correspond to pixels, respectively. The pixel-defining film PDL may divide the light-emitting devices ED-1, ED-2, and ED-3. The corresponding emission layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3 may be arranged in the opening OH defined in the pixel-defining film PDL and separated from each other.
[0134] The light emitting regions PXA-R, PXA-G, and PXA-B may be divided into a plurality of groups according to the colors of the lights generated from the light emitting devices ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In the display device DD of one or more embodiments shown in , three light emitting regions PXA-R, PXA-G, and PXA-B that emit red light, green light, and blue light, respectively, are exemplarily shown. For example, in one or more embodiments, the display device DD 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.
[0135] In the display device DD according to one or more embodiments, a 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 some 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 some embodiments, a red light emitting region PXA-R, a green light emitting region PXA-G, and a 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.
[0136] 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 in substantially the same wavelength range, or at least one light emitting device may emit light beams in a wavelength range different from the wavelength range of the 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.
[0137] 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. Figure 1 , a plurality of red light emitting regions PXA-R may be arranged along the second direction axis DR2, a plurality of green light emitting regions PXA-G may be arranged along the second direction axis DR2, and a plurality of blue light emitting regions PXA-B may be arranged along the second direction axis DR2. In one or more embodiments, the red light emitting regions PXA-R, the green light emitting regions PXA-G, and the blue light emitting regions PXA-B may be alternately arranged in this order along the first direction axis DR1.
[0138] Figure 1 and Figure 2It is shown that all the light emitting regions PXA-R, PXA-G, and PXA-B have similar areas, but the embodiments of the present disclosure are not limited thereto. Therefore, the light emitting regions PXA-R, PXA-G, and PXA-B may have different areas from each other according to the wavelength range of the emitted light. The areas of the light emitting regions PXA-R, PXA-G, and PXA-B may refer to an area when viewed on a plane defined by the first direction axis DR1 and the second direction axis DR2 (e.g., an area in a plan view).
[0139] In one or more embodiments, the arrangement of the light emitting regions PXA-R, PXA-G, and PXA-B is not limited to Figure 1 , and according to the characteristics of the display quality desired or required in the display device DD, the sequence in which the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B are arranged can be provided in one or more suitable combinations. For example, in one or more embodiments, the arrangement form of the light emitting areas PXA-R, PXA-G, and PXA-B can be pentile Arrangement form (for example, RGBG matrix, RGBG structure or RGBG matrix structure) or diamond (Diamond Pixel TM ) arrangement form (for example, a display (for example, an OLED display) comprising red, blue, and green (RGB) light-emitting areas arranged in a diamond shape). is an officially registered trademark of Samsung Display Co., Ltd. Diamond Pixel TM is a trademark of Samsung Display Co., Ltd.
[0140] 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 some 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.
[0141] In the following, Figures 3 to 6 Each is a cross-sectional view schematically showing a light emitting element ED according to one or more embodiments of the present disclosure. 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 stated order.
[0142] and Figure 3 compared to, Figure 4A cross-sectional view of a light emitting element ED according to one or more embodiments is shown, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 3 compared to, Figure 5 A cross-sectional view of a light emitting element ED according to one or more embodiments is shown, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 4 compared to, Figure 6 A cross-sectional view of a light emitting element ED including one or more embodiments of a cap layer CPL disposed on the second electrode EL2 is shown.
[0143] The first electrode EL1 has conductivity (for example, is a conductor). The first electrode EL1 may be formed of a metal material, a metal alloy and / or a conductive compound. The first electrode EL1 may 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 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode or a reflective electrode. The first electrode EL1 may include at least one of the following substances (for example, at least one selected from the following substances): 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), zinc (Zn), compounds of two or more thereof, mixtures of two or more thereof and oxides thereof.
[0144] If 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 the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, any compound thereof, any 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 transflective 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 first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the embodiments of the present disclosure are not limited thereto. In one or more embodiments, 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 1000 Å. to about For example, in one or more embodiments, the thickness of the first electrode EL1 may be about 1000 Å. to about
[0145] The hole transport region HTR may be disposed 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 auxiliary layer, and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 100 Å. to about
[0146] The hole transport region HTR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multi-layered structure including a plurality of layers formed of a plurality of different materials.
[0147] 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 hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / buffer layer, hole injection layer HIL / buffer layer, hole transport layer HTL / buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked in sequence (e.g., in the stated order) from the first electrode EL1, but the embodiments of the present disclosure are not limited thereto.
[0148] The hole transport region HTR may be formed using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and / or laser induced thermal imaging (LITI).
[0149] In one or more embodiments, the hole transport region HTR may include a compound represented by Formula H-1:
[0150] Formula H-1
[0151]
[0152] In formula H-1, L 1 and L 2 L and L 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. a and b may each independently be an integer from 0 to 10. In one or more embodiments, if a or b is an integer of 2 or more, then the plurality of L 1 or more L 2 L and L 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 (for example, when a or b is an integer of 2 or more, multiple L 1 or more L 2 and (ii) 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).
[0153] In formula H-1, Ar 1 and Ar 2and Ar may be independently substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms or substituted or unsubstituted heteroaryl groups having 2 to 30 ring carbon atoms. 3 It may be 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.
[0154] In one or more embodiments, the compound represented by formula H-1 may be a monoamine compound. In one or more embodiments, the compound represented by formula H-1 may be a compound selected from Ar 1 To Ar 3 In one or more embodiments, the compound represented by formula H-1 may be a diamine compound in which Ar 1 and Ar 2 A carbazole compound comprising a substituted or unsubstituted carbazole group in at least one of the following: 1 and Ar 2 A fluorene compound in which at least one of the compounds includes a substituted or unsubstituted fluorenyl group.
[0155] The compound represented by Formula H-1 may be any one selected from the compounds in Compound Group H. However, the compounds listed in Compound Group H are merely examples, and the compound represented by Formula H-1 is not limited to the compounds represented in Compound Group H:
[0156] Compound Group H
[0157]
[0158]
[0159] In some embodiments, the hole transport region HTR may include a phthalocyanine compound (such as copper phthalocyanine), N 1 ,N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4-dimethylphenylbenzene-1,4-diamine) (DNTPD), 4,4',4"-[tri(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tri(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tri[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(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate] and dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN), etc.
[0160] In one or more embodiments, the hole transport region HTR may include at least one selected from 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) or 4,4',4"-tri(N-carbazyl)triphenylamine (TCTA)), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylene-bis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD) and 1,3-bis(carbazole-9-yl)benzene (mCP), etc.
[0161] In one or more embodiments, the hole transport region HTR may include at least one selected from 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-carbazole-9-yl)benzene (mDCP), etc.
[0162] The hole transport region HTR may include one or more of the above-mentioned 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.
[0163] 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 When the hole transport region HTR includes the hole transport layer HTL, the hole transport layer HTL may have a thickness of about to about For example, if the hole transport region HTR includes an electron blocking layer EBL, the electron blocking layer EBL may have a thickness of about to about (For example, when the hole transport region HTR includes the electron blocking layer EBL, the electron blocking layer EBL may have a thickness of about to about If 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 properties may be achieved without significantly increasing the driving voltage.
[0164] In one or more embodiments, in addition to the above-mentioned materials, the hole transport region HTR may further include a charge generating material to increase conductivity. The charge generating material may be uniformly (substantially uniformly) or non-uniformly (substantially non-uniformly) dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may include at least one of a halogenated metal compound, a quinone derivative, a metal oxide, and a cyano compound, but the embodiments of the present disclosure are not limited thereto. For example, in some embodiments, the p-dopant may include a halogenated metal compound (such as CuI and / or RbI), a quinone derivative (such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F 4 -TCNQ)), metal oxides (such as tungsten oxide and / or molybdenum oxide) and / or cyano-containing compounds (such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN) and / or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9)), etc., but the embodiments of the present disclosure are not limited thereto.
[0165] 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 the light emission efficiency may thus be increased. The material that may be included in the hole transport region HTR may be used as the material included in the buffer layer. The electron blocking layer EBL is a layer for preventing or reducing electron injection from the electron transport region ETR to the hole transport region HTR.
[0166] In one or more embodiments, the emission layer EML may be disposed on the hole transport region HTR. The emission layer EML may have, for example, about to about or about to about The emission layer EML may have a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multilayer structure having a plurality of layers formed using a plurality of different materials.
[0167] The light-emitting element ED of one or more embodiments may include a fused polycyclic compound represented by Formula 1 in at least one functional layer arranged between the first electrode EL1 and the second electrode EL2. In the light-emitting element ED of one or more embodiments, the emission layer EML may include the fused polycyclic compound of one or more embodiments. In one or more embodiments, the emission layer EML may include the fused polycyclic compound of one or more embodiments as a dopant. The fused polycyclic compound of one or more embodiments may be a dopant material of the emission layer EML. In the present disclosure, the fused polycyclic compound of one or more embodiments may be referred to as a first compound.
[0168] The fused polycyclic compound of one or more embodiments may include a fused structure of multiple aromatic rings via a boron atom and a nitrogen atom. The fused polycyclic compound of one or more embodiments may include a fused structure of multiple aromatic rings via a boron atom and two nitrogen atoms. The fused polycyclic compound of one or more embodiments may include a fused structure of multiple aromatic rings via a boron atom, a first nitrogen atom, and a second nitrogen atom. For example, the fused polycyclic compound of one or more embodiments may include a fused ring formed by fusing multiple aromatic rings via a boron atom, a first nitrogen atom, and a second nitrogen atom.
[0169] The fused polycyclic compound of one or more embodiments may include a fused structure of the first aromatic ring to the third aromatic ring (i.e., the first aromatic ring, the second aromatic ring, and the third aromatic ring) via a boron atom, a first nitrogen atom, and a second nitrogen atom. The first aromatic ring, the second aromatic ring, and the third aromatic ring may be connected to the boron atom, and the first aromatic ring and the third aromatic ring may be further connected to each other via the first nitrogen atom, and the second aromatic ring and the third aromatic ring may be further connected to each other via the second nitrogen atom. In the present disclosure, the boron atom, the first nitrogen atom, the second nitrogen atom, and the fused structure formed by fusing the first aromatic ring to the third aromatic ring via a boron atom, a first nitrogen atom, and a second nitrogen atom may be referred to as a "fused ring core".
[0170] In one or more embodiments, the first to third aromatic rings may be independently substituted or unsubstituted monocyclic aromatic hydrocarbon rings of 6 to 30 ring-forming carbon atoms. In one or more embodiments, the first to third aromatic rings may be independently 6-membered aromatic hydrocarbon rings. For example, in one or more embodiments, the first to third aromatic rings may be independently be benzene rings.
[0171] The fused polycyclic compound of one or more embodiments may include a first substituent connected to the first nitrogen atom. The first substituent may include a dibenzoheteroatom portion comprising an oxygen atom or a sulfur atom. For example, in one or more embodiments, the first substituent may include a dibenzofuran portion or a dibenzothiophene portion. The first substituent is connected to the first nitrogen atom at the carbon at position 1, and includes a structure in which the carbon at position 2 is substituted by a second substituent such as an aryl or heteroaryl group. In the present disclosure, the structure and carbon number of the first substituent may be the same as shown in Formula S.
[0172] Formula S
[0173]
[0174] In formula S, X is O or S.
[0175] The first substituent can be directly bonded to the first nitrogen atom of the fused ring core without a linker (eg, without a separate linker).
[0176] The fused polycyclic compound of one or more embodiments may be represented by Formula 1.
[0177] Formula 1
[0178]
[0179] The fused polycyclic compound of one or more embodiments represented by Formula 1 may include a fused structure of three aromatic rings via a boron atom, a first nitrogen atom, and a second nitrogen atom.d To R g The benzene ring at which the substituent represented by may correspond to the first aromatic ring, represented by R h To R k The benzene ring at which the substituent represented by may correspond to the above-mentioned second aromatic ring, and R a To R c The benzene ring at which the substituent represented by may correspond to the third aromatic ring described above. In Formula 1, the fused heteroaryl moiety of three rings connected to the nitrogen atom and including X may correspond to the first substituent described above. In Formula 1, Ar 2 may correspond to the above-mentioned second substituent.
[0180] In Formula 1, X may be O or S.
[0181] In formula 1, Ar 1 and Ar 2 and Ar may be independently substituted or unsubstituted aryl groups of 6 to 30 ring carbon atoms or substituted or unsubstituted heteroaryl groups of 2 to 30 ring carbon atoms. 1 and Ar 2 Each of them may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted dibenzofuranyl group.
[0182] In formula 1, R 1 , R 2 and R a To R k can be independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted sulfenyl, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms. In one or more embodiments, R is selected from 1 , R 2 and R a To R k One or more of them may optionally combine with adjacent groups to form (or provide) a ring. For example, in one or more embodiments, R 1 , R 2 and R a To R kand R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R e and R f May optionally combine with each other to form (or provide) an additional hydrocarbon ring or heterocyclic ring.
[0183] In Formula 1, n1 may be an integer from 0 to 2. In Formula 1, if n1 is 0, the fused polycyclic compound of one or more embodiments may not be R 1 Where n1 is 2 and all R 1 The embodiment where all R are hydrogen can be the same as the embodiment where n1 is 0. If n1 is 2, then multiple R 1 Can be all the same, or selected from multiple R 1 At least one of them may be different.
[0184] In Formula 1, n2 may be an integer from 0 to 4. In Formula 1, if n2 is 0, the fused polycyclic compound of one or more embodiments may not be R 2 Where n2 is 4 and all R 2 The embodiment where all R are hydrogen can be the same as the embodiment where n2 is 0. If n2 is an integer of 2 or greater, then the plurality of R 2 Can be all the same, or selected from multiple R 2 At least one of them may be different.
[0185] In one or more embodiments, in Formula 1, R d To R k They may each independently be hydrogen, deuterium, or one substituent selected from the substituents represented by Formulae a-1 to a-22.
[0186] Formula a-1
[0187]
[0188] Formula a-2
[0189]
[0190] Formula a-3
[0191]
[0192] Formula a-4
[0193]
[0194] Formula a-5
[0195]
[0196] Formula a-6
[0197]
[0198] Formula a-7
[0199]
[0200] Formula a-8
[0201]
[0202] Formula a-9
[0203]
[0204] Formula a-10
[0205]
[0206] Formula a-11
[0207]
[0208] Formula a-12
[0209]
[0210] Formula a-13
[0211]
[0212] Formula a-14
[0213]
[0214] Formula a-15
[0215]
[0216] Formula a-16
[0217]
[0218] Formula a-17
[0219]
[0220] Formula a-18
[0221]
[0222] Formula a-19
[0223]
[0224] Formula a-20
[0225]
[0226] Formula a-21
[0227]
[0228] Formula a-22
[0229]
[0230] In Formula a-1 to Formula a-22, "*-" is a position to which the condensed ring core of the condensed polycyclic compound represented by Formula 1 is connected.
[0231] In one or more embodiments, in Formula 1, R a To R c They may each independently be hydrogen, deuterium, an unsubstituted tert-butyl group, or one substituent selected from the substituents represented by Formulae b-1 to b-17.
[0232] Formula b-1
[0233]
[0234] Formula b-2
[0235]
[0236] Formula b-3
[0237]
[0238] Formula b-4
[0239]
[0240] Formula b-5
[0241]
[0242] Formula b-6
[0243]
[0244] Formula b-7
[0245]
[0246] Formula b-8
[0247]
[0248] Formula b-9
[0249]
[0250] Formula b-10
[0251]
[0252] Formula b-11
[0253]
[0254] Formula b-12
[0255]
[0256] Formula b-13
[0257]
[0258] Formula b-14
[0259]
[0260] Formula b-15
[0261]
[0262] Formula b-16
[0263]
[0264] Formula B-17
[0265]
[0266] In Formula b-1 to Formula b-17, "*-" is a position to which the condensed ring core of the condensed polycyclic compound represented by Formula 1 is connected.
[0267] The fused polycyclic compound of one or more embodiments represented by Formula 1 has a structure in which a first substituent is linked to a fused ring core, and can achieve high emission efficiency and long life (or referred to as "element life" or "service life").
[0268] The fused polycyclic compound of one or more embodiments includes a "fused ring core" of five rings formed by fusing the first aromatic ring to the third aromatic ring (i.e., the first aromatic ring, the second aromatic ring, and the third aromatic ring) via a boron atom, a first nitrogen atom, and a second nitrogen atom. In addition, the fused polycyclic compound of one or more embodiments includes a first substituent connected to the first nitrogen atom of the fused ring core. The fused polycyclic compound represented by Formula 1 according to one or more embodiments includes a first substituent, and high emission efficiency and increased lifetime can be achieved.
[0269] The first substituent may include a dibenzofuran moiety or a dibenzothiophene moiety. The first substituent is connected to the first nitrogen atom at the carbon at the position 1 of the dibenzofuran moiety or the dibenzothiophene moiety represented by formula S. At the carbon at the position 2 of the first substituent, a second substituent as an aryl or heteroaryl group is substituted. The fused polycyclic compound of one or more embodiments includes a first substituent connected to the first nitrogen atom, and the triangular planar structure of the boron atom can be effectively maintained by the steric hindrance effect caused by the first substituent with a high spatial volume. The boron atom has an electron-deficient property due to the empty p orbital, and can form a bond with other nucleophiles to be converted into a tetrahedral structure. This may become a factor that degrades the light-emitting element ED. According to the present disclosure, in the fused polycyclic compound of one or more embodiments, because the first substituent is introduced into the fused ring core, the empty p orbital of the boron atom can be effectively protected, and the degradation phenomenon caused by structural deformation can be prevented or reduced.
[0270] In one or more embodiments, in the fused polycyclic compound of one or more embodiments, the intermolecular interaction can be suppressed or reduced by the steric hindrance effect of the first substituent, and the aggregation and the formation of quasi-molecules or exciplexes can be controlled or reduced, so that the emission efficiency can be increased. Because the fused polycyclic compound of one or more embodiments represented by Formula 1 has a bulky structure, the intermolecular distance can be increased, and the Dexter energy transfer can be reduced. Therefore, the increase in the concentration of triplet excitons in the fused polycyclic compound can be suppressed or reduced. The high concentration of triplet excitons is maintained in an excited state for a long time to induce the decomposition of the compound and induce the generation of hot excitons with high energy generated by triplet-triplet annihilation (TTA), thereby inducing the destruction of the structure around the compound (e.g., around the compound). In addition, triplet-triplet annihilation is a bimolecular reaction, and the triplet excitons used to emit light are quickly burned (e.g., annihilated), which may induce the degradation of the emission efficiency by non-radiative transitions. The fused polycyclic compound of one or more embodiments has an increased intermolecular distance due to the first substituent, and can suppress or reduce Dexter energy transfer, thereby suppressing or reducing the degradation of life due to the increase in triplet concentration. Therefore, if the fused polycyclic compound of one or more embodiments is applied to the emission layer EML of the light-emitting element ED, the emission efficiency can be increased and the element life can be improved.
[0271] In addition, in the fused polycyclic compound of one or more embodiments, the first substituent is connected to the first nitrogen atom at the carbon at the position 1 where the electron density of the first substituent is the lowest, so the highest occupied molecular orbital (HOMO) energy level of the molecule is even further reduced due to the electron-withdrawing effect, a deep HOMO can be achieved, the difference between the HOMO energy level of the host and the HOMO energy level of the fused polycyclic compound can be reduced, and the increase in the concentration of triplet excitons caused by hole capture and subsequent exciton recombination can be prevented or reduced. Therefore, the emission efficiency and life of the light-emitting element ED can be improved.
[0272] The fused polycyclic compound of one or more embodiments includes a first substituent, and a higher excited triplet energy level (Tn energy level, wherein n is 2 or greater) adjacent to the lowest excited singlet energy level (S1 energy level) may be relatively low. In one or more embodiments, in the fused polycyclic compound of one or more embodiments represented by Formula 1, the difference (ΔE) between the lowest excited singlet energy level (S1 energy level) and the higher excited triplet energy level (Tn energy level, wherein n is 2 or greater) adjacent to the lowest excited singlet energy level (S1 energy level) is S1Tn) may be about 0.6 eV or less. In some embodiments, in the fused polycyclic compound of one or more embodiments represented by Formula 1, the difference (ΔE) between the lowest excited singlet energy level (S1 energy level) and the 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) is about 0.6 eV or less. S1Tn ) may be about 0.2 eV or less. For example, in the fused polycyclic compound of one or more embodiments including the first substituent, the difference between the lowest excited singlet energy level and the second excited triplet energy level (T2 level) may be about 0.2 eV or less.
[0273] The compound exhibiting the property of thermally activated delayed fluorescence shows the intersystem crossing (ICS) of the exciton from the lowest singlet energy level to the triplet energy level, then shows the reverse intersystem crossing (RISC) of the exciton from the triplet energy level to the lowest singlet energy level, and finally emits delayed fluorescence by transitioning from the singlet energy level to the ground state. Here, the mechanism of thermally activated delayed fluorescence can include the transition of the higher triplet energy level (Tn energy level) and the lowest triplet energy level (T1 energy level) during the intersystem crossing (ICS) and reverse intersystem crossing (RISC). Because the fused polycyclic compound of one or more embodiments includes a first substituent, the higher excited triplet energy level (Tn energy level) adjacent to the lowest excited singlet energy level (S1 energy level) can be low, so the spin flip can be increased. In the present disclosure, spin flipping may refer to a transition phenomenon of an exciton from a higher excited triplet energy level (Tn energy level) to the lowest excited singlet energy level (S1 energy level) through 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). Therefore, the fused polycyclic compound of one or more embodiments exhibits a relatively low energy level characteristic of a higher excited triplet energy level (Tn energy level) adjacent to the lowest excited singlet energy level (S1 energy level), the rate of reverse intersystem crossing (RISC) via the higher excited triplet energy level (Tn energy level) to the lowest singlet energy level (S1 energy level) can be increased, the delayed fluorescence lifetime (Tau, τ) can be reduced, and the emission efficiency and lifetime characteristics can be improved.
[0274] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 2.
[0275] Formula 2
[0276]
[0277] In formula 2, R 3It can be hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms. In one or more embodiments, R 3 Can optionally combine with adjacent groups to form (or provide) a ring. For example, in some embodiments, R 3 It may be hydrogen, deuterium, substituted or unsubstituted tert-butyl or substituted or unsubstituted phenyl. In one or more embodiments, two adjacent R 3 An oxy group and a phenyl group may be included separately, and may optionally be combined with each other to form (or provide) a dibenzofuran moiety.
[0278] In Formula 2, n3 may be an integer from 0 to 5. In Formula 2, if n3 is 0, the fused polycyclic compound of one or more embodiments may not be R 3 In Formula 2, where n3 is 5 and all R 3 The embodiment in which all R are hydrogen can be the same as the embodiment in which n3 is 0. In Formula 2, if n3 is an integer of 2 or greater, then the plurality of R 3 Can be all the same or selected from multiple R 3 At least one of them may be different.
[0279] In formula 2, for X, Ar 1 , R 1 , R 2 , R a To R k , n1 and n2, the same contents explained in Formula 1 can be applied.
[0280] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by one selected from Formula 3-1 and Formula 3-2.
[0281] Formula 3-1
[0282]
[0283] Formula 3-2
[0284]
[0285] In Formula 3-1 and Formula 3-2, R 4 To R 6and R and R are independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted sulfenyl, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms. In one or more embodiments, R 4 To R 6 Each of may not combine with an adjacent group to form (or provide) a ring. For example, in some embodiments, R 4 To R 6 Each of may independently be hydrogen, deuterium, substituted or unsubstituted tert-butyl, or substituted or unsubstituted phenyl.
[0286] In Formula 3-1, n4 may be an integer from 0 to 5. If n4 is 0, the fused polycyclic compound of one or more embodiments may not be R 4 Where n4 is 5 and all R 4 The embodiment where all R are hydrogen can be the same as the embodiment where n4 is 0. If n4 is an integer of 2 or greater, then the plurality of R 4 Can be all the same or selected from multiple R 4 At least one of them may be different.
[0287] In Formula 3-2, n5 may be an integer from 0 to 3. If n5 is 0, the fused polycyclic compound of one or more embodiments may not be R 5 Where n5 is 3 and all R 5 The embodiment in which all R are hydrogen can be the same as the embodiment in which n5 is 0. If n5 is an integer of 2 or greater, then the plurality of R 5 Can be all the same or selected from multiple R 5 At least one of them may be different.
[0288] In Formula 3-2, n6 may be an integer from 0 to 4. If n6 is 0, the fused polycyclic compound of one or more embodiments may not be R 6 Where n6 is 4 and all R 6 The embodiment in which all R are hydrogen can be the same as the embodiment in which n6 is 0. If n6 is an integer of 2 or greater, then the plurality of R 6 Can be all the same or selected from multiple R 6 At least one of them may be different.
[0289] In formula 3-1 and formula 3-2, for X, Ar 1 , R 1 , R 2 , R a To Rk , n1 and n2, the same contents explained in Formula 1 can be applied.
[0290] In one or more embodiments, the fused polycyclic compound represented by Formula 3-2 may be represented by one selected from Formula 3-2-1 and Formula 3-2-2.
[0291] Formula 3-2-1
[0292]
[0293] Formula 3-2-2
[0294]
[0295] In formula 3-2-1 and formula 3-2-2, for X, Ar 1 , R 1 , R 2 , R a To R k , n1 and n2, the same as explained in Equation 1 can be applied. 5 , R 6 , n5 and n6, the same contents explained in formula 3-2 can be applied.
[0296] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 4.
[0297] Formula 4
[0298]
[0299] In formula 4, R 7 It may be hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted sulfenyl, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms. In one or more embodiments, multiple R may be provided. 7 , and the adjacent R 7 Can optionally combine with each other to form (or provide) a ring. For example, in some embodiments, R 7 It may be hydrogen, deuterium, halogen, substituted or unsubstituted oxy, substituted or unsubstituted methyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl or substituted or unsubstituted dibenzofuranyl. In one or more embodiments, two adjacent R 7An oxy group and a phenyl group may be included separately, and may optionally be combined with each other to form (or provide) a ring, thereby forming (or providing) a dibenzofuran moiety.
[0300] In Formula 4, n7 may be an integer from 0 to 5. In Formula 4, if n7 is 0, the fused polycyclic compound of one or more embodiments may not be R 7 In Formula 4, where n7 is 5 and all R 7 The embodiment in which all R are hydrogen can be the same as the embodiment in which n7 is 0. In Formula 4, if n7 is an integer of 2 or greater, then the plurality of R 7 Can be all the same or selected from multiple R 7 At least one of them may be different.
[0301] In formula 4, for X, Ar 2 , R 1 , R 2 , R a To R k , n1 and n2, the same contents explained in Formula 1 can be applied.
[0302] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 5-1 or Formula 5-2.
[0303] Formula 5-1
[0304]
[0305] Formula 5-2
[0306]
[0307] In Formula 5-2, Y may be O or S.
[0308] In Formula 5-1 and Formula 5-2, R 8 To R 12 and R and R are independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted sulfenyl, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms. In one or more embodiments, R 8 To R 12 Each of may not combine with an adjacent group to form (or provide) a ring. For example, in some embodiments, R 8 To R 12 Each of may be hydrogen, deuterium, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.
[0309] In one or more embodiments, in Formula 5-2, R 13 It may be hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted sulfenyl, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms. In one or more embodiments, multiple R may be provided. 13 , and the adjacent R 13 Can optionally combine with each other to form (or provide) a ring. For example, in some embodiments, R 13 It may be hydrogen, deuterium, halogen, substituted or unsubstituted oxy, substituted or unsubstituted methyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl or substituted or unsubstituted dibenzofuranyl. In one or more embodiments, two adjacent R 13 An oxy group and a phenyl group may be included separately, and may optionally be combined with each other to form (or provide) a ring, thereby forming (or providing) a dibenzofuran moiety.
[0310] In Formula 5-1 and Formula 5-2, n8 may be an integer from 0 to 3, n12 may be an integer from 0 to 4, n9, n10 and n13 may each independently be an integer from 0 to 5. n11 is an integer from 0 to 2.
[0311] If n8 is 0, the fused polycyclic compound of one or more embodiments may not be R 8 Where n8 is 3 and all R 8 The embodiment where all R are hydrogen can be the same as the embodiment where n8 is 0. If n8 is an integer of 2 or greater, then the plurality of R 8 Can be all the same or selected from multiple R 8 At least one of them may be different.
[0312] If n9 is 0, the fused polycyclic compound of one or more embodiments may not be R 9 Where n9 is 5 and all R 9 The embodiment in which all R are hydrogen can be the same as the embodiment in which n9 is 0. If n9 is an integer of 2 or greater, then the plurality of R 9 Can be all the same or selected from multiple R 9 At least one of them may be different.
[0313] If n10 is 0, the fused polycyclic compound of one or more embodiments may not be R 10 Where n10 is 5 and all R 10The embodiment in which all R are hydrogen can be the same as the embodiment in which n10 is 0. If n10 is an integer of 2 or greater, then the plurality of R 10 Can be all the same or selected from multiple R 10 At least one of them may be different.
[0314] If n11 is 0, the fused polycyclic compound of one or more embodiments may not be R 11 Where n11 is 2 and all R 11 The embodiment in which both R and R are hydrogen may be the same as the embodiment in which n11 is 0. If n11 is an integer of 2, then both R 11 Can be all the same or selected from two R 11 At least one of them may be different.
[0315] If n12 is 0, the fused polycyclic compound of one or more embodiments may not be R 12 Where n12 is 4 and all R 12 The embodiment in which all R are hydrogen can be the same as the embodiment in which n12 is 0. If n12 is an integer of 2 or greater, then the plurality of R 12 Can be all the same or selected from multiple R 12 At least one of them may be different.
[0316] If n13 is 0, the fused polycyclic compound of one or more embodiments may not be R 13 Where n13 is 5 and all R 13 The embodiment in which all R are hydrogen can be the same as the embodiment in which n13 is 0. If n13 is an integer of 2 or greater, then the plurality of R 13 Can be all the same or selected from multiple R 13 At least one of them may be different.
[0317] In Formula 5-1 and Formula 5-2, for X, Ar 2 , R 1 , R 2 , R a To R k , n1 and n2, the same contents explained with reference to Formula 1 can be applied.
[0318] In one or more embodiments, the fused polycyclic compound of one or more embodiments may have an axially symmetrical structure centered on the boron atom of the fused ring core and the third aromatic ring. In one or more embodiments, the fused polycyclic compound may be represented by Formula 5-2, X and Y may be the same, and Ar 2 Can have with it by R 13 The substituted phenyl portion has the same structure.
[0319] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by one selected from Formula 6-1 to Formula 6-4.
[0320] Formula 6-1
[0321]
[0322] Formula 6-2
[0323]
[0324] Formula 6-3
[0325]
[0326] Formula 6-4
[0327]
[0328] In equations 6-1 to 6-4, R x1 , R x2 , R y1 and R y2 and R are independently deuterium, halogen, substituted or unsubstituted amine, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms. For example, in one or more embodiments, R x1 , R x2 , R y1 and R y2 may be independently a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted N-carbazolyl group, or a substituted or unsubstituted acridinyl group. In one or more embodiments, the N-carbazolyl group may refer to a substituent group connected to the fused ring core of the fused polycyclic compound via the nitrogen atom of the N-carbazolyl group. In one or more embodiments, R x1 , R x2 , R y1 and R y2 Each may be independently one selected from the substituents represented by Formula a-1 to Formula a-22.
[0329] In formula 6-4, R x3 and R x4and R are independently deuterium, halogen, substituted or unsubstituted amine, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms. x3 and / or R x4 Each of the adjacent groups may independently optionally combine with an adjacent group to form (or provide) a ring. For example, in some embodiments, adjacently arranged R x3 and R x4 May optionally combine with each other to form (or provide) an additional hydrocarbon ring or heterocyclic ring.
[0330] In Formula 6-1 to Formula 6-4, for X, Ar 1 ,Ar 2 , R 1 , R 2 , R a To R c , n1 and n2, the same contents explained in Formula 1 can be applied.
[0331] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 7.
[0332] Formula 7
[0333]
[0334] In formula 7, R z It may be deuterium, halogen, substituted or unsubstituted amine, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms. In one or more embodiments, R z It is possible not to combine with adjacent groups to form (or provide) a ring. For example, in some embodiments, R z It may be 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 dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted xanthyl group, or a substituted or unsubstituted indolocarbazolyl group. In one or more embodiments, R z It may be an unsubstituted tert-butyl group or one selected from the substituents represented by Formula b-1 to Formula b-17.
[0335] In formula 7, for X, Ar 1 ,Ar 2 , R 1 , R 2 , Rd To R k , n1 and n2, the same contents explained in Formula 1 can be applied.
[0336] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 8.
[0337] Formula 8
[0338]
[0339] In formula 8, for X, Ar 1 ,Ar 2 , R 1 , R 2 , R a To R k and n2, the same as explained in Equation 1 can be applied.
[0340] In one or more embodiments, the fused polycyclic compound of one or more embodiments represented by Formula 1 may include at least one deuterium as a substituent. The fused polycyclic compound of one or more embodiments represented by Formula 1 may include a structure in which at least one hydrogen is substituted with deuterium.
[0341] The condensed polycyclic compound of one or more embodiments may be one selected from the compounds represented in compound group 1. At least one functional layer included in the light-emitting element ED of one or more embodiments may include at least one condensed polycyclic compound selected from the compounds represented in compound group 1. The light-emitting element ED of one or more embodiments may include at least one condensed polycyclic compound selected from the compounds represented in compound group 1 in the emission layer EML.
[0342] Compound Group 1
[0343]
[0344]
[0345]
[0346]
[0347]
[0348]
[0349]
[0350]
[0351]
[0352]
[0353]
[0354]
[0355]
[0356]
[0357]
[0358]
[0359]
[0360]
[0361]
[0362]
[0363]
[0364]
[0365]
[0366] In the exemplary compounds set forth in Compound Group 1, "D" refers to deuterium.
[0367] The emission spectrum of the fused polycyclic compound of one or more embodiments represented by Formula 1 has a half-maximum full width of about 10nm to about 50nm, or about 20nm to about 40nm. Because the emission spectrum of the first dopant (e.g., the first compound) of one or more embodiments represented by Formula 1 has the above-mentioned half-maximum full width range, if applied to the light-emitting element ED, the emission efficiency can be improved. In one or more embodiments, if the fused polycyclic compound of one or more embodiments is used as a material for a blue light-emitting element, the element life can be improved.
[0368] In one or more embodiments, the fused polycyclic compound of one or more embodiments represented by Formula 1 may be a material for emitting thermally activated delayed fluorescence. In one or more embodiments, the fused polycyclic compound of one or more embodiments represented by Formula 1 may be a thermally activated delayed fluorescence dopant having a difference (ΔE) between the lowest triplet excitation energy level (T1 energy level) and the lowest singlet excitation energy level (S1 energy level) of about 0.6 eV or less. ST In one or more embodiments, the fused polycyclic compound of one or more embodiments represented by Formula 1 may be a thermally activated delayed fluorescent dopant having a difference (ΔE) between the lowest triplet excitation energy level (T1 energy level) and the lowest singlet excitation energy level (S1 energy level) of about 0.2 eV or less. ST ). However, the embodiments of the present disclosure are not limited thereto.
[0369] In one or more embodiments, the fused polycyclic compound of one or more embodiments represented by Formula 1 may include a first substituent and a second substituent in the compound. By controlling the number and position of substitution of the first substituent and the second substituent, the singlet energy level and triplet energy level of the entire compound may be appropriately controlled or selected. Thus, the fused polycyclic compound of one or more embodiments of the present disclosure may exhibit improved thermally activated delayed fluorescence properties.
[0370] The fused polycyclic compound of one or more embodiments represented by Formula 1 may be a luminescent material having a luminescent center wavelength in a wavelength region of about 430 nm to about 490 nm. For example, the fused polycyclic compound of one or more embodiments represented by Formula 1 may be a blue thermally activated delayed fluorescence (TADF) dopant. However, the embodiments of the present disclosure are not limited thereto, and if the fused polycyclic compound of one or more embodiments is used as a luminescent material, the first dopant / compound may be used as a dopant material (such as a red-emitting dopant and a green-emitting dopant) that emits light in one or more suitable wavelength regions.
[0371] In the light emitting element ED of 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).
[0372] In one or more embodiments, the emission layer EML of the light emitting element ED may emit blue light. For example, in some embodiments, the emission layer EML of the light emitting element ED may emit blue light in a 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.
[0373] In one or more embodiments, the fused polycyclic compound of one or more embodiments may be included in the emission layer EML. In one or more embodiments, the fused polycyclic compound of one or more embodiments may be included in the emission layer EML as a dopant material. In some embodiments, the fused polycyclic compound of one or more embodiments may be a thermally activated delayed fluorescence emission material. The fused polycyclic compound of one or more embodiments may be used as a thermally activated delayed fluorescence dopant. For example, in the light-emitting element ED of one or more embodiments, the emission layer EML may include at least one selected from the fused polycyclic compounds represented in compound group 1 as a thermally activated delayed fluorescence dopant. However, the use of the fused polycyclic compound of one or more embodiments is not limited thereto.
[0374] In one or more embodiments, the emission layer EML may include a plurality of compounds. The emission layer EML of one or more embodiments may include a fused polycyclic compound (ie, a first compound) represented by Formula 1, a second compound additionally represented by Formula HT-1, a third compound represented by Formula ET-1, and the emission layer EML may further include a fourth compound represented by Formula D-1.
[0375] In one or more embodiments, the emission layer EML may include a first compound represented by Formula 1, and in some embodiments, may include at least one of a first compound represented by Formula 1, 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.
[0376] In one or more embodiments, the second compound may be used as a hole transport host material of the emission layer EML.
[0377] Formula HT-1
[0378]
[0379] In formula HT-1, M 1 To M 8 can be independently N or CR 51 For example, in one or more embodiments, all M 1 To M 8 Can be CR 51 In one or more embodiments, selected from M 1 To M 8 Any one of them can be N, and the rest can be CR 51 .
[0380] In formula HT-1, L 1It can 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. For example, in one or more embodiments, L 1 It may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, and / or a substituted or unsubstituted divalent carbazole group, etc., but the embodiments of the present disclosure are not limited thereto.
[0381] In formula HT-1, Y a Can be direct key, CR 52 R 53 or SiR 54 R 55 For example, it may refer to the two benzene rings connected to the nitrogen atom in formula HT-1 via a direct bond, or In formula HT-1, if Y a is a direct bond, then the second compound represented by formula HT-1 may include a carbazole moiety (for example, when Y a When is a direct bond, the second compound represented by Formula HT-1 may include a carbazole moiety).
[0382] In formula HT-1, Ar a It may be 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 a It may be a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and / or a substituted or unsubstituted biphenyl group, but the embodiments of the present disclosure are not limited thereto.
[0383] In formula HT-1, R 51 To R 55 and R are independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted sulfenyl, 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. In one or more embodiments, R is selected from 51 To R 55 One or more of them can each independently optionally bind to an adjacent group to form (or provide) a ring. For example, in some embodiments, R 51 To R 55 can each independently be hydrogen or deuterium. In some embodiments, R51 To R 55 Each may independently be an unsubstituted methyl group or an unsubstituted phenyl group.
[0384] In one or more embodiments, the second compound represented by Formula HT-1 may be any one (eg, one) selected from the compounds represented by Compound Group 2. The emission layer EML may include at least one selected from the compounds represented by Compound Group 2 as a hole transport host material.
[0385] Compound Group 2
[0386]
[0387]
[0388]
[0389] In the example compounds presented in compound group 2, "D" may refer to deuterium, and "Ph" may refer to substituted or unsubstituted phenyl. For example, in the example compounds presented in compound group 2, "Ph" may refer to unsubstituted phenyl.
[0390] 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.
[0391] Formula ET-1
[0392]
[0393] In formula ET-1, Z is selected from a To Z c At least one of them may be N, and the rest may be CR 56 For example, in one or more embodiments, selected from Z a To Z c Any one of them may be N, and the rest may all independently be CR 56 In these embodiments, the third compound represented by Formula ET-1 may include a pyridine moiety. In one or more embodiments, the compound selected from Z a To Z c Two of them can be N, and the rest can be CR 56 In these embodiments, the third compound represented by Formula ET-1 may include a pyrimidine moiety. In one or more embodiments, Z a To Z cAll may be N. In these embodiments, the third compound represented by Formula ET-1 may include a triazine moiety.
[0394] In formula ET-1, R 56 It 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.
[0395] In Formula ET-1, b1 to b3 may each independently be an integer of 0 to 10.
[0396] In formula ET-1, Ar b To Ar d and R and R are independently hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 ring carbon atoms. For example, in one or more embodiments, Ar b To Ar d Each may independently be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazolyl group.
[0397] In formula ET-1, L 2 To L 4 and L1 and L2 may 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. In one or more embodiments, if b1 to b3 are integers of 2 or more, then the plurality of L 2 To multiple L 4 Each of L1 and L2 may be independently 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 (for example, when b1 to b3 are integers of 2 or more, a plurality of L 2 To multiple L 4 and (ii) 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).
[0398] In one or more embodiments, the third compound may be any one selected from among the compounds in compound group 3. The light emitting device ED of one or more embodiments may include any one selected from among the compounds in compound group 3.
[0399] Compound Group 3
[0400]
[0401]
[0402]
[0403] In the example compounds presented in Compound Group 3, "D" refers to deuterium, and "Ph" refers to unsubstituted phenyl.
[0404] 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 (or provide) an exciplex. In the emission layer EML, the exciplex may be formed by a hole transport host and an electron transport host. In these embodiments, the triplet energy of the exciplex formed by the hole transport host and the electron transport host may correspond to the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the electron transport host and the highest occupied molecular orbital (HOMO) energy level of the hole transport host.
[0405] For example, in one or more embodiments, the absolute value of the triplet energy (T1) of the exciplex formed by the hole transport host and the electron transport host can be about 2.4 eV to about 3.0 eV. In one or more embodiments, the triplet energy of the exciplex can be a value smaller than the energy gap of each host material. The exciplex can have a triplet energy of about 3.0 eV or less, that is, less than the energy gap between the hole transport host and the electron transport host.
[0406] In one or more embodiments, the emission layer EML may include the fourth compound as described above in addition to the first to third compounds. The fourth compound may be used as a phosphorescence sensitizer of the emission layer EML. Energy may be transferred from the fourth compound to the first compound, thereby emitting light.
[0407] For example, in one or more embodiments, the emission layer EML may include an organic metal complex including platinum (Pt) as a central metal atom and a ligand connected to the central metal atom as a fourth compound. 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 a fourth compound:
[0408] Formula D-1
[0409]
[0410] In formula D-1, Q 1 To Q 4 can all independently be C or N.
[0411] In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms.
[0412] In formula D-1, L 11 To L 13 Can be directly connected, *-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. 11 To L 13 In the figure, “-*” refers to the part connected to C1 to C4.
[0413] In formula D-1, b1 to b3 may be independently 0 or 1. If b1 is 0, C1 and C2 may not be connected to each other. If b2 is 0, C2 and C3 may not be connected to each other. If b3 is 0, C3 and C4 may not be connected to each other.
[0414] In formula D-1, R 61 To R 66 and R are independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted sulfenyl, 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. In one or more embodiments, R is selected from 61 To R 66 One or more of them can be independently optionally combined to an adjacent group to form (or provide) a ring. In some embodiments, R 61 To R 66 Each may independently be a substituted or unsubstituted methyl group or a substituted or unsubstituted tert-butyl group.
[0415] In Formula D-1, d1 to d4 may each independently be an integer of 0 to 4. In Formula D-1, if each of d1 to d4 is 0, the fourth compound may not be 61 To R 64 Each of d1 to d4 is 4 and multiple R 61 To multiple R 64 The embodiment in which all R are hydrogen may be the same as the embodiment in which each of d1 to d4 is 0. When each of d1 to d4 is an integer of 2 or greater, the plurality of R61 To multiple R 64 can be the same or selected from multiple R 61 To multiple R 64 At least one of them may be different from the others.
[0416] In formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle represented by any one selected from C-1 to C-4:
[0417]
[0418] In C-1 to C-4, P 1 Can be C-* or CR 74 , P 2 Can be N-* or NR 81 , P 3 Can be N-* or NR 82 , and P 4 Can be C-* or CR 88 . R 71 To R 88 Each may 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-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and may be optionally bonded to an adjacent group to form (or provide) a ring.
[0419] In one or more embodiments, in C-1 to C-4, corresponds to a portion connected to Pt as a central metal atom, and "-*" corresponds to a portion connected to adjacent ring groups C1 to C4 or a linking group L 11 To L 13 part.
[0420] The emission layer EML of one or more embodiments may include a first compound as a fused polycyclic compound of the present disclosure and at least one selected from the second compound to the fourth compound. 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 (or provide) an exciplex, and energy may be transferred from the exciplex to the first compound, thereby emitting light.
[0421] 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 (or provide) an exciplex, and energy may be transferred from the exciplex to the fourth compound and the first compound, thereby emitting light. In some 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 an auxiliary dopant accelerates the energy transfer to the first compound as a light-emitting dopant, thereby increasing the emissivity of the first compound. Therefore, the emission layer EML of one or more embodiments may improve the emission efficiency. In one or more embodiments, if the energy transfer to the first compound is increased, the excitons formed in the emission layer EML are not accumulated inside the emission layer EML but emit light quickly, thereby reducing the degradation of the light-emitting device ED (for example, when the energy transfer to the first compound is increased, the excitons formed in the emission layer EML are not accumulated inside the emission layer EML but emit light quickly, thereby reducing the degradation of the light-emitting device ED. Therefore, the service life of the light-emitting element ED of one or more embodiments can be increased.
[0422] 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 concurrently (e.g., simultaneously) include the second compound and the third compound as two different hosts, the first compound emitting delayed fluorescence, and the fourth compound including an organic metal complex, thereby exhibiting excellent or suitable emission efficiency characteristics.
[0423] In one or more embodiments, the fourth compound represented by Formula D-1 may be selected from any one (e.g., one) of the compounds represented in Compound Group 4. The emission layer EML may include at least one (e.g., one or more) selected from the compounds represented in Compound Group 4 as a sensitizer material.
[0424] Compound Group 4
[0425]
[0426]
[0427] In the example compounds presented in Compound Group 4, "D" refers to deuterium.
[0428] 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, and the third compound, the content (e.g., amount) of the first compound relative to the total weight of the first compound, the second compound, and the third compound may be about 0.1 wt% to about 5 wt%. 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 may be increased, and thus the emission efficiency and the element life may be increased.
[0429] The content (e.g., amount) of the second compound and the third compound in the emission layer EML may be the remaining weight except for the weight of the first compound. For example, the content of the second compound and the third compound in the emission layer EML may be about 65 wt % to about 99.9 wt % relative to the total weight of the first compound, the second compound, and the third compound.
[0430] A weight ratio of the second compound to the third compound may be about 3:7 to about 7:3 in the total weight of the second compound and the third compound.
[0431] When the contents of the second compound and the third compound satisfy the above ratio, the charge balance characteristics in the emission layer EML are improved, so the emission efficiency and the element life can be increased. When the contents of the second compound and the third compound are outside the above ratio range, the charge balance in the emission layer EML is destroyed, so the emission efficiency may be reduced, and the element may be easily degraded.
[0432] In one or more embodiments, when the emission layer EML includes a 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 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 transfer from the host to the first compound as a light-emitting dopant can be increased, so that the luminescence ratio can be improved, and thus the emission 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 meet the above content (e.g., amount) ratio range, excellent or suitable emission efficiency and long service life of the light-emitting element ED can be achieved.
[0433] 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, At least one of anthracene derivatives, dehydrogenated benzanthracene derivatives, and benzo[9,10]phenanthrene derivatives. For example, in some embodiments, the emission layer EML may include one or more anthracene derivatives and / or one or more pyrene derivatives.
[0434] exist Figures 3 to 6 In each light-emitting element ED of the embodiment shown in , in addition to the above-mentioned host and dopant, the emission layer EML may further include a suitable host and / or 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 may be used as a fluorescent host material.
[0435] Formula E-1
[0436]
[0437] In formula E-1, R 31 To R 40 may be independently hydrogen, deuterium, halogen, substituted or unsubstituted silyl, substituted or unsubstituted thiol, substituted or unsubstituted oxy, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 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 may be optionally bonded to an adjacent group to form (or provide) a ring. In one or more embodiments, R is selected from 31 To R 40 One or more of them may each independently optionally bind to an adjacent group to form (or provide) a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring or an unsaturated heterocyclic ring.
[0438] In Formula E-1, c and d may each independently be an integer of 0 to 5.
[0439] The compound represented by formula E-1 may be any one selected from compound E1 to compound E19:
[0440]
[0441]
[0442] 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 may be used as a phosphorescent host material.
[0443] Formula E-2a
[0444]
[0445] In Formula E-2a, a may be an integer from 0 to 10, and L a It may 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 a is an integer of 2 or more, then the plurality of L a L and L 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 (for example, when a is an integer of 2 or more, a plurality of L a and (ii) 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).
[0446] In one or more embodiments, in Formula E-2a, A 1 To A 5 can be independently N or CR i . R a To R i may be independently hydrogen, deuterium, substituted or unsubstituted amine, substituted or unsubstituted thiol, substituted or unsubstituted oxy, 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 may be optionally bonded to an adjacent group to form (or provide) a ring. In some embodiments, R is selected from a To R i One or more of them may be optionally bonded to an adjacent group to form (or provide) a hydrocarbon ring or a heterocyclic ring containing N, O and / or S etc. as ring-forming atoms.
[0447] In one or more embodiments, in Formula E-2a, A 1 To A 5 (e.g., selected from A 1 To A 5 Two or three of them may be N, and the rest may be CR i .
[0448] Formula E-2b
[0449]
[0450] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazolyl group or a carbazolyl group substituted with an aromatic group having 6 to 30 ring carbon atoms. bIt may 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, b may be an integer from 0 to 10. If b is an integer of 2 or more, then the plurality of L b L and L 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 (for example, when b is an integer of 2 or more, a plurality of L b and (ii) 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).
[0451] The compound represented by formula E-2a or formula E-2b can be any one selected from the compounds of compound group E-2. However, the compounds listed in compound group E-2 are only examples, and the compounds represented by formula E-2a or formula E-2b are not limited to the compounds represented in compound group E-2.
[0452] Compound Group E-2
[0453]
[0454]
[0455] 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-carbazole-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(carbazole-9-yl)benzene (mCP), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF), 4,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA), and 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) as a host material. However, embodiments of the present disclosure are not limited thereto. For example, tris(8-hydroxyquinoline)aluminum (Alq 3)、9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyryl arylide (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH 2 ), hexaphenylcyclotrisiloxane (DPSiO 3 ) and / or octaphenylcyclotetrasiloxane (DPSiO 4 ) etc. can be used as the main material.
[0456] In one or more embodiments, the emission layer EML may include a compound represented by Formula Ma. The compound represented by Formula Ma may be used as a phosphorescent dopant material.
[0457] Formula Ma
[0458]
[0459] In formula Ma, Y 1 To Y 4 and Z 1 To Z 4 Can be CR independently 1 or N, and R 1 To R 4 Can be hydrogen, deuterium, substituted or unsubstituted amine, substituted or unsubstituted sulfenyl, substituted or unsubstituted oxy, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 ring carbon atoms, and can be optionally combined to adjacent groups to form (or provide) rings. In formula Ma, m is 0 or 1, and n is 2 or 3. In formula Ma, if m is 0, n is 3 (e.g., when m is 0, n is 3), and if m is 1, n is 2 (e.g., when m is 1, n is 2).
[0460] The compound represented by the formula Ma may be used as a phosphorescent dopant.
[0461] The compound represented by formula Ma may 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 Ma is not limited to the compounds represented by compound M-a1 to compound M-a25.
[0462]
[0463]
[0464]
[0465] In one or more embodiments, the emission layer EML may include a compound represented by any one selected from Formula Fa to Formula Fc. The compound represented by Formula Fa to Formula Fc may be used as a fluorescent dopant material.
[0466] Formula
[0467]
[0468] In formula Fa, R a To R j (e.g., selected from R a To R j The two of them may be independently substituted with *-NAr 1 Ar 2 . R a To R j Among them, the unsubstituted ones are *-NAr 1 Ar 2 The other groups of can each independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted amine, 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.
[0469] In *-NAr 1 Ar 2 in Ar 1 and Ar 2 and Ar may be independently substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms or substituted or unsubstituted heteroaryl groups having 2 to 30 ring carbon atoms. 1 and Ar 2 At least one of may be a heteroaryl group containing O or S as a ring-forming atom.
[0470] Formula Fb
[0471]
[0472] In formula Fb, R a and R bEach of Ar and Ar may be independently hydrogen, deuterium, 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 may be optionally bonded to an adjacent group to form (or provide) a ring. 1 To Ar 4 Each may independently be 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.
[0473] In Formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms. 1 To Ar 4 At least one of them may be a heteroaryl group containing O or S as a ring-constituting atom.
[0474] In Formula Fb, the number of rings represented by U and V may each independently be 0 or 1. For example, in Formula Fb, it means that if the number of U or V is 1, one ring constitutes a part of the condensed ring at the portion represented by U or V (for example, when the number of U or V is 1, one ring constitutes a part of the condensed ring at the portion represented by U or V), and if the number of U or V is 0, there is no ring represented by U or V (when the number of U or V is 0, there is no ring represented by U or V). For example, if the number of U is 0 and the number of V is 1 or if the number of U is 1 and the number of V is 0, the condensed ring having a fluorene core in Formula Fb may be a ring compound having four rings (when the number of U is 0 and the number of V is 1 or when the number of U is 1 and the number of V is 0, the condensed ring having a fluorene core in Formula Fb may be a ring compound having four rings). In one or more embodiments, if each number of U and V is 0, the fused ring with a fluorene core in Formula Fb may be a cyclic compound with three rings (when each number of U and V is 0, the fused ring with a fluorene core in Formula Fb may be a cyclic compound with three rings). In one or more embodiments, if each number of U and V is 1, the fused ring with a fluorene core in Formula Fb may be a cyclic compound with five rings (when each number of U and V is 1, the fused ring with a fluorene core in Fb may be a cyclic compound with five rings).
[0475] Formula Fc
[0476]
[0477] In Formula Fc, A1 and A 2 can be independently O, S, Se or NR m , and R m R 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 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To R 11 Each may independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted amine, substituted or unsubstituted boron, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 ring-forming carbon atoms, and may optionally bind to an adjacent group to form (or provide) a ring.
[0478] In one or more embodiments, in Formula Fc, A 1 and A 2 Each of the substituents independently may optionally bind to adjacent rings to form (or provide) a fused ring. 1 and A 2 can all independently be NR m , then in one or more embodiments, A 1 Can be combined with R 4 or R 5 To form (or provide) a ring (when A 1 and A 2 can all independently be NR m In one or more embodiments, A 1 Can be combined with R 4 or R 5 To form (or provide) a ring). In one or more embodiments, A 2 Can be combined with R 7 or R 8 To form (or provide) a ring.
[0479] In one or more embodiments, the emission layer EML may further include a styryl derivative (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)naphthalene-2-yl)vinyl)phenyl)- One or more of 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)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene and / or 1,4-bis(N,N-diphenylamino)pyrene), etc. are used as suitable dopant materials.
[0480] In one or more embodiments, the emission layer EML may further include a suitable phosphorescent dopant material. For example, a metal complex 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 a phosphorescent dopant. For example, bis(4,6-difluorophenylpyridine-N,C2') picolinyl iridium (III) (FIrpic), bis(2,4-difluorophenylpyridine)-tetrakis(1-pyrazolyl) borate iridium (III) (FIrpic), 6 ) or platinum octaethylporphyrin (PtOEP) may be used as a phosphorescent dopant. However, the embodiments of the present disclosure are not limited thereto.
[0481] In one or more embodiments, the emission layer EML may include a quantum dot material. In one or more embodiments, the quantum dot material may have a core / shell structure. The core of the quantum dot may be selected from II-VI group compounds, III-VI group compounds, I-III-VI group compounds, III-V group compounds, III-II-V group compounds, IV-VI group compounds, IV group elements, IV group compounds, and (e.g., any suitable) combinations thereof.
[0482] The 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; ternary compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, Cd ZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and mixtures thereof.
[0483] III-VI compounds can include binary compounds (such as In 2 S 3 and / or In 2 Se 3 ), ternary compounds (such as InGaS 3 and / or InGaSe 3 ) or (e.g., any suitable) combination thereof.
[0484] The I-III-VI group compound can be selected from: a ternary compound selected from AgInS, AgInS 2 、CuInS、CuInS 2 、AgGaS 2 、CuGaS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 and mixtures thereof; and / or quaternary compounds such as AgInGaS 2 and / or CuInGaS 2 .
[0485] The III-V compound may be selected from the group consisting of: a binary compound selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; a ternary compound 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; and a quaternary compound selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. In one or more embodiments, the III-V compound may also include a Group II metal. For example, InZnP or the like may be selected as the III-II-V group compound.
[0486] The IV-VI compound may be selected from the group consisting of: a binary compound selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe and mixtures thereof; a ternary compound selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and mixtures thereof; and a quaternary compound selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe and mixtures thereof. The IV group element may be selected from the group consisting of Si, Ge and mixtures thereof. The IV group compound may be a binary compound selected from the group consisting of SiC, SiGe and mixtures thereof.
[0487] 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 particle in a substantially uniform or non-uniform concentration distribution. For example, the formula refers to the type (species) of the element included in the compound, and the ratio of the elements in the compound may be different. For example, AgInGaS 2 Can refer to AgIn x Ga 1-x S 2 (where x is a real number between 0 and 1).
[0488] In one or more embodiments, the quantum dot may have a single structure or a core / shell dual structure in which the concentration of each element included in the quantum dot is substantially uniform. For example, the material included in the core may be different from the material included in the shell.
[0489] The shell of the quantum dot can be used as a protective layer to prevent or reduce the chemical denaturation of the core to maintain the semiconductor properties, and / or as a charge layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient in which the concentration of the element present in the shell decreases toward the center.
[0490] In some embodiments, quantum dots may have a core / shell structure comprising a core comprising nanocrystals and a shell around the core (e.g., surrounding the core) as described above. Examples of shells of quantum dots may include metal or non-metal oxides, semiconductor compounds, and / or (e.g., any suitable) combinations thereof.
[0491] For example, the metal or non-metal oxide used for the shell can be a binary compound (such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 and / or NiO) and / or ternary compounds (such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 and / or CoMn 2 O 4 ), but the embodiments of the present disclosure are not limited thereto.
[0492] In addition, examples of semiconductor compounds suitable as shells 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.
[0493] Each element included in a multi-component compound (such as a binary compound or a ternary compound) may exist in the particle in a substantially uniform or non-uniform concentration distribution. For example, the formula refers to the type (species) of the element included in the compound, and the ratio of the elements in the compound may be different.
[0494] The quantum dot can have a full width at half maximum (FWHM) of an emission spectrum of about 45 nm or less, about 40 nm or less, or about 30 nm or less, and within the above range, the color purity or color reproducibility of the quantum dot can be improved. In one or more embodiments, the light emitted by such a quantum dot is emitted in all directions so that a wide viewing angle can be improved.
[0495] In one or more embodiments, the form (or shape) of the quantum dots is not particularly limited as long as it is a form (or shape) utilized in the art. In some embodiments, quantum dots in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc. can be utilized.
[0496] When the size of the quantum dots is adjusted or the ratio of elements in the quantum dot compound is adjusted, the band gap of the quantum dots can be controlled, so that light within one or more suitable wavelength ranges can be obtained in the quantum dot emission layer. Therefore, the quantum dots as described above can be used (using different sizes of quantum dots or different ratios of elements in quantum dot compounds), so a light-emitting device that emits light of one or more suitable wavelengths can be realized. For example, adjusting the size of the quantum dots and / or the ratio of elements in the quantum dot compound can enable the quantum dots to emit red light, green light, and / or blue light. In one or more embodiments, the quantum dots can be configured to emit white light by combining one or more suitable colors of light.
[0497] exist Figures 3 to 6 In each of the light emitting elements ED of the embodiment shown in , the electron transport region ETR may be disposed 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.
[0498] The electron transport region ETR may have a single layer formed of a single material, 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.
[0499] 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 an electron transport layer ETL / electron injection layer EIL or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL are stacked in sequence (e.g., in the stated 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, a structure from about to about Thickness.
[0500] The electron transport region ETR may 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.
[0501] In one or more embodiments, the electron transport region ETR may include a compound represented by Formula ET-2:
[0502] Formula ET-2
[0503]
[0504] In formula ET-2, selected from X 1 To X 3 At least one of them can be N, and the rest are CR a . R a It 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 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To Ar 3 Each may 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.
[0505] In Formula ET-2, a to c may each independently be an integer from 0 to 10. In Formula ET-2, L 1 To L 3and L are each 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. In one or more embodiments, if a to c are each independently an integer of 2 or more, then the plurality of L 1 To multiple L 3 Each of L may be independently 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 (when a to c may be independently an integer of 2 or more, multiple L 1 To multiple L 3 and (ii) 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).
[0506] In some embodiments, the electron transport region ETR may include an anthracene compound. However, the embodiments of the present disclosure are not limited thereto. For example, in some embodiments, the electron transport region ETR may include, for example, a compound selected from tris(8-hydroxyquinoline)aluminum (Alq 3 ), 1,3,5-tris[(3-pyridyl)-phenyl-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-dinaphthylanthracene, 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 (Bph en), 3-(biphenyl-4-yl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinolinolato-10-hydroxy)beryllium (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB) and a mixture thereof.
[0507] In one or more embodiments, the electron transport region ETR may include at least one selected from compounds ET1 to ET36:
[0508]
[0509]
[0510]
[0511] In one or more embodiments, the electron transport region ETR may include a metal halide (such as LiF, NaCl, CsF, RbCl, RbI, CuI and / or KI), a lanthanide metal (such as Yb), or a co-deposited material of a metal halide and a lanthanide metal. For example, in some embodiments, the electron transport region ETR may include KI:Yb, RbI:Yb and / or LiF:Yb as a co-deposited material. In one or more embodiments, the electron transport region ETR may utilize a metal oxide (such as Li 2 O and / or BaO) or 8-hydroxy-quinoline lithium (Liq), etc., but the embodiments of the present disclosure are not limited thereto. In some embodiments, the electron transport region ETR can also be formed by a mixed material of an electron transport material and an insulating organic metal salt. The organic metal salt can be a material with an energy band gap of about 4eV or greater. For example, the organic metal salt can include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates and / or metal stearates.
[0512] In one or more embodiments, in addition to one or more of the above materials, the electron transport region ETR may also 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.
[0513] The electron transport region ETR may include one or more of the above-mentioned compounds of the electron transport region ETR in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.
[0514] When the electron transport region ETR includes the electron transport layer ETL, the electron transport layer ETL may have a thickness of about 100 Å. to about (For example, about to about ) thickness. If the thickness of the electron transport layer ETL satisfies the above 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.
[0515] The second electrode EL2 may be disposed on 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 the embodiments of the present disclosure are not limited thereto. For example, if the first electrode EL1 is an anode, the second electrode EL2 may be a cathode (when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode), and if the first electrode EL1 is a cathode, the second electrode EL2 may be an anode (when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode).
[0516] The second electrode EL2 may be a transmissive electrode, a transflective 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 (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO) and / or indium tin zinc oxide (ITZO), etc.).
[0517] When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W, a compound thereof, or a mixture thereof (e.g., AgMg, AgYb, or MgYb) or a material having a multilayer structure such as LiF / Ca or LiF / Al. In one or more embodiments, the second electrode EL2 may have a multilayer structure including a reflective film or a transflective film formed of one or more selected from 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 or more selected from the above metal materials, a combination of at least two metal materials selected from the above metal materials, and / or an oxide of the above metal materials, etc.
[0518] In some embodiments, the second electrode EL2 may be connected to the auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced (when the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced).
[0519] In one or more embodiments, a cap layer CPL may be further disposed on the second electrode EL2 of the light emitting element ED. The cap layer CPL may include a plurality of layers or a single layer.
[0520] In one or more embodiments, the cap layer CPL may be an organic layer or an inorganic layer. For example, if the cap layer CPL includes an inorganic material, the inorganic material may include an alkali metal compound (eg, LiF), an alkaline earth metal compound (eg, MgF 2 )、SiON、SiN x and / or SiO y etc. (When the cap layer CPL comprises an inorganic material, the inorganic material may include an alkali metal compound (such as LiF), an alkaline earth metal compound (such as MgF 2 )、SiON、SiN x and / or SiO y wait).
[0521] For example, in some embodiments, if the cap layer CPL includes an organic material, the organic material may include α-NPD, NPB, TPD, m-MTDATA, Alq 3 , CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), epoxy resin and / or acrylate (such as methacrylate), etc. (for example, when the cap layer CPL includes an organic material, the organic material may include α-NPD, NPB, TPD, m-MTDATA, Alq 3 , CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), epoxy resin and / or acrylate (such as methacrylate), etc.). However, the embodiments of the present disclosure are not limited thereto. For example, in one or more embodiments, the cap layer CPL may include at least one selected from compounds P1 to P5:
[0522]
[0523] In one or more embodiments, the refractive index of the cap layer CPL may be about 1.6 or greater. For example, in one or more embodiments, the refractive index of the cap layer CPL may be about 1.6 or greater with respect to light in a wavelength range of about 550 nm to about 660 nm.
[0524] Figures 7 to 10 Each of them is a cross-sectional view of a display device according to one or more embodiments of the present disclosure. Figures 7 to 10 When describing the display device of the embodiment, for the sake of brevity, the description of the display device already described is omitted. Figures 1 to 6 The repeated features described in will be mainly described only their differences.
[0525] Reference Figure 7 , the display device DD-a according to one or more embodiments may include a display panel DP including a display device layer DP-ED, a light control layer CCL and a color filter layer CFL arranged on the display panel DP. Figure 7 In one or more embodiments shown in , the display panel DP may include a base layer BS, a circuit layer DP-CL and a display device layer DP-ED disposed on the base layer BS, and the display device layer DP-ED may include a light emitting device ED.
[0526] The light emitting device ED may include a first electrode EL1, a hole transport region HTR on the first electrode EL1, an emission layer EML on the hole transport region HTR, an electron transport region ETR on the emission layer EML, and a second electrode EL2 on the electron transport region ETR. In one or more embodiments, as described above, Figures 3 to 6 The structure of any one of the light emitting elements ED can be similarly applied to Figure 7 The structure of the light emitting device ED shown in FIG.
[0527] 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 condensed polycyclic compound of one or more embodiments described above.
[0528] Reference Figure 7 , the emission layer EML can be arranged in the opening OH defined in the pixel defining film PDL. For example, the emission layer EML divided by the pixel defining film PDL and correspondingly set to each of the light-emitting regions PXA-R, PXA-G and PXA-B can emit light in substantially the same wavelength range. In the display device DD-a of one or more embodiments, the emission layer EML can emit blue light. In one or more embodiments, the emission layer EML can be set as a common layer in the entire light-emitting regions PXA-R, PXA-G and PXA-B.
[0529] The light control layer CCL may be arranged 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 be a layer including quantum dots or a layer including phosphors.
[0530] The light-control layer CCL may include a plurality of light-control parts CCP1, CCP2, and CCP3. The light-control parts CCP1, CCP2, and CCP3 may be spaced and / or separated from each other.
[0531] Reference Figure 7, the separation pattern BMP may be disposed between the light-control parts CCP1 , CCP2 , and CCP3 that are separated and / or isolated from each other, but the embodiments of the present disclosure are not limited thereto. Figure 7 It is shown that the separation pattern BMP does not overlap the light-control parts CCP1 , CCP2 , and CCP3 , but in some embodiments, at least a portion of the edges of the light-control parts CCP1 , CCP2 , and CCP3 may overlap the separation pattern BMP.
[0532] The light control layer CCL may include a first light control part CCP1, a second light control part CCP2 and a third light control part CCP3, the first light control part CCP1 including a first quantum dot QD1 that converts a first color light provided from the light emitting device ED into a second color light, the second light control part CCP2 including a second quantum dot QD2 that converts the first color light into a third color light, and the third light control part CCP3 transmits the first color light.
[0533] In one or more embodiments, the first light control unit CCP1 may provide red light as the second color light, and the second light control unit CCP2 may provide green light as the third color light. The third light control unit 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. With respect to quantum dots QD1 and QD2, the same contents as described above regarding quantum dots may be applied.
[0534] In one or more embodiments, the light control layer CCL may further include a scatterer SP. The first light control part CCP1 may include a first quantum dot QD1 and a scatterer SP, the second light control part CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third light control part CCP3 may not include (e.g., may exclude) any quantum dot but include a scatterer SP.
[0535] The scatterer SP may be inorganic particles. For example, the scatterer SP may include TiO 2 、ZnO、Al 2 O 3 、SiO 2 In one or more embodiments, the scatterer SP may include at least one selected from TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow spherical silica, or may be selected from TiO 2 、ZnO、Al 2 O3 、SiO 2 A mixture of at least two materials selected from the group consisting of quartz and hollow spherical silica.
[0536] The first light control part CCP1, the second light control part CCP2 and the third light control part CCP3 may respectively include base resins BR1, BR2 and BR3 in which quantum dots QD1 and QD2 and scatterers SP are dispersed. In one or more embodiments, the first light control part CCP1 may include the first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second light control part CCP2 may include the second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third light control part CCP3 may include the scatterers SP dispersed in the third base resin BR3.
[0537] The matrix resins BR1, BR2 and BR3 are media in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and can be formed by one or more suitable resin components that can generally be referred to as adhesives. For example, the matrix resins BR1, BR2 and BR3 can each independently be an acrylic resin, a urethane resin, a silicone resin and / or an epoxy resin, etc. The matrix resins BR1, BR2 and BR3 can be transparent resins. In one or more embodiments, the first matrix resin BR1, the second matrix resin BR2 and the third matrix resin BR3 can be the same or different from each other.
[0538] In one or more embodiments, the light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 may be used to prevent or reduce the penetration of moisture and / or oxygen (hereinafter, referred to as "moisture / oxygen"). The barrier layer BFL1 may block or reduce the exposure of the light control parts CCP1, CCP2, and CCP3 to moisture / oxygen. In one or more embodiments, the barrier layer BFL1 may cover the light control parts CCP1, CCP2, and CCP3. In one or more embodiments, the barrier layer BFL2 may be disposed between the light control parts CCP1, CCP2, and CCP3 and a portion of the color filter layer CFL other than the barrier layer BFL2.
[0539] The barrier layers BFL1 and BFL2 may include at least one inorganic layer. For example, in some embodiments, the barrier layers BFL1 and BFL2 may include an inorganic material. For example, the barrier layers BFL1 and BFL2 may 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 film ensuring transmittance, etc. In one or more embodiments, the barrier layers BFL1 and BFL2 may also include an organic layer. The barrier layers BFL1 and BFL2 may be formed of a single layer or a plurality of layers.
[0540] In the display device DD-a of one or more embodiments, the color filter layer CFL may be disposed on the light control layer CCL. For example, in some embodiments, the color filter layer CFL may be disposed directly on the light control layer CCL. In these embodiments, the blocking layer BFL2 may not be provided.
[0541] The color filter layer CFL may include filters CF1, CF2, and CF3. The color filter layer CFL may include a first filter CF1 configured to transmit a second color light, a second filter CF2 configured to transmit a third color light, and a third filter CF3 configured to transmit the first color light. For example, in some embodiments, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. The filters CF1, CF2, and CF3 may each include a polymer photosensitive resin and a pigment and / or a dye. The first filter CF1 may include a red pigment and / or a red dye, the second filter CF2 may include a green pigment and / or a green dye, and the third filter CF3 may include a blue pigment and / or a blue dye.
[0542] In one or more embodiments, the third filter CF3 may not include (e.g., may exclude) any pigment and / or dye. The third filter CF3 may include a polymer photosensitive resin and may not include (e.g., may exclude) any pigment and / or dye. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.
[0543] Furthermore, in some embodiments, the first filter CF1 and the second filter CF2 may both be yellow filters. The first filter CF1 and the second filter CF2 may not be separated but may be provided as one filter.
[0544] In one or more embodiments, the color filter layer CFL may further include a light shielding portion. The light shielding portion may be a black matrix. The light shielding portion 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 portion may prevent or reduce light leakage and may separate the boundaries between adjacent filters CF1, CF2, and CF3.
[0545] The first, second, and third filters CF1, CF2, and CF3 may be arranged corresponding to the red, green, and blue emission regions PXA-R, PXA-G, and PXA-B, respectively.
[0546] 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 that provides a base surface on which the color filter layer CFL and / or the 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. In one or more embodiments, the base substrate BL may not be provided.
[0547] Figure 8 1 is a cross-sectional view showing a portion of a display device DD-TD according to one or more embodiments. In the display device DD-TD, 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 sequentially stacked between the first electrode EL1 and the second electrode EL2 in a thickness direction. The light emitting structures OL-B1, OL-B2, and OL-B3 may each include an emission layer EML ( Figure 7 ) and a hole transport region HTR (HTR) with an emission layer EML disposed therebetween. Figure 7 ) and the electron transport region ETR ( Figure 7 ).
[0548] For example, in some embodiments, the light emitting devices ED-BT included in the display devices DD-TD may be light emitting devices having a tandem structure and including a plurality of emission layers.
[0549] exist Figure 8 In one or more embodiments shown in , all light beams emitted from the light emitting structures OL-B1, OL-B2, and OL-B3, respectively, may be blue light. However, the embodiments of the present disclosure are not limited thereto, and the light beams emitted from the light emitting structures OL-B1, OL-B2, and OL-B3, respectively, may have wavelength ranges different from each other. For example, in one or more embodiments, a light emitting device ED-BT including a plurality of light emitting structures OL-B1, OL-B2, and OL-B3 emitting light beams having wavelength ranges different from each other may emit white light (e.g., combined white light).
[0550] The charge generation layers CGL1 and CGL2 may be arranged between two of the adjacent light emitting structures OL-B1, OL-B2 and OL-B3, respectively. The charge generation layers CGL1 and CGL2 may include a p-type or p-type charge (e.g., P charge) generation layer and / or an n-type or n-type charge (e.g., N charge) generation layer. At least one of the light emitting structures OL-B1, OL-B2 and OL-B3 included in the display device DD-TD of one or more embodiments may include the fused polycyclic compound of one or more embodiments described above. For example, in one or more embodiments, at least one of the multiple emission layers included in the light emitting element ED-BT (e.g., at least one selected from the multiple emission layers included in the light emitting element ED-BT) may include the fused polycyclic compound of the embodiment.
[0551] Reference Fig. 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 each of which two emission layers are stacked. Figure 2 Compared with the display device DD shown in Fig. 9 The display device DD-b shown in FIG. 1 is different in that the first to third light-emitting devices ED-1, ED-2, and ED-3 each include 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.
[0552] 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. In addition, 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 auxiliary part OG may be separately arranged 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.
[0553] The emission auxiliary part OG may include a single layer or multiple layers. The emission auxiliary part OG may include a charge generation layer. In one or more embodiments, the emission auxiliary part OG may include an electron transport region, a charge generation layer, and a hole transport region stacked sequentially (e.g., in the stated order). The emission auxiliary part OG may be set as a common layer in all of the 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 auxiliary part OG may be set by being patterned within an opening OH defined in the pixel defining film PDL.
[0554] The first red emission layer EML-R1, the first green emission layer EML-G1, and the first blue emission layer EML-B1 may be disposed between the emission auxiliary portion 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 be disposed between the hole transport region HTR and the emission auxiliary portion OG.
[0555] 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 auxiliary portion OG, a first red emission layer EML-R1, an electron transport region ETR, and a second electrode EL2 stacked in sequence (e.g., in the stated 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 auxiliary portion OG, a first green emission layer EML-G1, an electron transport region ETR, and a second electrode EL2 stacked in sequence (e.g., in the stated 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 auxiliary portion OG, a first blue emission layer EML-B1, an electron transport region ETR, and a second electrode EL2 stacked in sequence (e.g., in the stated order).
[0556] In one or more embodiments, the optical auxiliary layer PL may be arranged on the display device layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be arranged on the display panel DP to control the light reflected within the display panel DP due to external light. In some embodiments, the optical auxiliary layer PL may not be provided in the display device DD-b.
[0557] Included in Fig. 9At least one emission layer in the display device DD-b of one or more embodiments shown in the figure may include the fused polycyclic compound of one or more embodiments described above. 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 of one or more embodiments.
[0558] and Figure 8 and Fig. 9 different, Fig.10 The display device DD-c is shown to include 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-C1, OL-B1, OL-B2 and OL-B3 stacked between the first electrode EL1 and the second electrode EL2 in the thickness direction. The charge generation layers CGL1, CGL2 and CGL3 may be individually arranged between the first to fourth light emitting structures OL-C1, OL-B1, OL-B2 and OL-B3. In some embodiments, among the four light emitting structures, the second to fourth light emitting structures OL-B1, OL-B2 and OL-B3 may all emit blue light, and the first 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-C1, OL-B1, OL-B2 and OL-B3 may all emit light beams in different wavelength regions.
[0559] The charge generation layers CGL1, CGL2 and CGL3 arranged between adjacent light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1 may include p-type or p-type charge (e.g., P charge) generation layers and / or n-type or n-type charge (e.g., N charge) generation layers.
[0560] 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 of the above-mentioned one or more embodiments. For example, in one or more embodiments, at least one selected from the second to fourth light emitting structures OL-B1, OL-B2, and OL-B3 may include the fused polycyclic compound of the above-mentioned one or more embodiments.
[0561] The above-mentioned light-emitting device / light-emitting element ED according to one or more embodiments of the present disclosure may include the fused polycyclic compound of one or more embodiments in at least one functional layer arranged between the first electrode EL1 and the second electrode EL2, and thus may exhibit excellent or suitable luminous efficiency and improved lifespan. For example, the fused polycyclic compound according to one or more embodiments may be included in the emission layer EML of the light-emitting element ED of one or more embodiments, and the light-emitting element ED of one or more embodiments may exhibit a long lifespan.
[0562] In one or more embodiments, the electronic device may include a display device including a plurality of light emitting devices and a control unit for controlling the display device. The electronic device of one or more embodiments may be a device activated according to an electrical signal. The electronic device may include a display device of one or more suitable embodiments. For example, the electronic device may include not only large electronic devices such as televisions, monitors, or external 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.
[0563] Fig.11 1 is a diagram showing a vehicle AM in which first to fourth display devices DD-1, DD-2, DD-3, and DD-4 are arranged. At least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include the same as described in reference Figure 1 , Figure 2 and Figures 7 to 10 The described display devices DD, DD-a, DD-TD, DD-b and / or DD-c are of substantially the same construction.
[0564] Fig.11 Vehicle AM is shown, but this is an 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. In one or more embodiments, at least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 selected from the display devices DD, DD-TD, DD-a, DD-b, and / or DD-c of one or more embodiments may be adopted in a personal computer, a laptop computer, a personal digital terminal, a game console, a portable electronic device, a television, a monitor, and / or an external billboard, etc. These are provided only as examples, so unless departing from the present disclosure, the display device may be adopted in other electronic devices.
[0565] 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 reference Figures 3 to 6 The light-emitting element ED of one or more embodiments described. The light-emitting element ED of one or more embodiments may include the fused polycyclic compound of one or more embodiments. At least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 includes a light-emitting element ED including the fused polycyclic compound of one or more embodiments, and thus may have an increased display life.
[0566] Reference Fig.11 The vehicle AM may include a steering wheel HA and a gear GR for driving the vehicle AM. In addition, the vehicle AM may include a front window GL arranged to face the driver.
[0567] The first display device DD-1 may be arranged in a first area overlapping the steering wheel HA. For example, the first display device DD-1 may be a digital cluster displaying 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 be indicated as digital images.
[0568] The second display device DD-2 can be arranged in a second area facing the driver's seat and overlapping with the front window GL. The driver's seat can be a seat in which the steering wheel HA faces. For example, the second display device DD-2 can be a head-up display (HUD) that displays the second information of the vehicle AM. The second display device DD-2 can be optically transparent. The second information can include a digital number indicating the driving speed, and can also include information such as the current time. In some embodiments, the second information of the second display device DD-2 can be projected onto the front window GL for display.
[0569] The third display device DD-3 may be arranged in a third area adjacent to the vehicle 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 central information display (CID) for the vehicle AM for displaying third information. The passenger seat may be separated and / or separated from the driver's seat and the vehicle GR is arranged between the passenger seat and the driver's seat. The third information may include information about traffic (e.g., navigation information), information about playing music or radio or video (or images), and / or information about the temperature inside the vehicle AM, etc.
[0570] The fourth display device DD-4 may be separated and / or apart from the steering wheel HA and the gear GR, and may be arranged in a fourth area adjacent to one side of the vehicle AM. For example, the fourth display device DD-4 may be a digital side mirror that displays the fourth information. The fourth display device DD-4 may display an image outside the vehicle AM taken by a camera module CM arranged outside the vehicle AM. The fourth information may include an image outside the vehicle AM.
[0571] The above-mentioned first to fourth information may be examples, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may also display information about the interior and exterior of the vehicle AM. The first to fourth information may include different information. However, the embodiments of the present disclosure are not limited thereto, and a portion of the first to fourth information may include the same information as each other.
[0572] Hereinafter, the fused polycyclic compound according to one or more embodiments of the present disclosure and the light-emitting element of one or more embodiments will be specifically explained with reference to one or more embodiments and comparative examples. In addition, the embodiments are only for explanation to help understand the present disclosure, and the scope of the present disclosure is not limited thereto.
[0573] Example
[0574] 1. Synthesis of fused polycyclic compounds
[0575] First, the synthesis method of the fused polycyclic compound according to one or more embodiments will be explained in more detail by illustrating the synthesis methods of Compound 4, Compound 30, Compound 61, Compound 84, and Compound 171. In addition, the synthesis method of the fused polycyclic compound explained hereinafter is an exemplary embodiment, and the synthesis method of the fused polycyclic compound according to one or more embodiments of the present disclosure is not limited to the exemplary embodiment.
[0576] (1) Synthesis of Compound 4
[0577] Synthesis of intermediate 4-1
[0578]
[0579] 1,3-Dibromo-5-(tert-butyl)benzene (1 equivalent), 2-phenyldibenzo[b,d]furan-1-amine (2 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.1 equivalents) and sodium tert-butoxide (3 equivalents) were dissolved in toluene and stirred at about 110 degrees Celsius for about 12 hours. After cooling, the resultant was diluted with ethyl acetate and washed three times with water, and the organic layer obtained by layer separation was purified by anhydrous MgSO 4Drying and then drying under reduced pressure. The crude product was purified by column chromatography using dichloromethane (MC) and n-hexane as eluents to obtain Intermediate 4-1 (yield: 76%).
[0580] Synthesis of intermediate 4-2
[0581]
[0582] Intermediate 4-1 (1 equivalent), 9-(3-bromophenyl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (3 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.15 equivalents), tri-tert-butylphosphine (0.3 equivalents) and sodium tert-butoxide (5 equivalents) were dissolved in o-xylene and stirred at about 150 degrees Celsius for about 48 hours. After cooling, the resultant was diluted with ethyl acetate and washed three times with water, and the organic layer obtained by layer separation was purified by anhydrous MgSO 4 Drying, and then drying under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane as eluents to obtain Intermediate 4-2 (yield: 32%).
[0583] Synthesis of compound 4
[0584]
[0585] Intermediate 4-2 (1 equivalent) was dissolved in o-dichlorobenzene and cooled to about 0 °C, and BBr was slowly injected under nitrogen atmosphere. 3 (3 equivalents). After the addition was completed, the temperature was raised to about 180 degrees Celsius, followed by stirring for about 24 hours. After cooling, triethylamine was slowly added to the flask containing the reaction product to quench the reaction, and ethanol was added to precipitate. The precipitate was filtered to obtain the reaction product. The solid thus obtained was purified by column chromatography using MC and n-hexane as eluents, and then recrystallized from toluene and acetone to obtain compound 4 (yield: 7%).
[0586] (2) Synthesis of Compound 30
[0587] Synthesis of Intermediate 30-1
[0588]
[0589] 1,3-Dibromo-5-(tert-butyl)benzene (1 equivalent), 2,4-diphenyldibenzo[b,d]furan-1-amine (2 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.1 equivalents) and sodium tert-butoxide (3 equivalents) were dissolved in toluene and stirred at about 110 degrees Celsius for about 12 hours. After cooling, the resultant was diluted with ethyl acetate and washed three times with water, and the organic layer obtained by layer separation was purified by anhydrous MgSO4 Drying and then drying under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane as eluents to obtain Intermediate 30-1 (yield: 81%).
[0590] Synthesis of Intermediate 30-2
[0591]
[0592] Intermediate 30-1 (1 equivalent), 9-(3-bromophenyl)-3-phenyl-9H-carbazole-1,2,4,5,6,7,8-d7 (3 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.15 equivalents), tri-tert-butylphosphine (0.3 equivalents) and sodium tert-butoxide (5 equivalents) were dissolved in o-xylene and stirred at about 150 degrees Celsius for about 48 hours. After cooling, the resultant was diluted with ethyl acetate and washed three times with water, and the organic layer obtained by layer separation was purified by anhydrous MgSO 4 Drying and then drying under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane as eluents to obtain Intermediate 30-2 (yield: 41%).
[0593] Synthesis of compound 30
[0594]
[0595] Intermediate 30-2 (1 equivalent) was dissolved in o-dichlorobenzene and cooled to about 0 °C, and BBr was slowly injected under nitrogen atmosphere. 3 (3 equivalents). After the addition was completed, the temperature was raised to about 180 degrees Celsius, followed by stirring for about 24 hours. After cooling, triethylamine was slowly added to the flask containing the reaction product to quench the reaction, and ethanol was added to precipitate. The precipitate was filtered to obtain the reaction product. The solid thus obtained was purified by column chromatography using MC and n-hexane as eluents, and then recrystallized from toluene and acetone to obtain compound 30 (yield: 5%).
[0596] (3) Synthesis of Compound 61
[0597] Synthesis of Intermediate 61-1
[0598]
[0599] 1,3-Dibromo-5-(tert-butyl)benzene (1 equivalent), N-([1,1'-biphenyl]-4-yl)-2,4-diphenyldibenzo[b,d]furan-1-amine (0.8 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), ([1,1'-binaphthyl]-2,2'-diyl)bis(diphenylphosphine) (BINAP) (0.1 equivalent) and sodium tert-butoxide (3 equivalents) were dissolved in toluene and stirred at about 80 degrees Celsius for about 12 hours. After cooling, the resultant was diluted with ethyl acetate and washed three times with water, and the organic layer obtained by layer separation was subjected to anhydrous MgSO 4 Drying, and then drying under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane as eluents to obtain Intermediate 61-1 (yield: 62%).
[0600] Synthesis of Intermediate 61-2
[0601]
[0602] Intermediate 61-1 (1 equivalent), N-(3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-2,4-diphenyldibenzo[b,d]furan-1-amine (1.2 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.1 equivalents) and sodium tert-butoxide (3 equivalents) were dissolved in toluene and stirred at about 110 degrees Celsius for about 16 hours. After cooling, the resultant was diluted with ethyl acetate and washed three times with water, and the organic layer obtained by layer separation was purified by anhydrous MgSO 4 Drying, and then drying under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane as eluents to obtain Intermediate 61-2 (yield: 71%).
[0603] Synthesis of compound 61
[0604]
[0605] Intermediate 61-2 (1 equivalent) was dissolved in o-dichlorobenzene and cooled to about 0 °C, and BBr was slowly injected under nitrogen atmosphere. 3 (3 equivalents). After the addition was completed, the temperature was raised to about 180 degrees Celsius, followed by stirring for about 24 hours. After cooling, triethylamine was slowly added to the flask containing the reaction product to quench the reaction, and ethanol was added to precipitate. The precipitate was filtered to obtain the reaction product. The solid thus obtained was purified by column chromatography using MC and n-hexane as eluents, and then recrystallized from toluene and acetone to obtain compound 61 (yield: 12%).
[0606] (4) Synthesis of Compound 84
[0607] Synthesis of Intermediate 84-1
[0608]
[0609] 2-Bromo-4-(tert-butyl)dibenzo[b,d]furan-1-amine (1 equivalent), dibenzo[b,d]furan-4-ylboronic acid (2 equivalents), Pd(PPh 3 ) 4 (0.05 equivalent) and K 2 CO 3 (3 equivalents) was dissolved in a mixed solution of water and tetrahydrofuran (THF) at a volume ratio of 2:1 and stirred at about 80 degrees Celsius for about 12 hours. After cooling, the resultant was diluted with ethyl acetate and washed three times with water, and the organic layer obtained by layer separation was purified by anhydrous MgSO 4 Drying, and then drying under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane as eluents to obtain Intermediate 84-1 (yield: 79%).
[0610] Synthesis of Intermediate 84-2
[0611]
[0612] 1,3-Dibromo-5-(tert-butyl)benzene (1 equivalent), Intermediate 84-1 (2 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.1 equivalents) and sodium tert-butoxide (3 equivalents) were dissolved in toluene and stirred at about 110 degrees Celsius for about 12 hours. After cooling, the resultant was diluted with ethyl acetate and washed three times with water, and the organic layer obtained by layer separation was purified by anhydrous MgSO 4 Drying, and then drying under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane as eluents to obtain Intermediate 84-2 (yield: 83%).
[0613] Synthesis of Intermediate 84-3
[0614]
[0615] Intermediate 84-2 (1 equivalent), 9-(3'-bromo-[1,1'-biphenyl]-4-yl)-9H-carbazole (3 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.15 equivalents), tri-tert-butylphosphine (0.3 equivalents) and sodium tert-butoxide (5 equivalents) were dissolved in o-xylene and stirred at about 150 degrees Celsius for about 48 hours. After cooling, the resultant was diluted with ethyl acetate and washed three times with water, and the organic layer obtained by layer separation was purified by anhydrous MgSO 4Drying, and then drying under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane as eluents to obtain Intermediate 84-3 (yield: 32%).
[0616] Synthesis of compound 84
[0617]
[0618] Intermediate 84-3 (1 equivalent) was dissolved in o-dichlorobenzene and cooled to about 0 °C, and BBr was slowly injected under nitrogen atmosphere. 3 (3 equivalents). After the addition was completed, the temperature was raised to about 180 degrees Celsius, followed by stirring for about 24 hours. After cooling, triethylamine was slowly added to the flask containing the reaction product to quench the reaction, and ethanol was added to precipitate. The precipitate was filtered to obtain the reaction product. The solid thus obtained was purified by column chromatography using MC and n-hexane as eluents, and then recrystallized from toluene and acetone to obtain compound 84 (yield: 10%).
[0619] (5) Synthesis of Compound 171
[0620] Synthesis of Intermediate 171-1
[0621]
[0622] 2'-bromospiro[fluorene-9,9'-xanthene] (1 equivalent), (3,5-dichlorophenyl)boronic acid (1 equivalent), Pd(PPh 3 ) 4 (0.05 equivalent) and K 2 CO 3 (3 equivalents) was dissolved in a mixed solution of water and THF at a volume ratio of 2:1 and stirred at about 80 degrees Celsius for about 12 hours. After cooling, the resultant was diluted with ethyl acetate and washed three times with water, and the organic layer obtained by layer separation was purified by anhydrous MgSO 4 Drying and then drying under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane as eluents to obtain Intermediate 171-1 (yield: 74%).
[0623] Synthesis of Intermediate 171-2
[0624]
[0625] Intermediate 171-1 (1 equivalent), 4-(tert-butyl)-2-phenyl-N-(5'-phenyl-[1,1':3',1"-terphenyl]-4-yl)dibenzo[b,d]furan-1-amine (0.8 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), BINAP (0.1 equivalent) and sodium tert-butoxide (3 equivalents) were dissolved in toluene and stirred at about 90 degrees Celsius for about 12 hours. After cooling, the resultant was diluted with ethyl acetate and washed three times with water, and the organic layer obtained by layer separation was purified by anhydrous MgSO 4 Drying and then drying under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane as eluents to obtain Intermediate 171-2 (yield: 58%).
[0626] Synthesis of Intermediate 171-3
[0627]
[0628] Intermediate 171-2 (1 equivalent), N-([1,1'-biphenyl]-4-yl)-4-(tert-butyl)-2-phenyldibenzo[b,d]furan-1-amine (1.1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.1 equivalent) and sodium tert-butoxide (3 equivalents) were dissolved in toluene and stirred at about 110 degrees Celsius for about 16 hours. After cooling, the resultant was diluted with ethyl acetate and washed three times with water, and the organic layer obtained by layer separation was purified by anhydrous MgSO 4 Drying and then drying under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane as eluents to obtain Intermediate 171-3 (yield: 72%).
[0629] Synthesis of compound 171
[0630]
[0631] Intermediate 171-3 (1 equivalent) was dissolved in o-dichlorobenzene and cooled to about 0 °C, and BBr was slowly injected under nitrogen atmosphere. 3 (3 equivalents). After the addition was completed, the temperature was raised to about 180 degrees Celsius, followed by stirring for about 24 hours. After cooling, triethylamine was slowly added to the flask containing the reaction product to quench the reaction, and ethanol was added to precipitate. The precipitate was filtered to obtain the reaction product. The solid thus obtained was purified by column chromatography using MC and n-hexane as eluents, and then recrystallized from toluene and acetone to obtain compound 171 (yield: 11%).
[0632] 2. Manufacturing and evaluation of light-emitting components
[0633] A light-emitting element of one or more embodiments including a fused polycyclic compound of one or more embodiments in an emission layer is manufactured by the method described herein. The light-emitting elements of Examples 1 to 5 are manufactured using the fused polycyclic compounds of Example Compound 4, Example Compound 30, Example Compound 61, Example Compound 84, and Example Compound 171 as dopant materials for the emission layer, respectively. Comparative Examples 1 to 4 correspond to light-emitting elements manufactured using Comparative Compounds C1 to C4 as dopant materials for the emission layer, respectively.
[0634] Example compounds
[0635]
[0636] Comparative compounds
[0637]
[0638]
[0639] Manufacturing of light-emitting components
[0640] In order to manufacture the light emitting elements of the examples and the comparative examples, a layer of about 15 Ω / cm 2 A glass substrate of an ITO electrode (product of Corning Incorporated) was cut into a size of about 50 mm × 50 mm × 0.7 mm, cleaned with ultrasound in isopropyl alcohol and pure water for about 5 minutes each, exposed to ultraviolet rays for about 30 minutes, cleaned by exposure to ozone to provide an anode, and the anode was mounted in a vacuum evaporation apparatus.
[0641] On the anode, NPD is deposited to form (or provide) a layer having a thickness of about 300 angstroms. A hole injection layer having a thickness of about , and on the hole injection layer, H-1-1 is deposited to form (or provide) a hole injection layer having a thickness of about Then, on the hole transport layer, CzSi is deposited to form (or provide) a hole transport layer having a thickness of about The thickness of the emission auxiliary layer is .
[0642] Then, a host mixture obtained by mixing the second compound and the third compound according to one or more embodiments at a weight ratio of about 1:1, a fourth compound, and an exemplary compound or a comparative compound are co-deposited at a weight ratio of about 85:14:1 to form (or provide) a nanostructured carbon nanotube having about 100% carbon nanotubes. and on the emission layer, TSPO1 is deposited to form (or provide) a thin film having a thickness of about Then, on the hole blocking layer, TPBi is deposited to form (or provide) a layer having a thickness of about An electron transport layer having a thickness of about 1000 nm is formed, and on the electron transport layer, LiF is deposited to form (or provide) a layer having a thickness of about 1000 nm. Then, an electron injection layer having a thickness of about A second electrode with a thickness of 1000 Å is formed to form (or provide) a LiF / Al electrode.
[0643] All layers were formed by vacuum deposition. Meanwhile, HT36 was used as the second compound among the compounds in compound group 2, ETH66 was used as the third compound among the compounds in compound group 3, and AD-38 was used as the fourth compound among the compounds in compound group 4.
[0644] The compounds used to produce each of the light-emitting elements of Examples and Comparative Examples are shown below. The following materials were used after purchasing commercial products and performing sublimation purification.
[0645]
[0646] Evaluation of properties of light-emitting elements
[0647] The characterization data of Compound 4, Compound 30, Compound 61, Compound 84 and Compound 171 are shown in Table 1.
[0648] Table 1
[0649]
[0650] The emission efficiency and element life of each of the light-emitting elements manufactured by using Compound 4, Compound 30, Compound 61, Compound 84 and Compound 171 and Comparative Compounds C1 to Comparative Compounds C4 are evaluated. In Table 2, the evaluation results of each of the light-emitting elements of Examples 1 to 5 and Comparative Examples 1 to Comparative Examples 4 are shown. In order to evaluate the properties of each of the light-emitting elements manufactured in the examples and comparative examples, the driving voltage and current density were measured using a V7000 OLED IVL test system (Polaronix). In order to evaluate the properties of each of the light-emitting elements manufactured in Examples 1 to 5 and Comparative Examples 1 to Comparative Examples 4, the current density at about 10 mA / cm 2 The driving voltage and emission efficiency (cd / A) at a current density of about 10 mA / cm 2 While continuously driving at a current density of 1.5 Å, the time taken from the initial value of the luminance to about 95% of the initial value of the luminance was regarded as the relative element life (ie, life ratio (T95)) with respect to Comparative Example 1 for evaluation.
[0651] Table 2
[0652]
[0653] Referring to the results of Table 2, it can be confirmed that, when compared with the comparative examples, the examples of the light-emitting elements using the fused polycyclic compound according to one or more embodiments of the present disclosure as the light-emitting material all show reduced driving voltage and improved emission efficiency and life characteristics.
[0654] Since the example compounds each include a first substituent at a nitrogen atom constituting a condensed ring, a boron atom can be effectively protected, and high efficiency and long life can be achieved.
[0655] The example compounds all include a first substituent (which is a dibenzofuran moiety or a dibenzothiophene moiety) connected to a nitrogen atom of a fused ring core having a boron atom as the center. The first substituent is connected to the first nitrogen atom at the carbon of position 1 of the dibenzofuran moiety or the dibenzothiophene moiety. In the first substituent, the second substituent is an aryl or heteroaryl group, substituted at the 2-position carbon of the dibenzofuran moiety or the dibenzothiophene moiety. The fused polycyclic compound of one or more embodiments includes a first substituent connected to the first nitrogen atom, and the triangular planar structure of the boron atom can be effectively maintained by the steric hindrance effect of the first substituent with a large spatial volume. The boron atom has an electron-deficient property due to an empty p orbital, and can form a bond with other nucleophiles to change its structure to a tetrahedral structure, which may be a factor that degrades the light-emitting element. According to the present disclosure, the fused polycyclic compound of one or more embodiments introduces the first substituent into the fused ring core, and can effectively protect the empty p orbital of the boron atom, so that the degradation phenomenon caused by structural deformation can be prevented or reduced. Due to the structure with large steric hindrance, the exemplary compound can have an increased intermolecular distance, can suppress or reduce Dexter energy transfer, and can suppress or reduce the degradation of the lifespan caused by the increase in the concentration of triplet excitons. The light-emitting element of one or more embodiments includes the fused polycyclic compound of one or more embodiments as a light-emitting dopant of a thermally activated delayed fluorescence (TADF) light-emitting element, and can achieve high emission efficiency of the light-emitting element (particularly in the blue light wavelength region).
[0656] Compared with the examples, comparative example 1 shows the results of high driving voltage and degraded element life and emission efficiency. The comparative compound C1 included in comparative example 1 includes a fused ring structure having a boron atom and two nitrogen atoms as the center, but does not include the first substituent described in the present disclosure. Therefore, the steric protection effect of the boron atom in the plate-type or plate-like structure of the fused ring core may be reduced, and the intermolecular interaction may become difficult to predict. Therefore, when comparative compound C1 is applied to a light-emitting element, it can be confirmed that the driving voltage is high and the emission efficiency and life are reduced compared with the examples.
[0657] Compared with the examples, Comparative Example 2 shows the results of high driving voltage and degraded element life and emission efficiency. Comparative compound C2 included in Comparative Example 2 does not include the first substituent described in the present disclosure, and due to the introduction of the diphenylamine substituent, the HOMO energy level of Comparative Compound C2 is shallow, showing a hole capture phenomenon, and showing an increase in driving voltage and degradation of life. In the light-emitting element of Comparative Example 2 including Comparative Compound C2, due to hole capture, the dopant of Comparative Compound C2 directly generates excitons, and the concentration of triplet excitons increases to cause degradation of life.
[0658] Compared with the example, Comparative Examples 3 and Comparative Examples 4 show high driving voltage and degraded element life and emission efficiency results. Comparative Compounds C3 and C4 included in Comparative Examples 3 and Comparative Examples 4, respectively, have similar HOMO energy levels to the example compounds through similar core structures, but do not include the first substituent described in the present disclosure. Therefore, the properties of the bulky part are insufficient, the inhibition or reduction of Dexter energy transfer is insufficient, and the light-emitting elements of Comparative Examples 3 and Comparative Examples 4 show particularly degraded element life.
[0659] The light emitting element of one or more embodiments may exhibit improved light emitting element properties of high efficiency and long lifetime.
[0660] The fused polycyclic compound of one or more embodiments may be included in an emission layer of a light emitting element, and may help increase the emission efficiency and lifetime of the light emitting element.
[0661] The display device of one or more embodiments may show excellent or appropriate display quality by including the light emitting element of the present disclosure.
[0662] As utilized herein, the terms "substantially," "approximately," or similar terms are used as terms of approximation rather than terms of degree, and are intended to take into account the inherent deviations in measured or calculated values that one of ordinary skill in the art will recognize. "Approximately," as used herein, includes the stated value, and means within an acceptable range of deviations from a particular value as determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of a particular quantity (i.e., the limitations of the measurement system). For example, "approximately" may mean within one or more standard deviations, or within ±30%, ±20%, ±10%, ±5% of the stated value.
[0663] In the present disclosure, "does not include one or any "component"", "excludes one or any "component"" and / or "does not contain a "component"", etc. means that the "component" is not added, selected or used as a component in the composition, but due to other impurities and / or external factors, less than the appropriate amount of the "component" may still be included.
[0664] Any numerical range described herein is intended to include all subranges of the same numerical precision contained in the described range. For example, the range of "1.0 to 10.0" is intended to include all subranges between the described minimum value 1.0 and the described maximum value 10.0 (and including the described minimum value 1.0 and the described maximum value 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 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit described in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to amend this specification (including claims) to explicitly describe any subranges contained in the range explicitly described herein.
[0665] In the present disclosure, when the particles (e.g., quantum dots) are spherical, "size" means the particle diameter or the average particle diameter, and when the particles are non-spherical, "size" means 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 a particle size analyzer, for example, HORIBA, LA-950 laser particle size analyzer can be used. When the size of the particles is measured using a particle size analyzer, the average particle diameter (or size) is referred to as D50. D50 refers to the average diameter (or size) of the particles whose cumulative volume corresponds to 50% by volume in the particle size distribution (e.g., cumulative distribution), and refers to the particle size value corresponding to 50% of the smallest particles accumulated in the distribution curve in the order of the smallest particle size to the largest particle size when the total number of particles is 100%.
[0666] Any suitable hardware, firmware (e.g., a dedicated integrated circuit), software, or a combination of software, firmware, and hardware may be used to implement the light-emitting element / device, display device, display device, or any other related device / device or component according to the embodiments of the present disclosure described herein. For example, the various components of the device may be formed on an integrated circuit (IC) chip or on a separate IC chip. In addition, the various components of the device may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on a substrate. In addition, the various components of the device may be processes or threads that execute computer program instructions and interact with other system components to perform the various functions described herein, running on one or more processors in one or more computing devices. The computer program instructions are stored in a memory, which may be implemented in a computing device using a standard memory device (such as a random access memory (RAM) as an example). The computer program instructions may also be stored in other non-temporary computer-readable media (such as a CD-ROM, a flash drive, etc. as an example). In addition, it should be appreciated by those skilled in the art 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 particular computing device may be distributed to one or more other computing devices.
[0667] Although the embodiments of the present disclosure have been described, it is understood that the present disclosure should not be limited to these embodiments, but a person skilled in the art may make one or more suitable changes and modifications within the spirit and scope of the present disclosure according to the claims and their equivalents.
Claims
1. A fused polycyclic compound, wherein the fused polycyclic compound is represented by Formula 1: Formula 1 In formula 1, X is O or S, Ar1 and Ar2 are each independently 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, R2 and R a To R k are each independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms, and optionally combine with adjacent groups to form a ring, n1 is an integer from 0 to 2, and n2 is an integer from 0 to 4.
2. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound represented by Formula 1 is represented by Formula 2: Formula 2 In formula 2, R3 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 silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms, and optionally combines with an adjacent group to form a ring, n3 is an integer from 0 to 5, and X、Ar1、R1、R2、R a To R k , n1 and n2 are the same as those 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, R4 to R6 are each independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms, n4 is an integer from 0 to 5, n5 is an integer from 0 to 3, n6 is an integer from 0 to 4, and X、Ar1、R1、R2、R a To R k , n1 and n2 are the same as those defined in Formula 1.
4. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound represented by Formula 1 is represented by Formula 4: Formula 4 In formula 4, R7 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 silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms, and optionally combines with an adjacent group to form a ring, n7 is an integer from 0 to 5, and X、Ar2、R1、R2、R a To R k , n1 and n2 are the same as those defined in Formula 1.
5. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound represented by Formula 1 is represented by Formula 5-1 or Formula 5-2: Formula 5-1 Formula 5-2 In equation 5-1 and equation 5-2, Y is O or S, R8 to R 12 are independently hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted amine, substituted or unsubstituted oxy, substituted or unsubstituted thiol, substituted or unsubstituted boron, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms, R 13 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 silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms, and optionally combines with an adjacent group to form a ring, n8 is an integer from 0 to 3, n12 is an integer from 0 to 4, n9, n10 and n13 are each independently an integer from 0 to 5, n11 is an integer from 0 to 2, and X、Ar2、R1、R2、R a To R k , n1 and n2 are the same as those 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 one selected from Formula 6-1 to Formula 6-4: Formula 6-1 Formula 6-2 Formula 6-3 Formula 6-4 In equations 6-1 to 6-4, R x1 , R x2 , R y1 and R y2 are independently deuterium, halogen, substituted or unsubstituted amine, substituted or unsubstituted silyl, 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 and R x4 are each independently deuterium, halogen, substituted or unsubstituted amine, substituted or unsubstituted silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms, and optionally combine with an adjacent group to form a ring, and X、Ar1、Ar2、R1、R2、R a To R c , n1 and n2 are the same as those defined in Formula 1.
7. The fused polycyclic compound according to claim 6, wherein In equations 6-1 to 6-4, R x1 , R x2 , R y1 and R y2 Each is independently a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted N-carbazolyl group or a substituted or unsubstituted acridinyl group.
8. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound represented by Formula 1 is represented by Formula 7: Formula 7 In formula 7, R z is deuterium, halogen, substituted or unsubstituted amine, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms, and X、Ar1、Ar2、R1、R2、R d To R k , n1 and n2 are the same as those defined in Formula 1.
9. The fused polycyclic compound according to claim 8, wherein In formula 7, R z is 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 dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted xanthene group or a substituted or unsubstituted indolocarbazolyl group.
10. The fused polycyclic compound according to claim 1, wherein The fused polycyclic compound represented by Formula 1 is represented by Formula 8: Formula 8 In formula 8, X、Ar1、Ar2、R1、R2、R a To R k and n2 are the same as those defined in Formula 1.
11. The fused polycyclic compound according to claim 1, wherein The condensed polycyclic compound represented by Formula 1 is any one selected from the compounds in 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 emission layer, between the first electrode and the second electrode, Wherein, the emission layer comprises the fused 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 includes 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: Formula HT-1 In formula HT-1, M1 to M8 are independently N or CR 51 , L1 is 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, Y a It is a direct key, 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 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, and optionally combines with adjacent groups 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 of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring carbon atoms, b1 to b3 are each independently an integer from 0 to 10, Ar b To Ar d are independently hydrogen, deuterium, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 30 ring carbon atoms, and L2 to L4 are each 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; and Formula D-1 In formula D-1, Q1 to Q4 are independently C or N, C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring of 2 to 30 ring carbon atoms, L 11 To L 13 Each is independently a direct key, *-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, b1 to b3 are independently 0 or 1, R 61 To R 66 are 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, and d1 to d4 are each independently an integer from 0 to 4.
14. The light emitting element according to claim 13, wherein The second compound is selected from any one of the compounds in compound group 2: Compound Group 2 wherein "D" refers to deuterium, and "Ph" refers to substituted or unsubstituted phenyl.
15. The light emitting element according to claim 13, wherein The third compound is selected from any one of the compounds in compound group 3: Compound Group 3 wherein "D" refers to deuterium, and "Ph" refers to unsubstituted phenyl.
16. The light emitting element according to claim 13, wherein The fourth compound is selected from any one of the compounds in compound group 4: Compound Group 4 Here, "D" refers to deuterium.
17. A display device, comprising: Base layer; A circuit layer, on the substrate layer; as well as 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 on the first electrode, and an emission layer between the first electrode and the second electrode and including the condensed polycyclic compound according to any one of claims 1 to 11 as a first compound.
18. The display device according to claim 17, wherein: The display device further comprises a light control layer, which is on the display device layer and comprises quantum dots. The light emitting element is configured to emit light of a first color, and The light control layer includes: a first light control unit, including a first quantum dot that converts the first color light into a second color light in a wavelength region longer than the wavelength region of the first color light; a second light control unit, including a second quantum dot that converts the first color light into a third color light in a wavelength region longer than the wavelength region of the first color light and the wavelength region of the second color light; and a third light control unit, which is constructed to transmit the first color light.
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